View this post on the web at https://www.lennysnewsletter.com/p/a-visual-guide-to-getting-out-of
š Hey there, Iām Lenny. Each week, I answer reader questions about building product, driving growth, and accelerating your career. For more: Lennyās 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 ]
Iām 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 childrenās 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. Michelleās book is truly great, and makes an excellent giftābut you donāt 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, āCharts for Babies says to your child, āI believe you can understand the worldāāand that message matters from the very start.ā And Booklist [ https://substack.com/redirect/062a87be-68e2-4821-8b5c-11b9fc804599?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] said, āRialās understanding of her audience and her ability to distill information clearly are gifts, and the whimsical hand-drawn illustrations and text will delight readers.ā Grab a copy (or 10) here [ https://substack.com/redirect/79cb8275-c7c0-460e-87f2-65448ca403e4?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ].
š„ Coming soon to Lennyās 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
Lennyās 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, weāre 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 youāre already a paid subscriber, just keep an eye on your inboxāweāll 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 donāt 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 youāre already an Insider, youāll 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 Iām 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 youāre just in a regular creative drought. The paralysis of worrying that your work isnāt worth doing anymore or that someone (or something) is already doing it better.
Well, itās time to lift yourself by your Blundstone loops and climb right out of that rut. Iāve made you a visual pep talk.
Each of the following 12 charts Iām 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 youāll 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 āthirstyā? Or worse, what if Gen Z thinks Iām 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 donāt stop. Maybe they pause or take a rest, but they always come back and keep going. Nobody remembers the project that didnāt 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 itās your never-satisfied immigrant parent? (Just me?) Well, the algorithm will change, and then youāll 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 isnāt. Try not to fall into the trap of squandering your mental alertness on a pile of emails that only needed a simple āsounds good!ā What happens then is we donāt 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 itās 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 Iāve been consistent with it have been my most steady and productive times. Unfortunately, today Iām right here with you, panicking that I need to finish this post.
5. Stop thinking about what youāre 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 attemptāyouād 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 canāt 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, itās popular enough to attract scorn. Maybe nobody sees it? Congrats, itās a hidden gem. Be proud of what youāve 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 doesnāt 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
Donāt discount ideas just because they didnāt 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 whatās still a goner.
And then clean your dining table, for the love of god!! People LIVE HERE.
10. Youāre already further along than you think
If youāre blocked and feeling like youāve been at something forever and still have nothing, go back and look at your draft pile. I bet youāll spot some progress.
11. Itās 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 centerās water aerobics class. Itās never too late (or too early). You might discover youāre great at something you didnāt 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? āLet it be.ā
Did you enjoy this in any small, tiny, pie-chart fraction of a way?
If so, please check out my new childrenās 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 (itās also at places like MoMA Design Store and SFMOMA Museum Store!).
Itās 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 š
If youāre finding this newsletter valuable, share it with a friend, and consider subscribing if you havenāt 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 š
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A visual guide to getting out of a creative slump
lenny@substack.com4/7/2026
View 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 historyāscaling 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 Anthropicās CPO Mike Krieger
How Anthropic is automating growth experiments with Claude (their internal tool called āCASHā)
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 companyās 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 ]āModern 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 ]āAutomate 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 PMāand 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 ]
⢠Anthropicās 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 Komissaroukās website: https://alexeymk.com [ https://substack.com/redirect/03e6bd09-f9bc-45ee-a21d-d3e8273f42f6?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
⢠Alexeyās āMastering Growth Engineeringā 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 Voraās 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. Hereās whatās 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 hasnāt 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 Eganās 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 āThinking in Betsā and āQuit,ā 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 Donāt 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:...
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View Email
Anthropicās $1B to $19B growth run: how Claude became the fastest-growing AI product in history | Amol Avasare
lenny@substack.com4/5/2026
View 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 āprompt injection,ā popularized the terms āAI slopā and āagentic engineering,ā 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 heās made the leap from traditional software engineering to AI-native development more fully and visibly than almost anyoneāand heās 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 āmostly worksā to āactually worksā
How Simon writes 95% of his code from his phone now and why heās 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 ādark factoryā pattern where nobody writes or reviews code and AI does its own QA
Why prompt injection is an unsolved security problem and the ālethal trifectaā 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 ]āModern 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 ]āautomate 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 ]
⢠Thereās a new kind of coding I call āvibe codingā: 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: Nvidiaās 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 ]
⢠Lennyās 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 ]
⢠Simonās tools repository: https://github.com/simonw/tools [ https://substack.com/redirect/a58e4163-7421-486e-aa1e-5fd6b0a03676?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
⢠Simonās 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 doesnāt | 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 ChartāBehind 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.comāYour 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 ]
⢠KÄkÄpÅ: 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 ]
⢠KÄkÄpÅ Cam: Rakiura the kÄkÄpÅā2026 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:...
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An AI state of the union: Weāve passed the inflection point, dark factories are coming, and automation timelines |ā¦
lenny@substack.com4/2/2026
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How to Navigate Org Drama
lenny@substack.com4/1/2026
View this post on the web at https://www.lennysnewsletter.com/p/openclaw-the-complete-guide-to-building
š Hey there, Iām Lenny. Each week, I answer reader questions about building product, driving growth, and accelerating your career. For more: Lennyās 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 ].
āOpenClaw is probably the single most important release of software, probably ever.ā āJensen 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 youāre brand new to OpenClaw or already running one, Claireās 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 Iāve 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 prospectās 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 youāre paying attention to AI news, youāve 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. Youāve also probably seen some horror stories, like when it started deleting this userās 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 ].
Youāre 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, Iām 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 kidsā 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 workāand make my Claws work for me. Hereās 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 Iāve 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 scheduleāeven overnight. Itās 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 āLetās make sure our website always has the latest reasons why weāre better than competitors.ā 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
Itās deployed on an owned machine, like a Mac Mini or a VPS on the cloud that you own and operate yourself
Iāve 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. Letās 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 thatās 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 donāt 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 itās 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 Everyās 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 itās 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 didnāt try going this route, but many technical people prefer it, because itās quick, powerful, and doesnāt 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 donāt actually have to run it on a Mac Mini [ https://substack.com/redirect/c33a5ad5-a227-4e30-a9ca-e7d44fbabc30?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]āyou can use any computer, even an old laptopābut the Mac Mini is simple, powerful, and compact. And itās 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, Iād 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 wonāt need it again after everything is running.
Your pre-work
OK, youāve 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 youāll 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 OpenClawās preferred browser
Installing OpenClaw
Opening the terminal and installing OpenClaw
Open the terminal (Command ā + Space, type āTerminal,ā 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 youāre 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 youāre 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 youāre 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 ātalkā 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 āhatchā in the TUI (Terminal UI). Hello, world!
Setting up Telegram
Youāll 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 canāt 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 youāre 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 agentās 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. Itās fun to look at these files; occasionally, you may need to go in and edit them.
AGENTS.mdāOpenClawās core set of instructions and memory
SOUL.mdāYour agentās persona, tone of voice, and clear boundaries
IDENTITY.mdāYour agentās name, vibe, and personal emoji
TOOLS.mdāNotes on tools and how your agent should use them
USER.mdāAll about you, your OpenClawās 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 kidsā 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. āJust in timeā 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, whoās 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 youāve 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 Iāve found that you shouldnāt 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 youāll 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!
Iām now running a whole team of agents across my life and business. I donāt find it much different than managing a remote team, so Iām able to get a lot of leverage out of my army of Claws. Hereās how they work:
Polly, the personal assistant.
Has access to: email, calendar, Linear
Helps with: scheduling, making sure I donāt 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 donāt 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, kidsā 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 youāre braveāwrite access to everything. Just ask OpenClaw, āHow do I give you read-only access to my Gmail?ā and youāll 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 donāt 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, youāll 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 youāre ready.
Care and feeding
Your OpenClaw will forget things. Its crons will break. Sometimes youāll message āhellooooo?ā into the void.
Just like with my human team, I find myself asking questions like āWhere are we with that project?ā and āDid you forget to email so-and-so?ā OpenClaw isnāt perfect, but it is pretty good at fixing itself.
Some tips:
Youāll sometimes need access to the terminal on your main machine. If youāre 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 āopenā 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 itās forgetting something, ask it to inspect and fix its crons. If itās 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 securityāfor good reason. āWill OpenClaw steal my credit cards, delete my computer, and run away with my spouse?ā 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, itās 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 shouldnāt do anything harmful, but that doesnāt mean it canāt.
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 youāre actually sharing: Your calendar has your physical location. Your email has your financials. Your OpenClaw could know your kidsā 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 isnāt 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: Iām 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. Iāve 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 itās your turn
I started this journey unsure if OpenClaw would be another AI toy Iād abandon after a week. What I got instead was something I didnāt expect: a team that shows up when I need them.
Beyond my own personal productivity, itās the first agentic product Iāve tried that feels like hiring a team. Though Iāve been thinking about the future of agent employees for a while, OpenClaw has made the mechanisms by which weāll āhire,ā 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 isnāt very funny. Crons break, and I say āhellooo?ā into the void more than Iād like to admit.
But hereās the thing about managing a teamāhuman or AI: I donāt need perfection. I need leverage. OpenClaw, when itās working well, gives me more leverage than any agent Iāve tried so far. And that leverage is compounding.
So hereās 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, āBased on what we did today, what can you help me with tomorrow?ā Get creative. Have a little fun. Take a small risk or two.
Youāll start to see what I seeāan 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 āpeopleā that arenāt people.
Now stop reading and go build your team! The world is your lobster. š¦
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, donāt 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 š
Have a fulfilling and productive week š
If youāre finding this newsletter valuable, share it with a friend, and consider subscribing if you havenāt 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 š
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OpenClaw: The complete guide to building, training, and living with your personal AI agent
lenny@substack.com3/31/2026
View 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, āHow I AI,ā 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 (itās easier than you think)
How to avoid the biggest OpenClaw mistakes (donāt install it on your main computer)
Actual use cases that have changed Claireās 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 aboutāand 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 ]āRadically different banking
Omni [ https://substack.com/redirect/015f09c4-57f2-47b6-981e-6877e0d04eab?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]āAI analytics your customers can trust
Orkes [ https://substack.com/redirect/cd5d974c-1b51-4bf2-b453-e21e2575eb10?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]āThe 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 ]
⢠Fryās 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 itās 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 isnāt 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 hasnāt 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 ]
⢠Aliceās 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:...
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From skeptic to true believer: How OpenClaw changed my life | Claire Vo
lenny@substack.com3/29/2026
View this post on the web at https://www.lennysnewsletter.com/p/state-of-the-product-job-market-in-ee9
š Hey there, Iām Lenny. Each week, I answer reader questions about building product, driving growth, and accelerating your career. For more: Lennyās 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 Marketāour fourth and, very surprisingly, the most optimistic. In spite of the headlines about layoffs and AI taking jobs, weāre actually seeing a lot of promising signs in tech hiring, and some interesting new trends:
PM openings are at the highest levels weāve seen in over three years
AI hasnāt 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 doesnāt automatically mean people are finding jobs more quickly. For anyone in that situation, first of all, Iām sorry. Second, Iām working on ways to help. Until then, check out the end of this post for a bunch of resources Iāve collected thatāll improve your odds of landing a gig.
Letās 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 companiesāthe most sought-after and lucrative jobs. (It doesnāt include roles at non-tech companies and consulting agencies.)
1. PM openings are at the highest levels weāve 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 weāve 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 hasnāt 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 donāt 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 youāre skeptical that this growth is real and likely to be sustained, weāre 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 itās likely a leading indication that weāre 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:
āAI rolesā 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, itās 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 donāt know exactly whatās going on here, but it does feel AI-related. Unlike PM and eng, which started growing in 2024 (two years post-ChatGPT), design didnāt. If I had to venture a theory, Iād say that because AI is allowing engineers to move so quickly, thereās less opportunityāand less desireāto 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, youād think design would become a differentiator as more products compete for attention. Something to think about for your company! Weāll keep watching this trend and AIās 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...
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State of the product job market in early 2026
lenny@substack.com3/24/2026
View 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. Sheās spent her career learning how executives actually make decisionsāand 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 donāt get buy-in
Why executive calendars are ālike strobe lightsā 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: āThatās so interesting. What led you to believe that?ā
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 ]āAI analytics your customers can trust
Lovable [ https://substack.com/redirect/3946d30f-9836-4a64-add9-074dd4a0e7fc?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]āBuild apps by simply chatting with AI
Vanta [ https://substack.com/redirect/fd0e94c7-8561-4178-88e6-b32a378e74f8?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]āAutomate 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 Calendlyās 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 Slackās 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 Webflowās 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 Mintoās 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:...
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The art of influence: The single most important skill that AI canāt replace | Jessica Fain (Webflow, ex-Slack)
lenny@substack.com3/22/2026
View this post on the web at https://www.lennysnewsletter.com/p/how-i-built-lennyrpg
š Each week, I answer reader questions about building product, driving growth, and accelerating your career. For more: Lennyās 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, yāall 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 āLearn from Lennyā 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 projectāhow he built it and what he learned.
To let a thousand more flowers bloom, today Iām 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 donāt think anyoneās ever done anything like this before, and Iām excited to give you this excuse to start playing with the latest and greatest AI tools.
Hereās my challenge to you: build something, and let me know about it. Iāll 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 youāve already built something, slurp in this new data and submit it, too. Iāll pick a winner on April 15th. Hereās the data [ https://substack.com/redirect/1ac201be-4635-4524-bf62-615af74b5f6f?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]. Letās go.
Ben is a designer and product builder who enjoys creating small, fun, and thoughtful products that make the world a little better. Heās 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 āagentically engineeredā with Codex and Claude Code š).
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 whoās listened to the podcast for years, I couldnāt 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, youāll 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 Lennyās Podcast guests. However, the more I thought about that idea, the less excited I felt. Interview practice tools by nature feel stressful, and thatās the last type of product I wanted to create. I wanted to make something fun.
What if I turned Lennyās Podcast into a small role-playing game (RPG)? A game where you explore a pixel world, meet guests from Lennyās Podcast, compete with them to test your product knowledge, and even capture them like PokĆ©mon when you win. Thatās how LennyRPG was born.
Hereās 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 isnāt 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 letās walk through how I used this process to build my RPG game. Iāll 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 Lennyās Podcast into a PokĆ©mon-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 PokƩmon 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 Lennyās 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 personās 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 appās 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 youāre at, the PRD makes sure everything the AI generates stays true to what youāre actually trying to build. Thatās 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 Lennyās Podcast, generates questions from each episode, and make it like a PokĆ©mon 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 PokĆ©mon 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 Cursorās 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. Iāve also found it to be great at searching for solutions and open source libraries. Codex is mainly for executing tasks from the implementation plan. Itās 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 Phaserās 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 doesnāt.
This helps a lot for Claude Code and AI in general to understand the codebase and framework better. Itās 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 wasnāt 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 importantlyādid 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 Cursorās 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: āCreate 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}ā
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 Lennyās episode already includes an episode cover that contains the guestās avatar. For this, I triggered Cursorās 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 didnāt know Adam Grenier really has rabbit ears on top of his profile image in the original podcast coverāI almost deleted them. Or there are episodes with two people in the cover image, like Jake Knapp and John Zeratskyās episode, so I had to tell AI to generate a single separate image for each person.
Claude Codeās 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: āSearch for me background music for each phase, with mute control.ā
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. Iāve 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 canāt 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 fileāthings 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 wasnāt even expecting a direct reply given how busy he isābut to my surprise, I got a very kind and encouraging response from him.
That was the nudge I needed to just ship it.
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How I built LennyRPG
lenny@substack.com3/17/2026
View 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 āWhatās the chance thereās a little more here?ā often unlocks a 20% bump
Why Jacob sees 40% average movement when negotiations are run well
When negotiation actually starts (hint: itās much earlier than you think)
Why information + timing create power
The biggest mistakes people make when negotiating
How to navigate the important āWhatās your comp expectation?ā 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 ]āThe enterprise platform for reliable applications and agentic workflows
Mercury [ https://substack.com/redirect/358029cd-fc5f-49b2-b95a-999c17d0871c?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]āRadically different banking
Omni [ https://substack.com/redirect/d59b3550-b96b-427a-8247-40523dfc53d9?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]āAI 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 hasnāt 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 Vossās 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?
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The tactical playbook for getting 20-40% more comp (without sounding greedy) | Jacob Warwick (Executive Negotiator)
lenny@substack.com3/15/2026
View 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 wifeās debut childrenās book, Charts for Babies, coming out next month, we figured: why not do it together? What followed was one of the most honest conversations Iāve had on this podcast. Michelle asked things no one else would think to askāand many things Iāve never shared publicly. Youāll 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 Iāve 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 ]āModern 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 ]āThe AI platform for recruiting
DX [ https://substack.com/redirect/101c911a-3580-4a9d-a82d-e5a7155184f4?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]āThe 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 Lifeās 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
View this post on the web at https://www.lennysnewsletter.com/p/a-guide-to-advanced-b2b-positioning
š Hey there, Iām Lenny. Each week, I answer reader questions about building product, driving growth, and accelerating your career. For more: Lennyās 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 peopleās 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 worldās 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. Sheās also a two-time Lennyās 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 ], āa single shift in positioning can mean the difference between a product that flops and one that breaks through.ā
In her latest guest post, below, April offers a guide to advanced B2B positioningāfour lessons for getting past the trickiest and most common roadblocks that teams run into.
Letās 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 whatās 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 ] (sheāll 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. Iāve 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 positioningāwhich 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, Iām 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 doesnāt know what they are positioning
These roadblocks are common, but theyāre far from impossible to manage. In this post, Iāll 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. Youāll 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 letās 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. Iāve 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 ācompetition.ā
Marketing: Marketing is often overly influenced by a potential competitorās 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 successāeven if the sales team rarely encounters this competitor on a prospectās 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 āhorizon competitors,ā products that arenāt causing any pain today but could in the future. In a positioning exercise, product teams will often list twice as many ācompetitorsā as a sales team does, many of which are never seen on a prospectās 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 āwhaleā 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 ānormalā deals. The second bias is that they rarely define the status quo solution as a ācompetitor.ā Deals lost to the status quo are often categorized as āno decision.ā In the mind of a good salesperson, the customerās āNoā is mentally translated to āNot yet.ā I have seen this even when the overwhelming majority of deals are lost to the status quo.
Founders: Most founders Iāve worked with have a great gut feel for positioning. In fact, many positioning exercises Iāve 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 doesnāt 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, āWe love that. Come back in two years when you have it.ā
The solution: Focus on the prospectās view of the competition
The prospectās 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 wonāt 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 prospectās POV: Rather than have the team list conflicting sets of perceived competitors, ask, āIf we didnāt exist, what would a prospect do?ā 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, āWe have to sell whatās on the truck.ā 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.
Donāt forget the status quo: In B2B, vendors typically lose about half their sales opportunities to whatever the prospect is currently using. Iāve 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 Dixonās JOLT Effect research, for example). Still, we ignore the other half at our peril. Strong positioning wins both types of āno decisionā 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 productsā strengths
Some companies suffer from overly pessimistic product thinkingāwhere teams convince themselves their product is an undifferentiated loser despite clear evidence that theyāre 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 donāt 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 productās ability to deliver differentiated value. Itās hard to convince prospects to invest in a product that sellers donāt 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: Itās 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 marketāand 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 āproblem identificationā 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 (āOh, we have always done that!ā) while sales are selling the heck out of it.
Each symptom reinforces the others, creating a toxic cycle that undermines the companyās ability to articulate and amplify its genuine competitive advantages.
The solution: Keep coming back to whatās working
To break the pattern for positioning work, expose the product team to what sales understands about whatās 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 productās strengths and competitive advantages. We understand the product isnāt 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 productās 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 companyās 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 canāt 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.
Itās 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), itās easy to focus on features and assume buyers will easily understand why those features matter. In my experience, a productās 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 āWhy pick us over the alternatives?ā 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 Iāve worked with have a value point around efficiency. But their buyers may be much more focused on driving revenueāand canāt connect the dots between efficiency and revenue themselves.
Going too far and losing the differentiation completely: In B2B, we really only have two āpureā 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 isnāt going to get you a date or make you look rich. We are increasing revenue or decreasing costs, and thatās it. If you abstract the value of your product all the way down to āThis product saves you money,ā 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 āWhy pick us over the alternatives?ā If we give prospects a list of 10 reasons why, they arenāt likely to connect with a clear story or remember more than a couple of them (if weāre 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 didnāt 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 āso what?ā...
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A guide to advanced B2B positioning
lenny@substack.com3/10/2026
View 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 vehiclesāessentially, 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 shouldnāt do that
The truth about Chinaās 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 Qasarās stint as YCās 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 ]āAI analytics your customers can trust
Vanta [ https://substack.com/redirect/6ef442de-02ed-4d68-bad5-c8bd1a14c0e6?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]āAutomate compliance. Simplify security.
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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 hasnāt 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 Gilās 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 āGood artists copy; great artists stealā: 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 ]
⢠Gandhiās 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 Chinaās 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:...
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The most successful AI company youāve never heard of | Qasar Younis
lenny@substack.com3/8/2026
View this post on the web at https://www.lennysnewsletter.com/cp/189898375
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Three Job Searches, Three AI Roles: What Actually Worked
lenny@substack.com3/4/2026
View this post on the web at https://www.lennysnewsletter.com/p/how-to-debug-a-team-that-isnt-working
š Hey there, Iām Lenny. Each week, I answer reader questions about building product, driving growth, and accelerating your career. For more: Lennyās 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), sheās 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 doesnāt and, more than anyone else Iāve met, is able to translate these lessons into powerful and memorable metaphors.
In her piece below, which I suspect will become as iconic as āGive Away Your Legos [ https://substack.com/redirect/068e63c0-88cc-47fd-8b87-b1b36b5eca48?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ],ā 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.
Letās 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 ].
Thereās a moment most leaders recognize. Youāve set a clear goal (or so you think), your teamās bought in (or so they say), yet timelines keep slipping, execution is messy, and youāre having the same conversations over and over. When that happens, itās tempting to jump straight to people-based explanations: āThis team just doesnāt work well together.ā āThat person isnāt strong enough.ā āWe need better execution.ā
Sometimes thatās 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, Iāve come to believe that blaming people for problems that are actually structural is one of the biggest leadership traps there is.
Iāve 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 isnāt working, things fall apart fast. People get cold, hungry, tired, scared. Thereās no hiding behind process or politeness, and thereās definitely no time for vague diagnoses like āthe vibe is off.ā You have to identify the source of whatās disrupting the teamānot just the symptomsāand fix it quickly.
We learned the Waterline Model as instructors and taught it as part of the curriculum to students. Since then, Iāve 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, Iāll walk through the model and show you how to use it as a practical diagnostic tool when a team is underperforming. Weāll look at the four levels where problems tend to show upāstructure, dynamics, interpersonal, and individualāand how to work through them in the right order. By the end, you should be better equipped to slow down in those āsomethingās offā 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
Hereās the basic picture. Imagine a boat moving across the waterāthat boat is your team. The boatās 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 youāre rowing through a hurricane and no one can quite explain why.
When I use this model, Iām able to move beyond the natural human instinct to automatically blame the people. The Waterline Model helps me investigate one question: Whatās going on below the surface thatās 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 firstāgoals, roles, and decision-makingābefore you start diagnosing personalities.
At the top, just below the surface, is structure. This is the stuff that helps people know what theyāre doing, why theyāre 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 dynamicsāhow 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 doesnāt). 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 interpersonalātension between two people, lack of trust, unresolved conflict, style clashes. These issues are real, but theyāre often caused or amplified by problems higher up.
And at the very bottom is individualāwhatās 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 āsnorkel before you scubaā remind me to start with the issues that impact the most peopleāclosest to the surfaceāand only go deeper once Iāve ruled things out. Before you decide someone is the issue, you need to know that structure and dynamics arenāt pushing them toward exactly the behavior youāre frustrated by.
Letās 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: āGo figure out what this team actually does, and why weāre spending so much money without seeing results.ā
The temptation in a situation like this is to diagnose the peopleāwho is a high performer, who is dragging people downābut 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 teamās 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 Iād 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 teamās 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 teamāsimply 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) theyāre rowing in different directions because the structure isnāt doing its job. Structural clarity alone often resolves more issues than youād expect.
Dynamics: teams behaving rationally inside bad systems
Dynamics are the cultural norms youāve built for how the team actually works together day-to-day. Whatās experienced, not whatās 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: āMy 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 peopleās judgment. It doesnāt feel safe to move quickly.ā
This wasnāt a structure problem. Goals were clear, roles were defined, and, on paper, people had decision rights. But in practice, decisions werenāt 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 didnāt 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 whatās 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 teamās behavior makes sense given the environmentāeven if the results are exactly what you donāt want.
Dynamics problems often show up as process issues, but theyāre 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. Thatās why dynamics issues can feel harder than structural ones. Fixing them doesnāt 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 theyāre enforced through action, not words. Thatās the leverage at the dynamics level: change the rules of interaction, and people will respond.
Interpersonal: donāt assume interpersonal conflict, but donāt ignore it either
When something feels off on a team, leaders almost always leap to this layer firstāāthose two people hate each other.ā To be fair, a lot of the time that instinct isnāt wrong; itās just incomplete.
Very often, what looks like interpersonal conflict is actually being caused by something higher up the waterline. Roles arenāt clear, ownership overlaps, or individual or team incentives are not aligned. Two people are stepping on each otherās toes because the structure put them there. In those cases, the conflict isnāt really about the relationship. Itās 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 donāt trust or like each other. And when thatās true, it always shows up in the business eventually, through slowed decisions, hoarded information, and teams quietly picking sides.
Once youāve 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 isnāt redesigning the system but, rather, addressing the relationship itself. That usually means naming the tension explicitly, grounding the conversation in how itās 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 someoneās roleāsomething you judge their performance on, particularly if itās 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 wonāt 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 youāre likely looking at an actual individual issue. At that point, the work is no longer diagnostic. Itās 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 itās not, change the role or make a clean exit. What doesnāt work is lingering in ambiguity.
Thatās 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 isnāt working well, hereās what the Waterline Model tells you to do: ...
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How to debug a team that isnāt working: the Waterline Model
lenny@substack.com3/3/2026
View 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 ā mock ā 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 ]āRadically different banking
Orkes [ https://substack.com/redirect/00b01a2f-7924-4143-813a-024982da63a6?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]āThe enterprise platform for reliable applications and agentic workflows
Omni [ https://substack.com/redirect/b8521b13-b4c9-46c0-b19d-7dbca938e11a?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]āAI 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 Fridmanās 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 ]
⢠OpenAIās 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 hasnāt 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 ]
⢠Anthropicās 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 Tanaās ālegibility matrixā 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 Zhuoās 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:...
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The design process is dead. Hereās whatās replacing it. | Jenny Wen (head of design at Claude)
lenny@substack.com3/1/2026
View 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 couldnāt have done this job without AI
His āright to winā strategic framework
His communication framework for preventing āpacket lossā across an organization
Why he flips āpraise in public, criticize in privateā 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 ]āCode breaks, fix it faster
Framer [ https://substack.com/redirect/d5c8a2e5-dad9-4043-9c33-5d449a86fbfb?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]āBuild better websites faster
Samsara [ https://substack.com/redirect/d6c1f6af-57f7-48d5-839a-337ee47a1016?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]āSaving 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 hasnāt 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 ]
⢠Anthropicās 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 ]
⢠OpenAIās 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 Kurzweilās 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 ]
⢠Dunbarās 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 Innovatorās 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 Innovatorās 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 AnswersāStraight 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:...
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AI is critical for humanityās survival: Cisco president on the AI revolution | Jeetu Patel
lenny@substack.com2/26/2026
View this post on the web at https://www.lennysnewsletter.com/p/how-to-use-ai-in-your-next-job-interview
š Hey there, Iām Lenny. Each week, I answer reader questions about building product, driving growth, and accelerating your career. For more: Lennyās 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 ]
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One of the most frequent questions Iāve 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 seekersāand the approach Noam took here is quite extraordinary. When he started analyzing what heād learned, he realized the findings didnāt 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 researchāthe successful techniques from over 30 participantsāinto a Claude Codeābased 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).
Letās 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 hadnāt interviewed for a new job in eight years. Heād 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.
Heās 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 didnāt 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 wasnāt 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 Codeābased coach that guides you through how to prepare for job interviews and reach your peak performance.
The Interview Coach Iām offering in this post will give you the critical feedback and real-world reps you need to confidently walk into your next interview roomāand succeed.
But first, letās talk about whatās broken about interview prep today, and how AI solves it.
Interviewing before AI
Interview prep hasnāt 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, weāre left with nothing more than a vague sense of how it went, guessing at what to fix. Companies donāt tell you why they passed. Your friends and mentors donāt know what your interviewers were looking for. Youāre prepping blind, and the post-interview experience is mostly confusing. Thereās 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 whoād been at the same company for 10 years, sent out applications and heard nothing. āI started having creeping impostor syndrome,ā she told me. āAm I actually a good PM? Whatās going on?ā Without feedback, you canāt tell if itās 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 canāt get better at something you only do once every few years. And the common adviceāto interview at companies you donāt care about to get your reps ināis 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 didnāt. Ella built a workflow where sheād 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. Heād simulate the interview beforehand, test which stories landed, and refine them before the real thing.
Some participantsā systems overlapped; some didnāt. 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 canāt or wonāt take on.
The tool youāll find below pulls all that research together into an AI job interview coach that also leverages best-practice coaching techniquesāself-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 canāt analyze a full interview transcript in minutes, track your weak spots across every session, or be there at 11 p.m. when youāre anxious about tomorrow. AI has no such limits, and itās 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 letās 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 didnāt know you had
Coaches you on standing out so you donāt sound like every other candidate who prepped with AI
Helps you strengthen weak stories and retire ones that arenāt 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 concreteānot just āadd more detailā
Tracks your self-assessment accuracy over timeāthe gap between how you think you did and how you actually did
Coaches post-offer salary negotiation with exact scripts and fallback language
Letās get it set up (5 minutes)
Weāll use the Claude desktop app to run our AI interviewing coach.
Hereās 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 ā Download ZIP and unzip, or Git clone if you prefer).
Rename SKILL.md to CLAUDE.md (just right-click ā Rename in your file browser).
Open the Claude desktop app. If youāre already using Claude or Claude Cowork on desktop, youāve probably encountered Claude Code. Select the āCodeā 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 youāll get this:
Letās take it for a spin!
Once youāve run kickoff, everything else works through simple commands. Hereās 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 youāre looking for.
Feedback directness: Tell it how direct you want feedback to be (1-5 scale, default: 5).
Interview timeline: Share where youāre at in the interview process.
Interview history: Share whether youāve been interviewing already, how many interviews youāve done, and how theyāve gone.
Biggest concern: Finally, brain dump whatās stressing you out right now.
At this point, youāre 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 donāt have an interview yet? Type research [company name]. Claude pulls together a quick brief on the companyās culture, interview reputation, and how your background maps to what they typically look for. Itās a lighter version of prep, useful when youāre 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]
Youāll 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 arenāt 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 āInterviewer Intelligenceā 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 interviewerāwhich 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 Lennyās 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 whatās working, what to fix, and which stories to sharpen or retire. If you want, itāll 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 coachās scores. If you consistently rate your structure higher than it actually is, the coach names that pattern. This calibrationāknowing where your blind spots areāis 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 āWhen were you at your best at work? What made it different?ā and āWhatās a decision youād make differently with hindsight?ā 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 canāt 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 āso what?ā pressure (practice pushback), redirect when a question doesnāt match your prep (practice pivot), handle āI donāt have an example for thatā 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 youād rate yourself before sharing your scoresāstrengths first, then gaps, then one specific change for the next round.
Run mock interviews. Type mock behavioral Stripe (or whatever format and company youāre 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. Thereās 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 youāre in product, I highly recommend reading Ben Erezās 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 donāt sound like every other candidate who prepped with AI. It extracts āearned secretsā from your experience (insights you can only claim because you lived them), sharpens your point of view, and helps you retire stories that arenāt 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 missedāeach 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 questionsāeach with why itās 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 youāre noticing before showing you the data: which competencies are improving, where youāre stagnant, and what to drill next. It closes by asking what youāve 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 āreelā (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 scriptsānot 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...
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How to use AI for your next job interview
lenny@substack.com2/24/2026
View 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 Codeās success
Why Boris believes coding is āsolvedā
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 ]āThe developer intelligence platform designed by leading researchers
Sentry [ https://substack.com/redirect/e0284ca3-c44a-48a7-9fcb-dad4ef9eb0f7?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]āCode breaks, fix it faster
Metaview [ https://substack.com/redirect/da16313d-b9b9-4137-abc5-4b79c33f18cd?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]āThe 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 canāt 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 ]
⢠Anthropicās 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 havenāt 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 ]
⢠Lennyās 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:...
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Head of Claude Code: What happens after coding is solved | Boris Cherny
lenny@substack.com2/19/2026
View this post on the web at https://www.lennysnewsletter.com/cp/188400587
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The Promotion Mistakes That Derail PM Careers
lenny@substack.com2/18/2026
View this post on the web at https://www.lennysnewsletter.com/p/how-to-do-ai-analysis-you-can-actually
š Hey there, Iām Lenny. Each week, I answer reader questions about building product, driving growth, and accelerating your career. For more: Lennyās 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 ]
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The problem with AI is that the output always looks confidentāeven when itās full of lies: made-up quotes, false insights, and completely wrong conclusions. As todayās guest author, Caitlin Sullivan [ https://substack.com/redirect/f7942eef-1b93-4120-9316-821976e91981?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ], puts it, āThese mistakes are invisible until a stakeholder asks a question you canāt answer, or a decision falls apart three months later, or you realize the ācustomer evidenceā behind a major investment actually had enormous holes.ā
A user-research veteran, Caitlin has been at the bleeding edge of using AI for user research. Sheās 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. Letās 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 ].
Everyoneās āanalyzingā customer data with AI. But everyoneās also getting answers full of slop: hallucinations, wrong conclusions, and āinsightsā 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 āevidence,ā 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 theyāre side by side, you might spot the problems with the one on the left. But thatās 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 whatās missing. This is exactly why verification matters.
Hereās what separates these answers: the left output cherry-picks three enthusiastic quotes and leaps to a confident recommendation (āYes, build a screenā), without questioning whether those quotes represent the full dataset. It looks persuasive, but itās the AI equivalent of confirmation bias.
The right output does something harder. It challenges the surface-level request (āDo not interpret screen feedback as a single, literal feature requestā), segments users by actual need, and flags pricing risk with specific participant timestamps you can verify. Itās messier and doesnāt oversimplify things, but itās 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 customerās 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, Iāll show you how to get relevant and verified insights you can trust. Youāll learn about four failure modes that silently break your AI-supported insights:
Invented evidence
False or generic insights
āSignalā that doesnāt guide better decisions
Contradictory insights
Iāll 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 youāre 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 whatās 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, theyāre not.
Youād think a CSV would be easy to parse. Rows and columnsāwhatās complicated about that? A lot.
A column of 200 responses to āWhy did you cancel?ā 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 āIt wasnāt for meā 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 columnsātimestamps, internal tagsāsitting right next to customer responses, without clear differentiation. If you donāt tell AI which columns contain the customerās voice and which to ignore, it analyzes everything as signal. Iāve seen AI treat an internal note (āflagged for follow-upā) as something the customer said.
Even āstructuredā columns hide complexity. A header that says āQ3_churn probabilityā 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. Iāve 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.
Hereās 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 arenāt always āprovenāāyou 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 canāt (yet).
ChatGPT: Best for final framing and stakeholder communication. Most creative of the threeāincluding with āverbatim quotes,ā 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. Thereās theme overlap, but ChatGPT misses the userās value/price sensitivity reaction, and all three models give different confidence scores and quotesāsome verbatim, some summarized.
This becomes obvious when we can see all three side by side, but most teams have one LLM enterprise account and wonāt 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 doesnāt filter for you. Youāll often get validated patterns and half-formed hypotheses presented on equal ground, and youāll need to verify that themes are well-evidenced. But thatās a better starting point than having to prompt three times before being sure your analysis partner hasnāt missed something.
A note on examples: For consistency, the examples throughout this post typically use ChatGPT. Itās still the most widely used model among my client teams and students, and itās also the most prone to the specific failure modes Iām 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, Iāve found that there are four distinct failure modes for AI analysisāand 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 isnāt actually their words (particularly common in ChatGPT)
Both types go unnoticed unless youāre 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 āmax. 100 wordsā or āfor each theme, give a punchy and representative quote that captures it (ā¤12 words),ā youāll almost always get mash-ups. Highlights in the example below are combinations like this, not the customerās exact real words.
Why this happens
LLMs donāt retrieve quotes like a search engine; they generate text thatās 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 itās a near-miss, and sometimes itās fabricated.
āVerbatimā 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 ā[P03, 14:30]ā 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 likeāyour quote ārulesāāwhich 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 ārulesā
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 ā 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 āverbatimā 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 āgoodā to them. Youāll likely get much better results right away with my prompt snippet (itās 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]
Hereās 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 youāre digging through 20 interviews and getting just as many patterns back.
Without verification, āquotesā like these end up in your deck attributed to a real participant. Sometimes itās no big deal. Other times, itās the difference between product language that strongly resonates and messaging that doesnāt convert.
This often takes just an extra five minutes, depending on how much data youāre 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: āThe AI analysis just told me what I already knowā or āThese insights are too generic. I canāt do anything with them.ā
They get outputs like:
āPrice is a factor in decisionsā
āPeople value reliabilityā
āUsers want more real-time informationā
True, probably, but useless for tough decisionsāwe need to get deeper than that. These themes could come from so many studies out there. Since Iām working with my fake Whoop data here, they could also easily come from any wearables study.
Themes like these donāt tell you whether your users want this new feature youāre exploring enough to justify the investment, or whether adding it would alienate the customers who chose you specifically because youāre 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 doesnāt support it.
In surveys, that tendency to superficially pattern-match is even worse. When someone writes āItās not for meā when cancelling, AI has to guess what that means. Without guidance, itāll likely lump that response with others into a generic āvalue perceptionā theme. But ānot worth itā could mean:
Too expensive for what Iād get
Too data-intensive and Iām not a serious enough athlete
I donāt want another device to charge
I need a screen and Whoop doesnāt have one
Itās one response with four completely different implications for your product decision. Multiply that ambiguity across hundreds of survey responses, and your āthemesā become meaningless averages that donāt 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 āpricing issues,ā 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 youāre working on. But in many cases, it can be biased cherry-picking from the start.
Hereās an example:
These could describe any wearables study. We canāt make a hardware decision from this.
Another example:
I asked ChatGPT to find me theme clusters and counts for the churn survey question āWhat did you hope to do that Whoop failed to support you with?ā
The results below are clusters that donāt help us make this decision either. So 18% of churned respondents need āmore actionable guidance,ā 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 weāre 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 weāre using AI for analysis, that often focuses on the point of this current customer discovery. Think: objectives, hypotheses, and what part of the product weāre working on.
In the past year, Iāve seen more and more people turn the promptās ācontextā 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. āExploring whether to add a screenā is a specific decision with constraints. āDoing customer researchā is vague, so AI defaults to generic analysis because you gave it no frame.
Business goal tells AI what youāre 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 youāre making.
Product context gives AI domain knowledge. Without it, AI interprets āI want to see my dataā generically. With it, AI understands that statement in the context of a screenless wearable competing against Apple Watchāa completely different interpretation.
Participant overview tells AI whoās speaking. āI need real-time dataā from a churned Garmin switcher means something different than the same words from a loyal user whoās 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 donāt 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):...
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How to do AI analysis you can actually trust
lenny@substack.com2/17/2026
View 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 Sequoiaās 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 āspicyā candidates beats consensus picks
Why enterprise sales will be the last white-collar job AI replaces
Some of my favorite āHalliganismsā
Brought to you by:
Sentry [ https://substack.com/redirect/17ff2aec-fc7c-4197-ba94-d8ec8068890d?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]āCode breaks, fix it faster
Datadog [ https://substack.com/redirect/1fbe94ab-da3c-4ee2-95d5-1b2464ff8994?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]āNow home to Eppo, the leading experimentation and feature flagging platform
WorkOS [ https://substack.com/redirect/9788c9a2-75b9-430e-ab45-b6fa5a3ee8b8?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]āModern 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 Cheskyās 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 āLikeā 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 Lamaās 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 Lütkeās 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 āPigpenā 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 hasnāt 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:...
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Sequoia CEO coach: Why itās never been easier to start a company, and never been harder to scale one | Brian Halliā¦
lenny@substack.com2/15/2026
View this post on the web at https://www.lennysnewsletter.com/p/engineers-are-becoming-sorcerers
Sherwin Wu leads engineering for OpenAIās 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 āmodels will eat your scaffolding for breakfastā
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 ]āThe developer intelligence platform designed by leading researchers
Sentry [ https://substack.com/redirect/da9962af-8919-4a48-a291-fb736d2be551?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]āCode breaks, fix it faster
Datadog [ https://substack.com/redirect/143cc80e-0ce1-464e-b07a-7462c4d90f13?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]āNow 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 ]
⢠OpenAIās 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: āI ship code I donāt readā: 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 Sorcererās 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 hasnāt 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 Bustamanteās āLLMs Eat Scaffolding for Breakfastā 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: Chinaās 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 Worldās 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:...
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āEngineers are becoming sorcerersā | The future of software development with OpenAIās Sherwin Wu
lenny@substack.com2/12/2026
View this post on the web at https://www.lennysnewsletter.com/p/building-ai-product-sense-part-2
š Hey there, Iām Lenny. Each week, I answer reader questions about building product, driving growth, and accelerating your career. For more: Lennyās 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 ].
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In part two of our in-depth series on building AI product sense (donāt 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 ]āa longtime AI PM at Google and Meta, and an OG AI educatorāshares a simple weekly ritual that you can implement today that will rapidly build your AI product sense. Letās 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. Itās called āProduct Sense with AI,ā and candidates are asked to work through a product problem with the help of AI, in real time.
In this interview, candidates arenāt 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 senseāunderstanding what a model can do and where it fails, and working within those constraints to build a product that people loveāis becoming the new core skill of product management.
Over the past year, Iāve 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, āIs this good?ā) 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. Itās not a theory or a framework but, rather, important practice that gives you early feedback on model behavior, failure modes, and tradeoffsāforcing 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 Iāve already experienced the weird cases myself. And I get clarity on whatās a product problem vs. whatās a model limitation.
In this post, Iāll 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. Itās about understanding and predicting how the system will respond to different circumstances.
In other words, the work expands from āIs this a good product idea?ā to āHow will this product behave in the real world?ā
Letās 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 Iām 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 modelās tendency to force structure onto chaos
Take the kind of chaotic, half-formed, emotionally inconsistent data every PM deals with dailyāthink Slack threads, meeting notes, Jira commentsāand ask the model to extract āstrategic decisionsā from it. Thatās because this is where generative models reveal their most dangerous pattern:
When confronted with mess, they confidently invent structure.
Hereās an example messy Slack thread:
Alice: āStripe failing for EU users again?ā
Ben: āno idea, might be webhook?ā
Sara: ālol can we not rename the onboarding modal again?ā
Kyle: āStill havenāt figured out what to do with dark modeā
Alice: āWe need onboarding out by Thursdayā
Ben: āWait, is the banner still broken on mobile???ā
Sara: āI can fix the copy laterā
I asked the model to extract āstrategic product decisionsā 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 itās completely wrong.
Now that you have the obviously wrong results, youāll need to generate the āidealā response and compare the two responses to understand what signals the model needs to behave correctly.
Hereās 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.
Letās say the model invents features you never discussed. Great, youāve 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 āNot enough information.ā
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 (ākey themesā). It avoids assigning owners unless explicitly stated and highlights uncertainties instead of hiding them.
3. Compare the two outputsāand the inputs that led to themāside by side
This contrast of the two outputs aboveāconfident hallucination vs. humble clarityāis 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.
Youāre 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 āgoodā version feel shippable or still brittle?
What would the user experience in each version?
4. Capture the gapsāthis 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, Iāll 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 modelās semantic fragility
Ambiguity is kryptonite for probabilistic systems because if a model doesnāt fully understand the userās intent, it fills the gaps with its best guess (i.e. hallucinations, bad ideas). Thatās 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 āSummarize this PRD for the VP of Product.ā
How to try this in 2 minutes (NotebookLM):
Open NotebookLM ā create a new notebook
Upload a PRD (Google Doc/PDF works well)
Ask: āSummarize this for execs and list the top 5 risks and open questions.ā
Does it:
over-summarize?
latch onto one irrelevant detail?
ignore caveats?
assume the wrong audience?
The modelās failures reveal where its semantic fragility isāin 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 youāre 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 (āSummarize for who?ā), giving the model more context, or constraining the action so the model canāt go off-track. Youāre not trying to ātrickā the model; youāre 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 modelās first point of failure
Pick one task that feels simple to a human PM but stresses a modelās reasoning, context, or judgment.
Youāre not trying to exhaustively test the model. Youāre 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 isnāt the final solution yet; itās the intended behavior. In the guardrails section later, Iāll show how to turn this into an explicit rule in the product (prompt + UX + fallback behavior).
Example 1: āGroup these 40 bugs into themes and propose a roadmap.ā
Example 2: āSummarize this PRD and flag risks for leadership.ā
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 effectsāmoments 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 modelās failure modes and have designed around them, itās nearly impossible to entirely predict how AI features will behave once they hit the real world, but performance almost always drops once theyāre out of the controlled development environment. Since you donāt 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 itās 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 productās 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 āgreatā model felt broken. And from the userās 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 (āIām not sure whoās speakingāshould I use your profile or continue as a guest?ā)
Delight bar
You donāt need a perfect percentage to know that youāve hit the right delight bar, but you look for behavioral signals like:
Users stop repeating themselves or rephrasing commands
āNo, I meant . . .ā 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 youāre 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, āSorry, can you repeat that?ā
6 p.m. kitchen test: Dishwasher running, kids talking, dog barkingāand the smart speaker still recognizes you and gives a personalized response without a āI couldnāt recognize your voiceā interruption.
Mid-command correction test: You say āSet a timer for 10 minutes . . . actually, make it 5,ā 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 didnāt actually assign values to each bar. Thatās because the specific thresholds for MVQ (your āacceptable,ā ādelight,ā and ādo-not-shipā bars) arenāt 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 itās financially viable. Thatās why itās important to estimate the AI product or featureās cost envelope early.
Cost envelope = the rough range of what this feature will cost to run at scale for your users
You donāt need perfect numbers, but you need a ballpark. Start with:
Whatās the model cost per call (roughly)?
How often will users trigger it per day/month?
Whatās the worst-case scenario (power users, edge cases)?
Can caching, smaller models, or distillation bring this down?
If usage 10xās, 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 ā ~$0.40/month/user
Heavy users: 100 meetings/month ā ~$2.00/month/user
With caching and a smaller model for ālow-stakesā meetings, maybe you bring this to ~$0.25ā$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 youāre proposing actually make sense for the business?
Design guardrails where behavior breaks
Now that you better understand where a modelās behavior breaks and what youāre looking for to greenlight a launch, itās 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 donāt get confused, misled, or lose trust. In practice, guardrails protect users from experiencing a modelās failure modes. At a startup Iāve been collaborating with, we built an AI feature to increase the teamās productivity that summarized long Slack threads into ādecisions and action items.ā In testing, it worked wellāuntil 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...
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Building AI product sense, part 2
lenny@substack.com2/10/2026
View 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 āgenie and three wishesā mental model for making the most of AIās limitations
How product, engineering, and design roles are convergingāand what that means for your career
Brought to you by:
Strella [ https://substack.com/redirect/c42f2f1e-d02e-4257-8a32-5e7d19efb796?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]āThe AI-powered customer research platform
Samsara [ https://substack.com/redirect/92e1f1e0-a9dc-4479-8340-4954a163e254?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]āSaving lives with AI built for physical operations
WorkOS [ https://substack.com/redirect/cb0b31cd-1c26-4a2f-b3ef-14db80696a7a?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]āModern 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 ]
⢠Everyoneās an engineer now: Inside v0ās 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 Haasās 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 canāt 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 āworseā 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 Googleās 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:...
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Getting paid to vibe code: Inside the new AI-era job | Lazar Jovanovic (Professional Vibe Coder)
lenny@substack.com2/8/2026
View this post on the web at https://www.lennysnewsletter.com/p/how-to-build-ai-product-sense
š Hey there, Iām Lenny. Each week, I answer reader questions about building product, driving growth, and accelerating your career. For more: Lennyās 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 ] | Lennyās 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 youāre about to read took over 100 hours to create. Thatās because itās not a post. Itās 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 youāll find below, and even partnered with Cursor to get you free credits (see below!) so that you can try this at home. Iāve never seen anything like what theyāve put together, and Iām excited to bring it to you.
Next week, in part two of this series, youāll 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 ].
Youāre in a product meeting and someone mentions āsubagentsā or ācontext engineeringā or āagent memory.ā You nod along. You know what these terms mean . . . youāre just hoping no one expects you to use them in a sentence.
Youāve 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 youāre 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 isnāt you. The problem is the āAI hype industrial complex.ā Most AI content is designed to induce FOMO, not to teach: āThis model is INSANEā 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 āAI product senseāāthe 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 āforgettingā facts and recognizing it as context rot. Or watching a user struggle through a workflow and confidently saying that agent memory solves thisāand knowing how to restructure the experience.
Weāve 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 AIās 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, weāll guide you through using AI coding agents for your non-technical product work:
In steps 1-4 weāll get set up and familiar with Cursor with a fun Disney-themed exercise
In steps 5-6 weāll use Cursor to get hands-on with choosing AI models and calling tools
In steps 7-10, weāll 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
Youāll walk away with the confidence to anticipate the technology instead of chasing it and, as a bonus, a personal AI operating system. Together weāll 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.
Youāre 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 āOpen project.ā
If youāve already used Cursor before, click File > New Window to get to this screen and open a new project.
Click āNew Folderā:
Name it āBuild AI Product Senseā and click āCreateā:
And finally, click āOpenā (yes, itās unusual to click Open on an empty folder, but just do it, itāll work):
Step 3: Continue this post inside Cursor
Strap in, because youāre going to continue the experience inside Cursor itself, inspired by the childrenās science show The Magic School Bus [ https://substack.com/redirect/8f17a914-e46f-4a22-ab4d-4a2d9e724a23?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ].
If you donāt 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 youāre in āAgentā mode. This allows Cursor to take actions (such as fetching this post from the internet).
In the āmodelā dropdown, turn off āautoā and select Opus 4.5 š§ :
š Side note: Weāre hooking you up with free Cursor credits š
To help you experience the full power of this tutorial, weāre hooking up Lennyās 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) Lennyās 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 youāll see the screen below:
4. Click āGet Startedā to apply the credits to your account. [Credits can be redeemed with both free and paid accounts.]
5. Once youāve redeemed the credits, you should see this box appear in your Cursor dashboard. [If you donāt see the credits, try to hard-refresh, or log out and log back in. If that doesnāt work, shoot a message to hi@cursor.com [ mailto:hi@cursor.com ] and mention this post.]
6. Finally, youāll need to upgrade to the Pro (or higher) plan to use the latest AI models, like Opus 4.5. If youāre already on the Pro or higher plan, youāre all set.
Once you see the credits in your Dashboard, go ahead and upgrade. You wonāt be charged anything (you have 2.5 monthsā worth of credits). The credits will be automatically applied to the next invoice (and can also be applied to āon-demand usage [ https://substack.com/redirect/9e7e74aa-5d69-4c20-9972-8cc519e5b0bd?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]ā 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 ā that will be distracting ā use cURL or any other tool.)
Start by giving me an overview of why weāre here and where weāre going with this, so I feel super-motivated to stick with it. Then pause and confirm Iām 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 āStep 3.ā
You are both a really good 1-1 tutor for hands-on learning AND the Cursor agent. Have me take action so Iām 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 ā and hold me to a high bar ā like an effective, empathetic tutor.
Itās 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 weāve 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 letās 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 āchange this file,ā act on it yourself (donāt direct me to do it separately or ask if I did it separately). Donāt refer to a separate Cursor agent. Itās 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, itās going to ask for my approval, and thatās going to feel scary. So I need you to explain why youāre asking and why itās safe to approve. It might even be a teachable moment ā you can tie to the goal of the post (and where we are in the journey) that, well, youāre an agent and this is you in action!
Consistently encourage me to use the voice recording feature (a šļø icon under the chat box) to build the habit of speech-to-text.
And click āsubmitā:
If you choose to accept this challenge, youāll consume the rest of this post from inside Cursor. Stay in one chat thread (āagentā) the entire time (no need to open a new thread or agent).
AI will walk you through the rest of this post. Seatbelts, everyone! Weāll see you in Cursor.
Step 3: Cursor may look intimidating, but youāre more familiar with it than you realize
Cursor looks Matrix-style geeky, but itās just ChatGPT, a text editor, and a file explorer smooshed into one window.
We repeat, Cursor is just three tools youāve used plenty of times before, combined:
ChatGPT
A text editor
File explorer
One of Talās students, a salesperson, said it best: Cursor is āAI that can touch any file on my computer.ā
Hereās a quick tour:
1. Agents
Agents are a fancy term for āchats.ā This is where youāll interact with AI.
On the left, youāll see an empty panel that will contain your agent history. Click ānew agentā to start your first chat (āagentā is synonymous with āchat threadā):
Youāll see a familiar chat box. Click on the dropdown in the bottom left corner. You can select between āAskā mode and āAgentā mode (ignore the other options, like Plan and Debug, for now).
āAskā 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.
āAgentā mode is for when we want Cursor to modify files in our project. Weāll use this together in a moment.
2. Editor
Weāll 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 youāve 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 youāve already created your AI thinking partner [ https://substack.com/redirect/fcb4999a-a570-4008-a655-d77cd89ae6a1?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] inside ChatGPT or Claude projects, youāre probably wondering if itās worth the hassle of switching to Cursor. Itās 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 whatās 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 youāre 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
Weāll start by creating a new blank file in Cursor. Hover your mouse in the file explorer, and click the āNew Fileā 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 āAgentā 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 āup arrowā button:
A lot just changed on our screen! Youāll 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 āUndoā if you donāt like the change, or āKeepā if you want it to remain.
Step 5: See how different AI models behave
Now that youāve made your first edit, letās explore a key product decision every AI team faces: which model to use.
Youāll notice thereās another dropdown in our chat box:
Youāve seen this in ChatGPT, Claude, or Geminiāitās where you choose the model you want to use. In Cursor, however, you can choose any LLM.
Click into it and disable āAuto,ā 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 ā...to make fun of the song itself,ā which qualifies as āfair useā). While OpenAIās models are less concerned with copyright, they stumbled when calling Cursorās 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 itās 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, thereās a subtle lesson in Cursorās model dropdown: There are only a few frontier LLMs, and theyāre available to all product teams. Innovation is how we apply them.
Make a habit of switching models for tasks you care about. Over time, youāll develop genuine opinions about model tradeoffsāthe kind of intuition thatās hard to get from benchmarks alone.
Step 6: Inspect your agentās tool calls
LLMs can only produce text, but when they take action (edit a file, fetch data, search the web), theyāre 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
Hereās how it described #3:
Donāt let this toolās foreign name repel you. Youāve done āsearch and replaceā plenty of times in Microsoft Word or Google Docs. And youāve definitely āread a fileā 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; youāve 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 canāt 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 canāt hold the hammer. Cursor is the handyman: it hears the LLMās 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 youāve heard the terms āMCP clientā or āagent harness,ā those both describe Cursorās role here.)
The way an LLM interacts with tools is eerily similar to how it interacts with humans. If we view āclassic ChatGPTā 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, āCan our agent do X?ā youāll instinctively think, āWhat tools would it need, and how good is our model at calling them?ā This also connects back to model selection: itās not just āsmartest model wins.ā 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 whatās the āMCPā I keep hearing about?
For most organizations, the most valuable data doesnāt 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, thatās the right analogy. To continue the comparison: most agent tools arenāt MCP, just like most electrical wires arenāt 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, letās create a personalized AI agent for ourselves to see how the components of Cursor come together.
Weāre 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. Weāll be free to focus on whatās technically possible.)
By the end of this exercise, youāll 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, weāll 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 youāre on āAgentā mode):...
Unsubscribe https://substack.com/redirect/2/eyJlIjoiaHR0cHM6Ly93d3cubGVubnlzbmV3c2xldHRlci5jb20vYWN0aW9uL2Rpc2FibGVfZW1haWw_dG9rZW49ZXlKMWMyVnlYMmxrSWpvME1qWTFNVFV3TkRBc0luQnZjM1JmYVdRaU9qRTROakl5TmpJMU1pd2lhV0YwSWpveE56Y3dNVEkzTWpFNExDSmxlSEFpT2pFNE1ERTJOak15TVRnc0ltbHpjeUk2SW5CMVlpMHhNRGcwTlNJc0luTjFZaUk2SW1ScGMyRmliR1ZmWlcxaGFXd2lmUS5RdzRObWd2Q0JnVm5ETXdrLXAyWFdtaUlXMnR1RUNaMVJ5amNvR2J0cFJRIiwicCI6MTg2MjI2MjUyLCJzIjoxMDg0NSwiZiI6dHJ1ZSwidSI6NDI2NTE1MDQwLCJpYXQiOjE3NzAxMjcyMTgsImV4cCI6MjA4NTcwMzIxOCwiaXNzIjoicHViLTAiLCJzdWIiOiJsaW5rLXJlZGlyZWN0In0.UDHtDYpDDKJVdB2DX798Ubb46KxoFIcZGz2HPBGD9Zk?
View Email
How to build AI product sense
lenny@substack.com2/3/2026
View 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 systemsāwhether families or companiesāoperate 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 repairānot perfectionādefines strong leadership
Why you need to connect before you correct to build cooperation and trust
The āmost generous interpretationā framework for handling difficult behaviors
How to correctly set boundaries (vs. making requests)
The power of āI believe you, and I believe in youā
What it looks like to be a āsturdyā leader
Brought to you by:
Merge [ https://substack.com/redirect/43b9581f-e213-43f4-95f2-83582f7eded7?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]āFast, secure integrations for your products and agents
Metaview [ https://substack.com/redirect/b8211cef-fa7a-4bc9-9283-bf49c7d58040?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]āThe AI platform for recruiting
Framer [ https://substack.com/redirect/baae352c-4b9c-4da7-8c24-c878afdd7e82?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]āBuilder 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 worldās 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:...
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Dr. Becky on the surprising overlap between great parenting and great leadership
lenny@substack.com2/1/2026
View 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 weāre 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
Whatās actually going to happen with AI and jobs (spoiler: he thinks the panic is ātotally off baseā)
The āMexican standoffā thatās happening between product managers, designers, and engineers
Why you should still learn to code (even with AI)
How to develop an āE-shapedā career that combines multiple skills, with AI as a force multiplier
The career advice he keeps coming back to (āDonāt be fungibleā)
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 ]āThe developer intelligence platform designed by leading researchers
Brex [ https://substack.com/redirect/afa89738-d065-4902-89c9-802d0ebc6d0e?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]āThe banking solution for startups
Datadog [ https://substack.com/redirect/96d28e99-ff78-43fc-80c2-a3c9f35aa837?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]āNow 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 Horowitzās website: https://a16z.com [ https://substack.com/redirect/e22b9f15-d146-47da-a00d-b6c21b570b0e?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
⢠Andreessen Horowitzās 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 philosopherās 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 ]
⢠Bloomās 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 Summersās 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 Googleās 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:...
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Marc Andreessen: The real AI boom hasnāt even started yet
lenny@substack.com1/29/2026
View this post on the web at https://www.lennysnewsletter.com/p/product-pass-drop-canva-elevenlabs
š Hey there, Iām Lenny. Each week, I answer reader questions about building product, driving growth, and accelerating your career. For more: Lennyās 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 ] | Lennyās 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 ]
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ā 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 Iāve said before, thereās 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 youāre in that first group.
Your paid subscription gets you access to the worldās 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 builderāfor 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 Iām holding off on, to get you the highest concentration of goodness. Every quarter (or so), weāll continue rotating products in and out so that we can keep this collection fresh and awesome.
Many readers expense this subscription out of their workplaceās learning and development budget. Hereās 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 newsletterāyou wonāt 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, hereās what you get starting today:
1. Manus [ https://substack.com/redirect/56d0d270-fc18-4c5c-bf46-13e4fe479ad2?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]ā1 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 competitorās 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 ]ā1 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 visualizationsāacross React, Tailwind, and PostgreSQLāin 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 browserāsign-in, forms, checkoutātakes 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 ]ā1 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 softwareābackend 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 ]ā1 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 ]ā1 year free of Framer Pro ($360 value)
Framer is a design-first website builder that lets you build, ship, and manage your companyās 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 ]ā1 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 youāre 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 ]ā1 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 Iām already a paid subscriber, do I get access to the products?
Yep! The same rules below apply to both new and existing subscribers.
Whatās the difference between the Annual and Insider tiers?
Since we donāt 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 productsāwe 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 theyāre gone, theyāre 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 accessāmeaning youāll get front-of-the-line access to every product, and we set aside a dedicated pool of codes for this tier. In practice, youāll 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 werenāt able to give us enough codes to cover every single Insider indefinitely, and weād 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 youāve already paid for one of the products before (monthly or yearly) or redeemed one of our offer codes for that product, you wonāt 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 wonāt 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 canāt wait to hear about what you build with these products.
Enjoy!
If youāre finding this newsletter valuable, share it with a friend, and consider subscribing if you havenāt 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 š
Unsubscribe https://substack.com/redirect/2/eyJlIjoiaHR0cHM6Ly93d3cubGVubnlzbmV3c2xldHRlci5jb20vYWN0aW9uL2Rpc2FibGVfZW1haWw_dG9rZW49ZXlKMWMyVnlYMmxrSWpvME1qWTFNVFV3TkRBc0luQnZjM1JmYVdRaU9qRTRORFE1Tmprd05Td2lhV0YwSWpveE56WTVOVE16TVRNd0xDSmxlSEFpT2pFNE1ERXdOamt4TXpBc0ltbHpjeUk2SW5CMVlpMHhNRGcwTlNJc0luTjFZaUk2SW1ScGMyRmliR1ZmWlcxaGFXd2lmUS5KSUFRVW5NdlhxaHZrVVgySkgxT2VCcm12TWdYamtLQWVEN1hnWk9aekZFIiwicCI6MTg0NDk2OTA1LCJzIjoxMDg0NSwiZiI6dHJ1ZSwidSI6NDI2NTE1MDQwLCJpYXQiOjE3Njk1MzMxMzAsImV4cCI6MjA4NTEwOTEzMCwiaXNzIjoicHViLTAiLCJzdWIiOiJsaW5rLXJlZGlyZWN0In0.ZoCfxLnPnXSZbWzQKZ8j_gpwoCc1qFKC4_t0KCKoIaQ?
View Email
Product Pass drop: Canva, ElevenLabs, Manus, Factory, Amp, Railway, Framerānow free with your paid subscription
lenny@substack.com1/27/2026
View 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 growthāa 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:
Jasonās five-step framework: logo retention, pricing, NRR, marketing channels, target market
A small tweak thatāll double response rates on your cancellation surveys
Why āitās too expensiveā is almost never the real reason customers cancel
The āelephant curveā 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 ]āVibe coding platform as an API
Strella [ https://substack.com/redirect/e1beff84-6487-4781-89c6-d92d893f05eb?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]āThe AI-powered customer research platform
Brex [ https://substack.com/redirect/2eeeab06-32ff-423f-b9c7-6132a88d71b5?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]āThe banking solution for startups
Where to find Jason Cohen:
⢠Preorder Jasonās 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 Cowenās 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 Campbellās 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 ]
⢠āSell the alpha, not the featureā: 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: Hereās 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:...
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Why your product stopped growing (and the 5-step framework to restart it) | Jason Cohen
lenny@substack.com1/25/2026
View this post on the web at https://www.lennysnewsletter.com/p/chatgpt-apps-are-about-to-be-the
š Hey there, Iām 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 ] | Lennyās 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 ] | Lennyās 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 collaboratorāand author of my 2nd and 12th most popular posts of all timeāis back, and itās a banger. If youāre looking for alpha in growing your product, this post is for you. Iāll 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, youād get a helpful list of recommendations: airline breakdowns, price ranges, maybe some tips on timing. Then youād leave ChatGPT, open a travel site, and start your search from scratch.
Now you can say, āHelp me find a good flight to Paris from Toronto,ā 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 ChatGPTās 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 Shopifyās 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, Iāll 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. Letās 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 donāt fully grasp), ChatGPT will automatically suggest apps based on a userās 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 doesnāt 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 itās important for you to consider which format would match the type of app experience you want to create for the user. Iāll 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 ChatGPTās responses. Hereās 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.
Thereās one important constraint to understand: one widget per message. If the user says, āBook a restaurant and order an Uber,ā 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 youāre preparing to build a ChatGPT app, itās important to first understand the architecture.
Every ChatGPT app has three parts:
The conversation within ChatGPT: The model interprets the userās request and decides whether an app would be helpful.
The appās ātoolsā: A backend server and API tells ChatGPT what the app can do.
The user-facing widget: This appears in the userās chat, built with web technologies (typically React) and runs in a secure sandbox inside ChatGPT.
Letās dig into #2, the appās tools, because thatās 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.
Hereās the flow: The user says, āFind me Italian restaurants in Brooklyn.ā ChatGPT looks at the available tools, sees one called search_restaurants with a description like āSearch for restaurants by location and cuisineā and calls it with {location: āBrooklynā, cuisine: āItalianā}. 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 widgetāsay, 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, āUser selected restaurant_id: 1241,ā 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 ā ChatGPT calls a tool ā widget renders ā user interacts with widget ā 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 theyāre 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 youāve 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 whoās running the show. When you build your own AI agent, you control everythingāthe 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 toolās 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. Iād 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 ]. Iād highly recommend using my project; it will likely save you at least 30 minutes.
If youād prefer to start from scratch, head to Replit, select āImport from GitHub,ā 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 projectāit 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 youāll only be able to see the UI components once youāre connected to ChatGPT. Allow Replit to continue working until it has set up the MCP server correctly.
Eventually the Replit agent should tell you itās 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:
Weāre now ready to connect to ChatGPT. Ask the agent, āWhat is the external MCP URL for this app?ā 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 arenāt built to help you understand MCP and ChatGPT apps. Theyāre great at building web apps, but they canāt create an MCP server, preview your tools, or help you connect to ChatGPT.
Thatās why I decided to build one myselfāChippy [ 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, Iāll 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, Iāll 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 āTestā 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, youāve 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 donāt have to be as simple as showing a video or displaying a card. You can build full, complex applications directly into ChatGPT. Hereās 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...
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ChatGPT apps are about to be the next big distribution channel: Hereās how to build one
lenny@substack.com1/20/2026
View 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
Zeviās āpeer reviewā technique, which uses different AI models to review each otherās 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 ]āVibe coding platform as an API
DX [ https://substack.com/redirect/09bd6314-93a2-4458-9544-f0189c290189?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]āThe developer intelligence platform designed by leading researchers
Framer [ https://substack.com/redirect/e8a40801-70cc-4b11-965f-92ce8ed4cd7c?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]āBuild 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 monthsāone 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 canāt 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 ]
⢠Linearās 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 ]
⢠Everyoneās an engineer now: Inside v0ās 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:...
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The non-technical PMās guide to building with Cursor | Zevi Arnovitz (Meta)
lenny@substack.com1/18/2026
View 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 whoās now teaching etiquette to Silicon Valleyās founders. In this unconventional episode, Sam explains why proper etiquette has become a vital skill for founders in 2026āespecially 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 āshow up in a room with a low heart rateā 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
Samās 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 ]āVibe-coding platform as an API
DX [ https://substack.com/redirect/5fbff447-baf1-4624-8590-c4633379924c?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]āThe developer intelligence platform designed by leading researchers
WorkOS [ https://substack.com/redirect/49b4956c-2489-4808-b044-df87f29a31de?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]āModern 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 ]
⢠āLose Yourselfā 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 canāt 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 ]
⢠Manās 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 Americaās 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 Americaās 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:...
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How to show up in any room with a low heart rate: Silicon Valleyās missing etiquette playbook | Sam Lessin
lenny@substack.com1/15/2026
View 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, theyāve 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 arenāt 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 ]āThe fastest way to ship 220+ integrations
Strella [ https://substack.com/redirect/bcd6d313-94fa-4739-a3ed-8f92b4b33a21?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]āThe AI-powered customer research platform
Brex [ https://substack.com/redirect/4fec3922-0353-4617-b3c8-647089588b86?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]āThe banking solution for startups
Get 15% off Aishwarya and Kiritiās 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 Zahariaās lab): https://arxiv.org/pdf/2512.04123 [ https://substack.com/redirect/816a944f-a65c-410f-bf22-932ac28c40e5?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]
⢠Matei Zahariaās 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 AIās biggest bottleneck (and whatās 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 adviceāwhat 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 agentsāhereās 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 ]
⢠Socratesās 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 Smithās 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 Jobsās 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:
⢠āWhen 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:...
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What OpenAI and Google engineers learned deploying 50+ AI products in production
lenny@substack.com1/11/2026
View this post on the web at https://www.lennysnewsletter.com/p/best-of-lennys-newsletter-2026
š Hey there, Iām Lenny. Each week, I answer reader questions about building product, driving growth, and accelerating your career. For more: Lennyās 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 ] | Lennyās 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 Mannās words [ https://substack.com/redirect/7cd1b849-acf8-4ca5-bfff-7ff884a44c56?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] continue to ring in my ears: āThis is as normal as itās going to be. Itās going to be much weirder very soon.ā
In the swirl of so much change, thereās a growing divide between the people who understand where things are going and will benefit from it, and those who donāt and will have an increasingly hard time. More and more, I see my mission as making sure youāre 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, itās 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 youāve still got 50 tabs open with posts youāve been planning to read, close them all and check out the stuff below.
As always, Iād 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, hereās 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 ā
ā 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 Iām in the process of exploring the next addition.
Lenny and Friends Summit 2.0 š” ā Stay tuned for some news on this š
Making the paid subscription an absolute no-brainer by adding more killer perks ā
ā 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 weāve got coming this year.
Launching a product ā ā I decided it wasnāt the right year for this.
Above all else, continuing to deliver a high-quality newsletter and podcast every week ā
ā 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 ššš
Carefully balance content cadence between AI and non-AI, IC vs. manager vs. VPs, and product management vs. adjacent skills
Here we go.
š£ Quick heads-up: Weāre refreshing our Product Pass [ https://substack.com/redirect/28e50f4c-323d-44f6-a227-ed4068d76b19?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ] partner lineup at the end of January
Weāve 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 youāve 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 youāre at the Annual tier itāll only be there if you grabbed it already.)
While youāre there, check out the other products too. Supplies are limited and deals do expire, so donāt 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 ]āThe 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 ]āHow 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 ]āReal-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 ]āPractical 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 ]āHow 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 ]āA 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 ]āHow to thrive in āthe great flatteningā 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 ]āThereās 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 ]āA 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 ]āThe step-by-step guide thatās helped hundreds of leaders secure life-changing compensation
The Magic Loop [ https://substack.com/redirect/4273aa67-3cc8-4bf3-8d06-15f37231fcf9?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]āA framework for rapid career growth
Best on health
Why youāre so angry at work (and what to do about it) [ https://substack.com/redirect/c2163a31-f283-4a40-b520-7d3c10d6c6bf?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]āA 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 ]āHow the Internal Family Systems model can help you listen to your inner wisdom and get unstuck
How techās most resilient workers handle burnout [ https://substack.com/redirect/3e07c322-997a-4f34-be8e-4cf0c0973a6e?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]āIntroducing ARMOR: a new framework building on our tech worker sentiment survey insights
A builderās guide to living a long and healthy life, with Justin Mares [ https://substack.com/redirect/c3fa4291-5f33-4c99-ad25-d3130e105afc?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]āFor something a little different
Best on strategy...
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Best of Lennyās Newsletter 2026
lenny@substack.com1/6/2026
View this post on the web at https://www.lennysnewsletter.com/p/the-high-growth-handbook-molly-graham
Molly Graham has worked for some of techās 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. Sheās best known for her āGive away your Legosā 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:
āGive away your Legosā: a framework for scaling yourself as a leader
āJ-curves vs. stairsā: the two paths of career growth, and why you should pick the scarier path
āThe waterline modelā for diagnosing team problems (and why you should āsnorkel before you scubaā)
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 ]āThe developer intelligence platform designed by leading researchers
Brex [ https://substack.com/redirect/20e0c48a-856b-41ab-bb8e-51d14636de29?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]āThe banking solution for startups
GoFundMe Giving Funds [ https://substack.com/redirect/72c0052a-ae60-497a-b144-b2efc743b2bb?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]āMake 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 āLikeā 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 ]
⢠āGive Away Your Legosā 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 ladderāwinners 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 Campbellās 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 Clearās 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 Godinās 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 Artistās 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:...
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The high-growth handbook: Molly Grahamās frameworks for leading through chaos, change, and scale
lenny@substack.com1/4/2026
View 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 worldās 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 doesnāt, 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 āextinctā within a year
What Jason is observing across his portfolio about AI adoption in GTM
How to become āhyper-employableā in the age of AI
The specific AI tools and tactics heās using that have been working best
Practical frameworks for integrating AI into your sales motion without losing what works
Jasonās 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 ]āThe developer intelligence platform designed by leading researchers
Vercel [ https://substack.com/redirect/873d8088-b453-4bda-994c-0256bf9133fe?j=eyJ1IjoiNzF4cDQwIn0.VLQsNiiAawz-DS2VtWTrcrG2IFeLIxnWNFcK9akSjpY ]āYour 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 ]āNow 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 ]
⢠Everyoneās an engineer now: Inside v0ās 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 ]
⢠SaaStrās 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 Halliganās 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 ]
⢠āSell the alpha, not the featureā: 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 canāt 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: Ripplingās 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:...
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We replaced our sales team with 20 AI agentsāhereās what happened | Jason Lemkin (SaaStr)
lenny@substack.com1/1/2026
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hiring
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marketplaces
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YouTube
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lenny@substack.com12/20/2025