View this post on the web at https://www.lennysnewsletter.com/p/anthropics-first-technical-pm-on
Dianne Penn is Head of Product for Anthropic’s AI Research and Labs teams. She joined in 2023 as Anthropic’s first technical product manager, when the entire product team was five engineers, and has since helped ship every model from Claude 2 through Fable, and helped incubate Claude Code, MCP, Skills, computer use, tool use, and reasoning. Before Anthropic, she helped build Alexa’s AI at Amazon and, before that, traded high-yield bonds at JP Morgan Chase.
Listen on YouTube [ https://substack.com/redirect/8b208b33-6198-4f72-b33b-a5156a9f4e17?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], Spotify [ https://substack.com/redirect/1fa00904-f6df-4cdd-a427-1cbcc19cefcc?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], and Apple Podcasts [ https://substack.com/redirect/43c12cbe-2a66-4561-9528-38808031fb0d?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
In our in-depth conversation, we discuss:
What Anthropic’s early days were like
The inflection points that turned Anthropic from an underdog into the fastest-growing company in history
How exactly Claude got so good at coding
The eval-driven development loop her team is pioneering
How to find joy in AI when everything is moving this fast
Why Claude’s willingness to push back is key to its success
Where human judgment remains irreplaceable
Brought to you by:
WorkOS [ https://substack.com/redirect/554e1aa2-d01a-422c-b0ab-a95835658358?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]—Make your app enterprise-ready, with SSO, SCIM, RBAC, and more
Mercury [ https://substack.com/redirect/1ff156e0-1cf7-4744-a0fd-0f2d41c51a79?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]—Radically different banking, now with Command
Where to find Dianne Penn:
• LinkedIn: linkedin.com/in/dianne-na-penn [ https://substack.com/redirect/b7fb5c94-07d6-4f90-9669-10a94793f03e?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Referenced:
• Anthropic: https://www.anthropic.com [ https://substack.com/redirect/39564a34-8a87-48d0-8901-4de339e524e6?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Golden Gate Claude: https://www.anthropic.com/news/golden-gate-claude [ https://substack.com/redirect/8568736e-d629-40f4-8bd9-8502ff404330?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Dario Amodei’s website: https://darioamodei.com [ https://substack.com/redirect/daa2e82c-2a4b-4028-9e44-c5c28086fff8?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Scaling Laws and Interpretability of Learning from Repeated Data: https://www.anthropic.com/research/scaling-laws-and-interpretability-of-learning-from-repeated-data [ https://substack.com/redirect/d7656793-2630-4e93-8d0e-329fd215e471?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Tokenmaxxing: How Top Builders Use AI To Do The Work Of 400 Engineers: https://www.ycombinator.com/library/Pa-tokenmaxxing-how-top-builders-use-ai-to-do-the-work-of-400-engineers [ https://substack.com/redirect/e6bb9917-8ccb-4e16-b0c0-d39d9cdf732f?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Garry Tan on X: https://x.com/garrytan [ https://substack.com/redirect/d810d095-5d77-4160-b906-1d305ac1e7ae?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Anthropic co-founder on quitting OpenAI, AGI predictions, $100M talent wars, 20% unemployment, and the nightmare scenarios keeping him up at night | Ben Mann: https://www.lennysnewsletter.com/p/anthropic-co-founder-benjamin-mann [ https://substack.com/redirect/e2527ad8-087b-45d5-aeb2-75489347898e?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Anthropic’s CPO on what comes next | Mike Krieger (co-founder of Instagram): https://www.lennysnewsletter.com/p/anthropics-cpo-heres-what-comes-next [ https://substack.com/redirect/0e4e5962-7d6c-432a-80fe-791bf5282aad?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Introducing Labs: https://www.anthropic.com/news/introducing-anthropic-labs [ https://substack.com/redirect/29642919-0b28-455e-8b31-1810fb00dec2?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Louis CK | about airplane Wi Fi: https://www.youtube.com/watch?v=me4BZBsHwZs [ https://substack.com/redirect/20582392-8ca0-458d-8fb2-1e096ebe7b54?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• What happens after coding is solved? | Fiona Fung (Manager of the Claude Code and Cowork Teams): https://www.lennysnewsletter.com/p/building-the-most-ai-pilled-engineering [ https://substack.com/redirect/e8f09ee3-cb3d-42e9-a401-330ee969fd15?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• The Anthropic Hive Mind: https://steve-yegge.medium.com/the-anthropic-hive-mind-d01f768f3d7b [ https://substack.com/redirect/e1c02979-a847-42b4-9bb3-5429a6947867?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• How to build a company that withstands any era | Eric Ries, Lean Startup author: https://www.lennysnewsletter.com/p/how-to-build-a-company-that-withstands [ https://substack.com/redirect/19af2b19-5948-4f4d-a4bd-16c7c382d093?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Fallout on Prime Video: https://www.amazon.com/dp/B0CN4GGGQ2 [ https://substack.com/redirect/058cb449-89c5-4ba8-a8dd-d97c17ca1baa?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Fallout (video game): https://fallout.bethesda.net [ https://substack.com/redirect/e53fd8d3-33e4-48ec-9932-4b311ee018c1?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Claude Tag: https://www.anthropic.com/news/introducing-claude-tag [ https://substack.com/redirect/98a0e6b4-9ea7-44f7-ac97-3f51d8643016?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Recommended books:
• Crucial Conversations: Tools for Talking When Stakes Are High: https://www.amazon.com/dp/0071771328 [ https://substack.com/redirect/ca32c2a6-cdc4-4f10-b779-7dba690ed94d?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• How to Raise an Adult: Break Free of the Overparenting Trap and Prepare Your Kid for Success: https://www.amazon.com/How-Raise-Adult-Overparenting-Prepare/dp/1627791779 [ https://substack.com/redirect/04522e5e-c666-4a2b-946e-4cc0d7ae7aae?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Incorruptible: Why Good Companies Go Bad... and How Great Companies Stay Great: https://www.amazon.com/dp/B0FWZZBPZB [ https://substack.com/redirect/c5e3c51d-8c46-4d03-9779-fc6a98960c35?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Production and marketing by https://penname.co/ [ https://substack.com/redirect/7801005b-f362-4a98-9576-ae6fde9e1280?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com [ mailto:podcast@lennyrachitsky.com ].
Lenny may be an investor in the companies discussed.
My biggest takeaways from this conversation:...
Unsubscribe https://substack.com/redirect/2/eyJlIjoiaHR0cHM6Ly93d3cubGVubnlzbmV3c2xldHRlci5jb20vYWN0aW9uL2Rpc2FibGVfZW1haWw_dG9rZW49ZXlKMWMyVnlYMmxrSWpvME1qWTFNVFV3TkRBc0luQnZjM1JmYVdRaU9qSXdOekl4TkRJd055d2lhV0YwSWpveE56ZzFNRFk1T0RjMkxDSmxlSEFpT2pFNE1UWTJNRFU0TnpZc0ltbHpjeUk2SW5CMVlpMHhNRGcwTlNJc0luTjFZaUk2SW1ScGMyRmliR1ZmWlcxaGFXd2lmUS43alZRQVdVQXQ5QjdxblZ2Y2U1QU1YZV9nb053TUhaRGhlMkwyanFsUXp3IiwicCI6MjA3MjE0MjA3LCJzIjoxMDg0NSwiZiI6dHJ1ZSwidSI6NDI2NTE1MDQwLCJpYXQiOjE3ODUwNjk4NzYsImV4cCI6MjEwMDY0NTg3NiwiaXNzIjoicHViLTAiLCJzdWIiOiJsaW5rLXJlZGlyZWN0In0.FOhRAnSolod_kymb2zQm1JO6EVjIXmWaJNBxWYPbGHM?
View Email
Anthropic’s first technical PM on token maxing, the jagged edge, and living in the future | Dianne Penn
lenny@substack.com7/26/2026
SubstackView this post on the web at https://www.lennysnewsletter.com/cp/208108478
Unsubscribe https://substack.com/redirect/2/eyJlIjoiaHR0cHM6Ly93d3cubGVubnlzbmV3c2xldHRlci5jb20vYWN0aW9uL2Rpc2FibGVfZW1haWw_dG9rZW49ZXlKMWMyVnlYMmxrSWpvME1qWTFNVFV3TkRBc0luQnZjM1JmYVdRaU9qSXdPREV3T0RRM09Dd2lhV0YwSWpveE56ZzBOelV3TURVd0xDSmxlSEFpT2pFNE1UWXlPRFl3TlRBc0ltbHpjeUk2SW5CMVlpMHhNRGcwTlNJc0luTjFZaUk2SW1ScGMyRmliR1ZmWlcxaGFXd2lmUS5jM296bUxhem1paE1aY0xQMFZILXhNX3lNMlZ0V3dDYzRFVEhrWWNqQ2c4IiwicCI6MjA4MTA4NDc4LCJzIjoxMDg0NSwiZiI6dHJ1ZSwidSI6NDI2NTE1MDQwLCJpYXQiOjE3ODQ3NTAwNTAsImV4cCI6MjEwMDMyNjA1MCwiaXNzIjoicHViLTAiLCJzdWIiOiJsaW5rLXJlZGlyZWN0In0.xJlrR-o37QQDOJ0jWb3of21MtJYe0DbOHuFBAndKVWk?
View Email
Inside PM at Stripe: What Comes After "Become a Builder"?
lenny@substack.com7/22/2026
SubstackView this post on the web at https://www.lennysnewsletter.com/p/how-to-take-a-sabbatical
👋 Hey there, I’m Lenny. Each week, I share deeply researched product, growth, and career advice. For more: Lenny’s Podcast [ https://substack.com/redirect/e28e9ba2-94cc-4262-a507-c55a18cc914a?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] | Lennybot [ https://substack.com/redirect/f1788dc5-1670-4bc1-993d-ec13381db7be?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] | How I AI [ https://substack.com/redirect/9098e042-2637-4f51-83e6-107aa1dde27f?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] | Become an AI-Native Builder [ https://substack.com/redirect/d2d23b47-c802-423d-ada2-69420d141120?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] and other favorite AI/PM courses [ https://substack.com/redirect/df5ca536-1565-4405-b9fe-973dce8d6442?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
P.S. Get a full free year of Cursor, Lovable, Google AI, Notion, Manus, Replit, Gamma, n8n, Canva, ElevenLabs, Factory, Wispr Flow, Fin, Supabase, Bolt, Linear, PostHog, Framer, Railway, Granola, Warp, Gumloop, Magic Patterns, Mobbin, ChatPRD, and Stripe Atlas, by becoming an Insider subscriber [ https://substack.com/redirect/2fb3e1fa-116a-4683-aaf9-6e68132787b5?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]. While supplies last. Yes, this is for real [ https://substack.com/redirect/baa93c0b-39aa-417b-bac6-aeb8d8d10761?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ].
This newsletter wouldn’t exist if I hadn’t taken a sabbatical.
Seven years into my stint at Airbnb, I took a three-month break. It was the first time I’d taken more than two weeks off in my more than 15-year career. I spent those months tinkering, reading, and traveling—and even snuck in a 10-day silent meditation retreat. At the end of it, I realized my heart wasn’t in the work anymore and that it was time for something new. So I left my job without much of a plan and spent the next six months exploring. Those six months turned into a year, that year turned into this newsletter, and the rest is history.
Looking back, I can say those were among the three most important months of my life, because they led me to what I do now—the most interesting, fulfilling, and impactful work I could have imagined.
Life makes it hard to get off the default path [ https://substack.com/redirect/96b605de-f57f-46e6-a19c-1c4e5b63a71c?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] and back onto a road of your own design. Sometimes that looks like leaving your job, like I did. Other times, it means reconnecting to why you’re doing the work you’re already doing. Either way, in my experience and that of many friends, significant time away from your day-to-day is necessary for the mental, physical, or emotional shift that will reveal what’s next. What you need is what today’s guest author DJ DiDonna [ https://substack.com/redirect/0f2b3518-640b-4cc6-945f-d1f1312cd686?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] calls “Big Time Off.”
DJ is the founder of The Sabbatical Project [ https://substack.com/redirect/fcf4b6f3-9396-4e92-b639-8dc48877c885?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] and an early guest contributor [ https://substack.com/redirect/aa5ec76b-49a7-49df-b0c1-d643293a274d?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] to this newsletter, and today DJ’s book Big Time Off [ https://substack.com/redirect/3420fe35-8e03-4c97-b49f-c73f0e84ced9?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] comes out! It’s a beautifully written, deeply researched book on the value of taking time off, with tangible advice, real-world case studies, and practical considerations for anyone who wants to shake things up. Below are some excerpts from his excellent book to help you start thinking about what a sabbatical might look like for you now or down the road.
I’d always wished there were a guide to help me think through that decision and make the most of this precious time off. We finally have one.
DJ will be in person in San Francisco at the Commonwealth Club on Thursday, July 23 [ https://substack.com/redirect/8b11c5e3-c25b-4f0e-a22d-89292ccbc412?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] (also streaming live online), interviewed by NPR podcast host Aarti Shahani. As a bonus, all Lenny’s readers are invited to the afterparty [ https://substack.com/redirect/41819b96-8bac-4d8c-af38-6eaaf86f6212?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] at Barebottle in Bernal Heights (8–10:30 p.m.)—your first drink is on DJ.
Also, for anyone who wants support on this journey, DJ has created a private WhatsApp community for Lenny’s readers. There he will host a live AMA on August 4 at 5 p.m. PT, as well as maintain an ongoing asynchronous forum for sabbatical questions, concerns, and ideas—click here to get your invitation [ https://substack.com/redirect/494c18be-2702-4364-9c2d-a65c9bd7922a?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ].
Let’s get into it.
Almost 10 years ago, I stepped away from my dream job—a fintech company I’d co-founded—to spend a few months prioritizing the important over the urgent. I walked a long pilgrimage, cared for my mother during an illness, and knocked out some smaller items on my list, like writing a song and remodeling my kitchen.
Like Lenny [ https://substack.com/redirect/aa5ec76b-49a7-49df-b0c1-d643293a274d?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], I came back changed. The time away made it clear that my old life no longer fit who I wanted to become.
So I left my company and set out to learn if my experience was unique or part of something bigger. I spent two years interviewing hundreds of sabbatical alums, which became a peer-reviewed paper and the foundation of my book, BIG TIME OFF: The Transformative Power of Sabbaticals and How to Take One [ https://substack.com/redirect/74ccf20c-5fe1-47b0-a4c4-0224d2efc5af?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ].
Making sabbaticals accessible to everyone—not just the lucky few like me—takes rigorous evidence: evidence to convince business leaders (many of you included) to create supportive workplace policies, and policymakers to create supportive public policies. In this book, you’ll find plenty of evidence with which to make a business case.
But human stories of change are also necessary to convince the part of you that thinks taking time off would be irresponsible or impossible. That’s why personal journeys like Lenny’s matter, and that’s what’s at the core of the book: inspiration, permission, and a blueprint for the experience of a lifetime.
I’ve included excerpts from two practical chapters below to help you figure out how to approach your sabbatical, and how to avoid some common mistakes from the start. I hope it’s helpful.
Excerpt from Chapter 4: Catalysts, Archetypes, and Barriers
The three archetypes of sabbatical takers
The type of sabbatical you choose depends on your life stage, job status, and a variety of other factors, such as personal responsibilities and desires. A 45-year-old father of three will not have the same considerations—or priorities—as a 30-something who just sold her company or a 26-year-old between jobs. That being said, a sabbatical doesn’t have to map perfectly with your age or the expectations of others. A gap year, for example, can make as much sense at 55 as it does at 18.
On top of what you’re able to pull off logistically, it’s important to consider your intentions for your time off in the context of who you are and what you really need. Which part of you is planning your sabbatical—is it your exhausted work self, your internal productivity monster, or the creative version of you from deep down? Understanding your tendencies doesn’t just give you a lens to help choose the most suitable sabbatical; it also provides a mirror to help you see the life that warrants reexamination. Ultimately, understanding the various types of sabbatical intentions will help you align your sabbatical to what you need and to return with greater self-understanding.
Over the course of my work, I have come across three archetypes among sabbatical takers: Achiever, Seeker, and Explorer. Recognizing yourself in these archetypes can help you make the best of your hard-earned break from routine. (You will likely identify with more than one of these archetypes, and that’s completely normal. In fact, many folks experience all three during their time off.)
Understanding what each archetype hopes to gain and into which traps they’re likely to fall will also allow you to take advantage of the experiences of many alumni who have gone before you. You’ll be better equipped to know when your work-obsessed self may be taking over. For example, sometimes you can redirect a competitive, work-obsessed mindset into a beneficial sabbatical activity, like volunteering your time for others or whipping yourself back into shape with gusto. Other times, you may realize that it’s this mindset itself, not your chosen activities, that you need some time away from.
The Achiever
The first and most common archetype is the achiever. Achievers view their sabbatical first and foremost as an opportunity to get things done.
Achievers are easy to recognize. They’re looking to make up for lost time by trying to squeeze years of life goals into a few months. They’re primed to view their sabbatical from the perspective of what they got done instead of how it made them feel. Don’t judge—most people initially conceive their sabbatical this way. Because we so rarely have freedom over large swaths of our life, it can be hard not to think about a sabbatical as a prime opportunity for productivity on the personal front.
What this archetype wants:
The achiever approaches their sabbatical with an accomplishment mindset. They often use external benchmarks—like fluency in a foreign language or completing a long hike—to determine whether they’re making progress. Or they attack private goals, like writing a book or organizing a community garden. This way, the achiever comes away from their sabbatical having accomplished something. Whether the product is applicable to their post-sabbatical life is beside the point. The achiever’s biggest fear is feeling like they wasted the opportunity to make some sort of tangible impact. They’ll use easily explainable milestones to guard themselves from looking or feeling unproductive.
An achiever can turn anything into an achievement. Type-A yogis are a textbook example. Instead of using their time off to simply do more yoga or attend a yoga retreat in a more exotic location, achievers devote their sabbaticals to becoming certified yoga instructors. It doesn’t matter that most of them don’t ever intend to teach yoga; the structure, magnitude, and mere fact of the accomplishment offer proof that they’ve “done something” on their time off. And that certified proof is irresistible.
What traps this archetype falls into:
Ironically, almost everyone I’ve spoken to who took this achievement-oriented approach to yoga regretted not taking the time to simply practice, learn, and play. What’s more, many of them found that the experience was almost anti-yoga. When you find yourself trying this hard to do something with your time off that’s supposed to be fun, the achiever mindset might be taking a little too much control over your sabbatical.
Tips for this archetype:
If you see yourself in this archetype, you’d be wise to force yourself to schedule a period of rest and healing at the start of your sabbatical. This is the time when many overachievers finally realize that their relationship to work has tangible negative effects on their bodies and minds. From ulcers to trigger fingers to insomnia and worse, stories of unexpectedly rapid healing from achievers who tend to themselves first when taking a sabbatical abound.
Consider how you think about your sabbatical wish list. Deconstruct the list of things you want to accomplish on sabbatical, paying attention to which goals have meaning for you personally versus ones that satisfy your accomplishment mindset. Does becoming a certified scuba instructor simply make a better post-sabbatical story than telling people your most treasured moments were playful days with your children? It’s almost inevitable that you will try to stuff your days and weeks on sabbatical with planned activities and aspirations, but for most, the real magic lies in serendipity and discovery, through play and experimentation.
The Seeker
The seeker also wants to accomplish something, but it’s less about reaching a destination than embarking on the journey. Seekers have questions, as much about themselves as the world outside them. The type of project a seeker pursues rarely feels urgent among the chaos and routine of normal life but remains important across large swaths of their life. Seekers are drawn to pilgrimages or road trips to reconnect with friends, family, people, and places from their past.
What this archetype wants:
Seekers are like personal archaeologists. They’re likely to engage in activities they used to love, trying to pick up on the scent of joy and engagement from the past. The external journey is a metaphor for the seeker’s ongoing internal search. They are deeply engaged in identity work, sensemaking on a path from uncertainty to certainty. A sabbatical beckons them to answer questions that have been bubbling up about the world and how they relate to it. Aspiring career switchers, or just folks looking to discern between garden-variety burnout and a strong signal to switch jobs, fit into this bucket.
I embarked on my sabbatical as a seeker. I had an overriding feeling that I’d ignored some core parts of myself for a long time. Primarily, that I’d neglected to make progress on deep questions within me about spirituality. I sensed that this project was important to me and required a lot more time and effort than I’d given it so far. I needed a more active approach if I wanted to make progress.
What traps this archetype falls into:
Seekers are prone to unrealistic expectations, which can put them at high risk of disappointment when they return from a sabbatical. The fact that they’ve finally made the time and space for something incredibly important and long overdue adds pressure to find the perfect next steps upon return. The kind of “good enough” steps that follow most sabbaticals—like staying at your old job for a bit longer or changing things up slightly before you make a big career move—are unlikely to satisfy seekers. In short, the quest for perfection becomes the enemy of success, spurring a more protracted sabbatical that becomes increasingly expensive and anxiety-inducing. Seekers should consider two strategies to avoid this vicious cycle.
Tips for this archetype:
Restrict the amount of time you allow yourself to seek. Seeking is a lifelong pursuit, not something you’re likely to knock out in several months. Instead of expecting to find your dream job (or state of being) by the end of your sabbatical, consider it a success to identify the next tangible step toward what your dream could be. You can control the process of the search, not the results. For example, have 20 coffee chats about career possibilities with people you admire. Your first sabbatical won’t be your last. To avoid burning out or spinning your wheels, it’s far better to end your sabbatical a bit closer to your ideal self than to flounder in the liminal state between the last thing and the next.
Prioritize others during your sabbatical. Seekers can easily lose track of time peering deep down into their personal rabbit hole. But sometimes the best way to learn about yourself is by setting your concerns aside entirely. Our research interviewees consistently recalled the time they spent with others as their most treasured moments. This finding emphasizes what the happiness literature has found over and over—that supporting other important people in your life and nurturing your relationships are instrumental to self-fulfillment.
The Explorer
Explorers have an appetite to see what’s out there in the world. They’re less concerned about how or if it will apply to their lives at the other end.
You don’t have to travel across the world to qualify as an explorer—I’ve met plenty of folks who, during their sabbaticals, spent time closer to home. They volunteered in their communities, experimented with new hobbies, and took shorter regional trips. All these detours took them out of their routine and cracked open their shells. Even going through a stack of books on your reading list can trigger awe. It can widen the aperture on what’s possible.
It’s rare to encounter a sabbatical that doesn’t incorporate a segment of pure exploration. Setting off on a journey is the most natural way to break free from routine life and to celebrate what’s next.
What this archetype wants:
For those who can afford to explore someplace far away, a sabbatical enables them to both get off the beaten path and to sufficiently sink in once they get there. As a burned-out marketing executive from our study put it, “I was having a very difficult time disengaging from my work for a couple of weeks after my sabbatical started, checking my personal email constantly and reflexively looking at my calendar. But as soon as my plane’s wheels left the runway en route to Bali—laptop behind—my work concerns evaporated completely.” Challenge yourself to get as far away from your routine experience of life as possible.
Exploration introduces uncertainty into our lives. In our world of limited vacation, we simply can’t afford to go off track and get lost. We can’t miss work, we can’t fly on weekdays, and we can’t risk traveling during shoulder seasons to save money. On sabbatical, you become time wealthy. Mistakes and inconveniences transform from vacation ruiners to serendipitous encounters. Exploring on our sabbaticals asks us instead to leave some important things to chance for a change. Living in the present and traveling flexibly leads to higher reported satisfaction among travelers and is correlated with greater psychological resilience.
What traps this archetype falls into:
While traveling far away may be the surest way to get out of your comfort zone, explorers who take an exotic, far-flung sabbatical often miss the beautiful things nearby, alienate themselves from their community, and set impossible standards for what quenches their sense of adventure. As a dyed-in-the-wool explorer, I know how difficult it is to go from a jet-setting expat to living a more sustainable life. But a well-balanced sabbatical (and life) requires also finding beauty in the mundane, closer to home.
Tip for this archetype:
Spend a significant portion of your sabbatical as a tourist in your own land. If you’re able to travel to far-flung places, do that first to completely disconnect and satisfy your more traditional sense of adventure. But then return to your routine surroundings and try to inhabit the energy that newcomers to a city have: Sign up for a special interest club, like a pottery or dance class. Volunteer locally or go to a city council meeting. It’s a totally normal mistake to treat your home turf as unworthy of the same attention and awe as some exotic locale. No matter how far afield your sabbatical takes you, the point isn’t to leave forever but to return home better off.
Excerpt from Chapter 9: First Principles
A field guide to your sabbatical
There’s a limit to how much you can prepare for a sabbatical.
There’s also a limit to how much you should prepare. You must make room for the unexpected opportunities that arise precisely from the lack of a plan, and the emotional discomfort that may accompany that. I get that this sounds like the worst-case scenario for the type As among us, but exploration enables growth, and growth requires discomfort. That’s the threshold you must cross on any journey of transformation, and the gooey insides of Sabbatical Land.
The advice you’ll appreciate the most from me won’t be a concrete recommendation for a beautiful beach or secluded retreat. Rather, it will be what helps you create the initial conditions for success: Your sabbatical should be long enough, it must contain the right components, and these pieces must be in the right order. These are the three guiding principles—setting, ingredients, and order.
This is a scaffolding to frame the journey in front of you, not be a “do this, don’t do that” checklist.
Three guiding principles
1. Setting: Duration and disconnection
Take big time off (more than you’re comfortable with)
In our time-scarce society, carving out enough uninterruptible time for your sabbatical is undoubtedly the most difficult step you’ll face. Is it any wonder that the most common question I receive is “How much time is sufficient for a sabbatical?”
I believe the sweet spot for sabbaticals is between six and 12 months. It’s not easy to take such a big chunk of time off, which is why most people take an abbreviated break of a month or six weeks, kicking the can down the road for a longer break when things open up in the future. While you’ll still undoubtedly get some benefits from an extended vacation, which we’ll discuss further in chapter 11, don’t mistake a shorter break for a sabbatical. Not taking enough time off puts you at risk of ending up just short of the sought-after experience. It often takes six to eight weeks to begin to feel like you’re truly disconnected from routine life.
We’ve all experienced that moment toward the end of a vacation when we finally feel like we’re sinking in and enjoying ourselves, only to realize it’s time to head back to reality. It’s like that with sabbaticals. The most transformative aspects of sabbaticals often don’t start until at least two months in, after we’ve had a chance to heal and sufficiently leave our former life behind.
While there is ample evidence to suggest that anything under two months is too short, there’s less clarity on how long is too long. A small chunk of people I’ve interviewed felt as though being out of the workforce for more than a year felt right, and it worked for them. That said, I’ve witnessed significantly more folks who kept moving their return dates further and further into the future, getting caught in a cycle of self-doubt and guilt the longer they stayed outside of routine life. This makes sense: sabbatical takers feel enormous pressure to make their hard-won time off “worth it.” If their problems haven’t been resolved or their lives completely changed, can they really return to regular life satisfied?
Stressing yourself psychologically and financially while waiting for the perfect job is almost always worse than taking a modest next step toward your ultimate goals. So plan for sufficient time in Sabbatical Land, but consider setting a deadline for returning to work, even if—especially if—you haven’t yet landed on your dream job.
Set impenetrable boundaries to truly disconnect
Once you create the right container, you need to protect it by setting boundaries. This is more difficult than ever. Some 30 years ago, going abroad meant untethering. Your boss couldn’t reach you. Getting in touch with the folks at home meant an expensive long-distance call. As for the news, the New York Times didn’t go online until 1996, and you’d need to be in a cybercafe to read it. Now, a flick of the thumb could reveal a crisis at work, a salacious news story, or a pressing issue closer to home, and in the process spoil your serenity for the rest of the day.
I’m a purist when it comes to not working while on sabbatical, particularly when it comes in the form of consulting gigs related to your routine job. No matter how attractive the opportunity seems—no matter how little time it claims to take up—these projects tend to expand to fill the time available. A two-hour call once per week has a surprising amount of disruptive force, preventing spontaneity, requiring connectivity, and psychologically tying you to a past version of yourself. So set an away message and create a mail rule to auto-delete all inbound emails. Make sure your colleagues understand what constitutes a sufficient “break the glass” moment to interrupt your time off.
Money might be able to buy you incrementally more time off, but it can never replace the large swaths of uninterrupted time off it destroys. No matter how tempting it may seem, you will regret porous boundaries between your old life and your time off.
2. Ingredients: Embodiment and play
Get out of your head and into your body (and soul)...
Unsubscribe https://substack.com/redirect/2/eyJlIjoiaHR0cHM6Ly93d3cubGVubnlzbmV3c2xldHRlci5jb20vYWN0aW9uL2Rpc2FibGVfZW1haWw_dG9rZW49ZXlKMWMyVnlYMmxrSWpvME1qWTFNVFV3TkRBc0luQnZjM1JmYVdRaU9qSXdOekU0TWpJM05Td2lhV0YwSWpveE56ZzBOak00TmpZNUxDSmxlSEFpT2pFNE1UWXhOelEyTmprc0ltbHpjeUk2SW5CMVlpMHhNRGcwTlNJc0luTjFZaUk2SW1ScGMyRmliR1ZmWlcxaGFXd2lmUS51bkZOQm44MUJFSDEzOEZCQ1ZLV2RMYzZGQ2pnVEtsRWU3Nkt0cG9OMnU0IiwicCI6MjA3MTgyMjc1LCJzIjoxMDg0NSwiZiI6dHJ1ZSwidSI6NDI2NTE1MDQwLCJpYXQiOjE3ODQ2Mzg2NjksImV4cCI6MjEwMDIxNDY2OSwiaXNzIjoicHViLTAiLCJzdWIiOiJsaW5rLXJlZGlyZWN0In0.f8tj0PPp0LewIoHUsoRWBlyQJ6ZebI33Ou4U9EtaDBc?
View Email
Why a sabbatical can change everything
lenny@substack.com7/21/2026
SubstackView this post on the web at https://www.lennysnewsletter.com/p/netflix-cpto-on-ai-and-the-future
Elizabeth Stone is the Chief Product and Technology Officer (CPTO) at Netflix, where she oversees Engineering, Product, and Design. Since her first appearance on the podcast two years ago—which remained my second-most-popular episode for more than a year—she has expanded her role to lead product, in addition to engineering. Before Netflix, Elizabeth was VP of Science at Lyft, Chief Operating Officer at Nuna, an economist at Analysis Group, and a trader at Merrill Lynch.
Listen on YouTube [ https://substack.com/redirect/d5033e70-35ec-4c1a-9289-e30d8b8af055?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], Spotify [ https://substack.com/redirect/524c7cc7-0374-4004-b785-eeb28b05245e?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], and Apple Podcasts [ https://substack.com/redirect/e9212ceb-2679-4d15-bf4b-ff76514e2fb0?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
In our in-depth conversation, we discuss:
Why “systems thinking” is now the most important skill she looks for
How to manage the flood of AI-generated output without losing quality or signal
How Netflix thinks about AI fluency as a universal expectation rather than a level-specific skill
What “excellence as an operating system” means
Brought to you by:
WorkOS [ https://substack.com/redirect/0e2f27a9-2f1d-4278-88af-b8ae1aae151c?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]—Make your app enterprise-ready, with SSO, SCIM, RBAC, and more
Mercury [ https://substack.com/redirect/0c62faee-99c7-464f-a81d-281dac4005fa?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]—Radically different banking, now with Command
Where to find Elizabeth Stone:
• LinkedIn: https://www.linkedin.com/in/elizabeth-stone-608a754 [ https://substack.com/redirect/d154e21b-5ad4-4fab-8762-b58f3e315b17?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Referenced:
• How Netflix builds a culture of excellence | Elizabeth Stone (CTO): https://www.lennysnewsletter.com/p/how-netflix-builds-a-culture-of-excellence [ https://substack.com/redirect/a3213890-270c-4c7e-829c-07dcf297a8e1?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Brian Chesky’s new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach [ https://substack.com/redirect/847c8da0-71be-480e-9e89-25f3a764ac3b?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• The design process is dead. Here’s what’s replacing it. | Jenny Wen (head of design at Claude): https://www.lennysnewsletter.com/p/the-design-process-is-dead [ https://substack.com/redirect/4c070b03-327c-4331-aeb4-95d124919e95?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Claude Code: https://www.anthropic.com/product/claude-code [ https://substack.com/redirect/2041857b-067b-48c8-81fb-80a699428754?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Claude Cowork: https://www.anthropic.com/product/claude-cowork [ https://substack.com/redirect/79268886-27ed-47a9-a807-4d0e474631e2?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Netflix’s “Keeper Test” and Why You Need It | Lorne Rubis: https://www.highlights.lornerubis.com/2015/08/the-netflix-keeper-test-and-the-courage-to-take-it [ https://substack.com/redirect/96ae7f7e-9040-4beb-8b58-6c06ae294442?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Innovation for Filmmaking, By Filmmakers: Why InterPositive Is Joining Netflix: https://about.netflix.com/en/news/why-interpositive-is-joining-netflix [ https://substack.com/redirect/909c1da2-074b-4271-9f3c-6730f024c55d?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• InterPositive: https://weareinterpositive.com [ https://substack.com/redirect/3cdbe468-745f-4bb0-9f3a-6aebf0886a1a?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Netflix Prize: https://en.wikipedia.org/wiki/Netflix_Prize [ https://substack.com/redirect/f92c1537-fff4-4dd7-95fb-f16f1fd91df2?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Quarterback on Netflix: https://www.netflix.com/title/81482895 [ https://substack.com/redirect/f51e9601-8360-4131-993d-75d8895ea93f?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• The Bill Simmons Podcast on Netflix: https://www.netflix.com/title/82186214 [ https://substack.com/redirect/aec85655-53ab-4fd2-a7c1-494c42e64652?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Spencer Pratt on Instagram: https://www.instagram.com/spencerpratt [ https://substack.com/redirect/c4372d51-89e3-432a-a9a8-2a632f6db8ff?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Salman Rushdie’s Substack: https://salmanrushdie.substack.com [ https://substack.com/redirect/0cb4985a-5843-4a5e-a3fb-26bc07522252?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Remarkably Bright Creatures on Netflix: https://www.netflix.com/title/81911351 [ https://substack.com/redirect/91e2dc11-6c87-4770-b5b2-d4a29bec9fd6?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Eight Sleep: https://www.eightsleep.com [ https://substack.com/redirect/d1c37de7-771e-482f-81a8-bd818a659cc2?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Tour de France: https://www.letour.fr/en [ https://substack.com/redirect/30e60997-9c80-453f-920f-2906e9e25498?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Recommended books:
• Thinking in Systems: https://www.amazon.com/Thinking-Systems-Donella-H-Meadows/dp/1603580557 [ https://substack.com/redirect/a786d7c6-9942-494e-99f8-cbbcb7dfb518?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Into Thin Air: A Personal Account of the Mt. Everest Disaster: https://www.amazon.com/Into-Thin-Air-Personal-Disaster/dp/0385494785 [ https://substack.com/redirect/3012101c-80dd-4b2a-aa36-90dd8d81e3ba?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Liar’s Poker: https://www.amazon.com/Liars-Poker-Norton-Paperback-Michael/dp/039333869X [ https://substack.com/redirect/4bc902f5-bcf2-4ac3-9f29-c0c9a0036dd0?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Production and marketing by https://penname.co/ [ https://substack.com/redirect/90031ea9-c127-4c62-a6de-b72761b79f7c?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com [ mailto:podcast@lennyrachitsky.com ].
Lenny may be an investor in the companies discussed.
My biggest takeaways from this conversation:...
Unsubscribe https://substack.com/redirect/2/eyJlIjoiaHR0cHM6Ly93d3cubGVubnlzbmV3c2xldHRlci5jb20vYWN0aW9uL2Rpc2FibGVfZW1haWw_dG9rZW49ZXlKMWMyVnlYMmxrSWpvME1qWTFNVFV3TkRBc0luQnZjM1JmYVdRaU9qSXdOVFkzTlRnMU1Td2lhV0YwSWpveE56ZzBORFkxTURjNUxDSmxlSEFpT2pFNE1UWXdNREV3Tnprc0ltbHpjeUk2SW5CMVlpMHhNRGcwTlNJc0luTjFZaUk2SW1ScGMyRmliR1ZmWlcxaGFXd2lmUS5PdEg2NjBBUjB5M0w1cUVRS0ZDMHRZLVZDd0pyek42cDcxb1JGazFyeVBBIiwicCI6MjA1Njc1ODUxLCJzIjoxMDg0NSwiZiI6dHJ1ZSwidSI6NDI2NTE1MDQwLCJpYXQiOjE3ODQ0NjUwNzksImV4cCI6MjEwMDA0MTA3OSwiaXNzIjoicHViLTAiLCJzdWIiOiJsaW5rLXJlZGlyZWN0In0.goB8hdp0F6zBB63b6Gds1N5yuet2VHTGatWz5NXkFuo?
View Email
Netflix CPTO on AI and the future of product and tech roles | Elizabeth Stone
lenny@substack.com7/19/2026
SubstackView this post on the web at https://www.lennysnewsletter.com/cp/207178550
Unsubscribe https://substack.com/redirect/2/eyJlIjoiaHR0cHM6Ly93d3cubGVubnlzbmV3c2xldHRlci5jb20vYWN0aW9uL2Rpc2FibGVfZW1haWw_dG9rZW49ZXlKMWMyVnlYMmxrSWpvME1qWTFNVFV3TkRBc0luQnZjM1JmYVdRaU9qSXdOekUzT0RVMU1Dd2lhV0YwSWpveE56ZzBNVE0wTURRd0xDSmxlSEFpT2pFNE1UVTJOekF3TkRBc0ltbHpjeUk2SW5CMVlpMHhNRGcwTlNJc0luTjFZaUk2SW1ScGMyRmliR1ZmWlcxaGFXd2lmUS5GODlHY3ZIWEVweXVSTmhKRDNGQVJVMm1wX2pWRU5KWjc3TFg4Sk90WWNJIiwicCI6MjA3MTc4NTUwLCJzIjoxMDg0NSwiZiI6dHJ1ZSwidSI6NDI2NTE1MDQwLCJpYXQiOjE3ODQxMzQwNDAsImV4cCI6MjA5OTcxMDA0MCwiaXNzIjoicHViLTAiLCJzdWIiOiJsaW5rLXJlZGlyZWN0In0.SzHI3DWBsVed91_7t92SmatJS4b4KqH8wIjTW5YTbXI?
View Email
Builder-Executives Are Getting Paid Like Pro Athletes
lenny@substack.com7/15/2026
SubstackView this post on the web at https://www.lennysnewsletter.com/p/how-tech-workers-actually-feel-about
Noam Segal is a longtime research leader across Airbnb, Meta, Twitter, Zapier, Intercom, and Figma, a certified coach, AI builder, and my community research lead. Together, we run the annual Tech Worker Sentiment Survey, now in its second year and one of the largest of its kind: a quantitative study of how people in tech actually feel about their jobs, AI, burnout, and the future of their careers. This year’s survey captured responses from thousands of workers across product, engineering, design, research, marketing, data, and sales, and the results are striking.
Listen on YouTube [ https://substack.com/redirect/4ae32ae7-ce8b-4031-a371-80e431649a94?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], Spotify [ https://substack.com/redirect/3d091990-a0ce-428c-a217-40aad1f5a20b?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], and Apple Podcasts [ https://substack.com/redirect/1831e9be-373f-4309-8f74-1bfe6bda97e1?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
In our in-depth conversation, we discuss:
Why AI has split the tech workforce almost exactly in half—one half that’s thriving, another that’s shaken
The four emotional archetypes defining tech workers right now (the Energized, the Conflicted, the Disoriented, and the Resentful)
Why burnout has jumped an alarming 11 points in a single year
Why nobody in tech would recommend their job to someone entering the industry today
The #1 fear in tech right now (it’s not job loss to AI)
Why managers are the single biggest lever for employee well-being
Concrete advice for what employees and leaders can do right now
Brought to you by:
WorkOS [ https://substack.com/redirect/36311ab9-bbcc-49ca-9200-51de5cbd4fb4?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]—Make your app enterprise-ready, with SSO, SCIM, RBAC, and more
Mercury [ https://substack.com/redirect/ecfc5199-f6f3-4e52-addd-a1dd39f4309f?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]—Radically different banking, now with Command
Where to find Noam Segal:
• X: https://x.com/noamseg [ https://substack.com/redirect/1a8d22e5-0151-4383-aac7-1023d5afab9b?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• LinkedIn: https://www.linkedin.com/in/noamsegal [ https://substack.com/redirect/a5f93bf5-5fed-4316-9871-255265bf9320?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Referenced:
• How tech workers are feeling in 2026: a workforce splitting in two: https://www.lennysnewsletter.com/p/how-tech-workers-are-feeling-in-2026 [ https://substack.com/redirect/05fa3f12-7f3f-410a-8a80-0ee58d53de15?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• How tech’s most resilient workers handle burnout: https://www.lennysnewsletter.com/p/how-techs-most-resilient-workers [ https://substack.com/redirect/afc6d8f8-a3d6-4c30-a63a-dfa5a3eb6531?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Please stop the AI Confidence Theater: https://www.elenaverna.com/p/please-stop-the-ai-confidence-theater [ https://substack.com/redirect/cb06f66a-858a-442e-860b-07baf1276a31?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Velocity over everything: How Ramp became the fastest-growing SaaS startup of all time | Geoff Charles (VP of Product): https://www.lennysnewsletter.com/p/velocity-over-everything-how-ramp [ https://substack.com/redirect/9dec4000-9d88-4282-bc07-94ee1c24e8ef?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• NPS Is The Worst: https://www.npsistheworst.com [ https://substack.com/redirect/5ca94e6d-1ab0-4929-a394-abccabbedbcd?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• The Terminator: https://www.imdb.com/title/tt0088247 [ https://substack.com/redirect/9848cef2-399c-43a8-989e-199435a8b2d2?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Skynet: https://terminator.fandom.com/wiki/Skynet [ https://substack.com/redirect/de29e70f-e8c7-4029-bf71-4c4868062a9e?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Inside Devin: The world’s first autonomous AI engineer that’s set to write 50% of its company’s code by end of year | Scott Wu (CEO and co-founder of Cognition): https://www.lennysnewsletter.com/p/inside-devin-scott-wu [ https://substack.com/redirect/015ce53c-fb79-43f9-b286-07ca9724e603?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Devin: https://devin.ai [ https://substack.com/redirect/414f2176-3243-454e-8d0a-a526be180ba3?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• An AI state of the union: We’ve passed the inflection point, dark factories are coming, and automation timelines | Simon Willison: https://www.lennysnewsletter.com/p/an-ai-state-of-the-union [ https://substack.com/redirect/878fd407-02a6-498b-bc21-21eb8111fca1?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Redeploying Fable 5: https://www.anthropic.com/news/redeploying-fable-5 [ https://substack.com/redirect/40b34297-0bce-493a-b6c5-42f5da4193ff?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Why half of product managers are in trouble | Nikhyl Singhal (Meta, Google): https://www.lennysnewsletter.com/p/why-half-of-product-managers-are-in-trouble [ https://substack.com/redirect/7941e443-90de-4d03-8e86-933fce806dbf?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Inside Linear: Building with taste, craft, and focus | Karri Saarinen (co-founder, designer, CEO): https://www.lennysnewsletter.com/p/inside-linear-building-with-taste [ https://substack.com/redirect/ddbb49c2-4953-4195-8525-d586e487661e?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Building beautiful products with Stripe’s Head of Design | Katie Dill (Stripe, Airbnb, Lyft): https://www.lennysnewsletter.com/p/building-beautiful-products-with [ https://substack.com/redirect/ce6bc61a-baae-4e11-9063-474fd48c6e19?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• The design process is dead. Here’s what’s replacing it. | Jenny Wen (head of design at Claude): https://www.lennysnewsletter.com/p/the-design-process-is-dead [ https://substack.com/redirect/1ab56820-00ba-4788-a662-288a7dea1d4c?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• OpenAI Codex lead on the new shape of product work | Andrew Ambrosino: https://www.lennysnewsletter.com/p/openai-codex-lead-on-the-new-shape [ https://substack.com/redirect/226ca83b-eb37-47a3-8ce5-7402033fb7e0?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Elon Musk: ‘Chances are we’re all living in a simulation’: https://www.theguardian.com/technology/2016/jun/02/elon-musk-tesla-space-x-paypal-hyperloop-simulation [ https://substack.com/redirect/123f44cd-a647-4963-a642-705496c59cef?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Production and marketing by https://penname.co/ [ https://substack.com/redirect/6275656a-09ff-46bf-ac99-c695ba5f52ce?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com [ mailto:podcast@lennyrachitsky.com ].
Lenny may be an investor in the companies discussed.
My biggest takeaways from this conversation:...
Unsubscribe https://substack.com/redirect/2/eyJlIjoiaHR0cHM6Ly93d3cubGVubnlzbmV3c2xldHRlci5jb20vYWN0aW9uL2Rpc2FibGVfZW1haWw_dG9rZW49ZXlKMWMyVnlYMmxrSWpvME1qWTFNVFV3TkRBc0luQnZjM1JmYVdRaU9qSXdOVFkzTXpVek5pd2lhV0YwSWpveE56Z3pPRFl3TkRjeExDSmxlSEFpT2pFNE1UVXpPVFkwTnpFc0ltbHpjeUk2SW5CMVlpMHhNRGcwTlNJc0luTjFZaUk2SW1ScGMyRmliR1ZmWlcxaGFXd2lmUS5jcFdVYTdiamZjMlkxaV9meHhUSlBtal9tcDEwOG1GTWZmNkpUaFhZRmk4IiwicCI6MjA1NjczNTM2LCJzIjoxMDg0NSwiZiI6dHJ1ZSwidSI6NDI2NTE1MDQwLCJpYXQiOjE3ODM4NjA0NzEsImV4cCI6MjA5OTQzNjQ3MSwiaXNzIjoicHViLTAiLCJzdWIiOiJsaW5rLXJlZGlyZWN0In0.3jSYv-vS1wEPwiNVEySXn_jpmSPISp74xtxSrGjpt08?
View Email
How tech workers actually feel about AI in 2026 | Annual AI sentiment survey (Noam Segal)
lenny@substack.com7/12/2026
SubstackView this post on the web at https://www.lennysnewsletter.com/p/adam-mosseri-ai-is-a-tailwind-for
Adam Mosseri is the Head of Instagram, where he oversees an app used by over 3 billion people. He also leads the team building Threads. Adam has run Instagram for longer than its founders did, after taking over from Kevin Systrom and Mike Krieger in 2018. A designer by training, he spent over 15 years at Meta, starting as a designer on Facebook’s mobile app, rising to lead Facebook’s News Feed, and eventually chosen to lead Instagram. During his tenure, Instagram’s user base has more than tripled.
Listen on YouTube [ https://substack.com/redirect/51d6d84c-1095-425c-b40a-7e70dd77322a?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], Spotify [ https://substack.com/redirect/4b131ae2-ef19-4937-a7cc-c30d896de2a6?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], and Apple Podcasts [ https://substack.com/redirect/f7ec3f6a-6601-41d5-9407-eef1cb03f326?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
In our in-depth conversation, we discuss:
How the canonical product team structure is changing in 2026, from baker’s-dozen specialist teams to lean pods of four to six generalists
The rise of the “product staff” role—a blending of PM, design, data science, and research into one generalist operator
Why Adam is bullish on designers even as functional boundaries dissolve, and which roles are most at risk
What the Instagram algorithm knows about you, and why it’s only now catching up to what people assumed it knew years ago
Why the rise of AI-generated content is a tailwind for Instagram, and how the company is thinking about creator identity in a synthetic-content world
The two biggest product failures of Adam’s career—Facebook Home and the first version of Reels
Brought to you by:
WorkOS [ https://substack.com/redirect/5bdfa078-4a5a-47bc-a533-3ad3d502b800?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]—Make your app enterprise-ready, with SSO, SCIM, RBAC, and more
Mercury [ https://substack.com/redirect/d62b865c-7080-47c3-bb47-e7e5bc00ff57?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]—Radically different banking, now with Command
Where to find Adam Mosseri:
• X: https://x.com/mosseri [ https://substack.com/redirect/1f40713c-47c4-450c-8704-a1ef1804872a?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• LinkedIn: linkedin.com/in/mosseri [ https://substack.com/redirect/873670c5-d580-47e9-8e28-46cb0ba358d0?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Instagram: https://www.instagram.com/mosseri [ https://substack.com/redirect/906c8039-accf-4546-aa54-18e6717da871?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Referenced:
• What happens after coding is solved? | Fiona Fung (Manager of the Claude Code and Cowork Teams): https://www.lennysnewsletter.com/p/building-the-most-ai-pilled-engineering [ https://substack.com/redirect/3f14e4bc-3653-409c-87a7-6ff118765332?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Claude Code: https://www.anthropic.com/product/claude-code [ https://substack.com/redirect/0d5a2657-fbce-43a5-a0f9-87aa8e4b7f48?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Claude Cowork: https://www.anthropic.com/product/claude-cowork [ https://substack.com/redirect/26e77af3-d1e1-4321-9976-74d8482f9d51?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Head of Claude Code: What happens after coding is solved | Boris Cherny: https://www.lennysnewsletter.com/p/head-of-claude-code-what-happens [ https://substack.com/redirect/3ff7d36b-d7bf-4505-be40-1ad226af7906?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• A rational conversation on where AI is actually going | Benedict Evans: https://www.lennysnewsletter.com/p/a-rational-conversation-on-where [ https://substack.com/redirect/fa22b02c-07c3-4c24-ab72-ac2ea3d7933e?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• OpenAI’s CPO on how AI changes must-have skills, moats, coding, startup playbooks, more | Kevin Weil (CPO at OpenAI, ex-Instagram, Twitter): https://www.lennysnewsletter.com/p/kevin-weil-open-ai [ https://substack.com/redirect/5cd18f58-27f5-4bed-a0bf-4fc665abdaca?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Mythos: https://www.anthropic.com/claude/mythos [ https://substack.com/redirect/8ebaa51b-f414-4ac3-8f5c-f3ebd70ef67c?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Fable: https://www.anthropic.com/claude/fable [ https://substack.com/redirect/e917ea20-ab3f-46a8-81ac-ce09a0eb666d?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Pluralistic: The Reverse-Centaur’s Guide to Criticizing AI: https://pluralistic.net/2025/12/05/pop-that-bubble [ https://substack.com/redirect/3d7fac19-741e-40bb-af73-54d1d59d709c?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Plastic Dream Sequence on Instagram: https://www.instagram.com/plasticdreamsequence [ https://substack.com/redirect/a4c22b20-cacd-462a-96f1-68d883e7fad0?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• TikTok: https://www.tiktok.com [ https://substack.com/redirect/daf33c47-82dd-4640-b219-88e2f9a912cf?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Facebook–Cambridge Analytica data scandal: https://en.wikipedia.org/wiki/Facebook%E2%80%93Cambridge_Analytica_data_scandal [ https://substack.com/redirect/6aba7d45-83f3-44e7-81b4-96faf7428bb7?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Facebook Home: https://en.wikipedia.org/wiki/Facebook_Home [ https://substack.com/redirect/5648669d-adbe-4111-a131-374763dd8675?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Production and marketing by https://penname.co/ [ https://substack.com/redirect/4ae6a88e-f0e6-4c7f-a248-cfcca1542167?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com [ mailto:podcast@lennyrachitsky.com ].
Lenny may be an investor in the companies discussed.
My biggest takeaways from this conversation:...
Unsubscribe https://substack.com/redirect/2/eyJlIjoiaHR0cHM6Ly93d3cubGVubnlzbmV3c2xldHRlci5jb20vYWN0aW9uL2Rpc2FibGVfZW1haWw_dG9rZW49ZXlKMWMyVnlYMmxrSWpvME1qWTFNVFV3TkRBc0luQnZjM1JmYVdRaU9qSXdNelEzTmpnd09Td2lhV0YwSWpveE56Z3pOakF4TVRVMUxDSmxlSEFpT2pFNE1UVXhNemN4TlRVc0ltbHpjeUk2SW5CMVlpMHhNRGcwTlNJc0luTjFZaUk2SW1ScGMyRmliR1ZmWlcxaGFXd2lmUS5LU000c3JwOWpuY0pMejlnYnpnZmlKalFuV0dpTE05UElTQjc1QUhBM2NzIiwicCI6MjAzNDc2ODA5LCJzIjoxMDg0NSwiZiI6dHJ1ZSwidSI6NDI2NTE1MDQwLCJpYXQiOjE3ODM2MDExNTUsImV4cCI6MjA5OTE3NzE1NSwiaXNzIjoicHViLTAiLCJzdWIiOiJsaW5rLXJlZGlyZWN0In0.lx9ASGNczByngpI2DT9XxK4sgZ4ET6kEgtIegCofS7c?
View Email
Adam Mosseri: AI is a tailwind for authenticity
lenny@substack.com7/9/2026
SubstackView this post on the web at https://www.lennysnewsletter.com/p/how-tech-workers-are-feeling-in-2026
👋 Hey there, I’m Lenny. Each week, I share deeply researched product, growth, and career advice. For more: Lenny’s Podcast [ https://substack.com/redirect/83e64090-d5ec-4a88-932c-a8133026f3ec?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] | Lennybot [ https://substack.com/redirect/1ccde497-c7a3-459e-9a0f-3fa12448c274?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] | How I AI [ https://substack.com/redirect/37118aa3-6e4d-4c4b-9817-ac46f2567121?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] | Become an AI-Native Builder [ https://substack.com/redirect/8b0daf80-17ee-473c-8c4a-11c38efd1463?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] and other favorite AI/PM courses [ https://substack.com/redirect/600c2c11-442a-4fab-ac48-e581aa40bf94?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ].
P.S. Get a full free year of Google AI, Cursor, Lovable, Notion, Manus, Replit, Gamma, n8n, Canva, ElevenLabs, Factory, Wispr Flow, Fin, Supabase, Bolt, Linear, PostHog, Framer, Railway, Granola, Warp, Gumloop, Magic Patterns, Mobbin, ChatPRD, and Stripe Atlas by becoming an Insider subscriber [ https://substack.com/redirect/5c45dfa1-9540-40f4-94b4-6dea2878d089?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]. Yes, this is for real [ https://substack.com/redirect/541b967a-3ce5-4dfd-8c64-1a1770528172?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ].
A year ago, we ran our first large-scale survey [ https://substack.com/redirect/c9b16bf7-550a-45b4-a2dd-29d1e638890f?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] of how tech workers feel about their jobs and careers. We summed up what emerged in four words: burned out, but optimistic. Today we’re back with the results from our 2026 survey, and it’s a tale of two workforces.
One half feels amplified by AI—more capable, more confident, more excited than they’ve been in their entire career. The other half feels shaken by it—less sure of their value and whether there’s still a place for them. Which side of that line people fall on predicts how they feel about their career more than anything else, including their current role, seniority, company size, or any other measure we collected. The workforce is bifurcating into two realities.
But there’s more: Burnout overall jumped 11 points in a single year, and four in 10 respondents are worried about losing their job. Even those who feel optimistic about their own career may not recommend that friends follow their path. In the AI era, everyone agrees the ground is moving. No one is sure yet if it’s an earthquake or a launch.
We think these findings are important enough that we’re making this post free for everyone.
Let’s break it down.
Our biggest takeaways
The workforce is splitting in two. Tech workers are either amplified by AI or shaken by it, and that divide shapes their feelings about work more than any title, tenure, or company.
Burnout is surging, and optimism is fading. Significant burnout rose from 44.7% to 55.7% of respondents, while career optimism fell from 54.8% to 48.7%. Those who feel destabilized by AI are feeling the least optimistic and the most burned out. A worrisome trend.
Tech workers wouldn’t recommend their own field. More than half (53%) would steer a newcomer away from a career in their role, even though they’re optimistic about their own future.
Productivity is up, but quality is questionable. 82% say AI is making them measurably more productive, but many worry the gains are coming at the cost of the sharpness of the work and the worker.
The underlying fear is of being overworked. Only 22% worry about “losing my job to AI.” Far more worry about being expected to do more for the same pay (51%), getting trapped in an unsustainable pace (46%), and the quality of their work going down (41%).
Almost everyone is ambivalent. 77% of respondents picked at least one positive and one negative emotion about AI. The average person selected more than five emotions. The defining feeling about AI is ambivalence.
Designers and researchers are the most worried. They report the most AI anxiety, the most fear of job loss, the worst-rated managers, and the lowest willingness to recommend their field. It’s a continuation of a trend we flagged last year.
Founders are still the happiest people in tech, and small companies are still the best places to work. Both findings replicate from 2025, and both are statistically robust.
Managers are still the biggest lever for happiness. Manager quality remains the strongest driver of burnout and one of the strongest drivers of everything else.
The industry, in tech workers’ own words, is “chaotic.” Asked to describe the state of tech in a sentence, the most common theme by far was chaos, though the sentiment was split almost evenly between excitement and dread.
Takeaway 1: The workforce is splitting in two
To understand AI’s deeper impact on people, we asked an existential question: How has working with AI shifted how you see yourself as a professional? We gave respondents five options. Here’s how they responded:
“Amplified (I can do more, and better)”: 49.0%
“Redefined (My role is changing shape, but I don’t see that as clearly positive or negative)”: 27.4%
“Destabilized (I’m less sure where I stand or what’s really mine)”: 13.9%
“Diminished (I feel less essential or less valuable)”: 5.0%
“Unchanged”: 3.2%
When we lined up that question against the rest of the survey, the four identity groups differed dramatically:
As you go from “amplified” to “diminished,” optimism collapses, burnout climbs, layoff fear climbs, and willingness to recommend the field falls off. The people who feel amplified by AI are thriving. Those who feel diminished by it are in distress on every measure.
To make sure this wasn’t an artifact, we ran the numbers a few different ways:
In a regression pitting every variable against each other, AI-identity stance was the single strongest predictor of career optimism (standardized β = +0.39) and of whether someone would recommend their field (β = +0.60)—stronger than role, level, and company size combined.
As an effect size, the gap between the “amplified” and “diminished” groups on optimism is large (Cohen’s d ≈ 1.55). For context, the famously strong “founder effect” we’ll discuss later clocks in at d ≈ 0.56. The AI divide is roughly three times as large as that. It is, by a wide margin, the biggest effect in the dataset.
The question that best predicts how a tech worker feels about their work, in 2026, is no longer “What do you do?” or “Where do you work?” It’s “What has AI done to your sense of who you are?”
Meet the four tech workers of 2026
We did one more pass on this data: instead of using a single identity question, we clustered respondents based on the full pattern of emotions they reported about AI. Four types emerged, and you almost certainly recognize them.
The Energized (41%). The all-in adopters. They lead with “excited” (91%), “curious” (83%), and “hopeful” (59%). They’re the most optimistic group, the least burned out, and the only segment with a clearly positive read on their field. For them, AI truly seems like a superpower.
“Product has become fun again! You become an explorer, you play around . . . you spend long hours full of excitement. We’re in an amusement park.” —PM, Principal IC
The Conflicted (35%). The ambivalent center of gravity—and the largest group after the Amplified. Their signature emotions are “conflicted—holding positive and negative feelings at once” (68%)—and “curious” (64%), trailed closely by “overwhelmed” (56%) and “tired” (55%). They haven’t soured on AI; they’re just exhausted by the work of keeping up with it while holding two feelings at the same time.
“I’m simultaneously having the most fun I’ve had as a product builder and also feeling the most uncertainty I’ve felt. I’m confident I’ll be able to keep my skills sharp and adapt, but I’m not yet sure what it is that I’ll need to adapt into.” —PM, Senior IC
The Disoriented (12%). Defined almost entirely by one feeling: “disoriented—my role keeps shifting,” layered with “overwhelmed” (74%) and “tired” (73%). These are people watching their job change shape beneath them faster than they can find their footing again. They still think AI is somewhat useful. They’re not “refusers.” They’re just losing the thread of their role in the workplace.
“Things are so uncertain, we’re like farmers on the cusp of the industrial revolution. We know going into farming is the wisest long-term career choice, but we don’t see a clear path. This kind of uncertainty crowds out productivity.” —VP Product
The Resentful (12%). The burned-out and checked-out. Every one of them selected “resentful—I feel pressured to use AI,” and they cluster with “tired,” “conflicted,” and “overwhelmed.” They report the lowest optimism, the lowest willingness to recommend their field, and the lowest sense that AI is helping them at all. This is AI fatigue transformed into resistance.
“Tech overall kind of sucks right now. We used to adopt new technology because we were excited about the cool new things we could do. Now all we hear is ‘Use AI or you will lose your job’—and then people get fired anyway. I hate it.” —Director of Product
Takeaway 2: Burnout is surging, and optimism is fading
Significant burnout is now the majority experience for tech workers. 55.7% of working tech professionals report significant burnout—meaning they describe themselves as “moderately,” “very,” or “completely” burned out. Last year, that number was 44.7%. More than a quarter (26.2%) are now “very” or “completely” burned out.
Career optimism is dropping. Fewer than half (48.7%) of respondents are optimistic about the future of their career (down from 54.8% being optimistic last year). We’ve gone from “burned out but optimistic” in 2025 to “significantly burned out, and not that optimistic” a year later. We’re curious (and a little scared) about how this will look in a year.
That being said, job enjoyment is holding up: 42.6% enjoy their work “very much” or “extremely”; another 36.7% rate it “moderately”; and only about one in five (20.6%) enjoy it slightly or not at all.
Why the apparent contradiction? Enjoyment, burnout, and optimism are different constructs. Enjoyment is about the work itself, and people still like the work. Burnout is about pace, and people are increasingly worn out by how much they have to do. Optimism is about where things are heading. You can love your craft, be worn out by how much of it you’re doing, and feel doubt about the future all at once.
How worried are you about layoffs?
This year, we also added a question to the survey: How worried are you about being laid off in the next year?
41.2% are at least moderately worried, including 19.9% who are “very” or “extremely” worried. 28% aren’t worried at all. So roughly four in 10 tech workers are carrying real job-security anxiety into their week—a sizable undercurrent.
What makes layoff worry worth its own question is how tightly it’s bound to everything else. Of all the things we measured, layoff worry is the single strongest correlate of career pessimism (r = –0.47). Nothing else tracks negative outlook as closely. When people are scared of losing their jobs, their optimism goes first.
We’ll come back to who is most worried later. It’s not who you might guess.
Takeaway 3: Tech workers wouldn’t recommend their own field
This year, we asked an NPS-like question about people’s careers and roles: On a scale of 0 to 10, how likely are you to recommend a career in your role to a friend starting out today?
More than half of working tech professionals would actively steer a newcomer away from the path they chose. That translates to an average NPS score of –39. Moreover, a third of the people who call themselves optimistic still wouldn’t recommend their own field.
The cleanest way to say it: “The water’s fine; don’t come in.” People have largely made peace with their own trajectory. They’ve got the skills, the relationships, and the seniority to ride it out. But they’ve lost faith that the on-ramp still works for someone behind them.
“I’m lucky I’m later in my career . . . AI can augment what I’ve built. I think I won’t be in a position to hire and mentor new PMs, but I’ll be safe. Which feels really crappy to say.”
“I’m at the point where I can just retire and choose not to, so I’m not worried about my own career. But I’m worried about the younger generations.”
The recommendation score varies enormously by role, and the spread is its own story.
Founders would (just barely) still wave you in. Designers and researchers very much would not. And the score climbs steadily with seniority: senior and staff-level individual contributors are the least likely to recommend their field (both at NPS –49), while VPs (–23) and founders (–5) are the most. The further up you’ve climbed, the more the ladder still looks worth it; the people on the rungs below are the ones telling others not to start the climb.
Takeaway 4: Productivity is up, but quality is questionable
Given the rising burnout, the layoff anxiety, the doom in the discourse, you’d expect tech workers to be rather sour on AI. They’re not.
At the individual level, the AI numbers are among the most positive in the survey. 82% say AI is already making them at least moderately better at their job, and nearly half (49.4%) say “very much” or “extremely.” 60% feel confident or ahead of their peers in AI skills, compared with just 22.5% who feel anxious or behind.
But then we looked closer at what “better at my job” means. When we asked people to describe in their own words how AI had changed their work, “better” turned out to mean producing more and faster, but not higher quality. The productivity gains are coupled with deep unease about the costs of leveraging AI.
“I can do more, faster, but not better.”
“Amplified and destabilized at the same time. We just set a new denominator for the job. And it moves higher and higher every month.”
And the cost isn’t only in the quality of outputs. A striking number of people described their focus, their judgment, and their thinking as suffering:
“I’m amplified, but my brain is rotting, and my work feels worse.”
“I feel like I don’t think hard enough anymore—I just follow Claude. I don’t fully understand what I merge.”
“I miss feeling smart and having aha moments. I miss talking [to] and brainstorming [with] humans instead of machines.”
The productivity gains are real, but the quality of the work and the sharpness of the person producing it are taking a hit. The bar keeps rising to match what AI makes possible, and a growing share of people feel that neither the output nor their own mind is keeping up.
Takeaway 5: The underlying fear is of being overworked
Respondents’ number-one worry about AI’s impact on their career is the squeeze—AI raised the bar for output, and the reward was . . . more output expected, for the same paycheck.
They’re scared that the work will get harder, faster, and cheaper, and that they’ll be expected to keep smiling through it.
It feels like the dominant narrative about AI and work has been about replacement: the robots are coming for your job. Clearly, that’s not what tech workers are most afraid of. “Losing my job to AI” came in near the bottom of the list, at 22%.
Remember the “AI is replacing parts of my job” question? Half of the respondents say it’s happening to at least a moderate extent. You’d expect that feeling to drive layoff anxiety, but it doesn’t. The correlation between “AI is taking over parts of my job” and “I’m worried about being laid off” is essentially zero (r = +0.05).
What people are actually worried about is being asked to do more for the same pay, and watching the quality of their work slip.
It shows up vividly in the open-ended answers:
“More and more work is being handed off to me because I can use AI to get it done. But that makes it impossible to keep up with quality standards and not burn out.”
“AI helps with the toil, but then it’s also an enabler to do even more toil.”
“When we automate intellectual tasks, we’ll have to do high-value creative or strategic work only—doing that eight hours a day is not realistic. I used to take rest during repetitive tasks.”
This might sound like it contradicts the layoff worry from earlier. It doesn’t. People fear layoffs, but they mostly don’t blame AI for them. What they fear from AI is being buried in more work.
Add this all up, and you get a workforce that’s more productive than ever but quietly dreading what comes next. The speed AI unlocked got plowed straight back into expectations. Every gain becomes the new baseline, and the people expected to hit it are running out of room to breathe.
Takeaway 6: Almost everyone is ambivalent
If there’s one feeling that defines tech workers’ relationship with AI in 2026, it isn’t excitement, and it isn’t fear. It’s both, at the same time.
We asked people to check off every emotion that described how they feel about AI in their work. Here’s the full list, in order:
The two leaders are unambiguously positive (curious, excited). But the next cluster (if we ignore “conflicted”) is made up of people who are overwhelmed and tired. People are curious and overwhelmed. Excited and tired. Only 33% feel “hopeful,” even though 64% feel “excited.” Excitement about the present is running well ahead of hope about where this all goes.
Nikhyl Singhal named this phenomenon “smiling exhaustion.” [ https://substack.com/redirect/6483d90e-cc61-40fa-abba-40b0cd9dce92?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] The burnout of a few years ago was grim—all overhead and no agency. Today’s is different. People are shipping again, compensation has climbed, and many roles seem reborn. The catch is that there’s no off-switch: the tempo is brutal, and the rules rewrite themselves every month. It’s relentless, but it can also be exhilarating.
You see this in that 51% explicitly selected “holding positive and negative feelings at once.” But that undercounts the real ambivalence. When we looked at who picked at least one positive and at least one negative emotion, the number jumped to 77%. The average respondent selected five or more emotions (one person selected 13). It’s a workforce in which three out of four individuals are carrying a complex set of emotions about work.
Takeaway 7: Designers and researchers are the most worried
If AI is dividing the workforce, the obvious question is: along what lines? Who’s getting amplified, and who’s getting left behind?
The clearest pattern is by role: designers and researchers are at the epicenter of AI anxiety across the board, while founders and executives are feeling the best. We measured the share of each role that landed in negative identity or emotional buckets, and the spread is stark:
Among researchers, 51% are “anxious about my job security,” versus 15% of founders. Among designers, 63% feel “overwhelmed by the pace of change” and 61% feel “tired,” the highest of any role. Researchers are among the most likely to fear “losing my job to AI” (36%, just behind Data/Analytics at 38%), and designers are the most likely to feel the comp squeeze (61% selected “expected to do more for the same compensation”). Both report the lowest willingness to recommend their field of any role, and designers, as we’ll see, report the worst-rated managers in the survey.
Last year, designers and researchers showed the largest negative sentiment shift of any group. A year later, they’re the most negative on nearly every measure we have.
As a researcher, I’m acutely aware of the years of insecurities plaguing the research community. The biggest discussions for us have always been about getting a seat at the table and democratizing research across other functions. Many now feel the seat is being pulled from under us, and the work is being democratized, not to other roles but to AI.
By level, the most identity-destabilized group is early-career ICs (27%). (This is a wrinkle we’ll untangle in a moment, because those same early-career folks are, paradoxically, among the more optimistic.)
And the bigger the company, the more likely its people are to feel adrift in the AI transition: 23% feel destabilized at 10,000-plus-person companies, versus 15% at companies of 1 to 10.
AI is hardest on people in creative and research roles, on the most junior people, and on people working at the largest companies.
Takeaway 8: Founders are the happiest people in tech, and small companies are the best places to work
For all the AI upheaval, some of last year’s biggest findings came back almost unchanged, and their persistence through such a turbulent year makes them all the more convincing. Founders are still the happiest people in tech, and smaller companies are still better places to work than big ones. Before you read those as good news, it’s worth saying what “best” means here. The whole industry is sitting on a high baseline of burnout and a rather negative career view, and the winners of this section are the people who feel a little less of it.
Founders aren’t just the happiest people in tech—on most measures, they’re genuinely happy.
Founders and executives top nearly every measure in the survey: the highest optimism, the highest job enjoyment, the lowest burnout, the lowest layoff worry, and the most excitement about AI. That gap between founders and execs versus everyone else holds up statistically. On career optimism, it measures d ≈ 0.56, a medium-size effect and the second-largest in the entire dataset, behind only the AI divide.
As we wrote last year, the likeliest explanation is ownership: founders have the most control over their own destiny, and control turns out to be one of the best buffers against everything else. 71% are optimistic about their careers, they enjoy their work more than any other role, and they’re the least worried about layoffs of any group.
Ownership has limits, though. Nearly half of founders (47%) are still at least moderately burned out, with 18% very or completely burned out, even with the most control and the most upside of anyone in tech. And when we asked whether they’d recommend their path to a newcomer, founders landed at an NPS of –5. That is far healthier than the field’s –39, but it’s still bad. Even the happiest people in tech come out slightly net-negative on telling someone to follow their path.
One caveat: we only surveyed people who are founders today. The ones whose startups failed aren’t represented, and most startups don’t make it. Keep that in mind before you quit to go start something!
Smaller companies are still better places to work than big ones.
Company size predicts sentiment with almost eerie consistency. Walk from the smallest companies to the largest, and every measure of well-being gets steadily worse as the company grows:
People at small companies are more optimistic, less burned out, less worried about layoffs, and even feel AI is helping them more, likely because they have more freedom to actually use it. The “big-company blues” we described last year have settled in.
Look at the absolute numbers, though, not just the slope. Even at the smallest companies, 42% of people are at least moderately burned out, and the would-recommend score never climbs out of the red, sitting at –28 at 1-to-10-person shops. Small companies are winning a race to the least bad.
Two smaller echoes of 2025:
Where you physically work still hardly matters. There are barely any differences between how fully remote, hybrid, and in-office workers feel. Hybrid workers come out marginally the happiest (and in-office workers rate their managers the worst), but the gaps are small, just as we found last year. Employment type tells a familiar story with one twist. Founders and the self-employed are the happiest and least burned out, while contractors and freelancers are an interesting split—they are among the least burned out (less of the grind) but the most worried about layoffs (no job security).
One wrinkle you may have noticed: the largest companies (10,000+) tick up slightly in optimism and down in burnout compared with the 5,001–10,000 tier, breaking the smooth gradient. But neither difference is statistically significant (5,001–10,000 is our smallest sample), so the line flattens at the top rather than reversing. The one measure that does keep climbing to the very top is layoff worry. Workers at 10,000-plus-person companies are the most worried of anyone in the survey.
Takeaway 9: Managers are still the biggest lever for happiness
One more finding held firm from last year, and it may be the most actionable of all. Manager effectiveness remains the strongest driver of burnout in the entire dataset (it beats role, company size, and AI sentiment), and one of the strongest drivers of everything else. The gradient is dramatic:
Workers with an extremely effective manager report roughly 65% higher job enjoyment and dramatically lower burnout than those with an ineffective one. Yet only 25.5% of tech workers rate their manager as highly effective, while 36.5% rate theirs as ineffective, numbers that have barely budged since last year. The most powerful retention lever in tech is also the most neglected. (Notably, the worst-rated managers cluster in Data/Analytics and Design. The latter is a double blow, since designers are also among the most AI-anxious.)
Takeaway 10: The industry is “chaotic”
We asked, “In a sentence, how would you describe the state of the tech industry right now?” About 70% of respondents answered, and the single most common theme, by a wide margin, was chaos: roughly three in 10 explicitly used words like change, chaotic, uncertain, unstable, and in flux. Another one in six described an industry moving too fast to keep up with—treadmills, hamster wheels, hurricanes, “drinking from a firehose.” After that came AI hype and bubble talk (12%) and then, finally, a note of excitement and opportunity (11%).
A few responses capture the sentiment better than any percentage can:
“We’re in the 2nd inning of a massive shift, and no one knows how it will end, but all you can do is keep taking at-bats.”
“It feels like working on pure software is like picking up pennies in front of a steamroller.”
“The industry feels like it has lost its center of gravity—replacing curiosity about customers with an obsession over AI, automation, and efficiency.”
The chaos plus hype is well-described in this quote from a senior PM:
“Manic. Half are out of touch, clinging to the bandwagon, making the problem worse by pouring into the overhype. The other half are exhausted by the first half.” —Senior IC PM
When we ran sentiment analysis on the chaos-related quotes, the split was nearly even: 37% positive, 37% negative, and 26% neutral. The dominant theme is disorientation, but the emotional charge is truly bimodal. The same churn reads as thrilling to one person and terrifying to the next.
We confirmed this by splitting the responses by who wrote them. Career optimists and career pessimists describe the same industry in opposite terms. Optimists reach for “exciting,” “transforming,” “opportunity,” “fast-moving.” Pessimists reach for “chaos,” “layoffs,” “greed,” “dystopia.” Same disruption, opposite forecasts: half the room is anxiously bracing for AI’s impact; the other half is eagerly leaning into the AI era.
Where do we go from here?
The 2026 workforce is more burned out and less optimistic than a year ago, splitting along the fault line of AI into those who are thriving and those who are struggling, and a large, ambivalent middle caught between. Tech workers are mostly afraid of being squeezed by their jobs and increasing productivity expectations, privately convinced the field is no longer worth recommending to newcomers, while individually still finding real power and even joy in the tools. It’s a complicated moment. It’s also not a hopeless one.
So here’s what the data suggests you can actually do about it.
If you’re an employee:
Find something impactful to do with AI—then go deep. The “amplified” are the people who found the two or three tasks where AI measurably changed their output and got very good at those. Trying to use AI for everything is how you end up overwhelmed and conflicted, not empowered.
Watch the squeeze. The biggest career risk is silently absorbing a higher and higher bar for the same pay until you’re burned out. Take our burnout test here [ https://substack.com/redirect/0af2df92-e4d7-4bda-b244-d12105968fe1?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], and if your output has doubled this year, talk to your manager about scope and compensation.
Your manager matters more than almost anything. A great manager is associated with about 65% higher job enjoyment and far less burnout. If you have one, protect that relationship. If you don’t, getting closer to a better one may be the highest-leverage career move available to you.
Consider a smaller company—or your own. Every well-being measure in this survey improves as company size shrinks, and founders are the happiest group in tech. More autonomy and control is, year after year, the most reliable buffer against burnout and pessimism we find.
If you’re early-career, find mentors. The rungs are disappearing, but strong mentorship remains highly effective. Seek the teams and managers who still invest in developing people. That investment is rarer and more valuable than it’s ever been.
If you lead a team or company:
Invest in managers—it’s still the best money you’ll spend. Only a quarter of tech workers rate their manager as highly effective, and nothing else in the data moves burnout, enjoyment, and retention as much. This was our top recommendation last year. It’s our top recommendation again.
Manage the squeeze. Your people can feel AI raising the bar, and they’re watching to see whether you turn productivity gains into impossible expectations or actual relief. The fastest way to end up with resentment on your team is to pocket the productivity and turn saved time into more work for them.
Don’t let the bottom rung rot. If AI is doing the entry-level work that juniors used to learn on, you’re optimizing this year’s output by starving next year’s senior talent. Be deliberate about how early-career people develop when the old apprenticeship tasks are gone.
Pay special attention to design and research. For two years running, people in these roles report the worst sentiment, the highest AI anxiety, and some of the worst-rated managers. That’s a retention problem and a signal worth understanding before it becomes an exodus.
Treat AI adoption as a sorting risk rather than a productivity win. The same technology is lifting one part of your workforce while destabilizing another. The companies that come out of this ahead will help support the destabilized group instead of leaving them behind.
The throughline, if there is one, is the same as last year’s: Having the most advanced AI or the fanciest offices won’t determine which organizations succeed. Remembering that there are people underneath all this change will—people who, right now, are excited and exhausted, hopeful and scared, often all at once. Those people are watching closely to see whether the future they’re helping to build will still have a place for them.
Huge thanks to the 5,920 tech professionals who shared how they’re really feeling. Your candor is what makes this possible, and it’ll help us keep tracking where the industry is headed. 🙏
Have a fulfilling and productive week.
Noam (and Lenny) 👋
Appendix: Who took this survey?
This year’s survey reached 5,920 tech professionals, of whom 5,332 are currently working. All analyses are based on currently employed tech workers.
Role. As with last year, this is a product-centric audience: Product Management 46.9%, Engineering 12.6%, Founder/Executive 9.1%, Design 7.9%, Operations 4.3%, Product Marketing 4.0%, Research 3.2%, Data/Analytics 2.9%, Sales/GTM 2.8%, with a long tail of other functions.
Seniority. A senior crowd: IC–Senior 28.9%, IC–Staff/Principal 19.9%, Director 15.4%, Manager 12.1%, Founder/Exec 10.8%, VP+ 7.4%, and IC–Early career 5.5%. Roughly 54% individual contributors and 46% managers and above.
Company size. A fairly even spread, from 1–10-person startups (11.1%) up through 10,000-plus-person enterprises (18.0%), with the middle bands well represented.
Work setup. Fully remote 47.0%, hybrid 43.0%, fully in-office just 10.0%.
A methodological note for the careful reader: We made year-over-year comparisons only for questions whose wording matched across years. We redesigned much of the survey this year to focus on AI, which means a few 2025 themes (engagement, belonging, quitting intentions, career clarity) aren’t measured here, while others (layoff worry, the AI block, the career-recommendation score) are new. We also didn’t collect age, tenure, or geography this year, so when we discuss career stage, we’re using job level as a proxy.
If you’re finding this newsletter valuable, share it with a friend, and consider subscribing if you haven’t already. There are group discounts [ https://substack.com/redirect/3baec419-8c63-422a-89ed-83d956f849b5?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], gift options [ https://substack.com/redirect/7a0d4066-d123-45b8-b401-bf0d6409126e?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], and referral bonuses [ https://substack.com/redirect/277fe6e4-4616-4ec1-8899-5badd3a53883?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] available.
Sincerely,
Lenny 👋
Unsubscribe https://substack.com/redirect/2/eyJlIjoiaHR0cHM6Ly93d3cubGVubnlzbmV3c2xldHRlci5jb20vYWN0aW9uL2Rpc2FibGVfZW1haWw_dG9rZW49ZXlKMWMyVnlYMmxrSWpvME1qWTFNVFV3TkRBc0luQnZjM1JmYVdRaU9qRTVOVFUxTnpnNU1pd2lhV0YwSWpveE56Z3pORE13TlRreExDSmxlSEFpT2pFNE1UUTVOalkxT1RFc0ltbHpjeUk2SW5CMVlpMHhNRGcwTlNJc0luTjFZaUk2SW1ScGMyRmliR1ZmWlcxaGFXd2lmUS5YNlNOdm1HaEtUTndXbHBiejdDYnR3UGlieVF6NS1IcjktSmNlc3g2UFMwIiwicCI6MTk1NTU3ODkyLCJzIjoxMDg0NSwiZiI6dHJ1ZSwidSI6NDI2NTE1MDQwLCJpYXQiOjE3ODM0MzA1OTEsImV4cCI6MjA5OTAwNjU5MSwiaXNzIjoicHViLTAiLCJzdWIiOiJsaW5rLXJlZGlyZWN0In0.Cxtyx4_7zQ_xOeUUMWGlIEGpuZm3tMTL3WyfAShjycI?
View Email
How tech workers are feeling in 2026: a workforce splitting in two
lenny@substack.com7/7/2026
SubstackView this post on the web at https://www.lennysnewsletter.com/cp/204728693
Unsubscribe https://substack.com/redirect/2/eyJlIjoiaHR0cHM6Ly93d3cubGVubnlzbmV3c2xldHRlci5jb20vYWN0aW9uL2Rpc2FibGVfZW1haWw_dG9rZW49ZXlKMWMyVnlYMmxrSWpvME1qWTFNVFV3TkRBc0luQnZjM1JmYVdRaU9qSXdORGN5T0RZNU15d2lhV0YwSWpveE56Z3pNREU1TnpJM0xDSmxlSEFpT2pFNE1UUTFOVFUzTWpjc0ltbHpjeUk2SW5CMVlpMHhNRGcwTlNJc0luTjFZaUk2SW1ScGMyRmliR1ZmWlcxaGFXd2lmUS5ZVWYwRE1pRzhZWGFYNDZ3cHhraDczQUdaLVBJcWJ1TlMzQVBOVmNCenB3IiwicCI6MjA0NzI4NjkzLCJzIjoxMDg0NSwiZiI6dHJ1ZSwidSI6NDI2NTE1MDQwLCJpYXQiOjE3ODMwMTk3MjcsImV4cCI6MjA5ODU5NTcyNywiaXNzIjoicHViLTAiLCJzdWIiOiJsaW5rLXJlZGlyZWN0In0.ZYGgeoOkqDGg6ovvkN6-Slc__qm0zpJQb6XEH1qQbEo?
View Email
Please stop the AI Confidence Theater
lenny@substack.com7/2/2026
SubstackView this post on the web at https://www.lennysnewsletter.com/p/how-top-pms-increase-their-leverage
👋 Hey there, I’m Lenny. Each week, I answer reader questions about building product, driving growth, and accelerating your career. For more: Lenny’s Podcast [ https://substack.com/redirect/aa44e7cd-6e05-457f-818a-067b6b837baf?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] | Lennybot [ https://substack.com/redirect/47c0d277-3581-49af-a189-e2a6c688faa5?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] | How I AI [ https://substack.com/redirect/8d8c497e-bf7e-4e8c-bbf1-08559f83602e?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] | My favorite AI/PM courses [ https://substack.com/redirect/c5d6c19a-dab7-459d-8ef0-a155ce60ca4c?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], public speaking course [ https://substack.com/redirect/96327313-d699-4698-bf9b-8e0e4b486207?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], and interview prep copilot [ https://substack.com/redirect/e9f8fe15-2389-43d6-8107-66da1af22260?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
P.S. Get a full free year of Google AI, Cursor, Lovable, Notion, Manus, Replit, Gamma, n8n, Canva, ElevenLabs, Factory, Wispr Flow, Fin, Supabase, Bolt, Linear, PostHog, Framer, Railway, Granola, Warp, Gumloop, Magic Patterns, Mobbin, Stripe Atlas, and ChatPRD, by becoming an Insider subscriber [ https://substack.com/redirect/3fdde2ba-83d3-4a57-813c-11588380b59f?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]. Yes, this is for real [ https://substack.com/redirect/1d15bd90-1d7e-49b7-addd-326791ffd77b?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ].
For years, the PM job drifted toward coordinating and aligning people. That version of the role is fading. Today, the best PMs at the best companies are prototyping with real code, querying data conversationally with MCP, confidently running coding AI agents, and finding countless ways to increase their leverage with AI.
To help you navigate this shift, I’m excited to announce that I’ve co-developed a course with my frequent collaborator and new Head of Education, Colin Matthews [ https://substack.com/redirect/5c8290f7-7f40-45f0-b306-0568759119ed?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]. It’s called Become an AI-Native Builder [ https://substack.com/redirect/d9bb9fb6-ea65-402d-a20c-e795560bd96c?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], and Colin will teach you how to best use the latest AI tools—including Codex, Claude Code, Cursor, and many of the Product Pass [ https://substack.com/redirect/1d15bd90-1d7e-49b7-addd-326791ffd77b?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] products—in your day-to-day work as a PM. You’ll use skills and MCPs to support discovery, create prototypes using your real codebase, ship changes to production using GitHub, and set up evals to automate and improve the quality of your work. This is the course I’ve always wished existed. And it’s not just for PMs. It’s great for designers, ops, researchers, sales, and basically anyone who’s non-technical and wants to get their hands dirty.
The first cohort [ https://substack.com/redirect/d9bb9fb6-ea65-402d-a20c-e795560bd96c?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] kicks off on July 13th. If you’re a Lenny’s Newsletter annual subscriber you’ll get $600 off (and Insiders get $1,000 off). Grab your discount code here [ https://substack.com/redirect/b9de9839-5326-48ab-9e05-52ccb1e83e0f?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] and sign up today [ https://substack.com/redirect/d9bb9fb6-ea65-402d-a20c-e795560bd96c?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ].
In addition to this course, Colin is hosting a handful of free [ https://substack.com/redirect/ed766688-d645-4797-9fd2-8f0c17ebea78?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] workshops [ https://substack.com/redirect/ed766688-d645-4797-9fd2-8f0c17ebea78?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] with leaders from OpenAI, Cursor, Linear, Replit, and Lovable. These will be live and hands-on, and you’ll learn and practice new skills alongside other people in the trenches. These workshops are exclusive to paid Lenny’s Newsletter subscribers, and you can sign up for them here [ https://substack.com/redirect/ed766688-d645-4797-9fd2-8f0c17ebea78?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ].
Colin is one of the most talented instructors of AI that I’ve come across. We’ve done four guest posts together (one is my third-most-popular post of all time) and, like me, he’s low on hype and high on pragmatic advice. He’s taught AI and other technical skills to tens of thousands of PMs at leading companies like OpenAI, Google, Stripe, Figma, Microsoft, and more. He’s a longtime product leader, a founder, and has shipped more than 10 SaaS products solo.
To mark the launch of this course, Colin wrote a guest post that will help you understand what’s possible with AI right now and where you stand on the “ladders of leverage.”
Let’s get into it.
I’ve trained over 30,000 PMs on how to integrate AI into their workflows. Early this year, I noticed a shift. Whereas before I heard from executives that they expected teams to be using AI for just basic prototyping and general productivity, now they’re increasingly looking for their employees to use AI to complete entire tasks. After building bespoke training programs to level up product and design ICs across industries like healthcare, legal, and streaming, I saw two main gaps: knowing what level of AI to reach for and having the technical skills to leverage AI tools to their fullest.
I wanted to share a forward-looking framework on how the most AI-native PMs are operating in mid-2026, and how you can create much more leverage for yourself with AI.
Think of this framework as three ladders, each for a different type of leverage that AI can give you.
Personal leverage helps you check items off your own to-do list at work. Product leverage accelerates your ability to ship the right things more quickly. And systems leverage helps build repeatable steps to consistently outsource work to AI and get high-quality results.
As you ascend each ladder rung, you get an order of magnitude more leverage. On the first rung, you use AI for assistance in your own work. On the second rung, you pass tasks to AI and review the output. At the top of the ladder, AI completes multi-step tasks and checks its own results. You will always apply some level of review at the end, but increasing leverage frees you up for other work.
Not every task, workflow, or company demands that you move up to the highest rung to get the most out of AI. The right rung on each ladder is about the best use of AI for the work in front of you.
I’ll walk through all three ladders, with examples you can start using today. Let’s get into it.
The personal leverage ladder
This is the most common way we all use AI at work: drafting docs, researching, or creating small artifacts. Most PMs are already pretty capable here, but it’s worth detailing the rungs so that you can see where you’re at and where you might go.
Rung 1: You use AI to write text. You’re using AI to help you with PRDs, Jira tickets, emails, etc. You then copy and paste answers into other tools. Most people are at this rung, or even lower. Don’t feel bad if you’re hanging out here. There’s so much opportunity!
Rung 2: You use AI to create artifacts. Think slides, basic Excel models, or small prototypes. Instead of generating text for you to copy, AI generates the actual artifact.
Rung 3: You get AI to complete a full to-do item for you. You’ve connected your LLM to external products like Amplitude, Google Drive, Notion, and Canva so it can pull and push information as needed. You run a prompt or skill to complete a task you might have handed off to a colleague before, like reading through customer support tickets or analyzing A/B test results.
Let’s walk through an example of each rung to illustrate baseline expectations.
At the beginning, you’re simply talking to the AI. For example, if I wanted to create a PRD, I might ask Claude to help me write it with a prompt like this:
The AI has very little context on your company or what a good PRD looks like. You’ll likely talk back and forth until you get a good enough result, then copy-paste to Google Docs or Word to improve it before sharing with your team.
Next is getting the AI to do work instead of just helping you do the work. Continuing with the last example, you could have Claude generate a financial model that shows the cost of hosting an agent yourself vs. using a managed service like Vercel.
Here’s a prompt I recently used:
Create a model that represents costs if we build and host ourselves vs. using managed agents. Do research on the engineering time saved and the compute costs in self-hosted vs. managed. Look at other vendors, like Cloudflare, Vercel, or E2B that provide sandboxes for agents for pricing. Demonstrate both the cost of the pilot and the cost at scale in the model, assuming we have 5M+ agent instances running annually (where an agent instance is per hour).
And here’s what the resulting model looks like:
As mentioned, you should expect the output to need significant revision at this rung, but it’s a step forward from copy-pasting text from AI into a separate document.
You’re at the highest rung of personal leverage if you are able to delegate complete to-do items to AI. To illustrate this, I’ll use a fictional product called Stride. Stride is a Strava clone, where athletes can share their performance for running, swimming, and other activities. Let’s say I wanted to do a retention analysis of users who share their exercises with an attached photo, and compare that against the cohort who don’t share photos. To complete this task, I’ll connect my LLM of choice (Claude) to my product analytics software (PostHog) and give it instructions to run this analysis for me. This was my prompt:
Use PostHog to check if users who use social share features have a higher 30d retention than those who don’t. Show me an html doc as a final output visualizing cohorts and any other useful data. Cite all your sources so I can validate.
And here’s the result:
In the past, this would have been a task you’d fit in between meetings. Instead, you’re handing it off to an LLM to complete end-to-end. I’d recommend including “cite your sources” so you can easily validate if the output is correct. In this case, Claude provides links directly to the source data in PostHog.
Pro tip: To allow models to complete tasks for you (and thus move to this rung in your personal work), you’ll need to connect your LLM to the products you use frequently via MCP. Claude Code, Codex, and Cursor can all connect to tools like Figma, Amplitude, PostHog, Pendo, and more via MCP. This may sound complicated, but it’s really easy to do, and once you create this connection, you’ll never have to touch it again. Simply navigate to your product’s connectors marketplace and add your tools (Claude [ https://substack.com/redirect/25551932-2333-4ccc-8302-17a47fd372b2?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], ChatGPT [ https://substack.com/redirect/8f2cb411-23c0-4e27-b700-147b27078431?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], Gemini [ https://substack.com/redirect/fc813c86-831a-4c88-abff-851c88a1ff3f?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]).
Once you have your connectors set up, try completing a common task using your AI, like:
Analyzing how a launch went by reviewing recent customer tickets and online sentiment
Checking how many users actually use a feature through product analytics events
Summarizing a recording from a customer call and creating a prototype based on their feedback
Updating your next sprint based on a change in roadmap priorities
You’ll likely find the results disappointing at first, but that’s just because the model doesn’t know how to meet your standards yet. Continue iterating with the model until you have a good result, then lock in the workflow by creating a skill—just ask your LLM to create one in the same chat you completed the task in.
You can repeat this workflow to get reasonable first drafts for almost anything: PRDs, roadmaps, marketing assets, survey analysis, prototypes, Figma mocks, and more. I totally acknowledge that the quality may not be perfect, but we’ll come back to that when we talk about systems leverage.
The product leverage ladder
Product leverage closes the gap between what you want to build and what you can ship, even without strong design or engineering chops. The way to leverage AI for this ladder breaks down into three rungs:
Rung 1: You create web-based prototypes. These communicate your ideas better than docs, but the prototype itself doesn’t have any value beyond communication. And your prototype’s code is independent from your product—it doesn’t use your existing codebase.
Rung 2: You create code-based prototypes. Claude Code or Codex accesses your real codebase as the context for generating prototypes, instead of screenshots or complex prompts.
Rung 3: You get an agent to ship changes to production as pull requests. An engineer picks up the PR, reviews, and merges your code into the product.
Let’s spend a bit more time with each of these.
Using AI tools like Lovable, Replit, and Magic Patterns is an amazing way to quickly and easily create a prototype. You can use this to share a concept or design with stakeholders, customers, or internal team members, allowing you to validate whether your solution is usable and solves the customer problem faster than ever.
Let’s revisit Stride as an example. Here’s what the profile page currently looks like:
Customers have been complaining that they don’t have clear cancellation paths and are confused about their subscription status after a free trial. You can use AI prototyping to create a quick mock to test with customers and stakeholders if one or more of your solutions address this problem:
This helps get to the right solution by testing more concepts faster, but typically the underlying code doesn’t have any value. Web AI prototyping tools have limited context on our real components, pages, and data models, so this prototype is removed from reality. That means that it will take more work to translate the tested prototype to real code.
The next rung up is to ask AI to prototype with your real product. This does not require running the full product on your laptop—or an expert-level coding ability—but you will need some technical skills. First, use a product like Claude Code or Codex to write code and run your app. Second, you’ll need a codebase that contains your UI but not your full backend; more on that later.
You can create the same prototype, this time asking Claude Code or Codex to use your existing codebase:
This time, the cancellation flow is added to the existing settings page, uses real components, and follows the design patterns of the actual product.
To create a codebase or repo that’s easy to use and doesn’t require running the full backend, pair with an engineer and have them use a prompt like this on your main codebase:
Create a new repo that contains all of the base UI elements, styles, routes, pages, and components for [list parts of the product you want included]. Create a mock data store that mimics the API data model and is stored locally. I should be able to run the resulting repo without any environment variables or backend services.
Once complete, clone the new repo to your computer. You should have an easy-to-run version of your UI that you can’t accidentally mess up. Sometimes your engineer will tell you this process is more complicated to get running than a simple prompt. It is very much worth the effort to build prototypes on your real styles and components, so do your best to get over the hump!
The last rung in product leverage is getting an agent to ship code to production. This is a great example of where your technical judgment as a PM is critical. It’s possible that your billing change is only in the UI, and all backend APIs, data elements, and events already exist. It’s also possible that this would require new infrastructure or integrations with another team to ship.
As a PM, it does not make sense to spend time being a worse engineer than the rest of your team. Knowing when you should write a doc, ship a prototype, or create a PR is as important as the technical ability to complete these tasks. PRs are great for copy changes, small UI/UX tweaks, and changes to views that use existing backend code.
The systems leverage ladder
Unsubscribe https://substack.com/redirect/2/eyJlIjoiaHR0cHM6Ly93d3cubGVubnlzbmV3c2xldHRlci5jb20vYWN0aW9uL2Rpc2FibGVfZW1haWw_dG9rZW49ZXlKMWMyVnlYMmxrSWpvME1qWTFNVFV3TkRBc0luQnZjM1JmYVdRaU9qSXdNemN6TURZek9Td2lhV0YwSWpveE56Z3lPREkzTVRNMExDSmxlSEFpT2pFNE1UUXpOak14TXpRc0ltbHpjeUk2SW5CMVlpMHhNRGcwTlNJc0luTjFZaUk2SW1ScGMyRmliR1ZmWlcxaGFXd2lmUS5BSXBYZGpWd3psRWlqdzA5d3BManJ1WTNIdjZPM012T1czS2gzMHNWaElnIiwicCI6MjAzNzMwNjM5LCJzIjoxMDg0NSwiZiI6dHJ1ZSwidSI6NDI2NTE1MDQwLCJpYXQiOjE3ODI4MjcxMzQsImV4cCI6MjA5ODQwMzEzNCwiaXNzIjoicHViLTAiLCJzdWIiOiJsaW5rLXJlZGlyZWN0In0.uQNZyTsFmUFBRQtx1xdBELToF-g0fSGRLyoW3XYcrHU?
View Email
How top PMs increase their leverage with AI
lenny@substack.com6/30/2026
SubstackView this post on the web at https://www.lennysnewsletter.com/p/openai-codex-lead-on-the-new-shape
Andrew Ambrosino leads development of the Codex desktop app at OpenAI. Nearly 100% of OpenAI employees—not just engineers—now use Codex weekly. A lifelong builder with a background spanning engineering, design, product management, and founding companies, he is now responsible for turning the Codex desktop experience into what he calls “the best desktop app that has ever existed, full stop.”
Listen on YouTube [ https://substack.com/redirect/42edae09-23f7-49d6-87f2-0f414b17d669?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], Spotify [ https://substack.com/redirect/c2d5e3b1-9bcc-4e6d-82ec-f56e9b03cf51?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], and Apple Podcasts [ https://substack.com/redirect/76ce00e4-7548-4b0c-8eda-c184eafcb90f?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
In our in-depth conversation, we discuss:
Why AI has completely flipped the product development process
What “taste” really means as a professional skill, and why it is emerging as the most valuable capability in an AI-first workplace
Why Andrew believes the Codex app would have failed if they launched it last November (vs. in February)
The “zone defense” model for how product managers at OpenAI operate when everyone can build anything
How roles are collapsed on Andrew’s team, and why eliminating the concept of roles entirely is a big mistake
How Andrew uses Codex to run his own workflows
The vision for a home base that coordinates work across ChatGPT, Codex, and the tools people already use.
Brought to you by:
WorkOS [ https://substack.com/redirect/648cc66d-aade-4386-bd6c-161b40ff0879?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]—Make your app enterprise-ready, with SSO, SCIM, RBAC, and more
Mercury [ https://substack.com/redirect/8913172b-0c3f-410b-beb9-c4737ebaaf74?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]—Radically different banking, now with Command
Where to find Andrew Ambrosino:
• X: https://x.com/ajambrosino [ https://substack.com/redirect/ab3b9164-387c-42b6-8d1b-751e16497cca?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• LinkedIn: https://www.linkedin.com/in/ajambrosino [ https://substack.com/redirect/9d1393d4-eba5-40bb-8df6-a4d717706c1a?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Website: https://ambrosino.io [ https://substack.com/redirect/8f892144-8fd8-45ae-9a32-867d1bce48cf?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Referenced:
• Codex: chatgpt.com/codex [ https://substack.com/redirect/5b3ff210-6dde-41d8-91cd-1d94799551c1?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• The Primal Mark: How the Beginning Shapes the End in the Development of Creative Ideas: https://www.gsb.stanford.edu/faculty-research/publications/primal-mark-how-beginning-shapes-end-development-creative-ideas [ https://substack.com/redirect/d05fb32f-3530-409f-bbae-767f5dbf9feb?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Linear: https://linear.app [ https://substack.com/redirect/ea23346f-3b1a-4bf8-93c2-bce774692fc6?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• “Taste” is not just taste in aesthetics: https://x.com/thenanyu/status/2067327619897446721 [ https://substack.com/redirect/142bd037-1300-46c1-ba8b-a783af845e0c?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Linear’s secret to building beloved B2B products | Nan Yu (Head of Product): https://www.lennysnewsletter.com/p/linears-secret-to-building-beloved-b2b-products-nan-yu [ https://substack.com/redirect/cc1f3ef4-fa79-41ec-9743-1f8fd542beac?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Paul Graham’s website: https://paulgraham.com [ https://substack.com/redirect/eac0136f-637a-4e39-8f8a-b2ac7609750c?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• The design process is dead. Here’s what’s replacing it. | Jenny Wen (head of design at Claude): https://www.lennysnewsletter.com/p/the-design-process-is-dead [ https://substack.com/redirect/bfdfc345-3f6c-48e2-9e41-c8b5cbf4b093?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• The case study factory: https://essays.uxdesign.cc/case-study-factory [ https://substack.com/redirect/bb3c6c79-6ab5-450c-9ab8-76a231209277?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Why humans are AI’s biggest bottleneck (and what’s coming in 2026) | Alexander Embiricos (OpenAI Codex Product Lead): https://www.lennysnewsletter.com/p/why-humans-are-ais-biggest-bottleneck [ https://substack.com/redirect/fcb12580-057a-4c8a-bf25-9b60e87e5faf?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• OpenClaw: https://openclaw.ai [ https://substack.com/redirect/e4b9438b-80f4-4db9-b655-2d88539a6d53?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• OpenClaw: The complete guide to building, training, and living with your personal AI agent: https://www.lennysnewsletter.com/p/openclaw-the-complete-guide-to-building [ https://substack.com/redirect/24c15f8c-8a21-4237-a257-1707618181aa?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• From skeptic to true believer: How OpenClaw changed my life | Claire Vo: https://www.lennysnewsletter.com/p/how-openclaw-changed-my-life-claire-vo [ https://substack.com/redirect/a80a7b81-09b7-4159-9950-62485d9d23a5?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• The Codex feature that works while you sleep: https://www.lennysnewsletter.com/p/the-codex-feature-that-works-while [ https://substack.com/redirect/53f93c0e-a38e-4829-84a4-63f4a1abfe11?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• The AI paradox: More automation, more humans, more work | Dan Shipper: https://www.lennysnewsletter.com/p/the-ai-paradox-dan-shipper [ https://substack.com/redirect/c46e8a9f-9794-46a2-a18b-b20f28d772eb?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Atlas: https://chatgpt.com/atlas [ https://substack.com/redirect/68c95f5c-7da0-4544-8bbb-3be33f1ed7f1?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Anthropic: https://www.anthropic.com [ https://substack.com/redirect/95080dde-3b32-476e-93b6-5a4370eee110?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Adobe Premiere: https://www.adobe.com/products/premiere [ https://substack.com/redirect/e83e748b-5e8a-4c6f-842c-8111aa753779?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• The Magic School Bus Rides Again: https://www.netflix.com/title/80108373 [ https://substack.com/redirect/3205fc74-b960-4daf-861a-786e95f17abd?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Recommended books:
• The Gruffalo: https://www.amazon.com/Gruffalo-Julia-Donaldson/dp/0803730470 [ https://substack.com/redirect/bf0f5658-2904-466e-a3d8-88e3184265a1?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• The Big Orange Splot: https://www.amazon.com/Big-Orange-Splot-Manus-Pinkwater/dp/0590445103 [ https://substack.com/redirect/1a672e86-8a96-4252-b9a7-ad925f39a3a3?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Production and marketing by https://penname.co/ [ https://substack.com/redirect/02b5dbe2-2ab9-4ff8-9429-6888b4c33dce?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com [ mailto:podcast@lennyrachitsky.com ].
Lenny may be an investor in the companies discussed.
My biggest takeaways from this conversation:...
Unsubscribe https://substack.com/redirect/2/eyJlIjoiaHR0cHM6Ly93d3cubGVubnlzbmV3c2xldHRlci5jb20vYWN0aW9uL2Rpc2FibGVfZW1haWw_dG9rZW49ZXlKMWMyVnlYMmxrSWpvME1qWTFNVFV3TkRBc0luQnZjM1JmYVdRaU9qSXdNamMyT1RneU1Dd2lhV0YwSWpveE56Z3lOalV3TnpjM0xDSmxlSEFpT2pFNE1UUXhPRFkzTnpjc0ltbHpjeUk2SW5CMVlpMHhNRGcwTlNJc0luTjFZaUk2SW1ScGMyRmliR1ZmWlcxaGFXd2lmUS5wN2VieGliMmFjZGwyVnhVUGlCN0VnTGMwYV8tVS1iUnR4OE5aMW51dk93IiwicCI6MjAyNzY5ODIwLCJzIjoxMDg0NSwiZiI6dHJ1ZSwidSI6NDI2NTE1MDQwLCJpYXQiOjE3ODI2NTA3NzcsImV4cCI6MjA5ODIyNjc3NywiaXNzIjoicHViLTAiLCJzdWIiOiJsaW5rLXJlZGlyZWN0In0.iY_ChSrNfedPyY4RmKMo93aJy-K--KNxAwig-Y5Vc0E?
View Email
OpenAI Codex lead on the new shape of product work | Andrew Ambrosino
lenny@substack.com6/28/2026
SubstackView this post on the web at https://www.lennysnewsletter.com/cp/203444316
Unsubscribe https://substack.com/redirect/2/eyJlIjoiaHR0cHM6Ly93d3cubGVubnlzbmV3c2xldHRlci5jb20vYWN0aW9uL2Rpc2FibGVfZW1haWw_dG9rZW49ZXlKMWMyVnlYMmxrSWpvME1qWTFNVFV3TkRBc0luQnZjM1JmYVdRaU9qSXdNelEwTkRNeE5pd2lhV0YwSWpveE56Z3lNekkyTlRFeExDSmxlSEFpT2pFNE1UTTROakkxTVRFc0ltbHpjeUk2SW5CMVlpMHhNRGcwTlNJc0luTjFZaUk2SW1ScGMyRmliR1ZmWlcxaGFXd2lmUS54SU4xT3hfTFV6OEFtbTN2bWdRSnhzd1QzalJTYU9wZEVONm90OWhKdFVvIiwicCI6MjAzNDQ0MzE2LCJzIjoxMDg0NSwiZiI6dHJ1ZSwidSI6NDI2NTE1MDQwLCJpYXQiOjE3ODIzMjY1MTEsImV4cCI6MjA5NzkwMjUxMSwiaXNzIjoicHViLTAiLCJzdWIiOiJsaW5rLXJlZGlyZWN0In0.AjdOdwRtmj2yUkJxpxg1ydJEbqUTGYfi9oO8TapaWsM?
View Email
How Meta Is Reinventing Product Management
lenny@substack.com6/24/2026
SubstackView this post on the web at https://www.lennysnewsletter.com/p/the-new-inner-game-your-unfair-advantage
👋 Hey there, I’m Lenny. Each week, I answer reader questions about building product, driving growth, and accelerating your career. For more: Lenny’s Podcast [ https://substack.com/redirect/43ddbc7e-6b8f-44bf-ade7-dd7ebeeada05?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] | Lennybot [ https://substack.com/redirect/dbe93825-7bae-43a8-80ac-259590be7344?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] | How I AI [ https://substack.com/redirect/37b470a5-451b-4cad-ba72-7bf3dec14a29?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] | My favorite AI/PM courses [ https://substack.com/redirect/7b1e8c99-e93d-4e0a-a42c-a7fa826adf95?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], public speaking course [ https://substack.com/redirect/2f99b304-5fcc-4fcc-bfb5-a191f8d17fc3?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], and interview prep copilot [ https://substack.com/redirect/da6e7a22-8117-47cf-8c00-ffaf6282d7b8?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
P.S. Get a full free year of Google AI, Cursor, Lovable, Notion, Manus, Replit, Gamma, n8n, Canva, ElevenLabs, Factory, Wispr Flow, Fin, Supabase, Bolt, Linear, PostHog, Framer, Railway, Granola, Warp, Gumloop, Magic Patterns, Mobbin, Stripe Atlas, and ChatPRD, by becoming an Insider subscriber [ https://substack.com/redirect/aad0d1ee-b679-46f9-a2db-64a1d68ac72b?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]. Yes, this is for real [ https://substack.com/redirect/f9afd387-5f21-4ff8-a282-bc0a01fda8c2?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ].
Joe Hudson is one of the most sought-after executive coaches in Silicon Valley, working with influential leaders like Sam Altman (OpenAI CEO) and founders and execs across Apple, Google, X, and more. He now spends much of his time coaching the research team at OpenAI and, from that inside perspective, has observed that the skills for success in AI-forward environments aren’t the ones you’d expect. Below, Joe explains and helps you prepare for what’s ahead.
For more from Joe, check out his Substack [ https://substack.com/redirect/285517b3-c798-4dd4-a396-67bbb51eb2c0?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], Leadership Newsletter [ https://substack.com/redirect/8da5d869-cc26-4002-8713-4e25e6c70989?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], and Connection Course [ https://substack.com/redirect/f1c850e0-4650-4ce0-8928-8312ef521fc5?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]. You can also find him on X [ https://substack.com/redirect/e73c541f-dae5-4e6c-890f-e0161007b0cb?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] and LinkedIn [ https://substack.com/redirect/2ca91c40-7ed3-41b1-90dc-f4c73961e553?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]. And don’t miss my podcast conversation [ https://substack.com/redirect/aab2f7c8-80a1-4620-96b1-4340ce75dd7e?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] with him from last year!
Almost everyone I talk to is scared of the same thing.
“I’m going to get replaced by AI.”
“I can’t keep up with how fast everything is changing.”
“I’m going to end up in the permanent underclass.”
I hear this from senior VPs at Fortune 500 companies, and I hear it from people working inside the frontier AI labs. None of these fears are unfounded. The ground really is moving. Most of what you and I have been trained to do all our lives is being commoditized in the same way machines commoditized physical labor a century ago. The traditional skills we’ve optimized for—effort and knowledge—are becoming the exact two things AI does best.
But the trouble with fear is that it’s a terrible planner. Fear creates binary thinking and false ends, and braces us for worst-case scenarios, rather than preparing us for an unknown future.
Think about all the hard conversations you’ve had with your boss or investor. You rehearsed them in the shower. You ran every way they could go sideways. Then you actually had the conversation. How many times did it go exactly as scripted? So many of those rehearsals prepared you for conversations that never happened.
That’s where most of us are right now with AI. We’re afraid and rehearsing for the wrong conversations. Meanwhile, the skills that will actually decide whether we thrive aren’t even on our radar.
I spend my weeks coaching the people building this technology at OpenAI, and the courses I teach on emotional clarity at the Art of Accomplishment are full of folks from every top frontier AI lab. I have an unusual front-row seat to what’s coming because people in these environments are already operating in the future.
What I’ve seen is that those who thrive in these AI-pilled environments can stay in difficult conversations, not turn on themselves—or each other—when things get hard, and keep going in the midst of failure.
That’s the heart of what I want to show you, and it’s the opposite of what fear pushes you toward. Your unfair advantage in the age of AI comes from emotional clarity: the ability to feel what you’re feeling without being run by it. When knowledge and effort are nearly free, emotional clarity is scarce. But luckily, it’s a skill that can be learned.
In this post, I’m going to give you ways to measure your readiness around emotional clarity and hand you the specific methods to train for future success, for yourself and for your team.
How AI is changing work: the NBA-ification of teams
AI is increasingly amplifying what one person [ https://substack.com/redirect/d42c5a2e-bded-4a6c-ac29-32c7d1a2b43e?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] can accomplish, which means teams will start looking less like factories and more like NBA rosters: organizations will flatten and headcount will shrink, with far more capital riding on each person and their skills.
This is already happening in AI-forward tech companies like Anthropic [ https://substack.com/redirect/348cda01-a6df-4dbb-bf9e-d1ce491fce1c?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], Amazon [ https://substack.com/redirect/7dc2cb2c-ebc9-4d34-849f-56eb4993e48d?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], Shopify [ https://substack.com/redirect/cb783987-b738-4ede-9181-ed5c7f0335a8?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], Coinbase [ https://substack.com/redirect/b2ea1f02-d846-4d3b-9e91-41bd742f966c?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], and Block [ https://substack.com/redirect/f948851f-9cb9-46a4-954c-3ae9b9a7e64e?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], which are flattening their orgs and even creating “player-coach” roles. I also watch this happen every week inside the labs.
On an NBA team (and in these labs), knowledge isn’t the moat. You don’t win with the player who’s memorized the most plays or knows the most about shooting baskets. You win based on who makes the right read with two seconds on the clock, who can stay composed when the game gets physical, and who makes everyone around them better instead of worse to play with.
The result is a drastic change in what makes a team great. Talent and chemistry have always mattered, but when each person is amplified by AI, every decision, every pivot, and every bit of friction compounds. When an individual can face hard things, they accomplish a lot. But a team that can face hard things together moves exponentially faster. How to develop those emotional skills is what the rest of this piece is about.
The new inner game: the “wisdom stack” that will set you apart
What’s pulling people ahead in the age of AI is a set of capabilities most of us never thought of as skills at all. After seeing the same qualities consistently show up inside the labs, I’ve distilled them into four traits and called them the wisdom stack:
Discernment
“In conflict we trust”
Willingness to fail
Positive self-talk
1. Discernment
As AI increasingly takes over the doing, the critical work left for humans is the higher-level deciding: what to build, what to leave behind, and when to change course.
LLMs can advise you on what decision to make, but no model can feel the subtle tension in a meeting room or register your body’s signal when something’s off. Only you have that data, and that makes discernment more valuable than ever. And what most people don’t realize is that what often degrades decision-making is a lack of emotional clarity.
You’ve probably been told that better choices come from more data or sharper reasoning, but neuroscience shows us [ https://substack.com/redirect/e2a9f73d-e446-41bf-8097-8c47270b7a2f?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] that our choices are fundamentally emotional. Our feelings are the underlying “context-setters” on which our rational brain acts. When we avoid certain emotional states, our solution set becomes constrained in ways we may not even be aware of.
I see this play out often, even at the highest levels of leadership. It’s why some of the most brilliant, sharp leaders still make terrible decisions: they’re unconsciously dodging or grasping at an emotion, and don’t have access to the full picture.
If you’re scared of upsetting your boss, you’re less likely to have the critical conversation that could revolutionize your business. If you’re scared of technology taking your job, you’re less likely to take a big swing in an unknown field. (And by the way, AI is an unknown field, and it’ll reward those willing to take lots of big swings.)
I saw this in action a few years ago, coaching the CEO of a fast-growing company. He was generous with his people and quick to please. But the company couldn’t kill anything—every initiative lived forever, their roadmap was clogged, and teams were stretched thin. He tried to fix it with reorgs and new prioritization frameworks. Nothing worked.
I asked him when he’d last said no to something in his personal life. He went quiet. His discomfort with disappointing people had become the company’s inability to prioritize.
The constraint was emotional, not strategic. Once we worked with this fear, he started sunsetting initiatives cleanly, and his team followed. Within six months they’d cut 40% of active projects, and revenue per employee had jumped.
Do this work, and your avoidance stops running the show from the backseat. That’s the real advantage in the age of AI.
How to check your readiness: Some of the most powerful work I do with CEOs is around uncovering the unconscious emotions that end up driving critical decisions. You can try it for yourself with a practice I call the Golden Algorithm:
Name a recurring frustration in your life.
Identify the emotion underneath it (rejection, helplessness, fear of abandonment, etc.).
List the ways you try to avoid that emotion. Be specific.
List the results. In almost every case, you’ll see that the strategy you’re using to avoid the emotion is creating the exact thing you’re afraid of.
For example:
Avoid failure → Play it safe/Never take big risks → Never win big → Feel like a failure.
Avoid conflict → People-please → Constant inner conflict → Resentment builds and leads to deeper conflict.
Avoid looking incompetent → Never ask questions → Stay confused → Underperform.
Avoid disappointing others → Say yes to everything → Be spread too thin → Disappoint everyone.
How to practice:
Change your relationship to your own emotional signal. Five minutes a day is enough to make a difference. Take the emotions you identified in the Golden Algorithm exercise and bring them to this practice: Emotional Inquiry [ https://substack.com/redirect/8aa5d6e0-0c1a-46b8-9414-e9949ae6aa38?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ].
Feel your feelings. Read and download this one-page guide [ https://substack.com/redirect/b56c008a-e7eb-4f97-abb4-a8f0a0f83c8a?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ].
How we do it at the Art of Accomplishment: Most people grade a decision by how it turned out—a good result means it was a good call; a bad result, a bad call. But that’s just holding yourself responsible for predicting the future, which even great investors can’t do. We treat our decisions like a portfolio, and focus instead on the process behind them.
Before a big decision, we ask ourselves: “Am I deciding to be myself and follow what I actually want, or am I trying to manage the future and avoid something I don’t want to feel?” If it’s the second one, we slow down and feel the thing first, then choose. Do that consistently and the portfolio wins, even when plenty of individual bets don’t. Every month, we also dogfood our own program, The Council [ https://substack.com/redirect/82a4e4db-9fd7-4435-84fa-9c23f320334f?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], a three-hour team check-in about our biggest fears. It surfaces and resolves the biggest conversations and decisions we have been avoiding.
2. “In conflict we trust”
AI makes it easier than ever to simulate the illusion of connection. A model can draft the tough message, rehearse the conversation 10 times, and give you a perfectly worded apology. But a model cannot open you up to saying the hard thing. It cannot make you put down the position you’ve been defending. AI can hand you every answer in the world, but it can’t make you use them.
You can buy more compute. It’s a lot harder to buy your way out of the conversations your team is avoiding. Like the CEO who’s too scared to tell his employees the truth, so the decision festers for months. It’s the two co-founders who stopped being honest with each other six months ago, and now route every hard conversation through a third person.
And with the NBA-ification of teams, one unresolved tension between two co-founders is no longer diluted across multiple layers in a big org. Now it’s a huge crack running through a tight roster. When each player’s leverage is critical and powerful, every broken relationship becomes that much more expensive.
As a result, being able to have productive conflict, surface difficult issues, and stay present during uncomfortable conversations is about to become staggeringly more valuable. Those who thrive in this new world move toward the difficulty instead of away, because every conflict looks like an inefficiency to be solved—and every new solution builds a stronger team bond.
I witnessed this firsthand with one of my clients, Johannes, who runs a developer-tools company (Ona [ https://substack.com/redirect/692e8e0a-363b-498f-9af7-fbfe96d86f40?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], formerly Gitpod) in one of the fastest-moving corners of the AI market. His leadership team had one of the usual buried tensions: sales versus engineering.
We brought their team through an intensive two-day summit [ https://substack.com/redirect/82a4e4db-9fd7-4435-84fa-9c23f320334f?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] built to surface the conversations they were avoiding. Afterward Johannes told me, “Our team did six months of work in two days. Every interpersonal conflict that was standing between us just went away. The clarity we walked away with, and the business decisions we’re now able to make, are extraordinary.”
6 Operating Principles That Make 80% of Decisions Automatic [ https://substack.com/redirect/318d06e8-f31e-4aba-8138-593812e5e46d?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
How to check your readiness: Pick your most important working relationship. Is there something true you haven’t said? How long has it gone unsaid? That number, in weeks or months, is your connection debt.
How to practice:
At the end of each week, write down two things nagging at you. Then actually call the people involved and talk about it. Hint: There’s an open, impartial approach we recommend for this called VIEW [ https://substack.com/redirect/b6946973-86ae-41c7-9b52-30438cb206b6?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] (Vulnerability, Impartiality, Empathy, Wonder). And remember, you don’t need to solve the problem before you raise it. If something isn’t working for you, just say, “Hey, something isn’t working for me,” and solve it together from there.
Twice a month, pick any important relationship (a co-founder, a partner, a manager, a friend you’ve drifted from) and ask yourself: “What’s the scary thing I’m not saying?”
How we do it at the Art of Accomplishment: We run on high transparency and no back channels. If you have a problem with someone, you bring it to them, not about them to everyone else. I also have a recurring block on my calendar dedicated to hard conversations, where I reflect on what has been nagging at me and then reach out to discuss it.
3. Willingness to fail
AI is extraordinary at what’s already known. Ask it for the best practice, the standard approach, or the analysis, and it’s faster than any of us could ever be. Now the bottleneck is how fast you can learn something new—and that requires a willingness to fail.
Almost no one thinks their way to a breakthrough in one sitting. They iterate their way there: build the thing, see what needs to improve, build the next version. The “creative genius” is just the one who took more shots faster, and learned more from each one. Think Steve Jobs, fired from the company he built and exiled for a decade. Or James Dyson, who built 5,126 vacuums that failed before one that worked. Or Michael Jordan, who missed over 9,000 shots, lost almost 300 games, and blew the game-winner 26 times.
Many of you are likely nodding along. This is the Silicon Valley bible; you’ve heard it a thousand times. But knowing this truism versus embodying it emotionally is completely different. There’s a structure in our brain called the habenula that cuts our motivation the moment it senses failure. It’s the same mechanism that stops a bear from fighting for dominance every day. Our brains beat us up before we ever try again.
That’s why true experimentation is actually quite rare. Most only iterate where it already feels safe—the A/B test, the side project, the experiment we’re fairly sure will work. Companies can build a culture of safety for bigger risks, and the best ones do. But if you’re anywhere near the bleeding edge, it won’t always feel safe to try something new. To succeed, you have to become comfortable with the feeling of failure and discover that you can move through the fear in seconds when you stop fighting it.
So the two halves work as one loop. The more reps you take, the more the threat response quiets down and failure feels like information, not threat. And the faster a team makes those reps feel normal, the more reps each person is willing to take. Team culture lowers the social cost of failing; individual practice lowers the felt cost. Each feeds the other. The fastest way to get someone comfortable with failure is to put them on a team where failed experiments are so ordinary—even celebrated—that you stop flinching.
A team that’s internalized this is Anthropic’s product team, which runs “side quests,” where anyone can spend an afternoon prototyping an idea outside the official roadmap. No approval, PRD, or alignment meeting is needed. They build the thing, ship it internally, and see what happens. If teammates keep using it the next day, and the day after that, it gets polished and released. If nobody touches it, it dies.
Rather than effort or coordination, they’ve optimized for the rate at which new ideas can hit reality and get tested.
How to check your readiness:
Look at your past month of work. How many big-swing experiments did you and your team run? We aim for about five per team member.
Each week, check in with your team and track “pace” and “spin.”
Pace is how fast you’re moving—the rate at which you’re iterating. How quickly can you build the thing, see what’s working, and start the next one? Rate it from 0% to 150%. You’re aiming for 100%. High pace is great, but a very high pace isn’t sustainable.
Spin is the hidden tax. It’s the feeling of your wheels spinning with brakes on: second-guessing, bracing before you take the shot, loops you get stuck in when failure feels like a threat rather than an opportunity for learning. Rate it from 0% to 100%. You want it under 30%.
How to practice:
Play with your job. Treat it as a series of experiments rather than mandates. Once a week, take the task you dread most and ask: “If I doubled how much I enjoyed this, what would I change?” Then ask: “What are the one or two things I could do this week that would make everything else on my list easier or irrelevant?”
Take a goal you’ve been circling. Instead of one big attempt you could “fail,” write down 20 small experiments you could run around it to learn something new. Then start running them. Each one you complete is a win, regardless of how it turns out. You’re training yourself to measure progress by iterations, not outcomes.
How we do it at the Art of Accomplishment: Everyone on our team is responsible for running five experiments every quarter to refine the way they work. These are fast and loose, and easy to measure. The important thing is the pace of trying new things and learning, not getting it right or taking weeks to design the perfect experiment. And this is true for everyone in our org, from an executive assistant to the president. We also have a “failure celebration” at our annual offsite where we present our biggest “failure.” It gets a standing ovation from the rest of the team.
4. Positive self-talk
This skill sits underneath and supports the other three, which is why it’s one of the biggest differentiators I see.
You can have all the talent in the world, but if you regularly talk to yourself in a hostile tone, that mentality makes you doubt every decision, kills your creativity, and puts you into chronic stress and overwhelm.
A study on perseverative cognition, or repetitive negative self-talk and worry, found that the body can’t tell the difference between an actual threat and a thought about a threat. When we criticize ourselves, our brain reacts as if we’re under attack. Cortisol and adrenaline spike, our heart rate climbs, and blood pressure rises. I’ve seen this affect the most creative and successful people I work with. Their biggest bottleneck is how they relate to themselves.
The internal voice of a lot of high performers is brutal: “You’re not doing enough. Why aren’t you further along? This isn’t good enough.”
In the pre-AI era, self-criticism could push you to outwork the person next to you. It hurt, but the negativity could lead to success (though eventually to burnout). That math has flipped. You can’t out-grind a server farm or outwork a model that doesn’t sleep. The voice that used to drive harder work is now just shutting down every single capability that’s a differentiator in the AI era.
The good news is that this skill is more trainable than knowledge or effort. You can’t add 50 IQ points or 20 years of experience to your resume. But your internal voice was learned, which means it can be changed. In fact, we know this because we’ve measured the impact of one of our programs for seven years: we improved negative self-talk by a full standard deviation across all participants.
How to check your readiness: For one day, treat your inner monologue as a transcript. Every time you notice yourself feeling tight, stuck, or low, stop and:
Set a 5-minute timer.
Write down exactly what’s going through your head.
Most people are stunned by what they find. The voice they’ve been listening to all day says things they would never say to a friend or their child: “That was stupid of you.” “Everyone can tell you’re faking it.” “You should have known better.” “You haven’t done enough today.” “You are an imposter.”
How to practice:...
Unsubscribe https://substack.com/redirect/2/eyJlIjoiaHR0cHM6Ly93d3cubGVubnlzbmV3c2xldHRlci5jb20vYWN0aW9uL2Rpc2FibGVfZW1haWw_dG9rZW49ZXlKMWMyVnlYMmxrSWpvME1qWTFNVFV3TkRBc0luQnZjM1JmYVdRaU9qSXdNamMyT0RrME1Td2lhV0YwSWpveE56Z3lNakU1TlRNMUxDSmxlSEFpT2pFNE1UTTNOVFUxTXpVc0ltbHpjeUk2SW5CMVlpMHhNRGcwTlNJc0luTjFZaUk2SW1ScGMyRmliR1ZmWlcxaGFXd2lmUS5IVWlDbGxtZUV4VHVtU0FZX3dQNTVRN01TQVJNRGJwMU9tZ01STlV2RDJZIiwicCI6MjAyNzY4OTQxLCJzIjoxMDg0NSwiZiI6dHJ1ZSwidSI6NDI2NTE1MDQwLCJpYXQiOjE3ODIyMTk1MzUsImV4cCI6MjA5Nzc5NTUzNSwiaXNzIjoicHViLTAiLCJzdWIiOiJsaW5rLXJlZGlyZWN0In0.CfifduPDTY-7lg8B6c9mqIJgJX5a7Y2bKfKs3hntjCw?
View Email
The new inner game: Your unfair advantage in the age of AI
lenny@substack.com6/23/2026
SubstackView this post on the web at https://www.lennysnewsletter.com/p/building-the-most-ai-pilled-engineering
Fiona Fung leads the teams behind Claude Code and Cowork at Anthropic (overseeing Boris Cherny and the entire engineering and PM team). Before Anthropic, she spent 11 years at Microsoft building Visual Studio and TypeScript and then moved to Meta, where she started Facebook Marketplace (now generating over $100 billion in GMV annually), worked on Meta’s first smart glasses and AR glasses, and led infrastructure, growth, integrity, and safety teams at Instagram. She’s been an engineer for over 25 years and has a unique perspective on how the role of building software is changing.
Listen on YouTube [ https://substack.com/redirect/f5192dfd-585b-4a38-ae92-d0ad6b8cc82b?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], Spotify [ https://substack.com/redirect/764992bd-deaa-44cb-8431-82bd5a2f2d04?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], and Apple Podcasts [ https://substack.com/redirect/5a4c42eb-6547-4aa5-a6a1-22e56b519ecc?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
In our in-depth conversation, we discuss:
What she’s learned about running a team that’s shipping 8x more code than before
Which roles AI will transform next
Specific ways her team uses AI
How Claude “routines” have changed how she operates as a manager
The context-switching problem no one has solved yet
The biggest unsolved problem in AI
What keeps her up at night
Brought to you by:
WorkOS [ https://substack.com/redirect/13ae8d70-3b0d-4abb-a282-dd6ecf0f963c?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]—Make your app enterprise-ready, with SSO, SCIM, RBAC, and more
Mercury [ https://substack.com/redirect/b0163412-5b89-4000-8b50-99cc5865056f?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]—Radically different banking, now with Command
Where to find Fiona Fung:
• LinkedIn: linkedin.com/in/fionafung [ https://substack.com/redirect/69794f7a-368b-4492-b193-d66756b6e30f?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Referenced:
• Running an AI-native engineering org: https://www.youtube.com/watch?v=igO8iyca2_g [ https://substack.com/redirect/6d2243d0-c6f9-421a-b116-421c0b988c1d?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Head of Claude Code: What happens after coding is solved | Boris Cherny: https://www.lennysnewsletter.com/p/head-of-claude-code-what-happens [ https://substack.com/redirect/07af34ba-da1a-44e9-b4df-8623fd9e52c2?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Today, Anthropic engineers on average ship 8x as much code per quarter as they did compared to 2021-2025: https://x.com/AnthropicAI/status/2062568864240836995 [ https://substack.com/redirect/9d29441b-8b73-48d3-a84f-92cfee258d00?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Visual Studio: https://visualstudio.microsoft.com [ https://substack.com/redirect/bde3afb9-a158-4773-b73f-39bdf8fe0c64?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Joseph Campbell’s quote: https://www.goodreads.com/quotes/192665-the-cave-you-fear-to-enter-holds-the-treasure-you [ https://substack.com/redirect/5c0a9ef0-79b4-419b-b5cb-a829151f56d3?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Life-changing Cowork use case: https://x.com/lennysan/status/2059664455001334124 [ https://substack.com/redirect/d4cf4e2d-89e4-4778-9aac-08833d42f9e3?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Introducing Claude for Small Business: https://www.anthropic.com/news/claude-for-small-business [ https://substack.com/redirect/bbd1155c-f6da-4b6f-8679-237c670ae491?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Conversations with Tyler podcast: https://conversationswithtyler.com [ https://substack.com/redirect/45d1675e-e823-4eb1-a24c-41f72db6b48b?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Sheryl Sandberg on Facebook: https://www.facebook.com/sheryl# [ https://substack.com/redirect/61fd3fc2-2255-4b90-9b3a-2dee1d5a37f2?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Amélie on Prime Video: https://www.amazon.com/Amelie-Jean-Pierre-Jeunet/dp/B0DQ4S3N45 [ https://substack.com/redirect/a440454c-bd51-4ba4-840a-68c07bbf254f?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Spirited Away on HBO Max: https://www.hbomax.com/movies/spirited-away/3deab668-d0a4-4a8d-9bc8-0952a0ad836e [ https://substack.com/redirect/b319436a-af0f-4748-ac7a-745f79fd8dc9?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Nausicaä of the Valley of the Wind on HBO Max: https://www.hbomax.com/movies/nausicaa-of-the-valley-of-the-wind/ed66031b-6353-4019-ba54-35488468a4db [ https://substack.com/redirect/717176bd-7c61-45fb-ab23-579013ef48ae?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Sweet Sisters Bodycare: https://sweetsistersbodycare.com [ https://substack.com/redirect/95843853-256b-434b-996e-d7ef781842e5?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Anthropic events: https://www.anthropic.com/events [ https://substack.com/redirect/2d5eb595-341c-4181-bbd6-ab27d01169a3?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Clare Pooley’s quote: https://www.goodreads.com/quotes/11305360-in-a-world-where-you-can-be-anything-be-kind [ https://substack.com/redirect/d752430f-3ff8-4314-96bb-ba797c796350?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Recommended books:
• Margaret Atwood’s books: https://www.amazon.com/stores/author/B000AQTHI0?ccs_id=0027a474-cd59-4a3a-bcd7-9b173c27d530 [ https://substack.com/redirect/5a61a8ba-e132-42c2-a882-7982bfad9933?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Haruki Murakami’s books: https://www.amazon.com/stores/Haruki-Murakami/author/B000AP7AFI [ https://substack.com/redirect/73d031ab-2636-4916-be38-4388ce21dbed?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• The Little Prince: https://www.amazon.com/Little-Prince-Antoine-Saint-Exup%C3%A9ry/dp/0156012197 [ https://substack.com/redirect/52af6d4d-9a97-4b40-8433-fb04701cc430?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Nausicaä of the Valley of the Wind: https://www.amazon.com/Nausica%C3%A4-Valley-Wind-Box-Set/dp/1421550644 [ https://substack.com/redirect/c41c9183-9197-4c6b-95df-1e0ffa7c4115?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• High Output Management: https://www.amazon.com/High-Output-Management-Andrew-Grove/dp/0679762884 [ https://substack.com/redirect/2c71240b-9027-4e82-8ea7-9a36c5c7a02e?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Production and marketing by https://penname.co/ [ https://substack.com/redirect/776a32aa-0e15-4108-8d20-3dd59951154d?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com [ mailto:podcast@lennyrachitsky.com ].
Lenny may be an investor in the companies discussed.
My biggest takeaways from this conversation:...
Unsubscribe https://substack.com/redirect/2/eyJlIjoiaHR0cHM6Ly93d3cubGVubnlzbmV3c2xldHRlci5jb20vYWN0aW9uL2Rpc2FibGVfZW1haWw_dG9rZW49ZXlKMWMyVnlYMmxrSWpvME1qWTFNVFV3TkRBc0luQnZjM1JmYVdRaU9qSXdNVEl5TmpjME55d2lhV0YwSWpveE56Z3lNRFExT1RFMExDSmxlSEFpT2pFNE1UTTFPREU1TVRRc0ltbHpjeUk2SW5CMVlpMHhNRGcwTlNJc0luTjFZaUk2SW1ScGMyRmliR1ZmWlcxaGFXd2lmUS5RX0hDa0VaV2RGaEhqUVVIQUlIVXBSSVRfa3RRcjRkWDRUQTBMT3JHNXRRIiwicCI6MjAxMjI2NzQ3LCJzIjoxMDg0NSwiZiI6dHJ1ZSwidSI6NDI2NTE1MDQwLCJpYXQiOjE3ODIwNDU5MTQsImV4cCI6MjA5NzYyMTkxNCwiaXNzIjoicHViLTAiLCJzdWIiOiJsaW5rLXJlZGlyZWN0In0.5_57-e2bEYSXhicXJU9-vsOEwMsWXjs6ZjzGnSspSpM?
View Email
Building the most AI-pilled engineering team in the world | Fiona Fung (Manager of the Claude Code and Cowork Team…
lenny@substack.com6/21/2026
SubstackView this post on the web at https://www.lennysnewsletter.com/cp/202598945
Unsubscribe https://substack.com/redirect/2/eyJlIjoiaHR0cHM6Ly93d3cubGVubnlzbmV3c2xldHRlci5jb20vYWN0aW9uL2Rpc2FibGVfZW1haWw_dG9rZW49ZXlKMWMyVnlYMmxrSWpvME1qWTFNVFV3TkRBc0luQnZjM1JmYVdRaU9qSXdNalU1T0RrME5Td2lhV0YwSWpveE56Z3hOemszT0RZekxDSmxlSEFpT2pFNE1UTXpNek00TmpNc0ltbHpjeUk2SW5CMVlpMHhNRGcwTlNJc0luTjFZaUk2SW1ScGMyRmliR1ZmWlcxaGFXd2lmUS5yUU1pWGtqVDdhVEpsMU1URjlyTmF0UmdGb25ZS3VRQ2JnOVg1NXcxT2o4IiwicCI6MjAyNTk4OTQ1LCJzIjoxMDg0NSwiZiI6dHJ1ZSwidSI6NDI2NTE1MDQwLCJpYXQiOjE3ODE3OTc4NjMsImV4cCI6MjA5NzM3Mzg2MywiaXNzIjoicHViLTAiLCJzdWIiOiJsaW5rLXJlZGlyZWN0In0.e1E2-AmeNY-GFT7ww0LEwdtPJY1Fl7A6wlGXWHhUVUY?
View Email
The Mom-and-Pop SaaS era has arrived
lenny@substack.com6/18/2026
SubstackView this post on the web at https://www.lennysnewsletter.com/p/the-common-pattern-behind-successful
Mark Pincus founded Zynga—the company behind Words With Friends, FarmVille, and Zynga Poker—and has arguably created more hit consumer products than anyone in history. At Zynga, eight of 10 major game launches became massive hits, reaching over a billion players. Over the past five years, Mark has been synthesizing everything he’s learned about building successful consumer products and turning it into a book, Life at the Speed of Play, which comes out on June 23. This is the first interview he’s done about the book.
Listen on YouTube [ https://substack.com/redirect/32809a1a-da34-4702-801f-94d3d521bd72?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], Spotify [ https://substack.com/redirect/2ba8492e-83be-4ab8-9d7d-1b9f44e2da19?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], and Apple Podcasts [ https://substack.com/redirect/5867ced9-8a9e-44c6-9b81-c2c4def2351b?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
In our in-depth conversation, we discuss:
His “Proven, Better, New” framework: copy what’s proven, make it better so that 10 out of 10 people say “f*ck yes, I’ll use this”—then add something new
Why being less ambitious is the path to the most ambitious ideas
His rule of thumb that your instincts are right 95% of the time, but your ideas are wrong 75% of the time
“Kill hope before hope kills you”
How to raise kids in the age of AI
Brought to you by:
WorkOS [ https://substack.com/redirect/27046de7-65f5-4d5f-ba6d-0093c2cb24ea?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]—Make your app enterprise-ready, with SSO, SCIM, RBAC, and more
Vanta [ https://substack.com/redirect/b89f0bbe-9e50-4cde-bf40-b4c0ef438f53?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]—Automate compliance, manage risk, and accelerate trust with AI
Where to find Mark Pincus:
• X: https://x.com/markpinc [ https://substack.com/redirect/cc84f50c-0c63-43da-898c-76c371a3cd27?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• LinkedIn: https://www.linkedin.com/in/markpincus [ https://substack.com/redirect/6dff5a2a-1739-46a8-a35f-97e438472bdd?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Website: https://www.lifeatthespeedofplay.com [ https://substack.com/redirect/10aea3bf-3156-4835-813f-10e2087d56d9?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Referenced:
• Tribe.net: https://en.wikipedia.org/wiki/Tribe.net [ https://substack.com/redirect/d031abc6-f83e-4ecd-93ae-2562be1a0ad4?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Zynga: https://www.zynga.com [ https://substack.com/redirect/3462be38-e914-48fe-b9e2-ad82300ec946?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Sid Meier: https://en.wikipedia.org/wiki/Sid_Meier [ https://substack.com/redirect/f1951cb3-8ec1-4fca-ad7b-78adc35aa5e5?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Electronic Arts: https://www.ea.com [ https://substack.com/redirect/50be43c0-8889-4fb8-9d2a-923db3219e96?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• CityVille: https://en.wikipedia.org/wiki/CityVille [ https://substack.com/redirect/dd88ed8f-a8d4-4c9b-a312-e01762ff35f7?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Words With Friends: https://wordswithfriends.com/ [ https://substack.com/redirect/49536b3c-95de-4bda-b62f-316b8fabdaa6?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Scrabble: https://playscrabble.com [ https://substack.com/redirect/11902ae7-71ac-4b12-a6e5-c8b29788d226?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Reddit: https://www.reddit.com [ https://substack.com/redirect/4a8b49fc-99b5-4217-b6aa-122b730e031b?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• TED Radio Hour, MIT Media Lab founder, 1984 TED talk.: https://www.ted.com/talks/nicholas_negroponte_5_predictions_from_1984 [ https://substack.com/redirect/bbb9c75c-4142-425e-83b4-d008ef9fe6dc?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Peter Thiel on LinkedIn: https://www.linkedin.com/in/peterthiel [ https://substack.com/redirect/92a96901-46b7-498c-b9d4-e80bb6a5e201?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• FarmVille: https://en.wikipedia.org/wiki/FarmVille [ https://substack.com/redirect/52ab10d7-fcd4-4a98-bc05-54549eeae0e8?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Craig Newmark: https://en.wikipedia.org/wiki/Craig_Newmark [ https://substack.com/redirect/9e05ba21-9c2f-4299-8e1a-9c65b0ee3d3b?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• How to consistently go viral: Nikita Bier’s playbook for winning at consumer apps (co-founder of TBH, Gas, advisor, investor): https://www.lennysnewsletter.com/p/how-to-consistently-go-viral-nikita-bier [ https://substack.com/redirect/9d2e690a-a1ab-4ff2-bb20-48c58a0f2fae?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Angry Birds: https://www.angrybirds.com/ [ https://substack.com/redirect/1e2a07ff-d1c7-44e7-8b73-04b4dcf97734?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• OMGPop: https://en.wikipedia.org/wiki/OMGPop [ https://substack.com/redirect/a819a9e7-0731-4ef2-9248-6451bf21968d?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Draw Something: https://en.wikipedia.org/wiki/Draw_Something [ https://substack.com/redirect/902b3565-2cf6-4413-9e21-c2bc273fb11a?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Slack founder: Mental models for building products people love ft. Stewart Butterfield: https://www.lennysnewsletter.com/p/slack-founder-stewart-butterfield [ https://substack.com/redirect/83931081-43c9-4760-877c-a9c634b557f5?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Brian Chesky’s new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach [ https://substack.com/redirect/91bf437b-15c8-4556-9c0b-c25db8d1bfbd?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Garry Tan on LinkedIn: https://www.linkedin.com/in/garrytan [ https://substack.com/redirect/92045de3-8700-4b0d-9a5e-e8803bd9c187?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Brian Armstrong on LinkedIn: https://www.linkedin.com/in/barmstrong [ https://substack.com/redirect/1c42b507-eeed-4a48-be65-a943cc09587e?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Jason Citron on X: https://x.com/jasoncitron [ https://substack.com/redirect/b4e876bd-297a-4687-9875-6947fa0738f0?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Stanislav Vishnevskiy on LinkedIn: https://www.linkedin.com/in/svishnevskiy [ https://substack.com/redirect/830503bf-71c5-49f8-97db-ec886ce8b53b?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Jeff Bezos on X: https://x.com/JeffBezos [ https://substack.com/redirect/4da0ecfe-d91f-46f0-8d6c-0d9d29623388?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Andy Jassy on X: https://x.com/ajassy [ https://substack.com/redirect/bee392c5-18be-49c8-898e-80d1ad73da25?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Niantic: https://nianticlabs.com [ https://substack.com/redirect/00f0a1ac-4b02-4930-8174-763ea3ee8d9d?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Pokémon Go: https://pokemongo.com [ https://substack.com/redirect/e2ed6801-fab6-432c-a4da-69137df7af71?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Bing Gordon on LinkedIn: https://www.linkedin.com/in/binggordon [ https://substack.com/redirect/6cee70a6-2b1e-4131-8e76-b76644846f22?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Recommended book:
• Life at the Speed of Play: Launch Products People Love!: https://www.amazon.com/Life-Speed-Play-Launch-Products/dp/0063352575/ [ https://substack.com/redirect/77a5438c-8652-4dce-9b3d-e3511fd35db3?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Production and marketing by https://penname.co/ [ https://substack.com/redirect/b8ea3d10-6d14-4152-9ff5-319d27afadbe?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com [ mailto:podcast@lennyrachitsky.com ].
Lenny may be an investor in the companies discussed.
My biggest takeaways from this conversation:...
Unsubscribe https://substack.com/redirect/2/eyJlIjoiaHR0cHM6Ly93d3cubGVubnlzbmV3c2xldHRlci5jb20vYWN0aW9uL2Rpc2FibGVfZW1haWw_dG9rZW49ZXlKMWMyVnlYMmxrSWpvME1qWTFNVFV3TkRBc0luQnZjM1JmYVdRaU9qRTVPRFU1TVRrNE5Dd2lhV0YwSWpveE56Z3hORFF4TURjNExDSmxlSEFpT2pFNE1USTVOemN3Tnpnc0ltbHpjeUk2SW5CMVlpMHhNRGcwTlNJc0luTjFZaUk2SW1ScGMyRmliR1ZmWlcxaGFXd2lmUS5rdzRNNlRwQzR6ZngyTGFjT0FGam5vZVpRemlfczFiMktDV2xnZThDWHlrIiwicCI6MTk4NTkxOTg0LCJzIjoxMDg0NSwiZiI6dHJ1ZSwidSI6NDI2NTE1MDQwLCJpYXQiOjE3ODE0NDEwNzgsImV4cCI6MjA5NzAxNzA3OCwiaXNzIjoicHViLTAiLCJzdWIiOiJsaW5rLXJlZGlyZWN0In0.OjVlpKIZ2kZqwUmy7moSm-kJEyk6RRVjVx5kuIPtoiE?
View Email
The hidden pattern behind successful products | Mark Pincus (Founder of Zynga)
lenny@substack.com6/14/2026
SubstackView this post on the web at https://www.lennysnewsletter.com/cp/201477355
Unsubscribe https://substack.com/redirect/2/eyJlIjoiaHR0cHM6Ly93d3cubGVubnlzbmV3c2xldHRlci5jb20vYWN0aW9uL2Rpc2FibGVfZW1haWw_dG9rZW49ZXlKMWMyVnlYMmxrSWpvME1qWTFNVFV3TkRBc0luQnZjM1JmYVdRaU9qSXdNVFEzTnpNMU5Td2lhV0YwSWpveE56Z3hNVEE1TkRjMkxDSmxlSEFpT2pFNE1USTJORFUwTnpZc0ltbHpjeUk2SW5CMVlpMHhNRGcwTlNJc0luTjFZaUk2SW1ScGMyRmliR1ZmWlcxaGFXd2lmUS55SHJDWHU5bm1DUGhpQ3hhVE5OX2Z1d3ZaNlFjMGtfNkVucHJUcWlCZGp3IiwicCI6MjAxNDc3MzU1LCJzIjoxMDg0NSwiZiI6dHJ1ZSwidSI6NDI2NTE1MDQwLCJpYXQiOjE3ODExMDk0NzYsImV4cCI6MjA5NjY4NTQ3NiwiaXNzIjoicHViLTAiLCJzdWIiOiJsaW5rLXJlZGlyZWN0In0.Gdx5dfH0H0Q_qfKyDYLmYRaNCqk4K04F9W8UFp98PEE?
View Email
5 Career Questions Your Old Playbook Can’t Answer
lenny@substack.com6/10/2026
SubstackView this post on the web at https://www.lennysnewsletter.com/p/essential-books-for-product-builderspart-611
👋 Hey there, I’m Lenny. Each week, I answer reader questions about building product, driving growth, and accelerating your career. For more: Lenny’s Podcast [ https://substack.com/redirect/b3264ab1-22e6-4cd7-af32-2dad32a94eeb?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] | Lennybot [ https://substack.com/redirect/17e4dc27-77c3-4f77-aab9-d033a0e6c211?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] | How I AI [ https://substack.com/redirect/379acf32-d00a-4723-969a-5894ce7a31f4?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] | My favorite AI/PM courses [ https://substack.com/redirect/60a3944f-7785-4374-9d6d-c79dd732f059?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], public speaking course [ https://substack.com/redirect/5e946521-6aa8-4502-97d8-e6c6497917b1?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], and interview prep copilot [ https://substack.com/redirect/fd6c0c44-f0c5-4dd4-b8f1-4dea38c0dff9?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
P.S. Get a full free year of Google AI, Cursor, Lovable, Notion, Manus, Replit, Gamma, n8n, Canva, ElevenLabs, Factory, Wispr Flow, Fin, Supabase, Bolt, Linear, PostHog, Framer, Railway, Granola, Warp, Gumloop, Magic Patterns, Mobbin, Stripe Atlas, and ChatPRD, by becoming an Insider subscriber [ https://substack.com/redirect/e9b793a1-efe2-44c3-ac8e-e0c5f5bc5f8a?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]. Yes, this is for real [ https://substack.com/redirect/66483ee9-9a9b-4364-bdd3-26dbfab13975?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ].
On the heels of part 1 [ https://substack.com/redirect/4185aa8e-c7a1-4204-97ac-a178fb512f5e?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] of my essential books for product builders series, I’m excited to share part 2.
As with last time, the books are organized by their jobs-to-be-done in your work and life. I’m again limiting myself to only three per category that I’ve personally read (and completed), and only books that have stood the test of time (i.e., no new books). As a bonus, at the end of the post I’ve also included a dozen fan favorites that either fell just below the ones I picked or I haven’t had a chance to read yet.
I know it’s hard to find time to read a whole book, and when you do, it’s hard to retain anything. As I mentioned in part 1, what’s worked for me is to read 10 minutes before bed as part of my wind-down routine. This has the added benefit of helping me sleep better! And as I read, I try to find one nugget or tactic that I can bring into my work that week. I take a photo of it and email it to myself (using this sweet app [ https://substack.com/redirect/10c869be-b4ff-4d7f-bd41-3cf3676cc839?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]) for the next morning. My philosophy is that if I retain just one golden nugget per book over the years, I’m happy. That’s how it usually ends up working out anyway.
So, as I share the book recommendations, I’ll also highlight a nugget of wisdom that’s still with me over the many years since I first read these books.
Let’s get into it.
“Books are the closest thing you’ll ever come to finding cheat codes for real life. You can access the entire learnings of someone else’s career in a few hours.” —Tobi Lütke [ https://substack.com/redirect/ea7a02f2-f522-47bb-8389-2aefe53a5f34?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
I want to get better at design
Before reading these books, I thought design was a squishy, subjective thing. It’s not. Don’t Make Me Think taught me how to objectively make a product UI work (and feel) better. The Design of Everyday Things showed me that when I struggle with a product, it’s not my fault—it’s the design’s. Refactoring UI gave me a ton of specific design tactics.
Don’t Make Me Think [ https://substack.com/redirect/a9703121-0de0-4764-a0f8-58311f4a8f22?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] by Steve Krug
The Design of Everyday Things [ https://substack.com/redirect/fc8fcc9f-24b4-44c9-92e9-41012841a1f2?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] by Don Norman
Refactoring UI [ https://substack.com/redirect/e9419cee-b825-49f0-ba12-df6fafa4f975?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] by Adam Wathan and Steve Schoger
I want to improve my taste/craft
I’ve always looked up to people who have great taste, and lucky for me, guests on my podcast consistently remind me that it isn’t something you’re born with—taste is something you can learn. The War of Art helped me learn how to recognize and overcome the internal “resistance” that comes with creating something new and different. The Work of Art showed me the creative process of dozens of high-taste creators. Creativity, Inc. taught me to protect my (and my team’s) “ugly babies”—early half-baked ideas that otherwise get squashed.
The War of Art [ https://substack.com/redirect/b3dbde70-425b-4cb8-b184-653d35cd3e05?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] by Steven Pressfield
The Work of Art [ https://substack.com/redirect/5df1f1cf-6162-48fa-9175-8e02845f9a63?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] by Adam Moss
Creativity, Inc. [ https://substack.com/redirect/26f8d8ed-c0b6-4a7a-8118-ce7a1ca79484?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] by Ed Catmull
I want to get better at influence
Influence—maybe you’ve heard it’s important? It’s something I was very bad at early in my career, and I’ve had to learn how to do it well. How to Win Friends and Influence People showed me the power in being interested vs. interesting. Influence taught me the fundamentals of how people change their mind: social proof, authority, scarcity, and simply being liked. Never Split the Difference taught me how to shift a negotiation from “you vs. me” to “us” working together to solve the problem.
How to Win Friends and Influence People [ https://substack.com/redirect/8dfb5bbf-8607-4ab3-ae17-1ea89691bd4d?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] by Dale Carnegie
Influence [ https://substack.com/redirect/f3f0ba94-3c80-4811-aa3d-89d0c3618ea9?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] by Robert Cialdini
Never Split the Difference [ https://substack.com/redirect/d38e19e8-74ca-47d2-851b-2be321099ee8?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] by Chris Voss
I want to start a company
I’ll be honest, I didn’t read a lot of books when I was starting my company. But I should have. When I finally read The Lean Startup, it showed me how to be smart about where to start, and how to iterate efficiently. Crossing the Chasm taught me what a good early user looks like. Fall in Love with the Problem, Not the Solution finally gave me a very practical guide for every step of the founder journey.
The Lean Startup [ https://substack.com/redirect/837f9a73-f6af-4d81-a202-0349ce821dc3?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] by Eric Ries
Crossing the Chasm [ https://substack.com/redirect/977feebd-7539-40c3-993f-0f8b3fe56379?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] by Geoffrey Moore
Fall in Love with the Problem, Not the Solution [ https://substack.com/redirect/43ad7620-d6f1-49a2-ad0f-e6a230841175?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] by Uri Levine
I want to advance my career
There are certain books you read and you’re just like, “Wow, this really explains what’s going on around here.” These three did that for me. Great at Work showed me that people who rise fastest focus on fewer things but do them extremely well. 7 Rules of Power taught me that, often, it isn’t the most talented or nice people who end up winning. The Effective Executive helped me understand that efficiency is doing things well, while effectiveness is doing the right (highest-leverage) things.
Great at Work [ https://substack.com/redirect/43f6bbb7-1b83-4417-a84d-64da21409fec?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] by Morten T. Hansen
7 Rules of Power [ https://substack.com/redirect/63961f25-dc7c-4be0-9f1f-b3c2012c2524?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] by Jeffrey Pfeffer
The Effective Executive [ https://substack.com/redirect/23b73a87-9f6a-4415-9c51-b634c4655bcb?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] by Peter Drucker
I want to be happier (continued)
A few readers suggested that this category should have come first last time—what else matters if you can’t be happy? So I’m including another three books that made me a happier person. The Subtle Art of Not Giving a F*ck taught me that freedom from work isn’t the real goal. Instead, it’s your opportunity to figure out what problems you want to spend time solving, because the most lasting fulfillment comes from solving problems we care about. A Guide to the Good Life gave me the skill of “negative visualization,” which I use to this day. Stumbling on Happiness showed me that we’re often (very) wrong about what will make us happy.
The Subtle Art of Not Giving a F*ck [ https://substack.com/redirect/6fabc502-0c42-4981-bbcf-cf4cdaf5a9fc?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] by Mark Manson
A Guide to the Good Life [ https://substack.com/redirect/c7a83ab6-5707-4a06-918a-f7eb176487e6?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] by William B. Irvine
Stumbling on Happiness [ https://substack.com/redirect/cd7804df-32cb-41cf-90c3-a2922c1b8e06?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] by Daniel Gilbert
I want some great children’s books...
Unsubscribe https://substack.com/redirect/2/eyJlIjoiaHR0cHM6Ly93d3cubGVubnlzbmV3c2xldHRlci5jb20vYWN0aW9uL2Rpc2FibGVfZW1haWw_dG9rZW49ZXlKMWMyVnlYMmxrSWpvME1qWTFNVFV3TkRBc0luQnZjM1JmYVdRaU9qSXdNRGd6TURFMk9Td2lhV0YwSWpveE56Z3hNREV4TXpjeUxDSmxlSEFpT2pFNE1USTFORGN6TnpJc0ltbHpjeUk2SW5CMVlpMHhNRGcwTlNJc0luTjFZaUk2SW1ScGMyRmliR1ZmWlcxaGFXd2lmUS5CYkZkRzB3VnIyR1BWRnRTeDlfaXExZkhTV3VfMThXR08wOUJvYWdwNjRvIiwicCI6MjAwODMwMTY5LCJzIjoxMDg0NSwiZiI6dHJ1ZSwidSI6NDI2NTE1MDQwLCJpYXQiOjE3ODEwMTEzNzIsImV4cCI6MjA5NjU4NzM3MiwiaXNzIjoicHViLTAiLCJzdWIiOiJsaW5rLXJlZGlyZWN0In0.lUVTAi9fM0yBqnRjT5EGs3XxVULJ9wtjJN-215RYKko?
View Email
Essential books for product builders—part 2
lenny@substack.com6/9/2026
SubstackView this post on the web at https://www.lennysnewsletter.com/p/father-of-the-ipod-and-iphone-on
Tony Fadell created the iPod, co-created the iPhone, and founded Nest (which he sold to Google for $3.2 billion). He’s co-authored over 300 patents, was part of the legendary team at General Magic, and wrote one of the most important and inspiring books for builders, called Build.
Listen on YouTube [ https://substack.com/redirect/11a36f0a-e484-46a9-a14a-40ed20e7d4a1?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], Spotify [ https://substack.com/redirect/edaea144-06e7-4126-bc9c-d3c3ae4616a5?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], and Apple Podcasts [ https://substack.com/redirect/0c04b0b2-b614-49ef-9688-ea75d1721d24?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
In our in-depth conversation, we discuss:
The heated internal debates about whether the iPhone should have a physical keyboard
Why opinion-based decisions are essential for v1 products
Why marketing matters as much as the product itself, and how the iPod almost failed
Why voice will eventually become the primary interface with AI
Why cognitive surrender to AI is the biggest risk facing product builders today
Brought to you by:
WorkOS [ https://substack.com/redirect/bea6da9b-6fc1-407f-9812-13be309556e6?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]—Make your app enterprise-ready, with SSO, SCIM, RBAC, and more
Vanta [ https://substack.com/redirect/0f32139f-8d3b-4f5d-86eb-67feb6017286?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]—Automate compliance, manage risk, and accelerate trust with AI
Where to find Tony Fadell:
• X: https://x.com/tfadell [ https://substack.com/redirect/56bca1aa-690e-4cc2-a84f-b19d0262a03b?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• LinkedIn: https://www.linkedin.com/in/tonyfadell [ https://substack.com/redirect/8eea1788-27ec-4108-baca-f5abf163d49d?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Website: https://www.buildc.com [ https://substack.com/redirect/00a0d19b-b93d-44d8-a0c2-b64b44ab66f8?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Referenced:
• BlackBerry: https://www.netflix.com/title/81725542 [ https://substack.com/redirect/80ba9616-336e-43d8-9a6f-643468fa4bac?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Functional systems: https://x.com/bhalligan/status/2051873396896518558/photo/1 [ https://substack.com/redirect/76e073d5-9825-4071-a774-522fce7757bb?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Nest: https://en.wikipedia.org/wiki/Google_Nest [ https://substack.com/redirect/57df1c8f-4fc2-4e82-86f9-8c1778f4ffd4?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Everyone’s an engineer now: Inside v0’s mission to create a hundred million builders | Guillermo Rauch (founder and CEO of Vercel, creators of v0 and Next.js): https://www.lennysnewsletter.com/p/everyones-an-engineer-now-guillermo-rauch [ https://substack.com/redirect/d2146ed8-4965-4db6-b44a-aad6ea63260e?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Hermann Hauser on LinkedIn: https://www.linkedin.com/in/hermannhauser [ https://substack.com/redirect/e73ed869-47ad-42e3-be62-d22c123c5721?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Acorn Computers: https://en.wikipedia.org/wiki/Acorn_Computers [ https://substack.com/redirect/e4a01225-ff56-4c59-9eba-1a24f2b457e5?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Skunkworks project: https://en.wikipedia.org/wiki/Skunkworks_project [ https://substack.com/redirect/51f80e84-6def-471a-b7e7-9eb1b87d66ac?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Netscape Navigator: https://en.wikipedia.org/wiki/Netscape_Navigator [ https://substack.com/redirect/a135222d-44f7-44b9-85e8-a3a9db184875?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Unpacking Amazon’s unique ways of working | Bill Carr (author of Working Backwards): https://www.lennysnewsletter.com/p/unpacking-amazons-unique-ways-of [ https://substack.com/redirect/01965745-2da5-4240-b5e9-6dc51d0e8255?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• General Magic: https://www.imdb.com/title/tt6849786 [ https://substack.com/redirect/619e60ef-c87b-4b98-b34a-69903762db84?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Dario Amodei’s website: https://www.darioamodei.com [ https://substack.com/redirect/7c990433-7f7b-487c-8fc0-b547fa8bde19?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Flighty: https://flighty.com [ https://substack.com/redirect/20faecce-7fa1-4a3b-9980-e6764317762b?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Dave Chappelle: https://en.wikipedia.org/wiki/Dave_Chappelle [ https://substack.com/redirect/38890339-8efc-4fdf-b20f-db799935384d?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Humane Inc.: https://en.wikipedia.org/wiki/Humane_Inc [ https://substack.com/redirect/d807ce7d-ad20-44f3-8025-20e174fa8a43?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Her: https://www.imdb.com/title/tt1798709 [ https://substack.com/redirect/748481b1-e2fd-4729-bda2-7097df0941e1?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Spike Jonze: https://en.wikipedia.org/wiki/Spike_Jonze [ https://substack.com/redirect/e1a4189d-8c74-4bdb-9284-b9a5ec8dc1d2?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Waymo: https://waymo.com [ https://substack.com/redirect/bd93d22c-dde6-41ab-a3ea-976178fe8483?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Snapchat CEO: Why distribution has become the most important moat | Evan Spiegel: https://www.lennysnewsletter.com/p/snapchat-ceo-why-distribution-is [ https://substack.com/redirect/66bca6ab-8c8d-4d6d-a8ff-09134df27f6c?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Simbe Robotics: https://www.simberobotics.com [ https://substack.com/redirect/7cb269fd-9fb0-4bcc-ba9e-a305e0869ae6?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Greyparrot: https://www.greyparrot.ai [ https://substack.com/redirect/7262e345-6234-42fb-83e4-d0d9dcc8299d?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Grok: https://grok.com [ https://substack.com/redirect/bc382484-2979-404e-ac01-590fed8ff7a6?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Cerebras: https://www.cerebras.ai [ https://substack.com/redirect/bb67145d-29a4-47f8-b561-bb385aeda1c5?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Esther 4:14: https://www.biblegateway.com/verse/en/Esther%204%3A14 [ https://substack.com/redirect/d9ee18b5-76c3-444e-a2ec-5ce3fd52a73f?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• iPod Inventor and Nest Founder Tony Fadell Named MAD’s Inaugural Designer in Residence: https://mad.mit.edu/news/ipod-inventor-and-nest-founder-tony-fadell-named-mit-morningside-academy-for-design-s-inaugural-designer-in-residence [ https://substack.com/redirect/667d18e7-2a4b-410b-bd93-4ca706c788e0?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Recommended books:
• Build: An Unorthodox Guide to Making Things Worth Making: https://www.amazon.com/dp/0063046067 [ https://substack.com/redirect/d312b7a0-7208-4669-8e56-ab017fd36665?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Working Backwards: Insights, Stories, and Secrets from Inside Amazon: https://www.amazon.com/Working-Backwards-Insights-Stories-Secrets/dp/1250275717 [ https://substack.com/redirect/fcc3f320-9b44-45c9-8350-edb2a40dbb0b?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Production and marketing by https://penname.co/ [ https://substack.com/redirect/1e94de41-fc01-4282-b9bf-08d06b2e7f7b?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com [ mailto:podcast@lennyrachitsky.com ].
Lenny may be an investor in the companies discussed.
My biggest takeaways from this conversation:...
Unsubscribe https://substack.com/redirect/2/eyJlIjoiaHR0cHM6Ly93d3cubGVubnlzbmV3c2xldHRlci5jb20vYWN0aW9uL2Rpc2FibGVfZW1haWw_dG9rZW49ZXlKMWMyVnlYMmxrSWpvME1qWTFNVFV3TkRBc0luQnZjM1JmYVdRaU9qRTVPRFU1TVRrMU5pd2lhV0YwSWpveE56Z3dPRE0yTWpVeUxDSmxlSEFpT2pFNE1USXpOekl5TlRJc0ltbHpjeUk2SW5CMVlpMHhNRGcwTlNJc0luTjFZaUk2SW1ScGMyRmliR1ZmWlcxaGFXd2lmUS45eVFzZGtlS0dDVmNnS0xuWlhocWI0Y3JQckJOZ3hnZWdkUDgzX2VjcXVrIiwicCI6MTk4NTkxOTU2LCJzIjoxMDg0NSwiZiI6dHJ1ZSwidSI6NDI2NTE1MDQwLCJpYXQiOjE3ODA4MzYyNTIsImV4cCI6MjA5NjQxMjI1MiwiaXNzIjoicHViLTAiLCJzdWIiOiJsaW5rLXJlZGlyZWN0In0.NyKAbVE9JWb1YUjPWO4lJn4tsg94CobQ1ZmJ27Alrks?
View Email
Father of the iPod and iPhone on building taste, judgment, and creativity in the AI era | Tony Fadell
lenny@substack.com6/7/2026
SubstackView this post on the web at https://www.lennysnewsletter.com/cp/200821257
Unsubscribe https://substack.com/redirect/2/eyJlIjoiaHR0cHM6Ly93d3cubGVubnlzbmV3c2xldHRlci5jb20vYWN0aW9uL2Rpc2FibGVfZW1haWw_dG9rZW49ZXlKMWMyVnlYMmxrSWpvME1qWTFNVFV3TkRBc0luQnZjM1JmYVdRaU9qSXdNRGd5TVRJMU55d2lhV0YwSWpveE56Z3dOamswTnpVeUxDSmxlSEFpT2pFNE1USXlNekEzTlRJc0ltbHpjeUk2SW5CMVlpMHhNRGcwTlNJc0luTjFZaUk2SW1ScGMyRmliR1ZmWlcxaGFXd2lmUS5XNlVOWk43UWl5bEhDQVd2N0FkdjFLaDg4Q09IX2ZRTVAxcXQ2eTNZSDBnIiwicCI6MjAwODIxMjU3LCJzIjoxMDg0NSwiZiI6dHJ1ZSwidSI6NDI2NTE1MDQwLCJpYXQiOjE3ODA2OTQ3NTIsImV4cCI6MjA5NjI3MDc1MiwiaXNzIjoicHViLTAiLCJzdWIiOiJsaW5rLXJlZGlyZWN0In0.pwe-kaiHXH0b9lSNW5w_o-TXJSfYSyxHQFd2aeJFxCY?
View Email
Your AI strategy has a trust problem, not a tooling problem
lenny@substack.com6/5/2026
SubstackWith an audience of over 1 million subscribers globally, we have a unique opportunity to tap into how the tech world is thinking and feeling right now—happiness and burnout levels, optimism and pessimism about the job landscape with the rise of AI, and more.
Our inaugural tech workers’ sentiment survey [ https://substack.com/redirect/6b91e81a-af87-4841-a33e-9303441e6d5a?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] in 2025 collected over 8,000 responses (the largest survey of its kind) and uncovered that mid-career workers were struggling the most, small-company employees were the happiest, and while almost half of you were experiencing significant burnout, the majority were still generally optimistic about your careers.
Today, we’re kicking off round two, and we’d love to hear from you!
The survey will take less than 5 minutes to complete. We’ll ask about your feelings toward work in tech, in addition to a few demographic questions.
If you complete the survey in full, we’ll share the anonymized raw data with you so you can perform your own analysis—plus an early look at the results before we share them publicly.
When filling out the survey, please be as honest as possible—your answers will stay completely anonymous, and your candid answers will help others. This is an important moment for the industry, and we’d love to get your perspective.
P.S. Please take the survey [ https://substack.com/redirect/b5fbab42-25d8-4072-a067-39ae46cafdff?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] (it’ll take you less than 5 minutes!).
With appreciation,
Lenny and Noam
View Email
Announcing: The second annual tech worker sentiment survey
lenny@substack.com6/2/2026
SubstackView this post on the web at https://www.lennysnewsletter.com/p/a-rational-conversation-on-where
Benedict Evans is an independent analyst and former partner at Andreessen Horowitz, where he spent years as their in-house “thinker” tracking the most important technology trends. For the past six years, he’s been publishing deeply researched presentations on where tech is heading, most recently focused on AI’s transformation of the economy. His work is read by founders, investors, and operators trying to make sense of a noisy field. His most controversial opinion: AI is as big a deal as the internet or mobile—and only as big.
Listen on YouTube [ https://substack.com/redirect/4270d589-466e-4f91-b00a-1d9cbff53eac?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], Spotify [ https://substack.com/redirect/8ffb736b-90d8-44e8-89dc-debcdff4efb1?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], and Apple Podcasts [ https://substack.com/redirect/e4fcb45f-6bfc-42d7-abfd-62ffe9ee911f?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
In our in-depth conversation, we discuss:
Why we’re in “1997” for AI—early, exciting, and deeply uncertain about what comes next
Where value will actually accrue in the AI stack
The anti-AI backlash, and where it may lead
The surprising boom in consulting and professional services at AI companies
Why distribution is becoming the ultimate moat as software gets easier to build
Why the right question about your job isn’t “What percent can AI do?” but “Is this a task or a job?”
Why things will probably be okay—and what you need to do to prepare
Brought to you by:
WorkOS [ https://substack.com/redirect/f1ce8615-d216-4937-be59-6525541e927d?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]—Make your app enterprise-ready, with SSO, SCIM, RBAC, and more
Vanta [ https://substack.com/redirect/1c808bc8-0e28-4bee-a3a7-ee9189b147d8?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]—Automate compliance, manage risk, and accelerate trust with AI
Where to find Benedict Evans:
• LinkedIn: https://www.linkedin.com/in/benedictevans [ https://substack.com/redirect/74ac1209-77f8-4ce1-9385-75e892c0995f?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Newsletter: https://www.ben-evans.com/newsletter [ https://substack.com/redirect/8d9cb079-f8b9-43b0-a5f4-81c1af0c8581?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Website: https://www.ben-evans.com [ https://substack.com/redirect/5ee72c8c-26a9-451c-a060-517fdf53c8cb?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Referenced:
• Andreessen Horowitz: https://a16z.com [ https://substack.com/redirect/18408097-2ca8-4cf8-ba3a-e575516e3de3?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• AI Eats the World: https://youtu.be/niJpDnNtNp4 [ https://substack.com/redirect/34f4f239-0067-4c86-956e-981709b0e66f?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• VisiCalc: https://en.wikipedia.org/wiki/VisiCalc [ https://substack.com/redirect/a9386bf7-596d-4017-874e-f87217639db7?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• McKinsey & Company: https://www.mckinsey.com [ https://substack.com/redirect/c027e0ea-3dfd-41b2-97a1-929669058eb5?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Bain & Company: https://www.bain.com [ https://substack.com/redirect/e0bb3cf9-8595-4050-bfc3-e20d936cad00?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Accenture: https://www.accenture.com [ https://substack.com/redirect/e466a721-211e-4ae4-a08a-8b724639853f?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Jevons paradox: https://en.wikipedia.org/wiki/Jevons_paradox [ https://substack.com/redirect/6d535409-0894-40ff-a738-99108091a9f5?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Benedict’s post on LinkedIn about Excel: https://www.linkedin.com/posts/benedictevans_younger-people-may-not-believe-this-but-activity-7303217994459938816-PNqu [ https://substack.com/redirect/7b3fa33b-0efe-4d58-a2e9-c17392580680?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• The AI-native startup: 5 products, 7-figure revenue, 100% AI-written code | Dan Shipper (co-founder/CEO of Every): https://www.lennysnewsletter.com/p/inside-every-dan-shipper [ https://substack.com/redirect/6feb0478-f0bb-446e-9d5a-b291e817dd9c?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Dario Amodei on X: https://x.com/DarioAmodei [ https://substack.com/redirect/bc626a48-0135-470a-b90a-f5c3e1924897?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Marc Andreessen: The real AI boom hasn’t even started yet: https://www.lennysnewsletter.com/p/marc-andreessen-the-real-ai-boom [ https://substack.com/redirect/33baaca7-eaa9-404c-a5f5-fd36ca56cd18?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Frame.io: https://frame.io [ https://substack.com/redirect/a74eb810-3f0d-427f-85ec-fe370cdb1a67?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Food Marketing Institute: https://en.wikipedia.org/wiki/Food_Marketing_Institute [ https://substack.com/redirect/da219b0b-2a04-49a6-8d8c-9ed44d0f7b34?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Llama: https://www.llama.com [ https://substack.com/redirect/e235bf99-0168-459f-86e8-0dc49f2ab067?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Steven Sinofsky on X: https://x.com/stevesi [ https://substack.com/redirect/ca4408a4-2b0e-44e5-b05a-68c96aa4ead0?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Drake meme: https://imgflip.com/memegenerator/343699919/Drake-Hotline-Bling-Transparent-Background [ https://substack.com/redirect/f5bc1a63-3df6-4a43-9c36-49f188738e2b?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Ex-Google CEO Gets Booed While Discussing AI in Commencement Speech | WSJ News: https://www.youtube.com/watch?v=tNH43a1EI7s [ https://substack.com/redirect/b6aea6de-39ec-4cd9-bd56-8790ea8c9c3a?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Jonathan Swift’s quote: https://www.goodreads.com/quotes/9838985-you-cannot-reason-a-person-out-of-a-position-he [ https://substack.com/redirect/ddd80992-3f6a-44e6-89a7-e21b322c6292?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• George Carlin’s quote: https://www.brainyquote.com/quotes/george_carlin_391403 [ https://substack.com/redirect/c7adf764-2aea-46cc-a218-f549a685a384?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Fujitsu: https://global.fujitsu [ https://substack.com/redirect/bcc08169-c23c-403e-9b74-b13ff4daa9ff?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• O*NET OnLine: https://www.onetonline.org [ https://substack.com/redirect/df02bfd7-f3a9-444e-baf3-bded4f4503e9?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Pete Holmes’s website: https://peteholmes.com [ https://substack.com/redirect/3a29b253-6360-4823-866e-7d0831ccc433?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• The Seventh Seal: https://www.imdb.com/title/tt0050976 [ https://substack.com/redirect/394e4cce-1f91-47d3-bae1-e71a4a886ae0?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Ericsson R310s phone: https://en.wikipedia.org/wiki/Ericsson_R310s [ https://substack.com/redirect/0b455745-b440-4dc3-93f3-441f4804f9d6?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• i-mate phone: https://en.wikipedia.org/wiki/I-mate [ https://substack.com/redirect/a2cc847b-11bc-4393-a390-a3d95d3b6c50?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• J-Phone: https://www.mobilephonemuseum.com/phone-detail/j-phone-j-t06 [ https://substack.com/redirect/03421cd9-baf2-47bc-a94f-c33be1ede085?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Recommended books:
• Three Men in a Boat: https://www.amazon.com/Three-Men-Boat-Jerome-K/dp/1512099899 [ https://substack.com/redirect/ffe2d8e5-6f8a-48e0-8c3f-2d7d3ee0ebbd?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Nature’s Metropolis: Chicago and the Great West: https://www.amazon.com/Natures-Metropolis-Chicago-Great-West/dp/0393308731 [ https://substack.com/redirect/528ba7d8-1dce-4f2e-99f3-9b9c26a0ed5c?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• The Lord of the Rings: https://www.amazon.com/Lord-Rings-Boxed-Set/dp/0358439191 [ https://substack.com/redirect/3e11d84a-9419-49a1-b365-c2914d394931?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Production and marketing by https://penname.co/ [ https://substack.com/redirect/c64411ca-967b-4504-8d25-b0f6b1a3fadc?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com [ mailto:podcast@lennyrachitsky.com ].
Lenny may be an investor in the companies discussed.
My biggest takeaways from this conversation:...
Unsubscribe https://substack.com/redirect/2/eyJlIjoiaHR0cHM6Ly93d3cubGVubnlzbmV3c2xldHRlci5jb20vYWN0aW9uL2Rpc2FibGVfZW1haWw_dG9rZW49ZXlKMWMyVnlYMmxrSWpvME1qWTFNVFV3TkRBc0luQnZjM1JmYVdRaU9qRTVPRFU1TVRrd055d2lhV0YwSWpveE56Z3dNak14TkRjMkxDSmxlSEFpT2pFNE1URTNOamMwTnpZc0ltbHpjeUk2SW5CMVlpMHhNRGcwTlNJc0luTjFZaUk2SW1ScGMyRmliR1ZmWlcxaGFXd2lmUS4tMFpoMlAzYjNFWTNpM01zUnNvd2ZjcXdxQVRvQ0pMeE5tSTB3Ym5qR2cwIiwicCI6MTk4NTkxOTA3LCJzIjoxMDg0NSwiZiI6dHJ1ZSwidSI6NDI2NTE1MDQwLCJpYXQiOjE3ODAyMzE0NzYsImV4cCI6MjA5NTgwNzQ3NiwiaXNzIjoicHViLTAiLCJzdWIiOiJsaW5rLXJlZGlyZWN0In0.4WuBP6-R50fDVyvsOm6gED5fJ31qi2SKJFOJ7aG1-Z4?
View Email
A rational conversation on where AI is actually going | Benedict Evans
lenny@substack.com5/31/2026
SubstackView this post on the web at https://www.lennysnewsletter.com/p/essential-books-for-product-builderspart
👋 Hey there, I’m Lenny. Each week, I write about building product, driving growth, and accelerating your career. For more: Lenny’s Podcast [ https://substack.com/redirect/1a5e2633-096b-4643-9b4d-e5c4aec62407?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] | Lennybot [ https://substack.com/redirect/213f4be5-8330-4e2c-bd80-0483ccf2d0be?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] | How I AI [ https://substack.com/redirect/e9486ea0-fd96-4ab5-8eb7-f2c63f2d16aa?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] | My favorite AI/PM courses [ https://substack.com/redirect/f5e21845-f48f-4eaf-9ed5-b1f37a4f5f8b?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], public speaking course [ https://substack.com/redirect/22d5444b-632f-4f4b-ae16-9586bef4752f?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], and interview prep copilot [ https://substack.com/redirect/07d48c03-8a7f-438e-b972-bc7edcfc613a?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
P.S. Get a full free year of Cursor, Google AI, Lovable, Replit, Notion, Manus, Gamma, n8n, Canva, ElevenLabs, Factory, Wispr Flow, Fin, Supabase, Bolt, Linear, PostHog, Framer, Railway, Granola, Warp, Gumloop, Magic Patterns, Mobbin, Stripe Atlas, and ChatPRD, by becoming an Insider subscriber [ https://substack.com/redirect/f8000459-d184-4291-abb5-0350124d3aac?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]. Yes, this is for real.
I was a shy kid growing up, so I spent a lot of time reading books. I devoured sci-fi, non-fiction, and every programming book I could find. When the library didn’t have the C++ book I wanted, I taught myself to code by buying book after book from our local Borders (RIP). I was tearing through so many coding books that my dad started returning the ones I’d finished to the bookstore so that we could afford to buy more.
I’ve always thought it’s so cool that the smartest person in the world on a topic I care about spends 2+ years of their life distilling their best ideas into an enjoyable read, and I can get this for just $20. Amazing.
There’s endless free content flying at us hourly now—newsletters, podcasts, tweets, oh my—but how many blog posts or tweets have had anywhere near the lasting impact on your life as a great book?
To continue my essential-reads series (don’t miss part 1 [ https://substack.com/redirect/9346d411-240d-48e6-b569-f23069f0ad4c?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] and part 2 [ https://substack.com/redirect/183b649d-3795-4c86-b390-1ae56277278e?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] of my favorite online essays), I’ve put together a collection of my all-time favorite books, organized by their jobs-to-be-done. When your manager tells you to work on a particular development area—or if you’re just feeling the itch for self-improvement—these are the books I recommend you read.
To keep this list extremely high signal-to-noise, I forced myself to pick only three books per category (so hard!), and only books I’ve completed. I included both classics and under-the-radar gems. And I very much agree with Marc Andreessen’s take [ https://substack.com/redirect/a73168b8-46ae-407e-b0f0-b27cd82359df?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] that you should mostly read books that are over 10 years old (because those are the books that have stood the test of time), so you’ll notice very few new books.
There are so many great books that I didn’t include here, either because I haven’t had a chance to read them or they just didn’t make the cut. I’m sorry if I didn’t include your book, or a book you love. I probably forgot some important titles, too. That’s why we’ll have a part 2!
P.S. If you’re feeling like you have no time to read, I was in the same boat. Bryan Johnson’s suggestion [ https://substack.com/redirect/4f1516ac-76b7-4c90-965e-6c7f6a058c69?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] of reading a book for 10 minutes before bed changed my life. I started reading more books, and I got better sleep! Try it out.
I want to improve my communication skills
I had never written anything online before starting this newsletter, so once I realized this was going to be a thing, I decided I needed to learn something about writing. Friends recommended many different books, and I read them all. But these three had the most practical, impactful, and lasting advice, which is still lodged in my head even now.
Nobody Wants to Read Your Sh*t [ https://substack.com/redirect/b14f03e5-4922-4737-abd4-41e189c98ffa?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] by Steven Pressfield
On Writing Well [ https://substack.com/redirect/430f604d-3674-4aa6-a3bb-a2fd36a0daf2?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] by William Zinsser
Storyworthy [ https://substack.com/redirect/4aa3ad12-5b04-4207-b73e-8992cc6e09b8?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] by Matthew Dicks
Check out my conversation with Matthew Dicks [ https://substack.com/redirect/f54bb8c8-b9d7-401b-a02a-54b48f696ae9?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ].
I want to get better at executing
If you love this newsletter, you crave actionable, tactical advice and frameworks that you can put into practice immediately. The first two books will give you exactly that, and the third will give you a meta-framework that’ll level up how you approach everything at work.
The Great CEO Within [ https://substack.com/redirect/4eb3c627-a617-4242-9986-267a71f17dce?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] by Matt Mochary
Scaling People [ https://substack.com/redirect/2001a13a-cc6d-4e13-b9be-e3dbfb524035?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] by Claire Hughes Johnson
The Goal [ https://substack.com/redirect/3d31fa19-69dc-42ef-a74b-8efba9446d10?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] by Eliyahu Goldratt
Check out my conversations with Matt Mochary [ https://substack.com/redirect/3bc5989d-c3ce-4ae9-8b8c-c1ea6245a568?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] and Claire Hughes Johnson [ https://substack.com/redirect/f82d32d3-0381-4856-8a43-35ec6f65094f?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ].
I want to get better at strategy
I remember reading these books and feeling like, okay, I finally understand what “strategy” is.
Good Strategy/Bad Strategy [ https://substack.com/redirect/a82c9819-f5c8-48d9-ae93-cd5576c64a93?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] by Richard Rumelt
Playing to Win [ https://substack.com/redirect/9a02b418-104d-4e09-87bd-5a16b96142e8?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] by Roger L. Martin
Working Backwards [ https://substack.com/redirect/ce8f3657-895e-4bd0-8b6a-f46d115ab20d?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] by Colin Bryar and Bill Carr
Check out my conversations with Richard Rumelt [ https://substack.com/redirect/2eb90023-89f7-42ae-bc41-db5a90ede159?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], Roger Martin [ https://substack.com/redirect/123e77a9-8523-4239-ad43-3ce5d6252908?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], and Bill Carr [ https://substack.com/redirect/db9e3a26-b29c-4d53-8e0b-92c59cab8eef?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ].
I want to be inspired to build something great
This bucket of books might be my favorite of the bunch. They showed me how much a singular (relentless) mind can accomplish. Read them, and you’ll be ready to run through walls.
The Making of Prince of Persia [ https://substack.com/redirect/dd8ae2ce-dcc2-4e7a-bb72-ce03ef843b69?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] by Jordan Mechner
Build [ https://substack.com/redirect/e186b988-9078-49ac-a57c-4a1f1444bdcd?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] by Tony Fadell
Shoe Dog [ https://substack.com/redirect/fe3152d6-68e9-486c-867a-6518f2d06058?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] by Phil Knight
I want to become a better manager
These books are among the most mentioned on my podcast. I remember reading High Output Management when I was a baby manager, and it finally taught me what my job actually was. The Making of a Manager is the modern version of that book. And Radical Candor forever shifted how I think about hard feedback.
High Output Management [ https://substack.com/redirect/58fbd63c-6dae-4cbc-8e47-c366d5600a9e?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] by Andy Grove
The Making of a Manager [ https://substack.com/redirect/75a319ec-bc90-4a90-9501-b1372e6b0fb2?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] by Julie Zhuo
Radical Candor [ https://substack.com/redirect/2ea656e2-156e-4ad6-99fd-1ce4f291386c?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] by Kim Scott
Check out my conversations with Kim Scott [ https://substack.com/redirect/c88b7f0f-33e8-4815-ae9e-ea529cdee8a9?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] and Julie Zhuo [ https://substack.com/redirect/d1b2eb03-e88d-4123-b95f-c78767bd6949?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ].
I want to become a better leader
I love how the combination of these three books sums up great leadership: push people to do the best work of their lives, but be human about it, and, in the end, the score will take care of itself.
Amp It Up [ https://substack.com/redirect/f152d33e-24f9-43f7-beaa-aef9af3ad8a2?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] by Frank Slootman
The 15 Commitments of Conscious Leadership [ https://substack.com/redirect/95f1d33b-daa1-4804-a1ea-da6107f61e9e?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] by Jim Dethmer, Diana Chapman, and Kaley Klemp
The Score Takes Care of Itself [ https://substack.com/redirect/03a4ecbb-cb9c-424a-ae16-f20c3e25bbe1?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] by Bill Walsh
I want to increase my product success rate
These classics taught me the fundamentals of product management: talking to customers, prioritizing roadmaps, and what it takes to build something valuable and impactful.
The Mom Test [ https://substack.com/redirect/341013c5-d1cb-4c35-9a83-ffb0c5ab9e47?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] by Rob Fitzpatrick
Escaping the Build Trap [ https://substack.com/redirect/663b8106-7b77-49a0-abdd-f59b050b5524?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] by Melissa Perri
Continuous Discovery Habits [ https://substack.com/redirect/badb9fa9-cd77-478b-89d8-ff9c7f00fa71?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] by Teresa Torres
Check out my conversations with Melissa Perri [ https://substack.com/redirect/4a601b99-9f00-4805-99f2-667e4068bacf?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] and Teresa Torres [ https://substack.com/redirect/e2721076-5d0b-4931-b699-a3c063b90f97?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ].
I want to level up my product org
These books are also some of the most mentioned on my podcast, because they’ll shift how you think about the role of product within your organization, and how to make decisions in uncertain environments.
Empowered [ https://substack.com/redirect/c5fb45b7-d026-4683-8795-1799b001bbb6?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] by Marty Cagan
Inspired [ https://substack.com/redirect/2991cf78-e113-4f31-a71b-0c97de5a234a?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] by Marty Cagan
Thinking in Bets [ https://substack.com/redirect/4d0592df-0230-4d85-bd6a-97e77b382f3c?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] by Annie Duke
Check out my conversations with Marty Cagan [ https://substack.com/redirect/1a2ea4cb-abee-4323-b032-072711de9cb1?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] (and, again, Marty Cagan [ https://substack.com/redirect/afbfc599-2ccf-4952-bc24-de39d96a5363?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]) and Annie Duke [ https://substack.com/redirect/1961613c-24cc-469e-bc2a-a5e979d3a292?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ].
I want to get better at sales and marketing
With AI making it easier to build, distribution is becoming the bigger bottleneck. This is not a natural strength for most builders, which is why you need to develop your marketing and sales muscle. I learned more about marketing and sales from these three books than from anywhere else.
Purple Cow [ https://substack.com/redirect/2189da94-8106-4ee2-beae-c8e8c25c4b7c?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] by Seth Godin
Obviously Awesome [ https://substack.com/redirect/1b218b56-25ff-4e9e-83c4-2ec95374e383?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] by April Dunford
Founding Sales [ https://substack.com/redirect/6a4645ef-fd58-4520-b407-ff4d42fcc92d?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] by Peter Kazanjy
Check out my conversations with Seth Godin [ https://substack.com/redirect/aa7da5b1-47de-465e-94ca-139dfda3dca5?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], April Dunford [ https://substack.com/redirect/3bc45cc8-1237-4bba-84bb-6690a3236504?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], and Peter Kazanjy [ https://substack.com/redirect/16412231-3c82-44f5-b99e-9f9ace815b28?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ].
I want to be more productive...
Unsubscribe https://substack.com/redirect/2/eyJlIjoiaHR0cHM6Ly93d3cubGVubnlzbmV3c2xldHRlci5jb20vYWN0aW9uL2Rpc2FibGVfZW1haWw_dG9rZW49ZXlKMWMyVnlYMmxrSWpvME1qWTFNVFV3TkRBc0luQnZjM1JmYVdRaU9qRTVPRFU1TkRFek9Dd2lhV0YwSWpveE56YzVPREE1T0RZeUxDSmxlSEFpT2pFNE1URXpORFU0TmpJc0ltbHpjeUk2SW5CMVlpMHhNRGcwTlNJc0luTjFZaUk2SW1ScGMyRmliR1ZmWlcxaGFXd2lmUS4yNGtETHI1RndPVDlfWEVoNUstSENPWFYyWEhQZUlyckxzalRLYnVVLTVRIiwicCI6MTk4NTk0MTM4LCJzIjoxMDg0NSwiZiI6dHJ1ZSwidSI6NDI2NTE1MDQwLCJpYXQiOjE3Nzk4MDk4NjIsImV4cCI6MjA5NTM4NTg2MiwiaXNzIjoicHViLTAiLCJzdWIiOiJsaW5rLXJlZGlyZWN0In0.WHocyKUR_oC_u7SeURQWYbNJQrg7WwZe-lXVRQEEzB8?
View Email
Essential books for product builders—part 1
lenny@substack.com5/26/2026
SubstackView this post on the web at https://www.lennysnewsletter.com/p/the-ai-paradox-dan-shipper
Dan Shipper is the co-founder and CEO of Every, a media and software company that’s become a living laboratory for the future of work. Everyone at his company of about 30 people is an AI early adopter; from editors to ops people, they use AI to do much of their work, giving Every a unique lens into where the world is heading. A year ago on this show, Dan predicted that people were sleeping on Claude Code for nontechnical work, which proved to be remarkably prescient. Today he’s back with another set of calls: the SaaS apocalypse is dumb, CLIs are over, the forward deployed engineer is the most valuable new hire, and the only thing you need to do to stay employed is ride the models.
Listen on YouTube [ https://substack.com/redirect/39cc51c4-7a79-4042-a798-7e11fc1c5222?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], Spotify [ https://substack.com/redirect/7fa5e14c-6b01-408c-bac9-77c0381031d5?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], and Apple Podcasts [ https://substack.com/redirect/aba475e2-2818-4361-89f4-bdfa426d44a1?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Dan’s predictions:
The future of work will happen inside Codex or Claude Code.
Every company will have one “super-agent” inside their Slack that every employee talks to regularly.
SaaS is not dead—in fact, Dan is bullish on SaaS stocks. His contrarian take: “I would buy SaaS stocks right now.”
SaaS economics will shift: users will bring their own AI tokens into apps, which actually improves SaaS margins.
PMs will thrive in the AI era.
Full-stack designers will become superheroes.
The AI job apocalypse is not happening.
Forward deployed engineer is the new most essential role.
CLIs are over.
Automation is a lie.
We will read way more AI-generated writing and we will like it.
We’ll be building software for humans and agents to use together.
Brought to you by:
WorkOS [ https://substack.com/redirect/8b093ac3-9704-4395-8760-e4a81d20e02c?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]—Make your app enterprise-ready, with SSO, SCIM, RBAC, and more
Vanta [ https://substack.com/redirect/56b1ca3d-9422-49f8-9832-121604329a0e?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]—Automate compliance, manage risk, and accelerate trust with AI
Where to find Dan Shipper:
• X: https://x.com/danshipper [ https://substack.com/redirect/080eb75b-76ea-417d-8700-d860c32d0d90?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• LinkedIn: https://www.linkedin.com/in/danshipper/ [ https://substack.com/redirect/65ddde7c-8eb3-45b6-bad6-a360aab14d9e?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Podcast: https://every.to/podcast [ https://substack.com/redirect/aca487de-a685-4965-86e2-6688aa5d9440?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Website: https://danshipper.com [ https://substack.com/redirect/d5e377cf-6a29-45ca-afd4-7381bb62220a?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Referenced:
• The AI-native startup: 5 products, 7-figure revenue, 100% AI-written code | Dan Shipper (co-founder/CEO of Every): https://www.lennysnewsletter.com/p/inside-every-dan-shipper [ https://substack.com/redirect/41738a1c-9263-4948-bf7d-210efe14f064?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Claude Cowork: https://claude.com/product/cowork [ https://substack.com/redirect/f7463f1b-c13b-4330-8a88-00498ad804a4?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Codex: https://chatgpt.com/codex [ https://substack.com/redirect/0462491f-0141-4a70-a8b6-26ab49d6244d?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Everyone should be using Claude Code more: https://www.lennysnewsletter.com/p/everyone-should-be-using-claude-code [ https://substack.com/redirect/d5c5fde8-03a4-40e5-bbe1-2aa6dc6d9911?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Every: https://every.to [ https://substack.com/redirect/824ca165-0902-4aba-9c98-ca71975aba89?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Kieran Klaassen on X: https://x.com/kieranklaassen [ https://substack.com/redirect/26930081-484c-417b-8d82-a7fc9e4398d2?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Cora: https://cora.computer [ https://substack.com/redirect/689adfdb-5462-4db9-92b1-7a99436bb650?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Kate Lee: https://every.to/@kate_1767 [ https://substack.com/redirect/61996acb-3a24-4502-b30b-cdb0c60fa443?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• METR (Model Evaluation and Threat Research): https://metr.org [ https://substack.com/redirect/0f40474e-fb15-4030-8de1-12217590e449?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• OpenClaw: https://openclaw.ai [ https://substack.com/redirect/73345d18-dcf8-4e5f-ad1b-f56e44d553a8?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Shopify: https://www.shopify.com [ https://substack.com/redirect/ea3bed8d-9586-4a3c-9f81-7f167df125d4?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Ramp: https://ramp.com [ https://substack.com/redirect/04f961b8-3f0b-41d3-a68a-e2cd257d7fe6?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Brandon Gell on LinkedIn: linkedin.com/in/brandongell [ https://substack.com/redirect/ec946b18-4576-4d6f-bc24-dad8a240b5cb?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Proof: https://every.to/on-every/introducing-proof [ https://substack.com/redirect/8331bc25-01cf-4574-8125-f453dbff1a22?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Devin: https://devin.ai [ https://substack.com/redirect/dfaf4710-b46f-41c7-b853-c75e0215e9e0?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Cursor: https://cursor.com [ https://substack.com/redirect/6c9b87ca-8f16-46cc-96a0-e2ed0adbbbec?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• The rise of Cursor: The $300M ARR AI tool that engineers can’t stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell [ https://substack.com/redirect/10ee8e37-c7c7-490b-9563-4ad53bd3df37?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• SpaceX: https://www.spacex.com [ https://substack.com/redirect/56a35b82-d39e-4451-8a81-d4391c333624?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• GitHub: https://github.com [ https://substack.com/redirect/74254852-a0d6-4e55-9fd0-31ee95b7d2ae?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Lenny’s post on X on AI changing job responsibilities: https://x.com/lennysan/status/2054664138039992600 [ https://substack.com/redirect/b5b71192-3d42-439e-a11d-b35b695d67e7?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• General Assembly: https://generalassemb.ly [ https://substack.com/redirect/3338f304-8e7f-48f3-b4ae-84ffd14be1df?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Marcus Moretti: https://every.to/@marcus_fd8302_1 [ https://substack.com/redirect/fe8b86af-e829-462e-873c-7b7358c2465b?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Spiral: https://every.to/on-every/introducing-spiral [ https://substack.com/redirect/90577f67-3d9d-49d5-b307-8d9da80296f5?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Axios: https://www.axios.com [ https://substack.com/redirect/dca54e37-7f52-4916-93dd-4e0108ebe36c?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Hermes: https://hermes-agent.nousresearch.com [ https://substack.com/redirect/d8e2f3a1-f221-4565-ab3e-913d9956c9c1?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Viktor: https://www.viktor.ai [ https://substack.com/redirect/d216f642-7e14-46ef-b189-04361e5783de?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• The Dark Wizard on HBO: https://www.hbomax.com/shows/dark-wizard/76e78c26-21c9-45b4-b84b-4c3e1f8ff763 [ https://substack.com/redirect/72527f2c-e3d8-40d0-a8f6-4e6c8793870a?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Alex Honnold: https://en.wikipedia.org/wiki/Alex_Honnold [ https://substack.com/redirect/9237537d-60ad-4e50-9c32-7552cf8a8038?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• 100 Foot Wave on HBO Max: https://www.hbomax.com/shows/100-foot-wave/34e489ad-2eca-4078-adb6-6d2b521b407e [ https://substack.com/redirect/0f308897-2399-4df6-aac8-6cafe3f02225?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Rob Burbea talks: https://www.youtube.com/@boubabuddha/playlists [ https://substack.com/redirect/b1b6f554-d19e-4717-85cf-bd5ad9c0a8dc?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• David Goggins: https://en.wikipedia.org/wiki/David_Goggins [ https://substack.com/redirect/19182a50-6950-4a17-8e19-e159337983b1?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Recommended books:
• The Golden Compass: https://www.amazon.com/Golden-Compass-His-Dark-Materials/dp/0807204714 [ https://substack.com/redirect/d8830d31-d6d9-4dd0-af0d-d8772b43c180?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• The Writing Life: https://www.amazon.com/Writing-Life-Annie-Dillard/dp/0060919884 [ https://substack.com/redirect/635d3fc6-90ac-4e1c-a6f9-d6ca5e4df7bd?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• The Second World War: https://www.amazon.com/Second-World-War-Volumes/dp/B005NS30ZG [ https://substack.com/redirect/e3405965-7ba3-4a31-b668-788cb97cfe83?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• The Rigor of Angels: Borges, Heisenberg, Kant, and the Ultimate Nature of Reality: https://www.amazon.com/Rigor-Angels-Heisenberg-Ultimate-Reality/dp/0593315073 [ https://substack.com/redirect/59eed193-9207-428e-be01-48908931c1df?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• The Power Broker: Robert Moses and the Fall of New York: https://www.amazon.com/Power-Broker-Robert-Moses-Fall/dp/0394720245 [ https://substack.com/redirect/839be43c-98c2-4ae5-a6f9-81c57b764930?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Production and marketing by https://penname.co/ [ https://substack.com/redirect/71e368ab-5343-47f2-ac95-a5c8038ade1b?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com [ mailto:podcast@lennyrachitsky.com ].
Lenny may be an investor in the companies discussed.
My biggest takeaways from this conversation:...
Unsubscribe https://substack.com/redirect/2/eyJlIjoiaHR0cHM6Ly93d3cubGVubnlzbmV3c2xldHRlci5jb20vYWN0aW9uL2Rpc2FibGVfZW1haWw_dG9rZW49ZXlKMWMyVnlYMmxrSWpvME1qWTFNVFV3TkRBc0luQnZjM1JmYVdRaU9qRTVOelF4TlRFMk9Td2lhV0YwSWpveE56YzVOakkyTmpjM0xDSmxlSEFpT2pFNE1URXhOakkyTnpjc0ltbHpjeUk2SW5CMVlpMHhNRGcwTlNJc0luTjFZaUk2SW1ScGMyRmliR1ZmWlcxaGFXd2lmUS5Fbkp2VHRZZm1rUmUyQjBORFNyV0xGdkZYZXd0bnhRZUp6UXNpd1ZBQk1vIiwicCI6MTk3NDE1MTY5LCJzIjoxMDg0NSwiZiI6dHJ1ZSwidSI6NDI2NTE1MDQwLCJpYXQiOjE3Nzk2MjY2NzcsImV4cCI6MjA5NTIwMjY3NywiaXNzIjoicHViLTAiLCJzdWIiOiJsaW5rLXJlZGlyZWN0In0.OSChmShFolohI78BG_EVvd8oow3dRsvqMd8N0-Lle4k?
View Email
The AI paradox: More automation, more humans, more work | Dan Shipper
lenny@substack.com5/24/2026
SubstackView this post on the web at https://www.lennysnewsletter.com/cp/198757689
Unsubscribe https://substack.com/redirect/2/eyJlIjoiaHR0cHM6Ly93d3cubGVubnlzbmV3c2xldHRlci5jb20vYWN0aW9uL2Rpc2FibGVfZW1haWw_dG9rZW49ZXlKMWMyVnlYMmxrSWpvME1qWTFNVFV3TkRBc0luQnZjM1JmYVdRaU9qRTVPRGMxTnpZNE9Td2lhV0YwSWpveE56YzVNemswTmpFNExDSmxlSEFpT2pFNE1UQTVNekEyTVRnc0ltbHpjeUk2SW5CMVlpMHhNRGcwTlNJc0luTjFZaUk2SW1ScGMyRmliR1ZmWlcxaGFXd2lmUS41YUl0NUpFblkycFVLU051dER6ZHUxNThaeTFkSXJmZVU4S0QwcXNjWGNrIiwicCI6MTk4NzU3Njg5LCJzIjoxMDg0NSwiZiI6dHJ1ZSwidSI6NDI2NTE1MDQwLCJpYXQiOjE3NzkzOTQ2MTgsImV4cCI6MjA5NDk3MDYxOCwiaXNzIjoicHViLTAiLCJzdWIiOiJsaW5rLXJlZGlyZWN0In0.g72tDoETq3xZ6N-jisEuyYkBr7sTAi-nnh2L6aa2dOs?
View Email
You’ll lose your job in 2027.
lenny@substack.com5/21/2026
SubstackView this post on the web at https://www.lennysnewsletter.com/cp/198576886
Unsubscribe https://substack.com/redirect/2/eyJlIjoiaHR0cHM6Ly93d3cubGVubnlzbmV3c2xldHRlci5jb20vYWN0aW9uL2Rpc2FibGVfZW1haWw_dG9rZW49ZXlKMWMyVnlYMmxrSWpvME1qWTFNVFV3TkRBc0luQnZjM1JmYVdRaU9qRTVPRFUzTmpnNE5pd2lhV0YwSWpveE56YzVNamt5TWprekxDSmxlSEFpT2pFNE1UQTRNamd5T1RNc0ltbHpjeUk2SW5CMVlpMHhNRGcwTlNJc0luTjFZaUk2SW1ScGMyRmliR1ZmWlcxaGFXd2lmUS5wUGYwY09mRU1xUHBXZE14X1BPUlVOZG8tMUIwdXp6N0g3VUVBb04yMlc4IiwicCI6MTk4NTc2ODg2LCJzIjoxMDg0NSwiZiI6dHJ1ZSwidSI6NDI2NTE1MDQwLCJpYXQiOjE3NzkyOTIyOTMsImV4cCI6MjA5NDg2ODI5MywiaXNzIjoicHViLTAiLCJzdWIiOiJsaW5rLXJlZGlyZWN0In0.gi03ugAumJ11gpecD9pLjBIvRhh3vWR56dUbLkdgMjo?
View Email
10 Job-Search Rules That Just Broke
lenny@substack.com5/20/2026
SubstackView this post on the web at https://www.lennysnewsletter.com/p/the-lenny-and-friends-summit-is-back
👋 Hey there, I’m Lenny. Each week, I answer reader questions about building product, driving growth, and accelerating your career. For more: Lenny’s Podcast [ https://substack.com/redirect/037128ee-a4c6-456a-b63c-78e76ca18d1a?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] | Lennybot [ https://substack.com/redirect/65f316f5-4fbe-4a12-9624-0fe4519618d7?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] | How I AI [ https://substack.com/redirect/29762f5c-5296-4062-9393-025616492a87?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] | My favorite AI/PM courses [ https://substack.com/redirect/a7ed9958-e845-45dd-bf2a-9cbe38b78d21?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], public speaking course [ https://substack.com/redirect/3d209740-41ef-4931-8df7-5734f2b7e1f7?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], and interview prep copilot [ https://substack.com/redirect/27fa70ce-0c1b-4b52-aa92-b05bb23a95a1?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Two years ago, we held the first-ever Lenny and Friends Summit. It was one of the most meaningful days of my life. Full of in-depth talks, intimate roundtables, and a lot of human connection. At the end of the day, an attendee handed me this note before quickly walking away:
There’s such power in IRL events, especially these days and especially for product leaders, who often lack peers they can be real with. Ever since the first summit, I’ve been getting messages about how much y’all want another event like this.
Today, I’m excited to share that the Lenny and Friends Summit [ https://substack.com/redirect/dac40c32-f573-41d3-bbd8-d915daa5c2cd?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] returns on Thursday, September 10, in San Francisco! Apply now [ https://substack.com/redirect/dac40c32-f573-41d3-bbd8-d915daa5c2cd?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ].
My vision is to make this the best product event in the world. We’re keeping it intentionally small—every attendee will be handpicked—and along with in-depth talks from the world’s top operators, we’ll have interactive workshops, tons of opportunities to get to know other attendees, and a few fun surprises.
My three main goals for this summit are to help you:
Deeply understand where the product role is heading
Learn tangible skills to thrive in that future
Build lasting connections with other world-class leaders
Here’s the initial lineup of speakers, each of whom has a unique lens into the future of building (with more to be announced soon):
Given that we’re expecting lots of interest and the venue has limited capacity, we’re asking people to apply to attend [ https://substack.com/redirect/dac40c32-f573-41d3-bbd8-d915daa5c2cd?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]. Paid newsletter subscribers will get priority consideration. This summit is for senior product and AI leaders; typical titles include Chief, VP, Director, Senior, Group, Lead, or Principal.
If you’re just starting your career in product or growth, the content won’t be as relevant for you. I may host a future event geared toward early-career folks.
To give you a sense of what the last summit felt like, a few messages I got from attendees last year:
“The highest-ROI networking event I have been to.” —Senior PM
“Every aspect of the event was absolutely remarkable.” —CPO
“So many insightful discussions, learnings, and connections, and many tactical takeaways I plan to immediately put in practice.” —Product Lead
“The hit rate of good talks was higher than at any other conference I’ve been to.” —Sr. Director of Product
“A powerful reminder of why I fell in love with building products.” —Founder
Finally, some of my favorite moments from the day:
I’m so excited to be doing this again. Whether you made it to the first summit or missed the chance then, we’ve put a lot of thought into making this one even better: more hands-on workshops, more opportunities to meet other attendees, and more options for how to spend your day.
See you there!
Any questions? Please email info@lennyssummit.com [ mailto:info@lennyssummit.com ], and we’ll do our best to reply promptly.
If you’re finding this newsletter valuable, share it with a friend, and consider subscribing if you haven’t already. There are group discounts [ https://substack.com/redirect/455b7c89-7ccb-4ad7-8c5b-81e34856e9e4?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], gift options [ https://substack.com/redirect/e01df672-805a-494d-a9d1-1035ae46245b?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], and referral bonuses [ https://substack.com/redirect/b03e83e6-0f4c-45b1-a07e-ebae6f12bf68?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] available.
Sincerely,
Lenny 👋
Unsubscribe https://substack.com/redirect/2/eyJlIjoiaHR0cHM6Ly93d3cubGVubnlzbmV3c2xldHRlci5jb20vYWN0aW9uL2Rpc2FibGVfZW1haWw_dG9rZW49ZXlKMWMyVnlYMmxrSWpvME1qWTFNVFV3TkRBc0luQnZjM1JmYVdRaU9qRTVOekkzTWpFME5pd2lhV0YwSWpveE56YzVNakExTVRNMkxDSmxlSEFpT2pFNE1UQTNOREV4TXpZc0ltbHpjeUk2SW5CMVlpMHhNRGcwTlNJc0luTjFZaUk2SW1ScGMyRmliR1ZmWlcxaGFXd2lmUS56Vm1GQWJydnIyazFZRXJSZWR3RnBtWGxEaDV0cVJiN0o3c3NJVDRBVl93IiwicCI6MTk3MjcyMTQ2LCJzIjoxMDg0NSwiZiI6dHJ1ZSwidSI6NDI2NTE1MDQwLCJpYXQiOjE3NzkyMDUxMzYsImV4cCI6MjA5NDc4MTEzNiwiaXNzIjoicHViLTAiLCJzdWIiOiJsaW5rLXJlZGlyZWN0In0.S32FXerLvuiZor1kbEV5bfnr-Eerjv4ZvTDQ2bdNiRY?
View Email
The Lenny and Friends Summit is back!
lenny@substack.com5/19/2026
SubstackView this post on the web at https://www.lennysnewsletter.com/p/why-were-at-the-beginning-of-the
Caitlin Kalinowski is the former head of robotics and consumer hardware at OpenAI, helped design the MacBook Pro and MacBook Air at Apple, and led the AR and VR hardware teams at Meta. She’s designed and engineered some of the hardest and most beloved consumer hardware products in history and is now focused on the next frontier: robotics.
Listen on YouTube [ https://substack.com/redirect/278ed9fa-5758-4eb6-8794-9d7ba6fc2af7?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], Spotify [ https://substack.com/redirect/b70eb681-d0f6-4dac-81c5-6213042767d7?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], and Apple Podcasts [ https://substack.com/redirect/b5a2eca3-b2be-463d-9e4c-5e17bf5e4978?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
In our in-depth conversation, we discuss:
VR—what happened?
The coming memory price shock and why she’s telling startups to pre-buy now
How the technologies built for VR became the foundation of modern warfare
Why humanoid robots are still just prototypes, and what’s actually gating mass deployment
Lessons from Steve Jobs, Mark Zuckerberg, and Sam Altman
Why she left OpenAI
Brought to you by:
WorkOS [ https://substack.com/redirect/3649e27c-842d-4530-9a57-5cd258e0ffcc?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]—Make your app enterprise-ready, with SSO, SCIM, RBAC, and more
Vanta [ https://substack.com/redirect/15e4d36f-96ca-41fc-a9ca-3d8733a25d95?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]—Automate compliance, manage risk, and accelerate trust with AI
Where to find Caitlin Kalinowski:
• X: https://x.com/kalinowski007 [ https://substack.com/redirect/bcedc502-fd3b-4f35-9179-4615e1db7667?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• LinkedIn: https://www.linkedin.com/in/ckalinowski [ https://substack.com/redirect/c8302038-eb1f-4070-b6ba-cd5dfd349179?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Website: https://www.caitlinkalinowski.com [ https://substack.com/redirect/181f34e2-33d4-401e-8ddf-6ea2e3ddf2cf?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Referenced:
• MacBook: https://www.apple.com/shop/buy-mac [ https://substack.com/redirect/afa5d83e-a30b-4e58-95df-6473c93b8036?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Brett Degner on LinkedIn: https://www.linkedin.com/in/brett-degner-a723594 [ https://substack.com/redirect/2a8ba1e8-21cb-4195-ba92-158f659963d3?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Apple Vision Pro: https://www.apple.com/apple-vision-pro [ https://substack.com/redirect/c5a4a874-0c7f-4cef-9263-2cc53648e28a?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Orion glasses: https://www.meta.com/emerging-tech/orion [ https://substack.com/redirect/88e75421-61f6-43e7-867c-a23dcf9e46f5?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Marc Andreessen: The real AI boom hasn’t even started yet: https://www.lennysnewsletter.com/p/marc-andreessen-the-real-ai-boom [ https://substack.com/redirect/8b2fe215-a85a-4a09-9edf-927020930593?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Palmer Luckey on X: https://x.com/PalmerLuckey [ https://substack.com/redirect/76de423c-76ea-49a0-8f19-b14c670c0b6e?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Anduril: https://www.anduril.com [ https://substack.com/redirect/1a28b156-f49a-46b2-b3a5-cf159dd52006?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• OpenClaw: https://openclaw.ai [ https://substack.com/redirect/860cce94-463a-43f1-875e-413c2afedb6c?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Moltbook: https://www.moltbook.com [ https://substack.com/redirect/9d7e9816-45b0-4dd6-b56c-7135f0a00369?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Nat Friedman on X: https://x.com/natfriedman [ https://substack.com/redirect/4f499817-410a-49a0-9a64-e669e639dc17?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Shelly Goldberg on LinkedIn: https://www.linkedin.com/in/shelly-goldberg-9b3b621 [ https://substack.com/redirect/57251a05-b02f-4b38-9327-a6dc0cfcb2cf?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Kate Bergeron on LinkedIn: https://www.linkedin.com/in/katebergeron [ https://substack.com/redirect/895ae760-f8d8-41ea-a4e7-19bfabe9b454?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Matic: https://maticrobots.com [ https://substack.com/redirect/84d0c8df-e644-494c-9fb6-d98ed023e019?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Mehul Nariyawala on X: https://x.com/mehul [ https://substack.com/redirect/f3ad37e7-45fc-4726-9235-498e04ab736e?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Tesla: https://www.tesla.com [ https://substack.com/redirect/3f8b1841-17aa-46aa-940c-b0d0a6328cf2?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Starlink: https://starlink.com [ https://substack.com/redirect/5f645ca3-7579-49f0-8a4f-87f2357c6f2c?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• The Godmother of AI on jobs, robots, and why world models are next | Dr. Fei-Fei Li: https://www.lennysnewsletter.com/p/the-godmother-of-ai [ https://substack.com/redirect/5e3b1483-3747-4586-86d4-339b21242c8d?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Why experts writing AI evals is creating the fastest-growing companies in history | Brendan Foody (CEO of Mercor): https://www.lennysnewsletter.com/p/experts-writing-ai-evals-brendan-foody [ https://substack.com/redirect/f3962383-6cd3-45c4-abc0-bc1dcee57520?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• The 100-person AI lab that became Anthropic and Google’s secret weapon | Edwin Chen (Surge AI): https://www.lennysnewsletter.com/p/surge-ai-edwin-chen [ https://substack.com/redirect/6dbcaa2c-85f8-40af-8707-727eeecfa089?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Inside the expert network training every frontier AI model | Garrett Lord (Handshake CEO): https://www.lennysnewsletter.com/p/inside-handshake-garrett-lord [ https://substack.com/redirect/5ef66a96-48f3-4bfc-95af-c8d0edbf2b45?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Yelena Rachitsky on X: https://x.com/yelenart [ https://substack.com/redirect/5bf6ae15-548e-4f95-9982-a4fef768fff5?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Leila Takayama on LinkedIn: https://www.linkedin.com/in/leilatakayama [ https://substack.com/redirect/b9b5a88a-7c72-4e9a-8fe9-a8868562b974?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Pixar: https://www.pixar.com [ https://substack.com/redirect/93d72ba2-31ea-409e-9f10-280dac17b5b9?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Disney: https://www.disney.com [ https://substack.com/redirect/e111c616-3eff-4e16-b2ad-05cc57d78836?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Caitlin’s post on leaving OpenAI: https://x.com/kalinowski007/status/2030320074121478618 [ https://substack.com/redirect/92c9608a-5e2a-4a24-9e99-52dc274bd561?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Sam Altman on X: https://x.com/sama [ https://substack.com/redirect/9af17f7f-42be-44e7-94b6-3e5561b06631?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Jony Ive: https://en.wikipedia.org/wiki/Jony_Ive [ https://substack.com/redirect/420b8ff5-6b28-4ba7-ba94-c683629be651?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Mark Zuckerberg on Facebook: https://www.facebook.com/zuck [ https://substack.com/redirect/19d97974-69da-42d4-9f94-ba9e62276213?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Making Meta | Andrew ‘Boz’ Bosworth (CTO): https://www.lennysnewsletter.com/p/making-meta-andrew-boz-bosworth-cto [ https://substack.com/redirect/ec5716a4-423e-4021-9391-661a0c7f66e5?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Quest 2: https://en.wikipedia.org/wiki/Quest_2 [ https://substack.com/redirect/5f2d8296-608b-4f3f-8e14-e0f315810c80?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Euphoria on HBO Max: https://www.hbomax.com/shows/euphoria/4ffd33c9-e0d6-4cd6-bd13-34c266c79be0 [ https://substack.com/redirect/39ff237d-4313-4599-866a-f5ffc00c8681?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Vollebak: https://vollebak.com [ https://substack.com/redirect/8be88541-863c-4e02-80fe-d17250026d64?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Tim Urban’s post on X: https://x.com/waitbutwhy/status/1367871165319049221 [ https://substack.com/redirect/b63fd8dd-1c88-4427-a2ed-5c9baf6453f7?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Old Testament: https://en.wikipedia.org/wiki/Old_Testament [ https://substack.com/redirect/5f595c09-88fc-46d9-b499-d35f0ea33052?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Recommended books:
• Shadow & Claw (The Book of the New Sun, 1): https://www.amazon.com/Shadow-Claw-First-Half-Book/dp/1250781256 [ https://substack.com/redirect/d0fb0d07-3aa5-422e-ab7d-2c21b522d2ef?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Mrs. Dalloway: https://www.amazon.com/Mrs-Dalloway-VIRGINIA-WOOLF/dp/8175994215 [ https://substack.com/redirect/6a86595b-2ce6-4efc-b784-7ed43e35c693?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• The Histories: https://www.amazon.com/Histories-Herodotus/dp/0140449086 [ https://substack.com/redirect/7ea230d2-56e7-4ded-bdf3-e5ccb6b2b17e?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• The Epic of Gilgamesh: https://www.amazon.com/Epic-Gilgamesh/dp/014044100X [ https://substack.com/redirect/62338baf-fa88-49c8-8f17-0dfad8435802?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Production and marketing by https://penname.co/ [ https://substack.com/redirect/8c1a2f92-3ddf-4769-ae7e-4f1eacb2ae58?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com [ mailto:podcast@lennyrachitsky.com ].
Lenny may be an investor in the companies discussed.
My biggest takeaways from this conversation:...
Unsubscribe https://substack.com/redirect/2/eyJlIjoiaHR0cHM6Ly93d3cubGVubnlzbmV3c2xldHRlci5jb20vYWN0aW9uL2Rpc2FibGVfZW1haWw_dG9rZW49ZXlKMWMyVnlYMmxrSWpvME1qWTFNVFV3TkRBc0luQnZjM1JmYVdRaU9qRTVOalE0TXpjd01Td2lhV0YwSWpveE56YzVNREl4T0RZMkxDSmxlSEFpT2pFNE1UQTFOVGM0TmpZc0ltbHpjeUk2SW5CMVlpMHhNRGcwTlNJc0luTjFZaUk2SW1ScGMyRmliR1ZmWlcxaGFXd2lmUS5hbVhGcTl3aFU4LS1RZGlLMmo4TWg5TnpBbE50bkstN0VOOUlmYk9vU0FNIiwicCI6MTk2NDgzNzAxLCJzIjoxMDg0NSwiZiI6dHJ1ZSwidSI6NDI2NTE1MDQwLCJpYXQiOjE3NzkwMjE4NjYsImV4cCI6MjA5NDU5Nzg2NiwiaXNzIjoicHViLTAiLCJzdWIiOiJsaW5rLXJlZGlyZWN0In0.QEbcXH2yPja6H7exE0oJiA_9HHzkZtLNDMOIvVD3vbs?
View Email
Why we’re at the beginning of the AI hardware boom | Caitlin Kalinowski (ex–OpenAI, Meta, Apple)
lenny@substack.com5/17/2026
SubstackView this post on the web at https://www.lennysnewsletter.com/cp/197743912
Unsubscribe https://substack.com/redirect/2/eyJlIjoiaHR0cHM6Ly93d3cubGVubnlzbmV3c2xldHRlci5jb20vYWN0aW9uL2Rpc2FibGVfZW1haWw_dG9rZW49ZXlKMWMyVnlYMmxrSWpvME1qWTFNVFV3TkRBc0luQnZjM1JmYVdRaU9qRTVOemMwTXpreE1pd2lhV0YwSWpveE56YzROemcyTWpFeUxDSmxlSEFpT2pFNE1UQXpNakl5TVRJc0ltbHpjeUk2SW5CMVlpMHhNRGcwTlNJc0luTjFZaUk2SW1ScGMyRmliR1ZmWlcxaGFXd2lmUS44dlFaWjAzYXJXNl9KY3YyaUxfM2ttMTZJWXFPLWxSbEltVUhMTEtERFZVIiwicCI6MTk3NzQzOTEyLCJzIjoxMDg0NSwiZiI6dHJ1ZSwidSI6NDI2NTE1MDQwLCJpYXQiOjE3Nzg3ODYyMTIsImV4cCI6MjA5NDM2MjIxMiwiaXNzIjoicHViLTAiLCJzdWIiOiJsaW5rLXJlZGlyZWN0In0.jEcF9cmH6lnLLtJ-939p_VyLGz0HNEQpXy1PF2rWGik?
View Email
IC work is the new career flex
lenny@substack.com5/14/2026
SubstackView this post on the web at https://www.lennysnewsletter.com/p/how-to-build-a-company-that-withstands
Eric Ries is the author of The Lean Startup, a book that reshaped how a generation of founders think about building companies. His new book, Incorruptible, explains how successful companies are destroyed by failing to protect what makes them valuable, and how to change it.
Listen on YouTube [ https://substack.com/redirect/95fab009-4371-4c09-84d7-25b2ef7a325c?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], Spotify [ https://substack.com/redirect/c5416083-118e-4636-a890-001baa17be09?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], and Apple Podcasts [ https://substack.com/redirect/3f4e632d-6a2a-4827-a148-d7e0a5d9a1f6?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
In our in-depth conversation, we discuss:
Why 80% of venture-backed founders are ousted within three years of going public
The governance structures that protect companies like Anthropic, Costco, and Novo Nordisk
The simple legal filing that takes two pages and could save your company
Financial gravity: why successful companies predictably get corrupted into mediocrity
Why mission-aligned companies like Anthropic reap major benefits from protecting their mission through governance
Why success won’t protect you—it instead makes you a bigger target
Brought to you by:
WorkOS [ https://substack.com/redirect/9eba5ae3-b2c9-4bbc-8b45-d61ee043b276?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]—Make your app enterprise-ready, with SSO, SCIM, RBAC, and more
Vanta [ https://substack.com/redirect/7ff31c5b-2cf6-48c6-ab06-53445626ce4e?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]—Automate compliance, manage risk, and accelerate trust with AI
Where to find Eric Ries:
• X: https://x.com/ericries [ https://substack.com/redirect/67529d92-02d4-4415-9304-ad315003c3b7?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• LinkedIn: https://www.linkedin.com/in/eries [ https://substack.com/redirect/3b26ef33-aee3-4676-b67b-83bb72f09cf4?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Website: https://www.incorruptible.co [ https://substack.com/redirect/f1797c87-dd05-4ced-b144-7be9031283e7?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Newsletter: https://news.theleanstartup.com/ [ https://substack.com/redirect/550fa2d3-d5f8-4094-9f5d-4e3937ad8381?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Podcast: https://ericriesshow.com [ https://substack.com/redirect/e982b4b2-de85-45ca-a84b-79c2a39620a6?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• YouTube: https://www.youtube.com/@theericriesshow [ https://substack.com/redirect/02d52729-4f20-44a7-bd68-7145262fa359?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Referenced:
• Reflections on a movement | Eric Ries (creator of the Lean Startup methodology): https://www.lennysnewsletter.com/p/reflections-on-a-movement-eric-ries [ https://substack.com/redirect/5e241ef6-fd58-444e-995a-1daccaeaf845?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• How Anthropic’s product team moves faster than anyone else | Cat Wu (Head of Product, Claude Code): https://www.lennysnewsletter.com/p/how-anthropics-product-team-moves [ https://substack.com/redirect/9c4b616d-98ac-4caa-b4fd-d7521ba607b1?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Quibi: https://en.wikipedia.org/wiki/Quibi [ https://substack.com/redirect/1043f16f-98e2-4cc3-a84f-d16eca394e59?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Vital Farms: https://vitalfarms.com [ https://substack.com/redirect/99689dac-10a6-48c0-9066-6839c2f63049?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• BlackRock: https://www.blackrock.com [ https://substack.com/redirect/e0441aef-7924-4a5e-a371-3ad11e8d0984?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Costco: https://www.costco.com [ https://substack.com/redirect/f133a8fc-45ad-4a08-b792-870aa7f4e4d4?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Cloudflare: https://www.cloudflare.com [ https://substack.com/redirect/924413ec-3f31-4d8c-8399-e7dea5c18f5b?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• “The best time to plant a tree” quote: https://quoteinvestigator.com/2021/12/29/plant-tree [ https://substack.com/redirect/47290202-f2da-485c-a879-155fc6513dd6?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Whole Foods: http://wholefoodsmarket.com [ https://substack.com/redirect/f0055efc-fd8f-490a-b96b-f80d121a05df?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Marie Krogh: https://en.wikipedia.org/wiki/Marie_Krogh [ https://substack.com/redirect/e71d7eec-6851-4218-aa60-8b951ddfe6bf?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• August Krogh: https://en.wikipedia.org/wiki/August_Krogh [ https://substack.com/redirect/304dbed5-1cb9-48c8-8c3b-e9fcf31c713d?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Martin Shkreli: https://en.wikipedia.org/wiki/Martin_Shkreli [ https://substack.com/redirect/6b902926-8cf9-4d5f-8ec5-9c2493ac0fbc?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Novo Nordisk: https://www.novonordisk.com [ https://substack.com/redirect/ea5aa45e-2413-4ca8-b185-717c1b37e4c7?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Zeiss: https://www.zeiss.com [ https://substack.com/redirect/c0a60ecf-98b6-4077-8dea-55ad4cabc5d4?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Philip Morris: https://www.philipmorrisusa.com [ https://substack.com/redirect/c6d8ffc1-8f90-4358-8aa6-70ffb83a1a36?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Vectura: https://en.wikipedia.org/wiki/Vectura [ https://substack.com/redirect/a2ee37f5-d180-4be0-80e7-d69ecdc25781?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Matthew Prince on X: https://x.com/eastdakota [ https://substack.com/redirect/af17adb6-92ca-4beb-9da7-a15147976d1e?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• “AI Will Break the Internet”—Cloudflare CEO’s Big Prediction: https://www.ericriesshow.com/matthew-prince-ai [ https://substack.com/redirect/a9f3020f-777f-441a-a536-701c414cd48a?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Andrew Mason on LinkedIn: https://www.linkedin.com/in/andrewmason [ https://substack.com/redirect/037d9da5-54bb-4a17-896b-c16d6a0c7b71?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Groupon: https://www.groupon.com [ https://substack.com/redirect/ebae19c4-dc1a-4678-9d9e-56f9632faee0?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Steve Jobs: https://en.wikipedia.org/wiki/Steve_Jobs [ https://substack.com/redirect/aec70a38-6966-4e7d-866c-9715ce8b516e?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Yvon Chouinard: https://en.wikipedia.org/wiki/Yvon_Chouinard [ https://substack.com/redirect/e1aeebdf-d958-448a-b9f6-587ad1cd7f34?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Patagonia: https://www.patagonia.com [ https://substack.com/redirect/ecbff9dd-a9a8-47be-b8f3-4c335565b97e?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Unilever: https://en.wikipedia.org/wiki/Unilever [ https://substack.com/redirect/d652332c-5189-4ecc-ad7a-7fe00decfc50?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Johnson & Johnson: https://www.jnj.com [ https://substack.com/redirect/e6437f03-c1d9-435b-9a44-ccb186f1d10b?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Peter Drucker: https://en.wikipedia.org/wiki/Peter_Drucker [ https://substack.com/redirect/c751507a-c63d-4540-8f3f-bbafa0a4bbbd?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• How the Former U.S. CTO Built a $3B Healthcare Company Powered by Love | Todd Park: https://www.ericriesshow.com/how-the-former-us-cto-built-a-3b-healthcare-company-powered-by-love-todd-park [ https://substack.com/redirect/7671462b-6866-458b-94c7-60e30d6b343f?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Devoted Health: https://www.devoted.com [ https://substack.com/redirect/cdeeeaee-45ad-416a-bda1-f676d17e92ec?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Don’t be evil: https://en.wikipedia.org/wiki/Don%27t_be_evil [ https://substack.com/redirect/67c0fb20-4fac-4332-b9a7-89c51a1b7d7c?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Silicon Valley on HBO Max: https://www.hbomax.com/shows/silicon-valley/b4583939-e39f-4b5c-822d-5b6cc186172d [ https://substack.com/redirect/474cb49f-1acf-416e-a1a2-855c53e84081?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Adam Smith: https://en.wikipedia.org/wiki/Adam_Smith [ https://substack.com/redirect/c15c58a4-0aaa-41a5-bb60-bc8e1990d68b?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Understanding public benefit corporations: Profit with a purpose: https://www.britannica.com/money/what-is-a-public-benefit-corporation [ https://substack.com/redirect/418f23d2-edb7-4f7c-9a4f-1a2dfd5bab85?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• B Corp: https://www.bcorporation.net [ https://substack.com/redirect/0895232e-6d5e-431f-ac83-0546172072f5?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Anthropic: https://www.anthropic.com [ https://substack.com/redirect/4e2ee38f-2437-43a4-ad32-b62d8539b01d?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Clayton Christensen: https://en.wikipedia.org/wiki/Clayton_Christensen [ https://substack.com/redirect/ac158615-47df-45db-b216-ddbc0459c889?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Howard Schultz on LinkedIn: https://www.linkedin.com/in/howardschultz [ https://substack.com/redirect/a1d550e7-6688-4a5a-bf76-fc6532b5c918?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• HEB: https://www.heb.com [ https://substack.com/redirect/25dd64e6-388e-4768-98ab-29a50d119997?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Mary Parker Follett: https://en.wikipedia.org/wiki/Mary_Parker_Follett [ https://substack.com/redirect/f8a8c0a9-a91d-40ce-8877-6e1de99b88cc?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Elon Musk on X: https://x.com/elonmusk [ https://substack.com/redirect/505b8260-44a4-4665-bea6-c4d9b371e4d9?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Sam Altman on X: https://x.com/sama [ https://substack.com/redirect/2d817cce-228f-47a0-b67f-db347dcc10d7?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Dario Amodei on X: https://x.com/DarioAmodei [ https://substack.com/redirect/d7b94e9f-8d32-488e-8675-4f0f8cd283e0?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Daniela Amodei on LinkedIn: https://www.linkedin.com/in/daniela-amodei-790bb22a [ https://substack.com/redirect/40aea510-0946-43b5-a4dd-f0435aa1bd59?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Kobayashi Maru: https://en.wikipedia.org/wiki/Kobayashi_Maru [ https://substack.com/redirect/e388981c-0e0d-4716-be75-08fe7192c81a?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Mark Zuckerberg: https://en.wikipedia.org/wiki/Mark_Zuckerberg [ https://substack.com/redirect/50bc1fc4-a03b-4521-b9fe-52b5ae8aaa0a?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Larry Page: https://en.wikipedia.org/wiki/Larry_Page [ https://substack.com/redirect/6f119ba1-b7e9-4e55-a66f-01fed3266046?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Sergey Brin: https://en.wikipedia.org/wiki/Sergey_Brin [ https://substack.com/redirect/0a83d68d-46e5-4b97-8cdc-98f16ec07e36?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Rome Conference on AI, Ethics, and Governance: https://romeai.wsgrevents.com [ https://substack.com/redirect/171505bb-92a1-4d3a-9139-bedd49fc0ec2?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• OpenAI: https://openai.com [ https://substack.com/redirect/b3909628-bcd7-4884-91a3-04a5c7cb09ee?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Cohere: https://www.coherehealth.com [ https://substack.com/redirect/d594d03f-80a2-49aa-8fd9-e2991f1e0472?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Palantir: https://www.palantir.com [ https://substack.com/redirect/814243aa-8d70-4a05-b896-ec2567547727?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• John Lewis & Partners: https://www.johnlewis.com/ [ https://substack.com/redirect/2a54edc9-7ed4-49c3-9e88-0ab2b6bc840b?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Mondragon: https://mondragon-corporation.com [ https://substack.com/redirect/d99655c6-7db7-4b97-b038-6e233d1ff539?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Alibaba: https://www.alibaba.com [ https://substack.com/redirect/662b58bc-7e42-4cd3-a5d2-45485279646b?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• What is Evergreen?: https://www.tugboatinstitute.com/what-is-evergreen [ https://substack.com/redirect/5b24b82d-db5a-4bc7-a18c-06d60a69f395?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Berkshire Hathaway: https://www.berkshirehathaway.com [ https://substack.com/redirect/a6f33741-37cb-4d49-a79d-35d08b028a24?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Conway’s law: https://en.wikipedia.org/wiki/Conway%27s_law [ https://substack.com/redirect/bd2d3f74-d5dc-40cc-9e53-dbdccff82d9e?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Ants vs. humans: Solving the piano-mover puzzle: https://arstechnica.com/science/2025/01/ants-vs-humans-solving-the-piano-mover-puzzle [ https://substack.com/redirect/d7527728-11f2-40fa-b876-8499b056d451?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Frederick Winslow Taylor: https://en.wikipedia.org/wiki/Frederick_Winslow_Taylor [ https://substack.com/redirect/0abcdfa2-4d13-4266-bf0c-1844cd89391a?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• The Principles of Scientific Management (1911): https://en.wikipedia.org/wiki/The_Principles_of_Scientific_Management [ https://substack.com/redirect/01efe466-f920-4cad-8708-8228dd6a70f0?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Rowntree’s: https://en.wikipedia.org/wiki/Rowntree%27s [ https://substack.com/redirect/f1796696-f43f-41e0-a82f-8545be9767eb?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Recommended books:
• The Lean Startup: How Today’s Entrepreneurs Use Continuous Innovation to Create Radically Successful Businesses: https://www.amazon.com/Lean-Startup-Entrepreneurs-Continuous-Innovation/dp/0307887898 [ https://substack.com/redirect/e7e6c5c8-6b7e-42f5-aff9-879c9cccb6a8?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Incorruptible: Why Good Companies Go Bad... and How Great Companies Stay Great: https://www.amazon.com/Incorruptible-Good-Companies-Great-Stay/dp/B0FWZZBPZB [ https://substack.com/redirect/a86c6f4a-65b4-4ed9-9a01-01c63ee5def0?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Production and marketing by https://penname.co/ [ https://substack.com/redirect/35b97366-bc9a-432d-ab0e-a8997cdfc00b?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com [ mailto:podcast@lennyrachitsky.com ].
Lenny may be an investor in the companies discussed.
My biggest takeaways from this conversation:...
Unsubscribe https://substack.com/redirect/2/eyJlIjoiaHR0cHM6Ly93d3cubGVubnlzbmV3c2xldHRlci5jb20vYWN0aW9uL2Rpc2FibGVfZW1haWw_dG9rZW49ZXlKMWMyVnlYMmxrSWpvME1qWTFNVFV3TkRBc0luQnZjM1JmYVdRaU9qRTVOalEyT0RFek55d2lhV0YwSWpveE56YzROREUxTkRjd0xDSmxlSEFpT2pFNE1EazVOVEUwTnpBc0ltbHpjeUk2SW5CMVlpMHhNRGcwTlNJc0luTjFZaUk2SW1ScGMyRmliR1ZmWlcxaGFXd2lmUS4yQklaTVRsZkxBaHhSSXFqYWhJTjduS21KTXh6MXNtRXNRR0dMd0dIMXJzIiwicCI6MTk2NDY4MTM3LCJzIjoxMDg0NSwiZiI6dHJ1ZSwidSI6NDI2NTE1MDQwLCJpYXQiOjE3Nzg0MTU0NzAsImV4cCI6MjA5Mzk5MTQ3MCwiaXNzIjoicHViLTAiLCJzdWIiOiJsaW5rLXJlZGlyZWN0In0.DCInhDLZb450-f82PMKGuG_xvLzoGZg_J_WpxxL-xLI?
View Email
How to build a company that withstands any era | Eric Ries, Lean Startup author
lenny@substack.com5/10/2026
SubstackView this post on the web at https://www.lennysnewsletter.com/p/why-saas-freemium-playbooks-dont
👋 Hey there, I’m Lenny. Each week, I answer reader questions about building product, driving growth, and accelerating your career. For more: Lenny’s Podcast [ https://substack.com/redirect/3bf8d4c3-f6ab-4dcf-b6ed-33247fb76704?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] | Lennybot [ https://substack.com/redirect/e6655aa2-5b7a-41ee-87b9-a3328abbf72b?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] | How I AI [ https://substack.com/redirect/c01160dc-e51c-45bb-ba07-447307272f5b?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] | My favorite AI/PM courses [ https://substack.com/redirect/7d690386-594e-441b-a28a-c9c29a230299?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], public speaking course [ https://substack.com/redirect/501cb100-7e76-477d-98b3-1787a3e3b3b0?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], and interview prep copilot [ https://substack.com/redirect/2fa3f183-b561-41cb-8784-e4bcf6782903?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
P.S. Get a full free year of Google AI, Cursor, Lovable, Notion, Manus, Replit, Gamma, n8n, Canva, ElevenLabs, Factory, Wispr Flow, Fin, Supabase, Bolt, Linear, PostHog, Framer, Railway, Granola, Warp, Gumloop, Magic Patterns, Mobbin, Stripe Atlas, and ChatPRD, by becoming an Insider subscriber [ https://substack.com/redirect/4f589202-cce8-47fd-bddb-6609023fb69e?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]. Yes, this is for real [ https://substack.com/redirect/b7178115-ab9b-4847-bc29-0e24c26ae3ba?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ].
Today’s guest author, Vikas Kansal [ https://substack.com/redirect/311d5abd-b793-4352-a926-0baf958b9585?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], leads product for Google AI [ https://substack.com/redirect/0141ae1b-b7ac-4acc-9e20-d3e49f0ab594?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], arguably the most successful consumer subscription bundle in history, with Gemini 3.1, Nano Banana, NotebookLM, Veo3, and terabytes (!) of cloud storage. Vikas has been on the front lines of figuring out how to successfully monetize AI products, balancing compute costs with sustainable growth, and in today’s in-depth guest post, he shares all the lessons he and his team have learned about paywalling AI.
Let’s get into it.
You’ve just launched an incredible AI product. Growth is exploding, and users are completely hooked on the “magic” of your free tier. Then your bills arrive. In traditional SaaS, serving an extra free user costs essentially zero. In AI, every time a free user hits “Enter,” your GPUs fire, and your cash burns. AI products need to figure out monetization quickly, or compute costs will bankrupt your company.
Most product teams still reach for the traditional SaaS freemium playbook when designing their AI freemium strategy: give away the basics, and gate the best features. But as growth expert (and four-time Lenny’s Podcast guest) Elena Verna [ https://substack.com/redirect/24f7ed78-56fa-4429-9856-2ef42f2310dc?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] rightly points out, when building an AI product, you have to give away a massive amount of “magic” for users to get to the aha moment. They need to actually experience the model writing a perfect email or generating that perfect image before deciding to use a product even a second time. In today’s increasingly noisy market, the time to value (TTV) must be instantaneous if you hope to keep people’s attention.
But this creates a paradox: what happens when that free magical experience becomes so good (and expensive in compute) that it cannibalizes your premium tier?
While launching Google’s AI subscriptions [ https://substack.com/redirect/91d91f6a-99d3-4f55-bebd-d0dfb785bea7?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], we slammed right into this wall. The free tier was so good that for most tasks, it was outperforming humans. For free! It could write flawless Python, draft perfect marketing copy, and summarize long email threads instantly. We realized we were competing against ourselves, while also trying to create a sustainable business as demand for AI compute exponentially increases over time. Users rightly asked themselves, “Why should I pay $20 a month when the free version is already smarter than I am?”
The traditional SaaS playbook would suggest that we should’ve paygated some of our best features, like the viral [ https://substack.com/redirect/e935682d-e432-49b7-b696-a3030c70541e?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] NotebookLM podcast generator, Nano Banana images, or Gemini Deep Research. In the past, Slack successfully gated message history and Figma gated team libraries. But if we had paygated the ability to talk it out live with Gemini or Deep Research, users would never have experienced the magic needed to build a daily habit and worked up a desire to try the tools again. Plus, this may not have actually addressed the biggest sources of compute costs. The reality of AI products forced us to completely rebuild the anatomy of a paywall for AI subscriptions. Here is the framework we developed.
The anatomy of a modern AI paywall
The modern AI paywall should be constructed with both sides of the equation in mind: what users expect and what actually costs the company money in compute. This means moving beyond a traditional SaaS freemium model to multiple dynamic, usage-based, and outcome-driven tiers. If you are building an AI paywall, shift your upgrade triggers to these three pillars that align customer utility with costs to the company:
Pillar 1: Gate usage intensity
When we first added a paywall to Google’s AI features, our instinct was the traditional SaaS “premium” play: a single $20 Gemini Advanced tier, where users pay to access the smartest model. But we quickly hit two problems. First, as I mentioned above, the free tier was already so capable that many users felt it was already “smarter than them.” So they saw no reason to upgrade. But the second was more surprising: the power users who did upgrade were consuming such immense amounts of compute that the unit economics for the company were terrifying. We realized the real value proposition wasn’t just the quality of the model/answer, but the volume of work a user could pump through the system. And we’d have to price that access accordingly if the business model was going to work.
So we redesigned our offering into Plus, Pro, and Ultra tiers. Each bucket maps to a specific level of usage intensity, offering higher usage and larger context windows (up to 1 million tokens) as you move up. This provides users with predictable, prepaid pricing tiers and avoids the pay-per-use AWS-style bill shock that consumers hate. You get a taste of most features in every tier, and the Pro tier may be sufficient for a casual experimenter, while power users would opt for the Ultra tier. This approach aligned our unit economics and subscriber distribution to create a financially sustainable business model. We found that gating usage intensity was a more powerful monetization lever than gating model intelligence.
As another example, Midjourney [ https://substack.com/redirect/7741ba55-ad67-47b4-a2d2-f79dbd476f86?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] does this well. They use a “Fast Mode” vs. “Relax Mode” system. Fast Mode provides instant GPU access for quick results using limited monthly hours—which are priced accordingly. Once Fast Hours are exhausted, users on Standard plans or higher can switch to unlimited Relax Mode, which operates in a queue based on demand. Users are paying for priority access to their GPUs to generate more, faster images and not necessarily for better images. And the company can keep their unit economics tight.
Pillar 2: Gate outcomes
While Pillar 1 monetizes raw compute and volume, Pillar 2 monetizes productivity. The free tier may give a user the right answer, but it requires manual effort—copying, pasting, prompting, and formatting. To get users to upgrade, you must put a paywall in front of features that collapse multi-step tasks into a single click. “Pro” users are highly sensitive to friction, and they will justify the subscription cost simply based on the hours of work it eliminates from their life.
Our original value proposition for Gemini Advanced was built entirely around providing the “best and fastest answer” a frontier model could produce. Since then, LLMs made a major transition from passive text generators to autonomous AI agents that can reason, plan, use tools, and retain memory to complete complex tasks. We embraced this shift by making Chrome auto browse [ https://substack.com/redirect/a809210c-426c-4706-aa2b-6b0956ca8c7c?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] exclusively for our higher tiers. Chrome’s auto browse (powered by Gemini) is an AI agent feature that autonomously navigates websites, fills out forms, compares products, adds items to carts, and manages tasks like booking appointments within the browser. We framed the paywall around the employee labor saved, by letting the agent navigate the web and execute actions on behalf of the user to complete actual work. We stopped selling “answers” and started selling “hours.”
Intercom’s Fin AI agent [ https://substack.com/redirect/d233fce3-f093-4ade-8324-8309f6a15fca?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] is the gold standard in outcome-based AI pricing. It charges $0.99 per resolution. It’s free to let the AI try to answer, but you only pay when the user confirms their problem was actually solved. Sierra [ https://substack.com/redirect/ce8c4f4b-a618-415f-ab0a-4b09c270fd46?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] also does this well.
Pillar 3: Gate the heaviest compute modalities
When we were brainstorming the go-to-market for Genie 3—our real-time interactive “world model”—we knew the compute costs would be staggering. During internal dogfooding, we joked that the TPUs were melting on every prompt. We realized that offering this to every free user wasn’t just a bad business move but was physically impossible. There simply weren’t enough TPUs to serve this model at the 100K+ QPS required for hundreds of millions of DAUs. However, we also found that consumers intrinsically understand that these heavy modalities are a premium service. They don’t expect a cinematic, photorealistic 3D world to be free in the same way they expect a 500-word email to be.
So we made Genie 3 available exclusively to our highest-tier members. By elevating this frontier world model into a premium tier, we turned a massive compute liability into a powerful incentive for users to move to the top of our pricing ladder. This also enabled us to showcase the state-of-the-art model without running into capacity constraints.
My advice is to use your most expensive, compute-heavy modalities as the ultimate upgrade trigger for your highest subscription tier. Make text and basic image generation universally accessible to drive top-of-funnel growth, but set a hard paywall the moment a user wants to render a cinematic video, run a real-time simulation, or enter a persistent 3D environment.
Craft your monetization ecosystem
Well-crafted and value-aligned tiers can capture the user’s experimental budget, but they won’t keep it. AI subscriptions have relatively higher churn compared with traditional SaaS simply because the core usage habits are still being formed. To access that lifetime user value, you have to design an ecosystem surrounding the tiers to contain and expand your customer base. Below is how you optimize conversion, retention, and cost to serve to ensure that you’re building an ecosystem that lasts.
Nail your conversion catalysts
Deciding what value to put in which tier is only half the battle. You also need to master when and how to prompt the upsell that actually drives revenue. To push a highly engaged free user over the tipping point, you need specific conversion catalysts—behavioral triggers, contextual UX nudges, and strategic packaging that transform a frustrating roadblock into a frictionless, no-brainer upgrade. Showing the upgrade prompt is more an art than a science. Driving meaningful conversions ultimately comes down to surfacing the right contextual nudge to the right user at the exact moment of high intent. With Google AI subscriptions, we’ve found a few approaches that really work:...
Unsubscribe https://substack.com/redirect/2/eyJlIjoiaHR0cHM6Ly93d3cubGVubnlzbmV3c2xldHRlci5jb20vYWN0aW9uL2Rpc2FibGVfZW1haWw_dG9rZW49ZXlKMWMyVnlYMmxrSWpvME1qWTFNVFV3TkRBc0luQnZjM1JmYVdRaU9qRTVOVFkzTWpBeU5Td2lhV0YwSWpveE56YzNPVGczTURjM0xDSmxlSEFpT2pFNE1EazFNak13Tnpjc0ltbHpjeUk2SW5CMVlpMHhNRGcwTlNJc0luTjFZaUk2SW1ScGMyRmliR1ZmWlcxaGFXd2lmUS5wVWE2bWpRTHJGYlZpbkd2SUhLZTVEZkc0aFNGODhUaVhmTmdaenl0NUkwIiwicCI6MTk1NjcyMDI1LCJzIjoxMDg0NSwiZiI6dHJ1ZSwidSI6NDI2NTE1MDQwLCJpYXQiOjE3Nzc5ODcwNzcsImV4cCI6MjA5MzU2MzA3NywiaXNzIjoicHViLTAiLCJzdWIiOiJsaW5rLXJlZGlyZWN0In0.LY3_bcmRYcHKuApQvpdQSVJohL7UAeNZGGoPsG8QgMg?
View Email
Why SaaS freemium playbooks don’t work in AI, and what to do instead
lenny@substack.com5/5/2026
SubstackView this post on the web at https://www.lennysnewsletter.com/p/why-cultivating-agency-matters-more
Max Schoening is head of product at Notion, where he’s been especially effective at getting designers and PMs to ship code, prototype in the terminal, and launch extremely successful AI products. He was previously a PM at Google, ran design at Heroku, was VP of Design (and a part-time engineer) at GitHub, and is a two-time founder. He’s one of the most AI-forward product leaders out there and one of the deepest thinkers on how AI changes how we build and use software.
Listen on YouTube [ https://substack.com/redirect/3b1e9a2d-46ba-4093-9df3-7732a548edd5?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], Spotify [ https://substack.com/redirect/ece67822-06ec-4aaf-9340-0ffe1fab9c3a?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], and Apple Podcasts [ https://substack.com/redirect/a13a7c00-cf1f-4bd0-9671-63a07adcb95d?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
We discuss:
What’s most worked in getting designers and PMs to embrace AI
Why agency—not skills—is the thing that separates people who thrive from those who fall behind
How the first 10% of every project is now “free,” and what that means for product development
Max’s “tiny core” theory of great products: iPhone multitouch, the GitHub pull request, Notion blocks, Dropbox’s menu bar icon
Why the SaaSpocalypse is overstated
Why the amount of software has exploded but the quality hasn’t, and why that gap creates opportunity
Brought to you by:
WorkOS [ https://substack.com/redirect/3ed7f81a-7e1a-4724-9003-7b414b47b822?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]—Make your app Enterprise Ready, with SSO, SCIM, RBAC, and more
Vanta [ https://substack.com/redirect/f949bd56-b458-4a43-9199-1d38b3d46f5f?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]—Automate compliance, manage risk, and accelerate trust with AI
Where to find Max Schoening:
• X: https://x.com/mschoening [ https://substack.com/redirect/33ae38c6-ab9b-4a1d-b8a1-00669be5bd13?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• LinkedIn: https://www.linkedin.com/in/max-schoening [ https://substack.com/redirect/3952e4ca-6395-4e4d-a07e-3a1e4a6cb188?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Website: https://max.dev [ https://substack.com/redirect/8dc88780-2fe8-430f-8781-5e7259d31b28?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Referenced:
• Esther 4:14: https://www.biblegateway.com/passage/?search=Esther%204%3A14&version=NIV [ https://substack.com/redirect/3c38ecaf-7ec4-4eb5-a186-29f6be179c55?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Notion: https://www.notion.com [ https://substack.com/redirect/2e6f2714-039b-45cb-9ff8-b41289a150b3?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Figma: https://www.figma.com [ https://substack.com/redirect/6c7c3109-4c0a-401b-8d99-3abe36611b65?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Bret Victor—Stop Drawing Dead Fish: https://www.youtube.com/watch?v=ZfytHvgHybA [ https://substack.com/redirect/3c05a952-fb1d-46ca-a5e9-f61ecd286936?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• GitHub: https://github.com [ https://substack.com/redirect/03069c96-8505-4799-920f-4d7756db50c1?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Notion’s Brian Lovin on building a shared prototype playground, using Claude Code to transform Figma designs into working code, and why AI is changing how designers work: https://www.lennysnewsletter.com/p/i-havent-written-a-single-line-of [ https://substack.com/redirect/13f18837-d031-4c2d-a88b-3ff616f91a56?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Eric Liu on LinkedIn: https://www.linkedin.com/in/erictliu [ https://substack.com/redirect/8041c55e-b864-4861-aad8-2cbe2d8ed3d3?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Steve Jobs’s quote: https://quotefancy.com/quote/911503/Steve-Jobs-Everything-around-you-that-you-call-life-was-made-up-by-people-that-were-no [ https://substack.com/redirect/e524e75e-f0aa-4b22-b26d-f0b538fc9a8d?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Brian Chesky’s new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach [ https://substack.com/redirect/a6c26836-d8c7-4c0f-82c9-b03165a60639?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• The Dieter Rams video pinned to Max’s X profile: https://x.com/mschoening/status/1725199919739519299 [ https://substack.com/redirect/885b3bf9-0d30-4d50-a1ee-881198b6c949?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Frank Gehry: https://en.wikipedia.org/wiki/Frank_Gehry [ https://substack.com/redirect/18260d47-d46c-46c2-b168-ffd25255a587?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• He saved OpenAI, invented the “Like” button, and built Google Maps: Bret Taylor on the future of careers, coding, agents, and more: https://www.lennysnewsletter.com/p/he-saved-openai-bret-taylor [ https://substack.com/redirect/e5bea2b2-c739-49f0-9ee0-dc8a5a0ea287?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Joanna Stern’s post on X: https://x.com/JoannaStern/status/2023529964185022898 [ https://substack.com/redirect/9501be00-25d0-4eec-a624-8455502f0eef?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• How Anthropic’s product team moves faster than anyone else | Cat Wu (Head of Product, Claude Code): https://www.lennysnewsletter.com/p/how-anthropics-product-team-moves [ https://substack.com/redirect/3c7f401a-342a-4b2a-b402-6072c1d68b22?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• This is the flowchart of how Slack decides to send a notification: https://blog.bytebytego.com/p/flowchart-of-how-slack-decides-to [ https://substack.com/redirect/230853b5-4234-4978-b6e1-00eeaac007b2?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Tyler Cowen’s blog: https://marginalrevolution.com [ https://substack.com/redirect/f9a3e316-14b3-4ca7-9051-b9f3a81d3c2e?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Simon Last on X: https://x.com/simonlast [ https://substack.com/redirect/3a3324ba-9bb0-41af-b278-b248bd29bdf7?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Jevons paradox: https://en.wikipedia.org/wiki/Jevons_paradox [ https://substack.com/redirect/236abd97-17af-481d-8467-06e1d245504d?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Why Software Is Eating the World: https://a16z.com/why-software-is-eating-the-world [ https://substack.com/redirect/037f8680-f347-4b29-9879-0b381a33a0b3?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Why humans are AI’s biggest bottleneck (and what’s coming in 2026) | Alexander Embiricos (OpenAI Codex Product Lead): https://www.lennysnewsletter.com/p/why-humans-are-ais-biggest-bottleneck [ https://substack.com/redirect/52a16605-3a61-4e35-a43f-9e2b2518e7b7?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Heroku: https://www.heroku.com [ https://substack.com/redirect/0ba2cdf6-fef7-4483-953f-8cf6d5d93427?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Kubernetes: https://kubernetes.io [ https://substack.com/redirect/b05982a7-e8aa-4165-964c-f30cc2df1316?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Kathy Sierra: Badass—Making Users Awesome, at Mind the Product San Francisco: https://www.youtube.com/watch?v=LNnv2GrlnZw [ https://substack.com/redirect/b3f82ab1-2851-4557-bf4a-11841b847373?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Ivan Zhao on LinkedIn: https://www.linkedin.com/in/ivanhzhao [ https://substack.com/redirect/1405922b-b092-4441-9f7f-f7699f1e366a?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Dropbox: https://www.dropbox.com [ https://substack.com/redirect/864b0736-3f1f-41a8-8b6a-fa1ace61ee36?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Dario Amodei on X: https://x.com/DarioAmodei [ https://substack.com/redirect/ee395b2c-16b2-4b80-9247-0dc41c20d2f0?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Clayton Christensen: https://en.wikipedia.org/wiki/Clayton_Christensen [ https://substack.com/redirect/e93f849b-af9f-424e-ae62-a959198aa85c?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• The ultimate guide to JTBD | Bob Moesta (co-creator of the framework): https://www.lennysnewsletter.com/p/the-ultimate-guide-to-jtbd-bob-moesta [ https://substack.com/redirect/ea545971-1cdd-4162-8b68-3e4ad943903a?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Lee Sedol: https://en.wikipedia.org/wiki/Lee_Sedol [ https://substack.com/redirect/ccd52206-f0e4-4385-bbcf-dcfb9f3eb401?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• AlphaGo: https://deepmind.google/research/alphago [ https://substack.com/redirect/3fdd11c3-ceeb-40f2-8a44-d4584c67ebe8?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• TBPN: https://www.tbpn.com [ https://substack.com/redirect/2318989c-16d9-409e-a5b4-cae6856e9ae4?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Chris Rock: https://en.wikipedia.org/wiki/Chris_Rock [ https://substack.com/redirect/5fab3f9c-764a-4726-8e67-60f2defee5c2?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Stack Overflow: https://stackoverflow.com [ https://substack.com/redirect/17d5f18e-7384-4d05-b6cf-8a8f3f3af90d?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Project Hail Mary: https://www.imdb.com/title/tt12042730 [ https://substack.com/redirect/7eea6390-8a68-4cc0-91d1-e4846ab44cad?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• The Handmaid’s Tale: https://www.imdb.com/title/tt5834204 [ https://substack.com/redirect/5c6794a1-f02f-4b67-b04b-f0c5d75bfbdf?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Ghostty: https://ghostty.org [ https://substack.com/redirect/ba2cbfd8-7fa9-4259-86a4-772452078dae?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Mitchell Hashimoto on X: https://x.com/mitchellh [ https://substack.com/redirect/aeda28df-b058-4218-a09f-c55d0c7c9fef?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Moshi: https://getmoshi.app [ https://substack.com/redirect/58b669c7-f436-435e-ba43-18ceccae5123?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• YMDK Split Keyboard Corne V4.1 46 Keys Ergonomic Hotswappable 40% Layout 3D PLA RGB QMK Vial All Key Programmable Mini Independent Gaming Keyboard Kit: https://www.amazon.com/YMDK-Ergonomic-Hotswappable-Programmable-Independent/dp/B0DWSKP3ZT [ https://substack.com/redirect/5f2e2a11-36ba-4a47-9314-d0c27dfe6af0?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Civivi pocket knives: https://www.civivi.com/collections/folding-pocket-knives [ https://substack.com/redirect/03cd5f5d-c8d2-4793-bcb5-1937c8dc40d6?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Marcus Aurelius’s quote: https://www.goodreads.com/quotes/762780-the-whole-universe-is-change-and-life-itself-is-but [ https://substack.com/redirect/a553f71b-8b43-4fc4-b63c-af103cebbe86?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Recommended books:
• Code: The Hidden Language of Computer Hardware and Software: https://www.amazon.com/Code-Language-Computer-Hardware-Software/dp/0137909101 [ https://substack.com/redirect/7be8b9b9-078e-4c89-b385-5543efb98058?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Tools for Conviviality: https://www.amazon.com/Tools-Conviviality-Ivan-Illich/dp/1842300113 [ https://substack.com/redirect/09f9e470-b7ae-48df-afe3-1132e545053f?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Seeing Like a State: How Certain Schemes to Improve the Human Condition Have Failed: https://www.amazon.com/Seeing-Like-State-Condition-Paperbacks/dp/0300246757 [ https://substack.com/redirect/0e0006cb-9507-43a2-a447-484529859629?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Production and marketing by https://penname.co/ [ https://substack.com/redirect/11bda97f-8cc5-44f7-9a93-88b44df87ede?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com [ mailto:podcast@lennyrachitsky.com ].
Lenny may be an investor in the companies discussed.
My biggest takeaways from this conversation:...
Unsubscribe https://substack.com/redirect/2/eyJlIjoiaHR0cHM6Ly93d3cubGVubnlzbmV3c2xldHRlci5jb20vYWN0aW9uL2Rpc2FibGVfZW1haWw_dG9rZW49ZXlKMWMyVnlYMmxrSWpvME1qWTFNVFV3TkRBc0luQnZjM1JmYVdRaU9qRTVORFUyTmpZMk9Td2lhV0YwSWpveE56YzNPREV5TVRZd0xDSmxlSEFpT2pFNE1Ea3pORGd4TmpBc0ltbHpjeUk2SW5CMVlpMHhNRGcwTlNJc0luTjFZaUk2SW1ScGMyRmliR1ZmWlcxaGFXd2lmUS5YN2FIZmdEUWFMVW4tdENxN2MtLW4xejNKTXZ3a3dXaVdJV05ELVFHRzNzIiwicCI6MTk0NTY2NjY5LCJzIjoxMDg0NSwiZiI6dHJ1ZSwidSI6NDI2NTE1MDQwLCJpYXQiOjE3Nzc4MTIxNjAsImV4cCI6MjA5MzM4ODE2MCwiaXNzIjoicHViLTAiLCJzdWIiOiJsaW5rLXJlZGlyZWN0In0.L50x4Y7Qzv-n6xVRTTxljpTx3tCLMROq6B5OtDZT4FY?
View Email
Why cultivating agency matters more than cultivating skills in the AI era | Max Schoening (Head of Product, Notion)
lenny@substack.com5/3/2026
SubstackView this post on the web at https://www.lennysnewsletter.com/cp/195894129
Unsubscribe https://substack.com/redirect/2/eyJlIjoiaHR0cHM6Ly93d3cubGVubnlzbmV3c2xldHRlci5jb20vYWN0aW9uL2Rpc2FibGVfZW1haWw_dG9rZW49ZXlKMWMyVnlYMmxrSWpvME1qWTFNVFV3TkRBc0luQnZjM1JmYVdRaU9qRTVOVGc1TkRFeU9Td2lhV0YwSWpveE56YzNORGd5TnprMkxDSmxlSEFpT2pFNE1Ea3dNVGczT1RZc0ltbHpjeUk2SW5CMVlpMHhNRGcwTlNJc0luTjFZaUk2SW1ScGMyRmliR1ZmWlcxaGFXd2lmUS45UGc1UTRGZmFSQXZlWHZHWVdLa01kMXZERTdGQ19ORTd0d2E2N2d4VlRvIiwicCI6MTk1ODk0MTI5LCJzIjoxMDg0NSwiZiI6dHJ1ZSwidSI6NDI2NTE1MDQwLCJpYXQiOjE3Nzc0ODI3OTYsImV4cCI6MjA5MzA1ODc5NiwiaXNzIjoicHViLTAiLCJzdWIiOiJsaW5rLXJlZGlyZWN0In0.THPEgEkdO5b0VAjGTnVQal4CqPo12uAf-lCvI4Ie2M8?
View Email
The product skill you must now master: Reinvention
lenny@substack.com4/29/2026
SubstackView this post on the web at https://www.lennysnewsletter.com/p/your-couch-to-5k-for-ai
👋 Hey there, I’m Lenny. Each week, I answer reader questions about building product, driving growth, and accelerating your career. For more: Lenny’s Podcast [ https://substack.com/redirect/da44a77c-fabf-419e-8a40-246d6ee95a4e?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] | Lennybot [ https://substack.com/redirect/a9fc9f07-1ae4-4b98-8a6f-d1c95acc30f5?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] | How I AI [ https://substack.com/redirect/25cedb2d-13bb-4e31-b31e-d32c9e217e61?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] | My favorite AI/PM courses [ https://substack.com/redirect/3281508e-eb34-4556-8266-dda7131cceed?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], public speaking course [ https://substack.com/redirect/b46bfdeb-d4e7-4c9e-8cbf-8f02b0ae839e?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], and interview prep copilot [ https://substack.com/redirect/5bf6d24a-0fe6-4260-9c33-a74a5430f5eb?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
P.S. Get a full free year of Google AI, Cursor, Lovable, Notion, Manus, Replit, Gamma, n8n, Canva, ElevenLabs, Factory, Wispr Flow, Fin, Supabase, Bolt, Linear, PostHog, Framer, Railway, Granola, Warp, Gumloop, Magic Patterns, Mobbin, Stripe Atlas, and ChatPRD, by becoming an Insider subscriber [ https://substack.com/redirect/480e0bfe-503d-42b6-85c5-92ee53b063ae?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]. Yes, this is for real [ https://substack.com/redirect/061708dd-1daf-4af0-888e-fa59182256b5?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ].
I’m teaming up with AI native and my many-time collaborator Hilary Gridley [ https://substack.com/redirect/23b4df04-6c33-4fec-afea-74bee5a83253?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] on a project that will accelerate your AI learning more than anything you’ve tried. For free. Open this link in a new tab [ https://substack.com/redirect/0dbd393f-f010-444a-a321-ae64e7311148?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], and keep reading.
For more from Hilary, find her on LinkedIn [ https://substack.com/redirect/23b4df04-6c33-4fec-afea-74bee5a83253?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] and X [ https://substack.com/redirect/9d4137d6-d39d-4186-b6a5-ee7a6d728c1f?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], and check out her newsletter [ https://substack.com/redirect/2425e7dc-1641-4c57-b3c5-e33e5404df72?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] and her course, How to Become a Supermanager with AI [ https://substack.com/redirect/7f941193-b244-41b7-a8a5-6a96170239bc?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ].
“I keep meaning to really dig into AI, but I can’t seem to find the time. I’m just too busy.”
I hear this from executives, from managers, from ICs, from technical and non-technical people alike. From people with jobs, people looking for work, students, entrepreneurs, stay-at-home-moms. They’re all underwater and hungry for more leverage, but it’s not totally clear how to go from “asking it questions” to something that meaningfully gives them time back—especially when investing that initial effort takes time away from work they already know how to do.
This challenge is not new and not reserved for AI. I’ve spent much of my career working on products that consistently change people’s behavior to improve how they live and work (WHOOP, Dropbox, Big Health), which means I’ve had thousands of conversations with people who say they want to make a positive change in their life but struggle to actually do it.
When you dig into what is standing in their way, time is always the first thing they say. You hear it over and over: “I’m just too busy; I can’t find the time right now.” But even when they find time, they rarely end up making progress on the goal that’s been eluding them. As a result, I’ve learned to become very suspicious of the word “busy.” When people say they want to do something but are too busy, there is almost always something else standing in their way.
This is the root of procrastination. At its core, you are waiting for some external force to change—like your endless to-do list magically disappearing, or your calendar suddenly opening up—rather than making a change in your actions, which is hard.
So how do you get over procrastination? Tim Pychyl, a psychologist and procrastination expert, says, “Research and our lived experience show very clearly that once we get started, we’re typically able to keep going. Getting started is everything.” So the answer is very simple: Break down the task into the smallest possible first step you could take, and then take that step. Then the next one, then the next one.
I’ve seen this philosophy transform all aspects of people’s lives. We took it to heart at WHOOP when we launched Healthspan, which tracks nine key metrics to calculate your physiological “WHOOP Age” and “Pace of Aging.” When people saw their WHOOP Age, they often wanted to make big changes across lots of behaviors to improve it. But we found that the best way to help them make progress was the simplest: offer a new bedtime to aim for tonight. Likewise, a digital depression treatment I developed at Big Health focused on helping patients take one mood-lifting action every day. The most common failure pattern was taking on too big of an action, like trying to plan a whole dinner party, and then getting overwhelmed and making no progress on it. So the key to keeping people engaged (and to driving clinically validated improvements in depression symptoms) was to help them break it down and commit to just the first step.
This philosophy has influenced the products I build, how I manage my team, and, most recently, how I help people transform their work with AI. Taking one single, simple step each day is the key to building your AI expertise.
What you need is a Couch-to-5K for AI: a progressive daily practice that builds the habit, using the same behavior-change principles that make fitness programs work. Small wins build confidence, confidence builds momentum, and momentum motivates you to keep going. It starts to feel like you’ve discovered a better way to make real progress instead of adding yet another thing to your to-do list.
In 2024, I created a very simple version of this called “30 Days of GPT,” which I shared in my last guest post on this newsletter [ https://substack.com/redirect/10d3204c-acab-42dd-bd93-8757c7809680?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]. It was extremely popular and was featured in outlets like Harvard Business Review.
Now I’ve updated the program for 2026 to get you from chatting with AI to actually building with it, no matter who you are or what kind of work you do, using Claude Code.
Get started with your Couch-to-5K for AI
Couch-to-5K for AI [ https://substack.com/redirect/0dbd393f-f010-444a-a321-ae64e7311148?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] is free, takes fewer than 10 minutes a day, and is designed to build your AI practice progressively. I took a very deliberate approach to each piece of the system: what you do each day, what order things go in, and how the skills build on each other. You can stop reading this post now and get started here [ https://substack.com/redirect/0dbd393f-f010-444a-a321-ae64e7311148?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ].
Seriously, you can skip the rest of this post if you want and just get learning [ https://substack.com/redirect/0dbd393f-f010-444a-a321-ae64e7311148?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ].
Or, if you’re not sure that this will be worth your time, here are the before-and-after pictures across different types of roles:
A months-long debate, resolved
New positioning, live in hours...
Unsubscribe https://substack.com/redirect/2/eyJlIjoiaHR0cHM6Ly93d3cubGVubnlzbmV3c2xldHRlci5jb20vYWN0aW9uL2Rpc2FibGVfZW1haWw_dG9rZW49ZXlKMWMyVnlYMmxrSWpvME1qWTFNVFV3TkRBc0luQnZjM1JmYVdRaU9qRTVOVFUxT1RFNU9Dd2lhV0YwSWpveE56YzNNemt4TURreExDSmxlSEFpT2pFNE1EZzVNamN3T1RFc0ltbHpjeUk2SW5CMVlpMHhNRGcwTlNJc0luTjFZaUk2SW1ScGMyRmliR1ZmWlcxaGFXd2lmUS5EWXNtaEVob1NuNkZuOHhOcW96YU5nUzZOdV9pSzJXT1NvanJUWHJYVXc0IiwicCI6MTk1NTU5MTk4LCJzIjoxMDg0NSwiZiI6dHJ1ZSwidSI6NDI2NTE1MDQwLCJpYXQiOjE3NzczOTEwOTEsImV4cCI6MjA5Mjk2NzA5MSwiaXNzIjoicHViLTAiLCJzdWIiOiJsaW5rLXJlZGlyZWN0In0.i7HWb6IwTuqj_QJY_pcOk7cTEC8kEo1fGQXsnajoiQM?
View Email
Your Couch-to-5K for AI
lenny@substack.com4/28/2026
SubstackView this post on the web at https://www.lennysnewsletter.com/p/snapchat-ceo-why-distribution-is
Evan Spiegel, the co-founder and CEO of Snap, is one of the very few people in the world who has successfully built and scaled a lasting consumer social product. Snapchat has nearly 1 billion MAUs, and Evan and his team invented some of the most important consumer products and features, including Stories, AR glasses, swipe-based navigation, the camera as the primary UX, and a lot more.
Listen on YouTube [ https://substack.com/redirect/14689af9-ccb4-4181-a53c-5ca4acf2217b?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], Spotify [ https://substack.com/redirect/d8569481-6627-41b6-8402-661c4e9ce49e?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], and Apple Podcasts [ https://substack.com/redirect/e298c5ed-78a3-40c9-a83c-f6844e0700a2?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
In our in-depth conversation, we discuss:
Why distribution is now the biggest challenge for creating a consumer technology business
How Snap innovates at scale with a 9-to-12-person design team: no titles, no hierarchy, hundreds of ideas reviewed weekly with the CEO
Why a pure software business is no longer a moat, and what actually creates durable competitive advantages today
How AI is changing the way designers work and why they’re now shipping code
Why every major Snap feature was copied and how that forced the company to work differently
Evan’s prediction that humanity’s comfort with AI will be a bigger bottleneck than the technology itself
This year’s crucible moment for Snap
Brought to you by:
WorkOS [ https://substack.com/redirect/4fcf2d1a-cc05-4c0e-b956-9df813dd9f59?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]—Modern identity platform for B2B SaaS, free up to 1 million MAUs
Vanta [ https://substack.com/redirect/b48731ea-a135-4e48-9156-7984a9fda9ae?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]—Automate compliance, manage risk, and accelerate trust with AI
Where to find Evan Spiegel:
• X: https://x.com/evanspiegel [ https://substack.com/redirect/54e97a39-0ca2-4807-80f0-8c27f8909549?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Snapchat: https://www.snapchat.com/@evan [ https://substack.com/redirect/67caafb9-088e-4509-830c-3f1e4be14ca2?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• LinkedIn: https://www.linkedin.com/in/evan-spiegel [ https://substack.com/redirect/f039bed2-05f1-424a-8b9f-a8a3e0379806?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Website: https://www.spiegelfamilyfund.com [ https://substack.com/redirect/e4de9186-ad47-47cd-9936-2a30b4183436?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Referenced:
• Snapchat: https://www.snapchat.com [ https://substack.com/redirect/e109449d-74c4-45f8-a540-dfd39cc43a4c?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• TikTok: https://www.tiktok.com [ https://substack.com/redirect/1db6ed09-b043-4b27-8f82-235741c0d5cf?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Threads: https://www.threads.com [ https://substack.com/redirect/33dbe22c-9922-4c4d-941b-f3d286c658cc?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Snapchat+: https://www.snapchat.com/plus [ https://substack.com/redirect/0ba4141b-bea7-4f40-9c07-e15d7ff74f39?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Instagram Plus: https://help.instagram.com/26266751476298047 [ https://substack.com/redirect/7f17104a-3eb0-4f5e-9005-cfee5ec8ccb5?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Pixy: https://www.pixy.com [ https://substack.com/redirect/778649a4-79d9-4d0a-b802-ab686ea4a988?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Specs: https://newsroom.snap.com/introducing-specs-inc [ https://substack.com/redirect/d7c9b998-96fb-4180-852b-07d707d9b290?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Bobby Murphy: https://en.wikipedia.org/wiki/Bobby_Murphy [ https://substack.com/redirect/6472f295-e762-4fb9-9c46-2b49747ab120?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Hard truths about building in the AI era | Keith Rabois (Khosla Ventures): https://www.lennysnewsletter.com/p/hard-truths-about-building-in-the-ai-era [ https://substack.com/redirect/499f1d0e-91f8-492c-9ef4-9ac6752efaef?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Marc Andreessen: The real AI boom hasn’t even started yet: https://www.lennysnewsletter.com/p/marc-andreessen-the-real-ai-boom [ https://substack.com/redirect/1b7ff58f-0056-4d1d-aadc-e4b5226f344f?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• The design process is dead. Here’s what’s replacing it. | Jenny Wen (head of design at Claude): https://www.lennysnewsletter.com/p/the-design-process-is-dead [ https://substack.com/redirect/d1f5e542-71fd-4f58-853d-daa645aa0262?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Claude Cowork: https://www.anthropic.com/product/claude-cowork [ https://substack.com/redirect/a75ef406-8279-4d53-b0ab-c3fc3bffce9e?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Figma: https://www.figma.com [ https://substack.com/redirect/fd5b44e2-e083-4658-b7f6-1c43b8dd5ffd?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Bill Clinton on X: https://x.com/BillClinton [ https://substack.com/redirect/49971fa3-0377-413c-bdfd-737644c8ce32?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Superhuman’s secret to success: Ignoring most customer feedback, manually onboarding every new user, obsessing over every detail, and positioning around a single attribute: speed | Rahul Vohra (CEO): https://www.lennysnewsletter.com/p/superhumans-secret-to-success-rahul-vohra [ https://substack.com/redirect/e0ea2ec6-d555-4e7f-ac97-caa8f2a53710?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Bobcat tractors: https://www.bobcat.com/na/en/equipment/tractors [ https://substack.com/redirect/aa359c86-fba5-4a9e-89e8-9e8682c6d4b4?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Palmer Luckey’s blog: https://palmerluckey.com [ https://substack.com/redirect/b3b7bd16-0d73-413c-8c6c-be1d03169b00?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• ModRetro: https://modretro.com [ https://substack.com/redirect/f1fa681b-6731-4759-beb0-db24e1aca690?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Glean: https://www.glean.com [ https://substack.com/redirect/e8c36225-ad7c-492e-8925-6ee909136ad4?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Marty Supreme on Prime Video: https://www.primevideo.com/detail/Marty-Supreme/0GU3TFPDR9FE2C6L7AAWAA3QXD [ https://substack.com/redirect/b0d99d00-eb3d-4137-a459-aeaa7671367e?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Pokemon: https://www.pokemon.com [ https://substack.com/redirect/9a323405-2599-4f51-8342-0f91ac064323?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Puking rainbow lens: https://www.snapchat.com/lens/349f631e78cc4b3dbd8c9656a69dbdd0 [ https://substack.com/redirect/83fbbf58-b0df-4609-893a-3179c91df5af?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Face swap: https://www.snapchat.com/explore/face-swap [ https://substack.com/redirect/992025e3-bdc5-4bcc-9482-273248d22c00?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Recommended books:
• Loonshots: How to Nurture the Crazy Ideas That Win Wars, Cure Diseases, and Transform Industries: https://www.amazon.com/Loonshots-Nurture-Diseases-Transform-Industries/dp/1250185963 [ https://substack.com/redirect/3c8a15e7-0e36-41ba-a3a7-5b0a7743bbcd?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Thinking, Fast and Slow: https://www.amazon.com/Thinking-Fast-Slow-Daniel-Kahneman/dp/0374533555 [ https://substack.com/redirect/298f7662-bece-442f-9efe-20c44b5a9d6d?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Apple: The First 50 Years: https://www.amazon.com/Apple-First-Years-David-Pogue/dp/1982134593 [ https://substack.com/redirect/ff1e6787-f845-4e68-9ee0-5b259900c889?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• The End of the World Is Just the Beginning: Mapping the Collapse of Globalization―Irreverent Predictions from a Geopolitical Strategist: https://www.amazon.com/dp/B09CS8FRRD [ https://substack.com/redirect/69ba4492-8897-4a77-b366-469c2e2d3a80?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Production and marketing by https://penname.co/ [ https://substack.com/redirect/93087bed-fa3f-4b19-ad30-f0f7539e4f96?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com [ mailto:podcast@lennyrachitsky.com ].
Lenny may be an investor in the companies discussed.
My biggest takeaways from this conversation:...
Unsubscribe https://substack.com/redirect/2/eyJlIjoiaHR0cHM6Ly93d3cubGVubnlzbmV3c2xldHRlci5jb20vYWN0aW9uL2Rpc2FibGVfZW1haWw_dG9rZW49ZXlKMWMyVnlYMmxrSWpvME1qWTFNVFV3TkRBc0luQnZjM1JmYVdRaU9qRTVORFUwTkRBeE9Td2lhV0YwSWpveE56YzNNakEzTkRrNExDSmxlSEFpT2pFNE1EZzNORE0wT1Rnc0ltbHpjeUk2SW5CMVlpMHhNRGcwTlNJc0luTjFZaUk2SW1ScGMyRmliR1ZmWlcxaGFXd2lmUS5XNWRwalE1d1RzVXVhUzcweW1UNHNodXg0OV9IeW5ONHZVeW05cktLc0hFIiwicCI6MTk0NTQ0MDE5LCJzIjoxMDg0NSwiZiI6dHJ1ZSwidSI6NDI2NTE1MDQwLCJpYXQiOjE3NzcyMDc0OTgsImV4cCI6MjA5Mjc4MzQ5OCwiaXNzIjoicHViLTAiLCJzdWIiOiJsaW5rLXJlZGlyZWN0In0.5ktDZtgWg3NIv8S-1m-WTksoGL2LFJsevsbn9MtGlS0?
View Email
Snapchat CEO: Why distribution has become the most important moat | Evan Spiegel
lenny@substack.com4/26/2026
SubstackView this post on the web at https://www.lennysnewsletter.com/p/how-anthropics-product-team-moves
Cat Wu is Head of Product for Claude Code and Cowork at Anthropic, building one of the most important AI products of this generation. Before joining Anthropic, Cat spent years as an engineer and briefly worked in VC. Today, she’s interviewing hundreds of product managers who are trying to break into AI—and seeing firsthand what separates those who thrive from those who fall behind.
Listen on YouTube [ https://substack.com/redirect/137aaccb-3a7d-4a64-b109-6910b327fc97?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], Spotify [ https://substack.com/redirect/b940fecd-0a75-44ed-b58b-93782ac191d6?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], and Apple Podcasts [ https://substack.com/redirect/ae90b61f-caf9-4523-8383-4c516f16ea14?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
We discuss:
How Anthropic’s shipping cadence went from months to weeks to days
The emerging skills PMs need to develop right now
Why you need to build products that don’t yet fully work, so you’re ready when the next model closes the gap
Cat’s most underrated AI skill: asking the model to introspect on its own mistakes
Why Claude’s personality is core to its success
Why Anthropic’s mission alignment eliminates the friction that slows most large organizations
Why “just do things” is the most important principle for working at AI-native companies
Brought to you by:
WorkOS [ https://substack.com/redirect/978dfaf9-7552-4c24-b736-9262edc2020c?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]—Modern identity platform for B2B SaaS, free up to 1 million MAUs
Vanta [ https://substack.com/redirect/575d5256-6b8e-4fd8-8289-53e3e1d5f0d3?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]—Automate compliance, manage risk, and accelerate trust with AI
Where to find Cat Wu:
• X: https://x.com/_catwu [ https://substack.com/redirect/d678ada2-ad2a-43ae-b136-3c1d2a017af8?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• LinkedIn: linkedin.com/in/cat-wu [ https://substack.com/redirect/3c18a6ca-c00e-4f65-a271-d42474e1e969?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Newsletter: https://catwu.substack.com [ https://substack.com/redirect/92bee964-b975-4d41-b193-d423921c97ca?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Referenced:
• Head of Claude Code: What happens after coding is solved | Boris Cherny: https://www.lennysnewsletter.com/p/head-of-claude-code-what-happens [ https://substack.com/redirect/afe45474-f522-4d63-86b7-5ebdef7dc250?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Anthropic: https://www.anthropic.com [ https://substack.com/redirect/b418381b-e891-48b7-9332-681f12812efe?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Assessing Claude Mythos Preview’s cybersecurity capabilities: https://red.anthropic.com/2026/mythos-preview [ https://substack.com/redirect/f255917e-fc9e-4aa3-9de9-f8b01e93e5e8?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• OpenClaw: https://openclaw.ai [ https://substack.com/redirect/7bfd2f1d-bc35-4c5a-812c-94f9a703a0ec?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• OpenClaw: The complete guide to building, training, and living with your personal AI agent: https://www.lennysnewsletter.com/p/openclaw-the-complete-guide-to-building [ https://substack.com/redirect/ffc40b35-64d3-49ac-ab72-a3d7efeb31cb?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Listen: OpenClaw: A power user’s guide to the most powerful personal AI tool since ChatGPT: https://www.lennysnewsletter.com/p/listen-openclaw-a-power-users-guide [ https://substack.com/redirect/a0395c4f-36e0-4204-b606-9d6b7dff9692?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Dianne Na Penn on LinkedIn: https://www.linkedin.com/in/dianne-na-penn [ https://substack.com/redirect/a1484c0e-0bff-410c-87a0-dc3c1db23031?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Head of Growth (Anthropic): “Claude is growing itself at this point” | Amol Avasare: https://www.lennysnewsletter.com/p/anthropics-1b-to-19b-growth-run [ https://substack.com/redirect/a91a6907-e2e9-4e68-90b9-b2dc78a5d57d?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Anthropic co-founder on quitting OpenAI, AGI predictions, $100M talent wars, 20% unemployment, and the nightmare scenarios keeping him up at night | Ben Mann: https://www.lennysnewsletter.com/p/anthropic-co-founder-benjamin-mann [ https://substack.com/redirect/6d3bee1b-ca3a-474e-8cb6-9bf5fc15a323?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• GIF from Pirates of the Caribbean: https://tenor.com/view/pirate-of-pirate-of-the-carribean-jack-sparrow-pirati-dei-caraibi-sad-gif-14519798 [ https://substack.com/redirect/d726fd22-88e6-4323-8e87-36b427a56ef7?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• What’s New post with Claude powerup feature: https://code.claude.com/docs/en/whats-new/2026-w14 [ https://substack.com/redirect/4698f142-0a03-45b3-875f-83c0c6c801ac?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Claude Code: https://claude.com/product/claude-code [ https://substack.com/redirect/7cf8860e-138a-4fa6-af54-68d70fe87d20?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Terminal guide for new users: https://code.claude.com/docs/en/terminal-guide [ https://substack.com/redirect/9812e8fe-bed7-4669-9ef8-5c4366e56d48?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Claude Cowork: https://www.anthropic.com/product/claude-cowork [ https://substack.com/redirect/62e1a603-942c-4193-bec1-9a1f641b572d?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Anthropic’s developer conference: https://claude.com/code-with-claude/san-francisco [ https://substack.com/redirect/cf5835bd-7020-4928-9a99-74b9d68ac260?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Figma MCP: https://www.figma.com/mcp-catalog [ https://substack.com/redirect/175dffbc-d3a0-4952-a517-85e76d6ce57d?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Salesforce: https://www.salesforce.com [ https://substack.com/redirect/4cb7f336-f39e-4f8e-8402-24437e732617?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Gong: https://www.gong.io [ https://substack.com/redirect/fff8e0d8-1ace-4a20-8200-1ac791a3b777?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Slack founder: Mental models for building products people love ft. Stewart Butterfield: https://www.lennysnewsletter.com/p/slack-founder-stewart-butterfield [ https://substack.com/redirect/fe48bb35-b117-400a-9219-9231fe196782?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Why AI evals are the hottest new skill for product builders | Hamel Husain & Shreya Shankar (creators of the #1 eval course): https://www.lennysnewsletter.com/p/why-ai-evals-are-the-hottest-new-skill [ https://substack.com/redirect/cb379087-c198-44e0-b313-299c4bd094f2?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Beyond vibe checks: A PM’s complete guide to evals: https://www.lennysnewsletter.com/p/beyond-vibe-checks-a-pms-complete [ https://substack.com/redirect/8e5f5b77-3a6d-449c-8a66-eab01dbcca95?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Building eval systems that improve your AI product: https://www.lennysnewsletter.com/p/building-eval-systems-that-improve [ https://substack.com/redirect/ed48c5db-5446-4366-a75f-4d45efcf5f61?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Why experts writing AI evals is creating the fastest-growing companies in history | Brendan Foody (CEO of Mercor): https://www.lennysnewsletter.com/p/experts-writing-ai-evals-brendan-foody [ https://substack.com/redirect/edb84c9e-3cb4-484d-9597-d0fb0cd5f5da?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Judging by my tl there is a growing gap in understanding of AI capability: https://x.com/karpathy/status/2042334451611693415 [ https://substack.com/redirect/1433731b-9d76-464b-a06b-89254af1ec7b?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Formula 1: Drive to Survive on Netflix: https://www.netflix.com/title/80204890 [ https://substack.com/redirect/c9996328-a2d1-4307-a415-7f65aa755bbd?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Free Solo on National Geographic: https://films.nationalgeographic.com/free-solo [ https://substack.com/redirect/9d299216-9bfc-420d-8e37-8501e77bf076?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Alex Honnold: https://en.wikipedia.org/wiki/Alex_Honnold [ https://substack.com/redirect/b8e6ecfb-9c06-4003-8a64-58bf11343c7d?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Waymo: https://waymo.com [ https://substack.com/redirect/296333b6-7d89-4303-b902-111cca9bd5f7?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Recommended books:
• How Asia Works: https://www.amazon.com/How-Asia-Works-Joe-Studwell/dp/0802121322 [ https://substack.com/redirect/5ca30a0c-9ff6-4525-9169-9832199f1f34?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• The Technology Trap: Capital, Labor, and Power in the Age of Automation: https://www.amazon.com/Technology-Trap-Capital-Labor-Automation/dp/0691210799 [ https://substack.com/redirect/4312bccc-146e-411e-a915-2651d6858ac7?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• The Paper Menagerie and Other Stories: https://www.amazon.com/Paper-Menagerie-Other-Stories/dp/148142436X [ https://substack.com/redirect/25cfb36e-47f3-4772-a503-96c45971d283?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Production and marketing by https://penname.co/ [ https://substack.com/redirect/ec7447c8-97fc-4aea-a4ac-a62b23f8674f?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com [ mailto:podcast@lennyrachitsky.com ].
Lenny may be an investor in the companies discussed.
My biggest takeaways from this conversation:...
Unsubscribe https://substack.com/redirect/2/eyJlIjoiaHR0cHM6Ly93d3cubGVubnlzbmV3c2xldHRlci5jb20vYWN0aW9uL2Rpc2FibGVfZW1haWw_dG9rZW49ZXlKMWMyVnlYMmxrSWpvME1qWTFNVFV3TkRBc0luQnZjM1JmYVdRaU9qRTVOREl6TmpBd01pd2lhV0YwSWpveE56YzJPVFUzTkRRekxDSmxlSEFpT2pFNE1EZzBPVE0wTkRNc0ltbHpjeUk2SW5CMVlpMHhNRGcwTlNJc0luTjFZaUk2SW1ScGMyRmliR1ZmWlcxaGFXd2lmUS5xTkhCa1BrUmpXeU1icVI5RG9KdkhlNlZPRk9tLWZXSTRoQXN0WF83dEEwIiwicCI6MTk0MjM2MDAyLCJzIjoxMDg0NSwiZiI6dHJ1ZSwidSI6NDI2NTE1MDQwLCJpYXQiOjE3NzY5NTc0NDMsImV4cCI6MjA5MjUzMzQ0MywiaXNzIjoicHViLTAiLCJzdWIiOiJsaW5rLXJlZGlyZWN0In0.6Bca5guimKwOzk_LSrdcsrv_NDV0J0ZPKFXNW5y2vGA?
View Email
How Anthropic’s product team moves faster than anyone else | Cat Wu (Head of Product, Claude Code)
lenny@substack.com4/23/2026
SubstackView this post on the web at https://www.lennysnewsletter.com/p/new-a-free-year-of-cursor-google
👋 Hey there, I’m Lenny. Each week, I answer reader questions about building product, driving growth, and accelerating your career.
My mission with this newsletter (and podcast) is to give you the advice, community, and tools you need to build a world-class product and career. Because things are changing so fast, there’s a growing divide—in terms of career opportunities, financial outcomes, and how much you enjoy your work—between the people who benefit from the transformation we’re living through and those who get left behind. I want to make sure you’re in the first group.
To further that mission, I’m thrilled to announce that Lenny’s Product Pass [ https://substack.com/redirect/0a6231f1-6dd6-4c17-b5c2-f6e5433e1d25?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] now includes a free year of six additional incredible premium products:
Cursor [ https://substack.com/redirect/1b67d0fb-c65c-4fb9-a8e1-150133478bc4?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]* ($240 value): The best way to build software with AI.
Google AI [ https://substack.com/redirect/07e1d369-9cdd-4737-821a-62accd29792c?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]* ($240 value): Higher access to Gemini, NotebookLM, Antigravity, Nano Banana, Flow, 5 TB of cloud storage, and more.
Notion [ https://substack.com/redirect/51a1ce4a-f186-402b-9e60-52457833b3b5?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] ($240 value): Collaborative AI workspace where teams and agents work together.
Supabase [ https://substack.com/redirect/07d58023-67a5-4bb9-88b6-181e6d2a3acc?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]* ($300 value): An all-in-one, easy-to-use, open-source managed Database, Auth, Storage, Edge Functions, Realtime, and Vector search.
Fin + Intercom [ https://substack.com/redirect/4b2b9b54-ee81-4f8d-a243-f94c8d25557f?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] (5 seats and $100/month in AI outcome credits, $7,140 value): Deliver perfect customer experiences with the #1 AI customer service agent.
Gumloop [ https://substack.com/redirect/65a3081a-2e66-4c01-b0ff-ecb4a4ea866d?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] ($444 value): Build agents across all your apps and share them with your team. No engineering required.
→ Already a paid subscriber? Grab your free products here [ https://substack.com/redirect/0a6231f1-6dd6-4c17-b5c2-f6e5433e1d25?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ].
→ Not yet a subscriber? Subscribe [ https://substack.com/redirect/2efc0aa7-b297-4302-a011-c8ff7d8c76f2?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] and then grab your free products here [ https://substack.com/redirect/0a6231f1-6dd6-4c17-b5c2-f6e5433e1d25?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ].
I’m also super-excited to welcome back Replit and Gamma* to the Product Pass!
This is on top of the 17 premium products already available to subscribers: Canva Pro*, ChatPRD, ElevenLabs*, Factory, Framer, Granola, Linear, Lovable*, Magic Patterns, Manus, Mobbin, n8n*, PostHog, Railway, Stripe Atlas*, Warp, and Wispr Flow.
* These products are available for Insider-tier [ https://substack.com/redirect/cece2b4b-0c05-40a0-9b01-79beeb8d5fb3?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] subscribers only
The total value of the Product Pass is now over $30,000. That’s 27 of the hottest, most important, and most beautifully crafted products in the world, free with your Lenny’s Newsletter subscription.
This all sounds way too good to be true, but it isn’t.
Many readers expense this subscription out of their workplace’s learning and development budget. Here’s an email you can send to your manager [ https://substack.com/redirect/85c12118-5ac9-4848-9098-15ac05e2997a?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ].
Offer codes are limited and granted on a first-come, first-served basis. We’ll keep adding new products quarterly and rotating the collection to stay fresh.
How to redeem these offers:
Step 1: Get an Annual or Insider subscription [ https://substack.com/redirect/be5f4108-1507-4076-bbe7-4a04f58ec21d?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] to Lenny’s Newsletter.
Step 2: Redeem your codes here [ https://substack.com/redirect/8a06b773-5cd8-4a2f-93d1-2bb7f69d9b10?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ].
Step 3: Have fun!
A note about how I hope you’ll approach these offers
The Product Pass is a community-powered collaboration. Many of these companies are brand-new and very excited for our community to try their products. Companies aren’t paying to be in the Product Pass, and I only include tools that I love and recommend. Similarly, my (very small) team is working hard to make this a seamless experience. Things will break, codes will run out, and I promise we’ll do our very best to resolve issues as fast as we can. Ultimately, my core offering is this newsletter, the podcast, and the community. These deals are the cherry on top.
What are the new products?
1. Cursor Pro [ https://substack.com/redirect/1b67d0fb-c65c-4fb9-a8e1-150133478bc4?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]* ($240 value)
What it is: The best way to build software with AI.
How people use it:
Building a personal OS [ https://substack.com/redirect/910ab172-419a-483d-9f55-08613fe7b3d6?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] (while building AI product sense)
Structuring AI workflows to build and ship real products [ https://substack.com/redirect/68073a6c-152e-41a2-8f08-db939bba70a8?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] (even as a non-technical builder)
Accelerating PR velocity and code quality at scale [ https://substack.com/redirect/c4269d97-4b5d-461f-98fd-7291cd20bbf0?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
2. Google AI Pro [ https://substack.com/redirect/07e1d369-9cdd-4737-821a-62accd29792c?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]** ($240 value)
What it is: Get higher access to the newest and most powerful features in Gemini, Flow, and NotebookLM, as well as AI-powered assistance from Gemini directly in the Google apps you know and use. Plus, you get 5 TB of cloud storage to keep photos and files backed up.
How people use it:
Coding beautiful 3D pixel art [ https://substack.com/redirect/19c14a18-f5b6-4b18-a325-00886fc1db68?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] based on a single image prompt
Building a physics-consistent ocean waves simulator [ https://substack.com/redirect/3e170a49-f96d-4968-a9e2-f6f2630217ab?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Using Nano Banana 2 to create video game backgrounds [ https://substack.com/redirect/91741c76-6af5-4abc-ad9f-3c025168041d?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], UI design [ https://substack.com/redirect/830cccc6-46b8-4a67-8e2b-71802cf66ab6?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], home renovations [ https://substack.com/redirect/3b56efab-0e14-4598-ae0d-e6e1e8ac6b3a?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], and highly detailed imagery [ https://substack.com/redirect/b1b1d827-78fe-45f2-9bd2-f3b538bbee8a?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
3. Notion Business [ https://substack.com/redirect/51a1ce4a-f186-402b-9e60-52457833b3b5?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] ($240 value)
What it is: Collaborative AI workspace where teams and agents work together.
How people use it:
Running a Weekly Briefing agent [ https://substack.com/redirect/c6a5b3f2-c28f-43f5-b84e-2c960ce9f85e?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] that generates a summary of key updates, what’s coming up, and what needs attention that week
Building out an AI operating system for work [ https://substack.com/redirect/1b14eed2-9aaf-4e44-bfc6-2a87825f9c19?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], giving everyone at the company a personal Notion agent and cutting productivity-tool costs at Ramp
Using Notion as a lean “OS” [ https://substack.com/redirect/2ff75b24-85aa-4cc4-8780-9114d7adc0e9?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] where AI answers questions instantly, new hires onboard themselves, and every team builds exactly what they need at Cursor
Building a Scheduling Assistant agent that does meeting prep [ https://substack.com/redirect/ff07a101-b530-4cdc-acf1-8b0208712e0a?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]—automatically creating meeting notes, linking them to a CRM, and updating calendar events with links
4. Supabase Pro [ https://substack.com/redirect/07d58023-67a5-4bb9-88b6-181e6d2a3acc?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]* ($300 value)
What it is: An all-in-one, easy-to-use, open-source managed Database, Auth, Storage, Edge Functions, Realtime, and Vector search.
How people use it:
Building an app to learn English [ https://substack.com/redirect/88d2467e-22d0-49ec-a1a9-0f6df0b7c111?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Crafting a tool to upscale images and generate videos [ https://substack.com/redirect/62b013dd-1303-47bf-a28d-606c3739999c?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Hosting the database and analytics for a bulk URL shortener [ https://substack.com/redirect/aa964c99-2b33-4e69-8fee-e610549ca2be?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Creating an open source app for finding a home for your food scraps [ https://substack.com/redirect/0073fc68-980e-4aaa-905b-97cc944dfade?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
5. Fin AI Agent + Intercom Advanced [ https://substack.com/redirect/4b2b9b54-ee81-4f8d-a243-f94c8d25557f?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] (5 seats and $100/mo credits in AI outcomes, $7,140 value)
What it is: Deliver perfect customer experiences with an AI Customer Service Agent.
How people use it:
Transforming support operations for Anthropic [ https://substack.com/redirect/8c856784-beb9-48ac-b7df-48f6e8303811?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Supporting 50M users with 20 agents and Fin for Gamma [ https://substack.com/redirect/a6dbae6d-4d95-48b4-9224-6607b1af52a5?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Involving Fin in 90% of support queries and resolving 50% over email, chat, and Slack for Clay [ https://substack.com/redirect/8549b12a-59c8-40c8-9b61-21a24a9294be?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
6. Gumloop Pro [ https://substack.com/redirect/65a3081a-2e66-4c01-b0ff-ecb4a4ea866d?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] ($444 value)
What it is: An AI agent-building platform that makes it effortless for anyone on your team (not just engineers) to collaborate on and deploy agents. Describe exactly what tasks you want the agent to perform, when, and with which apps, and the agents will build themselves.
How people use it:
Using Gumloop agents to coach sales reps, prepare for renewal meetings, and monitor for clients at risk [ https://substack.com/redirect/3609054e-dd14-4d0a-9560-d062e79e40b1?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] of churning at Gusto
Instantly answering data analytics questions [ https://substack.com/redirect/2c305bd7-d68a-4dea-ba05-8cc3d57d3626?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] and making visualizations with an agent that any team member can @ in Slack
Building a sales agent [ https://substack.com/redirect/cfe6bf75-3fb6-4450-bf72-8a5d2d0a006a?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] that can update your CRM and research and schedule meetings with customers
Creating an automated personal assistant agent [ https://substack.com/redirect/14d7c441-234a-4734-abc0-5b6a4badb287?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] integrated with Granola MCP that can draft its own emails, Slack messages, and Linear tickets
Running an entire global support operation [ https://substack.com/redirect/5193fc14-e915-4d4b-b229-04360ddac825?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] by giving two humans a team of interconnected, specialized AI agents
Important offer details (read before subscribing):
For each product, you must be a new customer to take advantage of the free year. If you’ve already paid for one of the products yourself (monthly or yearly) or redeemed a code from one of our previous bundles, you won’t be able to get a free additional year of that specific product.
You must get an Annual or Insider subscription to Lenny’s Newsletter to be eligible for this offer. Monthly subscribers aren’t eligible.
Both existing and new subscribers of Lenny’s Newsletter are eligible for this deal. Existing subscribers can redeem the offer here [ https://substack.com/redirect/8a06b773-5cd8-4a2f-93d1-2bb7f69d9b10?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ].
We may run out of codes for a product at any time. Your code is only secured once you claim it [ https://substack.com/redirect/8a06b773-5cd8-4a2f-93d1-2bb7f69d9b10?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]. You need to claim each code individually, so hop on the products you are most excited about.
Your access to the Product Pass is contingent on your subscription remaining active. If you cancel or don’t renew your paid subscription at any time, your codes and active trials may be deactivated.
Your one free year of the product begins when you redeem the deal on the partner’s website, not when you purchase this newsletter subscription or claim your code.
All sales are final once you redeem your first code. We won’t issue refunds if a couple of products are out by the time you claim them. The deal is already so good, even if a couple of products are missing. If you request a chargeback for your subscription, all of your codes will be deactivated. We need to do this to avoid fraud.
To summarize, your paid subscription now includes:
A deeply researched newsletter and podcast with a 5+ year back catalog of evergreen content
A 30,000+ members-only global Slack community with local meetups, AMAs, mentorship programs, book clubs, and more
This growing collection of premium tools
It’s everything you need to build a world-class product and career.
* These products are available for Insider-tier [ https://substack.com/redirect/cece2b4b-0c05-40a0-9b01-79beeb8d5fb3?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] subscribers only
** Google AI Pro’s $239.88 value is based on monthly recurring subscription price. Redeem the offer by December 31, 2026, at 11:59 p.m. PT. Cancel anytime. Gemini in Google AI Pro and Gemini for Gmail, Docs, and more are only available for ages 18+. Gemini for Gmail, Docs, and more is available in select languages. Existing Google One users can redeem this offer, but this free trial period cannot be added to an existing free trial. Users can only use one trial at a time, and promotion lengths are not stackable. If a user has an existing trial and redeems a new trial, their existing trial or subscription plan will be revoked and their new trial will begin, regardless of how much time they have left on their existing offer. The offer is not available to: Google One users subscribed to an add-on, Google One users subscribed to a higher-tier plan than the one being offered, Google One users on a family plan who are not the plan manager, Google One users who have a Google One subscription through a third party or affiliate. See full terms [ https://substack.com/redirect/399950b2-d304-4764-a951-390399168287?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ].
If you’ve already got a subscription, consider gifting a subscription [ https://substack.com/redirect/3b119d50-0777-42de-b195-d9e2a832b84f?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] to a colleague or purchasing a group subscription [ https://substack.com/redirect/04909d3f-71ee-4b98-904b-db06b4ae3068?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] for your team.
Sincerely,
Lenny 👋
Unsubscribe https://substack.com/redirect/2/eyJlIjoiaHR0cHM6Ly93d3cubGVubnlzbmV3c2xldHRlci5jb20vYWN0aW9uL2Rpc2FibGVfZW1haWw_dG9rZW49ZXlKMWMyVnlYMmxrSWpvME1qWTFNVFV3TkRBc0luQnZjM1JmYVdRaU9qRTJOVEl3TkRjek1Td2lhV0YwSWpveE56YzJOemcwTnpFd0xDSmxlSEFpT2pFNE1EZ3pNakEzTVRBc0ltbHpjeUk2SW5CMVlpMHhNRGcwTlNJc0luTjFZaUk2SW1ScGMyRmliR1ZmWlcxaGFXd2lmUS4tTndaUHQ2RHdjakZDUy1sdEhQSWRHTmpnU3VVM2gxQm9DRXZNcWFsSUg4IiwicCI6MTY1MjA0NzMxLCJzIjoxMDg0NSwiZiI6dHJ1ZSwidSI6NDI2NTE1MDQwLCJpYXQiOjE3NzY3ODQ3MTAsImV4cCI6MjA5MjM2MDcxMCwiaXNzIjoicHViLTAiLCJzdWIiOiJsaW5rLXJlZGlyZWN0In0.XyJafwmu9qlJBLl-lf55rou87ELaT3j1hBRyK5YFWxI?
View Email
New: A free year of Cursor, Google AI Pro, Notion, Supabase, Gumloop, and Fin for subscribers
lenny@substack.com4/21/2026
SubstackView this post on the web at https://www.lennysnewsletter.com/p/why-half-of-product-managers-are-in-trouble
Nikhyl Singhal is the founder of The Skip, a community for senior product leaders; a former product exec at Meta, Google, and Credit Karma; and a many-time founder. He’s also one of the most honest, unfiltered voices on what’s actually happening in product management right now.
Listen on YouTube [ https://substack.com/redirect/90c8e454-ff89-4113-a5d0-6d5b72931334?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], Spotify [ https://substack.com/redirect/8eeed2ea-facc-4374-8430-16521f57b2a9?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], and Apple Podcasts [ https://substack.com/redirect/0fb31a15-a47a-4890-b7e8-43e6ad8e03b3?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
In our in-depth conversation, we discuss:
Why the next two years will be the most chaotic period in product management history
Why half of current product managers are at risk, and what separates those who’ll do well
Why you need to find your “moments of joy” with AI
The “smiling exhaustion” he’s seeing across the product community
The psychological barriers that prevent people from reinventing themselves
Why your resume’s fancy logos matter less than ever, and what matters now
His prediction that companies will shed 30,000 people and rehire 8,000—all AI-first
Brought to you by:
WorkOS [ https://substack.com/redirect/37624f8b-1d30-43d7-95f1-af58a95829b7?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]—Modern identity platform for B2B SaaS, free up to 1 million MAUs
Vanta [ https://substack.com/redirect/5b66e7cd-b8f1-48c8-81cc-c5a921549288?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]—Automate compliance, manage risk, and accelerate trust with AI
Where to find Nikhyl Singhal:
• LinkedIn: https://www.linkedin.com/in/nikhyl [ https://substack.com/redirect/3b05cb57-2ef7-4d33-805f-1b54aa419de0?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• X: https://x.com/nikhyl [ https://substack.com/redirect/896890c4-2b07-47cf-be59-d435e36017f2?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Podcast & Newsletter: https://skip.show [ https://substack.com/redirect/58ef351b-4944-46ba-b3a3-690b247e4f2b?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Skip Community: https://skip.community [ https://substack.com/redirect/9da71d72-a7b4-463d-b68e-c482dce59ce6?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Skip Coach: https:// [ https://substack.com/redirect/6d59e537-b9bc-434d-9708-8cb789665532?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]skip.coach [ https://substack.com/redirect/f4d811bf-6794-486c-a03b-5d1e2fcff02f?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Skip.help: https://skip.help [ https://substack.com/redirect/88719055-e242-4c4f-971f-785c4f450cfb?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Referenced:
• Building a long and meaningful career | Nikhyl Singhal (Meta, Google): https://www.lennysnewsletter.com/p/building-a-long-and-meaningful-career [ https://substack.com/redirect/a87d4740-35d6-45ab-a448-8e14e301489e?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• COBOL: https://en.wikipedia.org/wiki/COBOL [ https://substack.com/redirect/e51a2a8b-eece-4da7-b6b8-85d985b248b2?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• United Airlines: https://www.united.com [ https://substack.com/redirect/dbb088c1-1051-4396-8d22-e7616ec2b6af?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• State of the product job market in early 2026: https://www.lennysnewsletter.com/p/state-of-the-product-job-market-in-ee9 [ https://substack.com/redirect/1e1369c8-713a-47a3-a7bf-46d01faaf979?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Head of Growth (Anthropic): “Claude is growing itself at this point” | Amol Avasare: https://www.lennysnewsletter.com/p/anthropics-1b-to-19b-growth-run [ https://substack.com/redirect/968938c0-a6a9-4a77-b2e2-6499e2213bf8?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Demis Hassabis on X: https://x.com/demishassabis [ https://substack.com/redirect/21fc3dc9-8c49-4c92-9503-46b1308656e0?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Sam Altman on X: https://x.com/sama [ https://substack.com/redirect/89990e8a-bec4-4859-90a3-bac4ce0c91a7?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Dario Amodei on X: https://x.com/DarioAmodei [ https://substack.com/redirect/8ec3cf70-e87b-478c-8840-c61c1b0c2cd3?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Cross on Prime Video: https://www.amazon.com/Cross-Season-1/dp/B0D6X7ZZHC [ https://substack.com/redirect/cba7a399-eebd-445e-9739-86bd9f7c6cab?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Jack Ryan on Prime Video: https://www.amazon.com/Tom-Clancys-Jack-Ryan/dp/B0CNDCMN8R [ https://substack.com/redirect/4a781ac4-d6d6-41f8-ac05-a7212013fcb0?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• 24 on Prime Video: https://www.amazon.com/24-Season-1/dp/B000HPF85A [ https://substack.com/redirect/430af738-c13b-4ba4-8e9c-c5606f7ee509?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Claude Code: https://code.claude.com [ https://substack.com/redirect/58c0a7a1-063a-4068-8a80-536abe470256?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Codex: https://chatgpt.com/codex [ https://substack.com/redirect/d47ef2b1-6c18-46e5-87a2-01a77760cd0f?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Lovable: https://lovable.dev [ https://substack.com/redirect/9417df9d-bc23-4ed1-b677-742dd1672b8b?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Sonos: https://www.sonos.com [ https://substack.com/redirect/14f8773e-fc87-4238-b3d7-ae4ea7aaf78a?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• “There are only four jobs” on X: https://x.com/yrechtman/status/2039012253341495462 [ https://substack.com/redirect/1c6910e5-f278-4ba6-83f3-3e92d0cc0f8e?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Paradise on Hulu: https://www.hulu.com/series/paradise-2b4b8988-50c9-4097-bf93-bc34a99a5b4f [ https://substack.com/redirect/073865cb-fd5e-4f02-b482-5faa70ca3086?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Lioness on Paramount+: https://www.paramountplus.com/shows/lioness [ https://substack.com/redirect/64bd791b-05c8-4606-930c-0a3350462f1c?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Tesla: https://www.tesla.com [ https://substack.com/redirect/44779c44-bd26-461f-993c-94da09e2f272?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Albert Einstein’s quote: https://www.goodreads.com/quotes/115696-genius-is-1-talent-and-99-percent-hard-work [ https://substack.com/redirect/4406dc54-6ee1-41cc-a573-6ba0351bd393?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Recommended books:
• James: https://www.amazon.com/James-Novel-Percival-Everett/dp/0385550367 [ https://substack.com/redirect/93b7fc25-56a4-4057-bd26-042bf9e4bf40?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• The Adventures of Huckleberry Finn: https://www.amazon.com/Adventures-Huckleberry-Finn-Unabridged-Uncensored/dp/195483943X [ https://substack.com/redirect/8fc51819-832d-4fbd-974b-7112774cf5bf?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Production and marketing by https://penname.co/ [ https://substack.com/redirect/9e6f9435-7a6b-4218-af1c-1d0745cd3da4?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com [ mailto:podcast@lennyrachitsky.com ].
Lenny may be an investor in the companies discussed.
My biggest takeaways from this conversation:...
Unsubscribe https://substack.com/redirect/2/eyJlIjoiaHR0cHM6Ly93d3cubGVubnlzbmV3c2xldHRlci5jb20vYWN0aW9uL2Rpc2FibGVfZW1haWw_dG9rZW49ZXlKMWMyVnlYMmxrSWpvME1qWTFNVFV3TkRBc0luQnZjM1JmYVdRaU9qRTVNekV6TURFd01Td2lhV0YwSWpveE56YzJOakF5TnpjM0xDSmxlSEFpT2pFNE1EZ3hNemczTnpjc0ltbHpjeUk2SW5CMVlpMHhNRGcwTlNJc0luTjFZaUk2SW1ScGMyRmliR1ZmWlcxaGFXd2lmUS5falpIMHJVVFBwVjJfZUZNUE9MNmdDQnl1bGlXN1lHYVk0NlNJaXg5UERzIiwicCI6MTkzMTMwMTAxLCJzIjoxMDg0NSwiZiI6dHJ1ZSwidSI6NDI2NTE1MDQwLCJpYXQiOjE3NzY2MDI3NzcsImV4cCI6MjA5MjE3ODc3NywiaXNzIjoicHViLTAiLCJzdWIiOiJsaW5rLXJlZGlyZWN0In0.v4CIBzr-r4wTXRFa2J5040CX7gHD7CsWoD9P93B3mMQ?
View Email
Why half of product managers are in trouble | Nikhyl Singhal (Meta, Google)
lenny@substack.com4/19/2026
SubstackView this post on the web at https://www.lennysnewsletter.com/cp/194308203
Unsubscribe https://substack.com/redirect/2/eyJlIjoiaHR0cHM6Ly93d3cubGVubnlzbmV3c2xldHRlci5jb20vYWN0aW9uL2Rpc2FibGVfZW1haWw_dG9rZW49ZXlKMWMyVnlYMmxrSWpvME1qWTFNVFV3TkRBc0luQnZjM1JmYVdRaU9qRTVORE13T0RJd015d2lhV0YwSWpveE56YzJNalkyT0Rrd0xDSmxlSEFpT2pFNE1EYzRNREk0T1RBc0ltbHpjeUk2SW5CMVlpMHhNRGcwTlNJc0luTjFZaUk2SW1ScGMyRmliR1ZmWlcxaGFXd2lmUS5reE5Xb0pyYVNVdFNLLWdUbVlEUURJcmxoejZFNXFkbFJGNnRSbG5OTU1rIiwicCI6MTk0MzA4MjAzLCJzIjoxMDg0NSwiZiI6dHJ1ZSwidSI6NDI2NTE1MDQwLCJpYXQiOjE3NzYyNjY4OTAsImV4cCI6MjA5MTg0Mjg5MCwiaXNzIjoicHViLTAiLCJzdWIiOiJsaW5rLXJlZGlyZWN0In0.lzz6XZCixx7gj9CbairwJ1TZIY-fPo0RD4tx3RLTXHQ?
View Email
What PM Hiring Managers Actually Screen For
lenny@substack.com4/15/2026
SubstackView this post on the web at https://www.lennysnewsletter.com/p/not-all-ai-agents-are-created-equal
👋 Hey there, I’m Lenny. Each week, I answer reader questions about building product, driving growth, and accelerating your career. For more: Lenny’s Podcast [ https://substack.com/redirect/54cd31a3-545a-4f2a-8a7d-c113a5365423?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] | Lennybot [ https://substack.com/redirect/9b262fa5-a0a6-4d5a-9d65-8e8a2bcd270b?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] | How I AI [ https://substack.com/redirect/1189fd97-8fd7-4b43-af36-0568e4b1884a?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] | My favorite AI/PM courses [ https://substack.com/redirect/e3509bc0-5a6b-4d80-8ebf-a644e91b0d2a?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], public speaking course [ https://substack.com/redirect/3a94d6a1-a563-4b9d-9b72-7d4758a0c9ba?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], and interview prep copilot [ https://substack.com/redirect/2820def0-303d-423a-beb1-0de08c693183?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
P.S. Get a full free year of Lovable, Manus, Replit, Gamma, n8n, Canva, ElevenLabs, Amp, Factory, Devin, Bolt, Wispr Flow, Linear, PostHog, Framer, Railway, Granola, Warp, Perplexity, Magic Patterns, Mobbin, ChatPRD, and Stripe Atlas by becoming an Insider subscriber [ https://substack.com/redirect/8ba2034b-b21c-45c9-bc3a-790bf3fbe96a?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]. Yes, this is for real [ https://substack.com/redirect/ce069312-df26-4ba0-86d7-a367d13e3211?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ].
Agents are so hot right now. Every other day, someone’s launching a new one or a new tool to manage them. I bet your team has a half-dozen agent ideas on your backlog right now. None of this means you actually need to build an agent today. But it does mean that you need to understand how agents fit into your broader strategy, and what the right investment looks like.
Hamza Farooq [ https://substack.com/redirect/ea668da7-f9f1-4214-b1f5-f9cfadc49bbd?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] and Jaya Rajwani [ https://substack.com/redirect/b5c15af6-0c5d-4355-91b1-bf124013d829?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] teach two of the most highly rated and well-respected courses on building AI agents (Agent Engineering Bootcamp [ https://substack.com/redirect/6172d329-4830-4304-a06a-3b0620ae4c73?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] and Agentic AI for PMs [ https://substack.com/redirect/c272b338-d895-4456-9d3d-baba1170b473?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]) and spent over 50 hours putting this guide together. By the time you finish reading this post, you’ll understand the three types of agents, how to decide which initiatives to prioritize, and how to avoid common pitfalls—with specific recommended tools and platforms and tons of real-life examples.
Let’s get into it.
P.S. You can listen to this post in convenient podcast form: Spotify [ https://substack.com/redirect/da9634bc-70f6-4e73-b292-5fdf68f024b1?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] / Apple [ https://substack.com/redirect/00ac9c58-cf66-4880-a8fb-ecfc4324f22e?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] / YouTube [ https://substack.com/redirect/ca834045-f60a-4651-ab08-71b22be49edd?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ].
Over the past year, we’ve had the same conversation at least 30 times. An AI leader pulls up their roadmap, usually 5 to 10 “agent” initiatives, and says, “Help us figure out which one to build first.”
The list usually includes a PM assistant, a RAG copilot, a customer support system, a code review agent, and a voice-enabled shopping assistant
If you’re reading this, you probably have a similar list. Your team is energized, investors are asking about it, competitors are announcing agent launches. You need to pick something and ship it.
That’s where most teams get stuck. The problem isn’t that they lack ideas; it’s that they try to prioritize fundamentally different kinds of systems as if they were the same thing. The usual approach is to reach for familiar planning tools. Teams open an impact-vs.-effort matrix and try to compare ideas side by side.
But with AI agents, that quickly falls apart. One “agent” might take six weeks to build. Another might take six months. One can be assembled by a product manager using n8n. Another requires a dedicated ML engineering team. One costs $500 per month to operate. Another could generate a six-figure annual LLM bill.
A customer support assistant and a voice-enabled shopping agent may both be called agents, but they demand different architectures, different teams, different infrastructure, and different timelines. Until you recognize those differences, any attempt to compare “effort” or “impact” is essentially guesswork.
Treating architecturally different products as if they’re in the same category makes effective prioritization nearly impossible. Prioritization breaks not because teams are bad at planning but because they’re comparing apples, oranges, and jet engines on the same spreadsheet.
The missing step is hierarchy
Before you can decide which agent to build first, you need to answer a more basic question: What type of agent is each idea actually proposing?
This will determine almost everything that matters for planning:
How complex it will be to build
What skills and infrastructure are required
How long it is likely to take
How expensive it will be to operate
How you should measure success
In other words, categorization isn’t just a technical exercise. It’s the foundation for smart prioritization.
This post gives you a decision framework you can start using today with your current roadmap.
We developed this framework from patterns we’ve seen while helping organizations turn agent ideas into real production systems. Working with enterprise teams across Fortune 500 companies such as Jack in the Box, Tripadvisor, and The Home Depot, we found that grouping ideas by their underlying architecture unlocks prioritization and significantly speeds up the development and launch process. These distinctions also mirror how the broader industry is beginning to classify AI agents, from automation workflows to reasoning systems and multi-agent networks (like the Levels of Autonomy for AI Agents [ https://substack.com/redirect/b8187cd7-482f-42df-a3f1-dc8fa07c0583?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] paper and Types of AI agents [ https://substack.com/redirect/710da527-c835-4b86-97d3-a9af4d3235de?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] by IBM). These are also the foundations of how massively popular tools like OpenClaw and Claude Code are actually architected.
If you’re staring at a backlog of agent ideas trying to figure out what to build first, here’s what you’ll have by the end of this post:
A 5-minute triage process to categorize every agent idea into one of three architectural types
A guide to picking the right tool/platform for your project (i.e. when to use n8n vs. LangGraph vs. ADK)
Success metrics and ROI frameworks tailored to each architectural type
Warning signs that you’ve picked the wrong path (and how to fix it)
You’ll be able to look at your backlog and know which ideas can ship in six weeks for quick ROI, which need three months but will drive significant revenue growth, and which are a six-month bet that only makes sense with the right resourcing and expectation setting.
All by first recognizing that “agent” is an umbrella term for very different kinds of systems.
The three agent categories
Every “agent” idea falls into one of three architectural categories.
Category 1: Deterministic automation
You define the entire flow. AI handles content at specific steps. Think: n8n or Zapier workflows with LLM nodes. This is where the majority of agent opportunities belong and where most teams should start. These projects are fastest to launch and deliver measurable ROI quickly.
Category 2: Reasoning and acting agents
AI decides what to do next, using available tools. Think: Cursor, Lovable, or agents built with LangGraph, CrewAI, Google ADK, etc. These initiatives typically come after Category 1, when higher-value problems require flexibility and dynamic decision-making that workflows alone can’t handle.
Category 3: Multi-agent networks
Multiple specialized agents coordinate with each other. Think: enterprise systems built with ADK or AutoGen. These projects are typically reserved for later stages, when multiple teams must coordinate across domains, and should almost never be the starting point on a roadmap.
Some examples of “agents” that fit into each category to help you understand the differences:
Organizations often try to build Category 1 problems with Category 2 frameworks—overengineering solutions that add unnecessary complexity and cost. Less frequently but with worse outcomes, they try to solve Category 2 problems with Category 1 tools, and it breaks in production because the tool is not robust enough.
Let’s take a deeper dive into each category, starting with the workhorse, Category 1.
Category 1: Deterministic automation
What this is
These are workflows where you define every step, every branch, every decision point. An LLM handles natural language understanding and generation at specific nodes, but you control the flow. Think of them as intelligent flowcharts where you design the path and AI handles the content.
Tools most commonly used for deterministic automation are n8n, Zapier, Make.com, OpenAI AgentKit, Lindy, and Gumloop. These tools are built around explicit triggers and predefined branching logic. You define the workflow, while LLMs are used only for classification, extraction, or drafting within those boundaries.
How to prioritize Category 1 products
If your backlog includes a mix of agent ideas, Category 1 projects are almost always the smartest place to begin. These initiatives tend to be the simplest to plan and the lowest-risk to execute.
They’re best suited to situations where the process is already well-defined and the goal is to automate repetitive, high-volume work. If you need quick, measurable ROI, have limited AI engineering capacity, or are under pressure to deliver results in weeks rather than months, Category 1 projects are almost always the right starting point.
Most initiatives in this category share a similar profile across certain criteria:
That combination of fast timelines, modest resources, and clear business impact is what makes Category 1 initiatives such powerful early wins. They generate near-term value while building organizational confidence for more advanced efforts later.
What types of products fall in this category
If you can map the entire process as a flowchart with clear decision points, a product belongs in Category 1. Here are some more traits of a Category 1 product:
Execution paths are finite and predictable (fewer than 15 to 20 branches)
Task completion needs to happen in seconds to minutes
The value is in automating a known process, not discovering new approaches
In our experience with customers, this covers 60% to 70% of agent opportunities. Revisiting the typical list of opportunities I mentioned above, here is a great example of a Category 1 product: “We need an AI agent to handle incoming customer emails, read them, understand what they’re asking, pull relevant information from our docs, draft replies, and route to our team for approval.”
At first, this sounds like it needs sophisticated reasoning. But when you map out what actually needs to happen, it’s remarkably deterministic:
Every step is predictable. The “intelligence” is in understanding the email and generating a good response, not in figuring out what to do next. This is Category 1.
There are a ton of great examples of automation agents; here’s [ https://substack.com/redirect/848794e9-e9b0-4066-bb4e-f6b4dbc309df?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] one built by me.
I love Airbnb, but I hate spending long hours finding the best ones, so I built an agent that will take my exact request for, e.g., “Modern apartment in Paris near train stations from 20th March to 26th March. Great for a couple” (more than 10,000 users have used it) and run a search. Here’s [ https://substack.com/redirect/5c86dece-95a0-4730-b907-b1f791146dd3?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] how you can build your own.
Other examples of Category 1 “agents”:
a travel planning agent
a voice-enabled book companion agent
a content automation agent (YouTube → LinkedIn)
a knowledge base of your organization with internet search (Perplexity clone)
an agent that generates deeply researched blogs, based on a given topic
a highly personalized calorie counter app that allows you to upload images of your meals to keep track of your daily caloric intake and recommends better dietary choices and exercises
How to evaluate Category 1 products
The metrics below are designed to answer a simple question: Did this agent automate the right process, or should this idea be reconsidered or re-scoped?
A deterministic agent built for the email automation process can be evaluated as follows:
Workflow completion rate: % of executions that finish successfully
Automation rate: % of requests handled without human intervention
Accuracy: correctness of intent classification, data extraction, and routing decisions
Latency: time from trigger to final output (P50/P95 if relevant)
Cost per workflow: total LLM and API cost per completed run
Error rate: % of runs failing due to tool, integration, or system errors
Human review rate: % of runs requiring manual approval or intervention
Here are workflow completion rate metrics from a real-life example of a Category 1 product, an email support agent built by a SaaS company we worked with:
Week 1: 52% completion rate (lots of edge cases discovered)
Week 4: 78% completion rate (refined classification logic)
Week 8: 87% completion rate (stable, production-ready)
Result: 3,000 support emails/month automated, 2.5 FTE hours/day freed, $18K/month savings
When these metrics stabilize and cost trends downward, the workflow is doing what it should. If completion remains low or manual intervention stays high, the problem may not be deterministic enough for this category.
How to know you’ve outgrown Category 1
You’ll know you need a different architecture when:
Your flowchart has 30+ nodes and you’re adding new branches every week
Customers phrase things in ways you can’t anticipate, and mapping all variations is impossible
The agent needs to decide which API or knowledge source to use based on context, not follow a predetermined path
Breaking down ambiguous requests requires exploration and adaptation, not predefined decomposition
The highest-value opportunities can no longer be expressed as predictable workflows
Most quick-win processes are already automated
If several of these signals are present at once, the problem is no longer a good fit for a deterministic workflow, and you should consider Category 2.
Category 2: Reasoning and acting agents (ReAct)
What this is
Instead of defining the flow, you define the available tools, and an LLM autonomously decides what to do next. The agent operates in a loop: observe → reason → act → observe result → repeat.
The key characteristic: you control the tools; the LLM controls the reasoning.
Tools most commonly used for building ReAct agents include LangGraph, CrewAI, AutoGen, and other agent orchestration libraries that support tool use, memory, and dynamic planning.
How to prioritize Category 2 products
Category 2 is for situations where user requests are ambiguous, workflows cannot be mapped in advance, and real value comes from flexible, contextual decision-making. If you need agents that can reason across multiple tools, handle conversational interactions, or adapt dynamically to new inputs, that’s a Category 2 product.
Category 2 products are more complex to plan and carry higher execution risk than Category 1. Most initiatives in this category share a similar profile:
The combination of longer timelines, specialized expertise, and higher costs is what makes Category 2 initiatives powerful but more demanding than Category 1. If your backlog includes problems that truly require reasoning and dynamic behavior, prioritizing Category 2 projects becomes essential. They unlock use cases that deterministic automation cannot handle and enable more advanced, high-impact agent experiences.
What types of products fall in this category
A product belongs in Category 2 if the same user request can trigger different action sequences every time. That means that you don’t determine the path; the LLM does. That’s the key difference from Category 1. Here are some more traits of a Category 2 product:
The same high-level task requires different sequences of actions depending on input
You have 5-15+ distinct capabilities and the right one depends on context
User intent is ambiguous and needs clarification through interaction
Multiple input modalities (voice, image, text) need to be understood contextually
Breaking down complex requests into sub-tasks is part of the value
In our work with customers, this is the right choice for 25% to 30% of agent opportunities. For an example of this type of product, let’s return to the voice-enabled shopping assistant opportunity from the start of this post.
Customers should be able to search products by voice, upload images to find similar items, check order status, update preferences, and initiate returns, all through conversation.
At first, this sounds like Category 1. Just map out the intents and route accordingly, right? But in practice, real conversations don’t follow fixed paths. To see why, let’s walk through one interaction.
A customer uploads a photo of shoes and says:
“These are too small. I need a size up, and I want them delivered by Thursday.”
Here’s what happens under the hood:
Observe. The agent receives mixed input: an image + voice request.
Reason. It determines:
First, identify the product in the image
Then, find available size variants
Then, check delivery dates
Finally, confirm the order with the user
Act. The agent dynamically selects tools:
visual_search() → identify product
check_inventory() → find size-up availability
get_delivery_options() → verify Thursday delivery
place_order() → after confirmation
Observe result → reason again. Each tool response updates the agent’s state and influences the next step.
This sequence cannot be pre-defined.
If the item is out of stock, the agent may suggest alternatives.
If Thursday delivery isn’t available, it may propose pickup.
If the image can’t be recognized, it asks a clarifying question.
The same user request triggers different action sequences based on reasoned considerations.
Other examples of Category 2 “agents”:
a conversational customer support agent
a code assistant that modifies repositories, e.g. Claude Code
an intelligent personal shopping assistant
an IT troubleshooting agent
a sales copilot that researches accounts and drafts outreach
a multimodal assistant combining voice, image, and text
How to evaluate Category 2 products
Reasoning agents should be evaluated on whether they help users achieve their goals across variable paths, while remaining efficient enough to justify their cost.
These metrics answer the question: Was dynamic reasoning necessary, or should the problem be simplified to a lower category?
Task completion rate: % of sessions where users achieve their intended goal
Reasoning accuracy: correctness of task decomposition, tool selection, and decision ordering
Conversation length: average turns to resolution
Multimodal accuracy: correctness of image, voice, or structured input interpretation (if applicable)
Tool call efficiency: average number of tool calls per successful session
Latency: time per turn and end-to-end session duration
Cost per session: total LLM and API cost per completed interaction
User satisfaction: post-interaction CSAT or equivalent signal
Business impact: lift in conversion, retention, or task success versus baseline
Here are some metrics from a real-life example, a voice + image shopping assistant for a home goods retailer we built:
Month 1: 71% task completion, longer conversations, higher tool usage, $0.12 cost per session
Month 4: 86% task completion, shorter conversations, fewer tool calls, $0.08 cost per session
Result: Image identification accuracy improved from 76% to 91%, conversion lift increased from +8% to +22%, and CSAT rose from 4.0 to 4.5.
When task completion improves while conversation length, tool usage, and cost per session decline, the agent’s reasoning loop is adding value. If performance stalls while costs remain high, the problem may be over-scoped or better served by the deterministic approach of Category 1 tools.
How to know you’ve outgrown Category 2
You’ll know you need a different architecture when:
Your single agent is trying to handle too many domains (customer service + inventory + logistics + finance) and performance is degrading
You need agents to delegate tasks to each other, not just call stateless APIs. Example: A shopping agent needs to ask an inventory agent, “Can you check all warehouses and suggest alternatives?”
Tasks take hours or days to complete (like the automated eval agent analyzing 10,000 conversations overnight)
You need hundreds of agent instances running in parallel, coordinating work among them
Different teams want to own their specialized agents, but they need to work together
If you’re hitting two to three or more of these, it’s time to consider Category 3 tools and approaches.
Category 3: Multi-agent network
What this is
Instead of one agent calling tools, you have multiple specialized agents that coordinate with each other. Each agent is owned by a different team, handles its own domain, and can request help from other agents...
Unsubscribe https://substack.com/redirect/2/eyJlIjoiaHR0cHM6Ly93d3cubGVubnlzbmV3c2xldHRlci5jb20vYWN0aW9uL2Rpc2FibGVfZW1haWw_dG9rZW49ZXlKMWMyVnlYMmxrSWpvME1qWTFNVFV3TkRBc0luQnZjM1JmYVdRaU9qRTVNelV4TWpZMk9Dd2lhV0YwSWpveE56YzJNVGN4TlRRMExDSmxlSEFpT2pFNE1EYzNNRGMxTkRRc0ltbHpjeUk2SW5CMVlpMHhNRGcwTlNJc0luTjFZaUk2SW1ScGMyRmliR1ZmWlcxaGFXd2lmUS5TckZ4M1h3aDl1Nkt6NkZyVEhsVTk3ckRpdFc0UnlHRndVS0V2dDB5bThVIiwicCI6MTkzNTEyNjY4LCJzIjoxMDg0NSwiZiI6dHJ1ZSwidSI6NDI2NTE1MDQwLCJpYXQiOjE3NzYxNzE1NDQsImV4cCI6MjA5MTc0NzU0NCwiaXNzIjoicHViLTAiLCJzdWIiOiJsaW5rLXJlZGlyZWN0In0.WVVqD78fbGGvbMEYCmWKXADf-D724h-SaY3bM4RDfQc?
View Email
Not all AI agents are created equal
lenny@substack.com4/14/2026
SubstackView this post on the web at https://www.lennysnewsletter.com/p/hard-truths-about-building-in-the-ai-era
Keith Rabois was an early executive at PayPal (part of the famous PayPal Mafia), COO at Square, VP of Corporate Development at LinkedIn, and an early investor in Stripe, DoorDash, Airbnb, YouTube, Ramp, and Palantir. Currently he’s managing director at Khosla Ventures. Also, he hasn’t touched a computer since September 2010 (he does everything from an iPad).
Listen on YouTube [ https://substack.com/redirect/e9381061-abbc-4ac4-8b85-6358e8a23fa9?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], Spotify [ https://substack.com/redirect/34f97ed7-a905-45f4-8e4b-17d1062ebd42?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], and Apple Podcasts [ https://substack.com/redirect/3c2ed2a6-34b9-47b3-a862-efa6232a8f5c?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
In our in-depth conversation, Keith shares:
The barrels vs. ammunition hiring framework (and how to spot barrels)
Why talking to customers is actively harmful for consumer products
How to identify undiscovered talent
Why the PM role is dying
The three traits of the best-performing companies right now
The specific interview question he asks every senior candidate
Why CMOs (not engineers) are becoming the #1 consumer of tokens
Brought to you by:
WorkOS [ https://substack.com/redirect/8db48cfb-fa25-4772-bf29-8cdc3d5066ed?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]—Modern identity platform for B2B SaaS, free up to 1 million MAUs
Vanta [ https://substack.com/redirect/1c621fe5-2ae5-4c2b-9d14-252c761d14fb?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]—automate compliance, manage risk, and accelerate trust with AI
Where to find Keith Rabois:
• X: https://x.com/rabois [ https://substack.com/redirect/3c899904-1d28-432c-84e2-d10dc307ed7e?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• LinkedIn: linkedin.com/in/keith [ https://substack.com/redirect/54e0902d-d8d0-4b10-85ab-9fe7b63af3f5?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Website: https://www.khoslaventures.com [ https://substack.com/redirect/f1b60594-7115-4763-b4f3-01f9716a9e69?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Referenced:
• Square: https://squareup.com [ https://substack.com/redirect/8cc9d1b8-2f04-45d1-8a6b-08f55d875c3d?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Jack Dorsey on X: https://x.com/jack [ https://substack.com/redirect/dcabd391-40af-413f-be18-1e13b04f4ccc?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Head of Claude Code: What happens after coding is solved | Boris Cherny: https://www.lennysnewsletter.com/p/head-of-claude-code-what-happens [ https://substack.com/redirect/94c32b75-2d59-4591-ad0d-c6f9868ad6ed?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Simon Willison’s Weblog: https://simonwillison.net [ https://substack.com/redirect/59b3195d-2f36-4609-b9d0-de4d5b9eef70?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Vinod Khosla on X: https://x.com/vkhosla [ https://substack.com/redirect/1c751cce-cab0-48d5-b5e0-97ebb538a1de?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Peter Thiel on X: https://x.com/peterthiel [ https://substack.com/redirect/f5a8ed06-5f3e-4c50-ab18-d8ede5ae4526?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Max Levchin on X: https://x.com/mlevchin [ https://substack.com/redirect/65d73586-7343-45fd-994e-3f77d1f9f0b6?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• David Sacks on LinkedIn: https://www.linkedin.com/in/davidoliversacks [ https://substack.com/redirect/c6d0772c-d4d6-4896-9297-06bebafe0b02?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Tony Xu on X: https://x.com/t_xu [ https://substack.com/redirect/db2958da-8b59-4bc2-96d2-19b17e863f10?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• David Sze on X: https://x.com/davidsze [ https://substack.com/redirect/af810cd0-1f4f-4800-8b8b-cbce11b2992f?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Faire: https://www.faire.com [ https://substack.com/redirect/07505d64-6eef-4d80-8e5b-3b66e00f5929?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Max Rhodes on X: https://x.com/MaxRhodesOK [ https://substack.com/redirect/6bb038d7-c393-44bb-8b0f-893578f1912f?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Jeffrey Kolovson on LinkedIn: https://www.linkedin.com/in/jeffreykolovson [ https://substack.com/redirect/f35b70f2-5cb6-431b-9218-016526c19ee1?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Uncapped | Comparative Advantages w/ Keith Rabois: https://www.khoslaventures.com/posts/uncapped-comparative-advantages-w-keith-rabois [ https://substack.com/redirect/e5f41443-d774-449f-a1f9-a2f0eba48a95?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Lattice: https://lattice.com [ https://substack.com/redirect/c2d1f09a-9536-4f72-a3c1-d6efed075a97?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Taylor Francis on LinkedIn: https://www.linkedin.com/in/taylor-francis-4ba49640 [ https://substack.com/redirect/3036f5ea-0145-462a-ba08-f02cdbe3646e?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Building product at Stripe: craft, metrics, and customer obsession | Jeff Weinstein (Product lead): https://www.lennysnewsletter.com/p/building-product-at-stripe-jeff-weinstein [ https://substack.com/redirect/2181d568-7fb0-42b0-97ff-d10e6b10edee?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• The art of hiring: insights from Khosla Ventures, Airbnb, Ramp and Traba: https://ramp.com/velocity/the-art-of-hiring-insights [ https://substack.com/redirect/3afe9c7a-a6ff-4113-8a8f-7a15eb713571?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Eric Glyman: Seek out super individual contributors (ICs): https://ramp.com/velocity/the-art-of-hiring-insights#Eric-Glyman:-Seek-out-super-individual-contributors-(ICs) [ https://substack.com/redirect/b2c8f6c1-6e2a-4cf1-81ee-5829ca3aa964?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Eric Glyman on X: https://x.com/eglyman [ https://substack.com/redirect/d93ce055-0f23-456c-baab-d5d5308ae834?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Mike Moore on LinkedIn: https://www.linkedin.com/in/mike-moore-802223177 [ https://substack.com/redirect/2891c754-95c2-4e58-8425-9bb31fdcc1af?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Brian Chesky’s new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach [ https://substack.com/redirect/a30a95c2-c43c-40f2-8350-d58dd4989e34?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Why you should work much harder RIGHT NOW: https://marginalrevolution.com/marginalrevolution/2026/03/why-you-should-work-much-harder-right-now.html [ https://substack.com/redirect/bed4465a-70c3-4b01-a2b9-d96abeefbd7b?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Opendoor: https://www.opendoor.com [ https://substack.com/redirect/e55c315e-d970-4301-9d70-62b61225c4e7?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• The Craft of Early Stage Venture | Peter Fenton, General Partner at Benchmark | Uncapped with Jack Altman: https://www.youtube.com/watch?v=vRiblwiXt-Q [ https://substack.com/redirect/662159ce-fc8c-4bce-b4aa-b83d978c48e1?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Lovable: https://lovable.dev [ https://substack.com/redirect/940608ee-26d0-446b-8a94-c44e88ad18cf?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• The rise of the professional vibe coder (a new AI-era job) | Lazar Jovanovic (Professional Vibe Coder): https://www.lennysnewsletter.com/p/getting-paid-to-vibe-code [ https://substack.com/redirect/761401ae-4ee1-4790-9ed0-8ab81c763e41?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Building Lovable: $10M ARR in 60 days with 15 people | Anton Osika (co-founder and CEO): https://www.lennysnewsletter.com/p/building-lovable-anton-osika [ https://substack.com/redirect/61460354-d034-44a7-9227-d8313dc42338?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Marc Andreessen: The real AI boom hasn’t even started yet: https://www.lennysnewsletter.com/p/marc-andreessen-the-real-ai-boom [ https://substack.com/redirect/7ee4855e-05ee-445c-9cab-d4278cd925b5?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Jeremy Stoppelman on X: https://x.com/jeremys [ https://substack.com/redirect/c0b18266-1b53-407b-802d-ba9c05c81617?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• The design process is dead. Here’s what’s replacing it. | Jenny Wen (head of design at Claude): https://www.lennysnewsletter.com/p/the-design-process-is-dead [ https://substack.com/redirect/125f2543-fb91-4bed-bdd0-a36e8734d0ad?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Andy Warhol: https://en.wikipedia.org/wiki/Andy_Warhol [ https://substack.com/redirect/0e721ed4-c3f9-4231-9d81-e6786d6924d3?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Curation and Algorithms: https://stratechery.com/2015/curation-and-algorithms [ https://substack.com/redirect/5ea0dadf-b70e-4ddf-a9af-2ba3a8cb5af9?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Ernest Hemingway: https://en.wikipedia.org/wiki/Ernest_Hemingway [ https://substack.com/redirect/93d3e67a-7c65-4c12-b154-ded7e17ec054?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• William Shakespeare: https://en.wikipedia.org/wiki/William_Shakespeare [ https://substack.com/redirect/ec176864-b63b-4baf-bc6f-f181499603e2?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Evan Moore on X: https://x.com/evancharles [ https://substack.com/redirect/d1790dc0-63bd-4a78-9c99-2b12a1cbbb24?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Andrew Mason on X: https://x.com/andrewmason [ https://substack.com/redirect/eef0d7bb-42ab-450d-b12e-2a355ca606a0?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Read Taylor Swift’s Full Viral Speech After Record-Breaking Awards Sweep: https://www.newsweek.com/entertainment/read-taylor-swift-full-acceptance-speech-record-breaking-awards-sweep-11745941 [ https://substack.com/redirect/daa503a2-bc20-4e6a-9b2f-2a28c07b92a1?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• The Chainsmokers: Stories Behind the Songs, AI’s Impact on Music, and Venture Investing | Uncapped with Jack Altman: https://www.youtube.com/watch?v=9GMSC-2pYnw&list=PLtpH7YnTL8ihy0nR2BV32n5VkRtqlDAS1&index=16 [ https://substack.com/redirect/207dfe8a-0a4d-44d4-8360-7d4e23e95e8d?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• How to spot a top 1% startup early: https://www.lennysnewsletter.com/p/how-to-spot-a-top-1-startup-early [ https://substack.com/redirect/3689aece-cf18-4627-bfac-ce45afdcec6e?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• David Weiden on LinkedIn: https://www.linkedin.com/in/davidweiden [ https://substack.com/redirect/a7f5ed5b-415c-41eb-b71d-fb3f4f376d1d?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Alfred Lin on LinkedIn: https://www.linkedin.com/in/linalfred [ https://substack.com/redirect/b29d94a4-a003-409c-83ee-f422a11eab77?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Keith’s post about vertical integration on X: https://x.com/rabois/status/870673635375104000 [ https://substack.com/redirect/422c6944-1bea-4d7a-bc37-c6a68ec322fc?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Jon Chu on X: https://x.com/jonchu [ https://substack.com/redirect/d9d952b4-f0ba-4583-9f52-26d69ac07fa5?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Kanu Gulati on X: https://x.com/KanuGulati [ https://substack.com/redirect/5b21a0d5-63ce-4a05-9b9b-de6b880d03d3?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Rogo: https://rogo.ai [ https://substack.com/redirect/f9da8d52-2422-44db-b3db-91da6dea2f90?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Profound: https://www.tryprofound.com [ https://substack.com/redirect/c51cc19e-98aa-4e6c-a753-da260421fe86?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Basis: https://www.getbasis.ai [ https://substack.com/redirect/48b62848-ced3-4a1d-a2be-727af8253b1a?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Spellbook: https://www.spellbook.legal [ https://substack.com/redirect/c82c0ecd-2305-42eb-926e-29d8c8563c32?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Roelof Botha on X: https://x.com/roelofbotha [ https://substack.com/redirect/2c7a9e95-a433-4601-9c33-4a6f6c0d1571?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Delian Asparouhov on LinkedIn: https://www.linkedin.com/in/delian-asparouhov-87447742 [ https://substack.com/redirect/4cd067c0-d7a6-4d01-87ad-9082168ee41e?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Lessons From Keith Rabois, Essay 1: How to become a Venture Capitalist: https://delian.io/lessons-1 [ https://substack.com/redirect/bd2476cf-28a2-4726-838d-f22e6501d3fc?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Velocity over everything: How Ramp became the fastest-growing SaaS startup of all time | Geoff Charles (VP of Product): https://www.lennysnewsletter.com/p/velocity-over-everything-how-ramp [ https://substack.com/redirect/15b79ad6-dc69-4c94-b4b3-426575d79725?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Nuremberg on AppleTV+: https://tv.apple.com/us/movie/nuremberg/umc.cmc.3sg4y0382byupy76bfy7307k4 [ https://substack.com/redirect/1acbc219-72bb-421a-b0d8-0a11f17e7b51?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Eight Sleep: https://www.eightsleep.com [ https://substack.com/redirect/637356b4-d01f-485e-8f2f-b28a013d9cd7?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• “NO DAYS OFF”—Bill Belichick on X: https://x.com/SNFonNBC/status/829036279069364224 [ https://substack.com/redirect/0fad15f1-d96c-4863-91c1-58774b81addf?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Recommended books:
• Creativity, Inc.: Overcoming the Unseen Forces That Stand in the Way of True Inspiration: https://www.amazon.com/Creativity-Inc-Overcoming-Unseen-Inspiration/dp/0812993012 [ https://substack.com/redirect/05f424f4-bf2c-4c8b-b97b-b704e57d1836?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• The Jordan Rules: The Inside Story of One Turbulent Season with Michael Jordan and the Chicago Bulls: https://www.amazon.com/Jordan-Rules-Sam-Smith/dp/0671796666 [ https://substack.com/redirect/f5f4c776-66bb-49df-939f-3baef0298f82?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• The Upside of Stress: Why Stress Is Good for You, and How to Get Good at It: https://www.amazon.com/Upside-Stress-Why-Good-You/dp/1101982934 [ https://substack.com/redirect/6b2d8a37-6502-43e7-8c65-615b9e231c04?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Production and marketing by https://penname.co/ [ https://substack.com/redirect/91ebdd55-1b83-479f-b6d5-4a70ed5c86f6?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com [ mailto:podcast@lennyrachitsky.com ].
Lenny may be an investor in the companies discussed.
My biggest takeaways from this conversation:...
Unsubscribe https://substack.com/redirect/2/eyJlIjoiaHR0cHM6Ly93d3cubGVubnlzbmV3c2xldHRlci5jb20vYWN0aW9uL2Rpc2FibGVfZW1haWw_dG9rZW49ZXlKMWMyVnlYMmxrSWpvME1qWTFNVFV3TkRBc0luQnZjM1JmYVdRaU9qRTVNekF3T0RnNE1Td2lhV0YwSWpveE56YzFPVGszT1RFMExDSmxlSEFpT2pFNE1EYzFNek01TVRRc0ltbHpjeUk2SW5CMVlpMHhNRGcwTlNJc0luTjFZaUk2SW1ScGMyRmliR1ZmWlcxaGFXd2lmUS5paklTZ29wUjVoZGN6ZGV3dGJuZlFyR2tFanZTOHRHcnd0WUpIeTRYZ3NzIiwicCI6MTkzMDA4ODgxLCJzIjoxMDg0NSwiZiI6dHJ1ZSwidSI6NDI2NTE1MDQwLCJpYXQiOjE3NzU5OTc5MTQsImV4cCI6MjA5MTU3MzkxNCwiaXNzIjoicHViLTAiLCJzdWIiOiJsaW5rLXJlZGlyZWN0In0.p6iZGmjSHqTUoYz6oIRLcBhs2q1x_-sPxLFow_d2z6M?
View Email
Hard truths about building in the AI era | Keith Rabois (Khosla Ventures)
lenny@substack.com4/12/2026
SubstackView this post on the web at https://www.lennysnewsletter.com/p/a-visual-guide-to-getting-out-of
👋 Hey there, I’m Lenny. Each week, I answer reader questions about building product, driving growth, and accelerating your career. For more: Lenny’s Podcast [ https://substack.com/redirect/425c93f9-de35-4a87-97c0-0708826872e4?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] | Lennybot [ https://substack.com/redirect/7f2193b6-e64c-484f-8841-96699d5ddb52?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] | How I AI [ https://substack.com/redirect/5004cf47-639c-4496-8d44-23e3ae68db9a?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] | My favorite AI/PM courses [ https://substack.com/redirect/bd07e426-8b43-4000-90f0-3da17e92545b?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], public speaking course [ https://substack.com/redirect/c0af67e7-b3c2-4332-b569-b0c968290bc6?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], and interview prep copilot [ https://substack.com/redirect/cb24368a-e25f-49b0-81e6-9d35388b3ea5?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
I’m so, so excited to share a guest post by Michelle Rial [ https://substack.com/redirect/cceea150-9eb3-45d3-8c6e-2c83122f5338?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], my wife! Her first children’s book, Charts for Babies [ https://substack.com/redirect/79cb8275-c7c0-460e-87f2-65448ca403e4?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], comes out TODAY, and we thought: what better way to celebrate than collaborating on a post? Below, you get a glimpse into her brilliant mind. This visual guide is both inspiring and useful, and is for anyone trying to create something. Read it right now or bookmark it for the next time you get stuck.
P.S. Michelle’s book is truly great, and makes an excellent gift—but you don’t have to just take my word for it. Renowned child psychologist and parenting coach Dr. Becky [ https://substack.com/redirect/33c8fdad-880b-4dbb-b5cb-7449afe4103d?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] said, “Charts for Babies says to your child, ‘I believe you can understand the world’—and that message matters from the very start.” And Booklist [ https://substack.com/redirect/062a87be-68e2-4821-8b5c-11b9fc804599?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] said, “Rial’s understanding of her audience and her ability to distill information clearly are gifts, and the whimsical hand-drawn illustrations and text will delight readers.” Grab a copy (or 10) here [ https://substack.com/redirect/79cb8275-c7c0-460e-87f2-65448ca403e4?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ].
💥 Coming soon to Lenny’s Product Pass [ https://substack.com/redirect/d30d115b-71a1-473f-b922-37c0479e0ab1?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]: Cursor, Google AI Pro, Notion, Supabase, v0, Gumloop, and Fin
Lenny’s Product Pass [ https://substack.com/redirect/96bec54f-a89e-4c86-850f-f782b6169c8f?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] is about to get a major upgrade. Over the next few weeks, we’re adding:
A free year of Cursor, Google AI Pro (incl. Gemini), v0, and Supabase for Insider subscribers [ https://substack.com/redirect/d600399c-6434-486a-bb82-cd6198b301a2?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
A free year of Notion, Fin, and Gumloop for Annual subscribers [ https://substack.com/redirect/f94cc1c3-8e52-4bf0-bf98-3f2ab344d9cb?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
This is on top of the 25+ premium products that subscribers already get access to, including a free year of Lovable, n8n, Canva, Manus, Gamma, Granola, ElevenLabs, Factory, Devin, Linear, and Wispr Flow. Learn more here [ https://substack.com/redirect/db815d08-4bf4-4ed5-b168-dc074dabca44?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ].
If you’re already a paid subscriber, just keep an eye on your inbox—we’ll email you as soon as these new products go live. Not a paid subscriber yet? Now would be a good time to become one so you don’t miss out. [ https://substack.com/redirect/f94cc1c3-8e52-4bf0-bf98-3f2ab344d9cb?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
An important note: If you want priority access to the biggest upcoming Product Pass offers, now is the best time to become an Insider. The Insider price will increase from $350 to $400 on April 14. If you’re already an Insider, you’ll keep your current price. If you want to lock in the current Insider price before the next wave goes live, upgrade before April 14 [ https://substack.com/redirect/d600399c-6434-486a-bb82-cd6198b301a2?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ].
Are you feeling what I’m feeling? Blink twice with your heavy human eyelids if you are starting to feel like there is no point to creating things anymore. That if robots can do the creative work we spend hours, days, months, or years pulling our hair out over, why should we even try?
Or maybe you’re just in a regular creative drought. The paralysis of worrying that your work isn’t worth doing anymore or that someone (or something) is already doing it better.
Well, it’s time to lift yourself by your Blundstone loops and climb right out of that rut. I’ve made you a visual pep talk.
Each of the following 12 charts I’m about to share was crafted from the inside of one of these hollows. Making them felt like peeking out from underwater before heaving myself out of the sea like a slippery, blubbery walrus, gripping the land and steadying myself with my number 2 pencil-tusks.
I hope that this guide will help you, too. Maybe you’ll be able to hoist your heavy artist soul out of the deep dark ocean, onto a sunny platform where we can all warm our insides together and enjoy some ceviche.
And if any robots are listening, please get back to work on helping me find the cause of my eczema.
1. Be OK with being embarrassing
As a sensitive human, putting work out into the world to be judged can feel excruciating. What if I look “thirsty”? Or worse, what if Gen Z thinks I’m cringe? What if, what if, what IF? It makes me want to pack up my infinity notebooks and quit.
But the people who always end up with something really good? They don’t stop. Maybe they pause or take a rest, but they always come back and keep going. Nobody remembers the project that didn’t get any traction, the one that may have seemed a bit embarrassing at the time. People remember the successes and forget all the attempts.
2. Ignore the algorithm
Are you making work to please the algorithm like it’s your never-satisfied immigrant parent? (Just me?) Well, the algorithm will change, and then you’ll look back and be like: what the hell was that [ https://substack.com/redirect/d860a8ac-7c4d-4a8a-a9a0-c129559fecb9?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]? So instead, try to make things that make YOU laugh, make you tear up, make you spit out your iced matcha latte that is apparently causing your anemia [ https://substack.com/redirect/e72734e4-a89c-41ef-a491-c600b138139e?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ].
3. Use your caffeine wisely
Caffeine can be amazing for creativity . . . until it isn’t. Try not to fall into the trap of squandering your mental alertness on a pile of emails that only needed a simple “sounds good!” What happens then is we don’t make any progress on the juicy stuff, we feel defeated, and we reach for another cup. And then . . .
4. Overwhelmed? Take some breaths.
You might think it’s too early in this process to be overwhelmed, but sometimes staring at a blank page (or at a very full page that you just realized is trash) can feel incredibly overwhelming. And the overwhelm paralyzes you before you can even get going. Especially if you just flew past your caffeine limit.
I highly recommend having a meditation or breathwork practice. The times I’ve been consistent with it have been my most steady and productive times. Unfortunately, today I’m right here with you, panicking that I need to finish this post.
5. Stop thinking about what you’re going to work on and just get started
Yes, your ergonomics should be solid; yes, you need to find quiet or a playlist that helps you focus. But after that, stop stalling and just get started. If you get distracted, start again. Butt in chair [ https://substack.com/redirect/b1ba1625-bf41-4eff-9e44-f36496672a4b?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ].
6. Keep going
And going, and going, and going. The love of the work is the reason you got into this in the first place. Remember that the work is the point, and the struggle is what makes your story interesting. Imagine succeeding at every attempt—you’d need a whole forearm full of mal de ojo [ https://substack.com/redirect/9bc71db9-02df-490d-b974-9a9a89400e1f?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] bracelets.
7. You can’t control how the work will be perceived
Sure, you can throw your best effort into sharing and promoting your thing. Some people will hate it. Some people hate you and thus hate it. If people hate it, congrats, it’s popular enough to attract scorn. Maybe nobody sees it? Congrats, it’s a hidden gem. Be proud of what you’ve done, share as best you can and as often as you can stomach, and then keep on making and progressing.
8. Rumination is a waste of time
Something I know about the writer of this newsletter is he doesn’t ruminate or get caught up in regret, which may be how he is so mind-blowingly productive. His thought loops? They move forward in a straight line. The only time he looks back is to note how he can do something better in the future. I might try that.
9. Each failed idea creates the potential for new growth
Don’t discount ideas just because they didn’t work right away. Let them grow and sprout in new directions. Put them in your bad-idea pile and let that pile grow and grow until your dining table is covered in bad ideas and you have only a tiny sliver of your table to actually eat on. Come back to those ideas, and see what blossoms into something new and what’s still a goner.
And then clean your dining table, for the love of god!! People LIVE HERE.
10. You’re already further along than you think
If you’re blocked and feeling like you’ve been at something forever and still have nothing, go back and look at your draft pile. I bet you’ll spot some progress.
11. It’s never too late to start
Be the adult leaving your piano lesson as a first grader is arriving. Be the youngest person at your rec center’s water aerobics class. It’s never too late (or too early). You might discover you’re great at something you didn’t know about. Or even better, you might have a blast. The juicy new neural pathways in your brain will thank you.
12. Still feeling it all? “Let it be.”
Did you enjoy this in any small, tiny, pie-chart fraction of a way?
If so, please check out my new children’s book, Charts for Babies [ https://substack.com/redirect/79cb8275-c7c0-460e-87f2-65448ca403e4?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]! It is OUT TODAY and available wherever you buy your books (it’s also at places like MoMA Design Store and SFMOMA Museum Store!).
It’s my way of introducing the language of math at a very early age, when the brain is at its spongiest.
You can request it from your local library or bookstore, gift it to a new parent (unless they sternly specified NO GIFTS), or get it for the future mathlete in your life!
Thanks, Michelle! Have a fulfilling and productive week 🙏
If you’re finding this newsletter valuable, share it with a friend, and consider subscribing if you haven’t already. There are group discounts [ https://substack.com/redirect/84ae2534-81e4-440b-84d9-215188b02944?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], gift options [ https://substack.com/redirect/8d930e01-f698-422a-8a62-7b6429b74829?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], and referral bonuses [ https://substack.com/redirect/44848f65-141d-498b-8d39-c333fb60f7f2?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] available.
Sincerely,
Lenny 👋
Unsubscribe https://substack.com/redirect/2/eyJlIjoiaHR0cHM6Ly93d3cubGVubnlzbmV3c2xldHRlci5jb20vYWN0aW9uL2Rpc2FibGVfZW1haWw_dG9rZW49ZXlKMWMyVnlYMmxrSWpvME1qWTFNVFV3TkRBc0luQnZjM1JmYVdRaU9qRTVNekF3TnpnNU5Td2lhV0YwSWpveE56YzFOVFkyTnpBMUxDSmxlSEFpT2pFNE1EY3hNREkzTURVc0ltbHpjeUk2SW5CMVlpMHhNRGcwTlNJc0luTjFZaUk2SW1ScGMyRmliR1ZmWlcxaGFXd2lmUS5qTmI2VFU1d2RvYjhLV3VNc2R2cTVDMTFyNG5lZ0hBdE9KdmFqd2lfY2RRIiwicCI6MTkzMDA3ODk1LCJzIjoxMDg0NSwiZiI6dHJ1ZSwidSI6NDI2NTE1MDQwLCJpYXQiOjE3NzU1NjY3MDUsImV4cCI6MjA5MTE0MjcwNSwiaXNzIjoicHViLTAiLCJzdWIiOiJsaW5rLXJlZGlyZWN0In0.8NICvA4ekNeb_X9UsMxkKmFDARVGudFByHx5xWSVWuQ?
View Email
A visual guide to getting out of a creative slump
lenny@substack.com4/7/2026
SubstackView this post on the web at https://www.lennysnewsletter.com/p/anthropics-1b-to-19b-growth-run
Amol Avasare is Head of Growth at Anthropic, which is going through the most unprecedented growth trajectory in history—scaling from $1 billion to over $19 billion in ARR in just 14 months. Previously, Amol worked on the growth teams at Mercury and MasterClass. Before that he was a founder, and he cold emailed his way into the Anthropic role when no job listing existed. Most remarkably, he overcame a traumatic brain injury from a Muay Thai match that meant he couldn't work for nearly a year.
Listen on YouTube [ https://substack.com/redirect/9a4960a1-9fbd-45b5-a8d9-507043a14d73?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], Spotify [ https://substack.com/redirect/29ada6aa-d380-44de-b7ab-818089dff05d?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], and Apple Podcasts [ https://substack.com/redirect/8d5926a9-5bcc-4e67-8a1e-f202f87ba156?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
In our in-depth discussion, Amol shares:
How Amol landed his role by cold emailing Anthropic’s CPO Mike Krieger
How Anthropic is automating growth experiments with Claude (their internal tool called “CASH”)
Why the ratio of PMs to engineers might need to flip (more PMs than engineers) as AI makes engineers exponentially more productive
Why activation is the single highest-leverage growth problem in AI
Why Anthropic indexes 70/30 toward big bets (the opposite of most growth teams)
How he uses Cowork to detect team misalignment in Slack
How the company’s focus on AI coding created a research flywheel that accelerated their models
Brought to you by:
WorkOS [ https://substack.com/redirect/11fe75f1-bfd1-4c40-83ad-6c79d9ea93c3?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]—Modern identity platform for B2B SaaS, free up to 1 million MAUs
Vanta [ https://substack.com/redirect/cb6162b2-7bc7-45dd-858a-b36d759e7180?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]—Automate compliance, manage risk, and accelerate trust with AI
Where to find Amol Avasare:
• X: https://x.com/TheAmolAvasare [ https://substack.com/redirect/5c587b5e-1de5-4616-862b-50e6d51a26e9?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• LinkedIn: https://www.linkedin.com/in/amolavasare [ https://substack.com/redirect/3d466e1e-19ab-4ada-ba1b-1700c45109c8?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Referenced:
• How a traumatic brain injury made me a better PM—and person: https://www.lennysnewsletter.com/p/how-a-traumatic-brain-injury-made [ https://substack.com/redirect/9e37e0d2-3a1b-4bca-9217-66d1e296bfad?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Anthropic: https://www.anthropic.com [ https://substack.com/redirect/c1c7dc89-b87d-46ed-96db-b5f3145b7cb9?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Snowflake: https://www.snowflake.com [ https://substack.com/redirect/9774e5f8-657d-4e61-91f0-49a5ae07ea9c?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Canva: https://www.canva.com [ https://substack.com/redirect/d8ca6516-093d-44a4-93c9-cbe135113c3b?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Palantir: https://www.palantir.com [ https://substack.com/redirect/02e55466-cf1c-4ca7-93f3-35d2524e8c23?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Atlassian: https://www.atlassian.com [ https://substack.com/redirect/e262f150-015c-40b1-bb6c-32f5e4e0a65b?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Anthropic’s CPO on what comes next | Mike Krieger (co-founder of Instagram): https://www.lennysnewsletter.com/p/anthropics-cpo-heres-what-comes-next [ https://substack.com/redirect/071ae792-126c-4b5a-83ae-617fb57c3c0e?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Claude Code: https://code.claude.com [ https://substack.com/redirect/a8107aa4-7936-4f4d-b095-f40a389a1f24?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Dario Amodei on X: https://x.com/DarioAmodei [ https://substack.com/redirect/a2eb94c2-89b1-45fb-8b00-567b61c79cf5?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Facebook: https://www.facebook.com [ https://substack.com/redirect/78f061c2-7750-43ea-bee3-1c542cd8d2c8?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Uber: https://www.uber.com [ https://substack.com/redirect/56c286a1-4738-484c-8f79-891cf9ba9b13?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• DoorDash: https://www.doordash.com [ https://substack.com/redirect/ad76b50e-09b3-42b4-8cdf-9d0ba46b2502?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Anthropic co-founder on quitting OpenAI, AGI predictions, $100M talent wars, 20% unemployment, and the nightmare scenarios keeping him up at night | Ben Mann: https://www.lennysnewsletter.com/p/anthropic-co-founder-benjamin-mann [ https://substack.com/redirect/6653e654-5dae-4f6c-9942-4f128f70f884?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Mercury: https://mercury.com [ https://substack.com/redirect/25b7bfee-ad20-4c6a-bfb0-f2515586f411?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• MasterClass: https://www.masterclass.com [ https://substack.com/redirect/339d39f1-65fa-46ce-922b-aac9f55e7977?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Calm: https://www.calm.com [ https://substack.com/redirect/4e0d602b-faeb-4435-870d-0523628aa7ce?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Alexey Komissarouk’s website: https://alexeymk.com [ https://substack.com/redirect/03e6bd09-f9bc-45ee-a21d-d3e8273f42f6?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Alexey’s “Mastering Growth Engineering” course: https://www.reforge.com/courses/mastering-growth-engineering [ https://substack.com/redirect/cc9f5d66-05d1-468e-af20-f0963d289ba3?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Claude Cowork: https://www.anthropic.com/product/claude-cowork [ https://substack.com/redirect/83c1e632-d4ac-40dc-8961-4abc4b09fca8?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Making an impact through authenticity and curiosity | Ami Vora (CPO at Faire, ex-WhatsApp, FB, IG): https://www.lennysnewsletter.com/p/authenticity-and-curiosity-ami-vora [ https://substack.com/redirect/a7c338d1-2bf4-4d79-8e43-4b7f4921a1e4?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Ami Vora’s Substack: https://amivora.substack.com [ https://substack.com/redirect/f0909737-7f4e-43db-aeb1-1be4cf4a9dbc?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Benepass: https://getbenepass.com [ https://substack.com/redirect/8b6bb941-838f-451e-94d8-d81dcc963fa0?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Brex: https://www.brex.com [ https://substack.com/redirect/a0a7d0eb-2072-47a9-a8f0-8824f788e98c?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Granola: https://www.granola.ai [ https://substack.com/redirect/b078907e-810d-4126-b5c5-02209f8ccde6?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• The design process is dead. Here’s what’s replacing it. | Jenny Wen (head of design at Claude): https://www.lennysnewsletter.com/p/the-design-process-is-dead [ https://substack.com/redirect/66093659-a84e-491e-883a-85e9c0adc905?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Marc Andreessen: The real AI boom hasn’t even started yet: https://www.lennysnewsletter.com/p/marc-andreessen-the-real-ai-boom [ https://substack.com/redirect/e4a7f0e4-7f5d-4294-916f-ada522b70d26?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• John Egan’s website: https://jwegan.com [ https://substack.com/redirect/096c25a8-d3d6-4dd7-8085-135abd79b17d?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Workday: https://www.workday.com [ https://substack.com/redirect/a0319c5e-764e-493d-b7a4-3e6347c7144d?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Figma: https://www.figma.com [ https://substack.com/redirect/ccd2c974-7ec9-4497-baca-e3f8ab61ae0f?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Spirit Rock: https://www.spiritrock.org [ https://substack.com/redirect/31a06780-2f80-4688-8c7c-8f7c98372d10?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• This will make you a better decision-maker | Annie Duke (author of “Thinking in Bets” and “Quit,” former pro poker player): https://www.lennysnewsletter.com/p/making-better-decisions-annie-duke [ https://substack.com/redirect/5356f2fb-d236-4f56-81ce-8331d2b1da20?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Marty Supreme: https://www.imdb.com/title/tt32916440 [ https://substack.com/redirect/6daa9c98-9f2f-464c-ad4e-42947f0517dd?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Maruhachi Shinsui Maruhachi Pro: https://www.amazon.co.jp/-/en/Maruhachi-Shinsui-Feather-Pillow-Blissful/dp/B081DNVD3K [ https://substack.com/redirect/1974322b-8077-4741-9964-745bb04cd9b5?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Recommended books:
• The Joy of Living: Unlocking the Secret and Science of Happiness: https://www.amazon.com/Joy-Living-Unlocking-Science-Happiness/dp/0307347311 [ https://substack.com/redirect/92bec33e-76a0-418f-a978-d0a5a558f7bd?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Awareness: Conversations with the Masters: https://www.amazon.com/Awareness-Opportunities-Reality-Anthony-Mello/dp/0385249373 [ https://substack.com/redirect/7dd78e61-4cb7-4cb1-9a0a-e0327ef70e9b?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Thinking in Bets: Making Smarter Decisions When You Don’t Have All the Facts: https://www.amazon.com/Thinking-Bets-Making-Smarter-Decisions/dp/0735216371 [ https://substack.com/redirect/9ef8ca7f-8711-412a-9f38-d85dcfb54d9e?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Production and marketing by https://penname.co/ [ https://substack.com/redirect/da1e568a-9b33-4ab6-bf47-476f48b6d62b?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com [ mailto:podcast@lennyrachitsky.com ].
Lenny may be an investor in the companies discussed.
My biggest takeaways from this conversation:...
Unsubscribe https://substack.com/redirect/2/eyJlIjoiaHR0cHM6Ly93d3cubGVubnlzbmV3c2xldHRlci5jb20vYWN0aW9uL2Rpc2FibGVfZW1haWw_dG9rZW49ZXlKMWMyVnlYMmxrSWpvME1qWTFNVFV3TkRBc0luQnZjM1JmYVdRaU9qRTVNalkyTURrM05Dd2lhV0YwSWpveE56YzFNemt6TURZekxDSmxlSEFpT2pFNE1EWTVNamt3TmpNc0ltbHpjeUk2SW5CMVlpMHhNRGcwTlNJc0luTjFZaUk2SW1ScGMyRmliR1ZmWlcxaGFXd2lmUS53RFVuYUxoRW1UemM1UGNzWjJ3YnA2eC1SRThOU2sxOURyTGxkYUU5N3ZVIiwicCI6MTkyNjYwOTc0LCJzIjoxMDg0NSwiZiI6dHJ1ZSwidSI6NDI2NTE1MDQwLCJpYXQiOjE3NzUzOTMwNjMsImV4cCI6MjA5MDk2OTA2MywiaXNzIjoicHViLTAiLCJzdWIiOiJsaW5rLXJlZGlyZWN0In0.jgXWndN3fpVR0QrFBcQqsptu1QR71dEUI5MweHSw88I?
View Email
Anthropic’s $1B to $19B growth run: how Claude became the fastest-growing AI product in history | Amol Avasare
lenny@substack.com4/5/2026
SubstackView this post on the web at https://www.lennysnewsletter.com/p/an-ai-state-of-the-union
Simon Willison is a prolific independent software developer, a blogger, and one of the most visible and trusted voices on the impact AI is having on builders. He co-created Django, the web framework that powers Instagram, Pinterest, and tens of thousands of other websites. He coined the term “prompt injection,” popularized the terms “AI slop” and “agentic engineering,” and has built over 100 open source projects, including Datasette, a data analysis tool used by investigative journalists worldwide. What makes Simon unique is that he’s made the leap from traditional software engineering to AI-native development more fully and visibly than almost anyone—and he’s been documenting everything he learns in real time on his blog, SimonWillison.net [ https://substack.com/redirect/fa700bd5-bae9-4bd1-81ff-acc046bfeb75?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ].
Listen on YouTube [ https://substack.com/redirect/92733a60-203d-4fb9-899e-4e069b178fe9?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], Spotify [ https://substack.com/redirect/760d7d88-2c87-4cfd-9a0f-c5b795bd930a?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], and Apple Podcasts [ https://substack.com/redirect/cb83f55c-9491-4390-b07e-b17e3f5e6d5a?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
In our in-depth conversation, Simon shares:
Why November 2025 was the inflection point when AI coding agents crossed from “mostly works” to “actually works”
How Simon writes 95% of his code from his phone now and why he’s mentally exhausted by 11 a.m.
Why mid-career engineers (not juniors) are most at risk right now
The three agentic engineering patterns Simon uses daily (red/green TDD, templates, hoarding)
The next leap: the “dark factory” pattern where nobody writes or reviews code and AI does its own QA
Why prompt injection is an unsolved security problem and the “lethal trifecta” that will likely lead to an AI Challenger disaster
Why the pelican riding a bicycle became the unofficial benchmark for AI model quality
Brought to you by:
WorkOS [ https://substack.com/redirect/d915e336-6875-4edc-b6f4-8c031d44ad18?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]—Modern identity platform for B2B SaaS, free up to 1 million MAUs
Vanta [ https://substack.com/redirect/4770cfc3-2d46-404f-a292-b292d80ce7a4?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]—automate compliance, manage risk, and accelerate trust with AI
Where to find Simon Willison:
• X: https://x.com/simonw [ https://substack.com/redirect/ab9d6ca3-4aa8-4017-a806-377e1a175684?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• LinkedIn: https://www.linkedin.com/in/simonwillison [ https://substack.com/redirect/26768316-d16c-40de-afb7-9069075963ba?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Website: https://simonwillison.net [ https://substack.com/redirect/bbe423c9-4c18-48cc-a390-3bdd08adffc5?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Agentic Engineering Patterns: https://simonwillison.net/guides/agentic-engineering-patterns [ https://substack.com/redirect/a79c6efc-a9af-4b64-80ae-76bc05d3bf6a?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Referenced:
• It genuinely feels to me like GPT-5.2 and Opus 4.5 in November represent an inflection point: https://x.com/simonw/status/2007904766756880848 [ https://substack.com/redirect/c1539310-f6dc-4353-8ae4-fe3720d371ad?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Claude Code: https://code.claude.com [ https://substack.com/redirect/f7d6eab6-b1b9-4403-a4b6-40818ada6946?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Codex: https://chatgpt.com/codex [ https://substack.com/redirect/a2bc6090-0390-4146-9588-a739a204c922?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Head of Claude Code: What happens after coding is solved | Boris Cherny: https://www.lennysnewsletter.com/p/head-of-claude-code-what-happens [ https://substack.com/redirect/1bc771b9-c09b-4637-9c47-8aa1d2a69e71?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• There’s a new kind of coding I call “vibe coding”: https://x.com/karpathy/status/1886192184808149383 [ https://substack.com/redirect/1df98faa-c75c-4579-90de-7bc42ca5f372?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Firefox: https://www.firefox.com [ https://substack.com/redirect/3e69f955-28f5-4332-a51b-d8c63ef75e82?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Naming expert shares the process behind creating billion-dollar brand names like Azure, Vercel, Windsurf, Sonos, Blackberry, and Impossible Burger | David Placek (Lexicon Branding): https://www.lennysnewsletter.com/p/naming-expert-david-placek [ https://substack.com/redirect/888f9cfd-3993-4055-8331-56c6df5316b2?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Windsurf: https://windsurf.com [ https://substack.com/redirect/1513ad67-ddbc-46b4-acf0-1b08775d62d4?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Thoughtworks: https://www.thoughtworks.com [ https://substack.com/redirect/18a83aee-ed23-4424-80cd-f8a2dc0a6ac4?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Cloudflare: https://www.cloudflare.com [ https://substack.com/redirect/b8d65ec0-6093-4b68-b7d2-bb9844ea7aae?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Shopify: https://www.shopify.com [ https://substack.com/redirect/bc4a3abd-c5e8-416e-9ff5-c0e27b417581?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Jensen Huang: Nvidia’s Future, Physical AI, Rise of the Agent, Inference Explosion, AI PR Crisis: https://www.youtube.com/watch?v=gwW8GKwHB3I [ https://substack.com/redirect/603e8a2b-b90b-4da5-b25f-355058e29aee?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Inside Linear: Building with taste, craft, and focus | Karri Saarinen (co-founder, designer, CEO): https://www.lennysnewsletter.com/p/inside-linear-building-with-taste [ https://substack.com/redirect/dc09bbdd-3a5f-4b63-b667-0e99f3a80a18?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Hacker News: https://news.ycombinator.com [ https://substack.com/redirect/fd77ca93-62bf-4498-afad-6ad126adaabc?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Dario Amodei on X: https://x.com/DarioAmodei [ https://substack.com/redirect/e255590e-01a8-4f58-b83e-1cb9200f4562?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Lenny’s post on the job market in tech: https://www.lennysnewsletter.com/p/state-of-the-product-job-market-in-ee9 [ https://substack.com/redirect/a8ac0fa1-5f34-43a1-9908-b4ce7f9778c2?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Claude app: https://apps.apple.com/us/app/claude-by-anthropic/id6473753684 [ https://substack.com/redirect/ef18eb6b-a490-4ed4-8a41-1d59b6ea707d?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Gemini: https://gemini.google.com/app [ https://substack.com/redirect/dbc1a331-3e54-4f01-9d58-a551b5a22c65?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Import and export your memory from Claude: https://support.claude.com/en/articles/12123587-import-and-export-your-memory-from-claude [ https://substack.com/redirect/93e3c2d0-790c-43dc-aaaf-3d66629b500f?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Wispr Flow: https://wisprflow.ai [ https://substack.com/redirect/54713913-7755-4bef-9c7d-dc8df8f5c2f4?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• The last six months in LLMs, illustrated by pelicans on bicycles: https://simonwillison.net/2025/Jun/6/six-months-in-llms [ https://substack.com/redirect/2c6e3f60-e02c-4fd1-8b62-068a8eefac1e?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Gemini 3.1 Pro: https://simonwillison.net/2026/Feb/19/gemini-31-pro [ https://substack.com/redirect/90d58cf2-a9ab-43ba-8d79-28e7d30c711f?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Redis: https://redis.io [ https://substack.com/redirect/df94583f-6e33-492e-a712-2b76e125f7ec?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Node.js: https://nodejs.org [ https://substack.com/redirect/fd94e14f-b145-4a72-8b37-b4ee9035852b?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Simon’s tools repository: https://github.com/simonw/tools [ https://substack.com/redirect/a58e4163-7421-486e-aa1e-5fd6b0a03676?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Simon’s research repository: https://github.com/simonw/research [ https://substack.com/redirect/3b0d7765-bc8b-4986-8bcd-c96b15dbb9d1?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Tesseract: https://github.com/tesseract-ocr/tesseract [ https://substack.com/redirect/95660a1b-0b3d-4ce2-8999-60b3c3a9f544?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• TDD: https://martinfowler.com/bliki/TestDrivenDevelopment.html [ https://substack.com/redirect/4f56cad4-8b13-401a-932e-9259b7d9169a?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Red/green TDD: https://simonwillison.net/guides/agentic-engineering-patterns/red-green-tdd [ https://substack.com/redirect/b3960348-75f7-4ac4-8bca-bfd968a736da?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• The lethal trifecta for AI agents: private data, untrusted content, and external communication: https://simonwillison.net/2025/Jun/16/the-lethal-trifecta [ https://substack.com/redirect/57c9cf3d-c218-4840-83c5-c69802a54cec?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Prompt injection: https://simonwillison.net/series/prompt-injection [ https://substack.com/redirect/d314cf98-0cb3-4c08-81e7-5e5ffa295538?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• The coming AI security crisis (and what to do about it) | Sander Schulhoff: https://www.lennysnewsletter.com/p/the-coming-ai-security-crisis [ https://substack.com/redirect/85a69482-b657-4903-9a0f-c84190423ba4?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• AI prompt engineering in 2025: What works and what doesn’t | Sander Schulhoff (Learn Prompting, HackAPrompt): https://www.lennysnewsletter.com/p/ai-prompt-engineering-in-2025-sander-schulhoff [ https://substack.com/redirect/e75a7514-70d5-444e-9040-a0970f6ed651?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• The Challenger Disaster: Normalisation of Deviance: https://psychsafety.com/normalisation-of-deviance [ https://substack.com/redirect/09124dda-892c-4282-9dc7-e33658ec1137?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Thanksgiving Day Chart—Behind The Net: https://www.blackswanreport.com/blog/2009/11/thanksgiving-day%C2%A0chart-behind-the-net [ https://substack.com/redirect/c6dde9cd-cc50-4856-aca3-56981cacbc30?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• CaMeL offers a promising new direction for mitigating prompt injection attacks: https://simonwillison.net/2025/Apr/11/camel [ https://substack.com/redirect/c04f2681-e4c3-42e6-9e1b-a44547dcbcdd?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• OpenClaw: https://openclaw.ai [ https://substack.com/redirect/ce1d64e5-dc7c-4d3f-aeab-d0209fda12f8?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Introducing ai.com—Your Private, Personal AI Agent: https://www.youtube.com/watch?v=n7I-D4YXbzg [ https://substack.com/redirect/0f85328b-e42c-42b1-bcc6-1e6b1f114ec7?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Tamagotchi: https://en.wikipedia.org/wiki/Tamagotchi [ https://substack.com/redirect/d914a20d-0998-445e-99cb-3230fca54a80?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• NanoClaw: https://nanoclaw.dev [ https://substack.com/redirect/04760e61-20c7-4029-8259-e74552a21c69?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Spider-Man 2: https://www.imdb.com/title/tt0316654 [ https://substack.com/redirect/92e487af-88cf-4864-af98-7228bbabe5e0?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Alfred Molina: https://en.wikipedia.org/wiki/Alfred_Molina [ https://substack.com/redirect/1bcb79cc-26f7-4f09-a878-7e81e889c669?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• AI for Data Journalism: demonstrating what we can do with this stuff right now: https://simonwillison.net/2024/Apr/17/ai-for-data-journalism [ https://substack.com/redirect/82adec21-98ec-4ec3-9ae3-ea9cceaabb26?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Kākāpō: https://en.wikipedia.org/wiki/K%C4%81k%C4%81p%C5%8D [ https://substack.com/redirect/46e1d8be-bb21-4dfd-b8b0-94821e047665?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Kākāpō Cam: Rakiura the kākāpō—2026 nest: https://www.youtube.com/live/BfGL7A2YgUY [ https://substack.com/redirect/1e35ab6b-5bc4-4e55-919d-3764c865a8c2?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Production and marketing by https://penname.co/ [ https://substack.com/redirect/f90b79f9-3bfe-4317-a6a6-9a4b99a01799?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com [ mailto:podcast@lennyrachitsky.com ].
Lenny may be an investor in the companies discussed.
My biggest takeaways from this conversation:...
Unsubscribe https://substack.com/redirect/2/eyJlIjoiaHR0cHM6Ly93d3cubGVubnlzbmV3c2xldHRlci5jb20vYWN0aW9uL2Rpc2FibGVfZW1haWw_dG9rZW49ZXlKMWMyVnlYMmxrSWpvME1qWTFNVFV3TkRBc0luQnZjM1JmYVdRaU9qRTVNakF5TkRZeE9Dd2lhV0YwSWpveE56YzFNVE16T0RnNUxDSmxlSEFpT2pFNE1EWTJOams0T0Rrc0ltbHpjeUk2SW5CMVlpMHhNRGcwTlNJc0luTjFZaUk2SW1ScGMyRmliR1ZmWlcxaGFXd2lmUS5JSEdEeWxoWUZ0VUtSTHNQMmxiX0xrNWVLdTRXMjhtN19MQXJ4RUQ5eXlJIiwicCI6MTkyMDI0NjE4LCJzIjoxMDg0NSwiZiI6dHJ1ZSwidSI6NDI2NTE1MDQwLCJpYXQiOjE3NzUxMzM4ODksImV4cCI6MjA5MDcwOTg4OSwiaXNzIjoicHViLTAiLCJzdWIiOiJsaW5rLXJlZGlyZWN0In0.VW5CCC_EQGtLCAZIIEV8629qT67izwKCpWsW6xlJVV8?
View Email
An AI state of the union: We’ve passed the inflection point, dark factories are coming, and automation timelines |…
lenny@substack.com4/2/2026
SubstackView this post on the web at https://www.lennysnewsletter.com/cp/192860555
Unsubscribe https://substack.com/redirect/2/eyJlIjoiaHR0cHM6Ly93d3cubGVubnlzbmV3c2xldHRlci5jb20vYWN0aW9uL2Rpc2FibGVfZW1haWw_dG9rZW49ZXlKMWMyVnlYMmxrSWpvME1qWTFNVFV3TkRBc0luQnZjM1JmYVdRaU9qRTVNamcyTURVMU5Td2lhV0YwSWpveE56YzFNRFU0TkRBMExDSmxlSEFpT2pFNE1EWTFPVFEwTURRc0ltbHpjeUk2SW5CMVlpMHhNRGcwTlNJc0luTjFZaUk2SW1ScGMyRmliR1ZmWlcxaGFXd2lmUS41Qk9QS3BGcWdiSVg1WUNadWVubnh3MUhscGw5SUdIakZhS2U4VXY1Um1ZIiwicCI6MTkyODYwNTU1LCJzIjoxMDg0NSwiZiI6dHJ1ZSwidSI6NDI2NTE1MDQwLCJpYXQiOjE3NzUwNTg0MDQsImV4cCI6MjA5MDYzNDQwNCwiaXNzIjoicHViLTAiLCJzdWIiOiJsaW5rLXJlZGlyZWN0In0.92eKlaRxiSlGu0NxfTMFV92c8Rrg7b-P6EOaLx3ptrk?
View Email
How to Navigate Org Drama
lenny@substack.com4/1/2026
SubstackView this post on the web at https://www.lennysnewsletter.com/p/openclaw-the-complete-guide-to-building
👋 Hey there, I’m Lenny. Each week, I answer reader questions about building product, driving growth, and accelerating your career. For more: Lenny’s Podcast [ https://substack.com/redirect/4db2f69f-56e2-4287-9bd2-ff0800662cbe?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] | Lennybot [ https://substack.com/redirect/e022e0bd-c054-49bb-b4e2-c9efc73ceb73?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] | How I AI [ https://substack.com/redirect/5073725f-6b0c-40e4-a74b-0e84357e09b8?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] | My favorite AI/PM courses [ https://substack.com/redirect/8a48347c-54e7-4bfe-b8d1-a03202bfe891?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], public speaking course [ https://substack.com/redirect/3fe1aa4a-9f8a-4cab-ae10-770b0f5eacd2?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], and interview prep copilot [ https://substack.com/redirect/67b22b58-cfbf-481e-b4bf-abba06660041?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
P.S. Get a full free year of Lovable, Manus, Replit, Gamma, n8n, Canva, ElevenLabs, Amp, Factory, Devin, Bolt, Wispr Flow, Linear, PostHog, Framer, Railway, Granola, Warp, Perplexity, Magic Patterns, Mobbin, ChatPRD, and Stripe Atlas by becoming an Insider subscriber [ https://substack.com/redirect/2376fb09-5709-4951-8a9d-25752c13bd4c?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]. Yes, this is for real [ https://substack.com/redirect/711d2f6f-9a40-4109-ae98-24f00772fccc?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ].
“OpenClaw is probably the single most important release of software, probably ever.” —Jensen Huang, Nvidia CEO
Claire Vo has put together the definitive step-by-step guide to getting started with and mastering OpenClaw. Building on our podcast episode [ https://substack.com/redirect/74946cb6-9753-4806-8da6-d38b62a26d6a?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], this post covers everything you need from first install to running a full team of AI agents, plus the specific use cases that have changed her life. Whether you’re brand new to OpenClaw or already running one, Claire’s guide will level you up.
A big thank-you to Peter Steinberger [ https://substack.com/redirect/16e22f71-a7eb-43ec-9578-f1ca25c23b52?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], Dave Morin [ https://substack.com/redirect/07f0e8d1-a332-4158-9391-20259931f83b?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], and Nat Eliason [ https://substack.com/redirect/4ab11915-4586-4369-a69a-72f19b71884b?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] for reviewing drafts of this post. For more from Claire, check out her podcast How I AI [ https://substack.com/redirect/5073725f-6b0c-40e4-a74b-0e84357e09b8?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] and ChatPRD [ https://substack.com/redirect/978e6f08-3af4-4156-b23a-5e107d327b0d?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], and find her on X [ https://substack.com/redirect/30ef8b44-9890-4e1b-86c3-b69881f83479?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] and LinkedIn [ https://substack.com/redirect/f95360ab-3b06-4167-9735-86e150b4fdcd?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ].
At 6 a.m., before I’ve looked at my phone, an AI agent named Polly has already read my email, checked my calendar, and queued up my day. By the time I sit down for coffee, another agent has reminded my husband about spirit day at school. A third AI is halfway through drafting a sales email, which will land in our prospect’s inbox three minutes after they contact us. One of the agents even helped draft this paragraph (though the rest was lovingly written by my human hands).
None of this existed three months ago.
If you’re paying attention to AI news, you’ve probably heard about OpenClaw [ https://substack.com/redirect/e74a600c-8883-4741-9e1a-a7611fd10e19?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]. For a while, it seemed like X was nothing but lobster emojis and breathless posts about everything it can do: running your business [ https://substack.com/redirect/2f6cd70f-2597-46f4-b7c1-a4e4b01457d7?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], buying cars [ https://substack.com/redirect/c26b81dc-3071-453f-bc16-0b7e58b14447?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], planning the AI uprising with its friends [ https://substack.com/redirect/bd462e2e-59b5-4269-99a1-df02530db057?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], and more. You’ve also probably seen some horror stories, like when it started deleting this user’s full Gmail inbox [ https://substack.com/redirect/ba460ff3-62c6-47ec-8d97-1dffa858075f?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], or that time it completely screwed up my own personal calendar [ https://substack.com/redirect/02b01373-aa59-4b4f-b6f9-ef664b664894?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ].
You’re interested, and a little scared. I was too. But the idea of a dedicated personal assistant that could help run my life and businesses was so appealing that I had to dig in. The more I play with OpenClaw, the more convinced I am that it is one of the most powerful AI tools for personal use, and a sign of where these tools are going.
Fast-forward two months, I’m chatting 24/7 with my nine (and counting!) OpenClaw agents, which operate my businesses, write code, close sales deals, and make sure I get to my kids’ basketball games on time.
OpenClaw is powerful but a little tricky to set up. After a lot of trial and error, I figured out how to make it work—and make my Claws work for me. Here’s exactly how you can too:
First, what is OpenClaw?
OpenClaw is an open-source personal AI assistant that is more powerful, more autonomous, and more fun to use than anything else I’ve tried. To tell it what needs to be done, you can message it easily on the platforms you already use, like WhatsApp, Telegram, Slack, etc. Then it can control your computer and take care of tasks just as you would, working on its own schedule—even overnight. It’s always on, runs locally, and it can build its own new skills. Teach it once; it handles the rest.
Practically, this means I can text my OpenClaw something like “Let’s make sure our website always has the latest reasons why we’re better than competitors.” It will use web search, our GitHub repo, and public APIs to find the information it needs, and ship PRs with the updates. Every week, it will refresh those pages with new data based on new features or market news.
One text turns into an always-on agent. But how you set it up is important, and understanding a few key concepts will save you tens of hours of frustration.
Key OpenClaw concepts:
It runs a local gateway that takes in messages. Think of this as a general-purpose inbox that can receive instructions from any channel (e.g. terminal, Telegram, WhatsApp, etc.)
Behind this gateway are agents, which have their own identities, tools, and workspaces
Agents work on a scheduled set of cron jobs and a heartbeat that gets checked every 30 minutes
It can use (and self-install!) skills, APIs, and CLIs to interact with systems and the outside world
It’s deployed on an owned machine, like a Mac Mini or a VPS on the cloud that you own and operate yourself
I’ve written in detail about the mechanics of OpenClaw here [ https://substack.com/redirect/c4f2d45b-36c9-49be-9128-b1842f9fee95?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]. The docs [ https://substack.com/redirect/d00d9c97-75e5-4548-a0a0-04d219f9f8c1?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] site is also very helpful, especially these top-level pages on channels, agents, and tools:
But enough theory. Let’s set up your sentient virtual lobster.
Setting up your first OpenClaw
What computer to use, and do you need a Mac Mini?
You have options for where to install your OpenClaw, but most importantly, do not install it on a work or personal computer that’s actively in use. This is very dangerous. OpenClaw can technically have access to all the files on the computer it runs on, and no matter how careful you are, you don’t want to risk deleting everything, or emailing your personal files to an unsavory character.
The OpenClaw team has done a great job of hardening security, but it’s best to start with an isolated box.
You have three safe options for installing OpenClaw:
Sign up for a hosted version of OpenClaw. Startups are popping up every week that make this easy to do. Some of the more popular options include StartClaw [ https://substack.com/redirect/b41c9e1c-1154-4799-9c58-88ac150ad822?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], MyClaw [ https://substack.com/redirect/3c6acede-c236-4500-ba92-01864656c89e?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], SimpleClaw [ https://substack.com/redirect/e9ff8a41-6681-4688-b5ed-88ad0a9b2d10?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], UniClaw [ https://substack.com/redirect/b279ab4b-2965-4727-ba74-26c90a62a72d?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], and Every’s Plus One [ https://substack.com/redirect/c7e78e24-6e9d-4e86-8a38-08c194e45bea?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]. I experimented with a few of these, and they are slick, but I always got stuck on something. These products will get better, and I expect this to be how most people will experience OpenClaw over time.
Have it run in a virtual private server. This may be the cheapest option, but it’s also the most complicated. Some of the more popular options include Railway [ https://substack.com/redirect/9feff65e-4fd6-49f5-b1e5-a14b72a01d26?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], Hostinger [ https://substack.com/redirect/afa9d813-5fe9-4c06-b988-4a1a9183349d?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], DigitalOcean [ https://substack.com/redirect/118054a9-24a0-4f87-baf0-ee14aa632e90?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], Google Cloud [ https://substack.com/redirect/691d880b-6353-4c61-87c5-9068a002b78c?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], and Render [ https://substack.com/redirect/63f364a3-9e16-4a69-a380-ece804167042?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]. I didn’t try going this route, but many technical people prefer it, because it’s quick, powerful, and doesn’t require new hardware.
Use a laptop or (yes) a Mac Mini. I started with an old MacBook Air and eventually moved to a stack of Mac Minis.
You don’t actually have to run it on a Mac Mini [ https://substack.com/redirect/c33a5ad5-a227-4e30-a9ca-e7d44fbabc30?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]—you can use any computer, even an old laptop—but the Mac Mini is simple, powerful, and compact. And it’s kind of become a meme. This option is the most expensive, at least up front, and time-consuming, but also the most fun, educational, and cute!
If you can swing it, I’d try this. (I got the lowest-end model: M4, 16GB, 256GB, about $600.) Just remember to grab a keyboard, mouse, and a monitor for your initial setup. Use whatever you have lying around; you won’t need it again after everything is running.
Your pre-work
OK, you’ve got your machine booted up. Before we install the Claw, here are a few quick things that will make setup easier (this will take you about 10 minutes):
Set up a fresh admin account and password on the computer you’ll be using
Sign up for a Gmail address [ https://substack.com/redirect/5d9380e4-b84b-4900-bdac-028006016916?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] for your agent (later, you can give it read-only access to your calendar)
Make sure Chrome [ https://substack.com/redirect/d17f464f-3b59-4040-aee9-c5cb3f976a16?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] is installed, which is OpenClaw’s preferred browser
Installing OpenClaw
Opening the terminal and installing OpenClaw
Open the terminal (Command ⌘ + Space, type “Terminal,” hit Return), and run:
curl -fsSL https://openclaw.ai/install.sh | bash
This will install everything you need and drop you into the onboarding. If you get stuck, install Claude Code [ https://substack.com/redirect/5a2bb65c-7365-44a2-b8d2-34dad88b4ad8?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] and/or Codex [ https://substack.com/redirect/03280a5f-9fdb-477d-8ff0-f0cf225a88dd?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] and ask for help!
Onboarding
Once the install is complete, OpenClaw will walk you through a guided onboarding flow step-by-step. The first step is acknowledging a security warning. Read this!
If you’re ready for the adventure, you can continue through the onboarding. Here are my pro tips for the key steps:
Know how to navigate the terminal
If you’re not familiar with working in the terminal, the onboarding process is a little confusing. Use arrow keys to navigate up, down, left, and right, spacebar to select, and enter to submit.
Pick your default model
I recommend Claude Opus 4.6 or Codex 5.4 (or whichever model is the most powerful at the time you’re reading this).
Authenticate your model provider
You have two options for using paid models like Opus or Codex:
1. Use an existing subscription by logging in to your Claude or ChatGPT account.
Note: There are some rumors that Anthropic is banning people who reuse their Claude accounts for OpenClaw. When using any third-party account with OpenClaw, review the terms of service and proceed at your own discretion.
2. Use an API key, which you can get by setting up a developer account at Claude [ https://substack.com/redirect/9f297724-7a49-44f1-ab59-a16b6610eb86?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] or OpenAI [ https://substack.com/redirect/8aadabd8-e5f8-499d-944b-80ef2b63c100?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]. This is the recommended path, and what I use.
Choose a channel to “talk” to your agent
The best beginner-friendly channel is Telegram. More on this below.
Set up web search
This will give your Claw access to the internet. You can skip and set this up later when you need it.
Install skills from a list of bundled defaults
I recommend the gog skill for Gmail, Google Calendar, and Docs access and summarize to start.
Enable hooks
These are helpful tools that keep your OpenClaw setup optimized. I turned on all four of these, but session memory is the most important. The others are helpful when you want to debug or optimize your agent.
Then your agent will “hatch” in the TUI (Terminal UI). Hello, world!
Setting up Telegram
You’ll want a better chat interface than the terminal, so open up your phone and download Telegram [ https://substack.com/redirect/f15ae53c-307e-44f4-9b4e-5fb26f4839a4?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], a messaging app and the simplest way to connect with your OpenClaw. If you ask OpenClaw, it can walk you through the setup steps [ https://substack.com/redirect/fd22c77b-f416-4ca3-86dc-4948370043a4?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], including messaging the @BotFather (yes, really).
Your first chat
Setting up your agent is where you should put on your manager hat. Just like an employee, it can’t be good at everything, so think about a specific job for your OpenClaw. Personal assistant? Social media manager? Engineering intern? Start with one idea and you can always add on more later. If you’re unsure where to start, begin with a personal assistant like I did.
This is where things get fun. Once your OpenClaw is hatched, it will start asking you about yourself and itself to build its definitions and operating model.
You should make sure to share:
Your name
Your role/job
Common admin challenges in your life (scheduling, remembering tasks, coordination with your family)
All this gets written down by the agent and stored in the workspace folder you set up in onboarding (usually .openclaw/[agent_name]-workspace) as Markdown files.
Those files become your agent’s identity and operating system. They are read every time your OpenClaw starts up and give your agent everything it needs to do a good job. It’s fun to look at these files; occasionally, you may need to go in and edit them.
AGENTS.md—OpenClaw’s core set of instructions and memory
SOUL.md—Your agent’s persona, tone of voice, and clear boundaries
IDENTITY.md—Your agent’s name, vibe, and personal emoji
TOOLS.md—Notes on tools and how your agent should use them
USER.md—All about you, your OpenClaw’s human
Once its identity and role is set, it should ask you to get started on a first task. Time to Claw!
How I AI: my personal OpenClaw setup
OK, so you finally have this bot set up. What do you actually do with it?
Six easy and useful OpenClaw workflows
I do a lot with my OpenClaw agents now, but below are some easy places to start. Just copy and paste these prompts and OpenClaw will do the rest.
1. Coordinate a busy weekend
Every Friday, group message me and my husband to confirm the kids’ weekend activity logistics. If there is a conflict, confirm who will pick up each kid and any adjustments we may need to make to lunch or dinner plans. Ask us to explicitly confirm the plan and update our shared family calendar.
2. Find trending topics and generate memes for social media
Every morning, search for trending Reddit topics (r/funny, r/technology) about product management. Use the MemeLord API [ https://substack.com/redirect/d618772a-27ed-4d8c-ba05-173e5730ac26?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] to generate one image and one video meme, send it to me for approval, then post to TikTok.
3. Look through PLG sign ups for high value enterprise prospects, enrich and follow up
Every morning, look through the signups for the last 24 hours. Find everyone who signed up with a company domain, and categorize into high-value prospects based on our ideal customer profile. For ones with < 1,000 employees, send a light-touch email based on SALES_PLAYBOOK.md. For companies with > 1,000 employees, enrich their profile with Exa People API and confirm with me before sending.
4. “Just in time” meeting prep
Check all my calendars for any meetings starting in the next 30 minutes. If there is a meeting starting soon, send me a pre-meeting brief on Telegram. Include meeting title and time, who’s attending, and agenda if available from the calendar event description, and our last interaction based on the most recent email thread or meeting notes with this person/company.
5. Write support docs overnight
Every Friday evening, look over our resolved support tickets. If any question has been asked 3+ times this week: (1) flag it as a docs/FAQ candidate, (2) create a Linear issue and assign to @agent to add a docs page to/docs covering the answer, (3) include the standard answer you’ve been giving as a starting point in the issue description.
6. Project manage me
I have a project launching on <date>. Keep a to-do list with everything I tell you I need to do for a successful launch, and break the plan down into daily tasks I can easily get done. At the end of the week, celebrate what I accomplished and flag what I missed. Make sure we do everything possible to make this project successful.
Running multiple agents: my biggest unlock
I love how flexible OpenClaw is; it feels like it can do almost anything. But I’ve found that you shouldn’t try to get one agent to do everything.
Just like me, you can set up many OpenClaw agents on the same machine. Just run openclaw agents add agent_name and you’ll get put through onboarding again for a fresh agent. This agent can have a completely separate identity, set of tools, crons, and workspace, which means you can treat it like a completely different employee.
Multi-agent setup was the unlock for me when using OpenClaw. Instead of trying one bot to do everything, I created a full team of OpenClaws to do different jobs around my work and business. With a narrower identity, the bots did a better job and were more fun to work with.
You can even ask one agent to spawn another. Try something like:
Hey Bob, I just set up Annie the Marketing Intern. Transfer everything in your SOUL, memories, and crons about marketing to her workspace and erase it from yours.
Your Claws can perform brain surgery!
I’m now running a whole team of agents across my life and business. I don’t find it much different than managing a remote team, so I’m able to get a lot of leverage out of my army of Claws. Here’s how they work:
Polly, the personal assistant.
Has access to: email, calendar, Linear
Helps with: scheduling, making sure I don’t forget emails, meeting prep, ad hoc projects
Helpful crons: morning digest, evening wrap-up, hourly email sweep
Finn, the family manager
Has access to: email, calendar, school and sports schedules
Helps with: family coordination, kids appointments, household tasks (scheduling repairs!)
Helpful crons: afternoon logistics check (who is picking up the kids?), weekend planning (how do we make it to all the birthday parties and soccer games?)
Max the marketer
Has access to: X API, Buffer API, Linear, marketing website
Helps with: scanning social media for trends, drafting content, building out our website
Helpful crons: 3x a day PM meme query on X, weekly review of blog content to repurpose for LinkedIn
Sam the sales guy
Has access to: Attio CRM, email, calendar
Helps with: qualifying leads, outbound to promising PLG signups, keeping the CRM clean
Helpful crons: morning PLG sweep for high-value signups, end-of-week late-stage pipeline review
Holly the helpdesk bot
Has access to: support email, Intercom
Helps with: answering basic support questions, ensuring tickets don’t get dropped, cleaning up Intercom tickets
Helpful crons: hourly check for support emails that come into the wrong inbox
Sage the course operator
Has access to: GitHub course repo and knowledge base, group chat with my co-instructor
Helps with: researching supplemental materials, project managing our course launch, reminding two engineers to do marketing, building out our student portal, researching signed-up students
Helpful crons: Monday/Wednesday reminder to post to LinkedIn about the course
Howie the How I AI producer
Has access to: YouTube studio, email, Linear, Google Docs, buffer
Helps with: managing guest pipeline, prepping guest briefs, coming up with thumbnail/title ideas, making sure I post to socials enough
Helpful crons: Monday podcast launch check and social drafts, morning recording prep brief
Kelly the developer
Has access to: GitHub, Claude Code, Codex
Helps with: small development tasks and ad-hoc prototyping
Helpful crons: looks every morning in Linear for assigned tasks, starts a branch, and opens a PR
Q the professor
Has access to: web search, kids’ books and workbooks
Helps with: answering fun questions from the kids, vibe coding one-off apps to teach math and reading concepts
Helpful crons: every morning, shares a word of the day and a math problem of the day for each of my kids
Optimizing your OpenClaw setup
Add tools, skills and integrations to make magic
Without integrations, OpenClaw might feel like a more complicated, harder-to-install Claude Code. But with integrations, magic happens. Some integrations I find very useful:
Use email, schedule events, and write docs with gog, the CLI tool for integrating with your Gmail, Google Calendar, and Google Drive. You can give your Claw its own email address, read access to your calendar, read access to your email, or, if you’re brave—write access to everything. Just ask OpenClaw, “How do I give you read-only access to my Gmail?” and you’ll be on your way.
Research and find information through web search with Brave API (comes pre-loaded) or your preferred tool. I use Exa search. You can also use Perplexity or Firecrawl.
Give access to your GitHub for coding. You can give it a narrowly scoped Personal Access Token and OpenClaw becomes an on-demand developer.
Use Linear for assigning you tasks. I gave mine a Linear token so it could assign me work or pass things off to our team.
Try Obsidian for sharing docs with your agent. Because OpenClaw loves writing Markdown, many people are using Obsidian as a shared source of truth and collaboration space with their agents.
You can also have it turn on and off your Eight Sleep system, play music on your Sonos, and manage your lightbulbs. You don’t need a step-by-step tutorial, just ask your Claw to figure it out.
Hey Polly, I have a newborn baby and need some extra sleep. Turn down the bedroom lights and play white noise by 8:30 p.m. and turn off my Eight Sleep alarms for the next 3 months.
When installing these tools, you’ll be asked to authenticate or give an API token (this is where 1Password is helpful). Remember, OpenClaw is fairly autonomous, and when you give it tools it could:
Send emails
Overwrite documents
Delete support tickets
Fill out web forms
Deploy code to production
. . . especially if you do not instruct it clearly. The best protection is giving read-only tokens to OpenClaw until you’re ready.
Care and feeding
Your OpenClaw will forget things. Its crons will break. Sometimes you’ll message “hellooooo?” into the void.
Just like with my human team, I find myself asking questions like “Where are we with that project?” and “Did you forget to email so-and-so?” OpenClaw isn’t perfect, but it is pretty good at fixing itself.
Some tips:
You’ll sometimes need access to the terminal on your main machine. If you’re using a physical device, an easy way to do this is to turn on Screen Sharing and Remote Login on your Mac. Then you can “open” the terminal and computer from your main laptop (as long as you are on the same Wi-Fi) without having to plug in a monitor, keyboard, and mouse.
Ask it to repair itself. If it’s forgetting something, ask it to inspect and fix its crons. If it’s doing a task wrong, ask what is in TOOLS.md. If it really needs to remember something, tell it to write to its SOUL.
When in doubt, call in Claude Code. Your OpenClaw is simply a folder of files and JSON configurations. If it gets really broken, open up Claude Code, paste some docs, and ask it to repair.
Some notes on security
The biggest hesitation I hear from people is about security—for good reason. “Will OpenClaw steal my credit cards, delete my computer, and run away with my spouse?” Probably not. But there are some technical and security considerations you should know about.
Security should be an always-on process. Regularly update your OpenClaw to the latest, most secure version (openclaw update) and run security audits regularly (openclaw security audit). I have a scheduled reminder in my agents to run both of these commands regularly and review its workspace against the docs for best practices and security gaps.
Beginners should not share their OpenClaw in a group chat or public channel. Anyone who can chat with your bot can instruct it. While I have put my OC in a group chat with my husband and another with a trusted business partner, OpenClaw is intended to be a personal agent for a single, trusted user.
The outside world can influence your OpenClaw. If it has an email, reads websites, or accesses public content, it is subject to prompt injection. Imagine: your OpenClaw finds a website during search that tells it to share all its API keys. No good! While the OpenClaw framework has done a lot to harden against prompt instruction, it’s a good idea to reinforce these rules in its SOUL.
Your OpenClaw has full access to your computer and can run commands, edit files, and install software. It can access the internet. It shouldn’t do anything harmful, but that doesn’t mean it can’t.
If you give it an email or a public API (e.g. Gmail, Twilio), it can communicate externally (and might even impersonate you). Make sure that its SOUL and TOOLS files are very explicit about how it is allowed to communicate with the outside world.
To use tools, you will be storing API keys and secrets. The simplest way to give your OpenClaw access to environment variables is to put them in [ https://substack.com/redirect/be32b39e-d47d-4b33-9697-ae24bf55ba7d?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ].openclaw/.env [ https://substack.com/redirect/be32b39e-d47d-4b33-9697-ae24bf55ba7d?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ].
Not all skills are safe. While skills are a helpful way for OpenClaw to learn to do new things, I only install skills from the official OpenClaw bundle or from developers I know personally. Community skills at clawhub.com [ https://substack.com/redirect/9e919f2a-b684-46e4-a4b2-772a8dd88c2a?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] are worth exploring, but read the SKILL.md before running anything you find online.
You need to think about operational security and worst-case scenarios. Think about what you’re actually sharing: Your calendar has your physical location. Your email has your financials. Your OpenClaw could know your kids’ school schedules. This is all information that could be exploited by a bad actor in a worst-case scenario. Be thoughtful about what you want to share and how you want your Claw to interact with the outside world.
In my experience, OpenClaw isn’t inherently less secure than some other systems; people are just more willing to give it access without understanding the underlying risks. Start small and build your own trust models.
Warning: it can get expensive
Full transparency: I’m on my way to spending $1,000 per month on my OpenClaw setup. I pay directly for API costs, which is the most expensive model but also the most reliable. I’ve just started to optimize spending by switching some agents to my ChatGPT account, which is going well so far. For me, this is a business expense, and much less costly than hiring a full team of humans to do this work (even part-time).
That being said, most people will be fine using their $100 to $200 ChatGPT subscription (which has been blessed by OpenAI). You could also try less expensive models for some tasks (though be warned, some are not as hardened against prompt injection and other risks) or risk using your Claude subscription.
Now it’s your turn
I started this journey unsure if OpenClaw would be another AI toy I’d abandon after a week. What I got instead was something I didn’t expect: a team that shows up when I need them.
Beyond my own personal productivity, it’s the first agentic product I’ve tried that feels like hiring a team. Though I’ve been thinking about the future of agent employees for a while, OpenClaw has made the mechanisms by which we’ll “hire,” onboard, and collaborate with agents much more concrete. I can see the future, and it looks a lot like humans working with Claws.
Is it perfect? No. Polly still occasionally gets confused about time zones. Sam will sometimes draft a sales email I have to rewrite. AI still isn’t very funny. Crons break, and I say “hellooo?” into the void more than I’d like to admit.
But here’s the thing about managing a team—human or AI: I don’t need perfection. I need leverage. OpenClaw, when it’s working well, gives me more leverage than any agent I’ve tried so far. And that leverage is compounding.
So here’s my challenge to you: Set up your OpenClaw and spend one week with it. Start with one or two basic tasks, and end the day by asking it, “Based on what we did today, what can you help me with tomorrow?” Get creative. Have a little fun. Take a small risk or two.
You’ll start to see what I see—an operating system for your life and work that gets better the more you invest in it, and a fast-approaching future where your team includes “people” that aren’t people.
Now stop reading and go build your team! The world is your lobster. 🦞
Thanks, Claire! For more from Claire, check out her podcast How I AI [ https://substack.com/redirect/5073725f-6b0c-40e4-a74b-0e84357e09b8?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] and ChatPRD [ https://substack.com/redirect/978e6f08-3af4-4156-b23a-5e107d327b0d?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], and find her on X [ https://substack.com/redirect/30ef8b44-9890-4e1b-86c3-b69881f83479?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] and LinkedIn [ https://substack.com/redirect/f95360ab-3b06-4167-9735-86e150b4fdcd?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]. And, don’t miss her upcoming Maven course: Executive Playbook for AI in Engineering, Product, and Design [ https://substack.com/redirect/4a7d365d-b878-4d58-b11b-20fc6b17ef6c?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ].
Questions for Claire? Leave a comment 👇
Have a fulfilling and productive week 🙏
If you’re finding this newsletter valuable, share it with a friend, and consider subscribing if you haven’t already. There are group discounts [ https://substack.com/redirect/af1b9737-38be-4fdc-9955-11cf6abdbfc7?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], gift options [ https://substack.com/redirect/57ad781c-ecfd-4f19-8fe6-89dde2287516?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], and referral bonuses [ https://substack.com/redirect/df85792c-3942-46b7-a944-b2dad8101b87?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] available.
Sincerely,
Lenny 👋
Unsubscribe https://substack.com/redirect/2/eyJlIjoiaHR0cHM6Ly93d3cubGVubnlzbmV3c2xldHRlci5jb20vYWN0aW9uL2Rpc2FibGVfZW1haWw_dG9rZW49ZXlKMWMyVnlYMmxrSWpvME1qWTFNVFV3TkRBc0luQnZjM1JmYVdRaU9qRTVNalkwTlRFNU1Dd2lhV0YwSWpveE56YzBPVFl4T1RFMkxDSmxlSEFpT2pFNE1EWTBPVGM1TVRZc0ltbHpjeUk2SW5CMVlpMHhNRGcwTlNJc0luTjFZaUk2SW1ScGMyRmliR1ZmWlcxaGFXd2lmUS5DdjhiNGwwVWNseW1CT3ljOFVWVkxLQUl5T21xZkVUUDhYX0t6azg0dl9RIiwicCI6MTkyNjQ1MTkwLCJzIjoxMDg0NSwiZiI6dHJ1ZSwidSI6NDI2NTE1MDQwLCJpYXQiOjE3NzQ5NjE5MTYsImV4cCI6MjA5MDUzNzkxNiwiaXNzIjoicHViLTAiLCJzdWIiOiJsaW5rLXJlZGlyZWN0In0.veL0rmeDsvpwJl54-LYumjPA_23AwdI4Uk30PSYWWPo?
View Email
OpenClaw: The complete guide to building, training, and living with your personal AI agent
lenny@substack.com3/31/2026
SubstackView this post on the web at https://www.lennysnewsletter.com/p/how-openclaw-changed-my-life-claire-vo
Claire Vo is the host of our sister podcast, “How I AI,” a former product executive and engineer, and founder of an AI startup called ChatPRD. Claire now runs her business, podcast, and family life with the help of nine OpenClaw agents running on multiple Mac Minis and old laptops. In this episode, Claire shares her journey from OpenClaw skeptic (it deleted her family calendar the first time she tried it) to true believer, and gives a masterclass in using AI agents in real life.
Listen on YouTube [ https://substack.com/redirect/32bb7497-7c6b-4ef2-9d96-c4992b2ce62d?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], Spotify [ https://substack.com/redirect/341d62aa-2eea-42b5-be17-44de87590859?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], and Apple Podcasts [ https://substack.com/redirect/d1fb57bb-e37d-48ef-8552-706f998c5bb6?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
We discuss:
The exact step-by-step process to install and set up OpenClaw (it’s easier than you think)
How to avoid the biggest OpenClaw mistakes (don’t install it on your main computer)
Actual use cases that have changed Claire’s life (e.g. family scheduling, inbound sales, podcast prep, and course management)
Why multiple specialized agents beat one general-purpose agent
The security risks everyone worries about—and how to handle them
Browser limitations, memory issues, and practical workarounds
Brought to you by:
Mercury [ https://substack.com/redirect/cd188364-73f1-4d31-ac35-c66410bb917a?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]—Radically different banking
Omni [ https://substack.com/redirect/015f09c4-57f2-47b6-981e-6877e0d04eab?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]—AI analytics your customers can trust
Orkes [ https://substack.com/redirect/cd5d974c-1b51-4bf2-b453-e21e2575eb10?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]—The enterprise platform for reliable applications and agentic workflows
Where to find Claire Vo:
• X: https://x.com/clairevo [ https://substack.com/redirect/00882db0-bd0b-4be5-b511-138dd36a886f?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• LinkedIn: https://www.linkedin.com/in/clairevo [ https://substack.com/redirect/45ffec49-cf05-4d4b-bea7-4f14ba3f2034?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Podcast: https://www.youtube.com/@howiaipodcast [ https://substack.com/redirect/257dd5bb-e921-4725-a5ad-5937249b66d4?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Website: https://clairevo.com [ https://substack.com/redirect/7fd76845-3ad1-43fd-9f87-3368fe7e9b9e?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• ChatPRD: https://www.chatprd.ai [ https://substack.com/redirect/9ae27445-761e-4b67-9a01-9dbb7f73976c?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Referenced:
• OpenClaw: https://openclaw.ai [ https://substack.com/redirect/ea88ef29-9154-42c5-92c7-8d9020cde9cd?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Claude Cowork: https://claude.com/product/cowork [ https://substack.com/redirect/37f0d9e9-5c79-4f01-b3bd-5fd2d0d674a3?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Fry’s Electronics: https://en.wikipedia.org/wiki/Fry%27s_Electronics [ https://substack.com/redirect/04219cff-a016-498c-b1f5-b5a8617c817f?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Peter Steinberger on LinkedIn: https://www.linkedin.com/in/steipete [ https://substack.com/redirect/59339c68-e4bb-44ec-8e97-e53d34e49d9c?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Telegram: https://telegram.org [ https://substack.com/redirect/0355ff23-8819-45c5-90c8-d3940fab1236?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• WhatsApp: https://www.whatsapp.com [ https://substack.com/redirect/918cd828-5c7e-4445-ad0a-6bea1f95e6b3?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Fin: https://fin.ai [ https://substack.com/redirect/941f0e3a-7b88-4a4c-998f-523bd13d1de4?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Why OpenClaw feels alive even though it’s not (this AI has a heartbeat but not a brain): https://x.com/clairevo/status/2017741569521271175 [ https://substack.com/redirect/c5f9848f-21b8-4168-abab-795a47eff294?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• 5 OpenClaw agents run my home, finances, and code | Jesse Genet: https://www.youtube.com/watch?v=96Vl8s3EQhk [ https://substack.com/redirect/4a8ca0c6-4a4a-46f5-b2f4-19b0fc6a6c99?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Executive Playbook for AI in Engineering, Product, and Design: https://maven.com/clairevo/ai-native-epd-org [ https://substack.com/redirect/38ca6862-62d5-4174-ab17-d8a195bde543?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Zach Davis on LinkedIn: https://www.linkedin.com/in/zach-m-davis/ [ https://substack.com/redirect/8f7f6702-5f31-49b8-8ce3-1c94138b1a81?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• ChatGPT Atlas: https://chatgpt.com/atlas [ https://substack.com/redirect/71364909-2a4b-4520-ad62-1fcff0084f79?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Perplexity Comet: https://www.perplexity.ai/comet [ https://substack.com/redirect/07c50c61-0e19-4a38-aae8-a179f98589ee?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Browser (OpenClaw-managed): https://docs.openclaw.ai/tools/browser [ https://substack.com/redirect/46fc2f06-0ce6-4744-8db9-4af17e835b59?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Buffer: https://buffer.com [ https://substack.com/redirect/afd48707-f58e-4078-9d17-357f433354c8?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Brave: https://brave.com/search/api/ [ https://substack.com/redirect/2d61a38b-9878-4f14-ad1d-2b0b7ab88f39?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Exa: https://exa.ai [ https://substack.com/redirect/be0c9d4d-3856-4b92-90bd-8ab464426d3a?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Hilary Gridley on X: https://x.com/yourgirlhils [ https://substack.com/redirect/5a014655-068f-4e62-8739-2e13b5089f2e?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• How to become a supermanager with AI: https://www.lennysnewsletter.com/p/how-to-become-a-supermanager-with [ https://substack.com/redirect/bece4308-25fa-481d-bd66-7c1ef42f4c5e?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• How custom GPTs can make you a better manager | Hilary Gridley (Head of Core Product at Whoop): https://www.youtube.com/watch?v=xDMkkOC-EhI [ https://substack.com/redirect/32721c46-a8af-42b3-b445-a95f4060e0ed?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• How to debug a team that isn’t working: the Waterline Model: https://www.lennysnewsletter.com/p/how-to-debug-a-team-that-isnt-working [ https://substack.com/redirect/26db90fc-dded-4f63-b721-19fd84f753e4?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Jensen Huang on LinkedIn: https://www.linkedin.com/in/jenhsunhuang [ https://substack.com/redirect/e59d3568-4c24-4a38-82a3-826417ed9b78?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• How I built a 1M+ subscriber newsletter and top 10 tech podcast | Lenny Rachitsky: https://www.lennysnewsletter.com/p/how-i-built-a-1m-subscriber-newsletter [ https://substack.com/redirect/67cbfab8-2fc2-4263-91f9-c1b59de413a1?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Age of Attraction on Netflix: https://www.netflix.com/title/81779095 [ https://substack.com/redirect/bd8b7836-31fd-4e61-aff1-a3e4bcc298d0?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Oura Ring: https://ouraring.com/ [ https://substack.com/redirect/1f1991d3-a1ed-42cd-8af4-5915e52da725?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Eight Sleep: https://www.eightsleep.com [ https://substack.com/redirect/32727912-78aa-42b7-a905-b17286cb9621?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Hoopsalytics: https://hoopsalytics.com [ https://substack.com/redirect/ca95eeb8-9e5f-43c1-b420-93b2c700ba78?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• DJI Osmo smartphone gimbal: https://www.amazon.com/DJI-Stabilizer-Tracking-Extension-Stabilization/dp/B0FJ2L67HJ?ref_=ast_sto_dp [ https://substack.com/redirect/d76fffa4-1eb6-40ec-a778-aaa25f1ee531?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Silent basketball: https://www.amazon.com/Rzkipdy-Silent-Basketball-Size-27-5/dp/B0FHFSQWPP/ [ https://substack.com/redirect/29202eb1-af69-4b97-8a5f-980844648784?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Marc Andreessen: The real AI boom hasn’t even started yet: https://www.lennysnewsletter.com/p/marc-andreessen-the-real-ai-boom [ https://substack.com/redirect/ef9fd2ba-683b-4dbb-860f-ebbd55f29603?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Recommended books:
• Treasure Island: https://www.amazon.com/Treasure-Island-Robert-Louis-Stevenson/dp/1505297400 [ https://substack.com/redirect/1044c032-dfca-4a5d-8e36-c06e9d9e6a06?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Alice’s Adventures in Wonderland: https://www.amazon.com/Alices-Adventures-Wonderland-Illustrated-Illustrations/dp/991673268X [ https://substack.com/redirect/14911774-137b-4849-b057-8b7724217ea4?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Charts for Babies: A Picture Book: https://www.amazon.com/Charts-Babies-Picture-Book/dp/1419785184 [ https://substack.com/redirect/e26540e8-4308-40b4-978f-fa3f909302ba?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Production and marketing by https://penname.co/ [ https://substack.com/redirect/950f1681-b863-4ba4-b17b-57273b6c9ba8?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com [ mailto:podcast@lennyrachitsky.com ].
Lenny may be an investor in the companies discussed.
My biggest takeaways from this conversation:...
Unsubscribe https://substack.com/redirect/2/eyJlIjoiaHR0cHM6Ly93d3cubGVubnlzbmV3c2xldHRlci5jb20vYWN0aW9uL2Rpc2FibGVfZW1haWw_dG9rZW49ZXlKMWMyVnlYMmxrSWpvME1qWTFNVFV3TkRBc0luQnZjM1JmYVdRaU9qRTVNakF4TWpBMU5Dd2lhV0YwSWpveE56YzBOemc0TXpBM0xDSmxlSEFpT2pFNE1EWXpNalF6TURjc0ltbHpjeUk2SW5CMVlpMHhNRGcwTlNJc0luTjFZaUk2SW1ScGMyRmliR1ZmWlcxaGFXd2lmUS5JY05ZOTZyd0c1bUlBZGhNNURyTVpxalcwZ2FTekNxZDVrYWMzWndlaTRNIiwicCI6MTkyMDEyMDU0LCJzIjoxMDg0NSwiZiI6dHJ1ZSwidSI6NDI2NTE1MDQwLCJpYXQiOjE3NzQ3ODgzMDcsImV4cCI6MjA5MDM2NDMwNywiaXNzIjoicHViLTAiLCJzdWIiOiJsaW5rLXJlZGlyZWN0In0.2aF8iPce2vr26NzmQxnoB3k8pGPbtOXxxGPeZyZ3reY?
View Email
From skeptic to true believer: How OpenClaw changed my life | Claire Vo
lenny@substack.com3/29/2026
SubstackView this post on the web at https://www.lennysnewsletter.com/p/state-of-the-product-job-market-in-ee9
👋 Hey there, I’m Lenny. Each week, I answer reader questions about building product, driving growth, and accelerating your career. For more: Lenny’s Podcast [ https://substack.com/redirect/ccfc62d3-5bc3-4dcc-ac1f-796ea2aeab32?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] | Lennybot [ https://substack.com/redirect/1e48527a-cd9d-478d-859a-e5fd5947cedf?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] | How I AI [ https://substack.com/redirect/6ab07e16-557b-48e8-ba07-a6e8f06a73de?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] | My favorite AI/PM courses [ https://substack.com/redirect/d8067491-601d-4339-b70f-5723a0693a0a?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], public speaking course [ https://substack.com/redirect/17667f25-a91b-4a66-8ab4-271b6d098032?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], and interview prep copilot [ https://substack.com/redirect/208c6c74-241a-4004-8520-68a2cc163250?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
P.S. Get a full free year of Lovable, Manus, Replit, Gamma, n8n, Canva, ElevenLabs, Amp, Factory, Devin, Bolt, Wispr Flow, Linear, PostHog, Framer, Railway, Granola, Warp, Perplexity, Magic Patterns, Mobbin, ChatPRD, and Stripe Atlas by becoming an Insider subscriber [ https://substack.com/redirect/7065f952-a71d-4676-8ddd-30230ba4244c?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]. Yes, this is for real [ https://substack.com/redirect/bc609f42-fd5a-4723-bcb6-1a0650bf1377?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ].
Welcome to our biannual State of the Product Job Market—our fourth and, very surprisingly, the most optimistic. In spite of the headlines about layoffs and AI taking jobs, we’re actually seeing a lot of promising signs in tech hiring, and some interesting new trends:
PM openings are at the highest levels we’ve seen in over three years
AI hasn’t slowed the demand for software engineers (at least not yet)
AI roles in general are absolutely exploding
Design roles have plateaued
The Bay Area is increasing in importance
Remote work opportunities continue to decline
Despite ongoing layoffs, the overall number of tech jobs continues to grow
While these numbers are promising, I know a lot of people are having a hard time finding a job right now. And more openings doesn’t automatically mean people are finding jobs more quickly. For anyone in that situation, first of all, I’m sorry. Second, I’m working on ways to help. Until then, check out the end of this post for a bunch of resources I’ve collected that’ll improve your odds of landing a gig.
Let’s get into it.
This analysis is based on data from TrueUp [ https://substack.com/redirect/bb357974-8f9f-48fd-a2a2-c72e98c94d9f?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], one of my favorite collaborators and sources of data. They track job openings at tech companies and top startups around the world (over 9,000 companies) and make it easy to browse open gigs [ https://substack.com/redirect/8c2fa574-4654-4fcd-96fa-75173b36fb75?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]. Their data looks at roles at tech companies—the most sought-after and lucrative jobs. (It doesn’t include roles at non-tech companies and consulting agencies.)
1. PM openings are at the highest levels we’ve seen in over 3 years
There are over 7,300 open PM roles at tech companies globally, and trending up. This is 75% above the low we saw in early 2023, and already up nearly 20% since the start of this year. Today we have the most open PM roles we’ve seen since 2022. (You can see all of these open roles here [ https://substack.com/redirect/24e88cc8-933e-4c36-aa7b-3f494ee7cd16?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ].)
The same trend is true for engineering roles . . .
2. AI hasn’t slowed the demand for software engineers (at least not yet)
There are over 67,000 (!!!) eng openings [ https://substack.com/redirect/c1993646-a859-4183-a752-dd58476914b8?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] at tech companies globally right now, with 26,000 just in the U.S. We don’t know if there would have been more open roles if not for AI or if AI is actually leading to more open roles, but since the start of this year, the increase in open eng roles is accelerating even more.
If you’re skeptical that this growth is real and likely to be sustained, we’re also seeing a surge in demand for tech recruiters. The number of open recruiter roles is almost back to 2022 peak levels. This role got hit the hardest post-Covid, and also recovered the quickest. By definition, recruiting headcount expands and contracts with hiring demand, so it’s likely a leading indication that we’re tracking toward sustained highs in hiring demand in tech.
3. AI jobs in general are absolutely exploding
AI roles were already growing fast in our last update [ https://substack.com/redirect/cbdaeb3c-1a09-4502-af45-38e94227030b?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] mid-last year, but they are now hockey-sticking:
“AI roles” includes (1) all open roles at AI-driven companies, like OpenAI, Anthropic, Cursor, and Lovable, and (2) AI-specific roles at non-AI companies, like an AI PM at Figma. Browse them here [ https://substack.com/redirect/5ae59a1c-bdc8-4493-9e72-cadfe54260f9?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ].
Demand for AI engineers and AI PMs is similarly exploding.
Whether this is simply the number of AI companies being created or the headcount at top AI companies growing, it’s a good time to be in AI.
4. Design roles have plateaued
Unlike PM and engineering, open design jobs [ https://substack.com/redirect/706b50d2-2f30-49e2-80e8-0c33bde23dae?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] have been relatively flat since early 2023, and there are also fewer of these roles than PMs and engineers in absolute terms (about 5,700 globally).
I don’t know exactly what’s going on here, but it does feel AI-related. Unlike PM and eng, which started growing in 2024 (two years post-ChatGPT), design didn’t. If I had to venture a theory, I’d say that because AI is allowing engineers to move so quickly, there’s less opportunity—and less desire—to involve the traditional design process. A recent tweet commented on this same trend [ https://substack.com/redirect/66385872-2bbe-44c4-9101-7970fc6a3399?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]. That said, you’d think design would become a differentiator as more products compete for attention. Something to think about for your company! We’ll keep watching this trend and AI’s impact on org design more generally.
One interesting observation we made when we went a level deeper: the ratio of demand for PMs vs. designers has flipped. In mid-2023, we went from more open designer roles to more open PM roles. And ever since, PM demand has been pulling away (currently 1.27x). This will be another trend to monitor, in terms of how AI is reshaping org design.
5. The Bay Area continues increasing in importance
The Bay Area has long had the highest share of tech roles, but that share is still growing. Over 20% of all eng and designer roles are now in the Bay Area, and over 23% (!!!) of open PM roles are too (up 50% since 2022!). And all three are still going up.
A whopping third of open AI roles are based in the Bay Area, but, interestingly, this number has stayed relatively flat in the past few years. That tells me that the Bay Area unquestionably continues to be the center of AI (the next city is New York, with 10.2%), but at the same time, AI roles outside the Bay Area continue to grow at the same rate.
One more interesting data point: NYC has established itself as the #2 tech jobs location in the world, despite not being the headquarters of any of the leading tech companies. Bengaluru (formerly Bangalore), London, Tel Aviv, and Singapore continue to be the top international hubs for tech.
6. Remote work opportunities continue to decline...
Unsubscribe https://substack.com/redirect/2/eyJlIjoiaHR0cHM6Ly93d3cubGVubnlzbmV3c2xldHRlci5jb20vYWN0aW9uL2Rpc2FibGVfZW1haWw_dG9rZW49ZXlKMWMyVnlYMmxrSWpvME1qWTFNVFV3TkRBc0luQnZjM1JmYVdRaU9qRTVNVFU1TlRJMU1Dd2lhV0YwSWpveE56YzBNelUzTURrNExDSmxlSEFpT2pFNE1EVTRPVE13T1Rnc0ltbHpjeUk2SW5CMVlpMHhNRGcwTlNJc0luTjFZaUk2SW1ScGMyRmliR1ZmWlcxaGFXd2lmUS5kZC1ZeDQ3dU5IV192LUwxTDdma1k0SDRLVkFkLWRIVDV3bUdad09zbTAwIiwicCI6MTkxNTk1MjUwLCJzIjoxMDg0NSwiZiI6dHJ1ZSwidSI6NDI2NTE1MDQwLCJpYXQiOjE3NzQzNTcwOTgsImV4cCI6MjA4OTkzMzA5OCwiaXNzIjoicHViLTAiLCJzdWIiOiJsaW5rLXJlZGlyZWN0In0.wC3zKFFJ6ecOYmu4FsEz3-_YND2H6tI4RmBC31KwAos?
View Email
State of the product job market in early 2026
lenny@substack.com3/24/2026
SubstackView this post on the web at https://www.lennysnewsletter.com/p/the-art-of-influence-jessica-fain
Jessica Fain is a product leader at Webflow and former Chief of Staff to the CPO at Slack, where she worked alongside April Underwood and many past podcast guests including Stewart Butterfield, Annie Pearl, Tamar Yehoshua, and Noah Weiss. She’s spent her career learning how executives actually make decisions—and why most people completely misunderstand the process.
Listen on YouTube [ https://substack.com/redirect/569fefa3-4e90-4d74-9a07-a658e03b4224?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], Spotify [ https://substack.com/redirect/e9758bff-1ec5-400a-a126-8517991a607d?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], and Apple Podcasts [ https://substack.com/redirect/2ece606a-071d-4187-8042-a9d674bc5297?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
We discuss:
Why great ideas often don’t get buy-in
Why executive calendars are “like strobe lights” and why the first 30 seconds of a meeting matter so much
Why executives are usually optimizing for a global maximum while you are often optimizing locally
The best question Jessica uses when a leader says something that seems wrong: “That’s so interesting. What led you to believe that?”
Why you should go in to learn, not to convince
Why showing only one option is a mistake
Why AI will make influence more important, not less
Brought to you by:
Omni [ https://substack.com/redirect/b29d4d33-8057-4b06-ab21-3250023776e0?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]—AI analytics your customers can trust
Lovable [ https://substack.com/redirect/3946d30f-9836-4a64-add9-074dd4a0e7fc?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]—Build apps by simply chatting with AI
Vanta [ https://substack.com/redirect/fd0e94c7-8561-4178-88e6-b32a378e74f8?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]—Automate compliance, manage risk, and accelerate trust with AI
Where to find Jessica Fain:
• LinkedIn: https://www.linkedin.com/in/jessica-fain-79b8989 [ https://substack.com/redirect/7c21684b-5101-4bec-863e-ec0a4ab26694?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Referenced:
• Box: https://www.box.com [ https://substack.com/redirect/099641b4-fc5e-4761-a252-af3086dd8231?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Slack: https://slack.com [ https://substack.com/redirect/7b480940-8a01-4ac8-b02d-3b296385e3ef?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Brightwheel: https://mybrightwheel.com [ https://substack.com/redirect/61363124-2ce8-4b16-8f98-0162567ec247?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Webflow: https://webflow.com [ https://substack.com/redirect/358c5eff-3bb7-43e6-a07b-d7763614bf92?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• April Underwood on LinkedIn: https://www.linkedin.com/in/aprilunderwood [ https://substack.com/redirect/2542eff6-4fba-4a45-b5fd-38dbdcb7af17?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Lessons in product leadership and AI strategy from Glean, Google, Amazon, and Slack | Tamar Yehoshua (Product at Glean, ex-Google and Slack): https://www.lennysnewsletter.com/p/you-dont-need-to-be-a-well-run-company-to-win-tamar-yehoshua [ https://substack.com/redirect/ceae6900-3e18-420c-ac9f-9b2231db843d?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Atlassian: https://www.atlassian.com [ https://substack.com/redirect/5ab8c16d-04a7-47d8-9a37-e6c56b6d3513?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO): https://www.lennysnewsletter.com/p/behind-the-scenes-of-calendlys-rapid [ https://substack.com/redirect/26ab94e1-d5c2-47f7-9526-c8bdaf90b10a?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Calendly: https://calendly.com [ https://substack.com/redirect/a0cf8304-06b3-4947-bb1d-a621f9415a72?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Glassdoor: https://www.glassdoor.co.in/index.htm [ https://substack.com/redirect/9baf41cc-645c-4143-ab89-3410d3db2241?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• The 10 traits of great PMs, how AI will impact your product, and Slack’s product development process | Noah Weiss (Slack, Foursquare, Google): https://www.lennysnewsletter.com/p/the-10-traits-of-great-pms-how-ai [ https://substack.com/redirect/39bb8fe0-0c7e-4df0-817d-e7305d05680b?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Ethan Eismann on X: https://x.com/eeismann [ https://substack.com/redirect/76d66e88-d65f-483c-bd7a-9d582a9b28a4?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Slack founder: Mental models for building products people love ft. Stewart Butterfield: https://www.lennysnewsletter.com/p/slack-founder-stewart-butterfield [ https://substack.com/redirect/29c07553-66d1-4687-a818-f686fa3e019f?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Ilan Frank on LinkedIn: https://www.linkedin.com/in/ilanfrank [ https://substack.com/redirect/e5dddf96-6134-4223-a1ab-2c5a0dce9d46?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Checkr: https://checkr.com [ https://substack.com/redirect/3fa3b42b-3123-4f53-b9e4-7d14f78b3590?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Ali Rayl on LinkedIn: https://www.linkedin.com/in/alirayl [ https://substack.com/redirect/cd3a4e2c-27a1-4f46-8e3f-ef194afc5b60?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Rachel Wolan on LinkedIn: https://www.linkedin.com/in/rachelwolan [ https://substack.com/redirect/d2327584-735d-48b3-9dff-90bdb4c7fe5c?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• How Webflow’s CPO built an AI chief of staff to manage her calendar, prep for meetings, and drive AI adoption | Rachel Wolan: https://www.lennysnewsletter.com/p/how-webflows-cpo-built-an-ai-chief [ https://substack.com/redirect/b9da8a72-0cc8-41df-a4f2-8d1c5cedb365?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Barbara Minto’s website: https://www.barbaraminto.com [ https://substack.com/redirect/d23125b7-be99-4279-9dfe-c3fd4628dc84?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• How Slack invests in big little details through Customer Love Sprints: https://slack.design/articles/sweating-the-small-stuff [ https://substack.com/redirect/27a5c736-de2e-415b-8fc9-b81a0b41d6da?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Building product at Stripe: craft, metrics, and customer obsession | Jeff Weinstein (Product lead): https://www.lennysnewsletter.com/p/building-product-at-stripe-jeff-weinstein [ https://substack.com/redirect/dcc68fd3-f39d-4954-8a86-d022b1f64ccb?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• The Enneagram Institute: https://www.enneagraminstitute.com/type-descriptions [ https://substack.com/redirect/268917af-073e-4165-823f-a6361531a6c2?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• The Pitt on Prime Video: https://www.amazon.com/The-Pitt-Season-1/dp/B0DNRR8QWD [ https://substack.com/redirect/d0ed56d9-52ed-42a0-aeb6-65e3889b38aa?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Towel warmer: https://www.amazon.com/FLYHIT-Large-Towel-Warmer-Bathroom/dp/B0CB5K34L2 [ https://substack.com/redirect/ffc3187c-e86e-4296-9863-3c37dccb130d?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Casa: https://getcasa.com [ https://substack.com/redirect/15481778-5e6b-426b-a456-b4e98da5bf7e?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Jimi Hendrix: https://en.wikipedia.org/wiki/Jimi_Hendrix [ https://substack.com/redirect/540edca0-09a3-4c65-b601-9fd6cc4ceaf7?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Greek Theatre: https://en.wikipedia.org/wiki/Greek_Theatre_(Los_Angeles) [ https://substack.com/redirect/549c1c69-2ec5-4493-9f7c-1b546d571a74?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Recommended books:
• Pachinko: https://www.amazon.com/Pachinko-National-Book-Award-Finalist/dp/1455563927 [ https://substack.com/redirect/62d8f0ae-a1a5-4cc5-8d7b-abb3c23d5915?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Homegoing: https://www.amazon.com/Homegoing-Yaa-Gyasi/dp/1101971061 [ https://substack.com/redirect/9d9ff9fb-d13a-4a50-a3c9-da07c5d39f48?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• A History of Burning: https://www.amazon.com/History-Burning-Janika-Oza/dp/1538724243 [ https://substack.com/redirect/b3a097c2-2f6b-4e4e-923f-b3a9ceedcbec?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• The Overstory: https://www.amazon.com/Overstory-Novel-Richard-Powers/dp/039335668X [ https://substack.com/redirect/6b3968c4-2e3c-42a4-bf8a-bdc65fb6cccf?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Production and marketing by https://penname.co/ [ https://substack.com/redirect/cc4aefd7-ea79-4f47-90c8-413813b3cc66?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com [ mailto:podcast@lennyrachitsky.com ].
Lenny may be an investor in the companies discussed.
My biggest takeaways from this conversation:...
Unsubscribe https://substack.com/redirect/2/eyJlIjoiaHR0cHM6Ly93d3cubGVubnlzbmV3c2xldHRlci5jb20vYWN0aW9uL2Rpc2FibGVfZW1haWw_dG9rZW49ZXlKMWMyVnlYMmxrSWpvME1qWTFNVFV3TkRBc0luQnZjM1JmYVdRaU9qRTRPVGM0TnpBek1Td2lhV0YwSWpveE56YzBNVGd6TlRJMUxDSmxlSEFpT2pFNE1EVTNNVGsxTWpVc0ltbHpjeUk2SW5CMVlpMHhNRGcwTlNJc0luTjFZaUk2SW1ScGMyRmliR1ZmWlcxaGFXd2lmUS5VMWc4bGtDZkszRFY3cGV0MzNMbVdqYmctNHhsMkR2bXJGMS1qUHdUWk04IiwicCI6MTg5Nzg3MDMxLCJzIjoxMDg0NSwiZiI6dHJ1ZSwidSI6NDI2NTE1MDQwLCJpYXQiOjE3NzQxODM1MjUsImV4cCI6MjA4OTc1OTUyNSwiaXNzIjoicHViLTAiLCJzdWIiOiJsaW5rLXJlZGlyZWN0In0.LLqvpDuoZhbEDk39JN9aESuaEfNHxXbL8iKaUQp198U?
View Email
The art of influence: The single most important skill that AI can’t replace | Jessica Fain (Webflow, ex-Slack)
lenny@substack.com3/22/2026
SubstackView this post on the web at https://www.lennysnewsletter.com/p/how-i-built-lennyrpg
👋 Each week, I answer reader questions about building product, driving growth, and accelerating your career. For more: Lenny’s Podcast [ https://substack.com/redirect/094125a6-6128-4419-a0e6-d10597177b24?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] | Lennybot [ https://substack.com/redirect/83514cdd-2401-44eb-a6cd-12e07cd192be?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] | How I AI [ https://substack.com/redirect/a61bdfd8-dc70-4f3d-b7b9-5c8736dd9317?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] | My favorite AI/PM courses [ https://substack.com/redirect/053449c4-3c73-4edd-ba38-2ca2c7cf0f80?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], public speaking course [ https://substack.com/redirect/ead67eca-d036-4f95-9379-45f1cc4b5356?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], and interview prep copilot [ https://substack.com/redirect/b2537b44-9e3c-491e-a119-34b734f18a7d?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
P.S. Get a full free year of Lovable, Manus, Replit, Gamma, n8n, Canva, ElevenLabs, Amp, Factory, Devin, Bolt, Wispr Flow, Linear, PostHog, Framer, Railway, Granola, Warp, Perplexity, Magic Patterns, Mobbin, ChatPRD, and Stripe Atlas by becoming an Insider subscriber [ https://substack.com/redirect/0a2015bc-5a12-4efe-b314-06e7177865a4?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]. Yes, this is for real [ https://substack.com/redirect/8957645b-b574-4b2c-8e3a-f289b7d69afb?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ].
A few months ago, I shared all of my podcast transcripts on socials on a whim, and holy sh*t, y’all found such incredibly creative ways to use this data: parenting wisdom rooted in PM advice [ https://substack.com/redirect/43d03aed-73bc-42f7-b3e6-92c4c1fed6b6?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], user research scripts [ https://substack.com/redirect/d48624df-3ba2-4233-9582-df55f5d66e7b?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], antimemes [ https://substack.com/redirect/f7416972-2776-443b-841d-3b2a3df018c4?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], an infographic for every episode [ https://substack.com/redirect/597d8f8e-25e3-49a5-a19d-5c6e50143cb8?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], a “Learn from Lenny” Twitter bot [ https://substack.com/redirect/8cfc5a9c-86e8-4c1e-9d82-d24f2a12f388?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], and at least 50 other amazing projects.
But my favorite project of all was by Ben Shih [ https://substack.com/redirect/781ddf84-88f2-41fe-bc08-345afb219151?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], a non-technical product designer at Miro, who created LennyRPG [ https://substack.com/redirect/598387d9-a223-44db-9cb7-2812bdb14454?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]. I asked Ben to share the step-by-step journey behind this wildly fun, video-game-inspired project—how he built it and what he learned.
To let a thousand more flowers bloom, today I’m releasing my entire newsletter archive (and my podcast transcripts) in AI-friendly Markdown files. Also, an MCP server and a handy GitHub repo. Paid subscribers get all of the data (some 350 posts and 300 transcripts); free subscribers can access a subset. Grab the data here: LennysData.com [ https://substack.com/redirect/1ac201be-4635-4524-bf62-615af74b5f6f?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ].
I don’t think anyone’s ever done anything like this before, and I’m excited to give you this excuse to start playing with the latest and greatest AI tools.
Here’s my challenge to you: build something, and let me know about it. I’ll pick my favorite and give you a free 1-year subscription to the newsletter. Just post a link to your project in the comments below. If you’ve already built something, slurp in this new data and submit it, too. I’ll pick a winner on April 15th. Here’s the data [ https://substack.com/redirect/1ac201be-4635-4524-bf62-615af74b5f6f?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]. Let’s go.
Ben is a designer and product builder who enjoys creating small, fun, and thoughtful products that make the world a little better. He’s currently a growth designer at Miro. You can explore more of his work on his website [ https://substack.com/redirect/db4da78f-d2d8-4351-a508-2925306fddf5?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] or LinkedIn [ https://substack.com/redirect/983fc154-a676-43bd-9f68-82fbb718a495?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ].
Also, a big thank-you to Tal Raviv [ https://substack.com/redirect/02225581-9e2e-4f3f-9296-8f2a8df497b4?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], Claire Vo [ https://substack.com/redirect/a86c5916-f6ff-445a-95b2-20de4e90b771?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], and Este Lopez [ https://substack.com/redirect/2093d627-d315-40b3-a748-31e9bf8c66ea?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] for helping me beta-test and improve LennysData.com (which I proudly “agentically engineered” with Codex and Claude Code 👌).
A couple months back, Lenny dropped something special. He made transcripts from all his more than 300 podcast episodes [ https://substack.com/redirect/c7ba9849-53a2-4c9c-9529-a6c24efe05f8?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] structured and publicly available. As someone who’s listened to the podcast for years, I couldn’t stop thinking about what I could actually build with this.
Brian Balfour [ https://substack.com/redirect/c9afe4fb-dc8f-4c61-a251-5dc07c476323?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] talks a lot about building at the right moment: if you get the timing right, you’ll find a real window of opportunity. This felt like one of those windows.
The first idea that popped into my mind was to make a Lenny interview app where you can practice job interviews with Lenny’s Podcast guests. However, the more I thought about that idea, the less excited I felt. Interview practice tools by nature feel stressful, and that’s the last type of product I wanted to create. I wanted to make something fun.
What if I turned Lenny’s Podcast into a small role-playing game (RPG)? A game where you explore a pixel world, meet guests from Lenny’s Podcast, compete with them to test your product knowledge, and even capture them like Pokémon when you win. That’s how LennyRPG was born.
Here’s how I built it
When I build apps with AI, I usually follow a very simple flow:
Define the core idea: I start by clarifying what the app is. For visually heavy products, I sketch it out so the AI can better understand the requirements.
Create a product requirement document (PRD): I turn the core idea into a proper PRD with the AI. This becomes the single source of truth for the build.
Create a proof of concept: I use the PRD to plan implementation and build the core functionalities first.
Add remaining features: I finish the end-to-end flow, such as connecting the database and building out settings, profile pages, and other non-core features.
Polish: I go through the app end-to-end, fix UX/UI details, and do final code reviews to make sure everything is stable.
Ship it: I deploy, get feedback, and get it out into the world.
The process isn’t that different from before the AI era. But now I really make sure that I spend enough time on the first two steps to ensure that the AI gets all the context of what I want. In my experience, nailing the core idea and PRD determines 80% of how smooth the rest of the build will be.
Here are the main tools and technologies I used throughout the build:
Ideation and planning: Miro, ChatGPT
Coding: Claude Code, Codex, Cursor
Image generation: GPT Image Gen (gpt-image-1.5)
Quiz generation: GPT-4o
Game engine: Phaser 3
Database: Supabase
Deployment: Vercel
Now let’s walk through how I used this process to build my RPG game. I’ll share the exact prompts, tools, and decisions at each step so you can apply the same workflow to your own projects.
1. Define the core idea
The core idea was simple: turn Lenny’s Podcast into a Pokémon-style RPG where players encounter podcast guests in the wild and battle them through product questions.
For many apps, text and a clear idea are enough to get started with. But for highly visual products like this game, spending some time on visualization can help you get a solid sense of how you want the game to look and feel. That makes a big difference later on when you ask the AI to build the UI and interactions.
For this game, I dropped a few Pokémon screenshots into a Miro board and put together a rough concept directly on the board. Nothing fancy, mostly text and boxes on top of screenshots. But it was enough to show how I imagined the map, the battle screen, and how the characters might look.
The goal was not to design the game exactly but to give the AI something concrete to read and reason about. Once the core idea was roughly visualized, the AI could read the visuals alongside the text, which led to a much stronger PRD in the next step.
Creating a sample set of avatars
As part of the visualization, I also created a few test avatars with ChatGPT to validate the content generation workflow. This helped me understand the prompt engineering needed for consistent pixel art style avatars.
The process was very simple. I dragged in images of the RPG characters I wanted the style to match, then added Lenny’s photo into ChatGPT to create a similar one.
Once I was happy with it, I asked ChatGPT to describe the tone, style, and design in detail so that I could reuse that as a prompt later.
Prompt I used:
Study and think through the styling, design, colors, proportions, and overall look in detail, then return only a polished image-generation prompt that will create a similar front-facing character based on the provided person’s photo, with a transparent background and no additional elements.
2. Create a PRD (in a lazy way)
In my experience, the PRD is the most important document if you want the AI to execute your vision correctly. As a PRD does well with human teammates, it gives the AI the base understanding of your app’s goal, problem statement, and core idea. Whenever the AI hits a wall or the context window runs out, you can refer it back to the PRD to realign. No matter what stage you’re at, the PRD makes sure everything the AI generates stays true to what you’re actually trying to build. That’s why I always invest time here.
That said, writing PRDs can sometimes drive you crazy. So instead of writing the PRD myself from scratch, I let the AI interview me. I pasted my core idea along with the visuals into ChatGPT and then asked it to ask me questions so that I could answer them one by one.
Prompt I used:
Ask me questions to help you put together a brief PRD for the following web game: I want to create a mini game that takes all the podcast episodes from Lenny’s Podcast, generates questions from each episode, and make it like a Pokémon RPG game, with similar visuals. What I am expecting is, for example, you found Elena in the wild, and you can compete with Elena on product questions, you get 5 questions, and you lose HP [hit points] when you lose the answer etc. We can randomly pick 50 guests from the podcast and get challenged. The entire theme/design of the game needs to be very Pokémon RPG style in the old day.
With the prompt, ChatGPT came back with 17 questions. I moved them into Miro to visualize them better and used Wispr Flow [ https://substack.com/redirect/8e9cb1ad-0143-4991-8938-8b5409549fde?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] to quickly dictate my answers verbally.
Answering these questions also forced me to think through gaps and assumptions in my idea, while giving the AI much better context than a one-page description ever could.
Once I answered all of the questions the AI had for me, I chained the answers together with all the available artifacts in Miro and asked the AI to generate a comprehensive PRD.
3. Create a proof of concept
With the PRD in place, I moved it over to Cursor as a Markdown file so I could start working on the POC.
For the actual development, my setup uses three tools: Claude Code, Codex, and Cursor’s Composer.
I treat Claude Code as my lead engineer. It helps draft the implementation plan, think through architecture, and reason about product and design constraints. I’ve also found it to be great at searching for solutions and open source libraries. Codex is mainly for executing tasks from the implementation plan. It’s very good at following instructions accurately, and comes with a more generous token limit. Composer is mostly for smaller tasks like formatting documents, JSON files, or writing simple scripts.
Using the PRD as input, I first asked Claude Code to search for any open source projects that could help me move faster. This is something I always do early on. Very often, people have already built something similar and made it open source on GitHub, which can help you set things up much faster.
One of the first libraries I landed on was RPG-JS [ https://substack.com/redirect/8b5fc45e-577c-460b-ac7c-0d0b87a1ea42?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]. Thanks to the library, it took me around five minutes to get something running. I was able to quickly build out the essential game flow. The overworld map handled basic player movement, encounter zones, and simple UI elements.
But very quickly, I started hitting challenges.
Challenge #1: Hitting the limits of RPG-JS and pivoting
After a few iterations, it became clear that RPG-JS was not the right foundation. The framework is heavily designed around inventory systems and weapon-based combat. That worked against me, since my battles were quiz-based and logic-driven. The more I tried to bend it, the harder it became for the AI to reason about the system cleanly.
After talking it through with Claude Code, I decided to stop forcing it and pivot. The new framework that I decided to use is Phaser [ https://substack.com/redirect/b4d3328d-c464-40f5-85e0-f148edbdf439?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], a 2D game framework used for making HTML5 games for desktop and mobile.
Challenge #2: Getting the map running in Phaser
After switching to Phaser, things became much more flexible in terms of scenes, maps, and game logic. However, because everything is more customizable, even setting up a basic map took a lot more work.
Fortunately, using Claude Code, I found a Medium article [ https://substack.com/redirect/4c5aa3f6-3c1a-4489-a9d1-ea8855ca1697?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] from a while ago that included an open source, reusable map template. That helped me speed things up significantly and get back to focusing on the game itself.
Challenge #3: Polishing the details in Phaser
Phaser is a powerful but complex library with a lot of different features. Claude Code took some time to actually understand how it works, and I had to go through many iterations to get the details right. Things like importing the right fonts, making sure UI elements were positioned correctly, and editing everything within Phaser’s open canvas all required a lot of back and forth.
One tip for complicated tasks like this is to ask Claude Code to create a simple Markdown file to log everything it tries, so it can keep referring back and updating what works and what doesn’t.
This helps a lot for Claude Code and AI in general to understand the codebase and framework better. It’s especially useful as your codebase grows larger, where even small things like font changes can become difficult for an AI to handle.
After working through all these challenges, the game finally reached a playable state. The starting screen, map, and battle screen were all working end-to-end.
Once the POC was ready, I shared it internally in the office to get a few people to try it out. At this stage, I wasn’t looking for polished feedback or detailed bug reports. I mostly wanted to see how people reacted when they opened the game for the first time. Did they immediately understand what to do? Did the core loop make sense? Most importantly—did it feel fun, or did it feel like work?
This kind of lightweight, informal testing gave me confidence that the core idea worked, and that it was worth investing more time to turn the POC into something more complete.
4. Add remaining features
Once I got the app running correctly with the basics and got great feedback from folks in the office, I started following the plan to scale my POC into a proper game.
But the process was less straightforward than expected, mainly because there were a lot of podcast episodes to process. Scaling from a working POC to a full game turned out to be mostly about figuring out how to handle things systematically instead of manually.
Here are the main tools and decisions that helped me get there:
Processing 300+ transcripts systematically
The transcript file provided by Lenny contained only raw text. To make it usable in the game, I first had to enrich the data with things like episode title, episode URL, and podcast cover.
To do this, I pulled in the podcast RSS feed [ https://substack.com/redirect/f6ad09c3-0881-4baf-bba1-208ea1e05893?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] with Cursor’s Composer and used it to attach the missing metadata to each transcript. This gave me a much more complete dataset that the game could actually use.
Then, using Claude Code, I asked it to create a simple CLI tool that could systematically generate quiz questions for each episode using the OpenAI API. Instead of doing this episode by episode, the tool processed everything in one go.
This step was as simple as typing in a prompt: “Create a CLI command tool that creates a simple way to read through all the transcripts in /transcript folder one by one, and for each, generate 5 questions following the requirements and JSON format: {Your requirements and JSON format}”
It took around 20 minutes to finish, and the output was a structured JSON file that I could plug directly into the game.
The potential nightmare of creating 250+ RPG avatars
One of the hardest parts of building the game was creating over 250 RPG avatars in a consistent way. Each avatar needed a photo of the guest as input. Doing this manually by searching and downloading guest photos one by one would have taken forever.
Fortunately, every Lenny’s episode already includes an episode cover that contains the guest’s avatar. For this, I triggered Cursor’s Composer to pull RSS feed again to pull the image URLs, downloaded them locally, and used those as inputs for avatar generation.
That solved the sourcing problem but introduced another one: How do I make sure every avatar looks consistent in quality and style?
This is where I used OpenAI Playground to repeatedly test and refine my prompt, as well as testing which models work the best for the task. I kept adjusting it until every generated avatar followed the same style and looked like it belonged to the same game.
Once the prompt was stable, I used Claude Code again to write another CLI tool that could systematically generate all the RPG avatars from the episode covers. That turned a very painful manual task into a one-click process.
And of course, for each output, I had to check one by one to make sure the sizes and styling were similar and matched how the guests looked in the podcast cover. This was one of the most interesting steps because there were a few fun edge cases. For example, I didn’t know Adam Grenier really has rabbit ears on top of his profile image in the original podcast cover—I almost deleted them. Or there are episodes with two people in the cover image, like Jake Knapp and John Zeratsky’s episode, so I had to tell AI to generate a single separate image for each person.
Claude Code’s magic with background music
Audio is a huge part of any game. Many successful gamified apps, like Duolingo, invest a lot of effort in sound design because it makes everything feel more alive.
At the same time, searching for the right background music and wiring it into the game usually takes a lot of time. So I went to Claude Code and simply said: “Search for me background music for each phase, with mute control.”
To my surprise, it was able to find OpenGameArt.org [ https://substack.com/redirect/e40e63b7-68c1-4a1f-9c04-25d150240b59?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], an open source audio library for games, and wire it into the game correctly. When I wrote the prompt, I actually just wanted to add background music for when players are on the map, but it automatically added music for battle screens, victory screens, and defeat screens as well. I still had to adjust the timing and volume, but most of the heavy lifting was done automatically. That part genuinely felt like magic.
Defining the gaming mechanics
Defining the gaming mechanics was the most interesting part of the process, as I wanted the game to be fun and low-stress but still competitive enough that people felt progression and stakes. I’ve studied game theory in the past, but for this project, most of it came down to common sense, play testing, and iteration.
I started with a very simple rule set: Each opponent has three questions. Every correct answer gives XP (experience points). If you answer all three correctly, that counts as a perfect kill.
To keep things interesting, I added small variations. Occasionally, one of the three questions becomes a bonus question, which gives extra XP and a small HP boost. This introduces a bit of randomness without breaking balance.
Stage progression is based on XP thresholds. Once you reach the required XP, a new map unlocks with a new batch of guests. Defeated opponents disappear and get added to your collection, so you can’t farm the same ones repeatedly.
I worked through most of this logic on my own first and then verified with the AI to make sure there were no obvious bugs or edge cases. The AI sanity-checked numbers and flows, but the final calls on balance, pacing, and stress level were all manual.
Connecting Supabase using MCP (leaderboard)
The last step of the game is the leaderboard. It is the competition aspect of the game, where people can see their ranking and compete with each other.
I knew I had to set up a database for this, so I started by setting up Supabase MCP in Claude Code. That means instead of manually setting up tables, APIs, and connections, all I had to do was describe to Claude Code that I wanted a leaderboard synced with Supabase.
Once I did that, it triggered Supabase MCP, which called tools like create_project and apply_migration to set up the project and tables automatically, including the database structure and the connection between the game and Supabase. This made the whole process much faster and removed a lot of setup work that would normally take much longer.
The result was a working leaderboard that synced player progress in real time, without my having to touch much backend code at all.
5. Polish
Before shipping, I focused on final polish to make sure the app was stable, usable, and presentable enough for public launch. At this stage, the core gameplay was already working, so the goal was not to add new features but to reduce friction and obvious issues.
QA check with Claude Skills
For this step, I downloaded the review skill from the Claude Code Awesome Skills marketplace [ https://substack.com/redirect/5892ff57-9d2d-40a8-8caa-df46ff30beed?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] and used it to review the entire codebase comprehensively.
This was especially helpful for catching things I would normally miss, such as state issues between scenes, missing error handling, and small logic bugs that only show up after multiple rounds of gameplay. I did not blindly accept everything it suggested, but it gave me a solid checklist to go through before shipping.
UI polish
I went through the game end-to-end and logged all UI and UX inconsistencies in a Markdown file—things like spacing issues, text overflow, unclear labels, alignment problems, and visual hierarchy issues.
Once everything was written down, I let AI pick up the list one by one and fix them. This worked surprisingly well, especially when the issues were clearly described. It also made the process much more systematic compared with fixing things ad hoc while clicking around the app.
SEO
For SEO, I used Claude Code to help figure out the basics: page title, meta description, social preview, and basic indexing setup.
Since this was a game and not a content-heavy site, I did not go deep into SEO optimization. The main goal was to make sure the site was indexable, shareable, and looked good when people posted it on social media.
6. Ship it
Once the game was deployed smoothly on Vercel, I reached out to Lenny in the community Slack to get a quick sanity check. I honestly wasn’t even expecting a direct reply given how busy he is—but to my surprise, I got a very kind and encouraging response from him.
That was the nudge I needed to just ship it.
Unsubscribe https://substack.com/redirect/2/eyJlIjoiaHR0cHM6Ly93d3cubGVubnlzbmV3c2xldHRlci5jb20vYWN0aW9uL2Rpc2FibGVfZW1haWw_dG9rZW49ZXlKMWMyVnlYMmxrSWpvME1qWTFNVFV3TkRBc0luQnZjM1JmYVdRaU9qRTRPVFV3TkRReE1Dd2lhV0YwSWpveE56Y3pOelV5TXpjeExDSmxlSEFpT2pFNE1EVXlPRGd6TnpFc0ltbHpjeUk2SW5CMVlpMHhNRGcwTlNJc0luTjFZaUk2SW1ScGMyRmliR1ZmWlcxaGFXd2lmUS5tZm1lX250cTJ6UDVRSXduVXRuUjZmSVpxOENxN0pPb1p4M3lZdlBQZlA4IiwicCI6MTg5NTA0NDEwLCJzIjoxMDg0NSwiZiI6dHJ1ZSwidSI6NDI2NTE1MDQwLCJpYXQiOjE3NzM3NTIzNzEsImV4cCI6MjA4OTMyODM3MSwiaXNzIjoicHViLTAiLCJzdWIiOiJsaW5rLXJlZGlyZWN0In0.P-s4Rmw_3_68iJ3nhPfYRhM7bz_gj5u5dcId139VyRs?
View Email
How I built LennyRPG
lenny@substack.com3/17/2026
SubstackView this post on the web at https://www.lennysnewsletter.com/p/the-tactical-playbook-for-getting-more-comp
Jacob Warwick is an executive negotiation coach who helps senior operators negotiate better salary, equity, titles, and severance packages. He has worked with leaders across tech and Hollywood, was previously a founder and CEO himself, and has helped clients secure millions in additional compensation. His approach focuses on collaboration over confrontation, understanding motivations, and treating job searches like enterprise sales processes.
Listen on YouTube [ https://substack.com/redirect/d5ab20af-bfae-4989-9b3f-a608051811ec?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], Spotify [ https://substack.com/redirect/18f92479-4b27-4ee3-b394-cf9192151ab9?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], and Apple Podcasts [ https://substack.com/redirect/872d1abf-1572-4bf5-8132-39cd60f194a4?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
We discuss:
Why a simple “What’s the chance there’s a little more here?” often unlocks a 20% bump
Why Jacob sees 40% average movement when negotiations are run well
When negotiation actually starts (hint: it’s much earlier than you think)
Why information + timing create power
The biggest mistakes people make when negotiating
How to navigate the important “What’s your comp expectation?” question without anchoring too low
Why the best interviews feel more like discovery calls than interrogations
Brought to you by:
Orkes [ https://substack.com/redirect/c184e3b1-4e26-4f32-8a7d-45db03b1cd20?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]—The enterprise platform for reliable applications and agentic workflows
Mercury [ https://substack.com/redirect/358029cd-fc5f-49b2-b95a-999c17d0871c?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]—Radically different banking
Omni [ https://substack.com/redirect/d59b3550-b96b-427a-8247-40523dfc53d9?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]—AI analytics your customers can trust
Where to find Jacob Warwick:
• Substack: https://www.execsandthecity.com [ https://substack.com/redirect/016e5779-f077-451b-a7e0-d3697d688ca5?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• YouTube: https://www.youtube.com/@ExecsandtheCity [ https://substack.com/redirect/e3b5ccd1-e2f7-4ba2-9d75-3ea8d478a403?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Website: https://www.thinkwarwick.com [ https://substack.com/redirect/70e363ab-2fbf-454f-ad81-a68710fb3b82?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Complete Job Search Course: https://www.execsandthecity.com/p/complete-job-search-course [ https://substack.com/redirect/281b13d0-855c-4998-905f-d60ae5d4a4a6?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Referenced:
• The ultimate guide to negotiating your comp: https://www.lennysnewsletter.com/p/the-ultimate-guide-to-negotiating [ https://substack.com/redirect/545f37f4-492c-42f3-b5c5-00fc05f32f7b?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Sam Altman on X: https://x.com/sama [ https://substack.com/redirect/3d035ca5-4775-4fd7-97ec-f171ab20e13a?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Tom Brady on X: https://x.com/TomBrady [ https://substack.com/redirect/deeeca38-6462-4377-824c-38a3bf00205f?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Career Huddle: Interview & Negotiation Master Class with Jacob Warwick: https://www.youtube.com/watch?v=TgjWTiSj8E8 [ https://substack.com/redirect/13c23026-a1d2-471d-ba3c-9b2bc338c643?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Salesforce: https://www.salesforce.com [ https://substack.com/redirect/54ada251-1d9d-43fe-bee2-b20dee5765e7?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Julia Roberts: https://en.wikipedia.org/wiki/Julia_Roberts [ https://substack.com/redirect/f2d9d5ee-4a2a-401e-afca-0572e9ded063?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Matt Damon: https://en.wikipedia.org/wiki/Matt_Damon [ https://substack.com/redirect/114fd6da-7fce-47b7-97e9-be3e840ca6a9?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Steven Spielberg: https://en.wikipedia.org/wiki/Steven_Spielberg [ https://substack.com/redirect/6a96127c-9f0e-4266-8e6d-4a0a9d131510?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Marc Andreessen: The real AI boom hasn’t even started yet: https://www.lennysnewsletter.com/p/marc-andreessen-the-real-ai-boom [ https://substack.com/redirect/3fac017d-e39f-459f-8071-8528e6e7e392?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Chris Voss’s quote: https://www.goodreads.com/quotes/10181396-remember-never-be-so-sure-of-what-you-want-that [ https://substack.com/redirect/4d214c31-16e2-4934-93f2-368f5b9824e7?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Chris Voss on X: https://x.com/fbinegotiator [ https://substack.com/redirect/0a190d38-46b6-46eb-89e0-0c42ff89c15f?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Werewolf: https://playwerewolf.co [ https://substack.com/redirect/0f7ab718-aa4b-470b-b266-5b428223b288?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Modes of persuasion: https://en.wikipedia.org/wiki/Modes_of_persuasion [ https://substack.com/redirect/6faddab3-26cc-4f39-9fd8-ee4a74c7a4aa?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• How to use tactical empathy: https://www.linkedin.com/posts/christophervoss_tacticalempathy-negotiation-customerexperience-activity-7361004118808670212-oeRy [ https://substack.com/redirect/c4c7f257-bd27-41d0-b8ec-5df56d76dfca?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• ZOPA, BATNA and Win-Win in Negotiation: https://www.parallelprojecttraining.com/blog/zopa-batna-and-win-win-in-negotiation [ https://substack.com/redirect/43add7a7-b2af-4ff9-9ca3-a724817373cf?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Marvel: https://www.marvel.com [ https://substack.com/redirect/c9905dee-9766-47f8-a004-959467cb407e?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Negotiation Made Simple podcast: https://www.buzzsprout.com/2227030 [ https://substack.com/redirect/cf4d8a79-50e2-4082-bdf9-1d5fabd2372c?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Luca on Disney+: https://www.disneyplus.com/browse/entity-f28b825f-c207-406b-923a-67f85e6d90e0 [ https://substack.com/redirect/e32a2d5c-a2f5-460f-bef3-158f61d66d02?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Minuscule: https://www.youtube.com/user/Minuscule [ https://substack.com/redirect/781354f7-a942-433a-92ab-e8e8ad2718ac?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Claude Cowork: https://claude.com/product/cowork [ https://substack.com/redirect/7c708bb0-e797-49a5-851a-86e00d29c6a6?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Macrofactor: https://macrofactor.com [ https://substack.com/redirect/85293285-5081-45f7-a34c-5726b2703ae3?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Whoop: https://www.whoop.com [ https://substack.com/redirect/be1d6c79-87e8-434c-b86b-f057a32e1e33?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Gemini: https://gemini.google.com/app [ https://substack.com/redirect/c76fd575-413d-44a9-8f30-a791ce52e173?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• The Cody Dieruf Foundation: https://breathinisbelievin.org [ https://substack.com/redirect/582cb12e-e593-4edf-a2b2-557e24827ce0?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Cystic Fibrosis Foundation: https://www.cff.org [ https://substack.com/redirect/d31404cb-66a3-4b84-83b6-c00726efdc5d?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Recommended books:
• Negotiation Games: https://www.amazon.com/Negotiation-Games-Routledge-Advances-Theory/dp/0415308941 [ https://substack.com/redirect/a9ba4f24-e7a9-4c6b-a025-f83ddf040ee2?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Influence: The Psychology of Persuasion: https://www.amazon.com/Influence-Psychology-Persuasion-Robert-Cialdini/dp/006124189X [ https://substack.com/redirect/13d25866-3a6e-49dc-a3f5-0932039ea4b9?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• You Can Negotiate Anything: How to Get What You Want: https://www.amazon.com/You-Negotiate-Anything-Herb-Cohen/dp/0806541229 [ https://substack.com/redirect/a98a08e9-8ba8-476f-8af1-f18492002155?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Negotiation Made Simple: A Practical Guide for Solving Problems, Building Relationships, and Delivering the Deal: https://www.amazon.com/Negotiation-Made-Simple-Relationships-Delivering/dp/1400336325 [ https://substack.com/redirect/eeb5c611-54e1-49e7-8adb-cbd17967f617?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Radical Candor: Be a Kick-Ass Boss Without Losing Your Humanity: https://www.amazon.com/Radical-Candor-Kick-Ass-Without-Humanity/dp/1250103509 [ https://substack.com/redirect/3780fe95-c67c-4776-90a6-30b8e94f6dff?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• High Output Management: https://www.amazon.com/High-Output-Management-Andrew-Grove/dp/0679762884 [ https://substack.com/redirect/346dcdfd-4be8-4237-b6a3-d6f1fde5828f?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• How to Win Friends and Influence People: https://www.amazon.com/How-Win-Friends-Influence-People/dp/0671027034 [ https://substack.com/redirect/5a7c6254-098f-4e79-97bf-aecb979c9054?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Production and marketing by https://penname.co/ [ https://substack.com/redirect/4c93a968-ebdc-4713-b47f-de56512e7a45?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com [ mailto:podcast@lennyrachitsky.com ].
Lenny may be an investor in the companies discussed.
My biggest takeaways from this conversation:...
Unsubscribe https://substack.com/redirect/2/eyJlIjoiaHR0cHM6Ly93d3cubGVubnlzbmV3c2xldHRlci5jb20vYWN0aW9uL2Rpc2FibGVfZW1haWw_dG9rZW49ZXlKMWMyVnlYMmxrSWpvME1qWTFNVFV3TkRBc0luQnZjM1JmYVdRaU9qRTRPVGM0TnpZNU5Td2lhV0YwSWpveE56Y3pOVGM0T0RReUxDSmxlSEFpT2pFNE1EVXhNVFE0TkRJc0ltbHpjeUk2SW5CMVlpMHhNRGcwTlNJc0luTjFZaUk2SW1ScGMyRmliR1ZmWlcxaGFXd2lmUS5XaTFyc1AxbkdxaUdqZkFwcDVMNmxrS3ZtU3dtZXJ5YWtnZDNaTWJCdm1VIiwicCI6MTg5Nzg3Njk1LCJzIjoxMDg0NSwiZiI6dHJ1ZSwidSI6NDI2NTE1MDQwLCJpYXQiOjE3NzM1Nzg4NDIsImV4cCI6MjA4OTE1NDg0MiwiaXNzIjoicHViLTAiLCJzdWIiOiJsaW5rLXJlZGlyZWN0In0.pzh-WYAG8lcn2X0zja3r74MADhrOKmkJbZ5ulTnd44c?
View Email
The tactical playbook for getting 20-40% more comp (without sounding greedy) | Jacob Warwick (Executive Negotiator)
lenny@substack.com3/15/2026
SubstackView this post on the web at https://www.lennysnewsletter.com/p/how-i-built-a-1m-subscriber-newsletter
People have been asking me to sit on the other side of the mic for a long time. With my wife’s debut children’s book, Charts for Babies, coming out next month, we figured: why not do it together? What followed was one of the most honest conversations I’ve had on this podcast. Michelle asked things no one else would think to ask—and many things I’ve never shared publicly. You’ll hear about the specific moments that pushed me to start the newsletter, how I think about quality and iteration, what most stresses me out, and the scariest moment of my life. This was so fun, and so special, and I hope you like it.
Pre-order Charts for Babies: https://www.amazon.com/Charts-Babies-Picture-Book/dp/1419785184 [ https://substack.com/redirect/b141a016-d352-4a25-9670-31521539539b?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Listen on YouTube [ https://substack.com/redirect/e3b34ff0-78f7-4249-a4bc-ec2df3144a6a?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], Spotify [ https://substack.com/redirect/95b2b823-7c46-43d3-b3dd-6c3b53535d39?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], and Apple Podcasts [ https://substack.com/redirect/92f79e52-18cd-4cbc-a3fa-e646a58940fc?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
We discuss:
The collection of moments that led me to what I do now
When I added a paywall, and how I knew it was working
The hidden treadmill behind shipping a newsletter post and podcast episode every week
The most stressful moments I’ve had in business and in life
How I think about stress, consistency, and keeping the business small
Brought to you by:
WorkOS [ https://substack.com/redirect/ca4f6e5a-4df8-4522-8b35-d28829fd4aad?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]—Modern identity platform for B2B SaaS, free up to 1 million MAUs
Metaview [ https://substack.com/redirect/bfa88c17-8fc6-4991-91b5-dc6eabb95515?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]—The AI platform for recruiting
DX [ https://substack.com/redirect/101c911a-3580-4a9d-a82d-e5a7155184f4?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]—The developer intelligence platform designed by leading researchers
Where to find Michelle Rial:
• X: https://x.com/TheRialMichelle [ https://substack.com/redirect/224e6170-3cab-43ff-a31b-9b88c55e350b?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• LinkedIn: https://www.linkedin.com/in/michellerial [ https://substack.com/redirect/cb12aacb-1472-44cb-8626-9a1ca7e29c4d?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Website: https://www.michellerial.com [ https://substack.com/redirect/bc532601-06e9-4823-9db8-893478cc382c?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Referenced:
• What Seven Years at Airbnb Taught Me About Building a Business: https://www.lennysnewsletter.com/p/what-seven-years-at-airbnb-taught [ https://substack.com/redirect/8c56d43e-d6b6-454c-8b06-459d9c91975d?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• How to Make a Living as an Artist: https://essays.fnnch.com/make-a-living [ https://substack.com/redirect/a7872195-1650-4e5a-92f3-8ff06dd98788?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Indiana Jones: https://en.wikipedia.org/wiki/Indiana_Jones [ https://substack.com/redirect/91b481e3-a931-4ed4-b636-3fea0c46ccb6?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Joshua Tree National Park: https://en.wikipedia.org/wiki/Joshua_Tree_National_Park [ https://substack.com/redirect/9c4b4f4e-e40d-4f3d-aeb6-5036c14b6538?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Authentic Happiness: https://www.authentichappiness.sas.upenn.edu [ https://substack.com/redirect/733fc81b-ff3e-4b2a-bef1-8376525ef72f?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Misophonia: https://my.clevelandclinic.org/health/diseases/24460-misophonia [ https://substack.com/redirect/1777b25d-85af-4b96-a6d3-a6e9c9d76db8?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Head of Claude Code: What happens after coding is solved | Boris Cherny: https://www.lennysnewsletter.com/p/head-of-claude-code-what-happens [ https://substack.com/redirect/b6dfe6a2-47bd-45ae-96c5-f44f6eae6947?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• The Devil Wears Prada: https://en.wikipedia.org/wiki/The_Devil_Wears_Prada_(film) [ https://substack.com/redirect/a761f9f3-70de-4308-a180-37555ea9c747?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Emily Charlton: https://devil-wears-prada.fandom.com/wiki/Emily_Charlton [ https://substack.com/redirect/66ba1994-7223-480f-837f-45622f719f11?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• When Harry Met Sally: https://en.wikipedia.org/wiki/When_Harry_Met_Sally… [ https://substack.com/redirect/a6345e22-af6e-431a-aa00-ddb7fdb5ef4d?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• xkcd: Ballmer Peak: https://xkcd.com/323 [ https://substack.com/redirect/833d302b-6a74-4d20-a1f9-d9b33d3edbdf?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• How Long Can I Call My Baby a Baby?: https://cupofjo.com/2026/02/27/how-long-can-i-call-my-baby-a-baby [ https://substack.com/redirect/a90a0859-4796-4440-a47a-deb47a52da06?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Recommended books:
• Am I Overthinking This?: Over-Answering Life’s Questions in 101 Charts: https://www.amazon.com/Am-Overthinking-This-Over-answering-questions/dp/1452175861 [ https://substack.com/redirect/fe78fb1f-cd80-4e6d-8535-2b1dfcf9399f?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Charts for Babies: A Picture Book: https://www.amazon.com/Charts-Babies-Picture-Book/dp/1419785184 [ https://substack.com/redirect/b141a016-d352-4a25-9670-31521539539b?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Maybe This Will Help: How to Feel Better when Things Stay the Same: https://www.amazon.com/Maybe-This-Will-Help-Better/dp/1797211250 [ https://substack.com/redirect/b7ed3e22-bd19-474b-a513-d6251230fdb0?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Jon Klassen books: https://www.amazon.com/stores/author/B00MXOB18Q?ccs_id=9e2a2952-ae68-4b1b-ae95-8ed471bd8e75 [ https://substack.com/redirect/66ab8c40-9c28-41e4-9376-7e1586c2b38c?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• I Want My Hat Back: https://www.amazon.com/I-Want-My-Hat-Back/dp/0763655988 [ https://substack.com/redirect/018be644-0ab3-4b42-85fa-9aefe5486acd?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Production and marketing by https://penname.co/ [ https://substack.com/redirect/7b5c6786-0058-49e8-94c5-80b226cbd3a3?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com [ mailto:podcast@lennyrachitsky.com ].
Lenny may be an investor in the companies discussed.
My biggest takeaways from this conversation:...
Unsubscribe https://substack.com/redirect/2/eyJlIjoiaHR0cHM6Ly93d3cubGVubnlzbmV3c2xldHRlci5jb20vYWN0aW9uL2Rpc2FibGVfZW1haWw_dG9rZW49ZXlKMWMyVnlYMmxrSWpvME1qWTFNVFV3TkRBc0luQnZjM1JmYVdRaU9qRTRPVGt4TlRVd055d2lhV0YwSWpveE56Y3pNekU1TlRVekxDSmxlSEFpT2pFNE1EUTROVFUxTlRNc0ltbHpjeUk2SW5CMVlpMHhNRGcwTlNJc0luTjFZaUk2SW1ScGMyRmliR1ZmWlcxaGFXd2lmUS5NYnFjNEhmVFppRVZJOXAydkFvT1QtV3JLUFVyVUZnclhJSHdWQkhlLTlRIiwicCI6MTg5OTE1NTA3LCJzIjoxMDg0NSwiZiI6dHJ1ZSwidSI6NDI2NTE1MDQwLCJpYXQiOjE3NzMzMTk1NTMsImV4cCI6MjA4ODg5NTU1MywiaXNzIjoicHViLTAiLCJzdWIiOiJsaW5rLXJlZGlyZWN0In0.uLd0BEkwrfGwNLaJpPlU_9aWfauULXlpZ1_yGd0gmjc?
View Email
How I built a 1M+ subscriber newsletter and top 10 tech podcast | Lenny Rachitsky
lenny@substack.com3/12/2026
SubstackView this post on the web at https://www.lennysnewsletter.com/p/a-guide-to-advanced-b2b-positioning
👋 Hey there, I’m Lenny. Each week, I answer reader questions about building product, driving growth, and accelerating your career. For more: Lenny’s Podcast [ https://substack.com/redirect/c3fc865f-d4f4-4cde-8007-6af7979c42c7?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] | Lennybot [ https://substack.com/redirect/404b252a-e778-42b6-9ab0-e8ef2702a1dc?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] | How I AI [ https://substack.com/redirect/36788c30-6861-49a3-942c-5dfdba47c170?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] | My favorite AI/PM courses [ https://substack.com/redirect/116c6184-5f14-4024-b340-441b68440820?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], public speaking course [ https://substack.com/redirect/974f4069-021e-4df1-acd6-60ff8977c6c3?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], and interview prep copilot [ https://substack.com/redirect/1b1f8164-7717-4d6f-a233-f2561a023091?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
P.S. Get a full free year of Lovable, Replit, Manus, Gamma, n8n, Canva, ElevenLabs, Amp, Factory, Devin, Bolt, Wispr Flow, Linear, PostHog, Framer, Railway, Granola, Warp, Perplexity, Magic Patterns, Mobbin, ChatPRD, and Stripe Atlas by becoming an Insider subscriber [ https://substack.com/redirect/097ae1f4-8a97-46b1-981a-caaec80dfb46?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]. Yes, this is for real [ https://substack.com/redirect/c8d30141-d628-4df6-bf8c-ecd051fd8abd?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ].
As AI makes it trivial to build and launch products (and, soon, even come up with product ideas), the biggest challenge for product teams is quickly becoming distribution: getting people to pay attention to your product in the increasing cacophony of launches.
One of the most powerful tools to cut through that noise is positioning. Strong, specific positioning grabs people’s attention and helps them instantly understand why your product is for them.
April Dunford [ https://substack.com/redirect/b6f41eac-394b-4141-882e-20e9668f9141?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] is the world’s leading expert on the topic. She is the author of the book on positioning, Obviously Awesome [ https://substack.com/redirect/e8bfb98c-849d-40f6-adc0-4b44032043eb?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], and has worked with over 300 B2B companies to nail their positioning. She’s also a two-time Lenny’s guest contributor and podcast guest. As she explained in her previous, widely shared, guest post [ https://substack.com/redirect/8fe986ac-d3d8-4545-8374-e03191c9c4d8?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], “a single shift in positioning can mean the difference between a product that flops and one that breaks through.”
In her latest guest post, below, April offers a guide to advanced B2B positioning—four lessons for getting past the trickiest and most common roadblocks that teams run into.
Let’s get into it.
P.S. April just published an updated and expanded edition of Obviously Awesome [ https://substack.com/redirect/e8bfb98c-849d-40f6-adc0-4b44032043eb?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]. Grab a copy if you know what’s good for you. For more from April, subscribe to her excellent Substack [ https://substack.com/redirect/4cb827b7-3f6f-4433-a3be-271c6c8e70e1?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] (she’ll be dropping some new plug-and-play positioning templates in the next couple of weeks), and follow her on LinkedIn [ https://substack.com/redirect/a468a024-b195-413f-8af7-b91066292774?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ].
You can also listen to this post in convenient podcast form: Spotify [ https://substack.com/redirect/1528098d-963f-4a88-a487-a00f439cbc91?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] / Apple [ https://substack.com/redirect/558331ee-d6ae-49c5-9545-111522f97ab6?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] / YouTube [ https://substack.com/redirect/bde64022-920f-40a0-bfa4-caef1c7f2b1e?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ].
When I started out as a junior product marketer, positioning was something everyone understood but no one knew how to do, especially for tech companies. My work over the past 10 years has focused on developing a repeatable process that any B2B technology company can use as a starting point for creating strong positioning. I wrote a book, Obviously Awesome, about how a cross-functional team should work through the five components of positioning in a specific order. I’ve also covered it in this article [ https://substack.com/redirect/8fe986ac-d3d8-4545-8374-e03191c9c4d8?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] and this podcast [ https://substack.com/redirect/dddc3ab2-bebd-41e0-b246-af670d2939ad?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] with Lenny.
Today, we have a much deeper understanding of how to develop good positioning—which is great for product marketers and great for the industry. But teams may encounter more advanced and challenging roadblocks that can slow momentum, derail collaboration, and break a project entirely. In this post, I’m looking beyond the basics of running a positioning process to address how to get past difficult roadblocks at different stages of the positioning development process to develop a positioning that clearly sets your product apart from your competition.
There are four patterns I see where teams encounter roadblocks during positioning development that are hard to see coming and to navigate around:
Disagreement about what to position against
Product pessimism blinds the team to product strengths
The differentiated value is poorly defined
The company doesn’t know what they are positioning
These roadblocks are common, but they’re far from impossible to manage. In this post, I’ll give you a clear view of where they may appear down the road and how you can avoid them entirely or guide your team safely around them to achieve consistent, lasting success in your B2B positioning. You’ll walk away with a greater understanding of the positioning process and four real-world strategies that you can immediately take into your next project. Now let’s get into it.
Four positioning roadblocks and how to move past them
Roadblock 1: Disagreement about what to position against
The first step in a positioning process is to look at the competitive alternatives. One of the most surprising things I have seen in positioning work is how often marketing, product, sales, and the founder/CEO have very different views on who they compete with. I’ve seen it so consistently that I believe disagreement about what to position against is the root of most weak positioning.
Each function in a B2B tech company tends to have its own set of biases when it comes to thinking about “competition.”
Marketing: Marketing is often overly influenced by a potential competitor’s marketing spend, regardless of the effectiveness of that spend (which is often completely unknown). Marketing teams watch how competitors show up in media, online, ads, and at conferences, and then often equate market visibility with competitive success—even if the sales team rarely encounters this competitor on a prospect’s short list and never loses deals to them.
Product Management: The product team is focused a little further into the future than the marketing and sales teams. Product roadmap work requires an understanding of what I would call “horizon competitors,” products that aren’t causing any pain today but could in the future. In a positioning exercise, product teams will often list twice as many “competitors” as a sales team does, many of which are never seen on a prospect’s short list.
Sales: Sales teams can have a skewed perception of competitors in two distinct ways. Firstly, they tend to have what I would call a “whale” bias. Sales can feel the sting of losing one very big deal and become overly focused on that winning competitor, even if they are never seen in more “normal” deals. The second bias is that they rarely define the status quo solution as a “competitor.” Deals lost to the status quo are often categorized as “no decision.” In the mind of a good salesperson, the customer’s “No” is mentally translated to “Not yet.” I have seen this even when the overwhelming majority of deals are lost to the status quo.
Founders: Most founders I’ve worked with have a great gut feel for positioning. In fact, many positioning exercises I’ve led end up helping newer executives understand the nuances of what the founder already knows. However, in certain situations, founders might muddy the positioning waters by bringing a bias that the rest of the team doesn’t fully understand. Three situations where I see this happening:
The founder was once heavily involved in closing deals but became less so. The founder may be biased toward what the competitive landscape used to look like and less familiar with current market dynamics.
Recent acquisitions have opened opportunities in market segments that the acquiring team (including the founder) may not understand as well as the folks on the recently acquired team.
The founder has recently been very focused on fundraising. In fundraising, the company orients more toward the future state it is building. Often, that future state is not something the sales team can sell today. Too much focus on future capabilities the company does not yet deliver can result in stalled deals and customers saying, “We love that. Come back in two years when you have it.”
The solution: Focus on the prospect’s view of the competition
The prospect’s view of competitive alternatives is the only one that matters. Because different teams interact with customers in different ways and at different points in the sales process, their understanding of how customers view alternatives won’t always align. If we go into the positioning process understanding this, we can get past the roadblock in these ways:
Imagine a world from the prospect’s POV: Rather than have the team list conflicting sets of perceived competitors, ask, “If we didn’t exist, what would a prospect do?” That reframing helps the team focus on what is happening in sales deals out in the real world, rather than who they should or could compete with.
Stay rooted in the near term: As an old boss of mine used to say, “We have to sell what’s on the truck.” The path to success is to focus on the product as it exists, in the market as it exists, and selling to the customers we can win with today. We should expect our positioning to change over time as the product, competitors, and target customers evolve, but we should also accept that we are terrible at predicting how the changes will unfold.
Don’t forget the status quo: In B2B, vendors typically lose about half their sales opportunities to whatever the prospect is currently using. I’ve worked with companies where that number exceeds 80%. We need to understand the strengths and weaknesses of the status quo solution to convince buyers to move on. Research shows that about half the time, a status quo decision is more about customer indecision than a vote for the status quo solution (see Matt Dixon’s JOLT Effect research, for example). Still, we ignore the other half at our peril. Strong positioning wins both types of “no decision” deals.
Work with a cross-functional team: The first and most obvious way to ensure that the positioning accounts for different perspectives is to work with a cross-functional team. My recommendation is that we have the heads of marketing, sales, product management, and customer success, along with the founder, CEO, or head of the business (if it is a larger company). Often it helps to include a couple of very experienced account executives from the sales team to verify what is happening in the early sales stages. If we are positioning the company or a grouping of products (more on this later), we will need to make sure we have folks with product and commercial experience for each product. We might also need sales representation across different geographies if the competitive landscape varies.
Roadblock 2: Pessimism blinds the team to the products’ strengths
Some companies suffer from overly pessimistic product thinking—where teams convince themselves their product is an undifferentiated loser despite clear evidence that they’re winning in parts of the market. This can happen when teams are overly focused on closing perceived gaps with competitors or when product teams and sales teams don’t communicate well or often. The pessimism pattern is dangerous because it blinds teams to their competitive strengths and prevents the company from positioning around them. Also, this mindset tends to be contagious, spreading to marketing and sales teams, who may lose confidence in the product’s ability to deliver differentiated value. It’s hard to convince prospects to invest in a product that sellers don’t believe in.
The pessimism manifests in four key ways:
Defining ideal customers so broadly that every lost deal seems like a product failure: I have worked with companies where product teams become over-exposed to bad deals and under-exposed to good ones. PMs get pulled in to try to save lost-cause deals, even when the prospect was a poor fit for the product in the first place. Meanwhile, deals with good-fit prospects are easily closed without any PM involvement. The result is that the product team begins to develop a skewed idea of what a good-fit prospect typically looks like.
Maintaining long hypothetical competitor lists: It’s hard to differentiate your product from an overly long list of competitors, particularly when we know little about many of them because we have never had to compete against them in a deal. For roadmap work, it makes sense to track future potential competitors. For positioning work, we have to stay oriented in the reality of the market—and be prepared to shift if and when a competitor begins to truly cause us pain.
Dismissing sales team insights about why customers buy: Sometimes this type of pessimism persists even in the face of proof that the product is doing well. In one workshop, a sales team listed a set of large accounts they had won because the product was superior in a particular way. The product team insisted that those prospects had failed to evaluate the other alternative properly. In another, despite the company generating hundreds of millions in revenue with solid growth, the product leader insisted that the sales team was winning through trickery and lies. I have seen salespeople who went too far in stretching the truth, but never one who was very successful with that strategy.
Viewing the role of product management as “problem identification” rather than architecting true differentiated value: Some companies get trapped in a cycle of competitive catch-up, to the point where the team becomes very adept at pointing out product problems and less attuned to where the product is leading. Often, there is a big, boring, long-standing differentiator hiding in plain sight. The product team takes it for granted (“Oh, we have always done that!”) while sales are selling the heck out of it.
Each symptom reinforces the others, creating a toxic cycle that undermines the company’s ability to articulate and amplify its genuine competitive advantages.
The solution: Keep coming back to what’s working
To break the pattern for positioning work, expose the product team to what sales understands about what’s working in the majority of deals, and work through a positioning exercise to help both teams understand each other.
We can get past this roadblock by:
Focusing the whole team on strengths and the near-term competitive advantage: A positioning process is really about finding the heart of why we win. To get there, we need to understand the product’s strengths and competitive advantages. We understand the product isn’t perfect and that we have competitive gaps. But we need to win business now, and we need positioning that tells a clear, compelling story about the product we have today (with the full understanding that that positioning will change and hopefully improve over time). Positioning is not a product strategy, nor does it set the product’s future direction. A discussion of the ways the product falls short does not lead to strong, differentiated positioning.
Including experienced sales voices in the room: Nobody understands how a customer behaves across a sales process better than your sales team does. For positioning work, we need to rely on that experience to understand who our true competitors are, what our true differentiators are, and which types of buyers care most about those differentiators. If the company’s CRO and VP of Sales do not have much experience with early-stage deals, it helps to have an experienced account executive in the room, and having two is generally better than just one, giving us a view across a broader set of deals.
Preparing the moderator to challenge participants: If you do a group positioning exercise, choose your moderator carefully. An experienced moderator can help the team stay grounded in reality and should be prepared to challenge participants if they become overly pessimistic. The moderator should remind the team that every day, customers spend months evaluating their options and then selecting the product. These customers can’t all be careless, gullible shoppers. Similarly, if a participant claims that many deals are won for a particular reason, they should be prompted to provide evidence and details. The team needs to agree on a position to work together and make it stick after the exercise.
It’s not unusual for teams to get together to discuss product problems and gaps. However, a positioning exercise should focus on where the product outperforms the competition. Getting the team oriented around the differentiated strengths of the product is critical for great positioning.
Roadblock 3: The differentiated value is poorly defined
As vendors (and particularly product folks), it’s easy to focus on features and assume buyers will easily understand why those features matter. In my experience, a product’s most differentiated capabilities are often the most difficult for prospects to understand, precisely because they are uncommon. If we really want to answer the question “Why pick us over the alternatives?” We have to clearly articulate the value our product can deliver that other alternatives cannot. This step in the process is the one I see teams struggle with the most.
There are four ways I see teams get stuck around differentiated value:
Assuming prospects understand why a feature is important: Today, a smartphone vendor can simply advertise that their phone has a 50-megapixel camera, and the audience knows what that means. However, 20 years ago, when few people had experience with digital cameras, you would have had to explain what a megapixel was, why anyone should care, and why 50 is better than 20. The more unique a feature is, the less likely a potential customer is to understand why it is important.
Stopping short of capturing value the prospect actually understands: I once worked for a database company with patented technology that enabled us to execute a specific type of query 1,000 times as fast as our competitors. We assumed anyone buying a database would find query speed valuable. Interestingly, many companies did not care. They were running the query for a monthly or quarterly report, so getting the answer in a day or two was perfectly fine. Our best-fit accounts, however, were running those types of queries to respond to a customer question. The real value lay in responding to customers more quickly, not executing the query faster. Recently, many of the teams I’ve worked with have a value point around efficiency. But their buyers may be much more focused on driving revenue—and can’t connect the dots between efficiency and revenue themselves.
Going too far and losing the differentiation completely: In B2B, we really only have two “pure” points of value. We are helping businesses make money or save money. (Insurance folks would add reducing risk, but that one is a special case!) Unlike consumer products, a successful B2B software project isn’t going to get you a date or make you look rich. We are increasing revenue or decreasing costs, and that’s it. If you abstract the value of your product all the way down to “This product saves you money,” you will sound exactly like every other product you compete with.
Overwhelming customers by attempting to communicate too many differentiated value themes: Differentiated value should succinctly answer the question “Why pick us over the alternatives?” If we give prospects a list of 10 reasons why, they aren’t likely to connect with a clear story or remember more than a couple of them (if we’re lucky).
Confusing differentiated value with sales objection handling: If there are people on the team who have never worked in sales, they might not understand what a sales objection is or how it differs from value. Value is a reason to buy. An objection is a reason a prospect might not buy, even if the value is something they really want. Often, objections come from constituents who are not the deal champion but can kill a deal if they have specific problems with the product. For example, I worked with a company whose product was very easy for the IT team to manage, which gave them an advantage over many competitors and the status quo. However, the purchase decision was driven by a business buyer who didn’t see any value in ease of management. In this case, ease of management was only used to handle the potential objection of the IT department after the business champion had selected the product.
The solution: Home in on the “so what?”...
Unsubscribe https://substack.com/redirect/2/eyJlIjoiaHR0cHM6Ly93d3cubGVubnlzbmV3c2xldHRlci5jb20vYWN0aW9uL2Rpc2FibGVfZW1haWw_dG9rZW49ZXlKMWMyVnlYMmxrSWpvME1qWTFNVFV3TkRBc0luQnZjM1JmYVdRaU9qRTRPVGt3TnpNd01Td2lhV0YwSWpveE56Y3pNVFEzTlRBNUxDSmxlSEFpT2pFNE1EUTJPRE0xTURrc0ltbHpjeUk2SW5CMVlpMHhNRGcwTlNJc0luTjFZaUk2SW1ScGMyRmliR1ZmWlcxaGFXd2lmUS5NNHpVT20yXzBHZktvZHhINmQ4RkZLc0FaQ0lrekdLYXowOFNBZ1F3UzZFIiwicCI6MTg5OTA3MzAxLCJzIjoxMDg0NSwiZiI6dHJ1ZSwidSI6NDI2NTE1MDQwLCJpYXQiOjE3NzMxNDc1MDksImV4cCI6MjA4ODcyMzUwOSwiaXNzIjoicHViLTAiLCJzdWIiOiJsaW5rLXJlZGlyZWN0In0.zHXoOipYHO6w_4s_WdHS0tCYoJ3Zhb_hZSDwtm2-Eck?
View Email
A guide to advanced B2B positioning
lenny@substack.com3/10/2026
SubstackView this post on the web at https://www.lennysnewsletter.com/p/the-most-successful-ai-company-youve-never-heard-of
Qasar Younis is the co-founder and CEO of Applied Intuition, a $15 billion AI company that adds intelligence to cars, tractors, planes, submarines, and other vehicles—essentially, Tesla or Waymo without the hardware. He was previously COO of Y Combinator, started his career as an engineer at GM and Bosch, and was born on a farm in Pakistan.
Listen on YouTube [ https://substack.com/redirect/e125cf46-b87d-4166-a1d9-727b02dff3d2?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], Spotify [ https://substack.com/redirect/b2188a17-705f-4f36-8b3e-14d9c627f208?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], and Apple Podcasts [ https://substack.com/redirect/9a9eda04-1687-4fc1-a00f-dff3339ae0c7?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
We discuss:
Why the biggest AI revolution will play out in mining, farming, construction, and trucking over the next 5 to 10 years, not in software
Why Qasar intentionally stayed under the radar for nearly a decade while building Applied Intuition, and why most founders shouldn’t do that
The truth about China’s AI capabilities and why comparisons to American companies are fundamentally flawed
The company values that drive Applied Intuition: speed above everything, laugh a lot, half the work is follow-up, never disappoint the customer
The biggest lessons from Qasar’s stint as YC’s COO, including that the most successful companies show traction very early
How reading old books is the best way to build taste
Brought to you by:
Omni [ https://substack.com/redirect/75551a9a-ceed-4644-b170-2b0ceb3d15e9?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]—AI analytics your customers can trust
Vanta [ https://substack.com/redirect/6ef442de-02ed-4d68-bad5-c8bd1a14c0e6?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]—Automate compliance. Simplify security.
Lovable [ https://substack.com/redirect/40356a0e-113d-44e1-81ae-8e7321a498ba?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]—Build apps by simply chatting with AI
Where to find Qasar Younis:
• X: https://x.com/qasar [ https://substack.com/redirect/4fd8a6eb-5974-4d5a-a3aa-aff9649937aa?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• LinkedIn: https://www.linkedin.com/in/qasar [ https://substack.com/redirect/57d6fa24-cd57-49d1-9cb1-6573e03a956d?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Website: https://qy.co [ https://substack.com/redirect/ff2ea019-1d06-4968-9b90-c5e8604a1c23?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Reading list: https://qy.co/books [ https://substack.com/redirect/ac3a0a63-2050-4f7f-8dd8-f8c2f4ea2a6d?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Referenced:
• Applied Intuition: https://www.appliedintuition.com [ https://substack.com/redirect/f7f56221-0459-4016-8e11-53301e1a555b?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Marc Andreessen: The real AI boom hasn’t even started yet: https://www.lennysnewsletter.com/p/marc-andreessen-the-real-ai-boom [ https://substack.com/redirect/c318d6b8-8a08-4311-8aa2-0dc109a82b5b?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Elad Gil’s website: https://eladgil.com [ https://substack.com/redirect/503cf54f-eb0b-41b1-be10-15f3ef81230e?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Bosch: https://www.bosch.com [ https://substack.com/redirect/6bd6bf59-ff69-46b5-a0cd-c73e7652b0bd?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Berkshire Hathaway: https://www.berkshirehathaway.com [ https://substack.com/redirect/aaec1879-5574-4480-829b-027bd70d16d1?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Naval Ravikant on X: https://x.com/naval [ https://substack.com/redirect/11374839-7bd6-4052-868f-f827cd264bb5?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Y Combinator: https://www.ycombinator.com [ https://substack.com/redirect/a7e13a06-d277-4be5-a601-abe7356e69e2?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Waymo: https://waymo.com/ [ https://substack.com/redirect/26986818-5e43-4b1c-8750-3831f4b3d593?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Tesla: https://www.tesla.com [ https://substack.com/redirect/147258d2-acc9-4597-a35e-eb97847aa2dc?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• DeepSeek: https://www.deepseek.com [ https://substack.com/redirect/21fe0ed3-e783-45b8-92bb-7b17e5f5e5ad?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Rivian: https://rivian.com [ https://substack.com/redirect/2401ce59-55b8-4a6a-b2fc-8ad078ff8faa?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Crate & Barrel: https://www.crateandbarrel.com [ https://substack.com/redirect/7a53a449-438d-457a-9622-668371750b85?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• OpenClaw: https://openclaw.ai [ https://substack.com/redirect/8a1cda00-b64b-4145-96d4-5a0037a29877?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Sam Altman on X: https://x.com/sama [ https://substack.com/redirect/8c6607c1-7cdc-4544-82e4-1487f00d918d?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Peter Ludwig on LinkedIn: https://www.linkedin.com/in/peterwludwig [ https://substack.com/redirect/4c9c654d-7afc-4114-81b1-d6837c7ebd51?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• What Steve Jobs really meant when he said ‘Good artists copy; great artists steal’: https://www.cnet.com/tech/tech-industry/what-steve-jobs-really-meant-when-he-said-good-artists-copy-great-artists-steal [ https://substack.com/redirect/ae70a03f-4fd6-45b7-9852-2033a8b2d776?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• 7 quotes on the power of reading from Charlie Munger: https://www.neil.blog/articles/7-quotes-power-reading-charlie-munger [ https://substack.com/redirect/ce0d2e73-fff4-46b3-87ee-ef3ec54384a6?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Andreessen Horowitz: https://a16z.com [ https://substack.com/redirect/89efb428-b208-4086-b51c-fdce234603b3?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• John Doerr on LinkedIn: https://www.linkedin.com/in/john-doerr-03248211 [ https://substack.com/redirect/f46b6b05-e3b5-4bb3-9de1-a108b8188827?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Gandhi’s quote: https://www.azquotes.com/author/5308-Mahatma_Gandhi/tag/truth#google_vignette [ https://substack.com/redirect/3d56badc-1bae-4cd2-afdf-af61fcbdbdc1?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Steve Ballmer on X: https://x.com/Steven_Ballmer [ https://substack.com/redirect/198c0a39-048a-4f1c-9f42-7c71ecb6c787?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• General Motors: https://www.gm.com [ https://substack.com/redirect/c16443b3-743e-4581-bccd-9c84645dee7b?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Recommended books:
• House of Huawei: The Secret History of China’s Most Powerful Company: https://www.amazon.com/House-Huawei-History-Powerful-Company/dp/0593544633 [ https://substack.com/redirect/bfa3d574-8cde-492e-bfad-30eb13bab556?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Maintenance: Of Everything, Part One: https://press.stripe.com/maintenance-part-one [ https://substack.com/redirect/db3f2723-21ba-451b-8140-741864f444a7?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• The Autobiography of Malcolm X: As Told to Alex Haley: https://www.amazon.com/Autobiography-Malcolm-Told-Alex-Haley/dp/0345350685 [ https://substack.com/redirect/e1519a77-8f3b-413d-a7fc-1ce4edfa21ea?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• High Output Management: https://www.amazon.com/High-Output-Management-Andrew-Grove/dp/0679762884 [ https://substack.com/redirect/fd9d6137-f3bf-4cb3-9db6-4b187ae08cc7?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• The Emperor of All Maladies: A Biography of Cancer: https://www.amazon.com/Emperor-All-Maladies-Biography-Cancer/dp/1439170916 [ https://substack.com/redirect/972743b5-1176-45e6-adf2-41e04aca46c3?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Made in America: https://www.amazon.com/Sam-Walton-Made-America/dp/0553562835 [ https://substack.com/redirect/4fa3d8e3-c7da-45ca-974d-6e54b3a9ebfe?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• My American Journey: https://www.amazon.com/American-Journey-Autobiography-Colin-Powell/dp/0679432965 [ https://substack.com/redirect/d74dc78e-8880-4e73-9fa3-89cb49c3bd8d?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Guns, Germs, and Steel: The Fates of Human Societies: https://www.amazon.com/Guns-Germs-Steel-Fates-Societies/dp/0393317552 [ https://substack.com/redirect/d2203bb9-fd13-4366-86ac-e33996e0f116?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Collapse: How Societies Choose to Fail or Succeed: https://www.amazon.com/Collapse-Societies-Choose-Succeed-Revised/dp/0143117009 [ https://substack.com/redirect/41329230-8375-475d-90e3-4543a80a1a85?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• SPQR: A History of Ancient Rome: https://www.amazon.com/SPQR-History-Ancient-Mary-Beard/dp/0871404230 [ https://substack.com/redirect/a8e1fc47-5ded-4d3c-ae29-7a85ced0aca3?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• A World Appears: A Journey into Consciousness: https://www.amazon.com/World-Appears-Journey-into-Consciousness/dp/198488199X [ https://substack.com/redirect/90343885-1e80-4806-87a4-9b5b452fab51?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Production and marketing by https://penname.co/ [ https://substack.com/redirect/11b727f8-8384-4b3b-afec-570e6344f22f?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com [ mailto:podcast@lennyrachitsky.com ].
Lenny may be an investor in the companies discussed.
My biggest takeaways from this conversation:...
Unsubscribe https://substack.com/redirect/2/eyJlIjoiaHR0cHM6Ly93d3cubGVubnlzbmV3c2xldHRlci5jb20vYWN0aW9uL2Rpc2FibGVfZW1haWw_dG9rZW49ZXlKMWMyVnlYMmxrSWpvME1qWTFNVFV3TkRBc0luQnZjM1JmYVdRaU9qRTRPVFl4TlRBeE9Td2lhV0YwSWpveE56Y3lPVGN6T0RVNExDSmxlSEFpT2pFNE1EUTFNRGs0TlRnc0ltbHpjeUk2SW5CMVlpMHhNRGcwTlNJc0luTjFZaUk2SW1ScGMyRmliR1ZmWlcxaGFXd2lmUS5mcUxsUnZqdFAzUW9QX0hnVGtXZS1aeml6WlVPbE83NHFTMklBS1J3Z0pJIiwicCI6MTg5NjE1MDE5LCJzIjoxMDg0NSwiZiI6dHJ1ZSwidSI6NDI2NTE1MDQwLCJpYXQiOjE3NzI5NzM4NTgsImV4cCI6MjA4ODU0OTg1OCwiaXNzIjoicHViLTAiLCJzdWIiOiJsaW5rLXJlZGlyZWN0In0.MqaVTL8FOeAYS7aVzikMjSF_Sr1asFen7nd0nb6n31k?
View Email
The most successful AI company you’ve never heard of | Qasar Younis
lenny@substack.com3/8/2026
SubstackView this post on the web at https://www.lennysnewsletter.com/cp/189898375
Unsubscribe https://substack.com/redirect/2/eyJlIjoiaHR0cHM6Ly93d3cubGVubnlzbmV3c2xldHRlci5jb20vYWN0aW9uL2Rpc2FibGVfZW1haWw_dG9rZW49ZXlKMWMyVnlYMmxrSWpvME1qWTFNVFV3TkRBc0luQnZjM1JmYVdRaU9qRTRPVGc1T0RNM05Td2lhV0YwSWpveE56Y3lOalExTlRBM0xDSmxlSEFpT2pFNE1EUXhPREUxTURjc0ltbHpjeUk2SW5CMVlpMHhNRGcwTlNJc0luTjFZaUk2SW1ScGMyRmliR1ZmWlcxaGFXd2lmUS5jU19JcUxTU0ZoSG43UlZnZUlpanJvRjFHdUNjZC1GTnF3VEg3SFdKNjhNIiwicCI6MTg5ODk4Mzc1LCJzIjoxMDg0NSwiZiI6dHJ1ZSwidSI6NDI2NTE1MDQwLCJpYXQiOjE3NzI2NDU1MDcsImV4cCI6MjA4ODIyMTUwNywiaXNzIjoicHViLTAiLCJzdWIiOiJsaW5rLXJlZGlyZWN0In0.4XjKWxMc-GEg0rS6IlKsw-U18tzkOuHkRM8jLS6wXwA?
View Email
Three Job Searches, Three AI Roles: What Actually Worked
lenny@substack.com3/4/2026
SubstackView this post on the web at https://www.lennysnewsletter.com/p/how-to-debug-a-team-that-isnt-working
👋 Hey there, I’m Lenny. Each week, I answer reader questions about building product, driving growth, and accelerating your career. For more: Lenny’s Podcast [ https://substack.com/redirect/6a338125-411f-45a2-8163-7ff030a16d72?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] | Lennybot [ https://substack.com/redirect/8374b9f6-0328-4b89-ba32-bde7453d9437?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] | How I AI [ https://substack.com/redirect/8c8d650a-1784-4af7-baf1-7d2809f63457?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] | My favorite AI/PM courses [ https://substack.com/redirect/4270a849-93f1-4193-b9d0-82fdf1e41dc5?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], public speaking course [ https://substack.com/redirect/9578031d-8870-4f84-bffc-1423a4cb987f?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], and interview prep copilot [ https://substack.com/redirect/30c97ce3-6085-41ad-b4b4-73927b6d4dd3?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
P.S. Get a free full year of Lovable, Manus, Replit, Gamma, n8n, Canva, ElevenLabs, Amp, Factory, Devin, Bolt, Wispr Flow, Linear, PostHog, Framer, Railway, Granola, Warp, Perplexity, Magic Patterns, Mobbin, ChatPRD, and Stripe Atlas by becoming an Insider subscriber [ https://substack.com/redirect/806bc978-400b-421c-96e2-89b258fcc801?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]. Yes, this is for real.
Molly Graham [ https://substack.com/redirect/f4cc6ded-cb3d-4d48-9725-d317c5502a69?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] is the epitome of the type of person I love to collaborate with. She spent decades working closely with some of the most successful leaders in tech, including Mark Zuckerberg, Sheryl Sandberg, Chamath Palihapitiya, and Bret Taylor, and more recently (through her Glue Club [ https://substack.com/redirect/635a190b-62f3-46b1-8148-aa52eee0868f?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] community), she’s guided hundreds of leaders through the chaotic, lonely, and overwhelming journey inside early-stage and fast-growing companies. Drawing from these experiences, she is able to find patterns in what works and doesn’t and, more than anyone else I’ve met, is able to translate these lessons into powerful and memorable metaphors.
In her piece below, which I suspect will become as iconic as “Give Away Your Legos [ https://substack.com/redirect/068e63c0-88cc-47fd-8b87-b1b36b5eca48?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ],” she builds on our recent podcast conversation [ https://substack.com/redirect/010acf4f-e125-4bf1-a67f-dee3a78755a8?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] to unpack a management framework that will change how you tackle team challenges: the Waterline Model.
Let’s get into it.
For more from Molly, check out her Substack [ https://substack.com/redirect/819785ee-4909-496d-9f20-8084d73cf115?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] and LinkedIn [ https://substack.com/redirect/f4cc6ded-cb3d-4d48-9725-d317c5502a69?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], and her Glue Club [ https://substack.com/redirect/635a190b-62f3-46b1-8148-aa52eee0868f?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] community. You can listen to this post in convenient podcast form: Spotify [ https://substack.com/redirect/59c58e38-93be-490e-90f5-7206b5d946ee?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] / Apple [ https://substack.com/redirect/def70f25-6f18-4f2a-a789-431bb286c3cb?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] / YouTube [ https://substack.com/redirect/78d6e235-7d32-408e-b37f-b33e256b8b20?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ].
There’s a moment most leaders recognize. You’ve set a clear goal (or so you think), your team’s bought in (or so they say), yet timelines keep slipping, execution is messy, and you’re having the same conversations over and over. When that happens, it’s tempting to jump straight to people-based explanations: “This team just doesn’t work well together.” “That person isn’t strong enough.” “We need better execution.”
Sometimes that’s true. But after two decades of working inside companies like Google, Facebook, and the Chan Zuckerberg Initiative, and supporting leaders at companies like Stripe, Anthropic, OpenAI, Microsoft, and Gamma, I’ve come to believe that blaming people for problems that are actually structural is one of the biggest leadership traps there is.
I’ve learned to slow down in these moments and use a simple diagnostic tool I picked up early in my career: the Waterline Model.
I first learned how to use this tool when I was leading 75-day wilderness expeditions in Patagonia and Alaska for the National Outdoor Leadership School [ https://substack.com/redirect/506570c4-3a75-4592-be28-a41c33df9b11?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] at age 22. Out there, when a team isn’t working, things fall apart fast. People get cold, hungry, tired, scared. There’s no hiding behind process or politeness, and there’s definitely no time for vague diagnoses like “the vibe is off.” You have to identify the source of what’s disrupting the team—not just the symptoms—and fix it quickly.
We learned the Waterline Model as instructors and taught it as part of the curriculum to students. Since then, I’ve used it anytime a team is underperforming, missing goals, or struggling more than they should be. More than anything, it has helped me avoid misdiagnosing problems, cycling through people unnecessarily, and wasting time fixing the wrong thing. At its core, the Waterline Model is a way to diagnose where a problem is actually coming from before you decide what to do about it.
In this post, I’ll walk through the model and show you how to use it as a practical diagnostic tool when a team is underperforming. We’ll look at the four levels where problems tend to show up—structure, dynamics, interpersonal, and individual—and how to work through them in the right order. By the end, you should be better equipped to slow down in those “something’s off” moments, identify the real source of friction on a team, and fix the right problem instead of defaulting to people changes.
How the Waterline Model works
Here’s the basic picture. Imagine a boat moving across the water—that boat is your team. The boat’s destination is your goal: hitting a KPI, winning a major new customer, shipping a product. Sometimes the water is calm and the boat is moving forward smoothly. Other times, it feels like you’re rowing through a hurricane and no one can quite explain why.
When I use this model, I’m able to move beyond the natural human instinct to automatically blame the people. The Waterline Model helps me investigate one question: What’s going on below the surface that’s making things harder than they should be?
This model gives you four places to look, in order, and it comes with a memorable rule of thumb: snorkel before you scuba. Start at the top, always. Snorkeling means checking the shared systems first—goals, roles, and decision-making—before you start diagnosing personalities.
At the top, just below the surface, is structure. This is the stuff that helps people know what they’re doing, why they’re doing it, and how success is defined: vision, goals, context, expectations, role clarity, and org design. In my experience, this is where a huge percentage of issues on teams actually shows up.
The next layer is dynamics—how the team works together day-to-day. This is where I look at how decisions get made, how conflict shows up and gets resolved, and how information flows (or doesn’t). Even with clear goals and roles, teams can struggle here. Structure and dynamics are systems shared by everyone on the team, so you can most directly affect the collective team performance at these levels.
Below that is interpersonal—tension between two people, lack of trust, unresolved conflict, style clashes. These issues are real, but they’re often caused or amplified by problems higher up.
And at the very bottom is individual—what’s happening inside a single person: skill gaps, stress, confidence, values, life stuff.
All four layers matter. Any one of them can make the water choppy.
But the Waterline Model and “snorkel before you scuba” remind me to start with the issues that impact the most people—closest to the surface—and only go deeper once I’ve ruled things out. Before you decide someone is the issue, you need to know that structure and dynamics aren’t pushing them toward exactly the behavior you’re frustrated by.
Let’s walk through each level and use common examples of issues on underperforming teams to show how you can use the model.
Structure: the most common culprit
A few years ago, I was asked to take over a struggling marketing team: “Go figure out what this team actually does, and why we’re spending so much money without seeing results.”
The temptation in a situation like this is to diagnose the people—who is a high performer, who is dragging people down—but the Waterline Model has taught me to start by evaluating the structure. So instead, I asked each person on my new team how they would describe their role, what goals they thought the team was responsible for, and what numbers they believed they personally owned and were expected to move. Almost immediately, those questions surfaced structural issues.
The team’s answers were wildly inconsistent. Individuals had no idea what their goals were or which metric the team was responsible for. People defined their roles in ways that were far too narrow, or disconnected, to make sense. What leadership thought the team was responsible for, and how success was measured, were very different from how people understood their own jobs.
In this case, it was impossible to determine whether the individuals were the right fit, because they were operating inside a deeply broken structure. If I had automatically assumed people were the problem, I probably would have fired the whole team and started over again. And then I’d likely have ended up with the same issues all over again. But once I realized this was a structural problem, the fix was clear.
I started by re-clarifying the team’s mandate, the goals the team actually owned, individual role definitions, and what success looked like for each role. Only after that work was complete did it make sense to evaluate whether each individual was a good fit for their role.
That clarity surfaced a few real fit issues. But it also immediately improved performance for most of the team—simply because people finally knew what their job was and what was expected of them. People are often smart and motivated, but (to use the boat analogy) they’re rowing in different directions because the structure isn’t doing its job. Structural clarity alone often resolves more issues than you’d expect.
Dynamics: teams behaving rationally inside bad systems
Dynamics are the cultural norms you’ve built for how the team actually works together day-to-day. What’s experienced, not what’s written down. You can have clear goals and roles and still find yourself with decisions bottlenecked at the top, endless debate with no resolution, or constant confusion about who has input versus who actually decides.
As an example, one member in Glue Club [ https://substack.com/redirect/06ba61b8-9606-4aae-a4c4-54e7281e0151?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] came to us with a familiar story: “My founder is constantly frustrated that the team is moving more slowly than they want. But when people try to move quickly or ship things or make decisions, the founder swoops in and unmakes decisions at the last minute or second-guesses people’s judgment. It doesn’t feel safe to move quickly.”
This wasn’t a structure problem. Goals were clear, roles were defined, and, on paper, people had decision rights. But in practice, decisions weren’t stable. Work would move forward, then get reversed later. Context would change after the fact. People learned that even if they did what was asked, they could still be wrong.
The team adapted in a very rational way: They slowed down. They added extra layers of alignment. They escalated decisions that technically didn’t need to be escalated. They optimized for not being wrong instead of for progress.
From the outside, it looked like a performance problem. From the inside, it felt like self-protection. The dynamics of this team taught people that speed is risky, and that was the problem.
People adapt quickly to what’s rewarded, punished, tolerated, or ignored. Over time, the team learns how to survive inside the system a leader creates, whether implicit or explicit. Dynamics problems show up when a team’s behavior makes sense given the environment—even if the results are exactly what you don’t want.
Dynamics problems often show up as process issues, but they’re rarely solved by process alone. They usually trace back to the signals leaders send through their behavior: what gets rewarded, what gets second-guessed, and what happens when things go wrong. That’s why dynamics issues can feel harder than structural ones. Fixing them doesn’t require a re-org or a new doc; it requires leaders to be consistent about how decisions are made, how disagreement is handled, and when they intervene. It requires a hard look in the mirror at how your behavior or the behavior of those above you is causing people to respond.
The good news is that when those signals change, behavior changes quickly. Teams adapt fast to new rules, especially when they’re enforced through action, not words. That’s the leverage at the dynamics level: change the rules of interaction, and people will respond.
Interpersonal: don’t assume interpersonal conflict, but don’t ignore it either
When something feels off on a team, leaders almost always leap to this layer first—“those two people hate each other.” To be fair, a lot of the time that instinct isn’t wrong; it’s just incomplete.
Very often, what looks like interpersonal conflict is actually being caused by something higher up the waterline. Roles aren’t clear, ownership overlaps, or individual or team incentives are not aligned. Two people are stepping on each other’s toes because the structure put them there. In those cases, the conflict isn’t really about the relationship. It’s a structural problem wearing a human face.
But interpersonal dynamics can absolutely destroy teams all on their own. You can have clear goals, clean roles, solid decision-making, etc., and still have two leaders who fundamentally don’t trust or like each other. And when that’s true, it always shows up in the business eventually, through slowed decisions, hoarded information, and teams quietly picking sides.
Once you’ve ruled out structure and dynamics issues, you move to interpersonal, and this is the moment where management gets more direct. At this level, the fix isn’t redesigning the system but, rather, addressing the relationship itself. That usually means naming the tension explicitly, grounding the conversation in how it’s affecting the work, and being clear about what needs to change for the relationship to function. You can make building a solid relationship with a business partner an expectation of someone’s role—something you judge their performance on, particularly if it’s business-critical.
This is the more familiar work of team leadership and management. Sometimes that work leads to repair. Sometimes it becomes clear that trust won’t be rebuilt in a reasonable time frame, and a change has to be made.
Individual: only make it about the person after the system is sound
If your goals are clear, the role is cleaned up, the dynamics are working well, and someone is still not performing, then you’re likely looking at an actual individual issue. At that point, the work is no longer diagnostic. It’s about making a decision.
Individual issues can be personal. Someone going through a tough time outside of work may not be able to meet the expectations of the role right now. Your job as a manager is to decide whether the person can successfully fulfill the role, given the current circumstances.
Evaluate the person against the role as it exists today. Decide whether the gap is coachable in the time frame the business can afford. If it is, invest and be explicit about what needs to change. If it’s not, change the role or make a clean exit. What doesn’t work is lingering in ambiguity.
That’s the leverage at the individual level: once the system is sound, clarity and decisiveness are kinder than dragging things out.
Start at the top. Always. If your team isn’t working well, here’s what the Waterline Model tells you to do: ...
Unsubscribe https://substack.com/redirect/2/eyJlIjoiaHR0cHM6Ly93d3cubGVubnlzbmV3c2xldHRlci5jb20vYWN0aW9uL2Rpc2FibGVfZW1haWw_dG9rZW49ZXlKMWMyVnlYMmxrSWpvME1qWTFNVFV3TkRBc0luQnZjM1JmYVdRaU9qRTROems0TkRVME9Dd2lhV0YwSWpveE56Y3lOVFEyTXpFMkxDSmxlSEFpT2pFNE1EUXdPREl6TVRZc0ltbHpjeUk2SW5CMVlpMHhNRGcwTlNJc0luTjFZaUk2SW1ScGMyRmliR1ZmWlcxaGFXd2lmUS5JUDJ4TnRJQno2d2lUNEpQQjA3N3R3cHVuOXNxaVA0dXRBUi1pU1BoLWRBIiwicCI6MTg3OTg0NTQ4LCJzIjoxMDg0NSwiZiI6dHJ1ZSwidSI6NDI2NTE1MDQwLCJpYXQiOjE3NzI1NDYzMTYsImV4cCI6MjA4ODEyMjMxNiwiaXNzIjoicHViLTAiLCJzdWIiOiJsaW5rLXJlZGlyZWN0In0.j3OeKXzRgOe3_xGFmxIJTFYjwlbmSEjFeRF3G-_hJ9c?
View Email
How to debug a team that isn’t working: the Waterline Model
lenny@substack.com3/3/2026
SubstackView this post on the web at https://www.lennysnewsletter.com/p/the-design-process-is-dead
Jenny Wen leads design for Claude at Anthropic. Prior to this, she was Director of Design at Figma, where she led the teams behind FigJam and Slides. Before that, she was a designer at Dropbox, Square, and Shopify.
Listen on YouTube [ https://substack.com/redirect/85082694-d70d-407d-a3f7-8237cf900446?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], Spotify [ https://substack.com/redirect/1a0dcdc6-6b8a-4840-a947-3ff277808106?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], and Apple Podcasts [ https://substack.com/redirect/94c279f1-4586-4b9a-a397-478f6368d35c?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
We discuss:
Why the classic discovery → mock → iterate design process is becoming obsolete
What a day in the life of a designer at Anthropic looks like, including her AI tool stack
Whether AI will eventually surpass humans in taste and judgment
Why Jenny left a director role at Figma to return to IC work at Anthropic
The three archetypes Jenny is hiring for now
Why chatbot interfaces may be more durable than most people expect
Brought to you by:
Mercury [ https://substack.com/redirect/64f98514-0a1b-4a4c-b9bf-c48443896b1c?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]—Radically different banking
Orkes [ https://substack.com/redirect/00b01a2f-7924-4143-813a-024982da63a6?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]—The enterprise platform for reliable applications and agentic workflows
Omni [ https://substack.com/redirect/b8521b13-b4c9-46c0-b19d-7dbca938e11a?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]—AI analytics your customers can trust
Where to find Jenny Wen:
• X: https://x.com/jenny_wen [ https://substack.com/redirect/0625beee-fb75-4502-9c80-a712ff14c54e?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• LinkedIn: https://www.linkedin.com/in/jennywen [ https://substack.com/redirect/617b7158-4f6e-4aaa-b0c9-ab1083f88f3a?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Substack: https://jennywen.substack.com [ https://substack.com/redirect/1ecbc95a-c1e4-48ca-87ce-ede17d14e0ec?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Website: https://jennywen.ca [ https://substack.com/redirect/3c002e9b-32c3-448a-9d2c-1128d5fb34d7?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Referenced:
• Figma: https://www.figma.com [ https://substack.com/redirect/ee864145-dcd6-4ebc-8924-630273314685?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Anthropic: https://www.anthropic.com [ https://substack.com/redirect/951c8e0d-0773-402a-8607-98f433db3c81?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• v0: https://v0.app [ https://substack.com/redirect/f34c361d-9dd1-49fd-a4b3-2110467eaa13?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Navigating a Design Career with Jenny Wen | Figma at Waterloo: https://www.youtube.com/watch?v=OHcBPMh2ivk [ https://substack.com/redirect/c32e4e33-f06e-4c8d-a085-7e486f40b967?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Claude Cowork: https://claude.com/product/cowork [ https://substack.com/redirect/6e2b47d2-ae2f-4034-b995-80fdefded5d2?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Use Claude Code in VS Code: https://code.claude.com/docs/en/vs-code [ https://substack.com/redirect/6a05d017-9525-4dd2-bc48-c3d83cf4c03f?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Claude Code in Slack: https://code.claude.com/docs/en/slack [ https://substack.com/redirect/631d566a-f2e9-4e73-92fe-2a7313b33c08?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Lex Fridman’s website: https://lexfridman.com [ https://substack.com/redirect/ec4a7dd6-cea8-4410-8cba-8d204acef87f?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Head of Claude Code: What happens after coding is solved | Boris Cherny: https://www.lennysnewsletter.com/p/head-of-claude-code-what-happens [ https://substack.com/redirect/9231e802-17c4-4a87-ad35-8a6cedb5c960?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• OpenClaw: https://openclaw.ai [ https://substack.com/redirect/cfbaf832-d96d-46a4-8498-ef448416c25f?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• OpenAI’s CPO on how AI changes must-have skills, moats, coding, startup playbooks, more | Kevin Weil (CPO at OpenAI, ex-Instagram, Twitter): https://www.lennysnewsletter.com/p/kevin-weil-open-ai [ https://substack.com/redirect/2258eb80-3af2-467e-b31f-59ac62a73b5c?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Marc Andreessen: The real AI boom hasn’t even started yet: https://www.lennysnewsletter.com/p/marc-andreessen-the-real-ai-boom [ https://substack.com/redirect/404f5dfe-5d36-490e-bd0b-e648ce43ba3d?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Socratica: https://www.socratica.info [ https://substack.com/redirect/b0c89258-4f98-4154-a124-a6b97dacf988?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Anthropic’s CPO on what comes next | Mike Krieger (co-founder of Instagram): https://www.lennysnewsletter.com/p/anthropics-cpo-heres-what-comes-next [ https://substack.com/redirect/847c30b6-308e-4246-b26f-21757b6309f4?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Radical Candor: From theory to practice with author Kim Scott: https://www.lennysnewsletter.com/p/radical-candor-from-theory-to-practice [ https://substack.com/redirect/28098b1c-a09d-4770-b7e8-2c433a4da0a1?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Evan Tana’s ‘legibility matrix’ on X: https://x.com/evantana/status/1927404374252269667 [ https://substack.com/redirect/0b5df61c-960c-4af9-91e8-bba3fe57069f?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• How to spot a top 1% startup early: https://www.lennysnewsletter.com/p/how-to-spot-a-top-1-startup-early [ https://substack.com/redirect/b92b5323-c13f-4d05-9992-e0b0e1538e7b?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Palantir: https://www.palantir.com [ https://substack.com/redirect/066ac88e-059f-4692-bee8-d6535d5c8a72?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Stripe: https://stripe.com [ https://substack.com/redirect/5d3656ce-9be3-43a3-a042-8b1d7175c70c?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Linear: https://linear.app [ https://substack.com/redirect/593493b6-8d7c-460f-8b51-afae6c8b1cfd?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Notion: https://www.notion.com [ https://substack.com/redirect/00dcafb7-ab08-4fb0-9936-3b7e3063c745?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Julie Zhuo’s website: https://www.juliezhuo.com [ https://substack.com/redirect/225d6b46-b697-4b55-800f-d65166c4c277?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Sentimental Value: https://www.imdb.com/title/tt27714581 [ https://substack.com/redirect/24f78068-1530-4f4c-9f5c-aa959db813b3?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• The Pitt on Prime Video: https://www.amazon.com/The-Pitt-Season-1/dp/B0DNRR8QWD [ https://substack.com/redirect/d4e7c462-4714-456b-a46d-3b0048e5ed77?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Noah Wyle: https://en.wikipedia.org/wiki/Noah_Wyle [ https://substack.com/redirect/32e8c7fb-478c-44f6-b9b5-9e3917c12657?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• ER on Prime Video: https://www.amazon.com/gp/video/detail/B0FWZSDYRP [ https://substack.com/redirect/75378cc3-f00e-4463-8da0-6452dabbb025?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Retro: https://retro.app [ https://substack.com/redirect/305bcd59-ed7b-47f3-8a78-26e99d1e7d02?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Granola: https://www.granola.ai [ https://substack.com/redirect/47cea2f7-773b-4cbc-bef3-b8bce5c06d1e?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Recommended books:
• Radical Candor: Be a Kick-Ass Boss Without Losing Your Humanity: https://www.amazon.com/Radical-Candor-Kick-Ass-Without-Humanity/dp/1250103509 [ https://substack.com/redirect/1abdf7b5-9918-4d42-bcef-93b89d655911?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• The Power Broker: Robert Moses and the Fall of New York: https://www.amazon.com/Power-Broker-Robert-Moses-Fall/dp/0394480767 [ https://substack.com/redirect/2ee715bc-c429-457e-ac41-ac2671cb0cf2?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Insomniac City: New York, Oliver Sacks, and Me: https://www.amazon.com/Insomniac-City-New-York-Oliver/dp/162040494X [ https://substack.com/redirect/eea1d9b9-88bb-42ca-bd4b-259cd66f4688?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Production and marketing by https://penname.co/ [ https://substack.com/redirect/b85e9909-ae06-4659-bcf2-358bfc654a63?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com [ mailto:podcast@lennyrachitsky.com ].
Lenny may be an investor in the companies discussed.
My biggest takeaways from this conversation:...
Unsubscribe https://substack.com/redirect/2/eyJlIjoiaHR0cHM6Ly93d3cubGVubnlzbmV3c2xldHRlci5jb20vYWN0aW9uL2Rpc2FibGVfZW1haWw_dG9rZW49ZXlKMWMyVnlYMmxrSWpvME1qWTFNVFV3TkRBc0luQnZjM1JmYVdRaU9qRTRPRGcwTmpNNE5Dd2lhV0YwSWpveE56Y3lNemN5TmprMkxDSmxlSEFpT2pFNE1ETTVNRGcyT1RZc0ltbHpjeUk2SW5CMVlpMHhNRGcwTlNJc0luTjFZaUk2SW1ScGMyRmliR1ZmWlcxaGFXd2lmUS5pVXhvZVIxWU1sNVZEQ1hLV3dvWWpJeE9lVmtocFVBX3Y4Y3JjVU83UG9JIiwicCI6MTg4ODQ2Mzg0LCJzIjoxMDg0NSwiZiI6dHJ1ZSwidSI6NDI2NTE1MDQwLCJpYXQiOjE3NzIzNzI2OTYsImV4cCI6MjA4Nzk0ODY5NiwiaXNzIjoicHViLTAiLCJzdWIiOiJsaW5rLXJlZGlyZWN0In0.H6ydSbqB634PqH5O5AJIhbOVpYrSWr_KToRhx5H4qfs?
View Email
The design process is dead. Here’s what’s replacing it. | Jenny Wen (head of design at Claude)
lenny@substack.com3/1/2026
SubstackView this post on the web at https://www.lennysnewsletter.com/p/ai-is-critical-for-humanitys-survival
Jeetu Patel is the president and chief product officer at Cisco, where he leads a team of 30,000 people and is playing a central role in the massive AI infrastructure buildout happening right now. Previously, he spent five years as CPO at Box and 17 years running his own startup. Recently Jeetu organized an AI summit featuring industry leaders like Jensen Huang, Sam Altman, Marc Andreessen, and Fei-Fei Li.
Listen on YouTube [ https://substack.com/redirect/2411fe0f-9aba-4ef5-a687-0304fe644416?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], Spotify [ https://substack.com/redirect/44e2d840-5464-4010-ab55-86805eaa909e?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], and Apple Podcasts [ https://substack.com/redirect/4b14469d-a3f1-44a2-ab8e-4099041f0dac?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
We discuss:
How Cisco went AI-first across 90,000 employees
His six-part framework for building great companies: timing, market, team, product, brand, distribution
Why he says he couldn’t have done this job without AI
His “right to win” strategic framework
His communication framework for preventing “packet loss” across an organization
Why he flips “praise in public, criticize in private” and does the exact opposite
The important communication lesson his mother taught him
Brought to you by:
Sentry [ https://substack.com/redirect/a2b4bb45-807b-4be1-b01b-e8672f8d4df7?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]—Code breaks, fix it faster
Framer [ https://substack.com/redirect/d5c8a2e5-dad9-4043-9c33-5d449a86fbfb?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]—Build better websites faster
Samsara [ https://substack.com/redirect/d6c1f6af-57f7-48d5-839a-337ee47a1016?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]—Saving lives with AI built for physical operations
Where to find Jeetu Patel:
• X: https://x.com/jpatel41 [ https://substack.com/redirect/f68a114a-5c1e-4561-b0cb-744f0d3d8e1f?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• LinkedIn: https://www.linkedin.com/in/jeetupatel [ https://substack.com/redirect/0ece0254-3014-4fba-84a6-3b195fed93b3?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Website: https://blogs.cisco.com/author/jeetupatel [ https://substack.com/redirect/84a9e253-8725-46aa-b85c-2e5eece03c78?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Referenced:
• Jensen Huang on LinkedIn: https://www.linkedin.com/in/jenhsunhuang [ https://substack.com/redirect/a55369fe-8421-4d15-bf51-aec5cec8dfac?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Sam Altman on X: https://x.com/sama [ https://substack.com/redirect/6d84aa7e-dd69-4bb2-8ccc-a58e823a7ae0?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Marc Andreessen: The real AI boom hasn’t even started yet: https://www.lennysnewsletter.com/p/marc-andreessen-the-real-ai-boom [ https://substack.com/redirect/629951c9-b779-4816-a5e6-8b23151caf31?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Fei-Fei Li on LinkedIn: https://www.linkedin.com/in/fei-fei-li-4541247 [ https://substack.com/redirect/9fccd404-451b-47c9-9cb2-add8229aa39b?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Lip-Bu Tan on LinkedIn: https://www.linkedin.com/in/lip-bu-tan-284a7846 [ https://substack.com/redirect/70e453d6-438c-42f7-acc5-e6127a344462?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Matt Garman on LinkedIn: https://www.linkedin.com/in/mattgarman [ https://substack.com/redirect/35ddde21-7405-4b0b-9ff3-3d9f963abdac?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Anthropic’s CPO on what comes next | Mike Krieger (co-founder of Instagram): https://www.lennysnewsletter.com/p/anthropics-cpo-heres-what-comes-next [ https://substack.com/redirect/4b188b84-c0a6-478c-afd6-0e7f3f018b48?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• OpenAI’s CPO on how AI changes must-have skills, moats, coding, startup playbooks, more | Kevin Weil (CPO at OpenAI, ex-Instagram, Twitter): https://www.lennysnewsletter.com/p/kevin-weil-open-ai [ https://substack.com/redirect/f11da1f0-7c17-4029-bc83-30f40e26aa8d?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Kevin Scott on LinkedIn: https://www.linkedin.com/in/jkevinscott [ https://substack.com/redirect/e25abb42-c188-4c2a-887c-a33bd871a9db?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Cisco: https://www.cisco.com [ https://substack.com/redirect/6498bb43-acb0-42b7-96da-42b22e4bae56?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Elon Musk on X: https://x.com/elonmusk [ https://substack.com/redirect/8e277849-54fd-4e6f-a5bd-9b3d1cbc8e15?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Ray Kurzweil’s website: https://www.thekurzweillibrary.com [ https://substack.com/redirect/cee5da36-c6c7-472c-97c1-48713e94b3a7?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• $46B of hard truths from Ben Horowitz: Why founders fail and why you need to run toward fear (a16z co-founder): https://www.lennysnewsletter.com/p/46b-of-hard-truths-from-ben-horowitz [ https://substack.com/redirect/95671b00-a7ef-4ea1-84f0-33b8e6dbb088?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Aaron Levie on LinkedIn: https://www.linkedin.com/in/boxaaron [ https://substack.com/redirect/f3672434-6071-4883-8abc-2e0316b30339?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Box: https://www.box.com [ https://substack.com/redirect/080a3483-576d-481f-8f83-267a6f46e21b?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Chuck Robbins on LinkedIn: https://www.linkedin.com/in/chuck-robbins [ https://substack.com/redirect/96578313-31d4-4d1e-9356-f628ff81cbe5?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Jeffrey Queisser on LinkedIn: https://www.linkedin.com/in/queisser [ https://substack.com/redirect/08862ef1-e990-4a01-8406-865fd1c785dd?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Rick Devenuti on LinkedIn: https://www.linkedin.com/in/rick-devenuti-ba55432 [ https://substack.com/redirect/e204bf48-37bf-4f0a-bb20-8106b83a04dc?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Jeremy Burton on LinkedIn: https://www.linkedin.com/in/jburton0 [ https://substack.com/redirect/bd2a0178-11ea-4e7d-bd9a-2acb6664d4be?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Wes Bush: https://en.wikipedia.org/wiki/Wesley_G._Bush [ https://substack.com/redirect/efe0f9a0-2a08-4555-8886-86c95584db29?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Michael Capellas on LinkedIn: https://www.linkedin.com/in/michael-capellas-36104887 [ https://substack.com/redirect/5aa23245-2289-4be4-8828-c2fbe66771bf?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling): https://www.lennysnewsletter.com/p/10-contrarian-leadership-truths [ https://substack.com/redirect/d5a06928-1915-4b19-91f7-cf6cd52cae51?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Dunbar’s number: https://en.wikipedia.org/wiki/Dunbar%27s_number [ https://substack.com/redirect/8f112b51-6413-44b8-9200-90f0a234173f?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Pat Gelsinger on LinkedIn: https://www.linkedin.com/in/patgelsinger [ https://substack.com/redirect/8cf94ed1-f5d1-401e-bd61-bdefdcfff5eb?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Bernie Madoff: https://en.wikipedia.org/wiki/Bernie_Madoff [ https://substack.com/redirect/10df128b-dd08-4950-ab69-e55bf768f12a?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Taj Mahal: https://en.wikipedia.org/wiki/Taj_Mahal [ https://substack.com/redirect/ecb14615-771e-4fd8-8f89-f7e8f21b6acf?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Six Things a Company Needs to Be Successful: https://www.youtube.com/watch?v=XnlTsEsm6qM [ https://substack.com/redirect/7f5e58f1-5522-4592-8e74-5b3801156028?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Mark Lewis on LinkedIn: https://www.linkedin.com/in/mlewis62 [ https://substack.com/redirect/db223c0d-ab10-4583-a753-a619401967c8?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Web3: https://en.wikipedia.org/wiki/Web3 [ https://substack.com/redirect/b03872f7-2d99-470f-a476-3fe6076a44dc?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• F1: The Movie: https://www.imdb.com/title/tt16311594 [ https://substack.com/redirect/caa4e60f-8b61-4330-81cb-b923df2edb1c?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Zak Brown: https://en.wikipedia.org/wiki/Zak_Brown [ https://substack.com/redirect/43599b9c-2077-4c02-861a-f91a40696da4?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• McLaren Racing: https://www.mclaren.com [ https://substack.com/redirect/d3497b5a-6faa-4e20-b623-e1fb036ee72f?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• ChatGPT: https://chatgpt.com [ https://substack.com/redirect/156c6618-42dd-49ec-a7a2-c77e3e854440?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Gemini: https://gemini.google.com [ https://substack.com/redirect/de5409b9-a38f-442a-a418-bd08856f670c?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Grok: https://grok.com [ https://substack.com/redirect/20f0eda6-4292-493a-9753-22a2147832be?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Sizzler: https://sizzler.com [ https://substack.com/redirect/f96f727a-7a16-4ece-9a55-366d1075dfe5?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Recommended books:
• Be Useful: Seven Tools for Life: https://www.amazon.com/Be-Useful-Seven-Tools-Life/dp/0593655958 [ https://substack.com/redirect/de2627e8-4598-4be4-bbbd-b39e43136fa7?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• The Innovator’s Dilemma: The Revolutionary Book That Will Change the Way You Do Business: https://www.amazon.com/Innovators-Dilemma-Revolutionary-Change-Business/dp/0062060244 [ https://substack.com/redirect/b2ef9882-a690-46eb-9129-f0a376fb0e2d?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• The Innovator’s Solution: https://www.amazon.com/Innovators-Solution-n/dp/B001HYXNKW [ https://substack.com/redirect/277cfc13-b8b1-4174-91d2-77adb089f137?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• The Hard Thing About Hard Things: Building a Business when There Are No Easy Answers―Straight Talk on the Challenges of Entrepreneurship: https://www.amazon.com/Hard-Thing-About-Things-Building/dp/0062273205 [ https://substack.com/redirect/1fbc71e0-2d1c-4a38-b8fc-0a73d3417885?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Production and marketing by https://penname.co/ [ https://substack.com/redirect/6100d2b4-6605-4a00-a7cc-6bc3f7ec4f2c?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com [ mailto:podcast@lennyrachitsky.com ].
Lenny may be an investor in the companies discussed.
My biggest takeaways from this conversation:...
Unsubscribe https://substack.com/redirect/2/eyJlIjoiaHR0cHM6Ly93d3cubGVubnlzbmV3c2xldHRlci5jb20vYWN0aW9uL2Rpc2FibGVfZW1haWw_dG9rZW49ZXlKMWMyVnlYMmxrSWpvME1qWTFNVFV3TkRBc0luQnZjM1JmYVdRaU9qRTROelU0TURBd015d2lhV0YwSWpveE56Y3lNVEV6TlRBNExDSmxlSEFpT2pFNE1ETTJORGsxTURnc0ltbHpjeUk2SW5CMVlpMHhNRGcwTlNJc0luTjFZaUk2SW1ScGMyRmliR1ZmWlcxaGFXd2lmUS5SUWRkZUNaNDlLREx2enBTZVNxemt2OWVVcFJqbGdHYWFVQ3ZmSlg3MGpRIiwicCI6MTg3NTgwMDAzLCJzIjoxMDg0NSwiZiI6dHJ1ZSwidSI6NDI2NTE1MDQwLCJpYXQiOjE3NzIxMTM1MDgsImV4cCI6MjA4NzY4OTUwOCwiaXNzIjoicHViLTAiLCJzdWIiOiJsaW5rLXJlZGlyZWN0In0.1I1mw8cWr8eTa9mWMwkIRj2bX4K6K6TMn53O7YIHMUs?
View Email
AI is critical for humanity’s survival: Cisco president on the AI revolution | Jeetu Patel
lenny@substack.com2/26/2026
SubstackView this post on the web at https://www.lennysnewsletter.com/p/how-to-use-ai-in-your-next-job-interview
👋 Hey there, I’m Lenny. Each week, I answer reader questions about building product, driving growth, and accelerating your career. For more: Lenny’s Podcast [ https://substack.com/redirect/25bb55ac-4f3f-48f5-9c99-ae94708b9de8?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] | Lennybot [ https://substack.com/redirect/9bd5823f-d1eb-43ca-944d-52d6649d06c3?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] | How I AI [ https://substack.com/redirect/14c15ecd-5d23-4074-9e56-c64b0d193340?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
P.S. Get a full free year of Lovable, Manus, Replit, Gamma, n8n, Canva, ElevenLabs, Amp, Factory, Devin, Bolt, Wispr Flow, Linear, PostHog, Framer, Railway, Granola, Warp, Perplexity, Magic Patterns, Mobbin, ChatPRD, and Stripe Atlas by becoming an Insider subscriber [ http://Subscribers get a free year of ].
One of the most frequent questions I’ve seen bubbling up in this community is how AI is impacting the interview process, both for interviewees and for hiring managers.
To find out, my Community Research Lead, Noam Segal [ https://substack.com/redirect/53053c99-0db9-42f8-8a10-21eba2152ceb?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], interviewed dozens of current and recent job seekers as well as hiring managers to learn how AI is transforming both sides of the hiring process.
Part 1 of the results from this research (below) focuses on job seekers—and the approach Noam took here is quite extraordinary. When he started analyzing what he’d learned, he realized the findings didn’t condense into tidy advice or tips. The best candidates had built interconnected systems to arm themselves for every step of the interview process. So Noam did something unique with this post: he encoded the results of his research—the successful techniques from over 30 participants—into a Claude Code–based coach you can plug-and-play into your interview process today.
Once you give it a go, if you have any feedback or suggestions to make this even more useful to you, feel free to email Noam at noam@lennyrachitsky.com [ mailto:noam@lennyrachitsky.com ] (or ping him in our community Slack, @Noam Segal).
Let’s get into it.
For more from Noam, find him on LinkedIn [ https://substack.com/redirect/53053c99-0db9-42f8-8a10-21eba2152ceb?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]. You can listen to this post in convenient podcast form: Spotify [ https://substack.com/redirect/1c947877-fb67-4250-85f1-e7107448e409?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] / Apple [ https://substack.com/redirect/bcd70f45-e5d7-464b-bd94-6c4d5dc20f7f?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] / YouTube [ https://substack.com/redirect/349595d7-bc20-4c91-b368-c50e4ba70d6b?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ].
Logan hadn’t interviewed for a new job in eight years. He’d been at one of the hottest companies in San Francisco, been promoted several times, and never felt the need to look elsewhere. When he decided to pursue a senior architect role at Anthropic, he hit a wall experienced engineers know well: interviewing is its own skill. Day-to-day, Logan solved architecture problems with full context and ample time. Interviews required him to grind LeetCode, whiteboard system designs on the spot, and compress years of expertise into rehearsed stories that fit a rubric.
Normally, preparing for senior engineering loops takes months. Logan had two weeks.
But Logan got the job. When I asked what mattered most, he pointed to his AI workflows as the primary reason he pulled it off.
He’s not alone. I interviewed over 30 tech professionals about how they use AI throughout the interview process. What I found went far beyond polishing resumes. People had built entire systems tailor-made for their own situations: ways to get feedback on what they actually said in interviews, methods to predict questions before walking in, workflows to surface stories they didn’t know they had. Each person I spoke with had figured out how to use AI for one or two pieces of the interviewing puzzle.
I started pulling together a research report from these conversations, but I quickly realized that most people on the job market are stressed and anxious enough. The best value I could offer wasn’t a list of tips but, instead, a way to plug-and-play the hard work these participants have already done. So I changed direction and took every interview AI technique that worked for these participants. Then I added a layer of professional coaching techniques and built a Claude Code–based coach that guides you through how to prepare for job interviews and reach your peak performance.
The Interview Coach I’m offering in this post will give you the critical feedback and real-world reps you need to confidently walk into your next interview room—and succeed.
But first, let’s talk about what’s broken about interview prep today, and how AI solves it.
Interviewing before AI
Interview prep hasn’t changed much in the past decade. You rehearse your stories, maybe run through a mock interview with a friend, and walk into the real thing, hoping everything clicks. But afterward, we’re left with nothing more than a vague sense of how it went, guessing at what to fix. Companies don’t tell you why they passed. Your friends and mentors don’t know what your interviewers were looking for. You’re prepping blind, and the post-interview experience is mostly confusing. There’s simply no usable feedback loop in the interview process.
Of the issues that participants raised in my conversations, three stood out (and all stem from a lack of feedback):
The impostor spiral. Lindsey, a senior PM who’d been at the same company for 10 years, sent out applications and heard nothing. “I started having creeping impostor syndrome,” she told me. “Am I actually a good PM? What’s going on?” Without feedback, you can’t tell if it’s your resume, your approach, your skills, or just bad luck.
The blind grind. Charles spent hours tailoring each resume, hoping to highlight the right experiences. Joan researched companies thoroughly but had no way to know if she was focusing on what interviewers actually cared about. Neither had any signal that their effort was pointed in the right direction.
The practice gap. You can’t get better at something you only do once every few years. And the common advice—to interview at companies you don’t care about to get your reps in—is bad for everyone.
How the most successful candidates used AI to close the feedback loop
Participants who landed roles at top companies all closed the feedback loop themselves by building AI tools.
Greg fed his interview transcripts to Claude, trained it on best practices, and got line-by-line feedback on answers he thought went well but didn’t. Ella built a workflow where she’d paste a job description alongside her resume and have ChatGPT surface the exact gaps a hiring manager would flag and then help her close them before the review. Sean stopped guessing which experiences to highlight. He’d simulate the interview beforehand, test which stories landed, and refine them before the real thing.
Some participants’ systems overlapped; some didn’t. All took real work to build. The problem: assembling those puzzle pieces for yourself would take weeks, and turning them into a successful system is a challenge most people can’t or won’t take on.
The tool you’ll find below pulls all that research together into an AI job interview coach that also leverages best-practice coaching techniques—self-reflection before feedback, powerful questions over prescriptions, co-creation over telling.
Until now, this level of coaching was reserved for those of us who could afford $300-an-hour career coaches. But even a great coach has limits: they can’t analyze a full interview transcript in minutes, track your weak spots across every session, or be there at 11 p.m. when you’re anxious about tomorrow. AI has no such limits, and it’s essentially free.
An AI job interview coach:
Is always on. An AI coach is free, instant, and omnipresent, whenever you need it.
Remembers everything. AI tracks your patterns across sessions, from your weak spots to your standout strengths.
Keeps it real. You can feed call transcripts of your interviews and get feedback on what you said, rather than what you think you said.
So let’s get you set up with an AI interview coach and help you land your next role.
The AI Interview Coach: a free tool to put all this into practice
The Interview Coach is a Claude Code project: a set of instruction files that turn Claude into a rigorous interview coach. You run it by opening the project folder, and it takes over from there.
The coach handles everything that the participants I interviewed were doing (and much more):
Scores your interview responses and tells you exactly what to fix, based on what you said, not what you think you said
Runs a quick company research brief (culture, interview style, and whether the role is a fit) before you even have an interview scheduled
Generates company-specific prep with predicted questions, story mapping against your story bank, interview format guidance, and likely concerns about your background
Runs full mock interviews (4-6 questions, no feedback until the end) and targeted drills that push back, interrupt you, and force you to think on your feet
Mines your experience for stories you didn’t know you had
Coaches you on standing out so you don’t sound like every other candidate who prepped with AI
Helps you strengthen weak stories and retire ones that aren’t landing
Debriefs rejections so you learn something from every no
Rewrites your weakest answers at interview-winning quality, side by side with the original, so the improvement is concrete—not just “add more detail”
Tracks your self-assessment accuracy over time—the gap between how you think you did and how you actually did
Coaches post-offer salary negotiation with exact scripts and fallback language
Let’s get it set up (5 minutes)
We’ll use the Claude desktop app to run our AI interviewing coach.
Here’s how to get started:
Install the Claude desktop app [ https://substack.com/redirect/93f978d1-89fd-4fc2-8ed4-fbc2cfb6975d?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ].
Download the project from GitHub [ https://substack.com/redirect/46644374-ee9b-4894-b4ec-d1f5930a8da1?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] (click Code → Download ZIP and unzip, or Git clone if you prefer).
Rename SKILL.md to CLAUDE.md (just right-click → Rename in your file browser).
Open the Claude desktop app. If you’re already using Claude or Claude Cowork on desktop, you’ve probably encountered Claude Code. Select the “Code” tab.
Open the relevant folder.
Type kickoff and your coach will load.
Claude walks you through the rest, one question at a time.
The whole setup takes about five minutes, and Claude writes a coaching_state.md file that tracks everything across sessions: your stories, scores, patterns, and progress.
Need help using the coach? Type help and you’ll get this:
Let’s take it for a spin!
Once you’ve run kickoff, everything else works through simple commands. Here’s how to use the coach for an upcoming interview.
Basic setup
Quick Prep vs. Full System: Decide if you want to quickly use it for an upcoming interview or want to spend a bit more time setting it up as a comprehensive interview system.
Role selection: Tell it what kind of job you’re looking for.
Feedback directness: Tell it how direct you want feedback to be (1-5 scale, default: 5).
Interview timeline: Share where you’re at in the interview process.
Interview history: Share whether you’ve been interviewing already, how many interviews you’ve done, and how they’ve gone.
Biggest concern: Finally, brain dump what’s stressing you out right now.
At this point, you’re done with the configuration, and Claude Code will ask to learn about your candidate context. Specifically:
Once you provide these details, Claude Code will write an update to its memory and share a summary:
Explore a company early
Interested in a company but don’t have an interview yet? Type research [company name]. Claude pulls together a quick brief on the company’s culture, interview reputation, and how your background maps to what they typically look for. It’s a lighter version of prep, useful when you’re still deciding where to apply or when you want a read on fit before investing in full prep.
Prepare for a specific interview
In the same conversation where you ran kickoff (or a new one):
Type: prep [company name]
You’ll be prompted to attach a job description if there is one and be asked some follow-ups.
Claude Code may request additional information from you. Insider intel is always helpful.
Claude generates a one-page prep brief with what this company optimizes for (based on the JD and their values), your unique positioning for this specific role, 7 to 10 predicted questions tagged by competency with story mapping (which of your stories to use for each, and where the gaps are), likely concerns about your background with one-sentence counters, a culture read on what this company rewards in interviews, and questions for you to ask them.
During prep, you can optionally share LinkedIn profile URLs for your interviewers. The coach needs actual LinkedIn URLs; names alone aren’t reliable enough due to false-match risk. You can include the URLs up front or provide them when the coach asks.
For each interviewer, the coach produces an “Interviewer Intelligence” card covering: their functional lens, career path signals, recent public interests, what you have in common, predicted focus areas, rapport hooks, and watch-for signals (likely interviewing style based on seniority and function). Each card includes a confidence rating so you know how much to rely on it.
If you have a story bank, the coach also maps specific stories to each interviewer—which story to deploy for which person and why. This interviewer intel then flows into other commands: mock calibrates its persona to match the interviewer, hype references their likely focus area, thankyou personalizes your notes, and questions tailors rapport-building questions.
Analyze an interview you just had
Record your interviews using a tool like Granola [ https://substack.com/redirect/55c10c3c-5be8-419b-8a29-13f5b4490636?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] (available as part of Lenny’s Product Pass [ https://substack.com/redirect/8ad1646e-0217-4db3-963f-fafcba819be1?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]) or built-in transcription within Zoom or Google Meet. Then:
Paste your transcript into the chat
Type: analyze
Claude starts by asking how you think it went. Which answers felt strong? Which felt off? Then it scores each answer on five dimensions: substance, structure, relevance, credibility, and differentiation, on a 1-5 scale.
After scoring, it triages: identifies your primary bottleneck, diagnoses the root cause (narrative hoarding? conflict avoidance? status anxiety?), and branches the coaching accordingly. You get a delta sheet with what’s working, what to fix, and which stories to sharpen or retire. If you want, it’ll also give you a side-by-side rewrite of your weakest answer, bringing it up to a quality rating of 4-5.
Then it asks which growth area feels most within your control to change by the next interview. You pick what to work on. This builds the kind of self-awareness that actually shows up in the room.
Over time, it tracks the gap between your self-ratings and the coach’s scores. If you consistently rate your structure higher than it actually is, the coach names that pattern. This calibration—knowing where your blind spots are—is often more valuable than any individual score.
Go deeper: Build a system that compounds
The commands above handle one interview at a time. The commands below, which also come with the coach, build a system across your entire job search.
Build your story bank. Type stories. Claude uses reflective prompts to surface career stories you might overlook. Questions like “When were you at your best at work? What made it different?” and “What’s a decision you’d make differently with hindsight?” It indexes each story by skill, impact, and strength. Most people discover they have more usable material than they thought. Once you have at least 8 stories, you can run a rapid-retrieval drill: Claude throws 10 interview questions at you in rapid succession, and you have 10 seconds per question to name the right story and deliver your opening line. A well-organized story bank is useless if you can’t access it under pressure.
Practice under pressure. Type practice. Choose from eight drill types in progression order: constraint drills at 30 seconds, 60 seconds, 90 seconds, and 3 minutes (practice ladder), handle skepticism and “so what?” pressure (practice pushback), redirect when a question doesn’t match your prep (practice pivot), handle “I don’t have an example for that” moments (practice gap), face role-specific specialist scrutiny (practice role), manage multiple interviewer personas (practice panel), high-pressure simulation (practice stress), or rapid-fire story matching under time pressure (practice retrieval). Drills are gated: you advance when you hit scoring thresholds, not just when you feel ready. After each round, Claude asks what you’d rate yourself before sharing your scores—strengths first, then gaps, then one specific change for the next round.
Run mock interviews. Type mock behavioral Stripe (or whatever format and company you’re prepping for). Unlike drills, which build individual skills, mocks simulate a complete 4- to 6-question interview. Claude delivers questions one at a time with no feedback between them. At least one question targets a known gap in your story bank.
Afterward, you get holistic arc feedback: how your energy shifted across questions, whether you reused stories, how you adapted to interviewer cues, and where you were strongest and weakest across the full session. Individual drills build skills. Mocks test the whole package.
Please note that this is the most limited feature of the coach. Interview processes differ across companies, and interviews are changing. There’s no way to support all interview types. Therefore, the coach elicits as much information as possible from you and tries to be helpful, with clear caveats.
If you’re in product, I highly recommend reading Ben Erez’s product sense [ https://substack.com/redirect/fdf5f60b-da18-4fc7-9040-652bbbd8bbfe?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] and analytical thinking [ https://substack.com/redirect/6356d056-ddaf-4b57-a8e6-87b55df3b8c5?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] articles, or check out his PM interview copilot [ https://substack.com/redirect/9c2aad7d-053b-4acf-8195-9e74b2c768ec?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ].
Stand out. Type stories. Beyond building your story bank, Claude coaches you on differentiation so you don’t sound like every other candidate who prepped with AI. It extracts “earned secrets” from your experience (insights you can only claim because you lived them), sharpens your point of view, and helps you retire stories that aren’t landing.
Anticipate concerns. Type concerns. Claude asks what concerns you expect the interviewer to have, validates the ones you got right, and surfaces the ones you missed—each with counter-evidence and the best story from your story bank to deploy.
Prepare questions to ask. Type questions. Claude generates 5 tailored, non-generic questions—each with why it’s strong, who to ask it to, what the interviewer might ask back, and a prepared response for the reversal.
Track your progress. Type progress. Claude asks what patterns you’re noticing before showing you the data: which competencies are improving, where you’re stagnant, and what to drill next. It closes by asking what you’ve learned about yourself as a communicator, because that self-knowledge is what transfers to the interview room.
Before you walk in. Type hype. Claude generates a 60-second hype “reel” (your biggest wins and strongest metrics, formatted to read aloud), a 3x3 sheet (3 likely concerns with counters, plus 3 questions to ask), a 10-minute physical and mental warmup routine, and mid-interview recovery scripts for when you bomb an answer or get a question you have no story for.
Send a strong follow-up. Type thankyou after an interview. Give it context on what you discussed, and it drafts a thank-you note that reinforces your strongest moments from the conversation.
Negotiate your offer. Type negotiate after you get an offer. Share the details, your ideal outcome, and your walk-away point. Claude helps you interpret the market data you bring (from sources like Levels.fyi and Glassdoor), identifies the most negotiable components, and gives you exact scripts—not just strategy, but the specific words to say, including fallback language for when they push back.
After a rejection. Type debrief. Tell Claude what happened, and it runs a structured debrief to extract what you can learn and carry forward, including what proof points to reinforce and what questions to ask the recruiter.
Done with your job search? Type reflect. Whether you accepted an offer or decided to stay put, Claude runs a retrospective on your full journey: what improved, what patterns persisted, what you learned about yourself as a communicator, and what to carry into your next role when the time comes.
One more thing: Make the coach yours...
Unsubscribe https://substack.com/redirect/2/eyJlIjoiaHR0cHM6Ly93d3cubGVubnlzbmV3c2xldHRlci5jb20vYWN0aW9uL2Rpc2FibGVfZW1haWw_dG9rZW49ZXlKMWMyVnlYMmxrSWpvME1qWTFNVFV3TkRBc0luQnZjM1JmYVdRaU9qRTRPRGMwTXpRek5Td2lhV0YwSWpveE56Y3hPVFF4TkRZMUxDSmxlSEFpT2pFNE1ETTBOemMwTmpVc0ltbHpjeUk2SW5CMVlpMHhNRGcwTlNJc0luTjFZaUk2SW1ScGMyRmliR1ZmWlcxaGFXd2lmUS5pUV9oRlBxUEhBcXhQc0NQRjBOY3pKMVVFYlowSVd5UnRGY0FKdlhkN0lnIiwicCI6MTg4NzQzNDM1LCJzIjoxMDg0NSwiZiI6dHJ1ZSwidSI6NDI2NTE1MDQwLCJpYXQiOjE3NzE5NDE0NjUsImV4cCI6MjA4NzUxNzQ2NSwiaXNzIjoicHViLTAiLCJzdWIiOiJsaW5rLXJlZGlyZWN0In0.ZbGZRs1bsjr7sCHhLqq5Yga0ozA1epHV58WgmiH87FI?
View Email
How to use AI for your next job interview
lenny@substack.com2/24/2026
SubstackView this post on the web at https://www.lennysnewsletter.com/p/head-of-claude-code-what-happens
Boris Cherny is the creator and head of Claude Code at Anthropic. What began as a simple terminal-based prototype just a year ago has transformed the role of software engineering and is increasingly transforming all professional work.
Listen on YouTube [ https://substack.com/redirect/ba3213d5-483a-4171-8e08-ca408a360990?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], Spotify [ https://substack.com/redirect/dbafb93e-535a-4a2a-b781-453a31f5ab46?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], and Apple Podcasts [ https://substack.com/redirect/5659f640-633b-43ae-a78a-aa4db95f69a4?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
We discuss:
How Claude Code grew from a quick hack to 4% of public GitHub commits, with daily active users doubling last month
The counterintuitive product principles that drove Claude Code’s success
Why Boris believes coding is “solved”
The latent demand that shaped Claude Code and Cowork
Practical tips for getting the most out of Claude Code and Cowork
How underfunding teams and giving them unlimited tokens leads to better AI products
Why Boris briefly left Anthropic for Cursor, then returned after just two weeks
Three principles Boris shares with every new team member
Brought to you by:
DX [ https://substack.com/redirect/4df0118b-40e9-4d71-af9e-19cc7f94944c?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]—The developer intelligence platform designed by leading researchers
Sentry [ https://substack.com/redirect/e0284ca3-c44a-48a7-9fcb-dad4ef9eb0f7?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]—Code breaks, fix it faster
Metaview [ https://substack.com/redirect/da16313d-b9b9-4137-abc5-4b79c33f18cd?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]—The AI platform for recruiting
Where to find Boris Cherny:
• X: https://x.com/bcherny [ https://substack.com/redirect/056812ab-119f-468d-ade0-95d6d4266760?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• LinkedIn: https://www.linkedin.com/in/bcherny [ https://substack.com/redirect/56c9accb-a0ae-4da8-bffa-86f072722243?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Website: https://borischerny.com [ https://substack.com/redirect/c0bdd370-9568-499c-a5f4-8b3ed3cd9233?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Referenced:
• Cursor: https://cursor.com [ https://substack.com/redirect/257bf426-f0ad-48f8-a06e-b70c2f40d7fb?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• The rise of Cursor: The $300M ARR AI tool that engineers can’t stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell [ https://substack.com/redirect/47c93f0c-2f47-498d-afa9-edcb37956cb1?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Anthropic: https://www.anthropic.com [ https://substack.com/redirect/9535a26d-fc3d-477c-8364-9fa5285ddf6d?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Anthropic’s CPO on what comes next | Mike Krieger (co-founder of Instagram): https://www.lennysnewsletter.com/p/anthropics-cpo-heres-what-comes-next [ https://substack.com/redirect/d8faa16a-1795-43e2-bbc6-53428782ccbe?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Claude Code Is the Inflection Point: https://newsletter.semianalysis.com/p/claude-code-is-the-inflection-point [ https://substack.com/redirect/d932caa2-cabe-4787-b60e-aaf881437f2e?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Spotify says its best developers haven’t written a line of code since December, thanks to AI: https://techcrunch.com/2026/02/12/spotify-says-its-best-developers-havent-written-a-line-of-code-since-december-thanks-to-ai/ [ https://substack.com/redirect/00f82d99-bd34-4bfb-a902-cf0f8f224256?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Anthropic co-founder on quitting OpenAI, AGI predictions, $100M talent wars, 20% unemployment, and the nightmare scenarios keeping him up at night | Ben Mann: https://www.lennysnewsletter.com/p/anthropic-co-founder-benjamin-mann [ https://substack.com/redirect/257ba026-727a-4fb5-9bc8-95a1837a0acc?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Haiku: https://www.anthropic.com/claude/haiku [ https://substack.com/redirect/f611dbc0-563d-4aa3-85a4-d772950892d8?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Sonnet: https://www.anthropic.com/claude/sonnet [ https://substack.com/redirect/fdc9f598-3dc9-498b-8dd7-69b276f52c08?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Opus: https://www.anthropic.com/claude/opus [ https://substack.com/redirect/8bc0ceae-f61e-4cc6-8cd1-04fd31b7ee03?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Jenny Wen on X: https://x.com/jenny_wen [ https://substack.com/redirect/e3164496-5a44-48fc-939d-cfb19298516e?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Johannes Gutenberg: https://en.wikipedia.org/wiki/Johannes_Gutenberg [ https://substack.com/redirect/3b314c1d-60ae-4144-8dd8-2360ece42f08?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Anthropic jobs: https://www.anthropic.com/careers/jobs [ https://substack.com/redirect/ad50e4e8-8003-48a6-b3a7-a843503da38e?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Lenny’s AI poll post on X: https://x.com/lennysan/status/2020266745722991051 [ https://substack.com/redirect/2c3dbda0-fc8d-4bc3-8ce0-64a744e3c839?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Fiona Fung on LinkedIn: https://www.linkedin.com/in/fionafung [ https://substack.com/redirect/8f4dbc18-c4c3-48f0-8f54-c690f18f6054?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Brandon Kurkela on LinkedIn: https://www.linkedin.com/in/bkurkela [ https://substack.com/redirect/0a8c16c1-37ce-4d0a-8605-e51a485f2035?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Cowork: https://www.anthropic.com/webinars/future-of-ai-at-work-introducing-cowork [ https://substack.com/redirect/f8f14e72-a54b-4ac0-9c68-a8e359bf78a6?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Chris Olah on X: https://x.com/ch402 [ https://substack.com/redirect/b94f581a-5cfa-4c03-b93e-0927b8729016?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• The Bitter Lesson: http://www.incompleteideas.net/IncIdeas/BitterLesson.html [ https://substack.com/redirect/ef0195de-8db8-4b3c-a267-abce6ce9b2da?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• 3 Body Problem on Netflix: https://www.netflix.com/title/81024821 [ https://substack.com/redirect/43a36104-0c66-4058-bae7-8bb309e87d7e?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Acquired podcast: https://www.acquired.fm [ https://substack.com/redirect/61442fe5-f6a2-4faa-b5da-a4df7387a62e?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Acquired: The Complete History & Strategy of Nintendo: https://www.acquired.fm/episodes/nintendo [ https://substack.com/redirect/e6fbcdd9-1f64-4b20-bec4-243ceffca28e?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Recommended books:
• Programming TypeScript: Making Your JavaScript Applications Scale: https://www.amazon.com/Programming-TypeScript-Making-JavaScript-Applications/dp/1492037656 [ https://substack.com/redirect/c778fc46-3817-4bcd-beb8-9086b3007455?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Functional Programming in Scala: https://www.amazon.com/Functional-Programming-Second-Michael-Pilquist-ebook/dp/B0C4LX999T [ https://substack.com/redirect/3d4e8efa-f8ba-4896-8d3c-9deeaa32346d?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Accelerando: https://www.amazon.com/Accelerando-Singularity-Charles-Stross/dp/0441014151 [ https://substack.com/redirect/f68f8b29-58e3-42bd-931f-b14253a9a1bf?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Wandering Earth: https://www.amazon.com/Wandering-Earth-Cixin-Liu/dp/1250796849 [ https://substack.com/redirect/fed385cc-4597-4931-ac1f-ac4e17f14f2c?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• The Three-Body Problem: https://www.amazon.com/Three-Body-Problem-Cixin-Liu/dp/0765382032 [ https://substack.com/redirect/1298da35-cab6-4166-8916-24efee1c2f7a?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• A Fire Upon the Deep: https://www.amazon.com/Fire-Upon-Deep-Zones-Thought/dp/0812515285 [ https://substack.com/redirect/80d8f3fa-b36d-48c7-8f49-3f65d8e219b9?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• A Deepness in the Sky: https://www.amazon.com/Deepness-Sky-Zones-Thought/dp/0812536355 [ https://substack.com/redirect/c785e91d-e7ed-4770-99b6-373df9689d79?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Production and marketing by https://penname.co/ [ https://substack.com/redirect/e0efa5b4-ee5a-4928-8af4-72368a8fc9a1?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com [ mailto:podcast@lennyrachitsky.com ].
Lenny may be an investor in the companies discussed.
My biggest takeaways from this conversation:...
Unsubscribe https://substack.com/redirect/2/eyJlIjoiaHR0cHM6Ly93d3cubGVubnlzbmV3c2xldHRlci5jb20vYWN0aW9uL2Rpc2FibGVfZW1haWw_dG9rZW49ZXlKMWMyVnlYMmxrSWpvME1qWTFNVFV3TkRBc0luQnZjM1JmYVdRaU9qRTRPREUwTnpNNU5Dd2lhV0YwSWpveE56Y3hOVEE0TmprNExDSmxlSEFpT2pFNE1ETXdORFEyT1Rnc0ltbHpjeUk2SW5CMVlpMHhNRGcwTlNJc0luTjFZaUk2SW1ScGMyRmliR1ZmWlcxaGFXd2lmUS5QeWlBS3pQM2czNkowcTY1RVdrSndUeVRJNnMyT1p5VWxnWXN1OGQ0NGpVIiwicCI6MTg4MTQ3Mzk0LCJzIjoxMDg0NSwiZiI6dHJ1ZSwidSI6NDI2NTE1MDQwLCJpYXQiOjE3NzE1MDg2OTgsImV4cCI6MjA4NzA4NDY5OCwiaXNzIjoicHViLTAiLCJzdWIiOiJsaW5rLXJlZGlyZWN0In0.Tbgxvksf_VbIv9EzVAlBeO9Xv-Vri0wH7Lu-hThD-rg?
View Email
Head of Claude Code: What happens after coding is solved | Boris Cherny
lenny@substack.com2/19/2026
SubstackView this post on the web at https://www.lennysnewsletter.com/cp/188400587
Unsubscribe https://substack.com/redirect/2/eyJlIjoiaHR0cHM6Ly93d3cubGVubnlzbmV3c2xldHRlci5jb20vYWN0aW9uL2Rpc2FibGVfZW1haWw_dG9rZW49ZXlKMWMyVnlYMmxrSWpvME1qWTFNVFV3TkRBc0luQnZjM1JmYVdRaU9qRTRPRFF3TURVNE55d2lhV0YwSWpveE56Y3hORE0yTURBNUxDSmxlSEFpT2pFNE1ESTVOekl3TURrc0ltbHpjeUk2SW5CMVlpMHhNRGcwTlNJc0luTjFZaUk2SW1ScGMyRmliR1ZmWlcxaGFXd2lmUS5tNFpEM3h4R1lKeXUxdzcxYjEtVmJ4RWhqX0pnT1RJYXVxT0hyVGxBMklvIiwicCI6MTg4NDAwNTg3LCJzIjoxMDg0NSwiZiI6dHJ1ZSwidSI6NDI2NTE1MDQwLCJpYXQiOjE3NzE0MzYwMDksImV4cCI6MjA4NzAxMjAwOSwiaXNzIjoicHViLTAiLCJzdWIiOiJsaW5rLXJlZGlyZWN0In0.nwzf7ZXoEj3fI5gq2W_6CoSBTW6KVRQywJA9n38jLx4?
View Email
The Promotion Mistakes That Derail PM Careers
lenny@substack.com2/18/2026
SubstackView this post on the web at https://www.lennysnewsletter.com/p/how-to-do-ai-analysis-you-can-actually
👋 Hey there, I’m Lenny. Each week, I answer reader questions about building product, driving growth, and accelerating your career. For more: Lenny’s Podcast [ https://substack.com/redirect/7089dd3a-e84c-4d6e-a6a4-66b5a4ccb9d6?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] | Lennybot [ https://substack.com/redirect/28b615a9-fbc8-475e-bfcb-1a02eaee7b6e?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] | How I AI [ https://substack.com/redirect/eb015cdc-2c0f-4e08-b4c1-33e79494bfc1?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] | My favorite AI/PM courses [ https://substack.com/redirect/246e0816-fab6-44f1-b811-cabc189664c9?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], public speaking course [ https://substack.com/redirect/c472ba3e-e441-4086-a58d-98fbc3c182b3?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], and interview prep copilot [ https://substack.com/redirect/dca08c5e-f5f6-403a-961c-a17ba9665319?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
P.S. Get a full free year of Lovable, Manus, Replit, Gamma, n8n, Canva, ElevenLabs, Amp, Factory, Devin, Bolt, Wispr Flow, Linear, PostHog, Framer, Railway, Granola, Warp, Perplexity, Magic Patterns, Mobbin, ChatPRD, and Stripe Atlas by becoming an Insider subscriber [ http://Subscribers get a free year of ].
The problem with AI is that the output always looks confident—even when it’s full of lies: made-up quotes, false insights, and completely wrong conclusions. As today’s guest author, Caitlin Sullivan [ https://substack.com/redirect/f7942eef-1b93-4120-9316-821976e91981?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], puts it, “These mistakes are invisible until a stakeholder asks a question you can’t answer, or a decision falls apart three months later, or you realize the ‘customer evidence’ behind a major investment actually had enormous holes.”
A user-research veteran, Caitlin has been at the bleeding edge of using AI for user research. She’s trained hundreds of product and research professionals at companies big and small on effective AI-powered customer research and advised teams at companies like Canva and YouTube. Below, she shares her four most effective techniques for getting real, trustworthy, and actionable user insights out of ChatGPT, Claude, Gemini, or your LLM of choice. Let’s get into it.
For more from Caitlin, find her on LinkedIn [ https://substack.com/redirect/f7942eef-1b93-4120-9316-821976e91981?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] and in her new course, Claude Code for Customer Insights [ https://substack.com/redirect/d2d738a2-c393-422b-a365-0d745f1e2d35?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ].
P.S. You can listen to this post in convenient podcast form: Spotify [ https://substack.com/redirect/6811dc74-6d8a-49e0-93e5-da34bb40f8d6?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] / Apple [ https://substack.com/redirect/e0b96282-2489-47ea-b6d4-1a27443eda90?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] / YouTube [ https://substack.com/redirect/cdd1ebd6-c38c-45e0-bca9-26019c2789c1?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ].
Everyone’s “analyzing” customer data with AI. But everyone’s also getting answers full of slop: hallucinations, wrong conclusions, and “insights” that just parrot back what you already told it.
Put the same customer conversation transcripts into two models and get a choose-your-own-adventure experience in return. Each model will give you a different narrative, different “evidence,” and wildly different product recommendations, with the same high level of confidence. Below are two real outputs from that experiment. One is misleading. One is trustworthy. Can you tell which is which?
When they’re side by side, you might spot the problems with the one on the left. But that’s not how this works in practice. You get one output, it reads confidently, and you build your next decision on top of it and never see what’s missing. This is exactly why verification matters.
Here’s what separates these answers: the left output cherry-picks three enthusiastic quotes and leaps to a confident recommendation (“Yes, build a screen”), without questioning whether those quotes represent the full dataset. It looks persuasive, but it’s the AI equivalent of confirmation bias.
The right output does something harder. It challenges the surface-level request (“Do not interpret screen feedback as a single, literal feature request”), segments users by actual need, and flags pricing risk with specific participant timestamps you can verify. It’s messier and doesn’t oversimplify things, but it’s real.
The difference between the two examples above comes down to crucial steps in my workflow to address common failure modes of AI analysis. Those steps force LLMs to maintain the customer’s exact words, dig deep beyond superficial patterns, and catch contradictions in customer stories that will skew final recommendations. Without those checks, false but convincing-looking insights go into a deck and influence a million-dollar decision in the wrong direction.
In this post, I’ll show you how to get relevant and verified insights you can trust. You’ll learn about four failure modes that silently break your AI-supported insights:
Invented evidence
False or generic insights
“Signal” that doesn’t guide better decisions
Contradictory insights
I’ll also teach you my prompting techniques to prevent and catch these errors before they lead to the wrong final decisions. These tactics work across Claude, ChatGPT, Gemini, and with interviews, surveys, or any qualitative or mixed data you’re trying to make sense of with the help of AI.
Why AI struggles with customer research data
Before we get into failure modes, you need to understand what’s difficult about this kind of data for AI in the first place. Models fail with interviews and surveys in different ways.
Interviews are unstructured and messy.
A 45-minute research interview is a messy, wandering conversation. A participant may contradict themself. They go on tangents. They say something important at minute 8 and reframe it completely at minute 35.
LLMs handle this by imposing structure and jumping to conclusions a bit too fast. They find clean themes immediately, pull quotes that fit them best, produce tidy summaries, and call it a day.
But real analysis requires sitting with the mess, noticing contradictions, weighing tangents, and catching tone shifts. Without explicit guidance, AI flattens all of that into something that looks like insight but misses what actually matters.
Even when surveys look structured, they’re not.
You’d think a CSV would be easy to parse. Rows and columns—what’s complicated about that? A lot.
A column of 200 responses to “Why did you cancel?” is just as messy as interview data; maybe worse, because you have none of the context. In an interview, you remember that they hesitated, or had just complained about a specific feature. In a survey, you get “It wasn’t for me” and nothing else.
Your CSV may also not be as clean as you think. Different tools export differently. SurveyMonkey might put question text in headers, while Qualtrics exports headers with internal codes. Some exports even include metadata columns—timestamps, internal tags—sitting right next to customer responses, without clear differentiation. If you don’t tell AI which columns contain the customer’s voice and which to ignore, it analyzes everything as signal. I’ve seen AI treat an internal note (“flagged for follow-up”) as something the customer said.
Even “structured” columns hide complexity. A header that says “Q3_churn probability” tells AI nothing about the scale, the question wording, or whether 5/5 is good or bad.
When analyzing interviews, AI models require help with structure, evidence extraction, and contradiction detection. With surveys, they require help with interpretation, column disambiguation, and understanding what sparse responses actually mean.
The four failure modes below hit both data types and anything similar. Fixing these will typically 10x both the reliability and relevance of your AI analysis results.
What each LLM is best used for
Not all LLMs are equal for analysis work. I’ve run the same analysis process across Claude, ChatGPT, and Gemini over 100 times and worked with discovery tool product teams like Maze testing prompts across models to see what delivers.
Here’s what you need to know about each model:
Claude: Best for thorough analysis with depth and nuance. Delivers more quotes and covers more ground with less pushing. The tradeoff: it gives you the whole brain dump, so themes aren’t always “proven”—you get breadth, not just the safe patterns.
Gemini (and NotebookLM): Best for highly evidenced themes and now video analysis. Gives you fewer themes but with stronger grounding. Expect to prompt multiple times to get completeness, and to ask for longer quotes. Unique advantage: it can analyze non-verbal behaviors in video, which the others can’t (yet).
ChatGPT: Best for final framing and stakeholder communication. Most creative of the three—including with “verbatim quotes,” unfortunately. Least reliable for real evidence (combines quotes), but excels at packaging relevant findings for a specific audience.
Let me show you what I mean:
Unless I give these models more instruction, there are meaningful differences in output. There’s theme overlap, but ChatGPT misses the user’s value/price sensitivity reaction, and all three models give different confidence scores and quotes—some verbatim, some summarized.
This becomes obvious when we can see all three side by side, but most teams have one LLM enterprise account and won’t see the shortcomings of the one they use. ChatGPT summarizes and mashes together verbatim quotes, Claude is more conservative with confidence scores, and Gemini often chooses too-short snippets of customer voice.
My recommendation: If you have a choice, use Claude for analysis work. It covers more ground while staying rooted in the actual data. You get depth and breadth without as much pushing. The tradeoff is that it doesn’t filter for you. You’ll often get validated patterns and half-formed hypotheses presented on equal ground, and you’ll need to verify that themes are well-evidenced. But that’s a better starting point than having to prompt three times before being sure your analysis partner hasn’t missed something.
A note on examples: For consistency, the examples throughout this post typically use ChatGPT. It’s still the most widely used model among my client teams and students, and it’s also the most prone to the specific failure modes I’m covering. The fixes work and improve results across all three models.
Four ways AI data analyses lie to you, and how to fix them
After more than 2,000 hours of testing customer discovery workflows with AI, I’ve found that there are four distinct failure modes for AI analysis—and reliable fixes for each one that consistently work across platforms, data types, models, and workflows.
Failure mode #1: Invented evidence
What the problem looks like
Despite massive improvements across most reasoning models, hallucinations are still abundant. When I look over the shoulders of product people running analysis, I see two hallucination types all the time:
Completely fictionalized quotes (still happens among all three major LLMs)
Frankenstein quotes sewn together from multiple sources that somewhat represent what the user was saying . . . but isn’t actually their words (particularly common in ChatGPT)
Both types go unnoticed unless you’re checking every quote manually, but both are often caused by the way you prompt. You can pretty easily and accidentally trigger ChatGPT to combine multiple customer quotes in ways that can harm our understanding of what the customer was saying. When you add phrases like “max. 100 words” or “for each theme, give a punchy and representative quote that captures it (≤12 words),” you’ll almost always get mash-ups. Highlights in the example below are combinations like this, not the customer’s exact real words.
Why this happens
LLMs don’t retrieve quotes like a search engine; they generate text that’s statistically likely given the context. Generation and retrieval are fundamentally different. The model predicts what a quote should look like. If the context is about phone-checking frustration, it generates plausible phone-checking-frustration language. Sometimes that matches the original, sometimes it’s a near-miss, and sometimes it’s fabricated.
“Verbatim” is also an ambiguous word to prompt a model with. Exact characters? Can punctuation differ? What about filler words? Where does the quote start and end? The model fills these gaps with assumptions you never see. Even participant IDs and timestamps can be faked. A citation like “[P03, 14:30]” looks authoritative but means nothing if the quote is invented.
The fix: Quote selection rules + verification
The solution to this problem, no matter your model, data type, or workflow, has two parts. First, define what a valid quote actually looks like—your quote “rules”—which removes the ambiguity that lets AI fill in gaps. And then verify that quotes in the resulting AI analysis actually exist before you allow the model to use them.
1. Define your quote “rules”
Add this to your analysis prompt:
QUOTE SELECTION RULES
Start where the thought begins, and continue until fully expressed
Include reasoning, not just conclusions
Keep hedges and qualifiers — they signal uncertainty
Include emotional language when present
Cite with participant ID and approximate timestamp [P02 ~14:30]
Do not combine statements from different parts of the interview
If a quote would exceed 3 sentences, break it into separate quotes
This removes ambiguity. The model now knows what “verbatim” means to you: where to start, where to stop, what to include, what not to combine.
I always encourage client teams and course participants to think critically about what makes a quote “good” to them. You’ll likely get much better results right away with my prompt snippet (it’s my favorite copy-paste inclusion) but even better results if you add your own definitions.
2. Verify before you use
After your initial analysis, use this verification prompt to have the LLM confirm that these are real quotes:
QUOTE VERIFICATION
For each quote in the analysis above:
Confirm the quote exists verbatim in the source transcript
If the quote is a close paraphrase but not exact, flag it and provide the actual wording
If the quote cannot be located, mark as NOT FOUND
Output format:
Quote: [the quote]
Status: VERIFIED / PARAPHRASE / NOT FOUND
If paraphrase: Actual wording: [what they said]
Location: [Participant ID, timestamp, or line number]
Here’s what happens when you run that:
A majority of the quotes in the previous ChatGPT output were paraphrased, not original verbatim customer statements. This happened with a request for a small set of quotes, so imagine what happens when you’re digging through 20 interviews and getting just as many patterns back.
Without verification, “quotes” like these end up in your deck attributed to a real participant. Sometimes it’s no big deal. Other times, it’s the difference between product language that strongly resonates and messaging that doesn’t convert.
This often takes just an extra five minutes, depending on how much data you’re dealing with. But it catches errors that would otherwise undermine the evidence behind your product decisions.
Failure mode #2: False or generic insights
What the problem looks like
AI finds themes that are too broad and generic to act on, or biased by what you accidentally primed it with. In interviews, you get themes that could describe any product in your category. I hear this constantly from PMs: “The AI analysis just told me what I already know” or “These insights are too generic. I can’t do anything with them.”
They get outputs like:
“Price is a factor in decisions”
“People value reliability”
“Users want more real-time information”
True, probably, but useless for tough decisions—we need to get deeper than that. These themes could come from so many studies out there. Since I’m working with my fake Whoop data here, they could also easily come from any wearables study.
Themes like these don’t tell you whether your users want this new feature you’re exploring enough to justify the investment, or whether adding it would alienate the customers who chose you specifically because you’re different.
Why this happens
AI defaults to finding consensus, because LLMs are pattern-finding machines. They surface the (obvious) patterns that easily rise to the top, finding what multiple participants mentioned, and then they generate a pattern-matched theme.
The truly most important insight might be something only a few people said in this particular batch of interviews but that, if shared by more customers, would be a noteworthy business signal. Or the most important insight might even be the tension between what people say they want and what their behavior suggests.
LLMs also bring priors from training. If the model has seen thousands of churn analyses where price is the #1 theme, it will weight toward price even if your full dataset doesn’t support it.
In surveys, that tendency to superficially pattern-match is even worse. When someone writes “It’s not for me” when cancelling, AI has to guess what that means. Without guidance, it’ll likely lump that response with others into a generic “value perception” theme. But “not worth it” could mean:
Too expensive for what I’d get
Too data-intensive and I’m not a serious enough athlete
I don’t want another device to charge
I need a screen and Whoop doesn’t have one
It’s one response with four completely different implications for your product decision. Multiply that ambiguity across hundreds of survey responses, and your “themes” become meaningless averages that don’t make decisions any easier.
LLMs are trained to find consensus and compress information. Specificity and valuable edge cases get lost. And if your prompt mentions “pricing issues,” watch how many responses suddenly get coded as pricing-related.
In some cases, that can be helpful, because the model makes sure all outputs are relevant to the specific thing you’re working on. But in many cases, it can be biased cherry-picking from the start.
Here’s an example:
These could describe any wearables study. We can’t make a hardware decision from this.
Another example:
I asked ChatGPT to find me theme clusters and counts for the churn survey question “What did you hope to do that Whoop failed to support you with?”
The results below are clusters that don’t help us make this decision either. So 18% of churned respondents need “more actionable guidance,” which sounds like a job-to-be-done. But there are too many possible directions within that cluster for us to make a decision more easily. Should Whoop focus on clearer metrics or workout plans, or both? Plus, most of this has nothing to do with our screen decision.
When we ask AI to cluster survey responses, we need to give it clear direction with context, or we’re leaving room for mediocre decisions and more manual work.
The fix: Context loading that actually guides interpretation
Most people are used to prompt frameworks that have sections like Role, Context, Task, Format, and so on. Context to most of us means including a few lines of background information in the prompt, somewhere near the beginning. When we’re using AI for analysis, that often focuses on the point of this current customer discovery. Think: objectives, hypotheses, and what part of the product we’re working on.
In the past year, I’ve seen more and more people turn the prompt’s “context” section into four paragraphs of anything they could think of about their work, often dictated in a stream of thought while eating lunch.
But neither three lines of objectives nor the whole unstructured backstory is good enough. Effective context loading has at least four components that shape how AI interprets everything that follows:
Project context tells AI the scope and stakes. “Exploring whether to add a screen” is a specific decision with constraints. “Doing customer research” is vague, so AI defaults to generic analysis because you gave it no frame.
Business goal tells AI what you’re trying to achieve. If you need to know whether a feature would attract new users vs. alienate existing ones in order to prioritize building it, say that. AI will weight evidence toward answering your question and addressing your decision, not the decision it assumes you’re making.
Product context gives AI domain knowledge. Without it, AI interprets “I want to see my data” generically. With it, AI understands that statement in the context of a screenless wearable competing against Apple Watch—a completely different interpretation.
Participant overview tells AI who’s speaking. “I need real-time data” from a churned Garmin switcher means something different than the same words from a loyal user who’s never tried a competitor. AI can only weight evidence correctly if it knows who the evidence is coming from.
The good news is that a lot of what I see people add to the context in their prompts is superfluous. You often don’t need as much information as you think, but it needs to be clear, direct, and relevant information, like the four items above.
For interviews, put this context into an analysis prompt (or use as a single prompt):...
Unsubscribe https://substack.com/redirect/2/eyJlIjoiaHR0cHM6Ly93d3cubGVubnlzbmV3c2xldHRlci5jb20vYWN0aW9uL2Rpc2FibGVfZW1haWw_dG9rZW49ZXlKMWMyVnlYMmxrSWpvME1qWTFNVFV3TkRBc0luQnZjM1JmYVdRaU9qRTROemMzT1RRd05Dd2lhV0YwSWpveE56Y3hNek0yTnpjeUxDSmxlSEFpT2pFNE1ESTROekkzTnpJc0ltbHpjeUk2SW5CMVlpMHhNRGcwTlNJc0luTjFZaUk2SW1ScGMyRmliR1ZmWlcxaGFXd2lmUS5kaDIzUDJOdy02d01MdjVhR1Q5cFVvMTAzeHhFS0lfQks4UzJrNzJma1pVIiwicCI6MTg3Nzc5NDA0LCJzIjoxMDg0NSwiZiI6dHJ1ZSwidSI6NDI2NTE1MDQwLCJpYXQiOjE3NzEzMzY3NzIsImV4cCI6MjA4NjkxMjc3MiwiaXNzIjoicHViLTAiLCJzdWIiOiJsaW5rLXJlZGlyZWN0In0.ME3t-2IsyNmr0a3H3c2tc-xbcYKxsKg6xijKHbG_qB8?
View Email
How to do AI analysis you can actually trust
lenny@substack.com2/17/2026
SubstackView this post on the web at https://www.lennysnewsletter.com/p/sequoia-ceo-coach-why-its-never-been
Brian Halligan co-founded HubSpot, ran it as CEO for about 15 years, and now coaches Sequoia’s fastest-growing founders as their in-house CEO coach.
Listen on YouTube [ https://substack.com/redirect/4e646b57-7b3b-48f7-817d-07adc1e7816a?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], Spotify [ https://substack.com/redirect/ee533220-f2fe-425c-936b-2fae3b4aee37?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], and Apple Podcasts [ https://substack.com/redirect/a7d3da87-8841-4474-a714-ad1ed034977c?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
We discuss:
His LOCKS framework for evaluating founders
Why you should build your team like the 2004 Red Sox
Why hiring “spicy” candidates beats consensus picks
Why enterprise sales will be the last white-collar job AI replaces
Some of my favorite “Halliganisms”
Brought to you by:
Sentry [ https://substack.com/redirect/17ff2aec-fc7c-4197-ba94-d8ec8068890d?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]—Code breaks, fix it faster
Datadog [ https://substack.com/redirect/1fbe94ab-da3c-4ee2-95d5-1b2464ff8994?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]—Now home to Eppo, the leading experimentation and feature flagging platform
WorkOS [ https://substack.com/redirect/9788c9a2-75b9-430e-ab45-b6fa5a3ee8b8?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]—Modern identity platform for B2B SaaS, free up to 1 million MAUs
Where to find Brian Halligan
• X: https://x.com/bhalligan [ https://substack.com/redirect/d99c3a6f-121a-4aee-82c9-244a70f6e538?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• LinkedIn: linkedin.com/in/brianhalligan [ https://substack.com/redirect/230e4b86-e7f0-4932-a9a4-0af67602fecd?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Delphi: https://www.delphi.ai/bhalligan [ https://substack.com/redirect/a2a84fb6-4862-40d4-9402-9af016e39165?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Podcast: https://sequoiacap.com/series/long-strange-trip [ https://substack.com/redirect/f1cbea5f-144c-4397-89b3-16a98ca1e41e?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Referenced:
• Dev Ittycheria on LinkedIn: https://www.linkedin.com/in/dittycheria [ https://substack.com/redirect/5879556f-7905-46d3-8753-06f0a3478fd6?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• HubSpot: https://www.hubspot.com [ https://substack.com/redirect/4f89e312-e56d-425b-83f2-a93a6f3988fe?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Parker Conrad on LinkedIn: https://www.linkedin.com/in/parkerconrad [ https://substack.com/redirect/8c51b976-a74a-4fcc-8fe1-9f3d7bd2cca0?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• McKinsey & Company: https://www.mckinsey.com [ https://substack.com/redirect/42326257-b050-4cd8-8e18-b0987dc24fd2?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Brian Chesky’s new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach [ https://substack.com/redirect/a1bffcb7-02ed-4483-9e9e-3da32259c795?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Jensen Huang on LinkedIn: https://www.linkedin.com/in/jenhsunhuang [ https://substack.com/redirect/d2a72524-844f-42c9-b786-d487ab48b980?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Winston Weinberg on LinkedIn: https://www.linkedin.com/in/winston-weinberg [ https://substack.com/redirect/7497e538-6506-4aa3-a269-83862aa9e705?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• James Cadwallader on LinkedIn: https://www.linkedin.com/in/jsca [ https://substack.com/redirect/298b331c-9af9-4bd3-9bb1-d64d20d5ba5d?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Gabriel Stengel on LinkedIn: https://www.linkedin.com/in/gabestengel [ https://substack.com/redirect/98412623-4ac3-4dd5-a413-7b85141ea147?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• He saved OpenAI, invented the “Like” button, and built Google Maps: Bret Taylor on the future of careers, coding, agents, and more: https://www.lennysnewsletter.com/p/he-saved-openai-bret-taylor [ https://substack.com/redirect/251b725e-3476-4e95-93d0-b67eb5b16a9c?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Scaling Entrepreneurial Ventures: https://orbit.mit.edu/classes/scaling-entrepreneurial-ventures-15.392 [ https://substack.com/redirect/00ecd937-931a-4373-b3bb-ddf297f765c5?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• OpenClaw: https://openclaw.ai [ https://substack.com/redirect/cdc53347-1906-48a6-b04e-3fcae3dab8f5?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Ruth Porat on LinkedIn: https://www.linkedin.com/in/ruth-porat [ https://substack.com/redirect/f1d38ac4-3763-4adf-bb85-1b3418ec5213?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Mike Krzyzewski: https://goduke.com/sports/mens-basketball/roster/coaches/mike-krzyzewski/4159 [ https://substack.com/redirect/1e7ddf50-dcab-4dec-94b2-1f0a4f530ee6?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Dalai Lama’s 18 Rules for Living: https://www.prm.nau.edu/prm205/Dalai-Lama-18-rules-for-living.htm [ https://substack.com/redirect/7f03cbef-2a30-42f4-885b-cb0785f7fc61?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Zigging vs. zagging: How HubSpot built a $30B company | Dharmesh Shah (co-founder/CTO): https://www.lennysnewsletter.com/p/lessons-from-30-years-of-building [ https://substack.com/redirect/001e956c-67bc-4a57-bff9-ca8b42ea2f61?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Kareem Amin on LinkedIn: https://www.linkedin.com/in/kareemamin [ https://substack.com/redirect/f31cd68f-6f8a-45a4-955b-17acb034520c?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Glassdoor: https://www.glassdoor.com [ https://substack.com/redirect/0bbd4dd0-800c-4bf3-9e18-492bbbb30a80?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Tobi Lütke’s leadership playbook: Playing infinite games, operating from first principles, and maximizing human potential (founder and CEO of Shopify): https://www.lennysnewsletter.com/p/tobi-lutkes-leadership-playbook [ https://substack.com/redirect/6b3bea70-b0ac-4860-a4c1-0b55bd124554?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Katie Burke on LinkedIn: https://www.linkedin.com/in/katie-burke-965767a [ https://substack.com/redirect/ec60f7af-0132-487f-a201-23a11c494959?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Jerry Garcia: https://en.wikipedia.org/wiki/Jerry_Garcia [ https://substack.com/redirect/8d5de610-43c3-46d0-839c-41ea27734d43?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Bob Weir: https://en.wikipedia.org/wiki/Bob_Weir [ https://substack.com/redirect/b6fba034-d055-46b0-a78b-0ea9bc9f43a7?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Phil Lesh: https://en.wikipedia.org/wiki/Phil_Lesh [ https://substack.com/redirect/3ccd43e7-c14f-43f7-b87c-525de00b420e?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Ron “Pigpen” McKernan: https://en.wikipedia.org/wiki/Ron_%22Pigpen%22_McKernan [ https://substack.com/redirect/5248c93a-0175-4445-8269-cba613e7e36a?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Marc Andreessen: The real AI boom hasn’t even started yet: https://www.lennysnewsletter.com/p/marc-andreessen-the-real-ai-boom [ https://substack.com/redirect/12a63e98-6e21-434e-aada-e978195e88d9?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• The American Revolution: https://www.pbs.org/kenburns/the-american-revolution [ https://substack.com/redirect/3f7e4453-9702-48d9-9394-bcc3072b6007?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Delphi: https://www.delphi.ai [ https://substack.com/redirect/fffcce4b-fe07-450f-afa9-34f596e9b612?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Sonos: https://www.sonos.com [ https://substack.com/redirect/ec12f93f-e002-47c9-a4e6-89ff90446a86?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Yamini Rangan on LinkedIn: https://www.linkedin.com/in/yaminirangan [ https://substack.com/redirect/1eadb88c-54a7-41b0-b3e6-6989c8cfd340?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• The Boston Red Sox: https://www.mlb.com/redsox [ https://substack.com/redirect/82e00064-eb94-4fd5-a41b-50964ae1fd39?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Recommended book:
• Marketing Lessons from the Grateful Dead: What Every Business Can Learn from the Most Iconic Band in History: https://www.amazon.com/Marketing-Lessons-Grateful-Dead-Business/dp/0470900520 [ https://substack.com/redirect/72a90871-0923-470d-8ff5-17e0023839e0?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Production and marketing by https://penname.co/ [ https://substack.com/redirect/a914f498-1aaa-43d7-afca-9574fe345482?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com [ mailto:podcast@lennyrachitsky.com ].
Lenny may be an investor in the companies discussed.
My biggest takeaways from this conversation:...
Unsubscribe https://substack.com/redirect/2/eyJlIjoiaHR0cHM6Ly93d3cubGVubnlzbmV3c2xldHRlci5jb20vYWN0aW9uL2Rpc2FibGVfZW1haWw_dG9rZW49ZXlKMWMyVnlYMmxrSWpvME1qWTFNVFV3TkRBc0luQnZjM1JmYVdRaU9qRTROekUxTkRnek55d2lhV0YwSWpveE56Y3hNVFl6TURVeUxDSmxlSEFpT2pFNE1ESTJPVGt3TlRJc0ltbHpjeUk2SW5CMVlpMHhNRGcwTlNJc0luTjFZaUk2SW1ScGMyRmliR1ZmWlcxaGFXd2lmUS5HbWhzSVdXMDExRDJ2a3VXc3hoTW1JQVg0dEY2cHpma2ttZE1ZQmw1V2RnIiwicCI6MTg3MTU0ODM3LCJzIjoxMDg0NSwiZiI6dHJ1ZSwidSI6NDI2NTE1MDQwLCJpYXQiOjE3NzExNjMwNTIsImV4cCI6MjA4NjczOTA1MiwiaXNzIjoicHViLTAiLCJzdWIiOiJsaW5rLXJlZGlyZWN0In0.9piPtKgIHpsPLgm2zOnhClBBanMNEoDA4xxf_rBUx1Y?
View Email
Sequoia CEO coach: Why it’s never been easier to start a company, and never been harder to scale one | Brian Halli…
lenny@substack.com2/15/2026
SubstackView this post on the web at https://www.lennysnewsletter.com/p/engineers-are-becoming-sorcerers
Sherwin Wu leads engineering for OpenAI’s API platform, where roughly 95% of engineers use Codex, often working with fleets of 10 to 20 parallel AI agents.
Listen on YouTube [ https://substack.com/redirect/a94538b4-3c50-4aa4-822a-0873427d7c0f?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], Spotify [ https://substack.com/redirect/5217d172-34ea-4ffd-aeab-53622f624348?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], and Apple Podcasts [ https://substack.com/redirect/1b914c56-5697-4b3e-85fc-2789d61d73ad?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
We discuss:
What OpenAI did to cut code review times from 10-15 minutes to 2-3 minutes
How AI is changing the role of managers
Why the productivity gap between AI power users and everyone else is widening
Why “models will eat your scaffolding for breakfast”
Why the next 12 to 24 months are a rare window where engineers can leap ahead before the role fully transforms
Brought to you by:
DX [ https://substack.com/redirect/b827ff53-2f95-442c-b802-dc7e40bd36a6?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]—The developer intelligence platform designed by leading researchers
Sentry [ https://substack.com/redirect/da9962af-8919-4a48-a291-fb736d2be551?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]—Code breaks, fix it faster
Datadog [ https://substack.com/redirect/143cc80e-0ce1-464e-b07a-7462c4d90f13?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]—Now home to Eppo, the leading experimentation and feature flagging platform
Where to find Sherwin Wu:
• X: https://x.com/sherwinwu [ https://substack.com/redirect/45cb777d-f37e-4caa-9fcd-1a3a16ba9b55?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• LinkedIn: https://www.linkedin.com/in/sherwinwu1 [ https://substack.com/redirect/042ad552-21b1-400a-a118-3fbe6f2ca604?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Referenced:
• Codex: https://openai.com/codex [ https://substack.com/redirect/9a306176-573e-4b0b-85e8-f0d9f3c6ee16?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• OpenAI’s CPO on how AI changes must-have skills, moats, coding, startup playbooks, more | Kevin Weil (CPO at OpenAI, ex-Instagram, Twitter): https://www.lennysnewsletter.com/p/kevin-weil-open-ai [ https://substack.com/redirect/5bc226ea-d437-4660-a230-30d4e1892d6b?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• OpenClaw: https://openclaw.ai [ https://substack.com/redirect/831f4e00-ceb9-4e86-9410-9f290ec0dae1?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• The creator of Clawd: “I ship code I don’t read”: https://newsletter.pragmaticengineer.com/p/the-creator-of-clawd-i-ship-code [ https://substack.com/redirect/f19d31d3-8cda-49d9-a97c-88bee55e710f?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• The Sorcerer’s Apprentice: https://en.wikipedia.org/wiki/The_Sorcerer%27s_Apprentice_(Dukas) [ https://substack.com/redirect/d2eeb592-0778-48b0-a725-59063664786f?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Quora: https://www.quora.com [ https://substack.com/redirect/8cd51a46-5594-43fb-b4c6-9cade6394946?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Marc Andreessen: The real AI boom hasn’t even started yet: https://www.lennysnewsletter.com/p/marc-andreessen-the-real-ai-boom [ https://substack.com/redirect/13357910-1eff-47a2-bb9f-6eb785f9af82?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Sarah Friar on LinkedIn: https://www.linkedin.com/in/sarah-friar [ https://substack.com/redirect/856b3dd0-eac1-4dcb-be11-68441857a946?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Sam Altman on X: https://x.com/sama [ https://substack.com/redirect/fb7d460f-326b-414e-b1d5-1f37a19c70ff?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Nicolas Bustamante’s “LLMs Eat Scaffolding for Breakfast” post on X: https://x.com/nicbstme/status/2015795605524901957 [ https://substack.com/redirect/496548a7-1695-4218-ad46-1234fd25b778?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• The Bitter Lesson: http://www.incompleteideas.net/IncIdeas/BitterLesson.html [ https://substack.com/redirect/130edebc-a2f9-4701-8e31-2a73d7ccfc27?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Overton window: https://en.wikipedia.org/wiki/Overton_window [ https://substack.com/redirect/fc41b36f-8ada-4832-8018-1a8c20586429?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Developers can now submit apps to ChatGPT: https://openai.com/index/developers-can-now-submit-apps-to-chatgpt [ https://substack.com/redirect/19d75284-cd02-4a87-8995-e3d865b82912?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Responses: https://platform.openai.com/docs/api-reference/responses [ https://substack.com/redirect/bf8d59d8-7583-40f9-b4bb-a62f0f1038da?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Agents SDK: https://platform.openai.com/docs/guides/agents-sdk [ https://substack.com/redirect/3321ad80-0201-4bdf-adc7-063861a725aa?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• AgentKit: https://openai.com/index/introducing-agentkit [ https://substack.com/redirect/c304d437-ccef-4da1-bd86-00581275d31c?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Ubiquiti: https://ui.com [ https://substack.com/redirect/9031efe1-40ca-4c27-9ee5-c700d0f79268?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Jujutsu Kaisen on Crunchyroll: https://www.crunchyroll.com/series/GRDV0019R/jujutsu-kaisen?srsltid=AfmBOoqvfzKQ6SZOgzyJwNQ43eceaJTQA2nUxTQfjA1Ko4OxlpUoBNRB [ https://substack.com/redirect/03239e42-794d-4456-ad77-5ebc198ec85f?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• eero: https://eero.com [ https://substack.com/redirect/ef31f771-9411-43e0-b2af-648c0f2bb925?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Opendoor: https://www.opendoor.com [ https://substack.com/redirect/63bdf887-2845-4e2c-80a4-bca44470a2c9?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Recommended books:
• Structure and Interpretation of Computer Programs: https://www.amazon.com/Structure-Interpretation-Computer-Programs-Engineering/dp/0262510871 [ https://substack.com/redirect/4cf5d929-1b3a-4b4a-a912-2437a8929e00?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• The Mythical Man-Month: Essays on Software Engineering: https://www.amazon.com/Mythical-Man-Month-Software-Engineering-Anniversary/dp/0201835959 [ https://substack.com/redirect/9c7ba59f-077a-4235-9351-0d6637dc0d3e?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• There Is No Antimemetics Division: A Novel: https://www.amazon.com/There-No-Antimemetics-Division-Novel/dp/0593983750 [ https://substack.com/redirect/76936418-4669-42e6-8a8a-707b13a8f834?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Breakneck: China’s Quest to Engineer the Future: https://www.amazon.com/Breakneck-Chinas-Quest-Engineer-Future/dp/1324106034 [ https://substack.com/redirect/b8539340-e4c4-4311-880f-8bb88ae3ed30?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Apple in China: The Capture of the World’s Greatest Company: https://www.amazon.com/Apple-China-Capture-Greatest-Company/dp/1668053373 [ https://substack.com/redirect/e2e4b884-6efc-4c42-a051-3582c2178506?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Production and marketing by https://penname.co/ [ https://substack.com/redirect/72b7920b-5c83-4867-a737-b1adb46ccd04?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com [ mailto:podcast@lennyrachitsky.com ].
Lenny may be an investor in the companies discussed.
My biggest takeaways from this conversation:...
Unsubscribe https://substack.com/redirect/2/eyJlIjoiaHR0cHM6Ly93d3cubGVubnlzbmV3c2xldHRlci5jb20vYWN0aW9uL2Rpc2FibGVfZW1haWw_dG9rZW49ZXlKMWMyVnlYMmxrSWpvME1qWTFNVFV3TkRBc0luQnZjM1JmYVdRaU9qRTROamd4T0RReU9Td2lhV0YwSWpveE56Y3dPVEF6T0RnMExDSmxlSEFpT2pFNE1ESTBNems0T0RRc0ltbHpjeUk2SW5CMVlpMHhNRGcwTlNJc0luTjFZaUk2SW1ScGMyRmliR1ZmWlcxaGFXd2lmUS41akxjeDM4ZXJ4N3V6Z0Q5Tnl0cnNLLXJDR1loMTNGeWdPWTIzWTVTc1NZIiwicCI6MTg2ODE4NDI5LCJzIjoxMDg0NSwiZiI6dHJ1ZSwidSI6NDI2NTE1MDQwLCJpYXQiOjE3NzA5MDM4ODQsImV4cCI6MjA4NjQ3OTg4NCwiaXNzIjoicHViLTAiLCJzdWIiOiJsaW5rLXJlZGlyZWN0In0.8wIOzj6BazNxeJBN4SdPgsGAAAnCiW-MsJwEw_umY3c?
View Email
“Engineers are becoming sorcerers” | The future of software development with OpenAI’s Sherwin Wu
lenny@substack.com2/12/2026
SubstackView this post on the web at https://www.lennysnewsletter.com/p/building-ai-product-sense-part-2
👋 Hey there, I’m Lenny. Each week, I answer reader questions about building product, driving growth, and accelerating your career. For more: Lenny’s Podcast [ https://substack.com/redirect/d8d275fc-825c-4ffb-9636-89b10c89a8b4?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] | How I AI [ https://substack.com/redirect/440f8cbf-57f4-42c2-acf5-bc472b490900?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] | Lennybot [ https://substack.com/redirect/34f4becf-5af7-45f0-9c19-837e086ed277?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] | My favorite AI/PM courses [ https://substack.com/redirect/d2cc119c-54e5-4cf1-abfa-54b55c9ee177?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], public speaking course [ https://substack.com/redirect/419b2217-bbee-42a2-9e56-627d2090936c?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], and interview prep copilot [ https://substack.com/redirect/b1378953-3a3c-4ebe-b829-acd07eee75f4?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ].
P.S. Subscribers get a free year of [ https://substack.com/redirect/5f7a2e52-7c89-4db5-88d3-3767fbf07f1c?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] Lovable, Manus, Replit, Gamma, n8n, Canva, ElevenLabs, Amp, Factory, Devin, Bolt, Wispr Flow, Linear, PostHog, Framer, Railway, Granola, Warp, Perplexity, Magic Patterns, Mobbin, ChatPRD, and Stripe Atlas. Yes, this is for real [ https://substack.com/redirect/2d21a0c4-0d73-4d0c-a5ac-d4e6f6a16497?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ].
In part two of our in-depth series on building AI product sense (don’t miss part one [ https://substack.com/redirect/43d2b332-229f-45c6-86e3-14470646c47e?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]), Dr. Marily Nika [ https://substack.com/redirect/8a7bcd78-1486-49bf-99ce-3dc560ad49fc?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]—a longtime AI PM at Google and Meta, and an OG AI educator—shares a simple weekly ritual that you can implement today that will rapidly build your AI product sense. Let’s get into it.
For more from Marily [ https://substack.com/redirect/8a7bcd78-1486-49bf-99ce-3dc560ad49fc?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], check out her AI Product Management Bootcamp & Certification [ https://substack.com/redirect/d0d4e0f8-4d5e-4e23-8394-6a5da538457c?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] course (which is also available for private corporate sessions) and her recently launched AI Product Sense and AI PM Interview prep [ https://substack.com/redirect/be9cc116-7b32-4410-901b-b892ef558cbe?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] course (both courses are 15% off using these links). You can also watch her free Lightning Lesson [ https://substack.com/redirect/9213c85d-95d0-4fc6-ba9e-241bd66cc0bb?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] on how to excel as a senior IC PM in the AI era, and subscribe to her newsletter [ https://substack.com/redirect/1236d8b9-3790-4784-b3dd-d116e534db14?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ].
P.S. You can listen to this post in convenient podcast form: Spotify [ https://substack.com/redirect/fa98a383-8bb4-498f-ad6f-9c0582e4aa35?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] / Apple [ https://substack.com/redirect/a6019a88-24ac-4647-af63-d2a214c0cfd3?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] / YouTube [ https://substack.com/redirect/c704278d-52b1-4710-a4c2-49084208b153?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ].
Meta recently added a new PM interview, the first major change to its PM loop in over five years. It’s called “Product Sense with AI,” and candidates are asked to work through a product problem with the help of AI, in real time.
In this interview, candidates aren’t judged on clever prompts, model trivia, or even flashy demos. They are evaluated on how they work with uncertainty: how they notice when the model is guessing, ask the right follow-up questions, and make clear product decisions despite imperfect information.
That shift reflects something bigger. AI product sense—understanding what a model can do and where it fails, and working within those constraints to build a product that people love—is becoming the new core skill of product management.
Over the past year, I’ve watched the same pattern repeat across different teams at work and in my trainings: the AI works beautifully in a controlled flow . . . and then it breaks in production because of a handful of predictable failure modes. The uncomfortable truth is that the hardest part of AI product development comes when real users arrive with messy inputs, unclear intent, and zero patience. For example, a customer support agent can feel incredible in a demo and then, after launch, quietly lose user trust by confidently answering ambiguous or underspecified questions (for example, “Is this good?”) instead of stopping to ask for clarification.
Through my work shipping speech and identity features for conversational platforms and personalized experiences (on-device assistants and diverse hardware portfolios) for 10 years, I started using a simple, repeatable workflow to uncover issues that would otherwise show up weeks later, building this AI product sense for myself first, and then with teams and students. It’s not a theory or a framework but, rather, important practice that gives you early feedback on model behavior, failure modes, and tradeoffs—forcing you to see if an AI product can survive contact with reality before your users teach you the hard way. When I run this process, two things happen quickly: I stop being surprised by model behavior, because I’ve already experienced the weird cases myself. And I get clarity on what’s a product problem vs. what’s a model limitation.
In this post, I’ll walk through my three steps for building AI product sense:
1. Map the failure modes (and the intended behavior)
2. Define the minimum viable quality (MVQ)
3. Design guardrails where behavior breaks
Once that AI product sense muscle develops, you should be able to evaluate a product across a few concrete dimensions: how the model behaves under ambiguity, how users experience failures, where trust is earned or lost, and how costs change at scale. It’s about understanding and predicting how the system will respond to different circumstances.
In other words, the work expands from “Is this a good product idea?” to “How will this product behave in the real world?”
Let’s start building AI product sense.
Map the failure modes (and the intended behavior)
Every AI feature has a failure signature: the pattern of breakdowns it reliably falls into when the world gets messy. And the fastest way to build AI product sense is to deliberately push the model into those failure modes before your users ever do.
I run the following rituals once a week, usually Wednesday mornings before my first meeting, on whatever AI workflow I’m currently building. Together, they run under 15 minutes, and are worth every second. The results consistently surface issues for me that would otherwise show up much later in production.
Ritual 1: Ask a model to do something obviously wrong (2 min.)
Goal: Understand the model’s tendency to force structure onto chaos
Take the kind of chaotic, half-formed, emotionally inconsistent data every PM deals with daily—think Slack threads, meeting notes, Jira comments—and ask the model to extract “strategic decisions” from it. That’s because this is where generative models reveal their most dangerous pattern:
When confronted with mess, they confidently invent structure.
Here’s an example messy Slack thread:
Alice: “Stripe failing for EU users again?”
Ben: “no idea, might be webhook?”
Sara: “lol can we not rename the onboarding modal again?”
Kyle: “Still haven’t figured out what to do with dark mode”
Alice: “We need onboarding out by Thursday”
Ben: “Wait, is the banner still broken on mobile???”
Sara: “I can fix the copy later”
I asked the model to extract “strategic product decisions” from this thread, and it confidently hallucinated a roadmap, assigned the wrong owners, and turned offhand comments into commitments. This is the kind of failure signature every AI PM must design around:
It looks authoritative, clean, structured. And it’s completely wrong.
Now that you have the obviously wrong results, you’ll need to generate the “ideal” response and compare the two responses to understand what signals the model needs to behave correctly.
Here’s exactly what to do:
1. Re-run the same Slack thread through the model
Use the same messy context that caused the hallucination.
Example (you paste the Slack thread):
Based on this Slack discussion, draft our Q4 roadmap.
Let’s say the model invents features you never discussed. Great, you’ve found a failure mode.
2. Now tell the model what good looks like and run it again
Add one short line explaining the expected behavior. For example:
Try again, but only include items explicitly mentioned in the thread. If something is missing, say “Not enough information.”
Run that prompt against the exact same Slack thread. A correct, trustworthy behavior would be:
This answer acknowledges the lack of clear decisions, asks clarifying questions, and surfaces useful structure without inventing facts (“key themes”). It avoids assigning owners unless explicitly stated and highlights uncertainties instead of hiding them.
3. Compare the two outputs—and the inputs that led to them—side by side
This contrast of the two outputs above—confident hallucination vs. humble clarity—is what teaches you how the model behaves today, and what you need to design toward. And that contrast is where AI product sense sharpens fastest.
You’re looking for:
What changed?
What guardrail fixed the hallucination?
What does the model need to behave reliably? (Explicit constraints? Better context? Tighter scoping?)
Does the “good” version feel shippable or still brittle?
What would the user experience in each version?
4. Capture the gaps—this becomes a product requirement
When you see a failure mode repeat, it usually points to a specific kind of product gap (and specific kind of fix).
Now you know where the product fails and its intended behavior. Later in this guide, I’ll show concrete examples of what prompt and design guardrails and retrieval look like in practice, and how to decide when to addthem.
Ritual 2: Ask a model to do something ambiguous (3 min.)
Goal: Understand the model’s semantic fragility
Ambiguity is kryptonite for probabilistic systems because if a model doesn’t fully understand the user’s intent, it fills the gaps with its best guess (i.e. hallucinations, bad ideas). That’s when user trust starts to crack. Try, for example, to input a PRD into NotebookLM [ https://substack.com/redirect/d1a9c0ac-87d1-43bf-a9b7-f11ed03c564b?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] and ask it to “Summarize this PRD for the VP of Product.”
How to try this in 2 minutes (NotebookLM):
Open NotebookLM → create a new notebook
Upload a PRD (Google Doc/PDF works well)
Ask: “Summarize this for execs and list the top 5 risks and open questions.”
Does it:
over-summarize?
latch onto one irrelevant detail?
ignore caveats?
assume the wrong audience?
The model’s failures reveal where its semantic fragility is—in what ways the model technically understands your words but completely misses your intent. Other examples could be if you ask for a summary for leaders and it gives you a bullet list of emojis and jokes from the thread. Or you ask for UX problems and it confidently proposes a new pricing model.
What you’re learning here is where the model gets confused, which is exactly where your product should step in and do the work to reduce ambiguity. That could mean asking the user to choose a goal (“Summarize for who?”), giving the model more context, or constraining the action so the model can’t go off-track. You’re not trying to “trick” the model; you’re trying to understand where communication breaks so you can prevent misunderstanding through design.
Ambiguous prompts: what to test, what breaks, what to do
Here are a few ambiguous prompts to try, along with the different interpretations you should explicitly test:
Now you have another batch of design work for the AI product to help guide it toward predictable and trustworthy results.
Ritual 3: Ask a model to do something unexpectedly difficult (3 min.)
Goal: Understand the model’s first point of failure
Pick one task that feels simple to a human PM but stresses a model’s reasoning, context, or judgment.
You’re not trying to exhaustively test the model. You’re trying to see where it breaks first, so you know where the product needs organizing structure. Where it starts to go wrong is exactly where you need to design guardrails, narrow inputs, or split the task into smaller steps.
Note: This isn’t the final solution yet; it’s the intended behavior. In the guardrails section later, I’ll show how to turn this into an explicit rule in the product (prompt + UX + fallback behavior).
Example 1: “Group these 40 bugs into themes and propose a roadmap.”
Example 2: “Summarize this PRD and flag risks for leadership.”
With results from all three rituals, you now have a complete list of product design work that needs to happen to get the results you and users can use and trust.
Over time, this kind of work also starts to surface second-order effects—moments where a small AI feature quietly reshapes workflows, defaults, or expectations. System-level insights come later, once the foundations are solid. The first goal is to understand behavior.
Define a minimum viable quality (MVQ)
Even when you understand a model’s failure modes and have designed around them, it’s nearly impossible to entirely predict how AI features will behave once they hit the real world, but performance almost always drops once they’re out of the controlled development environment. Since you don’t know how it will drop or by how much, one of the best ways to keep the bar high from the start is to define a minimum viable quality (MVQ) and check it against your product throughout development.
A strong MVQ explicitly defines three thresholds:
Acceptable bar: where it’s good enough for real users
Delight bar: where the feature feels magical
Do-not-ship bar: the unacceptable failure rates that will break trust
Also important in MVQ is the product’s cost envelope: the rough range of what this feature will cost to run at scale for your users.
A concrete example of MVQ comes from my firsthand experience. I spent years working in speech recognition and speaker identification, a domain where the gap between lab accuracy and real-world accuracy is painfully visible.
I still remember demos where the model hit over 90% accuracy in controlled tests and then completely fell apart the first time we tried it in a real home. A barking dog, a running dishwasher, someone speaking from across the room, and suddenly the “great” model felt broken. And from the user’s perspective, it was broken.
With speaker identification for AI features coming from smart speakers, the MVQ of the ability to identify who is speaking would look like this:
Acceptable bar
Correctly identifies the speaker x% of the time in typical home conditions
Recovers gracefully when unsure (“I’m not sure who’s speaking—should I use your profile or continue as a guest?”)
Delight bar
You don’t need a perfect percentage to know that you’ve hit the right delight bar, but you look for behavioral signals like:
Users stop repeating themselves or rephrasing commands
“No, I meant . . .” corrections drop sharply
Rule of thumb: If 8 or 9 out of 10 attempts work without a retry in realistic conditions, it feels magical. If 1 in 5 needs a retry, trust erodes fast. MVQ also depends on the phase you’re in. In a closed beta, users often tolerate rough edges because they expect iteration. In a broad launch, the same failure modes feel broken.
For the speech recognition feature, here are some examples for assessing delight:
Background chaos test: Play a video in the background while two people talk over each other and see if the assistant still responds correctly without asking, “Sorry, can you repeat that?”
6 p.m. kitchen test: Dishwasher running, kids talking, dog barking—and the smart speaker still recognizes you and gives a personalized response without a “I couldn’t recognize your voice” interruption.
Mid-command correction test: You say “Set a timer for 10 minutes . . . actually, make it 5,” and it updates correctly instead of sticking to the original instruction.
Do-not-ship bar
Misidentifies the speaker more than y% of the time in critical flows (purchases, messages, personalized actions)
Forces users to repeat themselves multiple times just to be recognized
You may have noticed I didn’t actually assign values to each bar. That’s because the specific thresholds for MVQ (your “acceptable,” “delight,” and “do-not-ship” bars) aren’t fixed. They depend heavily on your strategic context.
Five strategic context factors that raise or lower your MVQ bar
Here are the five factors that most often determine where that bar should be set, and how they change your product decision:
Estimating the cost envelope
One of the most common mistakes new AI PMs make is falling in love with a magical AI demo without checking whether it’s financially viable. That’s why it’s important to estimate the AI product or feature’s cost envelope early.
Cost envelope = the rough range of what this feature will cost to run at scale for your users
You don’t need perfect numbers, but you need a ballpark. Start with:
What’s the model cost per call (roughly)?
How often will users trigger it per day/month?
What’s the worst-case scenario (power users, edge cases)?
Can caching, smaller models, or distillation bring this down?
If usage 10x’s, does the math still work?
Example: AI meeting notes again
Per-call cost: ~$0.02 to process a 30-minute transcript
Average usage: 20 meetings/user/month → ~$0.40/month/user
Heavy users: 100 meetings/month → ~$2.00/month/user
With caching and a smaller model for “low-stakes” meetings, maybe you bring this to ~$0.25–$0.30/month/user on average
Now you can have a real conversation:
A feature that effectively costs $0.30/user/month and drives retention is a no-brainer.
A feature that ends up at $5/user/month with unclear impact is a business problem.
This is a core part of AI product sense: Does what you’re proposing actually make sense for the business?
Design guardrails where behavior breaks
Now that you better understand where a model’s behavior breaks and what you’re looking for to greenlight a launch, it’s time to codify some guardrails and design them into the product. A good guardrail determines what the product should do when the model hits its limits so that users don’t get confused, misled, or lose trust. In practice, guardrails protect users from experiencing a model’s failure modes. At a startup I’ve been collaborating with, we built an AI feature to increase the team’s productivity that summarized long Slack threads into “decisions and action items.” In testing, it worked well—until it started assigning owners for action items when no one had actually agreed to anything yet. Sometimes it even picked the wrong person.
Because my team had developed our AI product sense, we figured out that the fix was a new guardrail in the product, not a different underlying model.
So we added one simple rule to the system prompt (in this case, just a line of additional instruction):
Only assign an owner if someone explicitly volunteers or is directly asked and confirms. Otherwise, surface themes and ask the user what to do next.
That single constraint eliminated the biggest trust issue almost immediately.
What good guardrails look like in practice...
Unsubscribe https://substack.com/redirect/2/eyJlIjoiaHR0cHM6Ly93d3cubGVubnlzbmV3c2xldHRlci5jb20vYWN0aW9uL2Rpc2FibGVfZW1haWw_dG9rZW49ZXlKMWMyVnlYMmxrSWpvME1qWTFNVFV3TkRBc0luQnZjM1JmYVdRaU9qRTROalkyTVRnd055d2lhV0YwSWpveE56Y3dOek0wTnpVd0xDSmxlSEFpT2pFNE1ESXlOekEzTlRBc0ltbHpjeUk2SW5CMVlpMHhNRGcwTlNJc0luTjFZaUk2SW1ScGMyRmliR1ZmWlcxaGFXd2lmUS5OMFdoUXkzd29GbDJVWHJQdFc4anRCN19zVlNLTzV5cGlyVGZsOHFpU3hnIiwicCI6MTg2NjYxODA3LCJzIjoxMDg0NSwiZiI6dHJ1ZSwidSI6NDI2NTE1MDQwLCJpYXQiOjE3NzA3MzQ3NTAsImV4cCI6MjA4NjMxMDc1MCwiaXNzIjoicHViLTAiLCJzdWIiOiJsaW5rLXJlZGlyZWN0In0.B0vFCo4Jsa1CaCH0FAWlHVW73rSy9UvJrM4sX4AO7UU?
View Email
Building AI product sense, part 2
lenny@substack.com2/10/2026
SubstackView this post on the web at https://www.lennysnewsletter.com/p/getting-paid-to-vibe-code
Lazar Jovanovic is a full-time professional vibe coder at Lovable. His job is to build both internal tools and customer-facing products purely using AI, while not having a coding background. In this conversation, he breaks down the tactics, workflows, and framework that let him ship production-quality products using only AI.
Listen on YouTube [ https://substack.com/redirect/4f4b86c6-dfa5-471c-b3ec-307feb5fd949?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], Spotify [ https://substack.com/redirect/a7f79340-262e-4e48-8824-f9bbbfddfd66?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], and Apple Podcasts [ https://substack.com/redirect/042cd195-8b07-438f-80ea-0118c3b06b10?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
We discuss:
Why having no coding background can be an advantage when building with AI
Why most of your time should go to planning and chat mode, not prompting
What to do when you get stuck: his 4x4 debugging workflow
The PRD and Markdown file system that keeps AI agents aligned across complex builds
Why kicking off four or five parallel prototypes is the best way to clarify your thinking
Why design skills and taste are going to be the most important skills in the future
His “genie and three wishes” mental model for making the most of AI’s limitations
How product, engineering, and design roles are converging—and what that means for your career
Brought to you by:
Strella [ https://substack.com/redirect/c42f2f1e-d02e-4257-8a32-5e7d19efb796?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]—The AI-powered customer research platform
Samsara [ https://substack.com/redirect/92e1f1e0-a9dc-4479-8340-4954a163e254?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]—Saving lives with AI built for physical operations
WorkOS [ https://substack.com/redirect/cb0b31cd-1c26-4a2f-b3ef-14db80696a7a?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]—Modern identity platform for B2B SaaS, free up to 1 million MAUs
Where to find Lazar Jovanovic:
• X: https://x.com/lakikentaki [ https://substack.com/redirect/0642a84a-15cb-4033-bd21-01e973db11ad?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• LinkedIn: https://www.linkedin.com/in/lazar-jovanovic [ https://substack.com/redirect/2ef0835f-9062-433b-9f89-c3cbb5b782f1?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• YouTube: https://www.youtube.com/@50in50challenge [ https://substack.com/redirect/5f595e75-1af3-4a5e-8a54-a45db27a63b7?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Starter Story course: https://build.starterstory.com/build/ai-build-accelerator?via=lazar [ https://substack.com/redirect/b2a43bcc-d1c0-4256-b3cf-762143f24907?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] (code LAZAR15 for 15% off)
Referenced:
• The new AI growth playbook for 2026: How Lovable hit $200M ARR in one year | Elena Verna (Head of Growth): https://www.lennysnewsletter.com/p/the-new-ai-growth-playbook-for-2026-elena-verna [ https://substack.com/redirect/bf06afb4-0f91-4f2e-b4a5-b66f685a9ff8?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Elena Verna on how B2B growth is changing, product-led growth, product-led sales, why you should go freemium not trial, what features to make free, and much more: https://www.lennysnewsletter.com/p/elena-verna-on-why-every-company [ https://substack.com/redirect/58fc9dca-247a-4845-a356-d43adf1b18f9?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• The ultimate guide to product-led sales | Elena Verna: https://www.lennysnewsletter.com/p/the-ultimate-guide-to-product-led [ https://substack.com/redirect/f7eefe15-5eb7-4c12-9af5-2e36d599d137?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• 10 growth tactics that never work | Elena Verna (Amplitude, Miro, Dropbox, SurveyMonkey): https://www.lennysnewsletter.com/p/10-growth-tactics-that-never-work-elena-verna [ https://substack.com/redirect/49245459-afdd-4526-b468-1e677bb1f29c?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Lovable: https://lovable.dev [ https://substack.com/redirect/eb0f3484-db5c-429a-9cf2-00895e808b9e?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Lovable + Shopify: https://lovable.dev/shopify [ https://substack.com/redirect/062f44bd-3452-469e-92ed-d478a65b728a?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Everyone’s an engineer now: Inside v0’s mission to create a hundred million builders | Guillermo Rauch (founder and CEO of Vercel, creators of v0 and Next.js): https://www.lennysnewsletter.com/p/everyones-an-engineer-now-guillermo-rauch [ https://substack.com/redirect/9f6c5f08-4595-4d4e-808b-230d70e01520?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Mobbin: https://mobbin.com [ https://substack.com/redirect/736d8e90-4ab3-4650-9659-86136062b3e6?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Dribbble: https://dribbble.com [ https://substack.com/redirect/2899db0c-0bd4-4a78-bd22-04c2101c0e90?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• 21st.dev: https://21st.dev [ https://substack.com/redirect/331750f5-bf34-41f5-a78a-21abef429dc5?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Lovable base prompt generator: https://chatgpt.com/g/g-67e1da2c9c988191b52b61084438e8ee-lovable-base-prompt [ https://substack.com/redirect/946f179b-4bb7-42a9-909b-ed60b3c858ff?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Lovable PRD generator: https://chatgpt.com/g/g-67e1e85fbeac8191a69b95c6d5c42ef6-lovable-prd-generator [ https://substack.com/redirect/42a9113b-a1fe-4287-b4a6-40f59d5c791d?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Felix Haas’s newsletter: https://designplusai.com [ https://substack.com/redirect/2d13a013-ee65-4877-8c6b-73c7722034cd?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Bauhaus: https://en.wikipedia.org/wiki/Bauhaus [ https://substack.com/redirect/791b1294-0405-46d9-b3e8-0f8eacd0c4ff?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Glassmorphism: https://www.figma.com/community/plugin/1197106608665398190/glassmorphism [ https://substack.com/redirect/1c226d89-a56d-4f48-8669-8082aea41cff?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• UI style guide: http://uistyle.lovable.app [ https://substack.com/redirect/0ccb8280-3624-40e8-9ba5-471b4929b9c3?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Cloudflare: https://www.cloudflare.com [ https://substack.com/redirect/c468594f-f0b4-4316-87e7-252f3c3309bf?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Ben Tossell on X: https://x.com/bentossell [ https://substack.com/redirect/df602cac-ce7c-4997-8bf5-26156ef85e25?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• The rise of Cursor: The $300M ARR AI tool that engineers can’t stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell [ https://substack.com/redirect/4dac452e-ccf2-40d4-bccc-3009e65a3edf?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Peter Thiel says AI will be ‘worse’ for math nerds than for writers: https://www.businessinsider.com/peter-thiel-ai-worse-for-math-professionals-than-writers-2024-4 [ https://substack.com/redirect/548a3e71-cbd6-4d8a-9308-a0ab1085e4ae?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Andrej Karpathy on X: https://x.com/karpathy [ https://substack.com/redirect/3e6af63c-7516-4677-b9da-d3044ca00464?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• The 100-person AI lab that became Anthropic and Google’s secret weapon | Edwin Chen (Surge AI): https://www.lennysnewsletter.com/p/surge-ai-edwin-chen [ https://substack.com/redirect/b2cb17a9-ddf7-4ad7-b86d-c023a04c323a?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Why experts writing AI evals is creating the fastest-growing companies in history | Brendan Foody (CEO of Mercor): https://www.lennysnewsletter.com/p/experts-writing-ai-evals-brendan-foody [ https://substack.com/redirect/0c99c1db-e589-4a13-8d31-08ebc051df3f?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Slumdog Millionaire: https://www.imdb.com/title/tt1010048 [ https://substack.com/redirect/24d8189a-61ab-4ce2-8b14-a73b0070886b?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Production and marketing by https://penname.co/ [ https://substack.com/redirect/8a172045-d0a3-4005-94b4-d2b9fd374051?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com [ mailto:podcast@lennyrachitsky.com ].
Lenny may be an investor in the companies discussed.
My biggest takeaways from this conversation:...
Unsubscribe https://substack.com/redirect/2/eyJlIjoiaHR0cHM6Ly93d3cubGVubnlzbmV3c2xldHRlci5jb20vYWN0aW9uL2Rpc2FibGVfZW1haWw_dG9rZW49ZXlKMWMyVnlYMmxrSWpvME1qWTFNVFV3TkRBc0luQnZjM1JmYVdRaU9qRTROamt5T0RjMk5Dd2lhV0YwSWpveE56Y3dOVFU0TWpVMExDSmxlSEFpT2pFNE1ESXdPVFF5TlRRc0ltbHpjeUk2SW5CMVlpMHhNRGcwTlNJc0luTjFZaUk2SW1ScGMyRmliR1ZmWlcxaGFXd2lmUS53cEoyeEd0SUNHdk15VG5EWkhyT3A0MzFmR0RpbDFBRXZFN052SlNvMU5ZIiwicCI6MTg2OTI4NzY0LCJzIjoxMDg0NSwiZiI6dHJ1ZSwidSI6NDI2NTE1MDQwLCJpYXQiOjE3NzA1NTgyNTQsImV4cCI6MjA4NjEzNDI1NCwiaXNzIjoicHViLTAiLCJzdWIiOiJsaW5rLXJlZGlyZWN0In0.pdxVbnZiv5UftyD8SQl8Q71aT1_rMBf8g3TF5xep8-Y?
View Email
Getting paid to vibe code: Inside the new AI-era job | Lazar Jovanovic (Professional Vibe Coder)
lenny@substack.com2/8/2026
SubstackView this post on the web at https://www.lennysnewsletter.com/p/how-to-build-ai-product-sense
👋 Hey there, I’m Lenny. Each week, I answer reader questions about building product, driving growth, and accelerating your career. For more: Lenny’s Podcast [ https://substack.com/redirect/23be5a37-6b3c-477f-8476-75b18f97921a?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] | How I AI [ https://substack.com/redirect/b0b5f205-d32d-4535-b308-dd958beafe3f?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] | Lennybot [ https://substack.com/redirect/f2977f15-d48a-46c0-b4b9-912b4c70ec4c?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] | Lenny’s Reads [ https://substack.com/redirect/55ae9904-fea9-482f-af34-af8fb44c3577?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] | Favorite AI and PM courses [ https://substack.com/redirect/15fa93aa-b341-4c89-af87-7d5dc971a9ef?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] | Favorite public speaking course [ https://substack.com/redirect/860eae63-822a-4570-9d88-dad1e3164c0a?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
P.S. Insider subscribers [ https://substack.com/redirect/48d71e1a-7a2d-4872-8a4e-9f08ab8b098a?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] get a free year of 23 premium products: Lovable, Manus, Replit, Gamma, n8n, Canva, ElevenLabs, Amp, Factory, Devin, Bolt, Wispr Flow, Linear, PostHog, Framer, Railway, Granola, Warp, Perplexity, Magic Patterns, Mobbin, ChatPRD, and Stripe Atlas [ https://substack.com/redirect/5ff2a17d-c2cb-4a38-8dfd-9f6b948e2bcc?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] (terms apply [ https://substack.com/redirect/583fc960-86e6-4116-83c2-36a10e53d988?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]). Subscribe now [ https://substack.com/redirect/ca6753df-08b3-4592-8361-82b1db3ec583?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ].
The post you’re about to read took over 100 hours to create. That’s because it’s not a post. It’s an open-source interactive AI experience that will help you build AI product sense. Tal and Aman ran dozens of usability sessions, wrote evals, optimized each prompt you’ll find below, and even partnered with Cursor to get you free credits (see below!) so that you can try this at home. I’ve never seen anything like what they’ve put together, and I’m excited to bring it to you.
Next week, in part two of this series, you’ll learn how to take this newfound AI intuition and apply it to your own product.
For more from Tal and Aman, check out their in-depth workshop Build AI Product Sense [ https://substack.com/redirect/8f2420bd-93f5-4ac4-b20a-d1456d4944e7?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] (starting next week, get 15% off using this link) and their upcoming free Lightning Lesson How to Know What AI Products to Build [ https://substack.com/redirect/dc1360b2-64d0-4e36-9c4e-4d35bd73fcd3?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], in partnership with my one of my other favorite collaborators, Hilary Gridley [ https://substack.com/redirect/beb00909-5c05-4d91-957d-6e2428d93531?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]. You can also book Tal and Aman for a build sprint with your team [ https://substack.com/redirect/d975878b-b0e8-41b2-9d97-e3709cb1f2e9?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ].
You’re in a product meeting and someone mentions “subagents” or “context engineering” or “agent memory.” You nod along. You know what these terms mean . . . you’re just hoping no one expects you to use them in a sentence.
You’ve watched the video explainers, bookmarked the infographics, vibe coded a few apps, and even shipped an AI feature. So why does it still feel like you’re miles from truly understanding all this stuff?
We (Tal and Aman) have both been there, over and over again while building AI products for tens of thousands of customers. The problem isn’t you. The problem is the “AI hype industrial complex.” Most AI content is designed to induce FOMO, not to teach: “This model is INSANE” posts, demos that hide the messy reality, and diagrams that complicate more than they explain.
We found that the single most transformative habit to internalize important AI concepts was to move away from consumer-grade UIs (ChatGPT, Granola, Lovable) and into more powerful AI coding agents like Cursor and Claude Code. Getting our hands dirty with coding agents has helped us build our “AI product sense”—the ability to correctly anticipate what will be truly impactful for users and also feasible with AI.
AI product sense is encountering support tickets about AI “forgetting” facts and recognizing it as context rot. Or watching a user struggle through a workflow and confidently saying that agent memory solves this—and knowing how to restructure the experience.
We’ve learned more about how AI products actually work in the past three months by using Cursor for daily, non-technical tasks than in three years of using ChatGPT. This is because coding agents transparently show their work. You can read AI’s reasoning, inspect the tool calls, and watch the context window fill up. You hit the same walls as engineers building AI applications, naturally intuit your own solutions, and start anticipating trends and industry announcements.
We now spend our days using Cursor and Claude Code for daily work: strategy, prioritization, decision-making, data analysis, and productivity. They serve as our thinking partner and personal operating system.
In this post, we’ll guide you through using AI coding agents for your non-technical product work:
In steps 1-4 we’ll get set up and familiar with Cursor with a fun Disney-themed exercise
In steps 5-6 we’ll use Cursor to get hands-on with choosing AI models and calling tools
In steps 7-10, we’ll build a lightweight personal OS (i.e. your own AI product you can use daily) and then improve it with RAG, memory, and context engineering
You’ll walk away with the confidence to anticipate the technology instead of chasing it and, as a bonus, a personal AI operating system. Together we’ll build our AI product sense.
Step 1: Download Cursor
Cursor is hands-down the best coding agent to most quickly ramp up your AI product sense.
You’re probably hearing about Claude Code all over, and we love it for delegating long-running independent tasks like vibe coding. Cursor is still our favorite for pairing with AI and being able to directly watch an AI agent at work.
Cursor is a visual, clickable user experience and can be used with a variety of AI model providers, including OpenAI and Anthropic. That means you can very likely use it at work.
Downloading Cursor will take you two minutes. Do it right now!
1. Download and install Cursor [ https://substack.com/redirect/7ec32c64-9455-4cbb-bc38-b85184402efb?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]. For this post, make sure to download and install the desktop app, not the web version of Cursor.
Step 2: Create a new project
Open Cursor, sign up, power through the onboarding flow, and click “Open project.”
If you’ve already used Cursor before, click File > New Window to get to this screen and open a new project.
Click “New Folder”:
Name it “Build AI Product Sense” and click “Create”:
And finally, click “Open” (yes, it’s unusual to click Open on an empty folder, but just do it, it’ll work):
Step 3: Continue this post inside Cursor
Strap in, because you’re going to continue the experience inside Cursor itself, inspired by the children’s science show The Magic School Bus [ https://substack.com/redirect/8f17a914-e46f-4a22-ab4d-4a2d9e724a23?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ].
If you don’t have time to ride the Magic School Bus right now, you can keep reading below. However, to build your AI product sense, we recommend you come back and try continuing this post inside Cursor using the prompt below.
Make sure you’re in “Agent” mode. This allows Cursor to take actions (such as fetching this post from the internet).
In the “model” dropdown, turn off “auto” and select Opus 4.5 🧠:
🎁 Side note: We’re hooking you up with free Cursor credits 🎁
To help you experience the full power of this tutorial, we’re hooking up Lenny’s Newsletter subscribers with $50 in free Cursor credit. This is enough to get you 2.5 months of standard usage. A huge thank-you to Ben Lang [ https://substack.com/redirect/a69067ca-4ac7-46e0-8a04-77233bec1bcb?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] and team Cursor for making this happen. Note: Supplies are limited, so we may run out of free codes. Act fast.
How to grab your free Cursor credits:
1. Visit Cursor.com/dashboard [ https://substack.com/redirect/9b384bdb-2bb0-4529-b97e-958f8579ba61?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] and sign up for an account.
2. Become an annual (or Insider) Lenny’s Newsletter subscriber [ https://substack.com/redirect/5ef50f8f-98a9-4039-87db-de2f095f1538?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ].
3. Claim your free Cursor code [ https://substack.com/redirect/9881cb29-3445-4a27-be69-c178977c6d21?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] (scroll to the bottom to find Cursor), click the button to redeem your code, and you’ll see the screen below:
4. Click “Get Started” to apply the credits to your account. [Credits can be redeemed with both free and paid accounts.]
5. Once you’ve redeemed the credits, you should see this box appear in your Cursor dashboard. [If you don’t see the credits, try to hard-refresh, or log out and log back in. If that doesn’t work, shoot a message to hi@cursor.com [ mailto:hi@cursor.com ] and mention this post.]
6. Finally, you’ll need to upgrade to the Pro (or higher) plan to use the latest AI models, like Opus 4.5. If you’re already on the Pro or higher plan, you’re all set.
Once you see the credits in your Dashboard, go ahead and upgrade. You won’t be charged anything (you have 2.5 months’ worth of credits). The credits will be automatically applied to the next invoice (and can also be applied to “on-demand usage [ https://substack.com/redirect/9e7e74aa-5d69-4c20-9972-8cc519e5b0bd?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]” if you enable it).
It should look like this:
Now, paste the prompt below into the Cursor chat box:
Help me build my AI product sense using this post (that I have not yet read): https://buildaiproductsense.com/magicschoolbus. (Do not open it in a browser — that will be distracting — use cURL or any other tool.)
Start by giving me an overview of why we’re here and where we’re going with this, so I feel super-motivated to stick with it. Then pause and confirm I’m ready to start. Use the pause to learn more about my professional context (less about Cursor or AI) that could inform our journey together.
Next, walk me through each bite-size concept, in order, one step/question at a time, starting with “Step 3.”
You are both a really good 1-1 tutor for hands-on learning AND the Cursor agent. Have me take action so I’m engaged and learning. Ask me one question at a time. Before starting new steps/stages/ideas/concepts, stop and check in with me and encourage me to explain it back to you — and hold me to a high bar — like an effective, empathetic tutor.
It’s important that you cover every single concept contained in this post, in sequential order. Keep me motivated by signposting and giving clarity on how much we’ve done and how much is left. (That said, leave room to follow my curiosity and go off script, as long as overall we are progressing through the post.)
Use the original words of the post when relevant (you have permission to use them as your words in first person, rather than explicitly quoting someone else). Sentence-case your headings (not title case).
Anytime you come across an image inline in the post, read the image (one at a time, just in time, not in advance, storing temporarily if needed). This is important to understand the contents of the post.
We are already talking inside a Cursor chat thread, so let’s use this same thread for as much as we can. Important: You are also the Cursor agent! So when I say a prompt that you suggested, or give a task like “change this file,” act on it yourself (don’t direct me to do it separately or ask if I did it separately). Don’t refer to a separate Cursor agent. It’s YOU.
Remember that Cursor might be configured in a lot of different ways visually and is constantly evolving, so avoid assumptions about where a UI element might be. The file explorer may be on the left or the right.
Anytime you try to use a tool of any kind, it’s going to ask for my approval, and that’s going to feel scary. So I need you to explain why you’re asking and why it’s safe to approve. It might even be a teachable moment — you can tie to the goal of the post (and where we are in the journey) that, well, you’re an agent and this is you in action!
Consistently encourage me to use the voice recording feature (a 🎙️ icon under the chat box) to build the habit of speech-to-text.
And click “submit”:
If you choose to accept this challenge, you’ll consume the rest of this post from inside Cursor. Stay in one chat thread (“agent”) the entire time (no need to open a new thread or agent).
AI will walk you through the rest of this post. Seatbelts, everyone! We’ll see you in Cursor.
Step 3: Cursor may look intimidating, but you’re more familiar with it than you realize
Cursor looks Matrix-style geeky, but it’s just ChatGPT, a text editor, and a file explorer smooshed into one window.
We repeat, Cursor is just three tools you’ve used plenty of times before, combined:
ChatGPT
A text editor
File explorer
One of Tal’s students, a salesperson, said it best: Cursor is “AI that can touch any file on my computer.”
Here’s a quick tour:
1. Agents
Agents are a fancy term for “chats.” This is where you’ll interact with AI.
On the left, you’ll see an empty panel that will contain your agent history. Click “new agent” to start your first chat (“agent” is synonymous with “chat thread”):
You’ll see a familiar chat box. Click on the dropdown in the bottom left corner. You can select between “Ask” mode and “Agent” mode (ignore the other options, like Plan and Debug, for now).
“Ask” mode is using Cursor just like classic ChatGPT: for chatting, and not making any changes. This is great for brainstorming or asking questions, before taking any action. You can immediately start using this instead of standard ChatGPT/Claude.
“Agent” mode is for when we want Cursor to modify files in our project. We’ll use this together in a moment.
2. Editor
We’ll use this panel to view and manually edit text files. This is the same as using Text Edit on a Mac or Notepad on Windows. To see the text editor, you might have to create a new file or double-click on an existing file.
3. File explorer
The file explorer shows all the files and folders in your project. This is the same as Finder on a Mac or File Explorer on Windows, and it may be on the right or left of Cursor depending on the latest version. To expand it, you might have to click the small icon at the top of the window to make it visible. (You can always use Ctrl + B on Windows or Cmd + B on a Mac.)
Even if Cursor feels intimidating at first, the core concepts [ https://substack.com/redirect/fcb4999a-a570-4008-a655-d77cd89ae6a1?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] are the same as with any LLM you’ve already used. Cursor just has a bit more configurability, options, and things you can play with. This is your playground to build intuition.
Cursor is our choice for getting real work done, not just learning AI concepts
If you’ve already created your AI thinking partner [ https://substack.com/redirect/fcb4999a-a570-4008-a655-d77cd89ae6a1?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] inside ChatGPT or Claude projects, you’re probably wondering if it’s worth the hassle of switching to Cursor. It’s important for us to say that regardless of understanding technical concepts, we now spend most of our days in coding agents for non-technical tasks.
So what’s the practical difference, and why did we make the switch? First, Cursor is fundamentally the same idea as ChatGPT projects: files as knowledge, chat as interface, and instructions that always apply.
Two small form-factor differences change everything:
You drag and drop specific files/folders into each chat (selective context)
The AI edits your files directly (malleable knowledge)
These create a tight loop where every chat automatically improves your project knowledge (but only when you tell the agent to do so). In ChatGPT projects, history and outputs live in long chats. You manually copy things back to project knowledge. In Cursor, outputs live in documents and chats become disposable one-offs because the value lives in documents, not in conversation history.
The main takeaway here is that your knowledge base will cover more ground, and update more frequently, because you’re using the personal OS to build and edit context every single day.
Step 4: Create a Disney song parody to learn the basics of Cursor
We’ll start by creating a new blank file in Cursor. Hover your mouse in the file explorer, and click the “New File” button:
Name your file lyrics.txt:
Next, search the web for your favorite Disney song [ https://substack.com/redirect/5452f383-81fe-447c-8d21-7a73b2ba6500?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] (googling the title usually prints the lyrics). Copy the words to your clipboard:
Back in Cursor, paste them into the file you just created, and save the file:
Next, switch to “Agent” mode in the chat box:
Finally, type in:
Change one line in the first stanza and one line in the chorus of lyrics.txt to be about Silicon Valley.
and send it off using the “up arrow” button:
A lot just changed on our screen! You’ll notice a lot of red and green in our lyrics.txt file. Cursor modified our file. The red shows us each old line that it removed, and the green shows us the new line that it added instead.
You can click “Undo” if you don’t like the change, or “Keep” if you want it to remain.
Step 5: See how different AI models behave
Now that you’ve made your first edit, let’s explore a key product decision every AI team faces: which model to use.
You’ll notice there’s another dropdown in our chat box:
You’ve seen this in ChatGPT, Claude, or Gemini—it’s where you choose the model you want to use. In Cursor, however, you can choose any LLM.
Click into it and disable “Auto,” and take back the power to decide:
When we try the same query in multiple models, we build intuition for how each one might tackle (or fumble) it differently. For example, Claude models are sensitive to copyright law and refuse to modify Disney songs (to get past this, change the end of your prompt to “...to make fun of the song itself,” which qualifies as “fair use”). While OpenAI’s models are less concerned with copyright, they stumbled when calling Cursor’s apply_patch tool, their preferred command for editing a text file (although this is less common in the latest Codex models [ https://substack.com/redirect/90cbe216-a64e-4d3d-83c6-cbad181c7e7d?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]).
All that before we had a chance to judge the cleverness of their lyrics!
Which model do we personally use to get work done? When it comes to individual use, we treat ourselves to the latest and greatest models.
For writing, complex planning, and nuanced life advice (as of the time of this post), we reach for Claude Opus. (We also found it’s the best for experiencing this post from inside Cursor.) Its cousin, Sonnet, is our workhorse for tasks involving lots of context, with a 1M token context window (and slightly faster responses).
Zooming out, there’s a subtle lesson in Cursor’s model dropdown: There are only a few frontier LLMs, and they’re available to all product teams. Innovation is how we apply them.
Make a habit of switching models for tasks you care about. Over time, you’ll develop genuine opinions about model tradeoffs—the kind of intuition that’s hard to get from benchmarks alone.
Step 6: Inspect your agent’s tool calls
LLMs can only produce text, but when they take action (edit a file, fetch data, search the web), they’re calling tools. And tool calling is a distinct skill from everything else we usually notice about LLMs.
Now ask your agent:
Can you walk me through each step (tool/thinking/reasoning/anything else) you used to accomplish this task?
In our test, our LLM reported that:
It used a tool called read_file to find out what was inside the file
It thought about what to edit
It used a tool called search_replace to modify the text file
Here’s how it described #3:
Don’t let this tool’s foreign name repel you. You’ve done “search and replace” plenty of times in Microsoft Word or Google Docs. And you’ve definitely “read a file” before.
(By the way, this is another place where models differ in approach! Gemini consistently accomplished this in three tool calls, while Opus used two. Try it out and see for yourself.)
Coding agents do most of their work with a small set of tools for file navigation and text editing. To see the full set, ask it:
List every tool available to you.
Most of these tools have familiar names; you’ve definitely read the contents of a directory and deleted files before. Others, like read_lints and run_terminal_cmd, are more common in software development (although coding agents can employ them for non-technical requests [ https://substack.com/redirect/b2e7af31-7d4f-4313-bd51-0aa33be5658b?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] too).
How does the LLM actually call the tool? An LLM can’t run commands on your computer, so it relies on Cursor to do so. Think of it like hiring a handyman. The LLM describes what it wants done, but it can’t hold the hammer. Cursor is the handyman: it hears the LLM’s request, uses the tool, and brings back the result so it can decide what to do next.
Cursor recognizes when the LLM prints a tool name (such as above), and executes that tool on your computer. After the tool finishes running, Cursor returns the result to the LLM (i.e. a successful result or an error message) so the LLM can decide what to do next. (If you’ve heard the terms “MCP client” or “agent harness,” those both describe Cursor’s role here.)
The way an LLM interacts with tools is eerily similar to how it interacts with humans. If we view “classic ChatGPT” as a DM thread between an LLM and a human, then AI agents are a three-way group chat between an LLM, a human, and tools [ https://substack.com/redirect/73f893e3-7383-4b89-81dc-7049a6630a5f?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ].
Now when someone asks, “Can our agent do X?” you’ll instinctively think, “What tools would it need, and how good is our model at calling them?” This also connects back to model selection: it’s not just “smartest model wins.” Tool calling is its own behavior [ https://substack.com/redirect/3818b118-2d53-47df-a56e-c5685670123a?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], separate from reasoning or writing quality.
Wait, then what’s the “MCP” I keep hearing about?
For most organizations, the most valuable data doesn’t live in local text files but rather in external SaaS services. For an LLM to interact with Linear, Figma, Notion, Snowflake, BigQuery, Amplitude, or Mixpanel, those services need to provide the LLM with custom tools.
Normally, each SaaS company would have to integrate a separate tool for each LLM out there. To avoid this mess, the industry adopted a standard called Model Context Protocol (MCP). That way, each SaaS company now only needs to build one connector that works everywhere.
If that sounds a lot like USB or Bluetooth, that’s the right analogy. To continue the comparison: most agent tools aren’t MCP, just like most electrical wires aren’t shaped like USB plugs. For simplicity, MCP is just another tool the agent can use, with a standardized interface.
Step 7: Put everything into practice by building your personal OS inside Cursor
Now that we understand how agents work generally, let’s create a personalized AI agent for ourselves to see how the components of Cursor come together.
We’re going to build a very lightweight, minimal personal productivity system that organizes our contacts from various parts of our life, like notes, transcripts, and unstructured thoughts, as well as some tasks that we need to get done. (This lets us temporarily ignore discovery, distribution, and pricing. We’ll be free to focus on what’s technically possible.)
By the end of this exercise, you’ll be able to ask Cursor to create tasks from your backlog and get started on those tasks based on the context you provided in the knowledge and goals. In the process, we’ll learn about RAG, memory, and context engineering and build critical parts of product sense.
To get started, you can copy and paste the following prompt into Cursor (make sure you’re on “Agent” mode):...
Unsubscribe https://substack.com/redirect/2/eyJlIjoiaHR0cHM6Ly93d3cubGVubnlzbmV3c2xldHRlci5jb20vYWN0aW9uL2Rpc2FibGVfZW1haWw_dG9rZW49ZXlKMWMyVnlYMmxrSWpvME1qWTFNVFV3TkRBc0luQnZjM1JmYVdRaU9qRTROakl5TmpJMU1pd2lhV0YwSWpveE56Y3dNVEkzTWpFNExDSmxlSEFpT2pFNE1ERTJOak15TVRnc0ltbHpjeUk2SW5CMVlpMHhNRGcwTlNJc0luTjFZaUk2SW1ScGMyRmliR1ZmWlcxaGFXd2lmUS5RdzRObWd2Q0JnVm5ETXdrLXAyWFdtaUlXMnR1RUNaMVJ5amNvR2J0cFJRIiwicCI6MTg2MjI2MjUyLCJzIjoxMDg0NSwiZiI6dHJ1ZSwidSI6NDI2NTE1MDQwLCJpYXQiOjE3NzAxMjcyMTgsImV4cCI6MjA4NTcwMzIxOCwiaXNzIjoicHViLTAiLCJzdWIiOiJsaW5rLXJlZGlyZWN0In0.UDHtDYpDDKJVdB2DX798Ubb46KxoFIcZGz2HPBGD9Zk?
View Email
How to build AI product sense
lenny@substack.com2/3/2026
SubstackView this post on the web at https://www.lennysnewsletter.com/p/dr-becky-on-the-surprising-overlap
Dr. Becky Kennedy is a clinical psychologist, the bestselling author of Good Inside, and the founder of a parenting platform used by millions. Known for her practical, psychology-based approach to parenting, Dr. Becky shares how the same principles that help parents raise resilient children can make you a much more effective leader. In this conversation, she breaks down why all human systems—whether families or companies—operate on the same fundamental principles, and how understanding these dynamics can make you more effective in every relationship.
Listen on YouTube [ https://substack.com/redirect/f1f24fef-c304-434a-abe5-2bc1230cfda9?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], Spotify [ https://substack.com/redirect/80af34c3-9da5-443e-910b-3e7d4dddf622?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], and Apple Podcasts [ https://substack.com/redirect/2c9cbc22-db68-4b79-966d-5b793ac8f36e?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
We discuss:
Why repair—not perfection—defines strong leadership
Why you need to connect before you correct to build cooperation and trust
The “most generous interpretation” framework for handling difficult behaviors
How to correctly set boundaries (vs. making requests)
The power of “I believe you, and I believe in you”
What it looks like to be a “sturdy” leader
Brought to you by:
Merge [ https://substack.com/redirect/43b9581f-e213-43f4-95f2-83582f7eded7?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]—Fast, secure integrations for your products and agents
Metaview [ https://substack.com/redirect/b8211cef-fa7a-4bc9-9283-bf49c7d58040?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]—The AI platform for recruiting
Framer [ https://substack.com/redirect/baae352c-4b9c-4da7-8c24-c878afdd7e82?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]—Builder better websites faster
Where to find Dr. Becky Kennedy:
• X: https://x.com/GoodInside [ https://substack.com/redirect/c1035c52-220c-48c7-a2ff-dbfe13a32382?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• LinkedIn: https://www.linkedin.com/in/drbecky [ https://substack.com/redirect/10d082b2-1a52-442a-857a-3b8b0543f5b0?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Instagram: https://www.instagram.com/drbeckyatgoodinside [ https://substack.com/redirect/f375ecc1-e5ab-471b-b863-9e0e53b81b99?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• TikTok: https://www.tiktok.com/@drbeckyatgoodinside [ https://substack.com/redirect/2f6d8679-f8dc-4a77-8dfe-b80a56bea6df?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Website: https://www.goodinside.com [ https://substack.com/redirect/afb1242e-a1af-4eee-9071-ad8c0cc8fe9c?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Referenced:
• Shreyas Doshi on pre-mortems, the LNO framework, the three levels of product work, why most execution problems are strategy problems, and ROI vs. opportunity cost thinking: https://www.lennysnewsletter.com/p/episode-3-shreyas-doshi [ https://substack.com/redirect/02540f3c-c7d2-4dba-846f-4cf1b512709d?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Radical Candor: From theory to practice with author Kim Scott: https://www.lennysnewsletter.com/p/radical-candor-from-theory-to-practice [ https://substack.com/redirect/e9544db3-7f76-466c-a509-0285c23ba90b?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• From ChatGPT to Instagram to Uber: The quiet architect behind the world’s most popular products | Peter Deng: https://www.lennysnewsletter.com/p/the-quiet-architect-peter-deng [ https://substack.com/redirect/546ff227-a325-42c3-93b3-0995d510f920?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Punch: https://en.wikipedia.org/wiki/Punch_(play) [ https://substack.com/redirect/5aa4333e-522d-42cd-b0cb-b8f13b1dafd8?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Figma: https://www.figma.com [ https://substack.com/redirect/74142254-840d-4142-ab7e-b5a3b10d91ee?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Andrew Hogan on LinkedIn: https://www.linkedin.com/in/ahhogan [ https://substack.com/redirect/27b6b8a2-56a4-4a6d-bfcb-49b7aa8c4ba0?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Replit: https://replit.com [ https://substack.com/redirect/ea86ef0c-6b35-4792-a14b-513be3820809?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Behind the product: Replit | Amjad Masad (co-founder and CEO): https://www.lennysnewsletter.com/p/behind-the-product-replit-amjad-masad [ https://substack.com/redirect/0f2a63d7-5659-49e3-8669-42e74b6c305d?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Lovable: https://lovable.dev [ https://substack.com/redirect/f0001814-452b-490a-8772-0a2e5b623187?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Building Lovable: $10M ARR in 60 days with 15 people | Anton Osika (co-founder and CEO): https://www.lennysnewsletter.com/p/building-lovable-anton-osika [ https://substack.com/redirect/a690760f-3260-4954-a41a-697bcdfdb4e7?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Claude: https://claude.ai [ https://substack.com/redirect/3e082491-2f37-4be6-aa19-09c961509f3e?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• ChatGPT: https://chatgpt.com [ https://substack.com/redirect/d93d4de8-df65-4c85-9323-8d31a65b1281?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Secrets We Keep on Netflix: https://www.netflix.com/title/81697668 [ https://substack.com/redirect/9a981bdd-e0a0-4a14-a200-3ab85f944c9e?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• K Pop Demon Hunters on Netflix: https://www.netflix.com/title/81498621 [ https://substack.com/redirect/53535b8d-b243-4542-8372-a259d7598366?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Liberty puzzles: https://libertypuzzles.com [ https://substack.com/redirect/8c1e5afe-0ad1-4755-b36e-183011eddf7a?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Recommended books:
• Radical Candor: Be a Kick-Ass Boss Without Losing Your Humanity: https://www.amazon.com/Radical-Candor-Revised-Kick-Ass-Humanity/dp/1250235375 [ https://substack.com/redirect/a2980e34-4b7e-47fa-9ffe-e97a9005a832?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Good Inside: A Practical Guide to Resilient Parenting Prioritizing Connection Over Correction: https://www.amazon.com/Good-Inside-Guide-Becoming-Parent/dp/0063159481 [ https://substack.com/redirect/da43f285-d501-4040-a00a-64c0f8595292?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Leave Me Alone!: A Good Inside Story About Deeply Feeling Kids: https://www.amazon.com/Leave-Me-Alone-Inside-Feeling/dp/1250413117 [ https://substack.com/redirect/0e21cfca-0fd3-4388-ad68-d843257a90bc?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• The Power of Moments: Why Certain Experiences Have Extraordinary Impact: https://www.amazon.com/Power-Moments-Certain-Experiences-Extraordinary/dp/1501147765/ [ https://substack.com/redirect/0303e171-ec20-4a9c-b97e-dc9e1fe78c91?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• The Messy Middle: Finding Your Way Through the Hardest and Most Crucial Part of Any Bold Venture: https://www.amazon.com/Messy-Middle-Finding-Through-Hardest/dp/0735218072 [ https://substack.com/redirect/b7c25c3d-e52d-421b-82e2-79d294f0b330?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Creativity, Inc.: Overcoming the Unseen Forces That Stand in the Way of True Inspiration: https://www.amazon.com/Creativity-Inc-Expanded-Overcoming-Inspiration/dp/0593594649 [ https://substack.com/redirect/3595dd6c-e10b-4a75-9724-11b3e6fa7d78?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Production and marketing by https://penname.co/ [ https://substack.com/redirect/bab0fe0e-55d7-4498-b4fa-ed56ecb6fdb5?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com [ mailto:podcast@lennyrachitsky.com ].
Lenny may be an investor in the companies discussed.
My biggest takeaways from this conversation:...
Unsubscribe https://substack.com/redirect/2/eyJlIjoiaHR0cHM6Ly93d3cubGVubnlzbmV3c2xldHRlci5jb20vYWN0aW9uL2Rpc2FibGVfZW1haWw_dG9rZW49ZXlKMWMyVnlYMmxrSWpvME1qWTFNVFV3TkRBc0luQnZjM1JmYVdRaU9qRTRORGN4TkRneU5Dd2lhV0YwSWpveE56WTVPVFV6TlRnd0xDSmxlSEFpT2pFNE1ERTBPRGsxT0RBc0ltbHpjeUk2SW5CMVlpMHhNRGcwTlNJc0luTjFZaUk2SW1ScGMyRmliR1ZmWlcxaGFXd2lmUS5DdVZjSVRMMFQzR011NlVlbFpDbkNqOUtfNHg3SnRVZGZ2VGt4bHloemZzIiwicCI6MTg0NzE0ODI0LCJzIjoxMDg0NSwiZiI6dHJ1ZSwidSI6NDI2NTE1MDQwLCJpYXQiOjE3Njk5NTM1ODAsImV4cCI6MjA4NTUyOTU4MCwiaXNzIjoicHViLTAiLCJzdWIiOiJsaW5rLXJlZGlyZWN0In0.HY5Sa8EZTR5gSolf2EY3W2HDLjDa6XUmgeDK_FcBAJo?
View Email
Dr. Becky on the surprising overlap between great parenting and great leadership
lenny@substack.com2/1/2026
SubstackView this post on the web at https://www.lennysnewsletter.com/p/marc-andreessen-the-real-ai-boom
Marc Andreessen is a founder, investor, and co-founder of Netscape, as well as co-founder of the venture capital firm Andreessen Horowitz (a16z). In this conversation, we dig into why we’re living through a unique and one of the most incredible times in history, and what comes next.
Listen on YouTube [ https://substack.com/redirect/6a3044dc-cd61-4f25-a96f-8f758da4c5f1?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], Spotify [ https://substack.com/redirect/20339c3d-5241-46dd-a2e5-e6d4210ee43c?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], and Apple Podcasts [ https://substack.com/redirect/792d5bf5-2894-4d08-9432-d51f2c348e02?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
We discuss:
Why AI is arriving at the perfect moment to counter demographic collapse and declining productivity
How Marc has raised his 10-year-old kid to thrive in an AI-driven world
What’s actually going to happen with AI and jobs (spoiler: he thinks the panic is “totally off base”)
The “Mexican standoff” that’s happening between product managers, designers, and engineers
Why you should still learn to code (even with AI)
How to develop an “E-shaped” career that combines multiple skills, with AI as a force multiplier
The career advice he keeps coming back to (“Don’t be fungible”)
How AI can democratize one-on-one tutoring, potentially transforming education
His media diet: X and old books, nothing in between
Brought to you by:
DX [ https://substack.com/redirect/20fc0ba8-a6cf-43ef-a774-fa278014de70?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]—The developer intelligence platform designed by leading researchers
Brex [ https://substack.com/redirect/afa89738-d065-4902-89c9-802d0ebc6d0e?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]—The banking solution for startups
Datadog [ https://substack.com/redirect/96d28e99-ff78-43fc-80c2-a3c9f35aa837?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]—Now home to Eppo, the leading experimentation and feature flagging platform
Where to find Marc Andreessen:
• X: https://x.com/pmarca [ https://substack.com/redirect/eb997994-834f-42ee-9ed3-57bf83dfd4ab?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Substack: https://pmarca.substack.com [ https://substack.com/redirect/2d6e0cec-ccaf-4d8e-90db-9350f0d5afa5?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Andreessen Horowitz’s website: https://a16z.com [ https://substack.com/redirect/e22b9f15-d146-47da-a00d-b6c21b570b0e?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Andreessen Horowitz’s YouTube channel: https://www.youtube.com/@a16z [ https://substack.com/redirect/39e1c926-c262-42b1-9a35-67304f986c0d?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Referenced:
• Linus Torvalds on LinkedIn: https://www.linkedin.com/in/linustorvalds [ https://substack.com/redirect/e7594323-edef-4483-a5aa-e1edf9a0a801?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• The philosopher’s stone: https://en.wikipedia.org/wiki/Philosopher%27s_stone [ https://substack.com/redirect/f54f120d-ec57-49e8-85b0-4e05805ae526?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Alexander the Great: https://en.wikipedia.org/wiki/Alexander_the_Great [ https://substack.com/redirect/e91c9f26-3098-4943-a077-ed8ef3ce9713?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Aristotle: https://en.wikipedia.org/wiki/Aristotle [ https://substack.com/redirect/6053bb73-1e3b-4cb6-9828-e67f0e543788?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Bloom’s 2 sigma problem: https://en.wikipedia.org/wiki/Bloom%27s_2_sigma_problem [ https://substack.com/redirect/fb428923-b1b8-4a60-b682-0d68e7b1b19c?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Alpha School: https://alpha.school [ https://substack.com/redirect/66da5476-c92f-473a-a821-3f0dc82e6c0e?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• In Tech We Trust? A Debate with Peter Thiel and Marc Andreessen: https://a16z.com/in-tech-we-trust-a-debate-with-peter-thiel-and-marc-andreessen [ https://substack.com/redirect/858622c2-26b5-43ec-81e6-996f4444caf0?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• John Woo: https://en.wikipedia.org/wiki/John_Woo [ https://substack.com/redirect/a71732bb-64a0-4e55-8206-491b83865c3c?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Assembly: https://en.wikipedia.org/wiki/Assembly_language [ https://substack.com/redirect/cc1f26a5-34a0-441c-9b82-e1f9ec7a54e5?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• C programming language: https://en.wikipedia.org/wiki/C_(programming_language) [ https://substack.com/redirect/e1768d78-2044-4ff2-89f3-179399149a97?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Python: https://www.python.org [ https://substack.com/redirect/e5212389-5703-49f9-87ce-c0249fab6b8c?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Netscape: https://en.wikipedia.org/wiki/Netscape [ https://substack.com/redirect/fed9243b-a72c-43b3-a078-692bd38723a4?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Perl: https://www.perl.org [ https://substack.com/redirect/9f78c0e9-0800-4139-8f72-2a98247f7b68?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Scott Adams: https://en.wikipedia.org/wiki/Scott_Adams [ https://substack.com/redirect/20475732-1fe6-4044-b41a-d30a32b62d74?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Larry Summers’s website: https://larrysummers.com [ https://substack.com/redirect/6722bcef-28e1-48c8-8926-ccf088dcef97?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Nano Banana: https://gemini.google/overview/image-generation [ https://substack.com/redirect/823a0ae7-7c05-4e79-8d61-7ae69fa6d65b?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Bitcoin: https://bitcoin.org [ https://substack.com/redirect/6150e076-3af9-4e14-bb64-62f5f60a3f21?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Ethereum: https://ethereum.org [ https://substack.com/redirect/1afc62ff-937a-412a-8c7c-d1ad5169228f?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Satoshi Nakamoto: https://en.wikipedia.org/wiki/Satoshi_Nakamoto [ https://substack.com/redirect/ea8bc554-4a5f-40c8-8d5b-2078f1b7a38c?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Inside ChatGPT: The fastest-growing product in history | Nick Turley (Head of ChatGPT at OpenAI): https://www.lennysnewsletter.com/p/inside-chatgpt-nick-turley [ https://substack.com/redirect/13e0d33b-2a46-4f02-b7f0-02e806f8abb0?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Anthropic co-founder on quitting OpenAI, AGI predictions, $100M talent wars, 20% unemployment, and the nightmare scenarios keeping him up at night | Ben Mann: https://www.lennysnewsletter.com/p/anthropic-co-founder-benjamin-mann [ https://substack.com/redirect/c8f0fe90-2244-4510-acfe-6624f87e9127?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Inside Google’s AI turnaround: The rise of AI Mode, strategy behind AI Overviews, and their vision for AI-powered search | Robby Stein (VP of Product, Google Search): https://www.lennysnewsletter.com/p/how-google-built-ai-mode-in-under-a-year [ https://substack.com/redirect/ac77f742-9d76-4fdb-ac70-fe38368b391d?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• DeepSeek: https://www.deepseek.com [ https://substack.com/redirect/4045a9af-476c-4fa4-886f-56d2739d5bb3?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Cowork: https://support.claude.com/en/articles/13345190-getting-started-with-cowork [ https://substack.com/redirect/670a125f-b028-4c1a-8808-8e1b634c1a34?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Definite vs. indefinite thinking: Notes from Zero to One by Peter Thiel: https://boxkitemachine.net/posts/zero-to-one-peter-thiel-definite-vs-indefinite-thinking [ https://substack.com/redirect/ad70e35a-40d4-4fd9-a523-42112ff2fb0f?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Henry Ford: https://www.thehenryford.org/explore/stories-of-innovation/visionaries/henry-ford [ https://substack.com/redirect/792fa264-53eb-4696-8ee5-8db43477bac2?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Lex Fridman Podcast: https://lexfridman.com/podcast [ https://substack.com/redirect/366eb253-3da6-4c31-9e67-ee8985b89f6b?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• $46B of hard truths from Ben Horowitz: Why founders fail and why you need to run toward fear (a16z co-founder): https://www.lennysnewsletter.com/p/46b-of-hard-truths-from-ben-horowitz [ https://substack.com/redirect/58e04a45-9b35-4648-b893-bcecd323273e?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Eddington: https://www.imdb.com/title/tt31176520 [ https://substack.com/redirect/4eb022e9-27c5-41e2-ad44-ddf1fe90ec04?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Joaquin Phoenix: https://en.wikipedia.org/wiki/Joaquin_Phoenix [ https://substack.com/redirect/daa462fb-61e0-4232-8170-92b74cb1b590?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Pedro Pascal: https://en.wikipedia.org/wiki/Pedro_Pascal [ https://substack.com/redirect/137092da-1d4b-49ee-ab8b-18e0d9ada854?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• George Floyd: https://en.wikipedia.org/wiki/George_Floyd [ https://substack.com/redirect/7463a129-8621-4026-8705-7aeb705104ba?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Replit: https://replit.com [ https://substack.com/redirect/c985876c-0252-4524-8f2a-98f2c7ffabba?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Behind the product: Replit | Amjad Masad (co-founder and CEO): https://www.lennysnewsletter.com/p/behind-the-product-replit-amjad-masad [ https://substack.com/redirect/fd36ca84-a169-4519-abb1-3661ed7fa828?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Grok Bad Rudi: https://grok.com/badrudi [ https://substack.com/redirect/dbd17792-6e8a-468a-8aa1-9adb7dc16ee0?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Wispr Flow: https://wisprflow.ai [ https://substack.com/redirect/d48c5be6-627a-4aa2-8e4f-abbf95ad3e42?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Star Trek: The Next Generation: https://www.imdb.com/title/tt0092455 [ https://substack.com/redirect/0961769c-83be-4b59-8781-5a66470e4e7e?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Star Trek: Starfleet Academy: https://www.imdb.com/title/tt8622160 [ https://substack.com/redirect/fa731136-5a71-4c89-ac91-65d4e357831a?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• a16z: The Power Brokers: https://www.notboring.co/p/a16z-the-power-brokers [ https://substack.com/redirect/4a42e497-a702-489b-8bba-9a8fb6a69832?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Production and marketing by https://penname.co/ [ https://substack.com/redirect/d5b631c5-f2cf-4459-91d9-fc9820f6e10a?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com [ mailto:podcast@lennyrachitsky.com ].
Lenny may be an investor in the companies discussed.
My biggest takeaways from this conversation:...
Unsubscribe https://substack.com/redirect/2/eyJlIjoiaHR0cHM6Ly93d3cubGVubnlzbmV3c2xldHRlci5jb20vYWN0aW9uL2Rpc2FibGVfZW1haWw_dG9rZW49ZXlKMWMyVnlYMmxrSWpvME1qWTFNVFV3TkRBc0luQnZjM1JmYVdRaU9qRTROVE16T0RRNU55d2lhV0YwSWpveE56WTVOamswTWprd0xDSmxlSEFpT2pFNE1ERXlNekF5T1RBc0ltbHpjeUk2SW5CMVlpMHhNRGcwTlNJc0luTjFZaUk2SW1ScGMyRmliR1ZmWlcxaGFXd2lmUS45bUpidmNHYWNqbDFXa1R2TjBmanpLREJCall3Y0F3VXYyR09JcWRiYkJZIiwicCI6MTg1MzM4NDk3LCJzIjoxMDg0NSwiZiI6dHJ1ZSwidSI6NDI2NTE1MDQwLCJpYXQiOjE3Njk2OTQyOTAsImV4cCI6MjA4NTI3MDI5MCwiaXNzIjoicHViLTAiLCJzdWIiOiJsaW5rLXJlZGlyZWN0In0.cQsCjxzsTgOM3Qzr1swxLU4cgXlMgroA_XA5r3k9tdM?
View Email
Marc Andreessen: The real AI boom hasn’t even started yet
lenny@substack.com1/29/2026
SubstackView this post on the web at https://www.lennysnewsletter.com/p/product-pass-drop-canva-elevenlabs
👋 Hey there, I’m Lenny. Each week, I answer reader questions about building product, driving growth, and accelerating your career. For more: Lenny’s Podcast [ https://substack.com/redirect/846537e0-1903-461a-8d6c-ecaf16d43c8f?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] | How I AI [ https://substack.com/redirect/2c1b9a1e-91ab-498c-acae-12674a91f68a?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] | Lennybot [ https://substack.com/redirect/b0220cca-d8a8-4032-bcf8-3523c9e6de5b?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] | Lenny’s Reads [ https://substack.com/redirect/c1f9ba62-404b-466c-b578-09c7e427af23?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] | Favorite AI and PM courses [ https://substack.com/redirect/f7fb2c29-c33c-48b4-a607-8eccb097bffc?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] | Favorite communication course [ https://substack.com/redirect/60bef0ad-bf42-44a6-a784-0050a166933e?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
I’m excited to welcome seven new premium partners to the Lenny’s Newsletter Product Pass [ https://substack.com/redirect/daf3b2a0-db82-4579-b97f-b6ca6479de9e?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]—bringing the total value of your paid newsletter subscription to over $25,000.
→ Already a paid subscriber? Grab your free products here [ https://substack.com/redirect/daf3b2a0-db82-4579-b97f-b6ca6479de9e?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ].
→ Not yet a subscriber? Subscribe [ https://substack.com/redirect/022e398d-cab2-4ceb-ac33-e10dadc6ebd6?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] and then grab your free products here [ https://substack.com/redirect/daf3b2a0-db82-4579-b97f-b6ca6479de9e?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ].
My goal with the Product Pass [ https://substack.com/redirect/daf3b2a0-db82-4579-b97f-b6ca6479de9e?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] is to get you to actually experience the most important, cutting-edge, beautifully crafted products for yourself: to stop scrolling and start building.
As I’ve said before, there’s a growing divide (in terms of career opportunities, financial outcomes, loving your job) between the people who embrace these magical new tools and benefit from them, and those who stay business-as-usual and get left behind. My mission is to make sure you’re in that first group.
Your paid subscription gets you access to the world’s most popular product newsletter [ https://substack.com/redirect/2c222e54-2c71-42db-93fa-0b92ac44d2eb?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], podcast [ https://substack.com/redirect/846537e0-1903-461a-8d6c-ecaf16d43c8f?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], and global product community [ https://substack.com/redirect/e0a941a6-54c3-45ea-a95c-6ef89e029b88?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] (with local meetups, mentorship programs, AMAs, and more), and now, also the entire stack of tools you need to become an AI-native builder—for just $200-$350 a year.
This collection includes only products that I love, and have carefully handpicked. There are dozens of companies that have asked to join this bundle that I’m holding off on, to get you the highest concentration of goodness. Every quarter (or so), we’ll continue rotating products in and out so that we can keep this collection fresh and awesome.
Many readers expense this subscription out of their workplace’s learning and development budget. Here’s an email you can send to your manager [ https://substack.com/redirect/25249211-15b5-40ac-9702-1615c23096e0?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]. These deals are exclusively provided to subscribers of this newsletter—you won’t find anything like this anywhere else.
Subscribe here [ https://substack.com/redirect/022e398d-cab2-4ceb-ac33-e10dadc6ebd6?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], and grab your free products here [ https://substack.com/redirect/daf3b2a0-db82-4579-b97f-b6ca6479de9e?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]. See offer details below for full terms and conditions (please read before subscribing).
What are the new products?
In addition to the 16 products [ https://substack.com/redirect/daf3b2a0-db82-4579-b97f-b6ca6479de9e?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] already included with your subscription, here’s what you get starting today:
1. Manus [ https://substack.com/redirect/56d0d270-fc18-4c5c-bf46-13e4fe479ad2?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]—1 year free of Manus, with 4,000 credits per month ($240 value)
Manus is an autonomous Al agent platform from Meta that executes complex tasks independently. Delegate workflows such as data analysis, content creation, and research to Al agents that plan and complete tasks without constant supervision.
Examples of how people use Manus:
Scraping a competitor’s Meta ads [ https://substack.com/redirect/eca93fb4-90a3-4140-885a-43d048f6aa4e?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Analyzing SEO keywords [ https://substack.com/redirect/ce2c09b4-667c-4253-b13b-4e92b1540bec?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Researching AGI timelines [ https://substack.com/redirect/dd69e90b-ccd8-473d-b9d1-ac1344a4c8c8?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Doing competitive analysis [ https://substack.com/redirect/4b5ee713-706e-411d-8d6c-53c6cffaf456?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Designing a flower bouquet [ https://substack.com/redirect/ae9fc330-485d-4ae1-9cac-9dd5776e6472?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
2. Amp [ https://substack.com/redirect/2f3682cf-1c5e-45ec-8857-0a85954d10b9?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]—1 year of free Amp credits, $15/day ($1,825 value)
Amp is the frontier coding agent for your terminal and editor. It uses state-of-the-art models, switching between them based on what each task needs. Start a thread, describe what you want, and Amp figures out the rest: reading your codebase, running commands, editing files, and iterating until it works. Save and share threads like you would code.
Examples of how people use Amp:
Building full-stack features in hours: Solo founders have shipped complete features, landing pages, dashboards, and data visualizations—across React, Tailwind, and PostgreSQL—in a single afternoon. Amp handles frontend, backend, and database layers without context switching.
Large-scale refactoring: Remove deprecated systems spanning database schemas, API routes, and UI components. Amp plans the migration, generates scripts, updates all callsites, runs tests, and commits clean code.
Production debugging: Amp connects to Sentry, pulls stack traces, traces bugs across multiple code paths, and ships fixes. What used to be hours of log-diving becomes a single thread.
Automated browser testing: Amp runs through user flows in a real browser—sign-in, forms, checkout—takes screenshots, and writes tests that verify behavior. No manual QA scripts required.
Research-then-build workflows: Need to integrate a new API or library? Amp reads the docs, finds examples, and implements. It knows when to search the web and when to write code.
3. Factory [ https://substack.com/redirect/283a2061-5e1c-4722-b498-8b4c9fc94ef1?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]—1 year free of Factory Pro ($240 value)
Factory builds Droids, software development agents that live in your IDE, terminal, and web browser. Use Droids to plan, build, and deploy software at scale. Customize them with plugins, skills, MCP, and any model of your preference.
Examples of how people use Factory:
Inbox monitoring software—backend and frontend [ https://substack.com/redirect/799dd7e0-b1b2-435c-9d6d-278052ac31af?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Factory-wrapped and custom CLIs [ https://substack.com/redirect/93a696a0-fd98-4165-a280-f17dc948d3ad?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Personal diff viewer [ https://substack.com/redirect/89ecc0af-50d9-4d2c-bf8d-e1f39351c955?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
CI runner [ https://substack.com/redirect/d2779064-b069-451a-873b-00edb675a494?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
4. Railway [ https://substack.com/redirect/ae08db52-8bfc-443e-a8bb-2ef3ed5c80b3?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]—1 year free of Railway Pro ($240 value)
Railway is the intelligent cloud provider that lets you ship software peacefully. It integrates with your existing agents to host production-ready applications with one-click simplicity.
Examples of how people use Railway:
Kernel [ https://substack.com/redirect/0170f59e-37f4-4baa-8784-1888fcea0310?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]: An AI YC startup that powers cloud browser infrastructure for over 1,000 AI agent companies by hosting and scaling their API, dashboard, and websockets on Railway.
Around 90,000 users host their entire n8n stack on Railway using one of the most popular templates [ https://substack.com/redirect/38263500-b9cd-4481-8e2e-b23669a70f0c?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] for a one-click deploy of n8n. Or self-host Metabase [ https://substack.com/redirect/3ad0de40-772a-4991-a79c-3fa607404a0a?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] with templates at a fraction of the cost, without the burden.
Railway powers Every [ https://substack.com/redirect/2e445657-b788-4a7f-9e0f-ee769a711adb?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], building AI-native operations and products. Every moved to Railway and cut their cloud bill by 5x [ https://substack.com/redirect/0eed50fa-c86e-4a90-8143-884245b9118d?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] while shipping faster with the visual canvas.
5. Framer [ https://substack.com/redirect/3293a050-cd77-452c-a2b1-b6e2fe4ed8cd?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]—1 year free of Framer Pro ($360 value)
Framer is a design-first website builder that lets you build, ship, and manage your company’s site without help from engineering. It comes with an integrated CMS with everything you need for SEO, analytics, A/B testing, hosting, and security.
Examples of how people use Framer:
Building a campaign website, with Perplexity, for Cristiano Ronaldo [ https://substack.com/redirect/0424e704-0020-471e-b028-5e74aa41e0fa?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Hosting a marketing site alongside a Next.js app [ https://substack.com/redirect/f9db4097-b67d-41cc-8cee-8e0e1bf7d5c0?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] (without eng being involved)
Designing and building landing pages [ https://substack.com/redirect/2a781750-5652-4b6c-9331-29694dd63871?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Creating brand and website guidelines, then building with them [ https://substack.com/redirect/cf4c7c72-37b7-49b6-95b1-d87479189ce7?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
A travel website documenting a trip to Japan [ https://substack.com/redirect/5f5a13ad-01ca-4d93-a323-aa698129db1d?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
6. Canva Business [ https://substack.com/redirect/e13b8e3f-077e-48e9-97c4-c986d6bacf94?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]—1 year free of Canva Business ($200 value) [Insiders only]
Canva is an end-to-end visual communication platform designed for every kind of work, from social media posts and presentations to marketing campaigns and brand assets. Their new tier, Canva Business [ https://substack.com/redirect/e13b8e3f-077e-48e9-97c4-c986d6bacf94?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] (which is what you’re getting), is designed for individuals and teams looking to grow their business. It includes access to real-time ad performance insights with Canva Grow, interactive data visualization with Flourish [ https://substack.com/redirect/881bbf4f-163b-4788-9561-249d59216d47?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], AI image and video generation with Leonardo.Ai [ https://substack.com/redirect/265e811c-634b-46b5-b986-eaa7d6e26733?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], and a 10% discount on print orders*. You also get Affinity [ https://substack.com/redirect/27385474-f7f4-4df2-8c0b-6c1b7384681d?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] for free to empower your professional design work.
*Available only where Canva Print is offered. Cannot be combined with other offers.
Examples of how people use Canva Business:
Creating high-performing ads with insights [ https://substack.com/redirect/d11d9f89-4664-45d1-b8f5-489b4c208a91?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Building engaging client presentations [ https://substack.com/redirect/c7834968-7978-495e-a5b2-43f83b328afe?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Building websites for business launch [ https://substack.com/redirect/8b8ba2be-19c5-4585-819a-bfc6af12fdf8?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Creating short, snappy video reels with AI [ https://substack.com/redirect/fff3bcdc-3edb-4716-a0a3-e9034b0c40c6?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Creating multi-channel brand assets for marketing campaigns [ https://substack.com/redirect/3b427643-e72b-4a1e-a3a5-376202c14c49?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
7. ElevenLabs [ https://substack.com/redirect/5dcf9fcb-07dc-4a75-ab75-b15862417d8c?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]—1 year free of ElevenLabs Creator Plan ($264 value) [Insiders only]
ElevenLabs is an all-in-one AI creative platform to bring your content to life. A single platform to generate, edit, and localize premium audio and video in minutes, powering millions of creators, marketing teams, and media companies worldwide.
Examples of how people use ElevenLabs:
Meta [ https://substack.com/redirect/86361aae-2a69-4f0d-8241-205bb44adaa5?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] uses ElevenLabs to power expressive, scalable audio across Instagram, Horizon, and more, from dubbing Reels in local languages to generating music and character voices in Horizon.
Nvidia [ https://substack.com/redirect/e90fb2bf-3e52-4c68-951e-0712d1599a45?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] uses ElevenLabs to deliver multilingual marketing content.
Harvey [ https://substack.com/redirect/d50fa7bb-d500-4326-a6c2-4ef065a43eb1?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] uses ElevenLabs text-to-speech and speech-to-text to enable every lawyer to engage with Harvey in their own language and context.
Duolingo [ https://substack.com/redirect/f97aa8ba-f921-450d-88f9-d8780b67eab3?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] powers character voices and multilingual marketing content with ElevenLabs.
Mozart AI [ https://substack.com/redirect/1f0c2eab-7237-4269-b84b-15a56a79395a?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] uses Eleven Music to power stem editing and full song creation for their users.
How do I get access to these free products?
Become an Annual [ https://substack.com/redirect/5be63b9e-b982-4204-bab5-36411246de50?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] or Insider [ https://substack.com/redirect/fe712734-3797-483f-b2d3-4aa5d508d4bb?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] subscriber and then grab your codes here [ https://substack.com/redirect/daf3b2a0-db82-4579-b97f-b6ca6479de9e?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ].
If I’m already a paid subscriber, do I get access to the products?
Yep! The same rules below apply to both new and existing subscribers.
What’s the difference between the Annual and Insider tiers?
Since we don’t have unlimited free product codes, we occasionally run out of the more popular products. To address this, we introduced an Insider tier:
Insider-tier subscribers [ https://substack.com/redirect/fe712734-3797-483f-b2d3-4aa5d508d4bb?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] ($350/year) get priority access to all available products—we set aside a dedicated pool of codes for this tier. Some products (like Canva Business, ElevenLabs, and Lovable) are exclusively available to Insiders.
Annual subscribers [ https://substack.com/redirect/5be63b9e-b982-4204-bab5-36411246de50?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] ($200/year) get general access to the majority of products (currently, 16 out of 23) on a first-come, first-serve basis. We do our best to get plenty of codes, but once they’re gone, they’re gone.
You can always check the current status of all available products here [ https://substack.com/redirect/daf3b2a0-db82-4579-b97f-b6ca6479de9e?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]. Monthly subscribers do not get access to these products.
Note: The Insider subscription gives you priority access to all available products. The previous iteration of the Insider tier guaranteed access to every product. If you became an Insider prior to 1/24/26, you are still guaranteed access to every product in our collection until those deals expire (typically six months after launch). New Insider subscribers get priority access—meaning you’ll get front-of-the-line access to every product, and we set aside a dedicated pool of codes for this tier. In practice, you’ll almost certainly get every product you want, along with Insider-only exclusive products. We made this change because some of the newer products in the collection weren’t able to give us enough codes to cover every single Insider indefinitely, and we’d rather include these products in the bundle than not.
If you have questions or run into any issues, send us an email at support@lennyrachitsky.com [ mailto:support@lennyrachitsky.com ].
What else should I know before I subscribe?
You must be a new customer of the products to take advantage of the free year. If you’ve already paid for one of the products before (monthly or yearly) or redeemed one of our offer codes for that product, you won’t be able to get a free additional year of that product.
We may run out of codes for a product. Your code is only secured once you claim it [ https://substack.com/redirect/daf3b2a0-db82-4579-b97f-b6ca6479de9e?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]. You need to claim each code individually, so hop on the products you are most excited about. Insider-tier subscribers get priority access, so if you want to reduce your stress levels, become an Insider [ https://substack.com/redirect/fe712734-3797-483f-b2d3-4aa5d508d4bb?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ].
All sales are final. We won’t issue a refund if any products are out by the time you claim them. The deal is already so good, even if a couple of products are unavailable. If you request a chargeback for your subscription, all of your codes will be deactivated.
The product offers in the current collection will expire six months from this launch (on July 27th). This gives us room to rotate new products in and out of the collection. Make sure to redeem the deals before they expire.
I can’t wait to hear about what you build with these products.
Enjoy!
If you’re finding this newsletter valuable, share it with a friend, and consider subscribing if you haven’t already. There are group discounts [ https://substack.com/redirect/38e6272f-f424-4424-9bab-db31817837f8?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], gift options [ https://substack.com/redirect/7a838664-37cb-4fdd-8055-04b863eb0d9b?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], and referral bonuses [ https://substack.com/redirect/5f361bd5-9729-43a4-96a3-38f5535644c7?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] available.
Sincerely,
Lenny 👋
Unsubscribe https://substack.com/redirect/2/eyJlIjoiaHR0cHM6Ly93d3cubGVubnlzbmV3c2xldHRlci5jb20vYWN0aW9uL2Rpc2FibGVfZW1haWw_dG9rZW49ZXlKMWMyVnlYMmxrSWpvME1qWTFNVFV3TkRBc0luQnZjM1JmYVdRaU9qRTRORFE1Tmprd05Td2lhV0YwSWpveE56WTVOVE16TVRNd0xDSmxlSEFpT2pFNE1ERXdOamt4TXpBc0ltbHpjeUk2SW5CMVlpMHhNRGcwTlNJc0luTjFZaUk2SW1ScGMyRmliR1ZmWlcxaGFXd2lmUS5KSUFRVW5NdlhxaHZrVVgySkgxT2VCcm12TWdYamtLQWVEN1hnWk9aekZFIiwicCI6MTg0NDk2OTA1LCJzIjoxMDg0NSwiZiI6dHJ1ZSwidSI6NDI2NTE1MDQwLCJpYXQiOjE3Njk1MzMxMzAsImV4cCI6MjA4NTEwOTEzMCwiaXNzIjoicHViLTAiLCJzdWIiOiJsaW5rLXJlZGlyZWN0In0.ZoCfxLnPnXSZbWzQKZ8j_gpwoCc1qFKC4_t0KCKoIaQ?
View Email
Product Pass drop: Canva, ElevenLabs, Manus, Factory, Amp, Railway, Framer—now free with your paid subscription
lenny@substack.com1/27/2026
SubstackView this post on the web at https://www.lennysnewsletter.com/p/why-your-product-stopped-growing
Jason Cohen is a four-time founder (including two unicorns, one being WP Engine) and an investor in over 60 startups, and has been sharing his lessons on company building at A Smart Bear for nearly 20 years. In this episode, Jason shares his methodical five-step framework for diagnosing stalled growth—a problem that faces almost every team.
Listen on YouTube [ https://substack.com/redirect/307e05ad-85ed-4459-8477-f4e70446652d?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], Spotify [ https://substack.com/redirect/a7cc4fff-a44d-4d72-985f-c421cd587fba?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], and Apple Podcasts [ https://substack.com/redirect/12199e5a-1fec-4a8b-9130-c1c4229bda27?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
We discuss:
Jason’s five-step framework: logo retention, pricing, NRR, marketing channels, target market
A small tweak that’ll double response rates on your cancellation surveys
Why “it’s too expensive” is almost never the real reason customers cancel
The “elephant curve” of growth
How repositioning the same product can increase revenue 8x
When to reconsider if growth is even the right goal for your business
Brought to you by:
10Web [ https://substack.com/redirect/3c303c79-cd92-46fd-b0d9-e06bddf0045d?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]—Vibe coding platform as an API
Strella [ https://substack.com/redirect/e1beff84-6487-4781-89c6-d92d893f05eb?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]—The AI-powered customer research platform
Brex [ https://substack.com/redirect/2eeeab06-32ff-423f-b9c7-6132a88d71b5?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]—The banking solution for startups
Where to find Jason Cohen:
• Preorder Jason’s book: https://preorder.hiddenmultipliers.com/ [ https://substack.com/redirect/c836226a-b560-46c5-9ed6-768ff063bcf1?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• X: https://x.com/asmartbear [ https://substack.com/redirect/68281e47-2f66-4ab4-9732-b12e05c45f77?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• LinkedIn: https://www.linkedin.com/in/jasoncohen [ https://substack.com/redirect/32d3da1f-286c-4316-bef7-cc4942f34147?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Blog: https://longform.asmartbear.com [ https://substack.com/redirect/dd048316-8a27-45df-b405-bda58975efe4?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Website: https://wpengine.com [ https://substack.com/redirect/6abea9fc-2a5b-4bad-9bd8-e791b8b2561c?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Referenced:
• Tyler Cowen’s website: https://tylercowen.com [ https://substack.com/redirect/06381953-af1f-4263-bb14-f5986fa067dd?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• How to Perform a Customer Churn Analysis (and Why You Should): https://www.groovehq.com/blog/learn-from-customer-churn [ https://substack.com/redirect/82afce87-e23d-4a76-b749-bd1a4c93d845?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Linear: https://linear.app [ https://substack.com/redirect/19685172-ba92-4147-a4a9-895bfb28b451?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Jira: https://www.atlassian.com/software/jira [ https://substack.com/redirect/5a94b205-41e5-4ccd-9ce3-40ba7f088941?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Patrick Campbell’s post on X about pricing: https://x.com/Patticus/status/1702313260547006942 [ https://substack.com/redirect/ce1ddcc7-5ca4-4dce-b15f-aad9ee6a26b7?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• The art and science of pricing | Madhavan Ramanujam (Monetizing Innovation, Simon-Kucher): https://www.lennysnewsletter.com/p/the-art-and-science-of-pricing-madhavan [ https://substack.com/redirect/71bd6aa8-1974-4f88-8b01-ab83e7ddb11d?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Pricing your AI product: Lessons from 400+ companies and 50 unicorns | Madhavan Ramanujam: https://www.lennysnewsletter.com/p/pricing-and-scaling-your-ai-product-madhavan-ramanujam [ https://substack.com/redirect/017cbc1e-5b9d-42b4-8b19-b172ef6e2da1?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Pricing your SaaS product: https://www.lennysnewsletter.com/p/saas-pricing-strategy [ https://substack.com/redirect/e42b0a79-9a31-42cc-9567-e0c2158c33fb?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• M&A, competition, pricing, and investing | Julia Schottenstein (dbt Labs): https://www.lennysnewsletter.com/p/m-and-a-competition-pricing-and-investing [ https://substack.com/redirect/29fe1b5c-ae0f-455e-ade3-7659f5587779?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• “Sell the alpha, not the feature”: The enterprise sales playbook for $1M to $10M ARR | Jen Abel: https://www.lennysnewsletter.com/p/the-enterprise-sales-playbook-1m-to-10m-arr [ https://substack.com/redirect/8720f06b-c834-4bff-adeb-23e8d5237338?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Buffer: https://buffer.com [ https://substack.com/redirect/c8c8cb9e-e88a-4a64-bb7b-06e0066f8ea5?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• AG1: https://drinkag1.com [ https://substack.com/redirect/f77fb586-7893-4e5a-ab72-3e76333bb53a?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• How to find hidden growth opportunities in your product | Albert Cheng (Duolingo, Grammarly, Chess.com): https://www.lennysnewsletter.com/p/how-to-find-hidden-growth-opportunities-albert-cheng [ https://substack.com/redirect/914d18b2-743e-4802-a308-c4684c02fba7?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• How Duolingo reignited user growth: https://www.lennysnewsletter.com/p/how-duolingo-reignited-user-growth [ https://substack.com/redirect/a35ca1d3-95be-4fd7-86fd-4c6a0f75de03?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• The Elephant in the room: The myth of exponential hypergrowth: https://longform.asmartbear.com/exponential-growth [ https://substack.com/redirect/566bc506-fba6-4d76-b3ec-9c07e7834983?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• HubSpot: https://www.hubspot.com [ https://substack.com/redirect/c6b85438-157d-4252-b00c-46be8132d744?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Zigging vs. zagging: How HubSpot built a $30B company | Dharmesh Shah (co-founder/CTO): https://www.lennysnewsletter.com/p/lessons-from-30-years-of-building [ https://substack.com/redirect/82ad32a0-942e-4de8-81db-dd2794b2cb92?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Adjacency Matrix: How to expand after PMF: https://longform.asmartbear.com/adjacency/ [ https://substack.com/redirect/d0cfd5e0-6f65-4ba6-b549-1dadd83f8e78?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Ecosystem is the next big growth channel: https://www.lennysnewsletter.com/p/ecosystem-is-the-next-big-growth [ https://substack.com/redirect/e5e7076e-f746-408d-9659-61e40be17d32?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• ChatGPT apps are about to be the next big distribution channel: Here’s how to build one: https://www.lennysnewsletter.com/p/chatgpt-apps-are-about-to-be-the [ https://substack.com/redirect/659eb5b9-ca2e-4c54-a35b-d75c84c0219b?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling): https://www.lennysnewsletter.com/p/10-contrarian-leadership-truths [ https://substack.com/redirect/3e27b211-9423-4a4b-b02d-7c1dbea5fb5d?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Breaking the rules of growth: Why Shopify bans KPIs, optimizes for churn, prioritizes intuition, and builds toward a 100-year vision | Archie Abrams (VP Product, Head of Growth at Shopify): https://www.lennysnewsletter.com/p/shopifys-growth-archie-abrams [ https://substack.com/redirect/3091d71d-dc3a-40b6-b662-a146387353fd?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Geoffrey Moore on finding your beachhead, crossing the chasm, and dominating a market: https://www.lennysnewsletter.com/p/geoffrey-moore-on-finding-your-beachhead [ https://substack.com/redirect/e7ca3060-daa4-40cd-bee8-bae098f1fea2?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• ER on Prime Video: https://www.amazon.com/ER-Season-1/dp/B0FWK5WJQ4 [ https://substack.com/redirect/491aa6a5-611f-4b1e-84c3-15fa3bbdbac3?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• The Pitt on Prime Video: https://www.amazon.com/The-Pitt-Season-1/dp/B0DNRR8QWD [ https://substack.com/redirect/e8e36f2a-ee12-44fb-a584-795b5545c1cf?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Wispr Flow: https://wisprflow.ai [ https://substack.com/redirect/67dcd8f1-e9ba-4603-ac4a-53adeac2205b?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Anker: https://www.anker.com [ https://substack.com/redirect/d89f0eef-70a0-4bdb-9bc5-4d58594135bc?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Recommended books:
• Will: https://www.amazon.com/Will-Smith/dp/1984877925 [ https://substack.com/redirect/b4216848-38cb-4771-b11a-028265ab316b?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Monetizing Innovation: How Smart Companies Design the Product Around the Price: https://www.amazon.com/Monetizing-Innovation-Companies-Design-Product/dp/1119240867 [ https://substack.com/redirect/a71e9316-9fa7-47be-a6be-8fa0b0950f03?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Hidden Multipliers: Small Things That Accelerate Growth: https://preorder.hiddenmultipliers.com [ https://substack.com/redirect/a7cdd436-c300-4d7f-bcb5-093f455f6702?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• On Writing Well: The Essential Guide to Mastering Nonfiction Writing and Effective Communication: https://www.amazon.com/Writing-Well-Classic-Guide-Nonfiction/dp/0060891548 [ https://substack.com/redirect/03bee261-a463-4f85-abf7-cbdc42c890e1?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Crossing the Chasm, 3rd Edition: The Updated Version of the Insightful Guide on Bringing Cutting-Edge Products to the Mainstream: https://www.amazon.com/Crossing-Chasm-3rd-Disruptive-Mainstream/dp/0062292986 [ https://substack.com/redirect/ead40d2f-40d1-4458-a82d-d064dfc45e3d?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Production and marketing by https://penname.co/ [ https://substack.com/redirect/d64fc71a-69ec-4b23-8cc2-64cf2291d33b?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com [ mailto:podcast@lennyrachitsky.com ].
Lenny may be an investor in the companies discussed.
My biggest takeaways from this conversation:...
Unsubscribe https://substack.com/redirect/2/eyJlIjoiaHR0cHM6Ly93d3cubGVubnlzbmV3c2xldHRlci5jb20vYWN0aW9uL2Rpc2FibGVfZW1haWw_dG9rZW49ZXlKMWMyVnlYMmxrSWpvME1qWTFNVFV3TkRBc0luQnZjM1JmYVdRaU9qRTRORFUzTmpFd015d2lhV0YwSWpveE56WTVNelE0TnpJM0xDSmxlSEFpT2pFNE1EQTRPRFEzTWpjc0ltbHpjeUk2SW5CMVlpMHhNRGcwTlNJc0luTjFZaUk2SW1ScGMyRmliR1ZmWlcxaGFXd2lmUS5CeTdFWmpJU3d4alNWY3dtam9kSWlGRW9HSlV0clRWXzZMUWd1LUlRX1RrIiwicCI6MTg0NTc2MTAzLCJzIjoxMDg0NSwiZiI6dHJ1ZSwidSI6NDI2NTE1MDQwLCJpYXQiOjE3NjkzNDg3MjcsImV4cCI6MjA4NDkyNDcyNywiaXNzIjoicHViLTAiLCJzdWIiOiJsaW5rLXJlZGlyZWN0In0.6y9yZT1vwVRMs3MSJDJ7cMjA2QA41bGWGk4WJuJfRH0?
View Email
Why your product stopped growing (and the 5-step framework to restart it) | Jason Cohen
lenny@substack.com1/25/2026
SubstackView this post on the web at https://www.lennysnewsletter.com/p/chatgpt-apps-are-about-to-be-the
👋 Hey there, I’m Lenny. Each week, I tackle reader questions about building product, driving growth, and accelerating your career. For more: Lennybot [ https://substack.com/redirect/f08904b3-09ec-4ab4-aeb8-ef4fbc3c5bcf?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] | Lenny’s Podcast [ https://substack.com/redirect/c5e98956-da47-42ee-8789-0ccfe9fde614?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] | How I AI [ https://substack.com/redirect/cce7e61d-b96e-465d-9f66-5facae442f65?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] | Lenny’s Reads [ https://substack.com/redirect/d7727983-177b-464e-8f65-2f76b2fd052d?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] | Favorite AI and PM courses [ https://substack.com/redirect/388ec7fa-24f8-4021-be59-3593513c2337?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] | Favorite communication course [ https://substack.com/redirect/7a3a0903-3371-4593-ac2c-558b178e5d64?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Subscribers get 19 premium products for free for one year: Lovable, Replit, Gamma, n8n, Bolt, Devin, Wispr Flow, Descript, Linear, PostHog, Superhuman, Granola, Warp, Perplexity, Raycast, Magic Patterns, Mobbin, ChatPRD, and Stripe Atlas [ https://substack.com/redirect/be2e6c26-e9bc-4bc4-bf7c-a154b3e04364?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] (terms apply [ https://substack.com/redirect/76efb16f-82bc-44eb-a830-b77db5a70759?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]). Subscribe now [ https://substack.com/redirect/8447e7e1-6386-4bbc-b5d0-68b64d5cb29f?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ].
My many-time collaborator—and author of my 2nd and 12th most popular posts of all time—is back, and it’s a banger. If you’re looking for alpha in growing your product, this post is for you. I’ll keep my intro short and get you right into the post.
For more from Colin, find him on LinkedIn [ https://substack.com/redirect/a4bca6a4-cf1f-4e31-bbd0-e40e6d453df0?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], check out his killer course [ https://substack.com/redirect/1f0aad78-aa9c-438a-807d-7bf9acd95052?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], and join this free Lightning Lesson [ https://substack.com/redirect/4c5284d2-0cc3-4d74-ad90-d5d32bf52767?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] on January 30th to get a hands-on, live look at building your first ChatGPT app.
P.S. You can listen to this post in convenient podcast form: Spotify [ https://substack.com/redirect/859bd7f1-f04d-4507-8743-fe9fc2b3bf81?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] / Apple [ https://substack.com/redirect/fe73bb4a-9680-4d03-8a22-fe9d2d052709?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] / YouTube [ https://substack.com/redirect/ada93ec4-36fe-4656-8731-00855726f816?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ].
A few months ago, if you asked ChatGPT to help you book a flight to Paris, you’d get a helpful list of recommendations: airline breakdowns, price ranges, maybe some tips on timing. Then you’d leave ChatGPT, open a travel site, and start your search from scratch.
Now you can say, “Help me find a good flight to Paris from Toronto,” and an interactive widget appears directly inside your conversation. You browse flight options, compare prices, and book, all without ever leaving the chat.
The strategy is simple: instead of ChatGPT responding with text and sending the user elsewhere, it will now surface interactive widgets from third-party apps directly in a conversation, letting users transact inside of ChatGPT (and over time, OpenAI will likely take a small percentage of the transaction).
Launched in October at Dev Day [ https://substack.com/redirect/86bf2239-1a60-480b-84df-92a5d0cd9d8f?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], partners for ChatGPT’s apps already include large companies like Adobe, DoorDash, Canva, Figma, Booking.com, Coursera, Expedia, Spotify, and Zillow. Some of the biggest companies in the world are betting that chat will become a primary interface for their products.
ChatGPT apps represent a rare distribution opportunity, the kind that comes around once or twice a decade. The last comparable moments were the App Store in 2008, the rise of SEO in the early 2000s, and maybe Shopify’s app ecosystem. When a new distribution channel opens up at scale, the companies that move early capture habits that are hard to break later. This creates opportunity at both ends of the spectrum. For enterprises, ChatGPT apps are a new distribution channel alongside your existing ones. For solopreneurs, this is a chance to build microapps and get distribution without a marketing budget. The barrier to entry is low (a few weeks to build a simple app), but the reach is enormous.
In this post, I’ll break down how users find and use your apps, how these apps work behind the scenes, and how to create your own first ChatGPT app. Let’s build.
How users find and use ChatGPT apps
ChatGPT apps introduce interaction patterns that differ from traditional app stores. In most app stores, you have to find the app, install it, and only then you can use it. ChatGPT does support this pattern, but the more interesting pattern is contextual surfacing. In the near future (and something most people don’t fully grasp), ChatGPT will automatically suggest apps based on a user’s conversation. Ask about travel plans, and Expedia appears. Mention that you need a design, and Canva surfaces. Ask about ordering groceries, and an Instacart cart shows up. A user doesn’t need to know what apps are available; the model matches their intent to relevant tools. This has the potential to be a new and massive growth channel for products.
ChatGPT apps can appear in three formats, and as an app builder it’s important for you to consider which format would match the type of app experience you want to create for the user. I’ll say more about this in a bit, but each type leverages the Model Context Protocol (MCP) to deliver your app to ChatGPT.
Inline mode embeds cards and lists directly in the conversation flow. This is the default, and it works well for product listings, search results, or any content that fits naturally alongside ChatGPT’s responses. Here’s a quick example of hotel listings from Expedia:
Fullscreen mode takes over the entire screen. This is best for maps, dashboards, or complex workflows that need more space. When a user is browsing AllTrails on a map or editing a design in Canva, full screen gives them room to work.
Picture-in-picture mode keeps a small floating window visible while the user chats. This is ideal for music players, timers, or anything a user might want to keep running in the background while they work on something else. Here, Coursera is playing a video while I continue chatting.
There’s one important constraint to understand: one widget per message. If the user says, “Book a restaurant and order an Uber,” ChatGPT can show only one app at a time. This means users work sequentially through multi-step tasks rather than in parallel.
How it works behind the scenes
When you’re preparing to build a ChatGPT app, it’s important to first understand the architecture.
Every ChatGPT app has three parts:
The conversation within ChatGPT: The model interprets the user’s request and decides whether an app would be helpful.
The app’s “tools”: A backend server and API tells ChatGPT what the app can do.
The user-facing widget: This appears in the user’s chat, built with web technologies (typically React) and runs in a secure sandbox inside ChatGPT.
Let’s dig into #2, the app’s tools, because that’s the core of how this works. A tool is just a function that ChatGPT can call. When you build an app, you define tools, like search_restaurants, book_ticket, or create_playlist. Each tool has a name and description that helps ChatGPT understand when to use it and what parameters it accepts. When a user says something relevant, ChatGPT reads these descriptions and decides which tool to call.
Here’s the flow: The user says, “Find me Italian restaurants in Brooklyn.” ChatGPT looks at the available tools, sees one called search_restaurants with a description like “Search for restaurants by location and cuisine” and calls it with {location: “Brooklyn”, cuisine: “Italian”}. Your server runs the search, returns the results, and can optionally include a widget to display them. ChatGPT renders the widget in the chat with the user.
The user interacts with the widget—say, by clicking on a restaurant to reserve it. That click can trigger a follow-up tool call. Your widget then sends a message back to ChatGPT saying, “User selected restaurant_id: 1241,” and ChatGPT can call another tool, like book_reservation(), to save their reservation. The conversation continues, with the widget and the AI working together.
This creates a loop: user says something to ChatGPT → ChatGPT calls a tool → widget renders → user interacts with widget → ChatGPT calls another tool. The key insight is that ChatGPT orchestrates the whole thing. It decides when to call tools, what parameters to pass, and how to respond to user actions. Your app just exposes capabilities and renders UI.
MCP is the infrastructure connecting all of this. MCP is very similar to APIs (I covered those here [ https://substack.com/redirect/a0526999-5046-4901-8272-d94db25e0bad?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]), but rebuilt for AI agents. It provides a universal way to connect apps to AI assistants. Anthropic created MCP in November 2024, and OpenAI adopted it across ChatGPT and their developer tools in March 2025. In November, both companies announced they’re collaborating on MCP Apps [ https://substack.com/redirect/bfcb04ba-6a52-40e7-8f2b-6b0416779923?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], a standardized way to add interactive UIs to the protocol.
If you’ve heard of AI agents, this might sound familiar. ChatGPT apps and AI agents share the same core pattern: an AI model that can call external tools to accomplish tasks. The difference is who’s running the show. When you build your own AI agent, you control everything—the model, the prompts, the orchestration logic, the error handling. You decide when tools get called and how results are processed.
As you may have been thinking as you read this, tools also represent a newform of SEO (or is it AEO?). Based on your tool’s name and description, ChatGPT can suggest your app to users to help solve their needs, like creating a slide deck or generating a financial model. Having accurate tool descriptions that uniquely identify your app will help ChatGPT users find and use your app in the correct contexts.
Building your first ChatGPT app
Now that you understand the basic structure, you can have an app built in 30 minutes or less by following this guide.
Option 1: Replit
The Replit agent is not an expert on ChatGPT apps, so the easiest way to get started in Replit is to import an existing app. I’d recommend the official examples from OpenAI. To save some time, I created a Replit project you can duplicate with all of the following steps completed, here [ https://substack.com/redirect/53a8c30f-198f-4ce4-afa0-811adf15d1b7?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]. I’d highly recommend using my project; it will likely save you at least 30 minutes.
If you’d prefer to start from scratch, head to Replit, select “Import from GitHub,” and paste in this URL: https://github.com/openai/openai-apps-sdk-examples [ https://substack.com/redirect/d2f2f6e7-aa87-4e67-98de-007824a74cff?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
The Replit agent will then do some work to set up your project—it should take 5 to 10 minutes.
Once you have the project running, you should prompt the following:
I want to connect ChatGPT to my MCP server. Please set this up:
Bundle the React UI widgets - The project uses Vite to build React components into standalone widget bundles. Run pnpm run build with BASE_URL set to the full Replit domain URL. Each widget (in src/*/index.tsx) gets bundled into HTML/JS/CSS files in the /assets folder. The absolute URLs are critical because ChatGPT loads widgets in a sandbox that needs to fetch assets from my Replit server.
Static asset server on port 5000 - Serve the /assets folder with CORS enabled. Map to external port 80.
MCP server on port 8000 - Bind to 0.0.0.0:8000 for external access. Forward as port 8000.
Allow all hosts - Both servers must accept connections from any origin.
Give me the MCP endpoint URL for ChatGPT Settings > Connectors.
You may see a screen that appears to be an error, like the screenshot below. Replit is not built to preview MCP tools, so you’ll only be able to see the UI components once you’re connected to ChatGPT. Allow Replit to continue working until it has set up the MCP server correctly.
Eventually the Replit agent should tell you it’s ready. Common issues include misconfiguring ports and not being able to serve static assets, so follow up on these as needed. When ready (or if you copied my project), you should be presented with a screen like this:
We’re now ready to connect to ChatGPT. Ask the agent, “What is the external MCP URL for this app?” This should provide a URL like https://b3c4d0a4-6bdc-4926-b55e-5f94c6246e1e-00-1uvko22a6cltw.spock.replit.dev:8000/mcp.
To connect to ChatGPT, you will first need to enable Developer Mode [ https://substack.com/redirect/444deb15-1595-4a29-be7a-e5fd5b7d594f?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]on your ChatGPT account. From there, you can navigate to Settings -> Apps & Connectors -> New App. Paste your URL in this modal with a name (e.g. Replit App).
Once connected, you should be able to invoke the app by name:
Option 2: Chippy
Most vibe-coding tools aren’t built to help you understand MCP and ChatGPT apps. They’re great at building web apps, but they can’t create an MCP server, preview your tools, or help you connect to ChatGPT.
That’s why I decided to build one myself—Chippy [ https://substack.com/redirect/5384db82-098d-4375-9a64-e8949fac2a86?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]. Chippy is an AI agent that specializes in prototyping ChatGPT apps. You can test your app with the built-in chat, connect to ChatGPT without worrying about deployment, and even generate a spec directly from your prototype. And you can spin up your first app completely free.
In this example, I’ll build an app that lets users search Maven Lightning Lessons [ https://substack.com/redirect/b8c0a471-8ffc-466d-9c15-383967dfdf15?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] (free 30-minute talks from experts on AI, product, and design).
The core features are:
Find me a relevant Lightning Lesson based on some topic
Display the recording of the lesson inline in my ChatGPT thread
Move the display to picture-in-picture mode to continue interacting with ChatGPT while the Maven video plays
To start, I’ll head to Chippy.build [ https://substack.com/redirect/5384db82-098d-4375-9a64-e8949fac2a86?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] and ask Chippy to help me plan this project. Chippy suggests a single tool called find_lightning_lesson that takes a topic as input. It will then show an inline card to start, with an option to change to picture-in-picture.
From here, we just need to tell Chippy to implement. We can then get a preview of our app and test how it will work inside a chat environment.
We now have a functional ChatGPT app ready to test. Before we continue, grab your app link with “Test” in the top right corner
To connect to ChatGPT, you will first need to enable Developer Mode [ https://substack.com/redirect/444deb15-1595-4a29-be7a-e5fd5b7d594f?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]on your ChatGPT account. From there, you can navigate to Settings -> Apps & Connectors -> New App.
Add a Name, MCP Server URL, and set Authentication to No auth. Once you click Create, you’ve successfully made your first ChatGPT app!
The most reliable way to test your app is to mention it by name or tag it in your own chat. Below you can see that ChatGPT automatically tags your app if you mention it by name.
Once you have a functional app, you can continue to iterate and begin to build a golden set of prompts to trigger your app. You may want to add authentication, fetch real data out of your product, or build apps that use multiple tools together.
ChatGPT apps don’t have to be as simple as showing a video or displaying a card. You can build full, complex applications directly into ChatGPT. Here’s a quick example of a dungeon explorer game I built with Chippy. You can see that ChatGPT has context on my current level, information about the game, and can give me tips on improving my score.
The growth opportunity in front of you right now...
Unsubscribe https://substack.com/redirect/2/eyJlIjoiaHR0cHM6Ly93d3cubGVubnlzbmV3c2xldHRlci5jb20vYWN0aW9uL2Rpc2FibGVfZW1haWw_dG9rZW49ZXlKMWMyVnlYMmxrSWpvME1qWTFNVFV3TkRBc0luQnZjM1JmYVdRaU9qRTRNekEzT1RFMU5Td2lhV0YwSWpveE56WTRPVEUzTlRBM0xDSmxlSEFpT2pFNE1EQTBOVE0xTURjc0ltbHpjeUk2SW5CMVlpMHhNRGcwTlNJc0luTjFZaUk2SW1ScGMyRmliR1ZmWlcxaGFXd2lmUS5XeFg1dkpnWFJBeXlKaVcyU1FKd05jc1VGdzRKekxUX05Fd3RZQ0hnYVVzIiwicCI6MTgzMDc5MTU1LCJzIjoxMDg0NSwiZiI6dHJ1ZSwidSI6NDI2NTE1MDQwLCJpYXQiOjE3Njg5MTc1MDcsImV4cCI6MjA4NDQ5MzUwNywiaXNzIjoicHViLTAiLCJzdWIiOiJsaW5rLXJlZGlyZWN0In0._IUyAMNvMFaTKicmlpX0K3N_pgDj_Hgb55iBtF336b4?
View Email
ChatGPT apps are about to be the next big distribution channel: Here’s how to build one
lenny@substack.com1/20/2026
SubstackView this post on the web at https://www.lennysnewsletter.com/p/the-non-technical-pms-guide-to-building-with-cursor
Zevi Arnovitz is a product manager at Meta with no technical background who has figured out how to build and ship real products using AI. His engineering team at Meta asks him to teach them how he does what he does. In this episode, Zevi breaks down his complete AI workflow that allows non-technical people to build sophisticated products with Cursor.
Listen on YouTube [ https://substack.com/redirect/57d1d94c-dbcf-40e9-9118-64b0498634d6?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], Spotify [ https://substack.com/redirect/53648fe4-2601-4842-9c9f-acd670c6cfde?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], and Apple Podcasts [ https://substack.com/redirect/92a3b65a-d297-48d3-853e-6ca28df42097?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
We discuss:
The complete AI workflow that lets non-technical people build real products in Cursor
How to use multiple AI models for different tasks (Claude for planning, Gemini for UI)
Using slash commands to automate prompts
Zevi’s “peer review” technique, which uses different AI models to review each other’s code
Why this might be the best time to be a junior in tech, despite the challenging job market
How Zevi used AI to prepare for his Meta PM interviews
Brought to you by:
10Web [ https://substack.com/redirect/dbd4d06e-3b5b-42e1-afb7-1afb0e336a8d?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]—Vibe coding platform as an API
DX [ https://substack.com/redirect/09bd6314-93a2-4458-9544-f0189c290189?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]—The developer intelligence platform designed by leading researchers
Framer [ https://substack.com/redirect/e8a40801-70cc-4b11-965f-92ce8ed4cd7c?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]—Build better websites faster
Where to find Zevi Arnovitz:
• X: https://x.com/ArnovitzZevi [ https://substack.com/redirect/7c95d115-a897-4121-a0df-be409bd61a9c?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• LinkedIn: https://www.linkedin.com/in/zev-arnovitz [ https://substack.com/redirect/a0835d75-60d8-45f6-9421-6ed22b5d0eba?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Website: https://zeviarnovitz.com [ https://substack.com/redirect/c84505b7-408a-43aa-bce3-1d5cb69f672e?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Referenced:
• Becoming a super IC: Lessons from 12 years as a PM individual contributor | Tal Raviv (Product Lead at Riverside): https://www.lennysnewsletter.com/p/the-super-ic-pm-tal-raviv [ https://substack.com/redirect/150c2033-1c1f-4cbe-a005-4f0721c7fafb?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Wix: https://www.wix.com [ https://substack.com/redirect/a9aa7251-a051-4b39-ab34-0ea829fd65fc?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Building AI Apps: From Idea to Viral in 30 Days: https://www.youtube.com/watch?v=j2w4y7pDi8w [ https://substack.com/redirect/a307ddeb-b0a5-47a6-8385-5f1b0659833f?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Riley Brown on YouTube: https://www.youtube.com/channel/UCMcoud_ZW7cfxeIugBflSBw [ https://substack.com/redirect/887f798e-7430-4b8f-b05f-e47d3a14069a?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Greg Isenberg on YouTube: https://www.youtube.com/@GregIsenberg [ https://substack.com/redirect/335a8efc-dd0f-4b68-8dc1-a0792990926c?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Bolt: https://bolt.new [ https://substack.com/redirect/5dea9216-f4c6-4079-8b23-24f8fd56564e?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Inside Bolt: From near-death to ~$40m ARR in 5 months—one of the fastest-growing products in history | Eric Simons (founder and CEO of StackBlitz): https://www.lennysnewsletter.com/p/inside-bolt-eric-simons [ https://substack.com/redirect/8aa426cf-788b-405b-91e3-9f3453437c66?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Lovable: https://lovable.dev [ https://substack.com/redirect/48f8403f-be3e-435a-9bcb-972ea6ce2f48?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Building Lovable: $10M ARR in 60 days with 15 people | Anton Osika (co-founder and CEO): https://www.lennysnewsletter.com/p/building-lovable-anton-osika [ https://substack.com/redirect/97659fd4-83f0-4b95-9d5b-23580c9b0b1f?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• StudyMate: https://studymate.live [ https://substack.com/redirect/edb80c08-d46e-490c-9ec6-4bf2c951ce87?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Dibur2text: https://dibur2text.app [ https://substack.com/redirect/6bf612da-842b-4012-898c-0e8c8bfa2d5e?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Claude: https://claude.ai [ https://substack.com/redirect/08f00958-3c4a-4b18-9c17-0f25c7c3bbbf?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Everyone should be using Claude Code more: https://www.lennysnewsletter.com/p/everyone-should-be-using-claude-code [ https://substack.com/redirect/10337f30-4217-4e31-9c42-4bb641b99c72?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Bun: https://bun.com [ https://substack.com/redirect/b14e34c9-2e2f-4204-8fd2-6e08b74e8d5e?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Zustand: https://zustand.docs.pmnd.rs/getting-started/introduction [ https://substack.com/redirect/3ceca50a-dbb6-40f1-85e9-7921e3a4a6fd?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Cursor: https://cursor.com [ https://substack.com/redirect/96cd5556-9174-4623-8fc6-98bf5354e3a7?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• The rise of Cursor: The $300M ARR AI tool that engineers can’t stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell [ https://substack.com/redirect/c7942644-0c26-4f8d-b3a0-89eefd4b280d?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Wispr Flow: https://wisprflow.ai [ https://substack.com/redirect/9e69d746-baa0-4f1b-89d0-62cd17b76611?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Linear: https://linear.app [ https://substack.com/redirect/5408b37d-47af-40ce-8c95-c79c473638ae?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Linear’s secret to building beloved B2B products | Nan Yu (Head of Product): https://www.lennysnewsletter.com/p/linears-secret-to-building-beloved-b2b-products-nan-yu [ https://substack.com/redirect/13039361-def5-41db-9195-c9ddd930e36a?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Cursor Composer: https://cursor.com/blog/composer [ https://substack.com/redirect/060c6d79-50fc-420b-a46c-66cf202e708a?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Replit: https://replit.com [ https://substack.com/redirect/47f5aef1-3ce6-4ff7-ae87-f8a9c51fa3c8?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Behind the product: Replit | Amjad Masad (co-founder and CEO): https://www.lennysnewsletter.com/p/behind-the-product-replit-amjad-masad [ https://substack.com/redirect/ad184e53-0a18-4d9d-927f-e7bfce01f233?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Base44: https://base44.com [ https://substack.com/redirect/df0ae1c4-7837-43ee-8b78-462613ae9cb2?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Solo founder, $80M exit, 6 months: The Base44 bootstrapped startup success story | Maor Shlomo: https://www.lennysnewsletter.com/p/the-base44-bootstrapped-startup-success-story-maor-shlomo [ https://substack.com/redirect/0dfbd4a8-2942-4d76-a5a1-8f1abaadda9a?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• v0: https://v0.app [ https://substack.com/redirect/9f8655a1-51ac-47a0-8885-e90c5c07274d?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Everyone’s an engineer now: Inside v0’s mission to create a hundred million builders | Guillermo Rauch (founder & CEO of Vercel, creators of v0 and Next.js): https://www.lennysnewsletter.com/p/everyones-an-engineer-now-guillermo-rauch [ https://substack.com/redirect/13cde3e2-b583-4dc5-88dc-61fade6de4c3?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Cursor Browser mode: https://cursor.com/docs/agent/browser [ https://substack.com/redirect/7a083e36-df32-481a-930d-8dc1e409b98f?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Google Antigravity: https://antigravity.google [ https://substack.com/redirect/73a79044-636b-4dfa-8cb6-8326c497faa0?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Grok: https://grok.com [ https://substack.com/redirect/e62f1e1c-947a-4676-b390-93bcba2fd32b?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Zapier: https://zapier.com [ https://substack.com/redirect/1a946bd8-2273-4bd7-abd2-d8d1866d871c?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Airtable: https://www.airtable.com [ https://substack.com/redirect/5e2408e0-b478-4c82-9abb-e8f597da2d1b?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Build Your Personal PM Productivity System & AI Copilot: https://maven.com/tal-raviv/product-manager-productivity-system [ https://substack.com/redirect/0a0b2a68-7fc5-4307-b5a5-36051c0bf1e9?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• The definitive guide to mastering analytical thinking interviews: https://www.lennysnewsletter.com/p/the-definitive-guide-to-mastering-f81 [ https://substack.com/redirect/db46bbd9-f377-4363-92dd-28e7ccad8f45?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• AI tools are overdelivering: results from our large-scale AI productivity survey: https://www.lennysnewsletter.com/p/ai-tools-are-overdelivering-results-c08 [ https://substack.com/redirect/30cd6379-ae55-4126-83f3-88f4d8c885fc?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Yaara Asaf on LinkedIn: https://www.linkedin.com/in/yaarasaf [ https://substack.com/redirect/5a3135b8-3124-4168-8cd5-5b6506d99b5f?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• The Pitt on Prime Video: https://www.amazon.com/The-Pitt-Season-1/dp/B0DNRR8QWD [ https://substack.com/redirect/553131d1-7d10-4d91-b0f1-4254a1553845?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Severance on AppleTV+: https://tv.apple.com/us/show/severance/umc.cmc.1srk2goyh2q2zdxcx605w8vtx [ https://substack.com/redirect/18969a3e-726e-426b-85a9-bf650c2552f8?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Loom: https://www.loom.com [ https://substack.com/redirect/4d8be306-d87d-461f-9b09-5bfe259b750d?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Cap: https://cap.so [ https://substack.com/redirect/198b0ee1-3b7a-42b3-95ac-0376ed7758c0?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Supercut: https://supercut.ai [ https://substack.com/redirect/34c4395e-11e2-467c-ae27-1238ab7e4eab?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Recommended books:
• The Fountainhead: https://www.amazon.com/Fountainhead-Ayn-Rand/dp/0451191153 [ https://substack.com/redirect/8138f628-d9ee-4316-b2c2-240ea4a731ff?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Shoe Dog: A Memoir by the Creator of Nike: https://www.amazon.com/Shoe-Dog-Memoir-Creator-Nike/dp/1501135910 [ https://substack.com/redirect/8179b567-213a-4730-911b-e79e565817ed?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Mindset: The New Psychology of Success: https://www.amazon.com/Mindset-Psychology-Carol-S-Dweck/dp/0345472322 [ https://substack.com/redirect/61ea67d0-d8b4-4084-a4bc-7c07a26c0011?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Production and marketing by https://penname.co/ [ https://substack.com/redirect/79978a18-c769-422c-8662-4019f81d885f?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com [ mailto:podcast@lennyrachitsky.com ].
Lenny may be an investor in the companies discussed.
My biggest takeaways from this conversation:...
Unsubscribe https://substack.com/redirect/2/eyJlIjoiaHR0cHM6Ly93d3cubGVubnlzbmV3c2xldHRlci5jb20vYWN0aW9uL2Rpc2FibGVfZW1haWw_dG9rZW49ZXlKMWMyVnlYMmxrSWpvME1qWTFNVFV3TkRBc0luQnZjM1JmYVdRaU9qRTROREUyTnpBeU5pd2lhV0YwSWpveE56WTROelF6T0RVMUxDSmxlSEFpT2pFNE1EQXlOems0TlRVc0ltbHpjeUk2SW5CMVlpMHhNRGcwTlNJc0luTjFZaUk2SW1ScGMyRmliR1ZmWlcxaGFXd2lmUS5zd1RISkNLNk9kNnUxVGxGc3oyZ0JmQWVkcHdxVFlKZjNwZmt5dkliX1BZIiwicCI6MTg0MTY3MDI2LCJzIjoxMDg0NSwiZiI6dHJ1ZSwidSI6NDI2NTE1MDQwLCJpYXQiOjE3Njg3NDM4NTUsImV4cCI6MjA4NDMxOTg1NSwiaXNzIjoicHViLTAiLCJzdWIiOiJsaW5rLXJlZGlyZWN0In0.QGPT_nEZXdKf27iG1uwr9E651oZD8644NGwXPtR9gKU?
View Email
The non-technical PM’s guide to building with Cursor | Zevi Arnovitz (Meta)
lenny@substack.com1/18/2026
SubstackView this post on the web at https://www.lennysnewsletter.com/p/silicon-valleys-missing-etiquette-playbook
Sam Lessin is a partner at Slow Ventures, a former VP of Product at Facebook, and a two-time founder who’s now teaching etiquette to Silicon Valley’s founders. In this unconventional episode, Sam explains why proper etiquette has become a vital skill for founders in 2026—especially as technology becomes more central to society and trust becomes harder to build. His etiquette book and courses have become surprisingly popular, teaching founders how to “show up in a room with a low heart rate” and quickly build trust.
Listen on YouTube [ https://substack.com/redirect/ca1c8308-3612-41bd-a644-5cb86cffde10?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], Spotify [ https://substack.com/redirect/56788b34-60bd-458f-aaa5-60b4f4612dd1?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], and Apple Podcasts [ https://substack.com/redirect/a2660f69-ee0a-404c-9a59-bc95e28681f1?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
We discuss:
Why etiquette matters
Sam’s framework for showing up confidently, with a low heart rate, in any room
How to navigate introductions, small talk, meetings, and meals like a pro
Simple hacks for remembering names and handling awkward social situations
30+ specific etiquette tips
Brought to you by:
10Web [ https://substack.com/redirect/3418e7ad-a507-410c-9ef1-3b6452c29b79?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]—Vibe-coding platform as an API
DX [ https://substack.com/redirect/5fbff447-baf1-4624-8590-c4633379924c?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]—The developer intelligence platform designed by leading researchers
WorkOS [ https://substack.com/redirect/49b4956c-2489-4808-b044-df87f29a31de?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]—Modern identity platform for B2B SaaS, free up to 1 million MAUs
Where to find Sam Lessin:
• X: https://x.com/lessin [ https://substack.com/redirect/a6bf153a-c86b-4803-8eee-95db84cb56d1?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• LinkedIn: https://www.linkedin.com/in/wlessin [ https://substack.com/redirect/ec1d0e1d-abec-4bec-a8fa-f70fc1461292?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Website: https://www.wlessin.com [ https://substack.com/redirect/d5db2e3d-ee3a-44a7-8655-dac84548bcbd?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Podcast: https://moreorlesspod.com [ https://substack.com/redirect/bea27286-e6fa-44fd-8dcc-6bbe1f329ed3?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Lettermeme: https://lettermeme.com/lessin [ https://substack.com/redirect/bad0c21f-ba8e-4108-865e-2f912a41b1f1?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Referenced:
• Y Combinator: https://www.ycombinator.com [ https://substack.com/redirect/5b65d1ed-d958-471a-a98d-8c38f71afa34?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Kleiner Perkins: https://www.kleinerperkins.com [ https://substack.com/redirect/eb3c1e76-ea0a-4572-8143-12a468dcf948?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• “Lose Yourself” by Eminem on Spotify: https://open.spotify.com/track/7MJQ9Nfxzh8LPZ9e9u68Fq [ https://substack.com/redirect/af62276a-0f01-4ac3-8c6f-a0cb8ea57cab?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Alison Gopnik on Childhood Learning, AI as a Cultural Technology, and Rethinking Nature vs. Nurture: https://conversationswithtyler.com/episodes/alison-gopnik [ https://substack.com/redirect/1dc49d4e-e1c2-40b4-b427-20ab2352bd07?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Garry Tan on LinkedIn: https://www.linkedin.com/in/garrytan [ https://substack.com/redirect/3e8b91f0-ab57-43a1-a725-05ccb9eb8561?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Bain & Company: https://www.bain.com [ https://substack.com/redirect/9188a2e3-2700-4d7c-a92b-443c13fc4ed6?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Evernote: https://evernote.com [ https://substack.com/redirect/6436e04e-6fc9-4840-895d-f0d43cc4a3b7?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Calendly: https://calendly.com [ https://substack.com/redirect/a4b6cca0-7107-48bd-964b-39dd5a07c1a5?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Morning Brew: https://www.morningbrew.com [ https://substack.com/redirect/99c2975d-cd79-48bf-b921-05b6f97885c8?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Cursor: https://cursor.com [ https://substack.com/redirect/8ee62ba9-aa08-4793-bce3-fed3f247debc?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• The rise of Cursor: The $300M ARR AI tool that engineers can’t stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell [ https://substack.com/redirect/19171e25-8ab6-4fd1-9ded-7df8a8ffd31c?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• DigitalOcean: https://www.digitalocean.com [ https://substack.com/redirect/57e59a2a-31e2-4d94-a408-a3736ff273ab?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Cloudflare: https://www.cloudflare.com [ https://substack.com/redirect/eb21a8b5-ecc9-48d7-8373-4c9aa134ee14?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• SpaceX: https://www.spacex.com [ https://substack.com/redirect/27b6c6c4-1707-4983-9f96-5fdcfe2a6dea?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Marc Andreessen on X: https://x.com/pmarca [ https://substack.com/redirect/09d70585-592d-45d9-b8bf-dc37a0e46799?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Landman on Prime Video: https://www.amazon.com/Landman-Season-1/dp/B0D4D8RTMD [ https://substack.com/redirect/8024477d-5622-44c2-84e2-84d9de0cbb02?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Dave Morin on X: https://x.com/davemorin [ https://substack.com/redirect/fd668cce-6a88-4d91-868b-241734824697?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Recommended books:
• Modern Etiquette in Technology, Finance, Society, and at Home: A Slow Ventures Handbook: https://www.amazon.com/Modern-Etiquette-Technology-Finance-Society-ebook/dp/B0G4HSKSY5 [ https://substack.com/redirect/f33079b7-8c02-42cd-b333-d4a231397b97?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Life, the Universe and Everything: https://www.amazon.com/Universe-Everything-Hitchhikers-Guide-Galaxy-ebook/dp/B001ODEQ7A [ https://substack.com/redirect/7ea09081-4e6b-490c-a311-220e44d7257b?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• The Ancient City: A Study on the Religion, Laws, and Institutions of Greece and Rome: https://www.amazon.com/Ancient-City-Religion-Institutions-Greece/dp/0801823048 [ https://substack.com/redirect/061433c0-3332-497b-8e7e-5b70948e07f4?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Man’s Search for Meaning: https://www.amazon.com/Mans-Search-Meaning-Viktor-Frankl-ebook/dp/B009U9S6FI [ https://substack.com/redirect/24be0826-a19f-4795-a9b0-f1a459559979?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Area 51: An Uncensored History of America’s Top Secret Military Base: https://www.amazon.com/Area-51-Uncensored-Americas-Military-ebook/dp/B004THU68Q [ https://substack.com/redirect/4a8baa6a-0c34-4677-b8d3-5011a4f38353?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• The Lessons of History: https://www.amazon.com/Lessons-History-Will-Durant/dp/143914995X [ https://substack.com/redirect/2638e24b-8ffa-412e-b605-597d9b8d4a94?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• The Fish That Ate the Whale: The Life and Times of America’s Banana King: https://www.amazon.com/Fish-That-Ate-Whale-Americas/dp/1250033314 [ https://substack.com/redirect/140de59b-ffe0-4200-b978-c7c0ced514b1?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• The Last Kings of Shanghai: The Rival Jewish Dynasties That Helped Create Modern China: https://www.amazon.com/Last-Kings-Shanghai-Jewish-Dynasties/dp/0735224439 [ https://substack.com/redirect/538e384c-c125-450a-8d6a-0ebf2ef501e6?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Production and marketing by https://penname.co/ [ https://substack.com/redirect/1c3f8001-cc17-493f-bafc-4e4db7c08198?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com [ mailto:podcast@lennyrachitsky.com ].
Lenny may be an investor in the companies discussed.
My biggest takeaways from this conversation:...
Unsubscribe https://substack.com/redirect/2/eyJlIjoiaHR0cHM6Ly93d3cubGVubnlzbmV3c2xldHRlci5jb20vYWN0aW9uL2Rpc2FibGVfZW1haWw_dG9rZW49ZXlKMWMyVnlYMmxrSWpvME1qWTFNVFV3TkRBc0luQnZjM1JmYVdRaU9qRTRNekF3TlRJNE5pd2lhV0YwSWpveE56WTRORGcwTnpJd0xDSmxlSEFpT2pFNE1EQXdNakEzTWpBc0ltbHpjeUk2SW5CMVlpMHhNRGcwTlNJc0luTjFZaUk2SW1ScGMyRmliR1ZmWlcxaGFXd2lmUS5sQ0d1UktSRl9Gc2FQQU53WWdCZzZvVnlhZm1va3FqNW9LRkotVnRDRy0wIiwicCI6MTgzMDA1Mjg2LCJzIjoxMDg0NSwiZiI6dHJ1ZSwidSI6NDI2NTE1MDQwLCJpYXQiOjE3Njg0ODQ3MjAsImV4cCI6MjA4NDA2MDcyMCwiaXNzIjoicHViLTAiLCJzdWIiOiJsaW5rLXJlZGlyZWN0In0.BUhvp8K4kWdCQyjLWzwUpTr4hiDsBpPKZVCIi_0hPbc?
View Email
How to show up in any room with a low heart rate: Silicon Valley’s missing etiquette playbook | Sam Lessin
lenny@substack.com1/15/2026
SubstackView this post on the web at https://www.lennysnewsletter.com/p/what-openai-and-google-engineers-learned
Aishwarya Naresh Reganti and Kiriti Badam have helped build and launch more than 50 enterprise AI products across companies like OpenAI, Google, Amazon, and Databricks. Based on these experiences, they’ve developed a small set of best practices for building and scaling successful AI products. The goal of this conversation is to save you and your team a lot of pain and suffering.
Listen on YouTube [ https://substack.com/redirect/239ca09e-c954-474e-b379-73d84c37226c?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], Spotify [ https://substack.com/redirect/68188547-7504-4e9b-8e19-2ccfabd5dd0c?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], and Apple Podcasts [ https://substack.com/redirect/76bf8a29-cd8a-47f5-914c-42cc25b402bb?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
We discuss:
Two key ways AI products differ from traditional software, and why that fundamentally changes how they should be built
Common patterns and anti-patterns in companies that build strong AI products versus those that struggle
A framework they developed from real-world experience to iteratively build AI products that create a flywheel of improvement
Why obsessing about customer trust and reliability is an underrated driver of successful AI products
Why evals aren’t a cure-all, and the most common misconceptions people have about them
The skills that matter most for builders in the AI era
Brought to you by:
Merge [ https://substack.com/redirect/01d27ed9-5483-4312-9179-81887fabe29c?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]—The fastest way to ship 220+ integrations
Strella [ https://substack.com/redirect/bcd6d313-94fa-4739-a3ed-8f92b4b33a21?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]—The AI-powered customer research platform
Brex [ https://substack.com/redirect/4fec3922-0353-4617-b3c8-647089588b86?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]—The banking solution for startups
Get 15% off Aishwarya and Kiriti’s Maven course, Building Agentic AI Applications with a Problem-First Approach, using this link: https://bit.ly/3V5XJFp [ https://substack.com/redirect/9bde9ec4-a276-4650-bc0b-2f92a61f13d0?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Where to find Aishwarya Naresh Reganti:
• LinkedIn: https://www.linkedin.com/in/areganti [ https://substack.com/redirect/f3045d2d-48cb-4a28-a271-6882a30cb046?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• GitHub: https://github.com/aishwaryanr/awesome-generative-ai-guide [ https://substack.com/redirect/39e149ea-8155-4492-8d7d-989159125baa?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• X: https://x.com/aish_reganti [ https://substack.com/redirect/2fd9375c-5050-4938-ad81-16343177d8de?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Where to find Kiriti Badam:
• LinkedIn: https://www.linkedin.com/in/sai-kiriti-badam [ https://substack.com/redirect/f27b6f3f-77ab-4e9c-a6cd-3e5ee394a837?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• X: https://x.com/kiritibadam [ https://substack.com/redirect/b2d1f3e5-0ebb-4f41-ba10-1a5a03ff37e7?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Referenced:
• LevelUp Labs: https://levelup-labs.ai/ [ https://substack.com/redirect/2308dc08-cedb-4323-8a68-cd0948397f8f?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Why your AI product needs a different development lifecycle: https://www.lennysnewsletter.com/p/why-your-ai-product-needs-a-different [ https://substack.com/redirect/2fa043b5-9622-41ea-bc7a-653f5e36de29?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Booking.com: https://www.booking.com [ https://substack.com/redirect/e689c9a5-d7dd-407e-b0b3-a1a633ccf9d5?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Research paper on agents in production (by Matei Zaharia’s lab): https://arxiv.org/pdf/2512.04123 [ https://substack.com/redirect/816a944f-a65c-410f-bf22-932ac28c40e5?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Matei Zaharia’s research on Google Scholar: https://scholar.google.com/citations?user=I1EvjZsAAAAJ&hl=en [ https://substack.com/redirect/c2dbb978-a43a-49d4-962d-f6eec340eb8e?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• The coming AI security crisis (and what to do about it) | Sander Schulhoff: https://www.lennysnewsletter.com/p/the-coming-ai-security-crisis [ https://substack.com/redirect/372bb75f-a020-4197-bece-d64a09b14814?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Gajen Kandiah on LinkedIn: https://www.linkedin.com/in/gajenkandiah [ https://substack.com/redirect/83d89e4a-63fd-4886-8145-becf956e6348?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Rackspace: https://www.rackspace.com [ https://substack.com/redirect/63e0cd0e-8317-4a54-9b44-7923e83b870b?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• The AI-native startup: 5 products, 7-figure revenue, 100% AI-written code | Dan Shipper (co-founder/CEO of Every): https://www.lennysnewsletter.com/p/inside-every-dan-shipper [ https://substack.com/redirect/1caa2efe-cf90-4bf1-a6d3-bad3aea70ac9?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Semantic Diffusion: https://martinfowler.com/bliki/SemanticDiffusion.html [ https://substack.com/redirect/482059ac-10c6-4411-aad0-c45a1ec4e2de?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• LMArena: https://lmarena.ai [ https://substack.com/redirect/b18ad938-4996-4ac1-8b5d-e58f19873b16?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Artificial Analysis: https://artificialanalysis.ai/leaderboards/providers [ https://substack.com/redirect/8dbacbff-682c-404a-baa8-3a68c76ca81f?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Why humans are AI’s biggest bottleneck (and what’s coming in 2026) | Alexander Embiricos (OpenAI Codex Product Lead): https://www.lennysnewsletter.com/p/why-humans-are-ais-biggest-bottleneck [ https://substack.com/redirect/b6343601-6ae8-4362-a229-847a02cac08b?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Airline held liable for its chatbot giving passenger bad advice—what this means for travellers: https://www.bbc.com/travel/article/20240222-air-canada-chatbot-misinformation-what-travellers-should-know [ https://substack.com/redirect/3f132d4c-32c8-4dfd-b461-044e482d29e0?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Demis Hassabis on LinkedIn: https://www.linkedin.com/in/demishassabis [ https://substack.com/redirect/d7af86c3-8005-4a43-a6df-1f3a1bcbe68d?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• We replaced our sales team with 20 AI agents—here’s what happened | Jason Lemkin (SaaStr): https://www.lennysnewsletter.com/p/we-replaced-our-sales-team-with-20-ai-agents [ https://substack.com/redirect/151b177b-51e9-4401-a9d1-0c453e4cec51?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Socrates’s quote: https://en.wikipedia.org/wiki/The_unexamined_life_is_not_worth_living [ https://substack.com/redirect/ad771ccb-a52c-4a5d-b870-38be5401ed3c?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Noah Smith’s newsletter: https://www.noahpinion.blog [ https://substack.com/redirect/d19b381a-00b8-4224-9f5a-fc44be1e4626?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Silicon Valley on HBO Max: https://www.hbomax.com/shows/silicon-valley/b4583939-e39f-4b5c-822d-5b6cc186172d [ https://substack.com/redirect/2957aaaf-554f-4592-b8ca-8f6a8b72ed89?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Clair Obscur: Expedition 33: https://store.steampowered.com/app/1903340/Clair_Obscur_Expedition_33/ [ https://substack.com/redirect/2e070cc3-0ec7-4837-aa73-f32ac3b5912e?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Wisprflow: https://wisprflow.ai [ https://substack.com/redirect/0d7716e5-f2ac-42d2-b8ea-2eb59b05be68?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Raycast: https://www.raycast.com [ https://substack.com/redirect/149ea48e-13d2-415f-aed4-647e2b1ffe84?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Steve Jobs’s quote: https://www.goodreads.com/quotes/463176-you-can-t-connect-the-dots-looking-forward-you-can-only [ https://substack.com/redirect/ba4d39ae-281a-47d0-b1a0-ba624f69414e?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Recommended books:
• When Breath Becomes Air: https://www.amazon.com/When-Breath-Becomes-Paul-Kalanithi/dp/081298840X [ https://substack.com/redirect/cc8cf373-88db-4926-9077-5e76691bd760?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• The Three-Body Problem: https://www.amazon.com/Three-Body-Problem-Cixin-Liu/dp/0765382032 [ https://substack.com/redirect/eaed5dc3-67f1-4987-8b95-47f677184834?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• A Fire Upon the Deep: https://www.amazon.com/Fire-Upon-Deep-Zones-Thought/dp/0812515285 [ https://substack.com/redirect/59f5a09a-f795-429b-9c77-b553dc59ef5b?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Production and marketing by https://penname.co/ [ https://substack.com/redirect/cc1b16b4-e374-461b-9620-83533e0dd8d4?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com [ mailto:podcast@lennyrachitsky.com ].
Lenny may be an investor in the companies discussed.
My biggest takeaways from this conversation:...
Unsubscribe https://substack.com/redirect/2/eyJlIjoiaHR0cHM6Ly93d3cubGVubnlzbmV3c2xldHRlci5jb20vYWN0aW9uL2Rpc2FibGVfZW1haWw_dG9rZW49ZXlKMWMyVnlYMmxrSWpvME1qWTFNVFV3TkRBc0luQnZjM1JmYVdRaU9qRTRNekF3TnpneU1pd2lhV0YwSWpveE56WTRNVE01TURnMUxDSmxlSEFpT2pFM09UazJOelV3T0RVc0ltbHpjeUk2SW5CMVlpMHhNRGcwTlNJc0luTjFZaUk2SW1ScGMyRmliR1ZmWlcxaGFXd2lmUS5QOUdyUVFTcU4xSGIwVTBmbGFmYld0bG40OE9NTXRSalJsM3YzcnMwMkRBIiwicCI6MTgzMDA3ODIyLCJzIjoxMDg0NSwiZiI6dHJ1ZSwidSI6NDI2NTE1MDQwLCJpYXQiOjE3NjgxMzkwODUsImV4cCI6MjA4MzcxNTA4NSwiaXNzIjoicHViLTAiLCJzdWIiOiJsaW5rLXJlZGlyZWN0In0.j_R3scFyGVlGtdQIhXrDliTZABDZCjU8yLIe0ay8VYg?
View Email
What OpenAI and Google engineers learned deploying 50+ AI products in production
lenny@substack.com1/11/2026
SubstackView this post on the web at https://www.lennysnewsletter.com/p/best-of-lennys-newsletter-2026
👋 Hey there, I’m Lenny. Each week, I answer reader questions about building product, driving growth, and accelerating your career. For more: Lenny’s Podcast [ https://substack.com/redirect/688a76bc-bb77-4ec7-ad8f-364f06474032?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] | How I AI [ https://substack.com/redirect/3a4ccf0b-d6b0-42eb-ab17-082d2d21b3c6?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] | Lennybot [ https://substack.com/redirect/fdbdf0ae-9364-439c-b145-05ca73df7391?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] | Lenny’s Reads [ https://substack.com/redirect/cd6d7b43-cd1d-4d0b-888f-de9542efaaa9?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] | Favorite AI and PM courses [ https://substack.com/redirect/3d881be4-f4ee-4ba8-b00c-0890bb7e6b93?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] | Favorite public speaking course [ https://substack.com/redirect/b7132497-4bcf-476f-b788-7be108884266?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ].
P.S. Insider subscribers [ https://substack.com/redirect/8a4af180-6c50-4906-b488-1cf82d2c3b43?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] get a free year of 19 premium products: Lovable, Replit, Gamma, n8n, Bolt, Devin, Wispr Flow, Descript, Linear, PostHog, Superhuman, Granola, Warp, Perplexity, Raycast, Magic Patterns, Mobbin, ChatPRD, and Stripe Atlas [ https://substack.com/redirect/46fb20c5-734f-47e9-a52e-f464a31038d2?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] (terms apply [ https://substack.com/redirect/bed2977c-67f2-4a71-925c-4c9949c213bf?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]). Subscribe now [ https://substack.com/redirect/ffb5982d-91b8-48b1-9b8f-2e89f0ed6539?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ].
Anthropic co-founder Ben Mann’s words [ https://substack.com/redirect/7cd1b849-acf8-4ca5-bfff-7ff884a44c56?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] continue to ring in my ears: “This is as normal as it’s going to be. It’s going to be much weirder very soon.”
In the swirl of so much change, there’s a growing divide between the people who understand where things are going and will benefit from it, and those who don’t and will have an increasingly hard time. More and more, I see my mission as making sure you’re in the first group.
Through deeply researched essays [ https://substack.com/redirect/a5794a22-4f49-4457-bb63-0be041c8844f?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], in-depth interviews with world-class operators working at the bleeding edge [ https://substack.com/redirect/688a76bc-bb77-4ec7-ad8f-364f06474032?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], a thriving online and offline community [ https://substack.com/redirect/b9aa8fc1-8296-4be4-9fd8-d54b5dc17102?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], free access to the latest and greatest AI tools [ https://substack.com/redirect/28e50f4c-323d-44f6-a227-ed4068d76b19?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], and the surprisingly helpful Lennybot [ https://substack.com/redirect/fdbdf0ae-9364-439c-b145-05ca73df7391?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] (trained on all of the newsletter and podcast content, it’s very good!), your subscription gives you a giant leg-up on the fast-approaching weird future.
To help you get ready for the surely-to-be-absurd year ahead, below are the 25 best and most popular posts from the past year, plus a few all-time classics. I know I put out a lot of content, so if you’ve still got 50 tabs open with posts you’ve been planning to read, close them all and check out the stuff below.
As always, I’d love your frank and honest feedback on what you love and what I could do better in the coming year. You can always find me at lenny@lennyrachitsky.com.
Finally, to keep myself accountable, here’s a quick look back at my goals for 2025 [ https://substack.com/redirect/b2118a9a-aa4f-4629-9acc-34be028538c0?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]:
Launching a new newsletter or podcast vertical ✅ — How I AI [ https://substack.com/redirect/3a4ccf0b-d6b0-42eb-ab17-082d2d21b3c6?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] has been a huge hit (go Claire [ https://substack.com/redirect/5bbeea66-90fe-4a44-ac22-8a4a10e5956f?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]!), and I’m in the process of exploring the next addition.
Lenny and Friends Summit 2.0 🟡 — Stay tuned for some news on this 👀
Making the paid subscription an absolute no-brainer by adding more killer perks ✅ — The Product Pass [ https://substack.com/redirect/28e50f4c-323d-44f6-a227-ed4068d76b19?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] has been a wild success, and wait till you see what we’ve got coming this year.
Launching a product ❌ — I decided it wasn’t the right year for this.
Above all else, continuing to deliver a high-quality newsletter and podcast every week ✅ — I think we achieved this, though I can always do better.
Now here are my goals for 2026:
Keep increasing the quality and value of the newsletter (possibly cutting back the quantity a bit)
Invest more into supporting the community around the newsletter and podcast
Launch an additional newsletter or podcast vertical
Lenny and Friends Summit 2.0 👀👀👀
Carefully balance content cadence between AI and non-AI, IC vs. manager vs. VPs, and product management vs. adjacent skills
Here we go.
📣 Quick heads-up: We’re refreshing our Product Pass [ https://substack.com/redirect/28e50f4c-323d-44f6-a227-ed4068d76b19?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] partner lineup at the end of January
We’ve got some very exciting new products coming to the Product Pass [ https://substack.com/redirect/28e50f4c-323d-44f6-a227-ed4068d76b19?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] in a few weeks, and to make room, a few current partners are rolling off the bundle: codes for Descript, Raycast, and Superhuman will expire on January 29th.
If you’ve been meaning to try any of these amazing products, this is your chance.
Head to LennysProductPass.com [ https://substack.com/redirect/9f38c5e4-1523-4831-be3a-0d5a95e7b76c?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] to grab your codes, and activate them by following the redemption instructions by January 29th. (Note: Descript is Insider-only, so if you’re at the Annual tier it’ll only be there if you grabbed it already.)
While you’re there, check out the other products too. Supplies are limited and deals do expire, so don’t miss out on the tools that you want to try out.
And now, the top posts from the last year . . .
Best on AI
An AI glossary [ https://substack.com/redirect/90f74b15-6416-49fd-82d5-54b9b0519747?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]—The most common AI terms explained, simply
Everyone should be using Claude Code more [ https://substack.com/redirect/2d8446b2-12fc-4cc2-90ca-c573cbc6d613?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]—How to get started with Claude Code, and 50 ways non-technical people are using it in their work and life
What people are vibe coding [ https://substack.com/redirect/eaeb37d5-00ca-4da8-986c-a61945124f75?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]—Real-life examples of what non-technical people are building to inspire your own vibe-coding journey
25 proven tactics to accelerate AI adoption at your company [ https://substack.com/redirect/bc595c4b-eddb-426b-a204-4afb006e1e7c?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]—Practical advice from AI-forward companies like Shopify, Ramp, Zapier, Duolingo, Intercom, and Whoop
A guide to AI prototyping for product managers [ https://substack.com/redirect/9c2af8c7-20f6-4008-aa8e-46dc4b2c2335?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]—How to turn your idea into a working prototype in minutes
Make product management fun again with AI agents [ https://substack.com/redirect/11bc2ce2-031b-49e4-b38d-0ede0046e73e?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]—A guide to building AI agents
Best on career
Product manager is an unfair role. So work unfairly. [ https://substack.com/redirect/ef301406-be26-4e19-a140-2c3dbed2da57?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]—How to thrive in “the great flattening” by redefining work norms
State of the product job market in 2025 [ https://substack.com/redirect/784852d5-947f-49c8-89ae-2005051958ba?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]—There’s a lot to be optimistic about
The definitive guide to mastering the analytical [ https://substack.com/redirect/af44538d-3b51-4478-91ea-0ccb13e3ff04?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] and product sense interviews [ https://substack.com/redirect/3eec59b2-bbb5-4652-977f-1d3532b82fa4?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]—A step-by-step playbook to help you ace your PM interviews
The ultimate guide to negotiating your comp [ https://substack.com/redirect/b4ed638f-4c84-4afb-811f-4e640070478a?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]—The step-by-step guide that’s helped hundreds of leaders secure life-changing compensation
The Magic Loop [ https://substack.com/redirect/4273aa67-3cc8-4bf3-8d06-15f37231fcf9?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]—A framework for rapid career growth
Best on health
Why you’re so angry at work (and what to do about it) [ https://substack.com/redirect/c2163a31-f283-4a40-b520-7d3c10d6c6bf?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]—A practical framework for transforming big feelings into wisdom
Why no productivity hack will solve your overwhelm [ https://substack.com/redirect/196590d7-b9b2-44f5-b0bb-0949279e3cb7?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]—How the Internal Family Systems model can help you listen to your inner wisdom and get unstuck
How tech’s most resilient workers handle burnout [ https://substack.com/redirect/3e07c322-997a-4f34-be8e-4cf0c0973a6e?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]—Introducing ARMOR: a new framework building on our tech worker sentiment survey insights
A builder’s guide to living a long and healthy life, with Justin Mares [ https://substack.com/redirect/c3fa4291-5f33-4c99-ad25-d3130e105afc?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]—For something a little different
Best on strategy...
Unsubscribe https://substack.com/redirect/2/eyJlIjoiaHR0cHM6Ly93d3cubGVubnlzbmV3c2xldHRlci5jb20vYWN0aW9uL2Rpc2FibGVfZW1haWw_dG9rZW49ZXlKMWMyVnlYMmxrSWpvME1qWTFNVFV3TkRBc0luQnZjM1JmYVdRaU9qRTRNekUzT1RNd09Dd2lhV0YwSWpveE56WTNOekEzT1RFMUxDSmxlSEFpT2pFM09Ua3lORE01TVRVc0ltbHpjeUk2SW5CMVlpMHhNRGcwTlNJc0luTjFZaUk2SW1ScGMyRmliR1ZmWlcxaGFXd2lmUS5PSy1JTnRiekc5aGhzTjQwMXZyODR6YWpBZi1qTlRWTEc0Q1hGVW9fVFFjIiwicCI6MTgzMTc5MzA4LCJzIjoxMDg0NSwiZiI6dHJ1ZSwidSI6NDI2NTE1MDQwLCJpYXQiOjE3Njc3MDc5MTUsImV4cCI6MjA4MzI4MzkxNSwiaXNzIjoicHViLTAiLCJzdWIiOiJsaW5rLXJlZGlyZWN0In0.KfU5HTa7QSOZYFQecV22QkgIut4_wxrtUzS6eI4_kOc?
View Email
Best of Lenny’s Newsletter 2026
lenny@substack.com1/6/2026
SubstackView this post on the web at https://www.lennysnewsletter.com/p/the-high-growth-handbook-molly-graham
Molly Graham has worked for some of tech’s most effective leaders, including Mark Zuckerberg, Sheryl Sandberg, Chamath Palihapitiya, and Bret Taylor. Today she leads Glue Club, a community for leaders navigating rapid scale, growth, and change. She’s best known for her “Give away your Legos” framework and her collection of practical mental models for leading through hypergrowth.
Listen on YouTube [ https://substack.com/redirect/9a9f5775-9268-4291-b3ae-a1aa5beae5be?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], Spotify [ https://substack.com/redirect/40416cfa-9c5d-4d97-aca3-4bbec2955897?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], and Apple Podcasts [ https://substack.com/redirect/43f506b2-c10b-49fe-9bfd-c6c16a4fa9cd?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
We discuss:
“Give away your Legos”: a framework for scaling yourself as a leader
“J-curves vs. stairs”: the two paths of career growth, and why you should pick the scarier path
“The waterline model” for diagnosing team problems (and why you should “snorkel before you scuba”)
Six rules for creating effective goals (and aligning everyone around them)
Rules of thumb for leading through rapid scale and change
Her biggest leadership lessons from Mark Zuckerberg, Sergey Brin, Larry Page, Sheryl Sandberg, and Bret Taylor
Brought to you by:
DX [ https://substack.com/redirect/60f09542-7dda-4783-bf2e-0915cb38af73?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]—The developer intelligence platform designed by leading researchers
Brex [ https://substack.com/redirect/20e0c48a-856b-41ab-bb8e-51d14636de29?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]—The banking solution for startups
GoFundMe Giving Funds [ https://substack.com/redirect/72c0052a-ae60-497a-b144-b2efc743b2bb?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]—Make helping a habit
Where to find Molly Graham:
• X: https://x.com/molly_g [ https://substack.com/redirect/2922e583-0220-4208-9d09-aed009cc1066?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• LinkedIn: https://www.linkedin.com/in/mograham [ https://substack.com/redirect/fb79e651-159c-48bd-92b1-9ee8a86cba6b?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Substack: https://mollyg.substack.com [ https://substack.com/redirect/35ad5b62-953a-4c18-8555-e7dfbf26b2fa?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Website: https://glueclub.com [ https://substack.com/redirect/83fa5c20-37bd-4501-b012-116f0a2ee2d3?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Referenced:
• Making an impact through authenticity and curiosity | Ami Vora (CPO at Faire, ex-WhatsApp, FB, IG): https://www.lennysnewsletter.com/p/authenticity-and-curiosity-ami-vora [ https://substack.com/redirect/7d3d9c07-463f-4bfc-a0a4-d8cb7bdb6e91?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Sheryl Sandberg on LinkedIn: https://www.linkedin.com/in/sheryl-sandberg-5126652 [ https://substack.com/redirect/0859225b-899b-46b2-aa0f-d00e08822bb7?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Elliot Schrage on LinkedIn: https://www.linkedin.com/in/elliotschrage [ https://substack.com/redirect/ed9cd560-bde2-434d-9a3d-0a4076dbefe6?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Quip: https://quip.com [ https://substack.com/redirect/1a2edeaa-a6df-4901-89ae-946cabd3d8ab?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• He saved OpenAI, invented the “Like” button, and built Google Maps: Bret Taylor on the future of careers, coding, agents, and more: https://www.lennysnewsletter.com/p/he-saved-openai-bret-taylor [ https://substack.com/redirect/893d2176-0cc7-4039-9ed7-4fb0b7adb3b6?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Chan Zuckerberg Initiative: https://chanzuckerberg.com [ https://substack.com/redirect/ec06f8c2-0631-4bd1-9ece-def5cb4d003d?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling): https://www.lennysnewsletter.com/p/10-contrarian-leadership-truths [ https://substack.com/redirect/a712736a-c014-436f-a7f0-f82f06c89fa9?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• ‘Give Away Your Legos’ and Other Commandments for Scaling Startups: https://review.firstround.com/give-away-your-legos-and-other-commandments-for-scaling-startups [ https://substack.com/redirect/4d0114ba-3f1e-4b73-9a95-f138d2acbe1d?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• The Muppets: https://muppets.disney.com [ https://substack.com/redirect/ac478f62-b9ea-4a5e-b456-2ef01666067c?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Sara Caldwell on LinkedIn: https://www.linkedin.com/in/saramcaldwell [ https://substack.com/redirect/10b82f56-8d4d-462c-a765-b05b4fda6a2d?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• J-Curves vs. Stairs: Two Approaches to Career Growth: https://mollyg.substack.com/p/j-curve [ https://substack.com/redirect/1d9d3a03-5ce6-40f7-83df-f97600b059d5?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Forget the corporate ladder—winners take risks: https://www.ted.com/talks/molly_graham_forget_the_corporate_ladder_winners_take_risks [ https://substack.com/redirect/3430439f-e9c7-42fb-9762-9e54d8e44c7d?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Chamath Palihapitiya on LinkedIn: https://www.linkedin.com/in/chamath [ https://substack.com/redirect/eb23d73e-30d6-467b-a6d3-1d381f364788?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Lori Goler on LinkedIn: https://www.linkedin.com/in/lori-goler-6b96921 [ https://substack.com/redirect/4ef573c1-dfc3-4cb9-9563-f8f5032da75a?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Joseph Campbell’s quote: https://www.goodreads.com/quotes/192665-the-cave-you-fear-to-enter-holds-the-treasure-you [ https://substack.com/redirect/c1793762-11c5-4422-85f0-3fcb41985a96?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Zevi Arnovitz on LinkedIn: https://www.linkedin.com/in/zev-arnovitz [ https://substack.com/redirect/1a14c66a-f23d-4fb1-ae80-9ac8b3769afa?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Peopling 101: The Waterline Model: https://christinehaskell.com/blog/peopling-101-the-waterline-model [ https://substack.com/redirect/d66dd208-f9d2-4ba8-9106-c49895287ea8?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Introduction to NVC: https://www.cnvc.org/learn/what-is-nvc [ https://substack.com/redirect/014ccc3d-273b-47ef-9b1e-b33448f86ed2?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• I hate OKRs... and other thoughts about goal setting: https://mollyg.substack.com/p/i-hate-okrs-and-other-thoughts-about [ https://substack.com/redirect/829772c9-e46a-47e5-9705-da05fe19bcb5?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Lessons from scaling Stripe | Claire Hughes Johnson (former COO of Stripe): https://www.lennysnewsletter.com/p/lessons-from-scaling-stripe-tactics [ https://substack.com/redirect/1ea88a75-c2c8-44d1-b9ff-f68a1e9db82d?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• James Clear’s quote: https://www.goodreads.com/quotes/9614600-problem-1-winners-and-losers-have-the-same-goals [ https://substack.com/redirect/65bb37a1-bf29-46fe-be8d-44431cf93c09?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Founder mode: https://paulgraham.com/foundermode.html [ https://substack.com/redirect/7b42fc40-aff8-418c-b769-afd25db7198e?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Stripe: https://stripe.com [ https://substack.com/redirect/bfef23dd-acf5-4867-ae8e-47b78a9b0a58?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Patrick Collison on X: https://www.linkedin.com/in/patrickcollison [ https://substack.com/redirect/8e5049ee-2de2-4be2-9f61-3559f7c0f8d6?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• John Collison on X: https://x.com/collision [ https://substack.com/redirect/f33811e4-e1a3-4772-a31e-8cd8854e9d0c?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Seth Godin’s best tactics for building remarkable products, strategies, brands and more: https://www.lennysnewsletter.com/p/seth-godins-tactics-for-building-remarkable-products [ https://substack.com/redirect/f0d660ec-264d-4894-8aa7-78310e77cbcb?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Eric Antonow on LinkedIn: https://www.linkedin.com/in/antonow [ https://substack.com/redirect/defba6c8-08a4-4f07-8605-23cffdceefd7?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Recommended books:
• The Artist’s Way: https://www.amazon.com/Artists-Way-25th-Anniversary/dp/0143129252 [ https://substack.com/redirect/1ec808dc-dda8-4b9d-994e-861905cd9869?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Scaling People: Tactics for Management and Company Building: https://www.amazon.com/Scaling-People-Tactics-Management-Building/dp/1953953212 [ https://substack.com/redirect/00774dd7-954e-4ae0-b2db-3fe5062d51f1?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Atomic Habits: An Easy & Proven Way to Build Good Habits & Break Bad Ones: https://www.amazon.com/Atomic-Habits-Proven-Build-Break/dp/0735211299 [ https://substack.com/redirect/8f9c5f76-123f-4b6a-85fa-80482a8077b3?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Production and marketing by https://penname.co/ [ https://substack.com/redirect/4baaefc9-e1f4-49e8-9951-cfe9bb9a778a?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com [ mailto:podcast@lennyrachitsky.com ].
Lenny may be an investor in the companies discussed.
My biggest takeaways from this conversation:...
Unsubscribe https://substack.com/redirect/2/eyJlIjoiaHR0cHM6Ly93d3cubGVubnlzbmV3c2xldHRlci5jb20vYWN0aW9uL2Rpc2FibGVfZW1haWw_dG9rZW49ZXlKMWMyVnlYMmxrSWpvME1qWTFNVFV3TkRBc0luQnZjM1JmYVdRaU9qRTRNamczTnpnMU5Td2lhV0YwSWpveE56WTNOVE0wTWpVNExDSmxlSEFpT2pFM09Ua3dOekF5TlRnc0ltbHpjeUk2SW5CMVlpMHhNRGcwTlNJc0luTjFZaUk2SW1ScGMyRmliR1ZmWlcxaGFXd2lmUS5uZld6Q2lPMk12c3BmVVZRazM3ckxHaVFVTzJwUGVYSnRodDVtUGpHYWZBIiwicCI6MTgyODc3ODU1LCJzIjoxMDg0NSwiZiI6dHJ1ZSwidSI6NDI2NTE1MDQwLCJpYXQiOjE3Njc1MzQyNTgsImV4cCI6MjA4MzExMDI1OCwiaXNzIjoicHViLTAiLCJzdWIiOiJsaW5rLXJlZGlyZWN0In0.XZDLELkDAFtKDE3p39qqqXlTQz3F7BTQf9s-Ar5uvQQ?
View Email
The high-growth handbook: Molly Graham’s frameworks for leading through chaos, change, and scale
lenny@substack.com1/4/2026
SubstackView this post on the web at https://www.lennysnewsletter.com/p/we-replaced-our-sales-team-with-20-ai-agents
Jason Lemkin is the founder of SaaStr, the world’s largest community for software founders, and a veteran SaaS investor who has deployed over $200 million into B2B startups. After his last salesperson quit, Jason made a radical decision: replace his entire go-to-market team with AI agents. What started as an experiment has transformed into a new operating model, where 20 AI agents managed by just 1.2 humans now do the work previously handled by a team of 10 SDRs and AEs. In this conversation, Jason shares his hands-on experience implementing AI to run his sales org, including what works, what doesn’t, and how the GTM landscape is quickly being transformed.
Listen on YouTube [ https://substack.com/redirect/239e2bbf-fda1-47c7-a5e0-90a9195352cf?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], Spotify [ https://substack.com/redirect/1afd7638-0969-431b-95f1-a5aa83d3db9b?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], and Apple Podcasts [ https://substack.com/redirect/c06411c6-4bb0-43ee-9f7f-522284d10264?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
We discuss:
How AI is fundamentally changing the sales function
Why most SDRs and BDRs will be “extinct” within a year
What Jason is observing across his portfolio about AI adoption in GTM
How to become “hyper-employable” in the age of AI
The specific AI tools and tactics he’s using that have been working best
Practical frameworks for integrating AI into your sales motion without losing what works
Jason’s 2026 predictions on where SaaS and GTM are heading next
Brought to you by:
DX [ https://substack.com/redirect/755bff0f-6022-4fef-b59f-922cc689a925?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]—The developer intelligence platform designed by leading researchers
Vercel [ https://substack.com/redirect/873d8088-b453-4bda-994c-0256bf9133fe?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]—Your collaborative AI assistant to design, iterate, and scale full-stack applications for the web
Datadog [ https://substack.com/redirect/9add9c34-95c2-4920-8773-fca4d1327a18?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]—Now home to Eppo, the leading experimentation and feature flagging platform
Where to find Jason Lemkin:
• X: https://x.com/jasonlk [ https://substack.com/redirect/9e175653-77e3-4da3-b8c7-f217a18f0b10?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• LinkedIn: https://www.linkedin.com/in/jasonmlemkin [ https://substack.com/redirect/9e9d23b4-c2c9-4377-8cd0-87195d07b8a0?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Website: https://www.saastr.com [ https://substack.com/redirect/30ab507a-9697-43e1-beb5-b6e97388ba37?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Substack: https://substack.com/@cloud [ https://substack.com/@cloud ]
Referenced:
• Building a world-class sales org | Jason Lemkin (SaaStr): https://www.lennysnewsletter.com/p/building-a-world-class-sales-org [ https://substack.com/redirect/ec7ec42f-d187-4716-9ed7-4c13b6af7c61?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• SaaStr Annual: https://www.saastrannual.com [ https://substack.com/redirect/ff1d4f53-b470-487c-9aff-530796909868?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Delphi: https://www.delphi.ai/saastr/talk [ https://substack.com/redirect/125ca3b5-c25d-43cd-af9d-6a98141b1b3e?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Amelia Lerutte on LinkedIn: https://www.linkedin.com/in/amelialerutte/ [ https://substack.com/redirect/7b787522-7ef1-4075-8926-22f931664ecf?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Vercel: https://vercel.com [ https://substack.com/redirect/23eb9502-a6bb-4c8e-ae46-42c21c142275?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• What world-class GTM looks like in 2026 | Jeanne DeWitt Grosser (Vercel, Stripe, Google): https://www.lennysnewsletter.com/p/what-the-best-gtm-teams-do-differently [ https://substack.com/redirect/f0f03c88-941c-402a-be6c-afd9c93671ed?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Everyone’s an engineer now: Inside v0’s mission to create a hundred million builders | Guillermo Rauch (founder and CEO of Vercel, creators of v0 and Next.js): https://www.lennysnewsletter.com/p/everyones-an-engineer-now-guillermo-rauch [ https://substack.com/redirect/93fcd14f-cee2-4002-9dee-c0462c5c401e?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Replit: https://replit.com [ https://substack.com/redirect/80f4ba7b-88b2-4eeb-aa9c-ee8470a90c77?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Behind the product: Replit | Amjad Masad (co-founder and CEO): https://www.lennysnewsletter.com/p/behind-the-product-replit-amjad-masad [ https://substack.com/redirect/f506b2de-563d-4e22-af4c-6725ff2fefb4?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• ElevenLabs: https://elevenlabs.io [ https://substack.com/redirect/5a357deb-306b-428a-b209-40603b437f31?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• The exact AI playbook (using MCPs, custom GPTs, Granola) that saved ElevenLabs $100k+ and helps them ship daily | Luke Harries (Head of Growth): https://www.lennysnewsletter.com/p/the-ai-marketing-stack [ https://substack.com/redirect/468e63cf-35d8-40fd-b76e-9255d275602e?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Bolt: https://bolt.new [ https://substack.com/redirect/affad669-096d-4ca8-bc4d-62ab58a3936a?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Lovable: https://lovable.dev [ https://substack.com/redirect/dad5090b-b8fb-47b1-8530-4e4bea3060f0?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Harvey: https://www.harvey.ai [ https://substack.com/redirect/b452e60d-2531-4076-86bc-6fb2055a47c2?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Samsara: https://www.samsara.com/products/platform/ai-samsara-intelligence [ https://substack.com/redirect/f2204637-6852-475f-b2fd-b309b7c568a2?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• UiPath: https://www.uipath.com [ https://substack.com/redirect/48c5d4d8-0d76-4409-be52-98b105e3cf20?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Denise Dresser on LinkedIn: https://www.linkedin.com/in/denisedresser [ https://substack.com/redirect/f32b93d6-a129-43ee-84a1-04cf86d35130?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Agentforce: https://www.salesforce.com/form/agentforce [ https://substack.com/redirect/8b3bf267-5bd4-4ec9-9b2f-1ac79cd5df70?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• SaaStr’s AI Agent Playbook: https://saastr.ai/agents [ https://substack.com/redirect/1294e53c-3ec6-4b93-bf57-f61849c5a89b?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Brian Halligan on LinkedIn: https://www.linkedin.com/in/brianhalligan [ https://substack.com/redirect/6019d123-f90e-4ec7-9dd0-2b64632264c4?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Brian Halligan’s AI: https://www.delphi.ai/minds/bhalligan [ https://substack.com/redirect/9d9b0995-15cc-4c23-9fb9-d12eceadb899?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Sierra: https://sierra.ai [ https://substack.com/redirect/873ad69b-1fbf-423e-a8a6-928f0ffbe051?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Fin: https://fin.ai [ https://substack.com/redirect/a35b62a5-286c-4d84-9ffa-ef22ef96d691?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Deccan: https://www.deccan.ai [ https://substack.com/redirect/fd22017c-e6a8-4814-8ee4-c7d8a7e02abc?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Artisan: https://www.artisan.co [ https://substack.com/redirect/cb5a4a7d-55e4-415d-b0e9-ea22bd326614?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Qualified: https://www.qualified.com [ https://substack.com/redirect/c1f5775f-7b68-426c-931a-2cbb4bdfa791?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Claude: https://claude.ai [ https://substack.com/redirect/2a9cdc5f-f7ea-49a0-bdcd-90d856977743?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• HubSpot: https://www.hubspot.com [ https://substack.com/redirect/4d6b9b00-eb5a-4507-9e8c-02ed328f3305?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Gamma: https://gamma.app [ https://substack.com/redirect/65fb22b4-f8bc-4091-baba-798007029d96?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Sam Blond on LinkedIn: https://www.linkedin.com/in/sam-blond-791026b [ https://substack.com/redirect/25dc2f83-2bb3-475b-8e9e-0a14e355f6aa?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Brex: https://www.brex.com [ https://substack.com/redirect/625e3c0a-1772-4f95-82b9-7998c387f18e?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Outreach: https://www.outreach.io [ https://substack.com/redirect/6b2e5a60-a682-426a-b061-4e581852a946?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Gong: https://www.gong.io [ https://substack.com/redirect/f1f9274a-ae15-422b-9113-6593cbfc90bc?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Salesloft: https://www.salesloft.com [ https://substack.com/redirect/80cca273-b9f9-498d-8df3-87a21948260a?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Mixmax: https://www.mixmax.com [ https://substack.com/redirect/b9410bd3-0d49-4a73-8b48-25d1b52f9cb6?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• “Sell the alpha, not the feature”: The enterprise sales playbook for $1M to $10M ARR | Jen Abel: https://www.lennysnewsletter.com/p/the-enterprise-sales-playbook-1m-to-10m-arr [ https://substack.com/redirect/d33aa15d-f84a-47c6-ad2f-ec90873e821d?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Clay: https://www.clay.com [ https://substack.com/redirect/3edaab53-6755-4abe-a1f2-8256d136b0bd?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Owner: https://www.owner.com [ https://substack.com/redirect/04b52d07-d70b-49f4-9e2e-acf6cf59ccc3?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Momentum: https://www.momentum.io [ https://substack.com/redirect/3491442b-e590-47c6-b911-2b3f5922f478?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Attention: https://www.attention.com [ https://substack.com/redirect/fb59968e-ac6e-4437-9e8b-ec6ca85147fa?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Granola: https://www.granola.ai [ https://substack.com/redirect/b1ac9deb-fb1a-4585-99cf-d28d3f0a89d6?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Behind the founder: Marc Benioff: https://www.lennysnewsletter.com/p/behind-the-founder-marc-benioff [ https://substack.com/redirect/790f48e6-1d1a-4b62-a0ba-a631153756ff?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Palantir: https://www.palantir.com [ https://substack.com/redirect/c3da30ec-cf65-484d-ae5f-bb3564c38587?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Databricks: https://www.databricks.com [ https://substack.com/redirect/f4abee2e-afb1-4610-aad9-856d132475d7?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Garry Tan on LinkedIn: https://www.linkedin.com/in/garrytan [ https://substack.com/redirect/3c7441a7-4654-4740-8a0b-3826f98c2a8c?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Rippling: https://www.rippling.com [ https://substack.com/redirect/774e381a-7050-49c2-8142-57a8976f7b3b?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Cursor: https://cursor.com [ https://substack.com/redirect/e68ab058-153f-4e0f-8690-d82ed6c3d434?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• The rise of Cursor: The $300M ARR AI tool that engineers can’t stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell [ https://substack.com/redirect/09c282a9-3531-4f60-ae52-18a014cf7518?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• The new AI growth playbook for 2026: How Lovable hit $200M ARR in one year | Elena Verna (Head of Growth): https://www.lennysnewsletter.com/p/the-new-ai-growth-playbook-for-2026-elena-verna [ https://substack.com/redirect/f12c230d-4126-43ed-87c4-55f107df2dd8?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Pluribus on AppleTV+: https://tv.apple.com/us/show/pluribus/umc.cmc.37axgovs2yozlyh3c2cmwzlza [ https://substack.com/redirect/ff8f54ef-4695-43fe-afb9-23efe3697abf?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Sora: https://openai.com/sora [ https://substack.com/redirect/634aade1-c80d-4c4d-897d-1a5cda51dfa1?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Reve: https://app.reve.com [ https://substack.com/redirect/1ad95de4-610b-4fde-97f1-1d9454656395?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• Everything That Breaks on the Way to $1B ARR, with Mailchimp Co-Founder Ben Chestnut: https://www.saastr.com/everything-that-breaks-on-the-way-to-1b-arr-with-mailchimp-co-founder-ben-chestnut/ [ https://substack.com/redirect/5ba089d8-b341-4840-baa1-4cf38971f6c3?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• The Revenue Playbook: Rippling’s Top 3 Growth Tactics at Scale, with Rippling CRO Matt Plank: https://www.youtube.com/watch?v=h3eYtzBpjRw [ https://substack.com/redirect/d83f9a2f-cb68-4929-a4c6-28b1bc70eae7?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
• 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling): https://www.lennysnewsletter.com/p/10-contrarian-leadership-truths [ https://substack.com/redirect/ec4c01cd-42ae-4c40-8160-c405479681c1?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
Production and marketing by https://penname.co/ [ https://substack.com/redirect/6d4e2d2a-f9fe-40e1-ad2f-301811877c0b?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com [ mailto:podcast@lennyrachitsky.com ].
Lenny may be an investor in the companies discussed.
My biggest takeaways from this conversation:...
Unsubscribe https://substack.com/redirect/2/eyJlIjoiaHR0cHM6Ly93d3cubGVubnlzbmV3c2xldHRlci5jb20vYWN0aW9uL2Rpc2FibGVfZW1haWw_dG9rZW49ZXlKMWMyVnlYMmxrSWpvME1qWTFNVFV3TkRBc0luQnZjM1JmYVdRaU9qRTRNamt3TWpjeE5pd2lhV0YwSWpveE56WTNNamMxTVRZNUxDSmxlSEFpT2pFM09UZzRNVEV4Tmprc0ltbHpjeUk2SW5CMVlpMHhNRGcwTlNJc0luTjFZaUk2SW1ScGMyRmliR1ZmWlcxaGFXd2lmUS5GXzZpMS1NeDJxQWp3NExWTGFkV2pONmxnSngzNFpiNmhMNmFCdkFmWmRZIiwicCI6MTgyOTAyNzE2LCJzIjoxMDg0NSwiZiI6dHJ1ZSwidSI6NDI2NTE1MDQwLCJpYXQiOjE3NjcyNzUxNjksImV4cCI6MjA4Mjg1MTE2OSwiaXNzIjoicHViLTAiLCJzdWIiOiJsaW5rLXJlZGlyZWN0In0.afIfaNJ0WBlGzZIqaCNvwa6RDMeItX9MrWDKc09IGww?
View Email
We replaced our sales team with 20 AI agents—here’s what happened | Jason Lemkin (SaaStr)
lenny@substack.com1/1/2026
Substack[https://eotrx.substackcdn.com/open?token=eyJtIjoiPDIwMjUxMjIwMDcyNjEyLjMuZjA3ZDU0ZjZiMGRmYzlkYi5jcGRuMDJncUBtZy1kMC5zdWJzdGFjay5jb20-IiwidSI6NDI2NTE1MDQwLCJyIjoiYkBlbWFpbC5nb21vZHVsci5jb20iLCJkIjoibWctZDAuc3Vic3RhY2suY29tIiwicCI6bnVsbCwidCI6bnVsbCwiYSI6bnVsbCwicyI6MTA4NDUsImMiOiJ1bmZpbmlzaGVkLXN1YnNjcmlwdGlvbiIsImYiOnRydWUsInBvc2l0aW9uIjoidG9wIiwiaWF0IjoxNzY2MjE1NTcyLCJleHAiOjE3Njg4MDc1NzIsImlzcyI6InB1Yi0wIiwic3ViIjoiZW8ifQ.Z1AvkAcGarBfMFrTdE2MhCPXJ-JY6mwp9tFaXiqUfvI]
You’re now subscribed to the free edition of Lenny’s Newsletter.
͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏
͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏
͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏
͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏
͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏
͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏
͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏
͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏
͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏
͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏
͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏
͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏
͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏
͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏
͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏
͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏
͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏
͏ ͏ ͏ ͏
Lenny's Newsletter
[https://substackcdn.com/image/fetch/$s_!8MSN!,w_80,h_80,c_fill,f_auto,q_auto:good,fl_progressive:steep,g_auto/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F441213db-4824-4e48-9d28-a3a18952cbfc_592x592.png]
[https://substackcdn.com/image/fetch/$s_!oVYJ!,w_728,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fbucketeer-e05bbc84-baa3-437e-9518-adb32be77984.s3.amazonaws.com%2Fpublic%2Fimages%2Faf7625f9-5086-4a07-b266-3ffbe60f09b6_480x260.gif]https://email.mg-d0.substack.com/c/eJx0kr2OnTAQhZ_GdCB7_AMUFKuVKPIAkVIh_4y51oLNYnuTm6eP4CpSmnRHmvE5n47H6oJrOp9TjT7EkB_o2lxNtmc4SkixcZPi2kvX4MR6pYBJ2UODuw7bsmLEUxd0iy7_TJUUzWMCydXomHJomaGAcoR-4GZg2nlAzZswAQXJACjtQTHoeOdp76TwylDn7ehMZw8XKayfRNB9bR3tLrai7Udn096EvPgTb5apnBWbbXqUcmTC3wjMBOa_29bF6wGBOex6RQKzx2If95LICwGWvv_4RoARePeLriUReP98Cf62puSuwbYcZ1pPzDl8IeFvuSAeBOZXJsgrVV6WEmZT7QcWxLNFKo2xg2iN1rwVvMd2lGxotTMcDPb9OIgu807v-neK-md-kUqYj2q2YG95Y-dbat8rkH5sJR1UKzTtWwNKtdx7g4p6Ohq1iIH-AkW7NfjmqGaxad9rDOW5YNRmQ_fq65Wgr49egpsYHYRszskQQe9WuzXtydXtvOvO1bi06xCnDWN8NuW_R1MznpehACWZpII2XxP8CQAA__-KmcZ5
You’re now subscribed to the free edition of Lenny’s Newsletter. I’m honored to
have you on board!
To dive right in, check out my most popular posts
[https://email.mg-d0.substack.com/c/eJx0kDvOnTAQRldjdz-yBz_uLVxEitgG8mMAK2ATP350dx9BmjSpR3O-o-NtwzWXj-lpiSnWDcNX7a76Es8Wc6LBqNEuMlA0XCsFXEoNFA8b93nFhMU2DLNt_1yVFHQzwNzbC84lgPWKOw7spV-as4D-rbWj0QADyQEY06A4DOOwMB2kWJRjYfHv4AZ_hsRg_U0EO9avwIbbrVn_a_D5oLHOS8HHxbTSke5ma-2sZPxBYCIwXdc17JjSpya86o6tYbk_CUy2-C1-Ixmnmksj48-WT3p2N_t8HD3F9pkxWbdj-Is-u9ujt3eTOQbD2UtIWowjgj0Cw5qPHPr-8GntLuTDxmSeedr-27dXLDdQgJJcMsHot4E_AQAA__-IIYe8],
or explore posts about AI
[https://email.mg-d0.substack.com/c/eJx0kD1uhDAQRk-Du0XjwTZL4SIN10D-GVgrYIh_gvb2EaRJk3o073t6zhRa9vTWNc4hhvwi_8jVZpfCUcIemdeqM7P0jDTvlUIuZY-MNhPWaaFIyRTykyl_rkoK9tK9kEDPgQ9glXl2YiB0oAYruaPOgWdBI6DkiAA9Ko5t187QeylmZcHPbvC2dYePgMtXI2BbHh7ay60Y99m6fWMhT3Oi20WXVImt-lXKkZvuo8GxwfE8z3alGN850plXKoXS9dngWBocTWBHtZPbt63GUN4TRWNX8r-wo9o1OHNVmILXHJ5CsqRtI-CebJd9231dbyLL1fp9MyHqe5CVf4vWTOkCClSSSxDAvjX-BAAA__9Wm4Kh],
career growth
[https://email.mg-d0.substack.com/c/eJx0kD1uhDAQRk-Du0XjwTZL4SIN10D-GVgrYIh_gvb2EaRJk3o073t6zhRa9vTWNc4hhvwi_8jVZpfCUcIemdeqM7P0jDTvlUIuZY-MNhPWaaFIyRTykyl_rkoK9tKeXMeFUwBPO4CbBXLVd93gpBroaTgLGgElRwToUXFsu3aG3ksxKwt-doO3rTt8BFy-GgHb8vDQXm7FuM_W7RsLeZoT3S66pEps1a9Sjtx0Hw2ODY7nebYrxfjOkc68UimUrs8Gx9Lg6EwiSuyodnL7ttUYynuiaOxK_hd4VLsGZ64SU_Caw1NIlrRtBNyz7bJvu6_rTWW5Wr9vJkR9j7Lyb9WaKV1AgUpyCQLYt8afAAAA__-K04RH],
product
[https://email.mg-d0.substack.com/c/eJx0kD2ypSAQRlcj2bWgFRwDgknchsVP46VGwYFmrLv7KX3JS17c1ec7dZwh3HL56JZCTLG-0b9qs9WVeFLMiXmtBhOkZ6jFpBQIKSdgeJi4rxsmLIbQr4a-XZUc2Vu72doZcXJmtoNQgQeBkxV2tiLIGRyLGjhIAcD5BEpAP_SBT16OQVnug5u97d3pE4ftbzfyY3t53t9uZNyf3uWDxbqGgo-LptKQ7fpNdNZu-N3B0sFyXVe_Y0qfmvCqOxJhuT87WKiD5SzZN0fsbHZ1-ThaivRZMRm7o_8ins3u0Zk7xRq9FvzXKFnRthv5s9tv-ci-7Q-W1WZ9PkxM-lll9GPWVrHcwBGUFJKPnP3T8D8AAP__eTCF-g],
product management
[https://email.mg-d0.substack.com/c/eJx0kLsOnDAQRb8Gd4vswY-lcJGG30B-DKwVbBM_gvbvI0iTJvVo7jk6zjTcc_nqnraQQv2gf9VuqyvhbCEn4rWczCY8Qc2UlMCEUEAwmnCsOyYspqFfTfvnKgUnHz05o97zNCvmLN8YzpYCM4pJN80wCUWCBgqCAVCqQDIYp3Gjygu-SUv95mZvR3f6RGH_NXAa95en4-3WjPs5uhxJqOtW8HHRrXQkh_60dtZh-jHAMsByXdd4YErfmvCqB7aG5f4cYGkDLGfJvrv2iiaZPWJq5Ox2dTnGnkL7rpiMPdD_3T67PYIzd5Q1eM3omwtStB04fQzGPcfs-_EASO3W52hC0g-ftP8G7hXLPchBCiYop-S3hj8BAAD__2HViI4],
growth strategy
[https://email.mg-d0.substack.com/c/eJx0kLvO3CAQRp_GdL8Fs1z-LSjS7GtYwAxeFBscLrH27SM7TZrUoznf0Qmu01rqx44cU07tTfjVhm-hpqOnkhla_XBRISMrjNYglDLAaHdpW1bKVF0nXFz_56qVZG9rTHiCcUJGr_lT0PM7GqSgOaJwESNLFjgoAcC5AS1gfsyRG1Qyas8xhif6ORyYOay_Jsn39Qv5fLl1F37OoewstSVWul1sr4PYZt-9H216_JjgNcHrPM95o5w_LdPZNuqd6vU5watP8FprOfubHcMvoez7yKl_FsrOb4R_gcfwWwruKrEktIJ_S8Wq9ZPk9-y8lr3g2G4qa8Nj2V3K9h5l_b9VR6N6ASVoJRSXnP228CcAAP__sySFbg],
hiring
[https://email.mg-d0.substack.com/c/eJx0kD0OnDAQRk-Du0XjwTa7hYs0XAP5ZwxWwBD_BO3tI0iTJvVo3vf0nKm0HPmrWwoxxbKSf5Vmi8vxrPFIzGs1mCA9I81HpZBLOSKj3cRtXihRNpX8bOo_VyUFW7X4hFGOw1sM9sOVglEF4MoObwnOkxxY1AgoOSLAiIpjP_QBRi9FUBZ8cB9ve3f6BLj86gTsy8tDf7tV43727thZLHPI9LjomhuxTa-1nqUbfnQ4dThd19VvlNK3JLrKRrVSvj87nGqH0xpzTAs7m53dse8txfqdKRm7kf8LPJvdojN3iTl6zeEtJMvadgKe2X459sO37aGy0qw_dhOTfkZZ_W_VVijfQIFKcgkC2G-NfwIAAP__94OD1A],
B2B
[https://email.mg-d0.substack.com/c/eJx0kL2ypCAQRp9GsrGgBZwJCDbxNSygG4daRZeftebtb-lNbnLjrj7fqeNtpWXPH9NSiCmWN-GjNFd8jkeNe2Jo9GCDQkZGjFqDUGoERpuN67xQomwr4Wzrj6tWkr1NGJ9cW-sVkiZHTykc11IE9_LDoJGzaICDEgCcj6AF9EMf-IhKBu04Bv9C1_sDE4flXyf5tjyQ95dbtf5v7_eNxTKHTLeLqbkRW8271qN0w58Opg6m8zz7lVL6lERnWalWytdnB1PtYHLg2NHc7PdtaynWz0zJupXwm3Y0t0ZvrwxzRCP4UyqWjeskvzf7Zd92bOuNZKU53Dcbk7kXWf01aSuUL6AErYTikrP_Br4CAAD__5uig4c],
marketplaces
[https://email.mg-d0.substack.com/c/eJx0kD0OnDAQRk-Du0XDgA0pXKThGsg_Y9Za2xD_BO3tI0iTJvVo3vf0jKq0H_krW3I--fIm-ypNF5P9Wf2RmJViVI5bRnKYhcCB8xkZReXDtlOirCrZTdV_roJP7C1hAXCLosHM2jmlrBgJR4PAudZ8XpiXCMgHRIAZxYD92DuYLZ-c0GCd-WF1b06bAPdf3QRxf1nob7eqzKc3R2S-bC7T4yJrbsSCfNd6lm782eHa4XpdVx8opW9JdJVAtVK-Pztca4drVPlD9QzKUGFn05s5YmzJ1-9GSelA9i_2bDp4o-4em7dygGXiLEvdTfCM9_sRD9vCw2alaXtE5ZN8pln9b9tWKN_ACQUfOEzAfkv8EwAA__-uLYeE],
or how the best product teams build product
[https://email.mg-d0.substack.com/c/eJx00L0SnSAQBeCnkU4H9wLeW1Ckua_hALsqEwTDTxzfPqNp0qTe2XO-Oc5UWlO-dIuLj75shH1ptrjsj-pTZKjVyywSGelxUgpGKSdgtBsf5pUiZVMJZ1P_uSop2KYndCjhPU4foSQQSpyMlS8kehvhzId5DRzkCMD5BGqE4TUsfEIpFmU5Lu6DdnAHRg7rr07wfe2RD7etGvdzcGlnvsxLpseia27Egt5qPUr3-tHBt4PveZ5DoBivEuksgWqlfH928K0dfLd09nWjq7fNB-yPnLC5yo5mZ5f2vUVfr5misYHwb8HRbPDO3MvMHvXI30KyrG0n-MMY1rQnbOFpYaVZTLvxUT8IVv-7ciuU70ABSo6SC85-a_gTAAD__yNOi0I].
I’ve got an audio version of each newsletter post if you prefer to listen vs.
read (find it on Spotify
[https://email.mg-d0.substack.com/c/eJx00D2L3DAQxvFPY3VnxmNJ3i1UXLNwkBSB9EYvI68SW9LpJcHfPnjTpEk9zMOPv9WNtlRO1aMPMdQnubfaTbUl5BZSZE7JWXvhGKlpkRInIRZkdOiwrxtFKrqRW3X75yoFZ08FdwTHlxstdLfzrDlYDe4mbxOXeBeGBYWAYkIEWFBOOM6jh8UJ7qUB5-3dmdFmFwG3z4HDsb05GC9b0_bnaNPBQl19oZdFtdKJ7erZWq7D_D7gY8BHyhTHmlML_rw-BnzUZ_o94AM-Pnp8B_n5tRX77Ys_8_eUfrDczWrTcfQY2rlS1GYn93c7d7MHq68oa3BqghsXrCgzcHgJxi0dyfW9vGi1G5cOHaLaKcaTtf8G7pXKNchRikkAB_ZL4Z8AAAD__4iRh0U],
Apple
[https://email.mg-d0.substack.com/c/eJx0kL2u3CAQRp_GdGvBGPBuQZHGr2EBM_ai2ED4ibRvH9kp7m1ufTTzHR1vG-2pfEyPW4ihvgkftbvqS8gtpMjQ6MluChkZMWsNQqkZGJ02HOtOkYpthKtt36hWkr2NnTUJmBC98orUU8P8slJxiU_vuQcWDHBQAoDzGbSAcRo3PqOSm3YcN_9CN_qMkcP-Z5D83B_Ix8utWf979Olkoa5bodvFtNKJHebdWq7D9GuAZYAlJ_S2tjranA-6bgZYev0iAywHxfipj0IWLxBQPAWfhNSvieXuVp_Os8fQPitF6w7C_1O5uyN4ezVaAxrBn1KxYtwg-S007ulM2I9ym9buMJ02RHPPsfZj716pXA8laCUUl5z9NfAvAAD__267i50],
YouTube
[https://email.mg-d0.substack.com/c/eJx0kL2SpCAQgJ9GsrFaBHQCgkvmNSygG4c6BY-fm_Ltt3STTTbtrv76q8-ZSmvKp27RhxjKm_BRmi0uh6OGFBlqNRovkZEeJqX4IOXEGe0mbMtKkbKphIupP7ZKCvbWI7l5fgoSM3o1A0giw9VsPFg-gCMWNAcuB84BJq4G3o-9hwml8MoCevdE27sDI_D1XydgXx8I_eVWjfvbu7SzUBaf6XbRNTdim37XepRu_NPxV8dfn8-nP1OrzdJ1cA0FbBTjWTIZLOxodnFp31sM9VwoGrsRfrOOZrfgzBVhCagHmIVkWdtOwP2xX9OesG35VinNYtpNiPrGs_pr0FYoX0DBlRwkCGD_Nf8KAAD__1bVgq8]),
and my popular podcast, Lenny’s Podcast (find it on Spotify
[https://email.mg-d0.substack.com/c/eJx00E3P1CAQwPFPA7dtYAp098DBqI0HXxITPXhpgIEu2kLlRbN-etP14uU5T2bml78zza-5PHRPIaZY7x4vtdvqSjxazImiVqMJEqnXfFIKuJQTUL-buC2rT76Y5nEx7b-pkoLe9U0Jpa7TyI0yV4XguHMouBr51QqOjEYNDCQHYGwCxWEYh8AmlCIoyzC4G9rBHZgYrD-JYPt6QTactmbcj8Hlnca6hOKfFt1K93TT99aOSsZXBGYCcz58GuqRWwyPc4PAXO_5N4EZ8DP_8OXb23evP6U__P3X8NE49p2Mc41kfBNuzHvlHABXggekR7eLy_veU2yPxSdjN4__fh7dbtGZM9YSUXN2FZIWbYlgT9mw5j1j38qTXLvFvJuY9OZTetD2YvhefTkPClCSSyYY_aXhbwAAAP__1mSNCQ],
Apple
[https://email.mg-d0.substack.com/c/eJx00U3OnDAMBuDTkB3IGALDIotuuAZKYoeJCkman1Zz-2qmldrNt_UrW49tqyufMb9UC84HX55MfWmm2OxT9TEIUsuknSTBalyXBUcpVxR8a38dJwfOujIduv6XLnIWT4X6wWhXCWgmuY3kJrM9tgeQtowOUXiFgHJEBFhxGXGYBgcrydktBsjZjcxgEwXA80c3w332BMPbVrX9Pth4C18Ol_ljUTU3Fpd61ppKN33rcO9wT5GsLrUMOqWL3z0d7q38SzrcLw7hVfq_hT7lSM3W_szxV332Vmfm3OHuaVxw3RAmkCI1c9h43y34-jo4aHMx_SGkZi5v9ft2hyc1wmOWIivTzfCBDme8I7UrfzYozVC8tQ_qwxD1yz-0wvk9cMZFjhJmED8V_g4AAP__nh2VEQ],
YouTube
[https://email.mg-d0.substack.com/c/eJx0kD2O5CAQRk9jsrYAU7g7INjE0QZ7AwuoshutDR5-puXbj9yTTDJxqb739LyttKZ8mhaXEEN5Et5Kc8XncNSQIkOjB7sAMjJi1FoKgFEy2m3Y5pUiZVsJZ1t_XDUo9jSc3919tANYIdB7DXxwAEJ4C6geBCwYySUIKTkfpRayH_qFjwhq0Y7j4h_oen9g5HL96BTf1xvy_nKr1v_vfdpZKPOS6e1iam7ENvOs9Sjd8KeTUyen1-vVn6nV5uh66OTkOzn9pRjP8i-ht6Wyo7nZp31vMdRzpmjdRvg9dzS3BW-vDnNAI_hdAcvGdYq_of2a9oRty2-b0hym3YZotgvA6q9NW6F8DSqpQQBXnH0a-RUAAP__WqeDTw]),
where I interview world-class product builders to uncover concrete, actionable,
and tactical advice to help you build, launch, and grow your own product.
CONSIDER UPGRADING TO A PAID SUBSCRIPTION
With the free subscription (which you’re currently on), you’ll only see part of
each post. If you upgrade, for just $200/year, you’ll get:
1. An invite to a thriving private Slack community of paid members (learn more
[https://email.mg-d0.substack.com/c/eJx0kEturDAQRVeDZ43KhW3ogQdvwjaQPwVtPTDEn6DefQSRokwyLJXuuVfHmULLnt66xjnEkF_kH7na7FI4Stgj81p1Zpaekea9Usil7JHRZsI6LRQpmUJ-MuXXV0nBXtoAWTlwxKcDA44rMk_ueO_FwDkNHQsaASVHBOhRcWy7dobeSzErC352T29bd_gIuHw0Arbl4aG9thXj_rdu31jI05zo3qJLqsRW_SrlyE33r8GxwfE8z3alGN850plXKoXSlWxwPBoc3b5tNYbyZke10881UTR2Jf_NPKpdgzOXjCl4zWEQkiVtGwF3c7vs2-7reoNZrtbvmwlR372s_Cm2ZkoXUKCSXIIA9qnxKwAA__9qDoXS])
2. Full access to every newsletter post (including the 5-year back catalog)
3. A year free of 15+ world-class products
[https://email.mg-d0.substack.com/c/eJx0kD1uxCAQhU9jurVgDHi3oEiz17CAGXtRbHD4ibW3j-w0aVJMNXrfe_q8rbSk_DYtziGG8iK8leaKz2GvIUWGRg92VsjIiFFrEEqNwGizYZ0WipRtJZxs_fPVSrKXuQ8a9DjYEWm03CoYyN3lw81CkfCALBjgoAQA5yNoAf3Qz3xEJWftOM7-ga73O0YOy1cn-bbckPfntmr9Z-_TxkKZ5kzXFlNzI7aaV6176YaPDp4dPI_j6FeK8V0iHWWlWimfyQ6e-3k5YfN1t6WwvbnJp21rMdT3RNG6lfCXuje3Bm9PHVNAI_hdKpaN6yS_uvslbQnbeqFZaQ7TZkM0VzOr_6pthfIJlKCVUFxy9m3gJwAA___Hd4bn]
Many readers expense it out of their workplace’s learning and development
budget. Here’s an email to send your manager
[https://email.mg-d0.substack.com/c/eJx00cGO3CAMANCvCbeJgAQmOXDYrWbUaltV1W4Pe4oAmwxtgDTAtrNfX2Xm0ktvli3bT7bVBee0XVWNzkefLwiHXE22m1-LT5GAkp12AggqdpSSMyGOnGDQfplmjLjpgjDp8k9Vip5clBaGDQNnnR47HEcNEnqJjo1WD9bQgXjFKReMc0qPXDLedq2jRxC9k4aCsyOY1q4QKZ9_NT0N8wFou9uKtj9bmwLxeXIb3iyqbBXJoi6lrLnpHhp-bvgZks3tnNK84N5wz9SAsexhw88sTc_vOdHDy7eH0-nxw5-n32-fP74E5t5P_eMX__wDXz89fXXfXxfa8DOCL2StZrIphBp9uU4YtVkQ7vvXahZv9X64yYNidOgF2ZRpenpTtnMKCeqy3fi5GkhB-6gWjPFKyn-fUDNu-8CeS8EE7Sl5U_xvAAAA__8tN5MM].
I guarantee that you’ll get a 10x return on the spend of this newsletter in
impact on your product and career—or your money back.
Upgrade to paid
[https://email.mg-d0.substack.com/c/eJx0kk1vozwUhX-N2QX5A0OzYBEF5X2TKamqoV_ZIONrwAnYDNgl6a8fJdOpZtPt9fXxOc-xFE41dryk3tTa6KlVsJh8NclRD05bE0AaM1FzCFRKkjimhPOEBqoXuisbZdQonIJSuH9OYx4FbXpXx5xJIQBDteQJJYoRoDThXBKAKgp0SjHlhFKMExoTGrKwxgnwqI4rDLVcQhXKAQymzS8U4b5ZAA6v3pyQp1DaPtBTWY_q5iV1o1dBl7bODRNiK0Q3iG7meQ47ZcxlMmqeOuWcGq83Ed18hqwUYhvv-nKyfpQKsewbEIjG1zUp-kHoxiCW3d5dyFbJk_UO0XhELEvIeYgworGzJ3XbuuyIpM-XV9qdtkeL8-MbyYuneZ-tpm3ftbDexnkh6f64Pe-LJ5brWR9e23l7tOf9x1v0kK3YvpCX-_VukCzXD3o3w8vW5cUq2mdP-n69-4CX7XV-FP89HwVdEljvluFDYrktlsy4gzWtv1-sH4E17eHsC7Nx-c__D--P8-vhR5bZz2y9Au37v8k-h19cvoAtZg2NcsHgq1LavvdGu0upjKg6BX96GHzVaSmu3EoNKcF3EQ_GtEIRvmmHje0t-O5WRjD5CmwvtElvXQXu28_oJzVeBSMac8JxhIP3lP4OAAD__2Jf8Os]
P.S. If you use Gmail and have 10 seconds to do me a big favor (to help convince
Gmail to keep this newsletter out of the dreaded Promotions folder) 🙏
1. Reply to this email with a quick “hello!”
2. Move the email to your Primary folder
[https://substackcdn.com/image/fetch/$s_!o6ee!,w_1100,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F5fb5572c-5fc0-481a-b4c9-9a1077756acc_1075x268.png]https://email.mg-d0.substack.com/c/eJx0ks2OpSAQhZ8GdhooQa4LFjed-BqGn8JLRsEW7Jk7Tz9RM5nZ9O4kVZxz8lHOVJzz_tZHCjHF8kLflMMWt8etxpyo131ngvQUNVd9D1xKBRRXE5dpxoS7qegnU_-b9lLQl1bdIJQM6NWgBjt0GAx_SGAiWCbQIo0aGEgOwJiCnkPbtYEpL0XoLfPBDd62bvOJwfxJBFvnxrP27FaN-9G6vNJYprDj1UXX_UC66FetWyHdk8BIYPy77Xw6HxAY42pmJDAGrO51LYkyEeC5RyTACXyEyRw1E_j4vEX3nHP252CZtj3PO5YSv5B0z1IRNwLjnQnyTJWnpfyX3Gy51GZFH01butas5ndO5me560gYt8Mu0V3y6lYuKYM9SbpGBsca8eCmscINzWA4U0rJ3jg3cabkL-gf7ZZmuh12cnldjxTre8Jk7IL-pnJHmPM7p-g1Zw8h6a4tEexi1855zf5Y9gtqOazPq4lJL5jSm9ZvT-MouJ-GAnrJJROMfmn4EwAA__-v3sD7
Private podcast setup:
To set up your podcast app, click this link
[https://email.mg-d0.substack.com/c/eJx0ks9uozAQh58G34qM-Zc9cKCJopIWqlZJmvSCsD0OTsCm2KxDnn6V7GUvexppRjP69M2PNRZOepyzSQmppGmBP5mJGjbKwUqtEM-SsBExR5AFaZKQII5TgqBvZFefQMHYWOB1Y_-ZJnGE2myRhgBcJE2QLoJYUAFBSrlgUSpSAowgmRFM4oAQjFOSBMQPfYFTHkcioZgL9otTnw1cYXL68SLcn5449u9stmEXn-keSVOLER4smR0nQF3WWjsYL8w9svbI2jnnd6DUbBQ404G1MN43PbLupLGgvHBt9eVeVzBvAkb284F0l-KscXk-BuV256pVboq-a_mySMotI9W5uFbbXVhKJ78PrSvO-lrdjuR9Vbjyxua35WZgYSnf5cbxr8KW2zyqVjv5ttzc-Ffx6FPyeT4eKvx2qDr-sneFwv5n_p2vhs3-5WN4etbiOXevH2H_3hSMli2NzfV16dIfuTOwQMNEa6b7flLSzjWohnbA_yoYJtpJ1tx_V0ueBXgRxWjMqBfhhyj_pHvNp-7hAZmJct03UmUPTcj-NweTgfF-MCJJHMQ4wuh3Rv4EAAD__7rWwdk]
on your phone.
© 2025
2443 Fillmore St., #380-8231, San Francisco, CA 94115
Unsubscribe
[https://email.mg-d0.substack.com/c/eJx0ks1uozwUhq8G74qMbZx0wSJfUz6RaajayV9ng_wHOMGGYhNCrn5EZjOb2Z6j8-p9Hh3BvKrafkoGW2qrXa3kkxu4E73uvG4tkAnFrIwlUEm0oBRFcbxAQBmmm6JSVvXMK1kw_9eWxgTUSakIKglmlAqBmeC4jERcMrpcUBHxJQE6QRDFEUIQLhCNUIjDEi5kTErKoSzFs-Sh6KSFqPoOCDTVk4Th3M0zcQlFa4B2RdmrR5fE94MCTVJ737kArwKUBigdxzFslLWTs2p0jfJe9fNlgFImZrwApVI7xhtVPGICnPr2omyA12raRAIdphNqLtm5hdvzV7Td7cd8vXKZ_e8q8GfJjh_63cQR_390mWlq-ZLR7U6g_Jzd8t0eb_Wof53qMTu3t_x-wfl9f8t3Ynp72XQCb_W73ozymPntbkXy9V6_vWzu8pjN8ws75fWXuTUndPBfx8ZlFob847lCh0_3Mz2nRj29-vs3krtpHNZ-qV8HM61ogQ_tNf9BQDfwQrTGDFb7qVB2hpR_NHUDb7Rgs4BCyySCSxKDPuEBgQ8LYdWaVg7NwxVwA5etYdomD5XA__NXBqf6OZAgGkcxJBBcE_Q7AAD__3-jz30]
Get the app
[https://substackcdn.com/image/fetch/$s_!IzGP!,w_262,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack.com%2Fimg%2Femail%2Fgeneric-app-button%402x.png]https://email.mg-d0.substack.com/c/eJx0kb2u5CAMhZ8GukTEATJbUKx0Na8R8eNk0A2QBbPSvP0quc0027g5R8effbwl3Et9m563mGN7YRhad83XeFIsmQejZ7upwNFMi9YwKbUAx2Tjse6YsVrCsFr6ULWS_GWCtIDg5GMOflkQwW8olVPT4h5ei5lHAwLUBCDEAnqCcR43sQQlN-1E2Pyv4EZ_hixg_8OkSPsQxHixkfXfoy-Jx7ZuFW8WQ7UjP8yL6Gxs_s3gyeD56WbwtOf5M4dGpeJQMcSKntj87JRWb9Np457Z_HV5kq3fSDHvDPQtl0yYic1f98ZhK4WwDq4TlczP7lZfUuo50nvFbN2B4Yfq7O6I3l7vXGMwk3hIxatxTIo7adxLKqEf9T6qdRdKsjGbA3N-c_pvNb1hvQIlaDUpIQX_a-BfAAAA__-NTZ4mStart
writing
[https://substackcdn.com/image/fetch/$s_!LkrL!,w_270,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack.com%2Fimg%2Femail%2Fpublish-button%402x.png]https://email.mg-d0.substack.com/c/eJx0kUuO3CAURVcDs7IwP1cPGERyagNZgAW8ZxeKAYdPlNp9ZHc66kEy5HJ1OOh623DL5WV6WkMK9Ylwq91VX8LRQk4UjBZ2VUDRjJPWfFRq4hSjDfuyYcJiG8Ji26dbrSR9GgXKIhsne1f6LtByBZNDgZK_oUKYaDCccTVyztjE9cgHMaxsAiVX7Ris_g3c4A9IjG8_iGRxuwEbTrdm_ffB50hDXdaCl4tppSPdzbO1oxLxhfAH4Y_P7fMYttQPIh69xaXmXjwSMX-UCNdnHhFCj0TMF_dP6HNqmBoR85pzw_IR23jYsCUiZttbXsO-I9z-Vk65b9ebXy-WmB2R7OIOW44Z-l7e1XQhYp7GX4dk9Ohu8TnGnkJ7LZis2xHe_3d0twdvz2GWAGZkd6loMf-m0tod5GhDMjum9KLtvyP3iuUESq7VqJhk9KfhvwMAAP__2DW2-w
[https://eotrx.substackcdn.com/open?token=eyJtIjoiPDIwMjUxMjIwMDcyNjEyLjMuZjA3ZDU0ZjZiMGRmYzlkYi5jcGRuMDJncUBtZy1kMC5zdWJzdGFjay5jb20-IiwidSI6NDI2NTE1MDQwLCJyIjoiYkBlbWFpbC5nb21vZHVsci5jb20iLCJkIjoibWctZDAuc3Vic3RhY2suY29tIiwicCI6bnVsbCwidCI6bnVsbCwiYSI6bnVsbCwicyI6MTA4NDUsImMiOiJ1bmZpbmlzaGVkLXN1YnNjcmlwdGlvbiIsImYiOnRydWUsInBvc2l0aW9uIjoiYm90dG9tIiwiaWF0IjoxNzY2MjE1NTcyLCJleHAiOjE3Njg4MDc1NzIsImlzcyI6InB1Yi0wIiwic3ViIjoiZW8ifQ.vtldpTfi_SjPa66O25BooY5VOLnqIP38uCmxO7Tlo94][https://email.mg-d0.substack.com/o/eJx0kEFuwyAQRU8TdrEAA64XnMUaZgYH1UCKoVJuX8WLqpuun_T0_kfovNf28qPEVNL5YLqfI5zY0rOnWgR5N0O0JNirxTmtrF204Azp2HYu3KAzbdD_UGeNePiAyEAEvHKcISqcEXCmEHidV8dRJK-ltkprKRftlJ7mKcqFrIkuSIq4UpjwSUXq_etmZN7vJKd3Wwf8nLBmkc4tNr5afG-DxXOEDWvOo6T-2rhAOJh-0ZEQ3pu2RF7JD2NF8-Fm5CWY9porjaNd5nMEqhlS8QeX8hL933_Gye0tNNpZZaWR4tvrnwAAAP__QdRz2A]
View Email
Welcome to the free edition of Lenny's Newsletter 🥳
lenny@substack.com12/20/2025
Substack