Lenny's Podcast: Product | Growth | Career

Robby Stein is VP of Product at Google, where he oversees the core products of Google Search—including the new AI Overviews, AI Mode, search ranking, Google Lens, and more. Previously, he led consumer products at Instagram, where he and his teams built Stories, Reels, Close Friends, and other key features now used by billions.What you'll learn:1. Why Google's AI products are suddenly taking off after years of perceived stagnation2. How AI is expanding Search rather than replacing it, contrary to what many predicted3. The three core product principles that have helped Robby build multiple billion-user products4. Inside Instagram's decision to build its own version of Snapchat Stories5. His mantra of “relentless improvement”6. How Google developed AI Mode from concept to launch in just one year7. Why most teams give up too early on potentially transformative products—Brought to you by:• Vanta—Automate compliance. Simplify security: https://vanta.com/lenny• Jira Product Discovery—Confidence to build the right thing: https://atlassian.com/lenny/?utm_source=lennypodcast&utm_medium=paid-audio&utm_campaign=fy24q1-jpd-imc• Orkes—The enterprise platform for reliable applications and agentic workflows: https://www.orkes.io/—Transcript: ⁠https://www.lennysnewsletter.com/p/how-google-built-ai-mode-in-under-a-year⁠—My biggest takeaways (for paid newsletter subscribers): ⁠https://www.lennysnewsletter.com/i/175041217/my-biggest-takeaways-from-this-conversation⁠—Where to find Robby Stein:• X: https://x.com/rmstein• LinkedIn: https://www.linkedin.com/in/robbystein/—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Robby Stein(04:46) Google's recent success with AI(06:08) The evolution of Google Search(09:41) AI Mode and its impact(15:30) The rise of AEO(18:50) Building successful AI products(21:31)   Embodying relentless improvement(30:10) Lessons from Instagram Stories(35:20) Driving growth in established products(40:08) Balancing optimization and innovation(43:39) The journey of AI Mode: From launch to expansion(48:05) Organizational changes and urgency(49:51) AI Mode vs. competitors(51:35) Core product principles(57:07) Instagram's Close Friends feature(01:03:01) The importance of resources in development(01:06:39) AI corner(01:11:19) Curiosity and learning(01:15:01) Lightning round and final thoughts—Referenced:• Google Gemini: https://gemini.google.com/app• Nano Banana: https://aistudio.google.com/models/gemini-2-5-flash-image• Chat GPT: https://chatgpt.com/• Perplexity: https://www.perplexity.ai/• Google Lens: https://lens.google/• AI Google search: https://www.google.com/ai• Why ChatGPT will be the next big growth channel (and how to capitalize on it) | Brian Balfour (Reforge): https://www.lennysnewsletter.com/p/why-chatgpt-will-be-the-next-big-growth-channel-brian-balfour• Alex Rampell on X: https://x.com/arampell• A 4-step framework for building delightful products | Nesrine Changuel (Spotify, Google, Skype): https://www.lennysnewsletter.com/p/a-4-step-framework-for-building-delightful-products• Look broader, look closer, think younger: Tony Fadell speaks at TED2015: https://blog.ted.com/look-broader-look-closer-think-younger-tony-fadell-speaks-at-ted2015/• Jobs to Be Done: https://www.christenseninstitute.org/theory/jobs-to-be-done/• The ultimate guide to JTBD | Bob Moesta (co-creator of the framework): https://www.lennysnewsletter.com/p/the-ultimate-guide-to-jtbd-bob-moesta• Rinstagram or Finstagram? The curious duality of the modern Instagram user: https://www.theguardian.com/technology/2016/sep/26/rinstagram-finstagram-instagram-accounts• V03: https://v03ai.com/• Pirate GPT: https://www.kickstarter.com/projects/silentmeditation/pirate-gpt/• The Bear on Hulu: https://www.hulu.com/series/the-bear-05eb6a8e-90ed-4947-8c0b-e6536cbddd5f• Dune on HBO Max: https://www.hbomax.com/movies/dune/e7dc7b3a-a494-4ef1-8107-f4308aa6bbf7• Top Gun: Maverick: https://www.imdb.com/title/tt1745960/• Purple pillows: https://purple.com/pillows• Avocado pillow: https://www.avocadogreenmattress.com/products/green-pillow• Justin Bieber's website: https://www.justinbiebermusic.com/• Scooter Braun's website: https://scooterbraun.com/—Recommended books:• Competing Against Luck: The Story of Innovation and Customer Choice: https://www.amazon.com/Competing-Against-Luck-Innovation-Customer/dp/0062435612• The Design of Everyday Things: https://www.amazon.com/Design-Everyday-Things-Revised-Expanded/dp/0465050654• Aurora: https://www.amazon.com/Aurora-High-Stakes-Survival-Navigate-Darkness/dp/0062916475• Project Hail Mary: https://www.amazon.com/Project-Hail-Mary-Andy-Weir/dp/0593135202—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Jason Droege is the CEO of Scale AI, a company that provides foundational training data to every major AI lab. He previously co-founded Scour with Travis Kalanick and built Uber Eats from idea to $20 billion in revenue. In this conversation, Jason shares lessons from getting sued for $250 billion, discovering restaurant economics by weighing sandwich ingredients, and over 25 years of launching transformative technology businesses.What you'll learn:What actually happened with Meta's $14 billion investment in Scale AIWhy AI models still need human experts to improve, and how that relationship is evolvingHow AI models learn from experts building websites and debugging codeThe business lessons from building Uber Eats from zero to $20 billionWhy most enterprise data is useless for AI models todayWhy urgent daily problems beat super-valuable occasional problems when building productsHow to think independently when building new products and businesses—Brought to you by:Merge—The fastest way to ship 220+ integrations: http://merge.dev/lennyFigma Make—A prompt-to-code tool for making ideas real: https://www.figma.com/lenny/Mercury—The art of simplified finances: https://mercury.com/—Transcript: https://www.lennysnewsletter.com/p/first-interview-with-scale-ais-ceo-jason-droege—My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/174979621/my-biggest-takeaways-from-this-conversation—Where to find Jason Droege:• X: https://x.com/jdroege• LinkedIn: https://www.linkedin.com/in/jasondroege/—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Jason Droege(06:01) Jason's early career and lessons learned(10:27) The current state of Scale AI(12:37) The shift to expert data labeling(17:02) Challenges and strategies in finding experts(18:48) Reinforcement learning and AI environments(28:18) The future of AI and human involvement(31:21) The role of evals(35:25) What AI models will look like in the next few years(41:43) Building Uber Eats and understanding customer needs(48:19) The importance of independent thinking(50:45) Setting high standards for new businesses(53:03) Exploring and selecting business ideas(57:07) The McDonald's story(01:00:13) The role of gross margins in business feasibility(01:04:49) Why Jason says, “Not losing is a precursor to winning”(01:09:12) Hiring and building teams(01:12:11) AI corner(01:14:47) Lightning round and final thoughts—Referenced:• Travis Kalanick on X: https://x.com/travisk• Scour: https://en.wikipedia.org/wiki/Scour_Inc.• Scale: https://scale.com/• Alexandr Wang on X: https://x.com/alexandr_wang• 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• Brendan Foody's post on X about knowledge work changing: https://x.com/BrendanFoody/status/1970163503702188048• MIT Finds 95% of GenAI Pilots Fail Because Companies Avoid Friction: https://www.forbes.com/sites/jasonsnyder/2025/08/26/mit-finds-95-of-genai-pilots-fail-because-companies-avoid-friction/• Uber Eats: https://www.ubereats.com/• Stephen Chau on X: https://x.com/thestephenchau• a16z Podcast: https://a16z.com/podcasts/a16z-podcast/• F1: The Movie: https://www.imdb.com/title/tt16311594/• V03: https://v03ai.com/• Careers at Scale: https://scale.com/careers—Recommended books:• The Selfish Gene: https://www.amazon.com/Selfish-Gene-Anniversary-Introduction/dp/0199291152• The Road Less Traveled: A New Psychology of Love, Traditional Values, and Spiritual Growth: https://www.amazon.com/Road-Less-Traveled-Timeless-Traditional/dp/0743243153/• Good to Great: Why Some Companies Make the Leap . . . And Others Don't: https://www.amazon.com/Good-Great-Some-Companies-Others/dp/0066620996• Thinking, Fast and Slow: https://www.amazon.com/Thinking-Fast-Slow-Daniel-Kahneman/dp/0374533555/—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Albert Cheng has led growth at three of the world's most successful consumer subscription companies: Duolingo, Grammarly, and Chess.com. A former Google product manager (and serious pianist!), Albert developed a unique approach to finding and scaling growth opportunities through rapid experimentation and deep user psychology. His teams run 1,000 experiments a year, discovering counterintuitive insights that have driven tens of millions in revenue.What you'll learn:1. How to use the explore-exploit framework to find new growth opportunities2. How showing premium features to free users doubled Grammarly's upgrades to paid plans3. What good retention looks like for a consumer subscription app4. Why resurrected users drive 80% of mature product growth5. Why “reverse trials” work better than time-based trials6. The three pillars of successful gamification: core loop, metagame, and profile —Brought to you by:Vanta—Automate compliance. Simplify security.Jira Product Discovery—Confidence to build the right thingMiro—A collaborative visual platform where your best work comes to life—Where to find Albert Cheng:• X: https://x.com/albertc248• LinkedIn: https://www.linkedin.com/in/albertcheng1/• Chess.com: https://www.chess.com/member/Goniners—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—Referenced:• How Duolingo reignited user growth: https://www.lennysnewsletter.com/p/how-duolingo-reignited-user-growth• Inside ChatGPT: The fastest-growing product in history | Nick Turley (Head of ChatGPT at OpenAI): https://www.lennysnewsletter.com/p/inside-chatgpt-nick-turley• Explore vs. Exploit: https://brianbalfour.com/quick-takes/explore-vs-exploit• Grammarly: https://www.grammarly.com/• Reforge: https://www.reforge.com/• Chess.com: https://www.chess.com/• Everyone's an engineer now: Inside v0's mission to create a hundred million builders | Guillermo Rauch (founder & CEO of Vercel, creators of v0 and Next.js): https://www.lennysnewsletter.com/p/everyones-an-engineer-now-guillermo-rauch• Building Lovable: $10M ARR in 60 days with 15 people | Anton Osika (CEO and co-founder): https://www.lennysnewsletter.com/p/building-lovable-anton-osika• Figma: https://www.figma.com/• Cursor: https://cursor.com/• The rise of Cursor: The $300M ARR AI tool that engineers can't stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell• Claude Code: https://www.anthropic.com/claude-code• GitHub Copilot: https://github.com/features/copilot• Noam Lovinsky on LinkedIn: https://www.linkedin.com/in/noaml/• The happiness and pain of product management | Noam Lovinsky (Grammarly, Facebook, YouTube, Thumbtack): https://www.lennysnewsletter.com/p/the-happiness-and-pain-of-product• Kyla Siedband on LinkedIn: https://www.linkedin.com/in/kylasiedband/• The Duolingo handbook: https://blog.duolingo.com/handbook/• Lenny's post on X about the Duolingo handbook: https://x.com/lennysan/status/1889008405584683091• The rituals of great teams | Shishir Mehrotra of Coda, YouTube, Microsoft: https://www.lennysnewsletter.com/p/the-rituals-of-great-teams-shishir• Duolingo on TikTok: https://www.tiktok.com/@duolingo• Kasparov vs. Deep Blue | The Match That Changed History: https://www.chess.com/article/view/deep-blue-kasparov-chess• Magnus Carlsen: https://en.wikipedia.org/wiki/Magnus_Carlsen• Elo rating system: https://www.chess.com/terms/elo-rating-chess• Stockfish: https://en.wikipedia.org/wiki/Stockfish_(chess)• AlphaGo on Prime Video: https://www.primevideo.com/detail/AlphaGo/0KNQHKKDAOE8OCYKQS9WSSDYN0• Statsig: https://www.statsig.com/• The State of Product in 2026: Navigating Change, Challenge, and Opportunity: https://www.atlassian.com/blog/announcements/state-of-product-2026• Erik Allebest on LinkedIn: https://www.linkedin.com/in/erikallebest/• Daniel Rensch on X: https://x.com/danielrensch• Chariot: https://en.wikipedia.org/wiki/Chariot_(company)• San Francisco 49ers: https://www.49ers.com/• Breville Barista Express: https://www.breville.com/en-us/product/bes870—Recommended books:• Snuggle Puppy!: A Little Love Song: https://www.amazon.com/Snuggle-Puppy-Little-Boynton-Board/dp/1665924985• Ogilvy on Advertising: https://www.amazon.com/Ogilvy-Advertising-David/dp/039472903X• Dark Squares: How Chess Saved My Life: https://www.amazon.com/Dark-Squares-Chess-Saved-Life/dp/1541703286—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Nesrine Changuel helped build Spotify, Google Chrome, and Google Meet. Her work has helped her discover the importance of emotional connection in building successful products. At Google, she served as a dedicated “delight PM,” a role specifically focused on making products more delightful. She recently published Product Delight, a book that provides a practical framework for creating products that serve both functional and emotional needs. Based in Paris, she now coaches founders and CPOs on implementing delight strategies in their organizations.What you'll learn:1. Why delight is a business strategy, not just “sprinkling confetti” on top of functionality2. How to identify emotional motivators that drive product retention3. The 50-40-10 rule for balancing delight in your roadmap4. The 4-step delight model5. The origin story of Spotify's Discover Weekly6. Why B2B products need delight just as much as B2C products7. How to get buy-in from skeptical leaders who think delight is a luxury—Brought to you by:DX—The developer intelligence platform designed by leading researchers: https://getdx.com/lennyJira Product Discovery—Confidence to build the right thing: https://atlassian.com/lennyLucidLink—Real-time cloud storage for teams: https://www.lucidlink.com/lenny—Transcript: https://www.lennysnewsletter.com/p/a-4-step-framework-for-building-delightful-products—My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/174199489/my-biggest-takeaways-from-this-conversation—Where to find Nesrine Changuel:• LinkedIn: https://www.linkedin.com/in/nesrinechanguel/• Newsletter: https://nesrinechanguel.substack.com/• Website: https://nesrine-changuel.com/—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Nesrine and product delight(04:56) Why delight matters(09:17) What makes a feature “delightful”(12:29) The three pillars of delight(13:03) Pillar 1: Removing friction (Uber refund example)(15:07) Pillar 2: Anticipating needs (Revolut eSIM example)(17:21) Pillar 3: Exceeding expectations (Edge coupon example)(18:35) The “confetti effect” and when it actually works(22:02) B2B vs. B2C: Why all products need emotional connection(29:52) The Delight Model: A 4-step framework(30:57) Step 1: Identifying user motivators (functional and emotional)(33:55) Step 2: Converting motivators into product opportunities(34:46) Step 3: Identifying solutions with the delight grid(36:46) Step 4: Validating ideas with the delight checklist(40:22) The Delight Model summarized(42:18) The importance of familiarity (Spotify Discover Weekly story)(45:21) Real examples: Chrome's tab management solution(51:32) Google Meet's solution for “Zoom fatigue”(55:02) Getting buy-in from skeptical leaders(59:39) Prioritizing delight: The 50-40-10 rule(1:02:41) Creating a culture of delight in your organization(1:06:45) The habituation effect(1:08:15) When delight goes wrong: Apple reactions example(1:10:21) How delight motivates product teams(1:12:24) Lightning round and final thoughts—Referenced:• Spotify: https://open.spotify.com/• Linear: https://linear.app/• How Linear builds product: https://www.lennysnewsletter.com/p/how-linear-builds-product• Jira: https://www.atlassian.com/software/jira• Asana: https://asana.com/• Monday: https://monday.com/• The Product Delight Model: https://nesrinechanguel.substack.com/p/the-product-delight-model• Revolut: https://www.revolut.com/• How Revolut trains world-class product managers: The “local CEO” model, raw intellect over experience, and a cultural obsession with building wow products | Dmitry Zlokazov (Head of Product): https://www.lennysnewsletter.com/p/how-revolut-trains-world-class-product-managers• Microsoft Cashback: https://www.microsoft.com/en-us/edge/features/shopping-cashback• Superhuman's secret to success: Ignoring most customer feedback, manually onboarding every new user, obsessing over every detail, and positioning around a single attribute: speed | Rahul Vohra (CEO): https://www.lennysnewsletter.com/p/superhumans-secret-to-success-rahul-vohra• Brian Chesky's secret mentor who died 9 times, started the Burning Man board, and built the world's first midlife wisdom school | Chip Conley (founder of MEA): https://www.lennysnewsletter.com/p/chip-conley• Workday: https://www.workday.com/• SAP: https://www.sap.com/• ServiceNow: https://www.servicenow.com/• Salesforce: https://www.salesforce.com/• GitHub: https://github.com/• Atlassian: https://www.atlassian.com/• Snowflake: https://www.snowflake.com/• Data Superheroes: https://www.snowflake.com/en/data-superheroes/• Google Meet: https://meet.google.com/• Andy Nesling on LinkedIn: https://www.linkedin.com/in/andynesling/• Matic: https://maticrobots.com/• Diego Sanchez's (Senior Product Manager at Buffer) post on LinkedIn: https://www.linkedin.com/feed/update/urn:li:activity:7365014292091346945/• Miro: https://miro.com/• Arc browser: https://arc.net/• Competing with giants: An inside look at how The Browser Company builds product | Josh Miller (CEO): https://www.lennysnewsletter.com/p/competing-with-giants-an-inside-look• Migros Supermarket: https://www.migros.ch/• The rise of Cursor: The $300M ARR AI tool that engineers can't stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell• Building Lovable: $10M ARR in 60 days with 15 people | Anton Osika (CEO and co-founder): https://www.lennysnewsletter.com/p/building-lovable-anton-osika• Linear's secret to building beloved B2B products | Nan Yu (Head of Product): https://www.lennysnewsletter.com/p/linears-secret-to-building-beloved-b2b-products-nan-yu• Suno: https://suno.com• Snapchat: https://www.snapchat.com/• Use Reactions, Presenter Overlay, and other effects when videoconferencing on Mac: https://support.apple.com/en-us/105117• Dr. Lipp: https://drlipp.com/• How to be the best coach to product people | Petra Wille (Strong Product People): https://www.lennysnewsletter.com/p/how-to-be-the-best-coach-to-product• The Great American Baking Show: https://www.imdb.com/title/tt21822674/• Le Meilleur Pâtissier: https://en.wikipedia.org/wiki/Le_Meilleur_P%C3%A2tissier• The Upside on Amazon Prime: https://www.amazon.com/gp/video/detail/amzn1.dv.gti.3cb8500f-31af-9f4f-5dec-701e086d58e8• The Intouchables: https://www.imdb.com/title/tt1675434/• Yoyo stroller: https://www.stokke.com/USA/en-us/category/strollers/yoyo-strollers• UppaBaby strollers: https://uppababy.com/strollers/—Recommended books:• Product Delight: How to Make Your Product Stand Out with Emotional Connection: https://www.amazon.com/Product-Delight-Stand-Emotional-Connection-ebook/dp/B0FGZ93D9Y/• Factfulness: Ten Reasons We're Wrong About the World—and Why Things Are Better Than You Think: https://www.amazon.com/Factfulness-Reasons-World-Things-Better/dp/1250107814• STRONG Product Communities: The Essential Guide to Product Communities of Practice: https://www.amazon.com/STRONG-Product-Communities-Essential-Practice/dp/3982235189/r—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Hamel Husain and Shreya Shankar teach the world's most popular course on AI evals and have trained over 2,000 PMs and engineers (including many teams at OpenAI and Anthropic). In this conversation, they demystify the process of developing effective evals, walk through real examples, and share practical techniques that'll help you improve your AI product.What you'll learn:1. WTF evals are2. Why they've become the most important new skill for AI product builders3. A step-by-step walkthrough of how to create an effective eval4. A deep dive into error analysis, open coding, and axial coding5. Code-based evals vs. LLM-as-judge6. The most common pitfalls and how to avoid them7. Practical tips for implementing evals with minimal time investment (30 minutes per week after initial setup)8. Insight into the debate between “vibes” and systematic evals—Brought to you by:Fin—The #1 AI agent for customer serviceDscout—The UX platform to capture insights at every stage: from ideation to productionMercury—The art of simplified finances—Where to find Shreya Shankar• X: https://x.com/sh_reya• LinkedIn: https://www.linkedin.com/in/shrshnk/• Website: https://www.sh-reya.com/• Maven course: https://bit.ly/4myp27m—Where to find Hamel Husain• X: https://x.com/HamelHusain• LinkedIn: https://www.linkedin.com/in/hamelhusain/• Website: https://hamel.dev/• Maven course: https://bit.ly/4myp27m—In this episode, we cover:(00:00) Introduction to Hamel and Shreya(04:57) What are evals?(09:56) Demo: Examining real traces from a property management AI assistant(16:51) Writing notes on errors(23:54) Why LLMs can't replace humans in the initial error analysis(25:16) The concept of a “benevolent dictator” in the eval process(28:07) Theoretical saturation: when to stop(31:39) Using axial codes to help categorize and synthesize error notes(44:39) The results(46:06) Building an LLM-as-judge to evaluate specific failure modes(48:31) The difference between code-based evals and LLM-as-judge(52:10) Example: LLM-as-judge(54:45) Testing your LLM judge against human judgment(01:00:51) Why evals are the new PRDs for AI products(01:05:09) How many evals you actually need(01:07:41) What comes after evals(01:09:57) The great evals debate(1:15:15) Why dogfooding isn't enough for most AI products(01:18:23) OpenAI's Statsig acquisition(1:23:02) The Claude Code controversy and the importance of context(01:24:13) Common misconceptions around evals(1:22:28) Tips and tricks for implementing evals effectively(1:30:37) The time investment(1:33:38) Overview of their comprehensive evals course(1:37:57) Lightning round and final thoughts—LLM Log Open Codes Analysis Prompt:Please analyze the following CSV file. There is a metadata field which has an nested field called z_note that contains open codes for analysis of LLM logs that we are conducting. Please extract all of the different open codes. From the _note field, propose 5-6 categories that we can create axial codes from.—Referenced:• Building eval systems that improve your AI product: https://www.lennysnewsletter.com/p/building-eval-systems-that-improve• Mercor: https://mercor.com/• Brendan Foody on LinkedIn: https://www.linkedin.com/in/brendan-foody-2995ab10b• Nurture Boss: https://nurtureboss.io/• Braintrust: https://www.braintrust.dev/• Andrew Ng on X: https://x.com/andrewyng• Carrying Out Error Analysis: https://www.youtube.com/watch?v=JoAxZsdw_3w• Julius AI: https://julius.ai/• Brendan Foody on X—“evals are the new PRDs”: https://x.com/BrendanFoody/status/1939764763485171948• Who Validates the Validators? Aligning LLM-Assisted Evaluation of LLM Outputs with Human Preferences: https://dl.acm.org/doi/abs/10.1145/3654777.3676450• Lenny's post on X about evals: https://x.com/lennysan/status/1909636749103599729• Statsig: https://statsig.com/• Claude Code: https://www.anthropic.com/claude-code• Cursor: https://cursor.com/• Occam's razor: https://en.wikipedia.org/wiki/Occam%27s_razor• Frozen: https://www.imdb.com/title/tt2294629/• The Wire on HBO: https://en.wikipedia.org/wiki/The_Wire—Recommended books:• Pachinko: https://www.amazon.com/Pachinko-National-Book-Award-Finalist/dp/1455563935• Apple in China: The Capture of the World's Greatest Company: https://www.amazon.com/Apple-China-Capture-Greatest-Company/dp/1668053373/• Machine Learning: https://www.amazon.com/Machine-Learning-Tom-M-Mitchell/dp/1259096955• Artificial Intelligence: A Modern Approach: https://www.amazon.com/Artificial-Intelligence-Modern-Approach-Global/dp/1292401133/Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed.My biggest takeaways from this conversation: To hear more, visit www.lennysnewsletter.com

Julie Zhuo is the former VP and Head of Design at Facebook (now Meta), author of the bestselling book The Making of a Manager, and co-founder of Sundial, an AI-powered data analysis company. Also, my first-ever podcast guest over 3 years ago!In our conversation, we discuss:1. The three core manager skills that translate directly to managing AI agents2. How her team uses AI to learn new skills 10x faster3. The “diagnose with data, treat with design” framework for balancing gut and data4. Why hypergrowth AI companies have terrible data infrastructure (and why it doesn't matter)5. How to give feedback that actually lands—including Julie's exact script for difficult conversations6. What Julie's teaching her kids about an AI future (hint: it's not coding or STEM)—Brought to you by:Mercury — The art of simplified financesDX — The developer intelligence platform designed by leading researchersPostHog—How developers build successful products—Transcript: https://www.lennysnewsletter.com/p/from-managing-people-to-managing-ai-julie-zhuo—My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/172723725/my-biggest-takeaways-from-this-conversation—Where to find Julie Zhuo:• X: https://x.com/joulee• LinkedIn: https://www.linkedin.com/in/julie-zhuo/• Website: https://www.juliezhuo.com/• Newsletter: https://lg.substack.com/• Sundial: https://sundial.so/—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Welcome back, Julie!(05:18) The success of The Making of a Manager(08:41) Why AI will make everyone a manager(11:38) The future of management roles(14:00) Empowering teams with AI(21:30) Specific roles being accelerated by AI(26:53) Data analysis in AI companies(32:02) The role of data in design(37:21) The evolving role of managers in the AI era(40:22) Embracing change and uncertainty(42:14) Timeless lessons for managers(49:03) Balancing strengths and weaknesses(57:49) Building a feedback culture(01:05:33) Creating win-win situations(01:09:27) Being aware of your own energy and conviction(01:12:12) Navigating disagreements with higher-ups(01:15:57) AI corner(01:20:08) Contrarian corner(01:23:14) Lightning round and final thoughts—Referenced:• Julie Zhuo on accelerating your career, impostor syndrome, writing, building product sense, using intuition vs. data, hiring designers, and moving into management: https://www.lennysnewsletter.com/p/episode-2-julie-zhuo• Waymo: https://waymo.com/• How we restructured Airtable's entire org for AI | Howie Liu (co-founder and CEO): https://www.lennysnewsletter.com/p/how-we-restructured-airtables-entire-org-for-ai• Cursor: https://cursor.com/• The rise of Cursor: The $300M ARR AI tool that engineers can't stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell• Inside ChatGPT: The fastest growing product in history | Nick Turley (Head of ChatGPT at OpenAI): https://www.lennysnewsletter.com/p/inside-chatgpt-nick-turley• Behind the founder: Marc Benioff: https://www.lennysnewsletter.com/p/behind-the-founder-marc-benioff• OpenAI's CPO on how AI changes must-have skills, moats, coding, startup playbooks, more | Kevin Weil (CPO at OpenAI, ex-Instagram, Twitter): https://www.lennysnewsletter.com/p/kevin-weil-open-ai• Anthropic's CPO on what comes next | Mike Krieger (co-founder of Instagram): https://www.lennysnewsletter.com/p/anthropics-cpo-heres-what-comes-next• The Magic Loop: https://www.lennysnewsletter.com/p/the-magic-loop• Dunning-Kruger effect: https://en.wikipedia.org/wiki/Dunning%E2%80%93Kruger_effect• Eric Antonow on LinkedIn: https://www.linkedin.com/in/antonow/• Methaphone: https://methaphone.com/• Replit: https://replit.com/• “Baby” by Justin Bieber on Spotify: https://open.spotify.com/track/6epn3r7S14KUqlReYr77hA• Kingdom Rush: https://www.kingdomrush.com/• Dr. Becky on TikTok: https://www.tiktok.com/@drbeckyatgoodinside• Emily Oster on TikTok: https://www.tiktok.com/@profemilyoster• La La Land on Netflix: https://www.netflix.com/title/80095365• Granola: https://www.granola.ai/• Matic robots: https://maticrobots.com/• Limitless pendant: https://www.limitless.ai/• How I AI: https://www.youtube.com/@howiaipodcast—Recommended books:• The Making of a Manager: What to Do when Everyone Looks to You: https://www.amazon.com/Making-Manager-What-Everyone-Looks/dp/0525540423• High Output Management: https://www.amazon.com/High-Output-Management-Andrew-Grove/dp/0679762884/• Zen and the Art of Motorcycle Maintenance: An Inquiry into Values: https://www.amazon.com/Zen-Art-Motorcycle-Maintenance-Inquiry/dp/0061673730• Conscious Business: How to Build Value Through Values: https://www.amazon.com/Conscious-Business-Build-through-Values/dp/1622032020• Good Inside: A Practical Guide to Resilient Parenting Prioritizing Connection Over Correction: https://www.amazon.com/Good-Inside-Guide-Becoming-Parent/dp/0063159481/—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Brendan Foody is the CEO and co-founder of Mercor, the fastest-growing company in history to go from $1M to $500M in revenue (in just 17 months!). At 22, he is also the youngest American unicorn founder ever. Mercor works with 6 of the Magnificent 7 and all top 5 AI labs to help them hire experts to create evaluations and training data that improve their models. In this conversation, Brendan explains why evals have become the critical bottleneck for AI progress, how he discovered this massive opportunity, and what the future of work might look like in an AI-driven economy.What you'll learn:1. Why evals are becoming the primary bottleneck for AI progress and what this means for AI startups2. How Mercor grew to $500M revenue in 17 months (fastest in history)3. Brendan's meeting with xAI that changed his company's trajectory4. Which skills and jobs will remain most valuable as AI continues to advance (hint: jobs with “elastic” demand)5. Why Brendan believes AGI and superintelligence are not happening anytime soon6. The three unique core values that drove Mercor's success7. How Harvard Lampoon writers are making Claude funnier—Brought to you by:WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUsJira Product Discovery—Atlassian's new prioritization and roadmapping tool built for product teamsEnterpret—Transform customer feedback into product growth—Transcript: https://www.lennysnewsletter.com/p/experts-writing-ai-evals-brendan-foody—My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/173303790/my-biggest-takeaways-from-this-conversation—Where to find Brendan Foody:• X: https://x.com/BrendanFoody• LinkedIn: https://www.linkedin.com/in/brendan-foody-2995ab10b/—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Brendan Foody and Mercor(05:38) The “era of evals”(09:26) Understanding the AI training landscape(17:10) The future of work and AI(25:54) The evolution of labor markets(29:55) Understanding how AI models are trained(38:58) Building Mercor(53:27) Lessons from past ventures(56:55) The future of AI and model improvement(01:00:41) His personal use of AI and final thoughts—References: https://www.lennysnewsletter.com/p/experts-writing-ai-evals-brendan-foody—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Ethan Smith is the CEO of Graphite—the leading SEO growth agency—and my go-to expert on SEO. After 18 years of mastering traditional SEO, Ethan has been at the forefront of what is called AEO: answer engine optimization, or, more simply, getting your product to show up in ChatGPT/Claude/Gemini/Perplexity answers. He's discovered that ChatGPT traffic converts six times better than Google search—and most companies are completely missing this opportunity.In our conversation, we discuss:1. His 7-step playbook to rank #1 in ChatGPT2. Why ChatGPT traffic converts 6x better than Google3. How early-stage startups can win at AEO immediately (unlike with SEO, which takes years)4. The three tactics that actually work: landing pages, YouTube videos, and Reddit comments5. Why help-center content can suddenly be your highest-ROI investment6. The specific Reddit strategy that works (spoiler: be authentic)7. Why AI-generated content doesn't work—Brought to you by:Orkes—The enterprise platform for reliable applications and agentic workflowsVanta—Automate compliance. Simplify security.Great Question—Empower everyone to run great research—Where to find Ethan Smith:• Twitter: https://twitter.com/ethan_l_s• LinkedIn: https://bit.ly/ethans-linkedin• Graphite: https://graphite.io/• Graphite Research Papers: https://bit.ly/graphite-five-percent—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Welcome back, Ethan(04:34) The changing landscape of SEO(06:19) AEO (answer engine optimization) vs. GEO (generative engine optimization)(08:13) The impact of AEO(11:51) How early-stage startups can win at AEO(14:34) The quality of AEO leads(15:35) On-site vs. off-site traffic(16:32) Reddit's role in AEO and avoiding spam(20:11) How AI models use citations (RAG)(21:41) Key principles for winning at AEO(25:00) Avoiding hyper-SEOed content, and the importance of originality(28:55) Actionable AEO playbook: steps and experiments(33:35) Tracking, measuring, and share of voice(38:34) Adapting AEO for B2B, commerce, and early-stage companies(41:11) Is letting AI index your content good?(43:06) Experimentation, control groups, and measuring results(46:15) The future of AEO, SEO, and search channels(51:35) AI-generated content: what works and what doesn't(55:25) The dangers of infinite AI derivatives(58:44) The future: convergence of LLMs and search(01:00:40) Help-center optimization and the long tail(01:03:18) Lightning round and final thoughts—Resources and episode mentions: https://www.lennysnewsletter.com/p/the-ultimate-guide-to-aeo-ethan-smith—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Ben Horowitz is the co-founder of Andreessen Horowitz, Silicon Valley's largest and most influential venture capital firm, with over $46B in committed capital across multiple funds. He took Loudcloud public with just $2 million in revenue (dubbed “the IPO from hell”), sold it for $1.6 billion, and has backed companies from Facebook to Stripe to Airbnb to OpenAI to Databricks (now worth more than $100 billion). His management philosophy—forged through near-death experiences and refined through coaching hundreds of CEOs—contradicts most conventional startup wisdom.In our conversation, Ben shares:1. Why “founder mode” is half right and half dangerously wrong2. The story behind “Good Product Manager/Bad Product Manager” and why it went viral despite being written in anger3. Where the biggest AI startup opportunities remain4. Why you need to run toward fear, never away5. The one trait that predicts that a founder will fail as CEO6. Inside Paid in Full, Ben's nonprofit awarding pensions to pioneering hip-hop artists—Brought to you by:DX—The developer intelligence platform designed by leading researchers: http://getdx.com/lennyBasecamp—The famously straightforward project management system from 37signals: https://www.basecamp.com/lennyMiro—A collaborative visual platform where your best work comes to life: https://miro.com/lenny—Transcript: https://www.lennysnewsletter.com/p/46b-of-hard-truths-from-ben-horowitz—My biggest takeaways (for paid newsletter subscribers): ⁠https://www.lennysnewsletter.com/i/172439345/my-biggest-takeaways-from-this-conversation—Where to find Ben Horowitz:• X: https://x.com/bhorowitz• LinkedIn: https://www.linkedin.com/in/behorowitz/• Website: https://benhorowitz.com/• Andreessen Horowitz's website: https://a16z.com/—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Ben Horowitz(04:09) Important leadership lessons from Shaka Senghor(10:15) Running toward fear and why hesitation kills companies(19:35) Who shouldn't start a company(22:36) The Databricks story: thinking bigger(24:54) Managerial leverage and CEO psychology(28:06) When founders should be replaced as CEOs(31:20) Normalizing failure for CEOs(37:57) Counterintuitive lessons about building companies(42:31) “Good Product Manager/Bad Product Manager”(48:21) Product managers as leaders(51:16) Why a16z invested in Adam Neumann after WeWork(56:23) Is AI in a bubble?(01:02:43) The biggest opportunities in AI(01:12:51) Why U.S. leadership in AI matters(01:18:53) The Paid in Full Foundation for hip-hop pioneers(01:23:18) Lightning round: book recommendations, products, and life mottos—References: https://www.lennysnewsletter.com/p/46b-of-hard-truths-from-ben-horowitz—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Ezinne and Oji Udezue have over 50 years of combined product leadership experience at Microsoft, Twitter, Atlassian, WP Engine, Typeform, and Calendly. They've witnessed every major shift in product management, and, despite their seniority, they're taking beginner AI courses and learning from engineers half their age, and Oji is coding more now than in the past decade—from Waterfall to Agile to AI. They are also the authors of Building Rocketships, a guide to building great products. In this conversation, the couple shares hard-won lessons they've learned from companies successfully adapting to AI, including their “shipyard” framework and their “sharp problem” methodology.What you'll learn:1. The “shipyard” framework: why the best AI teams embrace controlled chaos2. Why Oji writes more code now than in the past 10 years—despite being a PM for more than 25 years3. The three skills that matter most for PMs in 2025: curiosity, humility, and agency4. How to identify “sharp problems”5. AI at the core vs. AI at the edge: why companies that are building entirely new AI-centric codebases will beat those just “sprinkling AI” on existing products6. The counterintuitive truth: engineers are moving so fast with AI that PMs are now the bottleneck7. Their biggest product lesson from 50 combined years—Brought to you by:Mercury—The art of simplified financesVanta—Automate compliance. Simplify security.Coda—The all-in-one collaborative workspace—Where to find Oji and Ezinne:• ProductMind on Substack: https://substack.com/@ojiudezue• ProductMind on LinkedIn: https://www.linkedin.com/company/productmindco• ProductMind on YouTube: https://www.youtube.com/@ProductMindX/videos• ProductMind on Spotify: https://open.spotify.com/show/07OVh5pdSv0szHPwWktzQQ• ProductMind website: https://www.productmind.co/• Oji on LinkedIn: https://www.linkedin.com/in/ojiudezue/• Ezinne on LinkedIn: https://www.linkedin.com/in/ezinne/—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Oji and Ezinne(04:14) The evolving role of product managers(08:01) Challenges and opportunities in product management(10:34) Sharp problems(12:37) The shipyard model for product development(17:02) Hiring PMs in the AI era(24:55) The importance of staying humble(27:16) Hands-on learning and personal projects(39:10) Companies succeeding with AI adoption(46:25) Lessons from 50 years in product(49:22) Simplicity in design(51:24) The role of communication in strategy(55:17) Career intentions and personal growth(01:00:00) Ethics and responsibility in product management(01:03:09) Introducing Building Rocketships(01:06:42) Lightning round and final thoughts—Referenced:• How 80,000 companies build with AI: products as organisms, the death of org charts, and why agents will outnumber employees by 2026 | Asha Sharma (CVP of AI Platform at Microsoft): https://www.lennysnewsletter.com/p/how-80000-companies-build-with-ai-asha-sharma• Picking sharp problems, increasing virality, and unique product frameworks | Oji Udezue (Typeform, Twitter, Calendly, Atlassian): https://www.lennysnewsletter.com/p/picking-sharp-problems-increasing• Atlassian: https://www.atlassian.com/• Joff Redfern on LinkedIn: https://www.linkedin.com/in/mejoff/• Brownian motion: https://en.wikipedia.org/wiki/Brownian_motion• Calendly: https://calendly.com/• Women in Product: https://womenpm.org/• Brian Chesky's secret mentor who died 9 times, started the Burning Man board, and built the world's first midlife wisdom school | Chip Conley (founder of MEA): https://www.lennysnewsletter.com/p/chip-conley• Home Assistant: https://www.home-assistant.io/• What people are vibe coding (and actually using): https://www.lennysnewsletter.com/p/what-people-are-vibe-coding-and-actually• How many layers should I wear today?: https://layers.today/• Typeform: https://www.typeform.com/• David Okuniev on X: https://x.com/okuiux• Clay: https://www.clay.com/• Martin Eriksson on LinkedIn: https://www.linkedin.com/in/martineriksson/• Geoffrey Moore on finding your beachhead, crossing the chasm, and dominating a market: https://www.lennysnewsletter.com/p/geoffrey-moore-on-finding-your-beachhead• Dave Mendlen on LinkedIn: https://www.linkedin.com/in/davemendlen/• Deepfake: https://en.wikipedia.org/wiki/Deepfake• How to kickstart and scale a marketplace business: https://www.lennysnewsletter.com/p/how-to-kickstart-and-scale-a-marketplace• Forever on Netflix: https://www.netflix.com/title/81418639• Paradise on Hulu: https://www.hulu.com/series/paradise-2b4b8988-50c9-4097-bf93-bc34a99a5b4f• Sinners: https://www.imdb.com/title/tt31193180/• Claude: https://claude.ai/• Nespresso Vertuo: https://www.nespresso.com/us/en/vertuo-coffee-machines• Gamma: https://gamma.app/• Framer: https://www.framer.com/• Lovable: https://lovable.dev/• Building Lovable: $10M ARR in 60 days with 15 people | Anton Osika (CEO and co-founder): https://www.lennysnewsletter.com/p/building-lovable-anton-osika• Llama: https://www.llama.com/—Recommended books:• Building Rocketships: Product Management for High-Growth Companies: https://www.amazon.com/Building-Rocketships-Management-High-Growth-Companies/dp/1962339068• Coda version of Building Rocketships: https://www.productmind.co/brpro• Build: An Unorthodox Guide to Making Things Worth Making: https://www.amazon.com/Build-Unorthodox-Guide-Making-Things/dp/0063046067• The Let Them Theory: A Life-Changing Tool That Millions of People Can't Stop Talking About: https://www.amazon.com/Let-Them-Theory-Life-Changing-Millions/dp/1401971369/Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed.My biggest takeaways from this conversation: To hear more, visit www.lennysnewsletter.com

Howie Liu is the co-founder and CEO of Airtable, the no-code platform valued at around $12 billion. After a viral tweet declared “Airtable is dead” based on incorrect data, Howie led a radical transformation: reorganizing the entire company around AI, becoming an “IC CEO” who codes daily, and achieving over $100 million in free cash flow.What you'll learn:1. The “fast thinking” vs. “slow thinking” team structure that lets Airtable ship AI features weekly (inspired by Daniel Kahneman)2. Why Howie uses AI hourly (not daily) and is Airtable's #1 inference-cost user globally3. Why CEOs must become ICs again in the AI era (and how to restructure your calendar to make it possible)4. Why “playing” with AI tools should be mandatory—Howie tells employees to cancel all meetings for a week to experiment5. The specific skills product managers, engineers, and designers need to develop to succeed in the AI era6. Why evals can kill innovation (and when to use “vibes” instead)—Brought to you by:LucidLink—Real-time cloud storage for teamsDX—The developer intelligence platform designed by leading researchersClaude.ai—The AI for problem solvers and enterprise—Where to find Howie Liu• X: https://x.com/howietl• LinkedIn: https://www.linkedin.com/in/howieliu/• Email: howie@airtable.com—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Howie Liu and Airtable(04:05) The “Airtable is dead” viral tweet controversy(08:07) The rise of IC CEOs(10:57) AI's paradigm shift in product development(16:27) Specific changes Airtable has made(21:38) Fast- and slow-thinking teams(32:57) The emergence of new form factors in AI models(34:48) Airtable's vision and philosophy(40:20) Empowering teams with AI tools(46:50) Encouraging experimentation and play(50:55) Cross-functional skills in product teams(01:03:35) The importance of evals and open-ended testing(01:08:06) Key strategies for AI-driven success(01:12:43) Counterintuitive startup wisdom(01:22:21) Don't step away from the details that you love(01:25:50) Advice for aspiring engineers and designers(01:30:00) Lightning round and final thoughts—Referenced:• Airtable: https://www.airtable.com/• All In podcast: https://allin.com/• Nikita Bier on X: https://x.com/nikitabier• Figma: https://www.figma.com/• The AI-native startup: 5 products, 7-figure revenue, 100% AI-written code | Dan Shipper (co-founder and CEO of Every): https://www.lennysnewsletter.com/p/inside-every-dan-shipper• Every: https://every.to/• Cursor: https://cursor.com/• The rise of Cursor: The $300M ARR AI tool that engineers can't stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell• Windsurf: https://windsurf.com/• Building a magical AI code editor used by over 1 million developers in four months: The untold story of Windsurf | Varun Mohan (co-founder and CEO): https://www.lennysnewsletter.com/p/the-untold-story-of-windsurf-varun-mohan• Rippling: https://www.rippling.com/• Omni: https://www.airtable.com/lp/ai-psu-plp• How ChatGPT accidentally became the fastest-growing product in history | Nick Turley (Head of ChatGPT at OpenAI): https://www.lennysnewsletter.com/p/inside-chatgpt-nick-turley• Palantir: https://www.palantir.com/• Harvey: https://www.harvey.ai/• v0: https://v0.dev/• Everyone's an engineer now: Inside v0's mission to create a hundred million builders | Guillermo Rauch (founder and CEO of Vercel, creators of v0 and Next.js): https://www.lennysnewsletter.com/p/everyones-an-engineer-now-guillermo-rauch• Replit: https://replit.com/• Behind the product: Replit | Amjad Masad (co-founder and CEO): https://www.lennysnewsletter.com/p/behind-the-product-replit-amjad-masad• Lovable: https://lovable.dev/• Building Lovable: $10M ARR in 60 days with 15 people | Anton Osika (CEO and co-founder): https://www.lennysnewsletter.com/p/building-lovable-anton-osika• Runway Game Worlds: https://play.runwayml.com/login• Sesame: https://www.sesame.com• NotebookLM: https://notebooklm.google• Salesforce: https://www.salesforce.com• Andrew Ofstad on LinkedIn: https://www.linkedin.com/in/aofstad/• Stripe: https://stripe.com/• Eames chair: https://en.wikipedia.org/wiki/Eames_Lounge_Chair• OpenAI's CPO on how AI changes must-have skills, moats, coding, startup playbooks, more | Kevin Weil (CPO at OpenAI, ex-Instagram, Twitter): https://www.lennysnewsletter.com/p/kevin-weil-open-ai• Anthropic's CPO on what comes next | Mike Krieger (co-founder of Instagram): https://www.lennysnewsletter.com/p/anthropics-cpo-heres-what-comes-next• IDEO design thinking: https://designthinking.ideo.com/• Brian Chesky's new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach• The Studio on AppleTV+: https://tv.apple.com/us/show/the-studio/umc.cmc.7518algxc4lsoobtsx30dqb52• Silicon Valley on HBOMax: https://www.hbomax.com/shows/silicon-valley/b4583939-e39f-4b5c-822d-5b6cc186172d• Self Edge: https://www.selfedge.com/• Studio D'Artisan: https://www.selfedge.com/studio-dartisan• Whitesville T-shirt: https://store.toyo-enterprise.co.jp/shopbrand/ct48/• Guest Series | Dr. Paul Conti: How to Understand & Assess Your Mental Health: https://www.hubermanlab.com/episode/guest-series-dr-paul-conti-how-to-understand-and-assess-your-mental-health—Recommended books:• Thinking, Fast and Slow: https://www.amazon.com/Thinking-Fast-Slow-Daniel-Kahneman/dp/0374533555• The Three-Body Problem: https://www.amazon.com/Three-Body-Problem-Cixin-Liu/dp/0765382032• Trauma: The Invisible Epidemic: How Trauma Works and How We Can Heal From It: https://us.amazon.com/Trauma-Invisible-Epidemic-Works-Heal/dp/1683647351/—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Asha Sharma leads AI product strategy at Microsoft, where she works with thousands of companies building AI products and has unique visibility into what's working (and what's not) across more than 15,000 startups and enterprises. Before Microsoft, Asha was COO at Instacart, and VP of Product & Engineering at Meta, notably leading product for Messenger.What you'll learn:1. Why we're moving from “product as artifact” to “product as organism” and what this means for builders2. Microsoft's “seasons” planning framework that allows them to adapt quickly in the AI era3. The death of the org chart: how agents are turning hierarchies into task networks and why “the loop, not the lane” is the new organizing principle4. Why post-training will soon see more investment than pre-training—and how to build your own AI moat with fine-tuning5. Her prediction for the “agentic society”—where org charts become work charts and agents outnumber humans in your company6. The three-phase pattern every successful AI company follows (and why most fail at phase one)7. The rise of code-native interfaces and why GUIs might be going the way of the desktop8. What Asha learned from Satya Nadella about optimism—Brought to you by:Enterpret—Transform customer feedback into product growth: https://enterpret.com/lennyDX—The developer intelligence platform designed by leading researchers: http://getdx.com/lennyFin—The #1 AI agent for customer service: https://fin.ai/lenny—Transcript: ⁠https://www.lennysnewsletter.com/p/how-80000-companies-build-with-ai-asha-sharma⁠—My biggest takeaways (for paid newsletter subscribers): ⁠https://www.lennysnewsletter.com/i/171413445/my-biggest-takeaways-from-this-conversation⁠—Where to find Asha Sharma:• LinkedIn: https://www.linkedin.com/in/aboutasha/• Blog: https://azure.microsoft.com/en-us/blog/author/asha-sharma/—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Asha Sharma(04:18) From “product as artifact” to “product as organism”(06:20) The rise of post-training and the future of AI product development(09:10) Successful AI companies: patterns and pitfalls(12:01) The evolution of full-stack builders(14:15) “The loop, not the lane”—the new organizing principle(16:24) The future of user interfaces: from GUI to code-native(19:34) The rise of the agentic society(22:58) The “work chart” vs. the “org chart”(26:24) How Microsoft is using agents(28:23) Planning and strategy in the AI landscape(35:38) The importance of platform fundamentals(39:31) Lessons from industry giants(42:10) What's driving Asha(44:30) Reinforcement learning (RL) and optimization loops(49:19) Lightning round and final thoughts—Referenced:• Copilot: https://copilot.microsoft.com/• Cursor: https://cursor.com/• The rise of Cursor: The $300M ARR AI tool that engineers can't stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell• Inside ChatGPT: The fastest growing product in history | Nick Turley (Head of ChatGPT at OpenAI): https://www.lennysnewsletter.com/p/inside-chatgpt-nick-turley• GitHub: https://github.com• Dragon Medical One: https://www.microsoft.com/en-us/health-solutions/clinical-workflow/dragon-medical-one• Windsurf: https://windsurf.com/• Building a magical AI code editor used by over 1 million developers in four months: The untold story of Windsurf | Varun Mohan (co-founder and CEO): https://www.lennysnewsletter.com/p/the-untold-story-of-windsurf-varun-mohan• Lovable: https://lovable.dev/• Building Lovable: $10M ARR in 60 days with 15 people | Anton Osika (CEO and co-founder): https://www.lennysnewsletter.com/p/building-lovable-anton-osika• Bolt: http://bolt.com• Inside Bolt: From near-death to ~$40m ARR in 5 months—one of the fastest-growing products in history | Eric Simons (founder and CEO of StackBlitz): https://www.lennysnewsletter.com/p/inside-bolt-eric-simons• Replit: https://replit.com/•Behind the product: Replit | Amjad Masad (co-founder and CEO): https://www.lennysnewsletter.com/p/behind-the-product-replit-amjad-masad• He saved OpenAI, invented the “Like” button, and built Google Maps: Bret Taylor on the future of careers, coding, agents, and more: https://www.lennysnewsletter.com/p/he-saved-openai-bret-taylor• Sierra: https://sierra.ai/• Spark: https://github.com/features/spark• Peter Yang on X: https://x.com/petergyang• How AI will impact product management: https://www.lennysnewsletter.com/p/how-ai-will-impact-product-management• Instacart: http://instacart.com/• Terminator: https://en.wikipedia.org/wiki/Terminator_(franchise)• Porch Group: https://porchgroup.com/• WhatsApp: https://www.whatsapp.com/• Maslow's Hierarchy of Needs: https://www.simplypsychology.org/maslow.html• Satya Nadella on X: https://x.com/satyanadella• Perfect Match 360°: Artificial intelligence to find the perfect donor match: https://ivi-fertility.com/blog/perfect-match-360-artificial-intelligence-to-find-the-perfect-donor-match/• OpenAI's GPT-5 shows potential in healthcare with early cancer detection capabilities: https://economictimes.indiatimes.com/news/international/us/openais-gpt-5-shows-potential-in-healthcare-with-early-cancer-detection-capabilities/articleshow/123173952.cms• F1: The Movie: https://www.imdb.com/title/tt16311594/• For All Mankind on AppleTV+: https://tv.apple.com/us/show/for-all-mankind/umc.cmc.6wsi780sz5tdbqcf11k76mkp7• The Home Depot: https://www.homedepot.com/• Dewalt Powerstack: https://www.dewalt.com/powerstack• Regret Minimization Framework: https://s3.amazonaws.com/kajabi-storefronts-production/sites/2147500522/themes/2148012322/downloads/rLuObc2QuOwjLrinx5Yu_regret-minimization-framework.pdf—Recommended books:• The Thinking Machine: Jensen Huang, Nvidia, and the World's Most Coveted Microchip: https://www.amazon.com/Thinking-Machine-Jensen-Coveted-Microchip/dp/0593832698• Tomorrow, and Tomorrow, and Tomorrow: https://www.amazon.com/dp/0593466497Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed.My biggest takeaways from this conversation: To hear more, visit www.lennysnewsletter.com

Garrett Lord is co-founder and CEO of Handshake, which started as a career network for college students and new grads but recently discovered something extraordinary: they were sitting on the world's largest network of academic experts—exactly what frontier AI labs desperately needed. With 500,000 PhDs and 3 million advanced degree holders creating training data, in just eight months they've built a new business that hit $50 million in revenue in its first four months and is on track to blow past $100M in the first 12 months.What you'll learn:1. How Handshake found an opportunity to leverage their proprietary network of experts to launch a data-labeling business that's on track to blow past $100 million ARR in 12 months2. Why AI models need human experts (e.g. physics PhDs) to improve, and what this “data labeling” actually involves3. Inside the actual work: what a biology PhD does for 8 hours that makes GPT-5 smarter4. The playbook for building a startup inside a startup: separate teams, separate offices, separate everything5. Why the shift from “generalist” to “expert” data labeling created a once-in-a-lifetime business opportunity6. Why AI won't eliminate entry-level jobs—it's creating “Iron Man suits” that make junior employees 10x more productive—Brought to you by:CodeRabbit—Cut code review time and bugs in half. Instantly: https://coderabbit.link/lennyOrkes—The enterprise platform for reliable applications and agentic workflows: https://www.orkes.io/Claude.ai—The AI for problem solvers and enterprise: http://claude.ai/—Transcript: https://www.lennysnewsletter.com/p/inside-handshake-garrett-lord—My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/171410958/my-biggest-takeaways-from-this-conversation—Where to find Garrett Lord:• X: https://x.com/garrettlord• LinkedIn: https://www.linkedin.com/in/garrettlord/• Email: Garrett@joinhandshake.com—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Garrett Lord(05:00) Understanding data labeling and its importance(13:08) The role of experts in AI model training(15:35) The future of AI and human collaboration(24:17) Why AI won't eliminate entry-level jobs(27:58) The continuous improvement of AI models(33:05) The emergence of Handshake's new business model(37:07) Incubating new ideas in established companies(40:42) Handshake's competitive advantage(45:43) Scaling up and meeting market demand(48:38) Overcoming challenges and adapting(53:08) The importance of separate teams and ownership(57:26) The future of job matching with AI(01:00:30) The biggest bottlenecks to advancing models further(01:02:37) Lightning round and final thoughts—Referenced:• GPQA: https://github.com/idavidrein/gpqa• Handshake: https://joinhandshake.com/• OpenAI's CPO on how AI changes must-have skills, moats, coding, startup playbooks, more | Kevin Weil (CPO at OpenAI, ex-Instagram, Twitter): https://www.lennysnewsletter.com/p/kevin-weil-open-ai• Inside Bolt: From near-death to ~$40m ARR in 5 months—one of the fastest-growing products in history | Eric Simons (founder and CEO of StackBlitz): https://www.lennysnewsletter.com/p/inside-bolt-eric-simons• Goldman Sachs: https://www.goldmansachs.com/• General Motors: https://www.gm.com/• Google: https://about.google/• Sahil Bhaiwala on LinkedIn: https://www.linkedin.com/in/sahil-bhaiwala-459b0354/• Francisco “Paco” Guzman on LinkedIn: https://www.linkedin.com/in/guzmanhe/• Avery Yip on LinkedIn: https://www.linkedin.com/in/averyyip/• Game of Thrones on HBO: https://www.hbomax.com/shows/game-of-thrones/4f6b4985-2dc9-4ab6-ac79-d60f0860b0ac• SNOO: https://www.happiestbaby.com/products/snoo-smart-bassinet• Careers at Handshake: https://joinhandshake.com/careers/—Recommended books:• Zero to One: Notes on Startups, or How to Build the Future: https://www.amazon.com/Zero-One-Notes-Startups-Future/dp/0804139296• The Hard Thing About Hard Things: Building a Business When There Are No Easy Answers―Straight Talk on the Challenges of Entrepreneurship: https://www.amazon.com/Hard-Thing-About-Things-Building/dp/0062273205—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Eoghan McCabe is the founder and CEO of Intercom, a customer service platform that has successfully pivoted to become an AI-first company with its agent product, Fin. After stepping away from the CEO role in 2020 due to health issues, Eoghan returned to find the company's growth had stalled. Just one month after his return, ChatGPT launched, and within six weeks, Intercom had a working prototype of what would become Fin. In this conversation, Eoghan shares the brutal reality of transforming a late-stage SaaS business valued at multiple billions into an AI-first company that's now growing faster than most public software companies.We discuss:1. Why Eoghan believes most late-stage companies won't survive the AI transition2. The “founder mode” transformation that required firing 40% of staff and resulted in 98% employee satisfaction3. Why having “nothing to lose” is the ultimate advantage in AI transformation (and why comfortable companies will fail)4. How Intercom transformed from a plateauing SaaS business to an AI-first company growing at 300%+5. How Intercom's pricing evolved from “the most hated in SaaS” to a model that charges just $0.99 per resolved ticket6. The cultural transformation required to compete with AI-native startups7. How 12 years of therapy and a period of “ego death” shaped Eoghan's leadership approach—Brought to you by:Great Question—Empower everyone to run great research: https://www.greatquestion.com/lennyWorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs: https://workos.com/lennyDX—The developer intelligence platform designed by leading researchers: http://getdx.com/lenny—Transcript: ⁠https://www.lennysnewsletter.com/p/how-intercom-rose-from-the-ashes-eoghan-mccabe—My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/170710700/my-biggest-takeaways-from-this-conversation—Where to find Eoghan McCabe:• X: https://x.com/eoghan• LinkedIn: https://www.linkedin.com/in/eoghanmccabe/• Website: https://eoghanmccabe.com/—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Eoghan(05:00) The state of Intercom(09:53) The decision to pivot to AI(12:33) Why Eoghan is "anti-bot" in customer service(16:19) Pricing strategy evolution(19:26) Implementing the AI transformation(26:11) Cultural and organizational changes(31:18) Surviving a coup attempt(40:05) The future of AI and business(45:11) AI's impact on jobs(48:44) AI and human creativity(50:26) The importance of young AI talent(55:00) The cultural shift in AI adoption(58:00) Personal growth and leadership(01:04:34) Intercom's success in producing product leaders(01:11:05) Intercom's unique company culture(01:14:11) Lightning round and final thoughts—Referenced:• Intercom: https://www.intercom.com/• Fin: https://fin.ai/• Des Traynor on LinkedIn: https://www.linkedin.com/in/destraynor/• The art and science of pricing | Madhavan Ramanujam (Monetizing Innovation, Simon-Kucher): https://www.lennysnewsletter.com/p/the-art-and-science-of-pricing-madhavan• 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• Brian Chesky's new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach• Behind the founder: Marc Benioff: https://www.lennysnewsletter.com/p/behind-the-founder-marc-benioff• 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• Fergal Reid on LinkedIn: https://www.linkedin.com/in/fergalreid/• How Perplexity builds product: https://www.lennysnewsletter.com/p/how-perplexity-builds-product• Yosi Amram's website: https://yamram.com/• (Nathaniel Russell) Ego Death Now: https://heythereprojects.shop/products/copy-of-nathaniel-russell-space-is-a-place• Daniel Kahneman: https://en.wikipedia.org/wiki/Daniel_Kahneman• Palantir: https://www.palantir.com/• Stripe: https://stripe.com/• Revolut: https://www.revolut.com/en-US/• Paul Adams on LinkedIn: https://www.linkedin.com/in/pauladams• What AI means for your product strategy | Paul Adams (CPO of Intercom): https://www.lennysnewsletter.com/p/what-ai-means-for-your-product-strategy• Which companies accelerate PM careers most: https://www.lennysnewsletter.com/p/which-companies-accelerate-your-pm• N26: https://n26.com/en-eu• Notion: https://www.notion.so/• Coinbase: https://www.coinbase.com/• True Detective on Max: https://www.hbomax.com/shows/true-detective/9a4a3645-74e0-4e4d-9f35-31464b402357• 28 Years Later: https://www.imdb.com/title/tt10548174/• Trainspotting: https://www.imdb.com/title/tt0117951/• 28 Days Later: https://www.imdb.com/title/tt0289043/• Fellow: https://fellowproducts.com/• Porsche 911: https://www.porsche.com/usa/models/911/• Making Meta | Andrew ‘Boz' Bosworth (CTO): https://www.lennysnewsletter.com/p/making-meta-andrew-boz-bosworth-cto—Recommended book:• Nuclear War: A Scenario: https://www.amazon.com/Nuclear-War-Scenario-Annie-Jacobsen/dp/0593476093Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Brian Balfour is the founder of Reforge, the former VP of Growth at HubSpot, and a student (and teacher) of product growth. Brian has studied every major platform shift—from Facebook to Apple to Google—and he's spotted a pattern that's about to repeat with ChatGPT.In this conversation, you'll learn:1. The 4-step cycle every platform follows (and why ChatGPT just entered step 2)2. Why ChatGPT's platform launch could be bigger than Facebook's early platform3. The exact signals that ChatGPT will launch a third-party platform within six months4. Why you have six months (not years) to make your platform bet5. Why companies that don't integrate with ChatGPT will lose to competitors that do6. How Zynga grew to $1B by betting on Facebook's platform early (before it was obvious)7. Why so few companies are actually doing what they need to be doing right now—Brought to you by:DX—The developer intelligence platform designed by leading researchers: http://getdx.com/lennyBasecamp—The famously straightforward project management system from 37signals: https://www.basecamp.com/lennyMiro—A collaborative visual platform where your best work comes to life: https://miro.com/lenny—Transcript: https://www.lennysnewsletter.com/p/why-chatgpt-will-be-the-next-big-growth-channel-brian-balfour—My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/170294620/my-biggest-takeaways-from-this-conversation—Where to find Brian Balfour:• X: https://twitter.com/bbalfour• LinkedIn: https://www.linkedin.com/in/bbalfour/• Website: https://brianbalfour.com/• Substack: https://blog.brianbalfour.com/• Podcast: https://www.reforge.com/podcast/unsolicited-feedback—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Welcome back, Brian!(04:13) The changing landscape of product growth(05:09) The importance of distribution(08:14) The role of new distribution platforms(09:45) The four-step cycle of distribution platforms(17:38) Examples of platform cycles(30:01) The rise of ChatGPT(44:47) The future of AI agents(46:01) Preferred partners and platform credibility(47:18) Monetization mechanisms and free tiers(48:14) Betting strategies for startups(01:04:34) Adopting AI tools: challenges and strategies(01:08:41) The importance of hard constraints(01:14:23) Effective AI adoption in companies(01:19:05) Lightning round and final thoughts—Referenced:• The Next Great Distribution Shift: https://blog.brianbalfour.com/p/the-next-great-distribution-shift• Brian Balfour: 10 lessons on career, growth, and life: https://www.lennysnewsletter.com/p/brian-balfour-10-lessons-on-career• This Week #9: Breaking into growth, leading with influence, and (not) stepping on toes: https://www.lennysnewsletter.com/p/this-week-9-breaking-into-growth• Distribution vs. Innovation: https://a16z.com/distribution-vs-innovation/• On Platform Shifts and AI: https://caseyaccidental.com/on-platform-shifts-and-ai/• How to sell your ideas and rise within your company | Casey Winters, Eventbrite: https://www.lennysnewsletter.com/p/how-to-sell-your-ideas-and-rise-within• Thinking beyond frameworks | Casey Winters (Pinterest, Eventbrite, Airbnb, Tinder, Canva, Reddit, Grubhub): https://www.lennysnewsletter.com/p/thinking-beyond-frameworks-casey• ChatGPT: https://chatgpt.com/• Claude: https://claude.ai/• Gemini: https://gemini.google.com/• Vine: https://en.wikipedia.org/wiki/Vine_(service)• Periscope: https://en.wikipedia.org/wiki/Periscope_(service)• Myspace: https://en.wikipedia.org/wiki/Myspace• Friendster: https://en.wikipedia.org/wiki/Friendster• AltaVista: https://en.wikipedia.org/wiki/AltaVista• Lycos: https://www.lycos.com/• HubSpot: https://www.hubspot.com/• Zynga: https://www.zynga.com/• TBPN: https://www.tbpn.com/• Deedy Das on LinkedIn: https://www.linkedin.com/in/debarghyadas/• ChatGPT's product retention curves are a product manager's wet dream: https://www.linkedin.com/posts/debarghyadas_chatgpts-product-retention-curves-are-a-activity-7338384752393035776-ice1/• Windsurf: https://windsurf.com/• Building a magical AI code editor used by over 1 million developers in four months: The untold story of Windsurf | Varun Mohan (co-founder and CEO): https://www.lennysnewsletter.com/p/the-untold-story-of-windsurf-varun-mohan• Anthropic's CPO on what comes next | Mike Krieger (co-founder of Instagram): https://www.lennysnewsletter.com/p/anthropics-cpo-heres-what-comes-next• Udemy: https://www.udemy.com/• Cursor: https://cursor.com/• The rise of Cursor: The $300M ARR AI tool that engineers can't stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell• Notion: https://www.notion.com/• Airtable: https://www.airtable.com/• Monday: monday.com• Sierra: http://sierra.ai• He saved OpenAI, invented the “Like” button, and built Google Maps: Bret Taylor on the future of careers, coding, agents, and more: https://www.lennysnewsletter.com/p/he-saved-openai-bret-taylor• Introducing ChatGPT agent: bridging research and action: https://openai.com/index/introducing-chatgpt-agent/• 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• Marc Andreessen on Why Optimism Is the Safest Bet: https://nymag.com/marc-andressen-2014-10-20/• Reforge: https://www.reforge.com• Reforge Insights: https://www.reforge.com/insights• Shopify: https://www.shopify.com/• 25 proven tactics to accelerate AI adoption at your company: https://www.lennysnewsletter.com/p/25-proven-tactics-to-accelerate-ai• Clouded Judgement: https://cloudedjudgement.substack.com/• NFX: https://www.nfx.com/news• James Currier: https://www.nfx.com/team/james-currier• Hallway Chat: https://www.hallwaychat.co/• Bryan Johnson on LinkedIn: https://www.linkedin.com/in/bryanrjohnson/• Silicon Valley on HBO: https://www.hbomax.com/shows/silicon-valley/b4583939-e39f-4b5c-822d-5b6cc186172d• Stick: https://tv.apple.com/us/show/stick/umc.cmc.52w04zy67tiv11p8xvbc57wmc• Ergonofis standing desks: https://ergonofis.com/en-us/collections/standing-desks• Coping with the loss of a child and protecting your time | Brian Balfour (father of 2, CEO and founder Reforge, venture partner): https://www.startupdadpod.com/coping-with-the-loss-of-a-child-and-protecting-your-time-brian-balfour-father-of-2-ceo-and-found/—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Matt LeMay spent 13 years as a music critic at Pitchfork before becoming one of product management's most influential voices. He's consulted with companies from startups to Fortune 500s and authored two essential PM books, including Impact-First Product Teams. After watching countless product teams get laid off despite “doing everything right,” he discovered a harsh truth: most PMs are optimizing for the wrong things.In this conversation, you'll learn:1. The one question that predicts if your team will survive the next layoffs (and why most teams can't answer it)2. Why following product “best practices” perfectly can actually accelerate your path to unemployment3. The “low-impact PM death spiral”—how teams accidentally make themselves irrelevant4. How to push back on executives without saying “no” (the options, plus a recommendation framework)5. The counterintuitive reason why the happiest PMs are also the most commercially minded6. The Liz Phair review that made Matt an internet villain for 22 years—and what it taught him about product management—Brought to you by:Enterpret—Transform customer feedback into product growth: https://enterpret.com/lennyPragmatic Institute—Industry‑recognized product, marketing, and AI training & certifications: https://pragmaticinstitute.com/lennyClaude.ai—The AI for problem solvers and enterprise: http://claude.ai/—Transcript: https://www.lennysnewsletter.com/p/the-one-question-that-saves-product-careers-matt-lemay—My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/168109376/my-biggest-takeaways-from-this-conversation—Where to find Matt LeMay:• Instagram: https://www.instagram.com/mttlmy• LinkedIn: https://www.linkedin.com/in/mattlemay/• Website: https://mattlemay.com/—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Matt LeMay(04:23) Matt's background and transition to product management(06:47) The goal of Matt's new book(12:00) How to stress test your thinking as a PM(15:32) Thinking like the CEO(17:33) The role of a product manager(23:36) The low-impact PM death spiral(27:47) Case study: Mailchimp's transition to a platform company(32:53) Radical acceptance(41:24) Embracing constraints in product management(44:23) Steps to become an impact-first product team(49:38) Setting effective goals(01:02:15) Prioritization and impact estimation(01:07:58) Navigating stakeholder management(01:12:35) Summarizing the 3 steps(01:16:36) Lightning round and final thoughts—Referenced:• Pitchfork: https://pitchfork.com/• Daniel Ek's memo: https://newsroom.spotify.com/2023-12-04/an-update-on-december-2023-organizational-changes/• How to create a winning product strategy | Melissa Perri: https://www.lennysnewsletter.com/p/how-to-create-a-winning-product-strategy• Everything you've ever wanted to know about SAFe and the product owner role | Melissa Perri (author, founder of Product Institute): https://www.lennysnewsletter.com/p/product-owners-melissa-perri• Mailchimp: https://mailchimp.com/• Intuit: https://www.intuit.com/• Natalia Williams on LinkedIn: https://www.linkedin.com/in/nataliatwilliams/• The ultimate guide to OKRs | Christina Wodtke (Stanford): https://www.lennysnewsletter.com/p/the-ultimate-guide-to-okrs-christina• Miro: https://miro.com/• Prioritizing: https://www.lennysnewsletter.com/p/prioritizing• Temptation Island on Netflix: https://www.netflix.com/title/81744518• Mark L. Walberg's website: https://markwalbergtv.com/about• Antiques Roadshow on PBS: https://www.pbs.org/wgbh/roadshow/• Milkman amp: https://milkmansound.com/collections/amplifiers/products/the-amp• Matt's review of Liz Phair's self-titled album: https://pitchfork.com/reviews/albums/6255-liz-phair/• Pitchfork Critic Apologizes for Bashing Liz Phair Album; Singer Graciously Accepts: https://variety.com/2019/music/news/pitchfork-critic-apologizes-liz-phair-album-review-zero-score-1203326897/• RedMonk: https://redmonk.com/—Recommended books:• Product Management in Practice: A Practical, Tactical Guide for Your First Day and Every Day After: https://www.amazon.com/Product-Management-Practice-Practical-Tactical/dp/1098119738/r• Impact-First Product Teams: Define Success. Do Work That Matters. Be Indispensable.: https://www.amazon.com/Impact-first-Product-Teams-Success-Indispensable/dp/B0DVH4R3QJ• Escaping the Build Trap: How Effective Product Management Creates Real Value: https://www.amazon.com/Escaping-Build-Trap-Effective-Management/dp/B08B46C8R1/• Radical Focus: Achieving Your Most Important Goals with Objectives and Key Results: https://www.amazon.com/Radical-Focus-Achieving-Important-Objectives/dp/0996006028• The Wisdom of Insecurity: A Message for an Age of Anxiety: https://www.amazon.com/Wisdom-Insecurity-Message-Age-Anxiety/dp/0307741206/—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Nick Turley is Head of ChatGPT, the fastest-growing product in history, with 700 million weekly active users (10% of the world's population). He was part of the original hackathon team that shipped ChatGPT in just 10 days, helped it grow from zero to billions in revenue, and leads product for what may be the most consequential product of our time. We recorded this the day before GPT-5 launched.We discuss:1. The 10-day sprint from deciding to ship ChatGPT to Sam Altman's tweet (and why it was originally called “Chat with GPT-3.5”)2. How they ran a willingness-to-pay Van Westendorp survey in their Discord to decide on the $20/month price point that everyone copied3. The “Is it maximally accelerated?” philosophy that drives OpenAI's insane shipping velocity4. Why ChatGPT's retention curve “smiles”—users leave, then come back months later using it more5. The accidental decisions that changed history, including not having a waitlist6. The impact ChatGPT will have on SEO and product growth7. The counterintuitive reason why shipping unpolished AI features beats waiting for perfection8. Why ChatGPT intentionally shipped with that “ugly” model-chooser dropdown9. How TikTok comments became a primary user research channel early on—Brought to you by:Orkes—The enterprise platform for reliable applications and agentic workflows: https://www.orkes.io/Vanta—Automate compliance. Simplify security: https://vanta.com/lennyPostHog—How developers build successful products: https://posthog.com/lenny—Transcript: https://www.lennysnewsletter.com/p/inside-chatgpt-nick-turley—My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/170411252/my-biggest-takeaways-from-this-conversation—Where to find Nick Turley• X: https://x.com/nickaturley• LinkedIn: https://www.linkedin.com/in/nicholasturley/• Website: https://nickturley.com/—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Nick Turley(04:52) GPT-5 launch(09:13) The vision for ChatGPT and AI assistants(13:52) The early days of ChatGPT(17:14) The success and impact of ChatGPT(20:44) Product development and iteration(23:11) Maximally accelerated: the OpenAI approach(26:17) Retention and user engagement(33:42) The future of chat interfaces(36:31) The evolution of ChatGPT(38:52) Subscription model and pricing strategies(42:10) Enterprise adoption and challenges(44:10) Balancing multiple product lines(52:13) Emergent use cases and user feedback(01:02:15) OpenAI's unique product development approach(01:05:07) The importance of team composition(01:08:50) Balancing speed and quality in AI development(01:14:23) The role of evals in product development(01:16:13) The future of AI-driven content and GPTs(01:21:51) Philosophy and product leadership(01:23:47) Career journey and advice(01:27:49) Lightning round and final thoughts—References: https://www.lennysnewsletter.com/p/inside-chatgpt-nick-turley—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Chip Conley is the founder of Joie de Vivre hotels, the second-largest boutique hotel brand in the world. At age 52, he joined Airbnb as Head of Global Hospitality and Strategy, reporting to CEO Brian Chesky, who was 21 years younger. He earned the title of Airbnb's “Modern Elder” by guiding the young founders on leadership and culture while learning Silicon Valley's tech mindset himself. Today, Chip leads the Modern Elder Academy, the world's first midlife wisdom school, and is the author of best-selling books like Wisdom@Work and Peak. He champions the idea that age and experience are assets—and that midlife can be a launchpad for renewed purpose and impact.In this conversation, we discuss:1. The reality of Brian Chesky in “founder mode”—the good, bad, and stressful2. How Chip went from running 52 boutique hotels to becoming Airbnb's in-house mentor in his 50s3. The “mentor and intern” mindset: how to simultaneously teach others and stay curious like a beginner4. Why AI might actually favor older workers (hint: human wisdom vs. artificial intelligence)5. His framework for navigating midlife transitions and finding meaning after 406. Specific tactics for older professionals to thrive in tech companies7. Surprising data that midlife is often the happiest time of life—and how to leverage your 40s, 50s, and beyond8. Chip's formula for managing anxiety and fear (and how to regain control when worry strikes)—Brought to you by:Great Question—Empower everyone to run great research: https://www.greatquestion.com/lennyVanta—Automate compliance. Simplify security: https://vanta.com/lennyCoda—The all-in-one collaborative workspace: https://coda.io/lenny—Transcript: https://www.lennysnewsletter.com/p/chip-conley —My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/168435278/my-biggest-takeaways-from-this-conversation—Where to find Chip Conley:• LinkedIn: https://www.linkedin.com/in/chipconleysf/• Website: https://chipconley.com/• Modern Elder Academy: https://www.meawisdom.com/• Podcast: https://www.meawisdom.com/podcast/—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Chip Conley(04:09) Chip's journey with Airbnb(10:35) Insights on working with Brian Chesky(19:56) The value of intergenerational collaboration(25:57) Addressing ageism in tech(41:33) Chip's early career and founding Joie de Vivre(43:54) A life-changing near-death experience(46:39) The importance of company culture(55:57) The Modern Elder Academy(59:21) The upside of aging(01:06:53) AI in daily life(01:09:14) Lightning round and final thoughts—Referenced:• Brian Chesky on LinkedIn: https://www.linkedin.com/in/brianchesky/• Brian Chesky's new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach• Natalie Tucci on LinkedIn: https://www.linkedin.com/in/natalietuccishoff/• Laura Modi on LinkedIn: https://www.linkedin.com/in/laurahughes6/• How to build a cult-like brand | Laura Modi (Bobbie): https://www.lennysnewsletter.com/p/from-growth-to-slowth-the-making• George Tenet: https://en.wikipedia.org/wiki/George_Tenet• Joie de Vivre Hospitality: https://www.hyatt.com/jdv-by-hyatt/en-US• Fest300: https://en.wikipedia.org/wiki/Fest300• John Q. Smith on LinkedIn: https://www.linkedin.com/in/johnqsmith/•Will A.I. Replace New Hires or Middle Managers?: https://www.nytimes.com/2025/07/07/business/ai-job-cuts.html• Burning Man: https://burningman.org/• Sheryl Sandberg on LinkedIn: https://www.linkedin.com/in/sheryl-sandberg-5126652/• Bill Graham: https://en.wikipedia.org/wiki/Bill_Graham_(promoter)• Maslow's hierarchy: https://en.wikipedia.org/wiki/Maslow%27s_hierarchy_of_needs• Measuring what makes life worthwhile: https://www.ted.com/talks/chip_conley_measuring_what_makes_life_worthwhile• Jonathan Mildenhall on LinkedIn: https://www.linkedin.com/in/mildenhall/• Becca Levy's website: https://becca-levy.com/• Kabuki Springs & Spa: https://kabukisprings.com/• How positive age beliefs can support positive health outcomes with Becca Levy, PhD: https://www.ama-assn.org/delivering-care/population-care/how-positive-age-beliefs-can-support-positive-health-outcomes-becca• The U-shape of Happiness Across the Life Course: Expanding the Discussion: https://pmc.ncbi.nlm.nih.gov/articles/PMC7529452/• The Midlife Unraveling: https://brenebrown.com/articles/2018/05/24/the-midlife-unraveling/• Four Seasons: https://www.fourseasons.com/• Blue Zones: https://www.bluezones.com/• The Esalen Institute: https://www.esalen.org/• Wisdom Well blog: https://www.meawisdom.com/wisdom-well/• Elizabeth Gilbert TED Talk: Your elusive creative genius: https://www.ted.com/talks/elizabeth_gilbert_your_elusive_creative_genius• Ted Lasso on AppleTV+: https://tv.apple.com/us/show/ted-lasso/umc.cmc.vtoh0mn0xn7t3c643xqonfzy• I'll Push You: https://www.illpushyou.com/• Vuori shorts: https://vuoriclothing.com/collections/shorts• Fly Ranch: https://flyranch.burningman.org/—Recommended books:• Wisdom at Work: The Making of a Modern Elder: https://www.amazon.com/Wisdom-Work-Making-Modern-Elder/dp/0525572902• Range: Why Generalists Triumph in a Specialized World: https://www.amazon.com/Range-Generalists-Triumph-Specialized-World/dp/0735214484• Peak: How Great Companies Get Their Mojo from Maslow: https://www.amazon.com/Peak-Great-Companies-Their-Maslow/dp/0787988618• Learning to Love Midlife: 12 Reasons Why Life Gets Better with Age: https://www.amazon.com/Learning-Love-Midlife-Reasons-Better/dp/0316567027• Man's Search for Meaning: https://www.amazon.com/Mans-Search-Meaning-Viktor-Frankl/dp/0807060100/• Emotional Equations: Simple Steps for Creating Happiness + Success in Business + Life: https://www.amazon.com/Emotional-Equations-Creating-Happiness-Business/dp/1451607261/• Big Magic: Creative Living Beyond Fear: https://www.amazon.com/Big-Magic-Creative-Living-Beyond/dp/1594634726—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Bret Taylor's legendary career includes being CTO of Meta, co-CEO of Salesforce, chairman of the board at OpenAI (yes, during that drama), co-creating both Google Maps and the Like button, and founding three companies. Today he's the founder and CEO of Sierra, an AI agent company transforming customer service. He's one of the few people I've met who's been wildly successful at every level—from engineer to C-suite executive to founder—and across almost every discipline, including PM, engineer, CTO, COO, CPO, CEO, and board member.In this conversation, you'll learn:1. The brutal product review that nearly ended his Google career—and how that failure led to creating Google Maps2. The question Sheryl Sandberg taught him to ask every morning (“What's the most impactful thing I can do today?”) that transformed how he approached every role3. The three AI market segments that matter4. Why AI agents will replace SaaS products5. His framework for knowing whose advice to actually listen to—and how that came in handy during the OpenAI board drama6. The counterintuitive go-to-market strategy most AI startups get wrong7. Sierra's outcome-based pricing model that's transforming how enterprise software is sold (and why every SaaS company should adopt it)8. What he's teaching his kids about AI that every parent should know—Brought to you by:CodeRabbit—Cut code review time and bugs in half. Instantly: https://coderabbit.link/lennyBasecamp—The famously straightforward project management system from 37signals: https://www.basecamp.com/lennyVanta—Automate compliance. Simplify security: https://vanta.com/lenny—Where to find Bret Taylor:• X: https://x.com/btaylor• LinkedIn: https://www.linkedin.com/in/brettaylor/—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Bret Taylor(04:10) Bret's early career and first major mistake(08:24) The birth of Google Maps(11:57) Lessons from FriendFeed and the importance of honest feedback(31:30) The future of coding and AI's role(45:26) Preparing the next generation for an AI-driven world(48:46) AI in education(52:05) Business strategies in the AI market(01:04:38) Outcome-based pricing in AI(01:09:15) Productivity gains and AI(01:17:35) Go-to-market strategies for AI products(01:21:49) Lightning round and final thoughts—Referenced:• Marissa Mayer on LinkedIn: https://www.linkedin.com/in/marissamayer/• “Lazy Sunday”—SNL: https://www.youtube.com/watch?v=sRhTeaa_B98• Quip: https://quip.com/• Sierra: https://sierra.ai/• FriendFeed: https://en.wikipedia.org/wiki/FriendFeed• Sheryl Sandberg on LinkedIn: https://www.linkedin.com/in/sheryl-sandberg-5126652/• Jim Norris on LinkedIn: https://www.linkedin.com/in/halfspin/• Paul Buchheit on X: https://x.com/paultoo• Sanjeev Singh on LinkedIn: https://www.linkedin.com/in/sanjeev-singh-20a1b72/• Barack Obama: https://www.obamalibrary.gov/obamas/president-barack-obama• Oprah Winfrey: https://en.wikipedia.org/wiki/Oprah_Winfrey• Ashton Kutcher: https://en.wikipedia.org/wiki/Ashton_Kutcher• PayPal Mafia: https://en.wikipedia.org/wiki/PayPal_Mafia• Sam Altman on X: https://x.com/sama• Warren Buffett on X: https://x.com/warrenbuffett• Unix: https://en.wikipedia.org/wiki/Unix• Fortran: https://en.wikipedia.org/wiki/Fortran• C: https://en.wikipedia.org/wiki/C_(programming_language)• Python: https://www.python.org/• Perl: https://www.perl.org/• Rust: https://www.rust-lang.org/• Eleven Labs: https://elevenlabs.io/• 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• Confluent: https://www.confluent.io/• Databricks: https://www.databricks.com/• Snowflake: https://www.snowflake.com• Harvey: https://www.harvey.ai/• Behind the founder: Marc Benioff: https://www.lennysnewsletter.com/p/behind-the-founder-marc-benioff• Larry Summers's website: https://larrysummers.com/• AutoCAD: https://www.autodesk.com/products/autocad/overview• Revit: https://www.autodesk.com/products/revit/• The art and science of pricing | Madhavan Ramanujam (Monetizing Innovation, Simon-Kucher): https://www.amazon.com/Monetizing-Innovation-Companies-Design-Product/dp/1119240867• Pricing your AI product: Lessons from 400+ companies and 50 unicorns | Madhavan Ramanujam: https://lenny.substack.com/p/pricing-and-scaling-your-ai-product-madhavan-ramanujam• Cursor: https://cursor.com/• CodeX: https://openai.com/codex/• Claude Code: https://www.anthropic.com/claude-code• The rise of Cursor: The $300M ARR AI tool that engineers can't stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell• DirecTV: https://www.directv.com/• SiriusXM: https://www.siriusxm.com/• Wayfair: https://www.wayfair.com/• Akai: https://www.akaipro.com/• Chubbies Shorts: https://www.chubbiesshorts.com/• Weight Watchers: https://www.weightwatchers.com/• CLEAR: https://www.clearme.com/• Stripe: https://stripe.com/• Building product at Stripe: craft, metrics, and customer obsession | Jeff Weinstein (Product lead): https://www.lennysnewsletter.com/p/building-product-at-stripe-jeff-weinstein• Twilio: https://www.twilio.com/• ServiceNow: https://www.servicenow.com/• Adobe: https://www.adobe.com/• Jobs to be done: https://jobs-to-be-done.com/jobs-to-be-done-a-framework-for-customer-needs-c883cbf61c90• The ultimate guide to JTBD | Bob Moesta (co-creator of the framework): https://www.lennysnewsletter.com/p/the-ultimate-guide-to-jtbd-bob-moesta• Inception: https://www.imdb.com/title/tt1375666/• Alan Kay's quote: https://www.brainyquote.com/quotes/alan_kay_100831• Jobs at Sierra: https://sierra.ai/careers—Recommended books:• Monetizing Innovation: How Smart Companies Design the Product Around the Price: https://www.amazon.com/Monetizing-Innovation-Companies-Design-Product/dp/1119240867• Competing Against Luck: The Story of Innovation and Customer Choice: https://www.amazon.com/Competing-Against-Luck-Innovation-Customer/dp/0062435612• Endurance: Shackleton's Incredible Voyage: https://www.amazon.com/Endurance-Shackletons-Incredible-Alfred-Lansing/dp/0465062881—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Madhavan Ramanujam is the world's foremost expert on pricing and monetization strategy. As managing partner at Simon-Kucher, he helped over 250 companies, including 30 unicorns, architect their pricing strategies. He's the author of the definitive book on pricing, Monetizing Innovation. Now he's back with a sequel, Scaling Innovation, which reveals how to build enduring businesses by dominating both market share and wallet share. He recently left Simon-Kucher to launch his own fund, 49 Palms, focused on helping early-stage AI companies.In this conversation, we discuss:1. The 2x2 framework that identifies your optimal pricing model2. Why AI companies can capture 25% to 50% of value created, vs. 10% to 20% for traditional SaaS products3. Why popular AI coding tools may have already doomed themselves with underpricing4. The “give-and-get” framework top negotiators use to extract maximum value from every deal5. The negotiation strategy that helped one founder 4x their deal size overnight6. How to frame POCs as “business case creation” instead of technical demos (and why this changes everything)7. Why AI companies must get monetization right from day one—not “figure it out later”8. How companies like Intercom's Fin and Sierra pioneered outcome-based pricing (charging $0.99 per AI resolution)9. The single question that reveals if your pricing is too complex—Brought to you by:Enterpret—Transform customer feedback into product growth: https://enterpret.com/lennyDX—A platform for measuring and improving developer productivity: https://getdx.com/lennyPersona—A global leader in digital identity verification: https://withpersona.com/lenny—Transcript: https://www.lennysnewsletter.com/p/pricing-and-scaling-your-ai-product-madhavan-ramanujam— My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/168109183/my-biggest-takeaways-from-this-conversation—Where to find Madhavan Ramanujam:• X: https://x.com/madhavansf• LinkedIn: https://www.linkedin.com/in/madhavansf/• Promo email for Scaling Innovation: promo@49palmsvc.com — If you're purchasing more than five copies, send a screenshot of your receipt to enter Madhavan's exclusive bundle raffle.—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Madhavan and his work(04:30) The core thesis of Scaling Innovation(09:20) Common traps founders fall into(12:06) Beautifully simple pricing(15:00) Mastering negotiations(26:51) Other strategies for effective pricing and monetization(27:35) How AI pricing is different(31:33) Handling POCs(36:25) The importance of mastering monetization(38:58) Choosing the right AI pricing model(43:13) Current trends in AI pricing(44:48) Strategizing for outcome-based models(50:23) Packaging strategies for scaling(51:37) Adapting pricing strategies over time(53:40) Key axioms for pricing success(58:00) Takeaways for founders(01:01:33) Lightning round and final thoughts—Referenced:• The art and science of pricing | Madhavan Ramanujam (Monetizing Innovation, Simon-Kucher): https://www.lennysnewsletter.com/p/the-art-and-science-of-pricing-madhavan• Cursor: https://www.cursor.com/• The rise of Cursor: The $300M ARR AI tool that engineers can't stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell• Sierra Finn: http://www.sierrafinn.com/• Chargeflow: https://www.chargeflow.io/• GitHub: https://github.com/• Intercom: https://www.intercom.com/• Warren Buffett's quote: https://www.goodreads.com/quotes/11478913-if-you-ve-got-the-power-to-raise-prices-without-losing• Sierra: https://sierra.ai/• Clay Bavor on LinkedIn: https://www.linkedin.com/in/claybavor/• Mission: Impossible—The Final Reckoning: https://www.imdb.com/title/tt9603208/• Delphi: https://www.delphi.ai/• Dara Ladjevardian on LinkedIn: https://www.linkedin.com/in/dara-ladjevardian/• Sam Spelsberg on LinkedIn: https://www.linkedin.com/in/samuel-spelsberg/• Lennybot: https://www.lennybot.com/• Granola: https://www.granola.ai/• Simon-Kucher: https://www.simon-kucher.com/• Josh Bloom on LinkedIn: https://www.linkedin.com/in/joshuabloompricingconsulting/—Recommended books:• Monetizing Innovation: How Smart Companies Design the Product Around the Price: https://www.amazon.com/Monetizing-Innovation-Companies-Design-Product/dp/1119240867• Scaling Innovation: How Smart Companies Architect Profitable Growth: https://www.amazon.com/dp/1119633060• Business Model Generation: A Handbook for Visionaries, Game Changers, and Challengers: https://www.amazon.com/Business-Model-Generation-Visionaries-Challengers/dp/0470876417• Thinking Fast and Slow: https://www.amazon.com/Thinking-Fast-Slow-Daniel-Kahneman/dp/0374533555/• Contagious: Why Things Catch On: https://www.amazon.com/Contagious-Things-Catch-Jonah-Berger/dp/1451686587/—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Benjamin Mann is a co-founder of Anthropic, an AI startup dedicated to building aligned, safety-first AI systems. Prior to Anthropic, Ben was one of the architects of GPT-3 at OpenAI. He left OpenAI driven by the mission to ensure that AI benefits humanity. In this episode, Ben opens up about the accelerating progress in AI and the urgent need to steer it responsibly.In this conversation, we discuss:1. The inside story of leaving OpenAI with the entire safety team to start Anthropic2. How Meta's $100M offers reveal the true market price of top AI talent3. Why AI progress is still accelerating (not plateauing), and how most people misjudge the exponential4. Ben's “economic Turing test” for knowing when we've achieved AGI—and why it's likely coming by 2027-20285. Why he believes 20% unemployment is inevitable6. The AI nightmare scenarios that concern him most—and how he believes we can still avoid them7. How focusing on AI safety created Claude's beloved personality8. What three skills he's teaching his kids instead of traditional academics—Brought to you by:Sauce—Turn customer pain into product revenue: https://sauce.app/lennyLucidLink—Real-time cloud storage for teams: https://www.lucidlink.com/lennyFin—The #1 AI agent for customer service: https://fin.ai/lenny—Transcript: https://www.lennysnewsletter.com/p/anthropic-co-founder-benjamin-mann—My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/168107911/my-biggest-takeaways-from-this-conversation—Where to find Ben Mann:• X: https://x.com/8enmann• LinkedIn: https://www.linkedin.com/in/benjamin-mann/• Website: https://benjmann.net/—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Benjamin(04:43) The AI talent war(06:28) AI progress and scaling laws(10:50) Defining AGI and the economic Turing test(12:26) The impact of AI on jobs(17:45) Preparing for an AI future(24:05) Founding Anthropic(27:06) Balancing AI safety and progress(29:10) Constitutional AI and model alignment(34:21) The importance of AI safety(43:40) The risks of autonomous agents(45:40) Forecasting superintelligence(48:36) How hard is it to align AI?(53:19) Reinforcement learning from AI feedback (RLAIF)(57:03) AI's biggest bottlenecks(01:00:11) Personal reflections on responsibilities(01:02:36) Anthropic's growth and innovations(01:07:48) Lightning round and final thoughts—Referenced:• Dario Amodei on LinkedIn: https://www.linkedin.com/in/dario-amodei-3934934/• Anthropic CEO: AI Could Wipe Out 50% of Entry-Level White Collar Jobs: https://www.marketingaiinstitute.com/blog/dario-amodei-ai-entry-level-jobs• Alexa+: https://www.amazon.com/dp/B0DCCNHWV5• Azure: https://azure.microsoft.com/• Sam Altman on X: https://x.com/sama• Opus 3: https://www.anthropic.com/news/claude-3-family• Claude's Constitution: https://www.anthropic.com/news/claudes-constitution• Greg Brockman on X: https://x.com/gdb• Anthropic's Responsible Scaling Policy: https://www.anthropic.com/news/anthropics-responsible-scaling-policy• Agentic Misalignment: How LLMs could be insider threats: https://www.anthropic.com/research/agentic-misalignment• Anthropic's CPO on what comes next | Mike Krieger (co-founder of Instagram): https://www.lennysnewsletter.com/p/anthropics-cpo-heres-what-comes-next• AI prompt engineering in 2025: What works and what doesn't | Sander Schulhoff (Learn Prompting, HackAPrompt): https://www.lennysnewsletter.com/p/ai-prompt-engineering-in-2025-sander-schulhoff• Unitree: https://www.unitree.com/• Arthur C. Clarke: https://en.wikipedia.org/wiki/Arthur_C._Clarke• How Reinforcement Learning from AI Feedback Works: https://www.assemblyai.com/blog/how-reinforcement-learning-from-ai-feedback-works• RLHF: https://en.wikipedia.org/wiki/Reinforcement_learning_from_human_feedback• Jared Kaplan on LinkedIn: https://www.linkedin.com/in/jared-kaplan-645843213/• Moore's law: https://en.wikipedia.org/wiki/Moore%27s_law• Machine Intelligence Research Institute: https://intelligence.org/• Raph Lee on LinkedIn: https://www.linkedin.com/in/raphaeltlee/• “The Last Question”: https://en.wikipedia.org/wiki/The_Last_Question• Beth Barnes on LinkedIn: https://www.linkedin.com/in/elizabethmbarnes/• “The Last Question”: https://en.wikipedia.org/wiki/The_Last_Question• Good Strategy, Bad Strategy | Richard Rumelt: https://www.lennysnewsletter.com/p/good-strategy-bad-strategy-richard• Pantheon on Netflix: https://www.netflix.com/title/81937398• Ted Lasso on AppleTV+: https://tv.apple.com/us/show/ted-lasso/umc.cmc.vtoh0mn0xn7t3c643xqonfzy• Kurzgesagt—In a Nutshell: https://www.youtube.com/channel/UCsXVk37bltHxD1rDPwtNM8Q• 5 tips to poop like a champion: https://8enmann.medium.com/5-tips-to-poop-like-a-champion-3292481a9651—Recommended books:• Superintelligence: Paths, Dangers, Strategies: https://www.amazon.com/Superintelligence-Dangers-Strategies-Nick-Bostrom/dp/0198739834• The Hacker and the State: Cyber Attacks and the New Normal of Geopolitics: https://www.amazon.com/Hacker-State-Attacks-Normal-Geopolitics/dp/0674987551• Replacing Guilt: Minding Our Way: https://www.amazon.com/Replacing-Guilt-Minding-Our-Way/dp/B086FTSB3Q• Good Strategy/Bad Strategy: The Difference and Why It Matters: https://www.amazon.com/Good-Strategy-Bad-Difference-Matters/dp/0307886239• The Alignment Problem: Machine Learning and Human Values: https://www.amazon.com/Alignment-Problem-Machine-Learning-Values/dp/0393635821—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Dan Shipper is the co-founder and CEO of Every. With just 15 people, Every publishes a daily AI newsletter, ships multiple AI products, and operates a million-dollar-a-year consulting arm—all while their engineers write virtually zero code. It's the most radical example of AI-first operations, and Dan is a prolific writer who has become a leading voice on how AI is transforming the way we build and work.Learn:1. Why Dan thinks AI won't steal jobs en masse—and may actually reshore many jobs to the U.S.2. The most underrated AI tool for non-programmers3. An inside look at Every's AI-first workflow4. Why every company needs an “AI operations lead”5. How Dan's team uses an arsenal of AI agents (Claude, Codex, “Friday,” “Charlie”) in parallel, treating each AI like a specialist with unique strengths6. Why generalists will thrive in an AI-first world, as rigid job titles blur and everyone becomes a “manager” of AI tools7. Dan's playbook for making any company AI-first—from the CEO setting the example, to hosting internal prompt-sharing sessions, to upskilling teams on AI tools—Brought to you by:CodeRabbit—Cut code review time and bugs in half. Instantly: https://www.coderabbit.ai/DX—A platform for measuring and improving developer productivity: https://getdx.com/lennyPostHog—How developers build successful products: https://posthog.com/lenny—Transcript: https://www.lennysnewsletter.com/p/inside-every-dan-shipper—Where to find Dan Shipper:• X: https://x.com/danshipper• LinkedIn: https://www.linkedin.com/in/danshipper/• Podcast: https://every.to/podcast—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Welcome and introduction(04:04) Hot takes on AI and job reshoring(07:06) The power of Claude Code for non-coders(14:35) The future of AI in business operations(18:45) AI's role in enhancing human skills(22:26) The evolution of AI tools and their applications(25:40) Building an AI-first company(29:50) Innovative AI operations and team dynamics(35:35) Dan's AI stack(41:26) Compounding engineering(48:29) The impact of AI on learning and development(50:10) Accelerating career growth with AI(51:36) Revolutionizing code review and workflow(53:07) The importance of coding knowledge(57:26) Building AI-driven products(01:02:01) Innovative fundraising strategies(01:08:45) Consulting and AI adoption in companies(01:17:01) The allocation economy and future skills(01:20:12) The value of generalists in the AI age(01:24:07) Lightning round and final thoughts—Referenced:• Claude Code: https://www.anthropic.com/claude-code• Gemini CLI: https://blog.google/technology/developers/introducing-gemini-cli-open-source-ai-agent/• Microsoft Copilot: https://copilot.microsoft.com/• Cursor: https://www.cursor.com/• Base44: https://base44.com/• 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• The rise of Cursor: The $300M ARR AI tool that engineers can't stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell• Plato's Argument Against Writing: https://fs.blog/an-old-argument-against-writing/• From ChatGPT to Instagram to Uber: The quiet architect behind the world's most popular products | Peter Deng: https://www.lennysnewsletter.com/p/the-quiet-architect-peter-deng• Granola: https://www.granola.ai/• Tobi Lutke's post on X about context engineering: https://x.com/tobi/status/1935533422589399127• Tobi Lütke's leadership playbook: Playing infinite games, operating from first principles, and maximizing human potential (founder and CEO of Shopify): https://www.lennysnewsletter.com/p/tobi-lutkes-leadership-playbook• Every: https://every.to/• Cora: https://www.cora.computer/• Sparkle: https://makeitsparkle.co/• Spiral: https://spiral.computer/• Lex: https://lex.page/• Nathan Baschez on LinkedIn: https://www.linkedin.com/in/nbashaw/• Kate Lee on LinkedIn: https://www.linkedin.com/in/kate-lee-506768/• Katie Parrott on LinkedIn: https://www.linkedin.com/in/katieparrott/• Animalz: https://www.animalz.co/• Rachel Woods on X: https://x.com/rachel_l_woods• Nityesh Agarwal on LinkedIn: https://www.linkedin.com/in/nityeshaga• Claude Opus 4: https://www.anthropic.com/claude/opus• Codex: https://openai.com/index/introducing-codex/• Superwhisper: https://superwhisper.com/• Wispr Flow: https://wisprflow.ai/• Notion: https://www.notion.com/• Kieran Klaassen on LinkedIn: https://www.linkedin.com/in/kieran-klaassen/• Friday: https://www.friday.run/• Charlie: https://www.gocharlie.ai/product/ai-agents/• Avengers: https://en.wikipedia.org/wiki/Avengers_(Marvel_Cinematic_Universe)• Alex Duffy on LinkedIn: https://www.linkedin.com/in/alex-d/• Danny Aziz on LinkedIn: https://www.linkedin.com/in/dannyaziz/• Dia: https://www.diabrowser.com/• Reid Hoffman's website: https://www.reidhoffman.org/• Starting Line VC: https://www.startingline.vc/• Walleye Capital: https://walleyecapital.com/• At This $10 Billion Hedge Fund, Using AI Just Became Mandatory: https://every.to/podcast/at-this-10-billion-hedge-fund-using-ai-just-became-mandatory• Reflexive AI usage is now a baseline expectation at Shopify: https://x.com/tobi/status/1909251946235437514• Klarna CEO Sebastian Siemiatkowski on Getting AI to Do the Work of 700 Customer Service Reps: https://www.sequoiacap.com/podcast/training-data-sebastian-siemiatkowski/• The Pin Factory: https://www.adamsmithworks.org/pin_factory.html• Deadwood on HBO: https://www.hbo.com/deadwood• Joel Spolsky on X: https://x.com/spolsky• Jason Fried's website: https://world.hey.com/jason• Jason Fried challenges your thinking on fundraising, goals, growth, and more: https://www.lennysnewsletter.com/p/jason-fried-challenges-your-thinking• Sam Harris's website: https://www.samharris.org/• Bill Simmons on X: https://x.com/billsimmons—Recommended books:• War and Peace: https://www.amazon.com/War-Peace-Vintage-Classics-Tolstoy/dp/1400079985• Anna Karenina: https://www.amazon.com/Anna-Karenina-Leo-Tolstoy/dp/0143035002• Playing and Reality: https://www.amazon.com/Playing-Reality-Routledge-Classics-86/dp/0415345464• The Death of Ivan Ilyich: https://www.amazon.com/Death-Ivan-Ilyich-Leo-Tolstoy/dp/1468014315• A Swim in a Pond in the Rain: https://www.amazon.com/Swim-Pond-Rain-Russians-Writing/dp/1984856022• The Master and His Emissary: The Divided Brain and the Making of the Western World: https://www.amazon.com/Master-His-Emissary-Divided-Western/dp/0300245920/—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Jake Knapp and John Zeratsky are the co-creators of the Design Sprint (the famous five-day product innovation process) and authors of the bestselling book Sprint. After decades of working with over 300 startups in the earliest stages, they discovered that most startups fail not because they can't build, but because they build the wrong thing. The very beginning of a startup is your highest-leverage moment, and most teams waste months or years by skipping a few critical early questions. Jake and John developed the Foundation Sprint to help startups validate ideas and compress months of work into just two days.What you'll learn:1. The step-by-step Foundation Sprint process that compresses three or four months of validation into two days—including templates you can use immediately2. Why differentiation is the #1 predictor of startup success (with the 2x2 framework that you can use with your team)3. The three fundamental questions every founder should answer before writing a line of code4. The “note and vote” technique that eliminates groupthink and gets honest answers from your colleagues5. The seven “magic lenses” for choosing between multiple product ideas6. The biggest mistake engineers make when building with AI tools7. The paradox of speed: why “building nothing first” can get you to product-market fit faster—Brought to you by:Brex—The banking solution for startups: https://www.brex.com/product/business-account?ref_code=bmk_dp_brand1H25_ln_new_fsParagon—Ship every SaaS integration your customers want: https://www.useparagon.com/lennyCoda—The all-in-one collaborative workspace: https://coda.io/lenny—Transcript: https://www.lennysnewsletter.com/p/the-foundation-sprint-jake-knapp-and-john-zeratsky—Where to find Jake Knapp:• X: https://twitter.com/jakek• LinkedIn: https://www.linkedin.com/in/jake-knapp/• Website: https://jakeknapp.com/—Where to find John Zeratsky:• X: https://twitter.com/jazer• LinkedIn: https://www.linkedin.com/in/johnzeratsky/• Website: https://johnzeratsky.com/—In this episode, we cover:(00:00) Introduction to Jake Knapp and John Zeratsky(04:41) Origins of the Design Sprint(11:06) The Foundation Sprint process(14:40) Phase one: The basics(16:57) Case study: Latchet(28:50) Phase two: Differentiation(36:24) The importance of differentiation(40:15) Thoughts on price differentiation(43:37) Case study: Mellow(46:04) Custom differentiators(49:30) The mini manifesto(52:02) Phase three: Approach to the project(54:50) Magic lenses activity(01:02:39) Prototyping and testing(01:10:00) Real-world examples and success stories(01:15:15) Motivation behind The Foundation Sprint(01:17:15) The outcome of the sprint: The founding hypothesis(01:19:28) The Design Sprint(01:28:19) The role of AI in prototyping(01:36:50) Final thoughts and resources—Referenced:• Introducing the Foundation Sprint: From the creators of the Design Sprint: https://www.lennysnewsletter.com/p/introducing-the-foundation-sprint• Making time for what matters | Jake Knapp and John Zeratsky (authors of Sprint and Make Time, co-founders of Character Capital): https://www.lennysnewsletter.com/p/making-time-for-what-matters-jake• Eli Blee-Goldman on LinkedIn: https://www.linkedin.com/in/eli-blee-goldman/• Character Capital: https://www.character.vc/• Character Labs: https://www.character.vc/labs• Etsy: https://www.etsy.com/• Shopify: https://www.shopify.com/• 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• Sonos: https://www.sonos.com/• Vercel: https://vercel.com/• Windsurf: https://windsurf.com/• April Dunford on product positioning, segmentation, and optimizing your sales process: https://www.lennysnewsletter.com/p/april-dunford-on-product-positioning• Positioning: https://www.lennysnewsletter.com/p/positioning• 10 things we know to be true: https://about.google/company-info/philosophy/• Gandalf: https://en.wikipedia.org/wiki/Gandalf• Frodo: https://en.wikipedia.org/wiki/Frodo_Baggins• Mordor: https://en.wikipedia.org/wiki/Mordor• 35 years of product design wisdom from Apple, Disney, Pinterest, and beyond | Bob Baxley: https://www.lennysnewsletter.com/p/35-years-of-product-design-wisdom-bob-baxley• The Primal Mark: How the Beginning Shapes the End in the Development of Creative Ideas: https://www.gsb.stanford.edu/faculty-research/publications/primal-mark-how-beginning-shapes-end-development-creative-ideas• Base44: https://base44.com/• 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• Google Meet: https://meet.google.com/• Blue Bottle Coffee: https://bluebottlecoffee.com• Reclaim: https://reclaim.ai/• The official Foundation Sprint + Design Sprint template: https://www.character.vc/miro-template• Rippling: https://www.rippling.com/• Latchet: https://latchet.com/• Mellow: http://getmellow.com/• AxionOrbital: https://axionorbital.space/—Recommended books:• Sprint: How to Solve Big Problems and Test New Ideas in Just Five Days: https://www.amazon.com/Sprint-audiobook/dp/B019R2DQIY• Make Time: How to Focus on What Matters Every Day: https://www.amazon.com/Make-Time-Focus-Matters-Every/dp/0525572422• Click: How to Make What People Want: https://www.amazon.com/Click-Make-What-People-Want/dp/1668072114Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Maor Shlomo is the founder of Base44, an AI-powered app builder that he bootstrapped to an over $80 million acquisition by Wix in just six months. As a solo founder (with severe ADHD), he hit $1 million ARR just three weeks after launch and grew the product to more than 400,000 users, all while navigating two wars in Israel and never raising a dollar of outside funding.What you'll learn:1. The growth playbook that took Base44 from three friends to 400,000 users without spending any money on marketing2. How he hasn't written a single line of front-end code in three months—and how to structure your code repository to make it easier for AI to write your code3. His AI productivity stack that allowed him to compete against heavily funded competitors4. Why being a solo founder in AI might be the ultimate advantage (and the wedding story that almost killed the business)5. The story of signing the $80M acquisition deal while war broke out with Iran6. How to identify when to sell vs. stay independent (and why Maor chose acquisition despite being highly profitable)7. The counterintuitive product decision that tripled activation by removing a “helpful” feature8. How building in public on LinkedIn drove more growth than any paid channel—Brought to you by:Sauce—Turn customer pain into product revenue: https://sauce.app/lennyDscout—The UX platform to capture insights at every stage: from ideation to production: https://www.dscout.com/Contentsquare—Create better digital experiences: https://contentsquare.com/lenny/—Transcript: ⁠https://www.lennysnewsletter.com/p/the-base44-bootstrapped-startup-success-story-maor-shlomo⁠—My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/167384119/my-biggest-takeaways-from-this-conversation—Where to find Maor Shlomo:• X: https://x.com/ms_base44• LinkedIn: https://www.linkedin.com/in/maor-shlomo-1088b4144/—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Maor and Base44(08:16) The origin story: how Base44 came to be(14:55) Bootstrapping and solo founding: challenges and insights(22:52) Productivity hacks and tech stack for solo founders(27:23) How to get started using Base44(28:47) Thoughts on raising money(34:05) Distribution in the age of AI(36:09) Ambition and goals(40:05) Growth strategies: from first users to thousands(51:32) Building in public(57:42) The solo founder journey(01:00:23) Community support(01:03:23) Hackathons and partnerships(01:06:42) The importance of velocity in product development(01:08:20) Technical stack and infrastructure insights(01:15:24) Activation lessons(01:18:19) The acquisition journey with Wix(01:25:14) Final thoughts and advice for founders—Referenced:• Base44: https://base44.com/• Retool: https://retool.com/• Tzofim: https://www.israelscouts.org/• Y Combinator: https://www.ycombinator.com/• RescueTime: https://www.rescuetime.com/• Cursor: https://www.cursor.com/• Wix: https://www.wix.com/• The rise of Cursor: The $300M ARR AI tool that engineers can't stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell• Building Lovable: $10M ARR in 60 days with 15 people | Anton Osika (CEO and co-founder): https://www.lennysnewsletter.com/p/building-lovable-anton-osika• Inside Bolt: From near-death to ~$40m ARR in 5 months—one of the fastest-growing products in history | Eric Simons (founder and CEO of StackBlitz): https://www.lennysnewsletter.com/p/inside-bolt-eric-simons• Behind the product: Replit | Amjad Masad (co-founder and CEO): https://www.lennysnewsletter.com/p/behind-the-product-replit-amjad-masad• Everyone's an engineer now: Inside v0's mission to create a hundred million builders | Guillermo Rauch (founder and CEO of Vercel, creators of v0 and Next.js): https://www.lennysnewsletter.com/p/everyones-an-engineer-now-guillermo-rauch• Snowflake: https://www.snowflake.com• Yoav Orlev on LinkedIn: https://www.linkedin.com/in/yoav-orlev-4a044b72• WhatsApp: https://www.whatsapp.com/• Amazon: https://www.amazon.com/• Google: https://about.google/• MongoDB: https://www.mongodb.com/• Deloitte: https://www.deloitte.com/• Render: Render.com• Claude 4: https://www.anthropic.com/news/claude-4• Gemini: https://gemini.google.com/app• Cloudflare: https://www.cloudflare.com/—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Andrew Wilkinson is the co‑founder of Tiny, a holding company that quietly owns more than three dozen profitable internet and consumer brands, including Dribbble and the AeroPress coffee maker. Starting as a teenage barista and web designer, he's created a portfolio approaching $300 million in yearly sales (and he was personally worth over $1 billion at one point)—all without ever raising venture capital.In this conversation, you'll learn:1. The “fish where the fish are” framework for spotting high‑margin niches no one else notices2. The exact agent stack (Lindy, Replit, Limitless, and more) that supercharges Andrew's day-to-day productivity (and has replaced his assistant)3. How Andrew evaluates companies in less than 15 minutes using Buffett‑style moats and “lazy leadership”4. Telltale signs you should shut down (or never start) that startup idea5. His journey from crippling anxiety to clarity through SSRIs and ADHD medication6. His prediction that most knowledge work will be automated—and the skills to teach your kids now—Brought to you by:Sauce—Turn customer pain into product revenueEnterpret—Transform customer feedback into product growthMiro—A collaborative visual platform where your best work comes to life—Where to find Andrew Wilkinson:• X: https://x.com/awilkinson• LinkedIn: https://www.linkedin.com/in/awilkinson/—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Andrew Wilkinson(04:07) Finding the right business idea(07:18) Avoiding common business pitfalls(11:58) Finding your unfair advantage(17:08) Fish where the fish are(20:08) Why boring is good(25:30) Bootstrapping vs. venture capital(31:20) Lessons from acquiring and managing businesses(36:47) Avoiding people problems(42:39) Leveraging AI in business and life(49:30) The Limitless device(53:13) Job displacement and AI's future impact(58:20) Advice for new grads(01:02:50) Parenting in the age of AI(01:05:26) The pursuit of happiness beyond wealth(01:10:10) Mental health and medication(01:16:45) Lightning round and final thoughts—Referenced:• Andrew's post on X with the Charlie Munger quote: https://x.com/awilkinson/status/1265653805443506182• Metalab: https://www.metalab.com/• Letterboxd: https://letterboxd.com/• AeroPress: https://aeropress.com/• Brian Armstrong on X: https://x.com/brian_armstrong• Warren Buffett's quote: https://quotefancy.com/quote/931119/Warren-Buffett-I-am-a-better-investor-because-I-am-a-businessman-and-a-better-businessman• Flow: https://www.getflow.com/• Instacart: https://www.instacart.com/• Things: https://culturedcode.com/things/• Dustin Moskovitz on LinkedIn: https://www.linkedin.com/in/dmoskov/• Salesforce: https://www.salesforce.com/• Serato: https://serato.com/• Chris Sparling on X: https://x.com/_sparling_• Lindy: https://www.lindy.ai/• Replit: https://replit.com/• Behind the product: Replit | Amjad Masad (co-founder and CEO): https://www.lennysnewsletter.com/p/behind-the-product-replit-amjad-masad• David Ogilvy: https://en.wikipedia.org/wiki/David_Ogilvy_(businessman)• Malcolm Gladwell's website: https://www.gladwellbooks.com/• Inside Bolt: From near-death to ~$40m ARR in 5 months—one of the fastest-growing products in history | Eric Simons (founder and CEO of StackBlitz): https://www.lennysnewsletter.com/p/inside-bolt-eric-simons• Building Lovable: $10M ARR in 60 days with 15 people | Anton Osika (CEO and co-founder): https://www.lennysnewsletter.com/p/building-lovable-anton-osika• Limitless: https://www.limitless.ai/• Perplexity: https://www.perplexity.ai/• Claude: https://claude.ai/• ChatGPT: https://chatgpt.com/• Gemini: https://gemini.google.com/app• William Gibson's quote: https://www.goodreads.com/quotes/681-the-future-is-already-here-it-s-just-not-evenly• Palm Treo: https://en.wikipedia.org/wiki/Palm_Treo• Sam Altman on X: https://x.com/sama• Dario Amodei on X: https://x.com/darioamodei• Anthropic's CPO on what comes next | Mike Krieger (co-founder of Instagram): https://www.lennysnewsletter.com/p/anthropics-cpo-heres-what-comes-next• Challengers on AppleTV+: https://tv.apple.com/us/movie/challengers/umc.cmc.53cuz33n4e74ixj8whccj87oc• Matic vacuum: https://maticrobots.com/• Jerzy Gregorek's quote: https://www.goodreads.com/quotes/8652595-hard-choices-easy-life-easy-choices-hard-life• Tiny: https://www.tiny.com/• Dribbble: https://dribbble.com/—Recommended books:• The Laws of Human Nature: https://www.amazon.com/Laws-Human-Nature-Robert-Greene/dp/0525428143• How to Get Rich: One of the World's Greatest Entrepreneurs Shares His Secrets: https://www.amazon.com/How-Get-Rich-Greatest-Entrepreneurs/dp/1591842719—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

David Placek is the founder of Lexicon Branding, a company that focuses exclusively on the development of brand names for competitive advantage. Lexicon is behind iconic names such as Sonos, Microsoft's Azure, Windsurf, Vercel, Impossible Foods, BlackBerry, Intel's Pentium, Apple's PowerBook, and Swiffer. Over 40 years, David's team has named nearly 4,000 brands and companies, employing over 250 linguists and pioneering naming innovation.What you'll learn:1. The three-step process that generated names like Windsurf and Vercel2. How a name can give you the edge that no marketing budget can buy3. Why you won't “know it when you see it”4. Why Microsoft called Azure “a dumb name” before it became their billion-dollar cloud platform5. Why polarizing opinions are the strongest signal that you've found the right name6. How every letter of the alphabet creates a specific psychological vibration7. The diamond framework: a 4-step process any founder can use to find their perfect name8. Why domain names don't matter anymore in the age of AI—Brought to you by:WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUsStripe—Helping companies of all sizes grow revenueOneSchema—Import CSV data 10x faster—Where to find David Placek:• LinkedIn: https://www.linkedin.com/in/david-placek-05a82/• Website: https://www.lexiconbranding.com—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to David and Lexicon Branding(04:44) The story of Sonos(09:27) The psychology of naming(11:33) The initial resistance to Microsoft's Azure(14:35) The importance of a great brand name(18:11) The three steps of naming: create, invent, implement(28:23) Qualities of great brand name creators(31:24) How long the naming process takes(32:12) The Windsurf case study(36:10) Naming in the AI era(39:37) When to change your name(43:10) The role of linguists(45:54) The power of letters in branding(48:15) The Vercel case study(50:12) The implementation phase(52:52) Client management and market success(55:16) The diamond exercise(01:04:23) Suspending judgment(01:07:31) Polarization and boldness(01:11:01) Domain names(01:12:48) Final thoughts and lightning round—Referenced:• PowerBook: https://en.wikipedia.org/wiki/PowerBook• Pentium: https://en.wikipedia.org/wiki/Pentium• BlackBerry: https://en.wikipedia.org/wiki/BlackBerry• Swiffer: https://www.swiffer.com/• Impossible Burger: https://impossiblefoods.com/• Vercel: https://vercel.com/• Windsurf: https://windsurf.com/• CapCut: https://www.capcut.com/• Azure: https://azure.microsoft.com/• Sonos: https://www.sonos.com/• John MacFarlane on LinkedIn: https://www.linkedin.com/in/john-macfarlane-08a8aa20/• Harry Potter: https://en.wikipedia.org/wiki/Harry_Potter_(film_series)• The Call of the Wild: https://en.wikipedia.org/wiki/The_Call_of_the_Wild• Everyone's an engineer now: Inside v0's mission to create a hundred million builders | Guillermo Rauch (founder and CEO of Vercel, creators of v0 and Next.js): https://www.lennysnewsletter.com/p/everyones-an-engineer-now-guillermo-rauch• Sound symbolism: https://en.wikipedia.org/wiki/Sound_symbolism• Anduril: https://www.anduril.com/• Anthropic: https://www.anthropic.com/• Inside Bolt: From near-death to ~$40m ARR in 5 months—one of the fastest-growing products in history | Eric Simons (founder and CEO of StackBlitz): https://www.lennysnewsletter.com/p/inside-bolt-eric-simons• The rise of Cursor: The $300M ARR AI tool that engineers can't stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell• Building a magical AI code editor used by over 1 million developers in four months: The untold story of Windsurf | Varun Mohan (co-founder and CEO): https://www.lennysnewsletter.com/p/the-untold-story-of-windsurf-varun-mohan• Y Combinator: https://www.ycombinator.com/• Chevrolet Corvette: https://en.wikipedia.org/wiki/Chevrolet_Corvette• Viagra: https://www.viagra.com/• In vino veritas: https://en.wikipedia.org/wiki/In_vino_veritas• Infoseek: https://en.wikipedia.org/wiki/Infoseek• Andy Grove: https://en.wikipedia.org/wiki/Andrew_Grove• Churchill at War on Netflix: https://www.netflix.com/title/81609374• Yellowstone on Prime Video: https://www.amazon.com/Yellowstone-Season-1/dp/B07D7FBB8Z• 1883 on Prime Video: https://www.amazon.com/1883-Season-1/dp/B0B8JTS8QW• 1923 on Paramount+: https://www.paramountplus.com/shows/1923/• Taylor Sheridan on X: https://x.com/taylorSheridan• Hardy fly rods: https://www.hardyfishing.com/collections/fly-rods• T.E. Lawrence quote: https://www.goodreads.com/quotes/11340-all-men-dream-but-not-equally-those-who-dream-by• Lawrence of Arabia: https://www.imdb.com/title/tt0056172/• DreamWorks: https://www.dreamworks.com/—Recommended books:• Thucydides' Melian Dialogue: Commentary, Text, and Vocabulary: https://www.amazon.com/Thucydides-Melian-Dialogue-Commentary-Vocabulary/dp/0692772367• Resilience: Hard-Won Wisdom for Living a Better Life: https://www.amazon.com/Resilience-Hard-Won-Wisdom-Living-Better/dp/054432398X/• Churchill: Walking with Destiny: https://www.amazon.com/Churchill-Walking-Destiny-Andrew-Roberts/dp/1101980990—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Peter Deng has led product teams at OpenAI, Instagram, Uber, Facebook, Airtable, and Oculus and helped build products used by billions—including Facebook's News Feed, the standalone Messenger app, Instagram filters, Uber Reserve, ChatGPT, and more. Currently he's investing in early-stage founders at Felicis. In this episode, Peter dives into his most valuable lessons from building and scaling some of tech's most iconic products and companies.What you'll learn:1. Peter's one‑sentence test for hiring superstars2. Why your product (probably) doesn't matter3. Why you don't need a tech breakthrough to build a huge business4. The five PM archetypes, and how to build a team of Avengers5. Counterintuitive lessons on growing products from 0 to 1, and 1 to 1006. The importance of data flywheels and workflows—Brought to you by:Paragon—Ship every SaaS integration your customers wantPragmatic Institute—Industry‑recognized product, marketing, and AI training and certificationsContentsquare—Create better digital experiences—Where to find Peter Deng:• X: https://x.com/pxd• LinkedIn: https://www.linkedin.com/in/peterxdeng/—In this episode, we cover:(00:00) Introduction to Peter Deng(05:41) AI and AGI insights(11:35) The future of education with AI(16:53) The power of language in leadership(21:01) Building iconic products(36:44) Scaling from zero to 100(41:56) Balancing short- and long-term goals(47:12) Creating a healthy tension in teams(50:02) The five archetypes of product managers(55:39) Primary and secondary archetypes(58:47) Hiring for growth mindset and autonomy(01:15:52) Effective management and communication strategies(01:19:23) Presentation advice and self-advocacy(01:25:50) Balancing craft and practicality in product management(01:30:40) The importance of empathy in design thinking(01:35:45) Career decisions and learning opportunities(01:42:05) Lessons from product failures(01:45:42) Lightning round and final thoughts—Referenced:• OpenAI: https://openai.com/• Artificial general intelligence (AGI): https://en.wikipedia.org/wiki/Artificial_general_intelligence• Head of ChatGPT answers philosophical questions about AI at SXSW 2024 with SignalFire's Josh Constine: https://www.youtube.com/watch?v=mgbgI0R6XCw• Professors Are Using A.I., Too. Now What?: https://www.npr.org/2025/05/21/1252663599/kashmir-hill-ai#:~:text=Now%20What• Herbert H. Clark: https://web.stanford.edu/~clark/• Russian speakers get the blues: https://www.newscientist.com/article/dn11759-russian-speakers-get-the-blues/• Ilya Sutskever (OpenAI Chief Scientist)—Building AGI, Alignment, Future Models, Spies, Microsoft, Taiwan, & Enlightenment: https://www.dwarkesh.com/p/ilya-sutskever• Anthropic's CPO on what comes next | Mike Krieger (co-founder of Instagram): https://www.lennysnewsletter.com/p/anthropics-cpo-heres-what-comes-next• Kevin Systrom on LinkedIn: https://www.linkedin.com/in/kevinsystrom/• Building a magical AI code editor used by over 1 million developers in four months: The untold story of Windsurf | Varun Mohan (co-founder and CEO): https://www.lennysnewsletter.com/p/the-untold-story-of-windsurf-varun-mohan• Microsoft CPO: If you aren't prototyping with AI, you're doing it wrong | Aparna Chennapragada: https://www.lennysnewsletter.com/p/microsoft-cpo-on-ai• The rise of Cursor: The $300M ARR AI tool that engineers can't stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell• Building Lovable: $10M ARR in 60 days with 15 people | Anton Osika (CEO and co-founder): https://www.lennysnewsletter.com/p/building-lovable-anton-osika• Granola: https://www.granola.ai/• Inside Bolt: From near-death to ~$40m ARR in 5 months—one of the fastest-growing products in history | Eric Simons (founder and CEO of StackBlitz): https://www.lennysnewsletter.com/p/inside-bolt-eric-simons• OpenAI's CPO on how AI changes must-have skills, moats, coding, startup playbooks, more | Kevin Weil (CPO at OpenAI, ex-Instagram, Twitter): https://www.lennysnewsletter.com/p/kevin-weil-open-ai• Fidji Simo on LinkedIn: https://www.linkedin.com/in/fidjisimo/• Airtable: https://www.airtable.com/• George Lee on LinkedIn: https://www.linkedin.com/in/geolee/• Andrew Chen on LinkedIn: https://www.linkedin.com/in/andrewchen/• Lauryn Motamedi on LinkedIn: https://www.linkedin.com/in/laurynmotamedi/• Twilio: https://www.twilio.com/• Nick Turley on LinkedIn: https://www.linkedin.com/in/nicholasturley/• Ian Silber on LinkedIn: https://www.linkedin.com/in/iansilber/• Thomas Dimson on LinkedIn: https://www.linkedin.com/in/thomasdimson/• Joey Flynn on LinkedIn: https://www.linkedin.com/in/joey-flynn-8291586b/• Ryan O'Rourke's website: https://www.rourkery.com/• Joanne Jang on LinkedIn: https://www.linkedin.com/in/jangjoanne/• Behind the founder: Marc Benioff: https://www.lennysnewsletter.com/p/behind-the-founder-marc-benioff• Jill Hazelbaker on LinkedIn: https://www.linkedin.com/in/jill-hazelbaker-3aa32422/• Guy Kawasaki's website: https://guykawasaki.com/• Eric Antonow on LinkedIn: https://www.linkedin.com/in/antonow/• Sachin Kansal on LinkedIn: https://www.linkedin.com/in/sachinkansal/• IDEO design thinking: https://designthinking.ideo.com/• The 7 Steps of the Design Thinking Process: https://www.ideou.com/blogs/inspiration/design-thinking-process• Linear's secret to building beloved B2B products | Nan Yu (Head of Product): https://www.lennysnewsletter.com/p/linears-secret-to-building-beloved-b2b-products-nan-yu• Jeff Bezos's quote: https://news.ycombinator.com/item?id=27778175• Friendster: https://en.wikipedia.org/wiki/Friendster• Myspace: https://en.wikipedia.org/wiki/Myspace• How LinkedIn became interesting: The inside story | Tomer Cohen (CPO at LinkedIn): https://www.lennysnewsletter.com/p/how-linkedin-became-interesting-tomer-cohen• “Smile” by Jay-Z: https://www.youtube.com/watch?v=SSumXG5_rs8&list=RDSSumXG5_rs8&start_radio=1• The Wire on HBO: https://www.hbo.com/the-wire• Felicis: https://www.felicis.com/—Recommended books:• Sapiens: A Brief History of Humankind: https://www.amazon.com/Sapiens-Humankind-Yuval-Noah-Harari/dp/0062316095• The Design of Everyday Things: https://www.amazon.com/Design-Everyday-Things-Revised-Expanded/dp/0465050654• The Silk Roads: A New History of the World: https://www.amazon.com/Silk-Roads-New-History-World/dp/1101912375—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Sander Schulhoff is the OG prompt engineer. He created the very first prompt engineering guide on the internet (two months before ChatGPT's release) and recently wrote the most comprehensive study of prompt engineering ever conducted (co-authored with OpenAI, Microsoft, Google, Princeton, and Stanford), analyzing over 1,500 academic papers and covering more than 200 prompting techniques. He also partners with OpenAI to run what was the first and is the largest AI red teaming competition, HackAPrompt, which helps discover the most state-of-the-art prompt injection techniques (i.e. ways to get LLMS to do things it shouldn't). Sander teaches AI red teaming on Maven, advises AI companies on security, and has educated millions of people on the most state-of-the-art prompt engineering techniques.In this episode, you'll learn:1. The 5 most effective prompt engineering techniques2. Why “role prompting” and threatening the AI no longer works—and what to do instead3. The two types of prompt engineering: conversational and product/system prompts4. A primer on prompt injection and AI red teaming—including real jailbreak tactics that are still fooling top models5. Why AI agents and robots will be the next major security threat6. How to get started in AI red teaming and prompt engineering7. Practical defense to put in place for your AI products—Brought to you by:Eppo—Run reliable, impactful experimentsStripe—Helping companies of all sizes grow revenueVanta—Automate compliance. Simplify security—Where to find Sander Schulhoff:• X: https://x.com/sanderschulhoff• LinkedIn: https://www.linkedin.com/in/sander-schulhoff/• Website: https://sanderschulhoff.com/• AI Red Teaming and AI Security Masterclass on Maven: https://bit.ly/44lLSbC• Free Lightning Lesson “How to Secure Your AI System” on 6/24: https://bit.ly/4ld9vZL—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Sander Schulhoff(04:29) The importance of prompt engineering(06:30) Real-world applications and examples(10:54) Basic prompt engineering techniques(23:46) Advanced prompt engineering techniques(29:00) The role of context and additional information(39:24) Ensembling techniques and thought generation(49:48) Conversational techniques for better results(50:46) Introduction to prompt injection(52:27) AI red teaming and competitions(54:23) The growing importance of AI security(01:02:45) Techniques to bypass AI safeguards(01:05:21) Challenges in AI security and future outlook(01:18:33) Misalignment and AI's potential risks(01:25:03) Final thoughts and lightning round—Referenced:• Reid Hoffman's tweet about using AI agents: https://x.com/reidhoffman/status/1930416063616884822• AI Engineer World's Fair: https://www.ai.engineer/• What Is Artificial Social Intelligence?: https://learnprompting.org/blog/asi• Devin: https://devin.ai/• Cursor: https://www.cursor.com/• Inside Devin: The world's first autonomous AI engineer that's set to write 50% of its company's code by end of year | Scott Wu (CEO and co-founder of Cognition): https://www.lennysnewsletter.com/p/inside-devin-scott-wu• The rise of Cursor: The $300M ARR AI tool that engineers can't stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell• Granola: https://www.granola.ai/• Building Lovable: $10M ARR in 60 days with 15 people | Anton Osika (CEO and co-founder): https://www.lennysnewsletter.com/p/building-lovable-anton-osika• Inside Bolt: From near-death to ~$40m ARR in 5 months—one of the fastest-growing products in history | Eric Simons (founder & CEO of StackBlitz): https://www.lennysnewsletter.com/p/inside-bolt-eric-simons• Behind the product: Replit | Amjad Masad (co-founder and CEO): https://www.lennysnewsletter.com/p/behind-the-product-replit-amjad-masad• Everyone's an engineer now: Inside v0's mission to create a hundred million builders | Guillermo Rauch (founder and CEO of Vercel, creators of v0 and Next.js): https://www.lennysnewsletter.com/p/everyones-an-engineer-now-guillermo-rauch• Technique #3: Examples in Prompts: From Zero-Shot to Few-Shot: https://learnprompting.org/docs/basics/few_shot?srsltid=AfmBOor2owyGXtzJZ8n0fJVCctM7UPZgZmH-mBuxRW4t9-kkaMd3LJVv• The Prompt Report: Insights from the Most Comprehensive Study of Prompting Ever Done: https://learnprompting.org/blog/the_prompt_report?srsltid=AfmBOoo7CRNNCtavzhyLbCMxc0LDmkSUakJ4P8XBaITbE6GXL1i2SvA0• State-of-the-Art Prompting for AI Agents | Y Combinator: https://www.youtube.com/watch?v=DL82mGde6wo• Use XML tags to structure your prompts: https://docs.anthropic.com/en/docs/build-with-claude/prompt-engineering/use-xml-tags• Role Prompting: https://learnprompting.org/docs/basics/roles?srsltid=AfmBOor2jcxJQvWBZyFa030Qt0fIIov3hSiWvI9VFyjO-Qp478EPJIU7• Is Role Prompting Effective?: https://learnprompting.org/blog/role_prompting?srsltid=AfmBOooiiyLD-0CsCYZ4m3SDhYOmtTyaTzeDo0FvK_i1x1gLM8MJS-Sn• Introduction to Decomposition Prompting Techniques: https://learnprompting.org/docs/advanced/decomposition/introduction?srsltid=AfmBOoojJmTQgBlmSlGYQ8kl-JPpVUlLKkL4YcFGS5u54JyeumUwlcBI• LLM Self-Evaluation: https://learnprompting.org/docs/reliability/lm_self_eval• Philip Resnik on X: https://x.com/psresnik• Anthropic's CPO on what comes next | Mike Krieger (co-founder of Instagram): https://www.lennysnewsletter.com/p/anthropics-cpo-heres-what-comes-next• Introduction to Ensembling Prompting: https://learnprompting.org/docs/advanced/ensembling/introduction?srsltid=AfmBOooGSyqsrjnEbXSYoKpG0ZlpT278NHQA6Fd8gMvNTJlWu7-qEYzh• Random forest: https://en.wikipedia.org/wiki/Random_forest• Chain-of-Thought Prompting: https://learnprompting.org/docs/intermediate/chain_of_thought?srsltid=AfmBOoqwE7SXlluy2sx_QY_VOKduyBplWtIWKEJaD6FkJW3TqeKPSJfx• Prompt Injecting: https://learnprompting.org/docs/prompt_hacking/injection?srsltid=AfmBOoqGgqbfXStrD6vlw5jy8HhEaESgGo2e57jyWL8lkZKktt_P6Zvn• Announcing HackAPrompt 2.0: The World's Largest AI Red-Teaming Hackathon: https://learnprompting.org/blog/announce-hackaprompt-2?srsltid=AfmBOopXKsHxy4aUtsvPCUtEu7x74NCAEnlTIdNzo7nfMDVwZ9ilTlkp• Infant with rare, incurable disease is first to successfully receive personalized gene therapy treatment: https://www.nih.gov/news-events/news-releases/infant-rare-incurable-disease-first-successfully-receive-personalized-gene-therapy-treatment• Building a magical AI code editor used by over 1 million developers in four months: The untold story of Windsurf | Varun Mohan (co-founder and CEO): https://www.lennysnewsletter.com/p/the-untold-story-of-windsurf-varun-mohan• Copilot: https://copilot.microsoft.com/chats/rcxhzvKgZvz8ajUrKdBtX• GitHub Copilot: https://github.com/features/copilot• Defensive Measures: https://learnprompting.org/docs/prompt_hacking/defensive_measures/introduction• Sam Altman on X: https://x.com/sama• Three Laws of Robotics: https://en.wikipedia.org/wiki/Three_Laws_of_Robotics• Anthropic's new AI model turns to blackmail when engineers try to take it offline: https://techcrunch.com/2025/05/22/anthropics-new-ai-model-turns-to-blackmail-when-engineers-try-to-take-it-offline/• Palisade Research: https://palisaderesearch.org/• When AI Thinks It Will Lose, It Sometimes Cheats, Study Finds: https://time.com/7259395/ai-chess-cheating-palisade-research/• A.I. Chatbots Defeated Doctors at Diagnosing Illness: https://www.nytimes.com/2024/11/17/health/chatgpt-ai-doctors-diagnosis.html• 1883 on Paramount+: https://www.paramountplus.com/shows/1883/• Black Mirror on Netflix: https://www.netflix.com/title/70264888• Daylight Computer: https://daylightcomputer.com/• Theodore Roosevelt's quote: https://www.goodreads.com/quotes/622252-i-wish-to-preach-not-the-doctrine-of-ignoble-ease• HackAPrompt 2.0: https://www.hackaprompt.com/—Recommended books:• Ender's Game: https://www.amazon.com/Enders-Ender-Quintet-Orson-Scott/dp/0812550706• The River of Doubt: Theodore Roosevelt's Darkest Journey: https://www.amazon.com/River-Doubt-Theodore-Roosevelts-Darkest/dp/0767913736—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Hilary Gridley is the Head of Core Product at WHOOP and a passionate thought leader in leveraging AI to elevate product teams and management practices. With extensive experience tackling challenging problems in regulated industries and high-stakes environments, Hilary emphasizes the importance of building resilience and adaptability within teams. Previously, she was a senior director of product at Big Health and a senior product marketing manager at Dropbox.In this episode, you'll learn:• How to teach your team to be able to “take a punch”• Specific tactics to counter negative perceptions and reframe setbacks productively• Powerful behavioral strategies to form positive habits• Practical approaches for creating space in your workday to encourage creativity and deep thinking• The underestimated potential of AI in accelerating your personal and professional growth• Why you're not the protagonist at your company (and why that's liberating)• How WHOOP uses reward loops to drive real behavior change—Brought to you by:WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUsPersona—A global leader in digital identity verificationAttio—The powerful, flexible CRM for fast-growing startups—Where to find Hilary Gridley:• X: https://x.com/yourgirlhils• LinkedIn: https://www.linkedin.com/in/hilarygridley/• Newsletter: https://hils.substack.com/• Maven course: https://maven.com/hilary-gridley/ai-powered-people-management—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Hilary's background(04:31) Teaching teams to handle criticism and setbacks(17:57) Behavioral activation and mental health in the workplace(22:59) The importance of putting yourself out there(27:51) Transparency and communication in leadership(38:10) How to respectfully disagree with your manager(41:49) How to use “magic questions” to decode how people think(49:54) Why you're not the protagonist at your company(52:48) Aligning with the CEO's vision(01:01:02) Building effective habits(01:11:14) Promoting team well-being(01:14:28) Creating space for creativity(01:20:45) AI's role in accelerating learning(01:30:35) Pivotal career moments(01:37:21) Lessons from failure(01:39:49) Exciting new features of WHOOP 5.0(01:44:19) Lightning round and final thoughts—Referenced:• How to become a supermanager with AI: https://www.lennysnewsletter.com/p/how-to-become-a-supermanager-with• How custom GPTs can make you a better manager | Hilary Gridley (Head of Core Product at Whoop): https://www.lennysnewsletter.com/p/how-custom-gpts-can-make-you-a-better-manager• WHOOP: https://www.whoop.com/• Big Health: https://www.bighealth.com/• What is behavioral activation?: https://www.medicalnewstoday.com/articles/behavioral-activation• Will Ahmed on LinkedIn: https://www.linkedin.com/in/willahmed/• Joe Gebbia on LinkedIn: https://www.linkedin.com/in/jgebbia/• Zach Abrams on LinkedIn: https://www.linkedin.com/in/zacharyabrams/• Coinbase: https://www.coinbase.com/• Bridge: https://www.bridge.xyz/• Stripe: https://stripe.com/• The paths to power: How to grow your influence and advance your career | Jeffrey Pfeffer (author of 7 Rules of Power, professor at Stanford GSB): https://www.lennysnewsletter.com/p/the-paths-to-power-jeffrey-pfeffer• Paths to Power course: https://jeffreypfeffer.com/wp-content/uploads/2019/10/Pfeffer-OB377-Course-Outline-2018.pdf• VO₂ max: https://en.wikipedia.org/wiki/VO2_max• Peter Attia on X: https://x.com/PeterAttiaMD• Hilary Gridley's 30 days of GPT: https://docs.google.com/spreadsheets/d/1zJ4rbi9YcQuGqGxc6-AQD0-44oT9l4Eyono0AdpgJbA/edit?gid=0#gid=0• The Handle Bar in Boston: https://www.thehandlebarstudios.com/ourstudios/charlestown• From chalkboards to chatbots: Transforming learning in Nigeria, one prompt at a time: https://blogs.worldbank.org/en/education/From-chalkboards-to-chatbots-Transforming-learning-in-Nigeria• Product Management Logic Coach GPT: https://chatgpt.com/g/g-673290301700819084afa36bdbcdfa3b-product-management-logic-coach• Dropbox: https://www.dropbox.com/• WHOOP Advanced Labs: https://www.whoop.com/us/en/waitlist/?srsltid=AfmBOor2pP5qC3n7I23Z0ZIrYE99CjAKT9xSHQxbuyxmz_wFUBGH3e-n• Negative capability: https://en.wikipedia.org/wiki/Negative_capability• John Keats: https://en.wikipedia.org/wiki/John_Keats• The Rehearsal: https://www.hbo.com/the-rehearsal• Zwift: https://www.zwift.com/• Beavis and Butthead Do ‘Creep': https://www.youtube.com/watch?v=zv_gSmH0Ieg• “Sea Grapes” by Derek Walcott: https://www.poetryfoundation.org/poems/57111/sea-grapes• Free month of WHOOP: https://join.whoop.com/us/en/hilary/—Recommended books:• 7 Rules of Power: https://jeffreypfeffer.com/books/7-rules-of-power/• Outlive: The Science and Art of Longevity: https://www.amazon.com/Outlive-Longevity-Peter-Attia-MD/dp/0593236599• East of Eden: https://www.amazon.com/East-Eden-John-Steinbeck-Centennial/dp/0142004235• The Sun Also Rises: https://www.amazon.com/Sun-Also-Rises-Hemingway-Library/dp/1501121960/• Anna Karenina: https://www.amazon.com/Anna-Karenina-Leo-Tolstoy/dp/0143035002—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Bob Baxley is a design leader who has shaped products used by billions at Apple, Pinterest, Yahoo, and ThoughtSpot. During his eight years at Apple, he led design for the online store and the App Store, and witnessed the iPhone's transformative launch while working under Steve Jobs. A student of history turned software craftsman, Bob discovered his calling after exploring photography, filmmaking, and music, ultimately recognizing software as the most powerful creative medium of our time. Bob champions the moral obligation designers have to reduce frustration in people's daily digital interactions.What you'll learn:• Why design should report to engineering, not product• The “Beatles principle”—why the best products come from teams of 4 to 6, not 40 to 60• How to create design tenets vs. principles (with real examples)• The counterintuitive reason to delay drawing or prototyping as long as possible• Why software is fundamentally a medium, like film or music (not just a tool)• Why Bob “bounced off the culture” at Pinterest, and lessons from failure• The lunar landing story that teaches us about championing radical ideas• How to evaluate if a company truly values design before joining• The moral obligation of software makers to build great products—This entire episode is brought to you by Stripe—helping companies of all sizes grow revenue.—Where to find Bob Baxley:• Instagram: https://www.instagram.com/baxley/• LinkedIn: https://www.linkedin.com/in/bbaxley/• Website: http://www.bobbaxley.com/—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Bob Baxley(03:52) Apple's lasting culture(06:15) Navigating unique company cultures(13:19) Finding a company that truly values your role(15:46) What is design?(17:17) How to help founders understand the value of design(23:08) How to align product managers and designers(26:31) Design reporting to engineering(30:54) Integrating engineers early in the design process(33:43) The maker mindset(35:14) Challenging the assumption that design is time-intensive(38:04) Design tenets vs. design principles(45:25) The moral obligation of great design(51:48) Understanding software as a medium(01:01:20) Reducing ambiguity for product teams(01:07:04) Giving designers space for creativity(01:08:48) The "primal mark" concept(01:12:05) AI prototyping tools: benefits and risks(01:17:00) AI as a life coach(01:21:22) Life lessons from the Apollo program(01:28:24) Lightning round and final thoughts—Referenced:• Steve Jobs: https://en.wikipedia.org/wiki/Steve_Jobs• Walt Disney: https://en.wikipedia.org/wiki/Walt_Disney• Pinterest: https://www.pinterest.com/• X: https://x.com/• Uber: https://www.uber.com/• Airbnb: https://www.airbnb.com/• Slack: https://slack.com/• Ed Catmull on X: https://x.com/edcatmull• John Lasseter on X: https://x.com/johnlasseter5• Apple patented a pizza box, for pizzas: https://www.theverge.com/2017/5/16/15646154/apple-pizza-box-patent-come-on• Humane: https://en.wikipedia.org/wiki/Humane_Inc.• Jony Ive: https://en.wikipedia.org/wiki/Jony_Ive• Tony Fadell on LinkedIn: https://www.linkedin.com/in/tonyfadell/• Hiroki Asai on LinkedIn: https://www.linkedin.com/in/hiroki-asai-a44137110/• Tim Cook on X: https://x.com/tim_cook• ThoughtSpot: https://www.thoughtspot.com/• Ben Silbermann on LinkedIn: https://www.linkedin.com/in/silbermann/• Ajeet Singh on LinkedIn: https://www.linkedin.com/in/ajeetsinghmann/• Honeywell: https://www.honeywell.com• IDEO: https://www.ideo.com/• Nutanix: https://www.nutanix.com/• Lego: https://www.lego.com/• Leica: https://leica-camera.com/• Porsche: https://www.porsche.com/• Patagonia: https://www.patagonia.com• Brian Eno's website: https://www.brian-eno.net/• Scenius: why creatives are stronger together: https://thecreativelife.net/scenius/• The Beatles website: https://www.thebeatles.com/• Disneyland: https://disneyland.disney.go.com/destinations/disneyland/• Tomorrowland: https://disneyland.disney.go.com/destinations/disneyland/tomorrowland/• Unconventional product lessons from Binance, N26, Google, more | Mayur Kamat (CPO at N26, ex-Binance Head of Product): https://www.lennysnewsletter.com/p/unorthodox-product-lessons-from-n26-and-more• Larry Page: https://en.wikipedia.org/wiki/Larry_Page• Sergey Brin: https://en.wikipedia.org/wiki/Sergey_Brin• Design Principles: https://principles.design/• Tableau: https://www.tableau.com/• Figma: https://www.figma.com/• Target self-checkout: https://corporate.target.com/press/fact-sheet/2024/03/checkout-improvements• Everyone's an engineer now: Inside v0's mission to create a hundred million builders | Guillermo Rauch (founder and CEO of Vercel, creators of v0 and Next.js): https://www.lennysnewsletter.com/p/everyones-an-engineer-now-guillermo-rauch• eBay: https://www.ebay.com/• Williams Sonoma: https://www.williams-sonoma.com/• Amazon: https://www.amazon.com/• Monument to a Dead Child | Raw Data: https://podcasts.apple.com/ca/podcast/monument-to-a-dead-child/id1042137974• Toast: https://pos.toasttab.com/• The Primal Mark: How the Beginning Shapes the End in the Development of Creative Ideas: https://www.gsb.stanford.edu/faculty-research/publications/primal-mark-how-beginning-shapes-end-development-creative-ideas• The Plant: https://pixar.fandom.com/wiki/The_Plant• Microsoft CPO: If you aren't prototyping with AI you're doing it wrong | Aparna Chennapragada: https://www.lennysnewsletter.com/p/microsoft-cpo-on-ai• How have I been complicit in creating the conditions I say I don't want? | Jerry Colonna (CEO of Reboot, executive coach, former VC): https://www.lennysnewsletter.com/p/jerry-colonna• Joff Redfern on LinkedIn: https://www.linkedin.com/in/mejoff/• John C. Houbolt: https://www.nasa.gov/centers-and-facilities/langley/john-c-houbolt/• The Apollo program: https://www.nasa.gov/the-apollo-program/• Archive clip: JFK at Rice University, Sept. 12, 1962—“We choose to go to the moon”: https://www.youtube.com/watch?v=QXqlziZV63k• Alan Shepard: https://www.nasa.gov/former-astronaut-alan-shepard/• Blue Origin: https://www.blueorigin.com/• Yuri Gagarin: https://en.wikipedia.org/wiki/Yuri_Gagarin• Wernher von Braun: https://en.wikipedia.org/wiki/Wernher_von_Braun• Yuri Kondratyuk: https://en.wikipedia.org/wiki/Yuri_Kondratyuk• John Houbolt's memo: https://space.stackexchange.com/questions/2823/text-of-john-houbolts-letter-proposing-lunar-orbit-rendezvous-for-apollo• Severance on AppleTV+: https://tv.apple.com/us/show/severance/umc.cmc.1srk2goyh2q2zdxcx605w8vtx• Lawrence of Arabia on Prime Video: https://www.amazon.com/Lawrence-Arabia-Peter-OToole/dp/B0088OINTU• Leica M6: https://leica-camera.com/en-US/photography/cameras/m/m6• Habitica: https://habitica.com/static/home• Andor on Disney+: https://www.disneyplus.com/browse/entity-faba988a-a9f5-45f2-a074-0775a7d6f67a• Edward Tufte quote: https://quotefancy.com/quote/1449650/Edward-Tufte-Good-design-is-clear-thinking-made-visible-bad-design-is-stupidity-made• Ansel Adams quote: https://www.brainyquote.com/quotes/ansel_adams_106035• It Takes a Village to Determine the Origins of an African Proverb: https://www.npr.org/sections/goatsandsoda/2016/07/30/487925796/it-takes-a-village-to-determine-the-origins-of-an-african-proverb• Henry Modisett on LinkedIn: https://www.linkedin.com/in/henrymodisett/• Perplexity: https://www.perplexity.ai/• Golden State Warriors: https://www.nba.com/warriors/• Steph Curry: https://www.espn.com/nba/player/_/id/3975/stephen-curry—Recommended books:• From Counterculture to Cyberculture: Stewart Brand, the Whole Earth Network, and the Rise of Digital Utopianism: https://www.amazon.com/Counterculture-Cyberculture-Stewart-Network-Utopianism/dp/0226817423• Hare Brain, Tortoise Mind: How Intelligence Increases When You Think Less: https://www.amazon.com/Hare-Brain-Tortoise-Mind-Intelligence/dp/0060955414• The Elements of Typographic Style: https://www.amazon.com/Elements-Typographic-Style-Robert-Bringhurst/dp/0881791326• Zen and the Art of Motorcycle Maintenance: An Inquiry into Values: https://www.amazon.com/Zen-Art-Motorcycle-Maintenance-Inquiry/dp/0060589469• Time and the Art of Living: https://www.amazon.com/Time-Art-Living-Robert-Grudin/dp/0062503553/—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Sebastian Barrios was the longtime head of product and engineering at Mercado Libre, the largest company in Latin America—valued at over $100 billion and home to more than 100,000 employees. There, he led a team of more than 18,000 engineers across 18 countries and oversaw an astonishing 30,000 code deployments a day. Before Mercado Libre, he founded multiple startups, including a ridesharing company that competed directly with Uber in Latin America. And at just 17, he got a personal phone call from Steve Jobs asking him to take his app off the App Store. Today, Sebastian is the SVP of Engineering at Roblox.What you'll learn:• Why Mercado Libre operates with 95% fewer PMs than typical tech companies (and how it actually works)• How to maintain product quality with 30,000 daily deployments and distributed ownership• The weekly email system Sebastian uses to maintain alignment with leadership• How to build a culture of radical candor and direct feedback in a traditionally hierarchical region• The counterintuitive approach to product reviews that keeps 18,000 engineers aligned• How to evaluate hype cycles (crypto, AI) pragmatically while staying innovative—Brought to you by:Merge—A single API to add hundreds of integrations into your appVanta—Automate compliance. Simplify securityLinkedIn Ads—Reach professionals and drive results for your business—Where to find Sebastian Barrios:• LinkedIn: https://www.linkedin.com/in/zebas/—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Sebastian Barrios and Mercado Libre(05:03) Mercado Libre's scale and unique ways of operating(14:48) AI's impact on operations(19:19) Empowering teams and reducing fear of failure(34:20) The importance of radical candor(38:26) Weekly updates(41:03) Avoiding hype cycles(44:24) When Steve Jobs personally called 17-year-old Sebastian(49:00) Building successful app businesses(55:33) Unique personal habits(01:04:00) Raising independent children(01:07:15) Lightning round and final thoughts—Referenced:• Mercado Libre: https://www.mercadolibre.com/• Claude: https://claude.ai/• Salesforce: https://www.salesforce.com/• Nvidia: https://www.nvidia.com/• TikTok: https://www.tiktok.com/• Adobe: https://www.adobe.com/• Uber: https://www.uber.com/• OpenAI: https://openai.com/• Marcos Galperin on LinkedIn: https://www.linkedin.com/in/marcosgalperin/• Cursor: https://www.cursor.com/• Windsurf: https://windsurf.com/• Which companies produce the best product managers: https://www.lennysnewsletter.com/p/which-companies-produce-the-best• Which companies accelerate PM careers most: https://www.lennysnewsletter.com/p/which-companies-accelerate-your-pm• How Revolut trains world-class product managers: The “local CEO” model, raw intellect over experience, and a cultural obsession with building wow products | Dmitry Zlokazov (Head of Product): https://www.lennysnewsletter.com/p/how-revolut-trains-world-class-product-managers• Intercom: https://www.intercom.com/• Atlassian: https://www.atlassian.com/• Radical Candor: From theory to practice with author Kim Scott: https://www.lennysnewsletter.com/p/radical-candor-from-theory-to-practice• Managing up: https://www.lennysnewsletter.com/p/managing-up• Steve Jobs: https://en.wikipedia.org/wiki/Steve_Jobs• Tobi Lütke's leadership playbook: Playing infinite games, operating from first principles, and maximizing human potential (founder and CEO of Shopify): https://www.lennysnewsletter.com/p/tobi-lutkes-leadership-playbook• Everything Everywhere All at Once: https://www.imdb.com/title/tt6710474/• Dune on Max: https://www.max.com/movies/dune/e7dc7b3a-a494-4ef1-8107-f4308aa6bbf7• Bluey on Disney+: https://www.disneyplus.com/browse/entity-fa6973b9-e7cf-49fb-81a2-d4908e4bf694• Mentava: https://www.mentava.com/• Matt Bateman's website: https://mattbateman.xyz/• Beast Academy: https://beastacademy.com/• David protein bars: https://davidprotein.com/• Marc Andreessen on X: https://x.com/pmarca• Tatami mats: https://en.wikipedia.org/wiki/Tatami—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• High Output Management: https://www.amazon.com/High-Output-Management-Andrew-Grove/dp/0679762884/• The Odyssey: https://www.amazon.com/Odyssey-Homer/dp/0140268863• The Dream Machine: https://www.amazon.com/Dream-Machine-M-Mitchell-Waldrop/dp/1732265119/• Dune: https://www.amazon.com/Dune-Chronicles-Book-1/dp/0441013597/—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Mike Krieger is the chief product officer of Anthropic and the co-founder of Instagram. After leaving Meta, he co-founded Artifact, an AI-powered news app that I absolutely loved, and joined Anthropic to lead product in 2024.In this episode, you'll learn:• How Anthropic uses AI to write 90-95% of code for some products and the surprising new bottlenecks this creates• Why embedding product managers with AI researchers yields 10x the impact of traditional product development• The three areas where product teams can still add massive value as AI gets smarter• How Anthropic plans to compete with OpenAI long-term• How to use Claude as your product strategy partner (with specific prompting techniques)• Why Mike shut down Artifact despite loving the product, and what founders can learn from it• Where AI startups should build to avoid getting killed by OpenAI, Anthropic, and Google• Why MCP (Model Context Protocol) might reshape how all software works• The counterintuitive product metrics that matter for AI• How to evaluate whether your company is maximizing AI's potential or just scratching the surface—Brought to you by:Productboard—Make products that matterStripe—Helping companies of all sizes grow revenueOneSchema—Import CSV data 10x faster—Where to find Mike Krieger:• X: https://x.com/mikeyk• LinkedIn: https://www.linkedin.com/in/mikekrieger/—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Mike Krieger(04:20) What Mike has changed his mind about regarding AI capabilities(07:38) How to avoid scary AI scenarios(08:55) Skills kids will need in an AI world(11:53) How product development changes when 90% of code is written by AI(17:07) Claude helping with product strategy(21:16) A new way of working(23:55) The future value of product teams in an AI world(27:18) Prompting tricks to get more out of Claude(29:52) The Rick Rubin collaboration on “vibe coding”(32:42) How Mike was recruited to Anthropic(35:55) Why Mike shut down Artifact(42:41) Anthropic vs. OpenAI(47:11) Where AI founders should play to avoid getting squashed(51:58) How companies can best leverage Anthropic's models and APIs(54:29) The role of MCPs (Model Context Protocols)(58:25) Claude's questions for Mike(01:03:15) Claude's heartfelt message to Mike—Referenced:• Anthropic: https://www.anthropic.com/• Claude Opus 4: https://www.anthropic.com/claude/opus• Dario Amodei on X: https://x.com/darioamodei• AI 2027: https://ai-2027.com/• Tobi Lütke's leadership playbook: Playing infinite games, operating from first principles, and maximizing human potential (founder and CEO of Shopify): https://www.lennysnewsletter.com/p/tobi-lutkes-leadership-playbook• Claude Shannon: https://en.wikipedia.org/wiki/Claude_Shannon• Information theory: https://en.wikipedia.org/wiki/Information_theory• TypeScript: https://www.typescriptlang.org/• Python: https://www.python.org/• Rust: https://www.rust-lang.org/• Bending the universe in your favor | Claire Vo (LaunchDarkly, Color, Optimizely, ChatPRD): https://www.lennysnewsletter.com/p/bending-the-universe-in-your-favor• Announcing a brand-new podcast: “How I AI” with Claire Vo: https://www.lennysnewsletter.com/p/announcing-a-brand-new-podcast-how• A conversation with OpenAI's CPO Kevin Weil, Anthropic's CPO Mike Krieger, and Sarah Guo: https://www.youtube.com/watch?v=IxkvVZua28k• Jack Clark on LinkedIn: https://www.linkedin.com/in/jack-clark-5a320317/• Artifact: https://en.wikipedia.org/wiki/Artifact_(app)• Joel Lewenstein on LinkedIn: https://www.linkedin.com/in/joel-lewenstein/• Daniela Amodei on LinkedIn: https://www.linkedin.com/in/daniela-amodei-790bb22a/• Boris Cherny on LinkedIn: https://www.linkedin.com/in/bcherny/• Gunnar Gray on LinkedIn: https://www.linkedin.com/in/gunnargray/• The Model Context Protocol: https://www.anthropic.com/news/model-context-protocol• The rise of Cursor: The $300M ARR AI tool that engineers can't stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell• Building Lovable: $10M ARR in 60 days with 15 people | Anton Osika (CEO and co-founder): https://www.lennysnewsletter.com/p/building-lovable-anton-osika• Inside Bolt: From near-death to ~$40m ARR in 5 months—one of the fastest-growing products in history | Eric Simons (founder and CEO of StackBlitz): https://www.lennysnewsletter.com/p/inside-bolt-eric-simons• Jimmy Kimmel Live: https://www.youtube.com/user/JimmyKimmelLive• ChatGPT: https://chatgpt.com/• Gemini: https://gemini.google.com/app• OpenAI's CPO on how AI changes must-have skills, moats, coding, startup playbooks, more | Kevin Weil (CPO at OpenAI, ex-Instagram, Twitter): https://www.lennysnewsletter.com/p/kevin-weil-open-ai• Windsurf: https://windsurf.com/• Menlo Ventures: https://menlovc.com/• Harvey: https://www.harvey.ai/• Manus: https://manus.im/• Bench: https://www.bench-ai.com/• Strategy Letter V: https://www.joelonsoftware.com/2002/06/12/strategy-letter-v/• Kevin Scott on LinkedIn: https://www.linkedin.com/in/jkevinscott/—Recommended books:• The Goal: A Process of Ongoing Improvement: https://www.amazon.com/Goal-Process-Ongoing-Improvement/dp/0884271951• The Way of the Code: The Timeless Art of Vibe Coding: https://www.thewayofcode.com/• The Hard Thing About Hard Things: Building a Business when There Are No Easy Answers―Straight Talk on the Challenges of Entrepreneurship: https://www.amazon.com/Hard-Thing-About-Things-Building/dp/0062273205—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Sachin Kansal is chief product officer at Uber, where he oversees the Rider, Driver, Delivery, Grocery, and New Verticals product lines used for 33 million daily trips worldwide. He's been in product for over 25 years (at Google, Palm, Flywheel, and now Uber). He is known for his “extreme dogfooding” ethos—personally completing almost a thousand Uber driving and delivery trips to sharpen his product insight and user empathy—and his “ship, ship, ship” mantra, which drives rapid iteration across Uber's global teams.What you will learn:1. Dogfooding at scale2. “Ship, ship, ship” as a cultural mantra3. Obsession with inputs over outputs4. Uber's hybrid marketplace vision for autonomy5. How Uber changed its culture to focus on profitability6. What to do when data says “no” but your gut says “yes”7. Career advice: maximize cycles8. AI as a research assistant, not an oracle9. Uber rider etiquette tips—Brought to you by:• Paragon—Ship every SaaS integration your customers want• Stripe—Financial infrastructure to grow your revenue• Coda—The all-in-one collaborative workspace—Where to find Sachin Kansal:• LinkedIn: https://www.linkedin.com/in/sachinkansal/—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Sachin's background(05:00) Dogfooding in practice(11:24) Empathy and understanding drivers(20:18) Balancing metrics and user experience(22:04) Operationalizing dogfooding(24:26) Challenges and solutions in dogfooding(29:49) The motto: “ship, ship, ship”(36:37) Product announcements and live demos(40:49) Career advice for product managers(43:51) The evolution of product management with AI(46:55) Collaboration between engineers and product managers(49:36) Uber's vision for self-driving cars(55:59) Uber's path to profitability(01:01:58) Balancing data and gut decisions(01:07:21) AI tools in product management(01:10:14) Failure corner(01:13:48) Lightning round and final thoughts—Referenced:• Uber: https://www.uber.com/• Oracle: https://www.oracle.com/• Snowflake: https://www.snowflake.com/en/• Fivetran: https://go.fivetran.com/• Uber for Business: https://www.uber.com/us/en/business• McDonald's: https://www.mcdonalds.com/• Domino's: https://www.dominos.com• PalmPilot: https://en.wikipedia.org/wiki/PalmPilot• Praveen Neppalli Naga on LinkedIn: https://www.linkedin.com/in/pneppalli/• May Mobility: https://maymobility.com/• Uber strikes deal with May Mobility to deploy ‘thousands' of robotaxis: https://www.theverge.com/news/659563/uber-may-mobility-autonomous-ridehail-partnership• Waymo: https://waymo.com/• WeRide: https://www.weride.ai/• Uber and Avride Announce Autonomous Delivery and Mobility Partnership: https://investor.uber.com/news-events/news/press-release-details/2024/Uber-and-Avride-Announce-Autonomous-Delivery-and-Mobility-Partnership/default.aspx• Dara Khosrowshahi on X: https://x.com/dkhos• Uber Elevate: https://www.uber.com/us/en/elevate/vision/• Uber AV: https://www.uber.com/us/en/autonomous/• Uber Reserve: https://www.uber.com/us/en/ride/how-it-works/reserve/• Uber for teens: https://www.uber.com/us/en/ride/teens/• Flywheel: https://www.flywheel.com/• ChatGPT: https://chatgpt.com/• Gemini: https://gemini.google.com/app• NotebookLM: https://notebooklm.google/• Behind the product: NotebookLM | Raiza Martin (Senior Product Manager, AI @ Google Labs): https://www.lennysnewsletter.com/p/googles-notebooklm-raiza-martin• BlackBerry: https://en.wikipedia.org/wiki/BlackBerry• Peaky Blinders on Netflix: https://www.netflix.com/title/80002479• Deep research: https://openai.com/index/introducing-deep-research/—Recommended books:• Blitzscaling: The Lightning-Fast Path to Building Massively Valuable Companies: https://www.amazon.com/Blitzscaling-Lightning-Fast-Building-Massively-Companies/dp/1524761419• Nobody Wants to Read Your Sh*t: Why That Is And What You Can Do About It: https://www.amazon.com/Nobody-Wants-Read-Your-Sh-ebook/dp/B01GZ1TJBI• Steve Jobs: https://www.amazon.com/Steve-Jobs-Walter-Isaacson/dp/1451648537• Elon Musk: https://www.amazon.com/Elon-Musk-Walter-Isaacson/dp/1982181281• The Hard Thing About Hard Things: Building a Business When There Are No Easy Answers―Straight Talk on the Challenges of Entrepreneurship: https://www.amazon.com/Hard-Thing-About-Things-Building/dp/0062273205—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Krithika Shankarraman was the first marketing hire at OpenAI and Stripe and led marketing at Retool. At OpenAI, she established marketing foundations for ChatGPT for consumers and enterprises, as well as their developer API platform. While at Stripe, she spent over eight years building and scaling their marketing function from scratch. An engineer turned marketer, Krithika brings a uniquely analytical approach to marketing. She currently serves as Entrepreneur in Residence at Thrive Capital, where she helps portfolio companies on all things marketing.What you will learn:1. Why do most marketing playbooks often fail, and what's a better way?2. Which marketing lever should I pull first?3. Why is trying to be better than competitors usually a losing strategy?4. How do I craft positioning that actually converts?5. What makes messaging stick with developers, enterprises, and consumers?6. What pricing experiments actually move revenue?7. What is working at OpenAI really like?8. Why does consistency and quality matter more than speed?—Brought to you by:Eppo — Run reliable, impactful experimentsAirtable ProductCentral—Launch to new heights with a unified system for product developmentLinkedIn Ads—Reach professionals and drive results for your business—Where to find Krithika Shankarraman:• X: https://x.com/krithix• LinkedIn: https://www.linkedin.com/in/krithix/• Website: https://krithix.com/—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Krithika(04:22) Early marketing lessons from OpenAI(11:17) Diagnosing marketing needs(15:06) The DATE framework and why being cheaper is a race to the bottom(17:11) Marketing strategies at Retool(22:29) Insights from marketing at Stripe(32:33) The importance of consistent marketing communication(39:55) Criteria for hiring a marketing expert(41:43) “Capital M” vs. “lowercase m” marketing(43:05) ChatGPT vs. Claude: market dominance(45:31) The future of AI and its societal impact(47:09) Work-life balance(48:41) Transitioning to Thrive(52:35) Career advice for marketers(55:00) The importance of taste and creativity in the AI era(01:00:04) AI product pricing(01:03:21) AI tools in marketing(01:05:17) Failure corner(01:08:46) Lightning round and final thoughts—Referenced:• OpenAI: https://openai.com/• Stripe: https://stripe.com/• Retool: https://retool.com/• Dropbox: https://www.dropbox.com/• Sam Altman talks about his business model: https://www.youtube.com/watch?v=pLnyjxgFxew• The art and science of pricing | Madhavan Ramanujam (Monetizing Innovation, Simon-Kucher): https://www.lennysnewsletter.com/p/the-art-and-science-of-pricing-madhavan• Pricing your SaaS product: https://www.lennysnewsletter.com/p/saas-pricing-strategy• Netflix: https://www.netflix.com/• Stripe Connect: https://stripe.com/connect• John Collison on X: https://x.com/collision• Patrick Collison on X: https://x.com/patrickc• Cristina Cordova on LinkedIn: https://www.linkedin.com/in/cristinajcordova/• Hackpad: https://en.wikipedia.org/wiki/Hackpad• Building Wiz: the fastest-growing startup in history | Raaz Herzberg (CMO and VP Product Strategy): https://www.lennysnewsletter.com/p/building-wiz-raaz-herzberg• Wiz: https://www.wiz.io/• Thrive Capital: https://thrivecap.com/• Brian Chesky's new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach• Claude: https://claude.ai/new• ChatGPT: https://chatgpt.com/• Lessons from scaling Stripe | Claire Hughes Johnson (former COO of Stripe): https://www.lennysnewsletter.com/p/lessons-from-scaling-stripe-tactics• Databricks: https://www.databricks.com/• Everyone's an engineer now: Inside v0's mission to create a hundred million builders | Guillermo Rauch (founder and CEO of Vercel, creators of v0 and Next.js): https://www.lennysnewsletter.com/p/everyones-an-engineer-now-guillermo-rauch• Tobi Lütke's leadership playbook: Playing infinite games, operating from first principles, and maximizing human potential (founder and CEO of Shopify): https://www.lennysnewsletter.com/p/tobi-lutkes-leadership-playbook• OpenAI's CPO on how AI changes must-have skills, moats, coding, startup playbooks, more | Kevin Weil (CPO at OpenAI, ex-Instagram, Twitter): https://www.lennysnewsletter.com/p/kevin-weil-open-ai• April Dunford on product positioning, segmentation, and optimizing your sales process: https://www.lennysnewsletter.com/p/april-dunford-on-product-positioning• A step-by-step guide to crafting a sales pitch that wins | April Dunford (author of Obviously Awesome and Sales Pitch): https://www.lennysnewsletter.com/p/a-step-by-step-guide-to-crafting• Severance on AppleTV+: https://tv.apple.com/us/show/severance/• Granola: https://www.granola.ai/• Some people think AI writing has a tell—the em dash. Writers disagree: https://www.washingtonpost.com/technology/2025/04/09/ai-em-dash-writing-punctuation-chatgpt/—Recommended books:• Obviously Awesome: How to Nail Product Positioning So Customers Get It, Buy It, Love It: https://www.amazon.com/Obviously-Awesome-Product-Positioning-Customers/dp/1999023005• Circe: https://www.amazon.com/Circe-Madeline-Miller/dp/0316556327/—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Mayur Kamat is the chief product officer at N26—a $9 billion neobank serving over 7 million customers in 25 countries—where he leads product, design, data, and research. Prior to N26, Mayur was Head of Product at Binance, growing the crypto exchange to a peak $400 billion valuation. Earlier in his career, he built and scaled products at Google (Gmail Mobile, Hangouts), Microsoft, and travel unicorn Agoda.Learn:1. How to find and focus on the highest-leverage problems2. Why you shouldn't optimize for compensation early in your career3. Why you should optimize for strengths, not weaknesses4. Why you need to decide if you truly want the C-suite path5. Why working at a fintech company creates exceptional PMs6. Strategy = hypothesis × experimentation velocity7. Small, fast wins compound faster than big, slow bets—Brought to you by:• WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs• Paragon—Ship every SaaS integration your customers want• Vanta—Automate compliance. Simplify security.—Where to find Mayur Kamat:• X: https://x.com/5degreez• LinkedIn: https://www.linkedin.com/in/mayur/—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction and Mayur's background(04:49) Working at Binance: An inside look(18:18) Career advice for product managers(27:00) PM career paths(33:58) Understanding fintech customers(36:00) Understanding your strengths(44:46) Creating a culture of experimentation(51:14) Hiring and developing top talent(54:50) Building a diverse product portfolio(57:08) Working in high talent density areas(59:43) Personal and professional balance(01:06:32) High-leverage opportunities and decision making(01:14:28) AI tools in the workplace(01:19:14) Failure corner(01:25:11) Lightning round and final thoughts—Referenced:• Binance: https://www.binance.us/• Google: https://about.google/• Microsoft: https://www.microsoft.com/• Agoda: https://www.agoda.com• N26: https://n26.com/• Which companies accelerate PM careers most: https://www.lennysnewsletter.com/p/which-companies-accelerate-your-pm• Which companies produce the best product managers: https://www.lennysnewsletter.com/p/which-companies-produce-the-best• Bezos Says Work-Life Balance is a “Debilitating” Phrase: https://www.investopedia.com/news/bezos-says-worklife-balance-debilitating-phrase/• Maslow's Hierarchy of Needs: https://www.simplypsychology.org/maslow.html• PayPal Mafia: https://en.wikipedia.org/wiki/PayPal_Mafia• Changpeng Zhao on LinkedIn: https://www.linkedin.com/in/cpzhao/• Ray Dalio on LinkedIn: https://www.linkedin.com/in/raydalio/• Porter's five forces: https://en.wikipedia.org/wiki/Porter%27s_five_forces_analysis• Jonathan Rosenberg on X: https://x.com/jjrosenberg• Aura: https://buy.aura.com/• Intercom: https://www.intercom.com/• Palantir: https://www.palantir.com/• Revolut: https://www.revolut.com/• Chime: https://www.chime.com/• Stripe: https://stripe.com/• Dropbox: https://www.dropbox.com/• Alex Algard on LinkedIn: https://www.linkedin.com/in/alexalgard• Hiya: https://www.hiya.com/• Brian Chesky's new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach• Gemini: https://gemini.google.com/app• Writer: https://writer.com/• Google Hangouts: https://en.wikipedia.org/wiki/Google_Hangouts• Sundar Pichai on LinkedIn: https://www.linkedin.com/in/sundarpichai/• Google Meet: https://meet.google.com/landing• House on Hulu: https://www.hulu.com/series/ef39603f-eb90-4248-8237-f6168d7c1be1• Big Bang Theory on Hulu: https://www.hulu.com/series/9bde5aeb-5297-4290-b173-19a4d59cc11d• Adolescence on Netflix: https://www.netflix.com/title/81756069• The White Lotus on HBO: https://www.hbo.com/the-white-lotus• Robinhood: https://robinhood.com/us/en/• Nikita Bier's post on X about Bible Chat: https://x.com/nikitabier/status/1915252215507210349• Bible Chat: https://apps.apple.com/us/app/bible-chat-daily-devotional/id6448849666?mt=8• Suno: https://suno.com/home• Disfrutar: https://www.disfrutarbarcelona.com/—Recommended books:• StrengthsFinder 2.0: https://www.amazon.com/StrengthsFinder-2-0-Tom-Rath/dp/159562015X• The 5 Types of Wealth: A Transformative Guide to Design Your Dream Life: https://www.amazon.com/Types-Wealth-Transformative-Guide-Design/dp/059372318X—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Aparna Chennapragada is the chief product officer of experiences and devices at Microsoft, where she oversees AI product strategy for their productivity tools and work on agents. Previously, she was the CPO at Robinhood, spent 12 years at Google, and is also on the board of eBay and Capital One.What you'll learn:1. How “prompt sets are the new PRDs” and why prototyping with AI is now essential for effective product development2. The three key characteristics of AI agents: autonomy (delegation of tasks), complexity (handling multi-step challenges), and natural interaction (conversing beyond simple chat)3. Why NLX (natural language experience) is the new UX, requiring deliberate design principles for conversational interfaces4. Why the PM role isn't dying in the AI era—it's evolving to emphasize tastemaking and editing5. How living “one year in the future” can be operationalized with programs like Microsoft's Frontier6. How even traditional enterprises can balance cutting-edge AI adoption with appropriate governance through dual-track approaches7. Insights on leadership differences between Microsoft's Satya Nadella (known for multi-level thinking and early trendspotting) and Google's Sundar Pichai (mastery of complex ecosystems)8. The vision for human and AI collaboration in the workplace, where people and agents achieve outcomes greater than either could alone9. A practical framework for evaluating zero-to-one product opportunities—Brought to you by:Eppo—Run reliable, impactful experimentsPragmatic Institute—Industry‑recognized product, marketing, and AI training and certificationsCoda—The all-in-one collaborative workspace—Where to find Aparna Chennapragada:• X: https://x.com/aparnacd• LinkedIn: https://www.linkedin.com/in/aparnacd/—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Aparna Chennapragada(04:28) Aparna's stand-up comedy journey(07:29) Transition to Microsoft and enterprise insights(10:00) The Frontier program and AI integration(13:28) Understanding AI agents(17:59) NLX is the new UX(22:28) The future of product development(31:16) Building a custom Chrome extension(35:45) Leadership styles of Satya and Sundar(37:47) Counterintuitive lessons in product building(41:20) Inflection points for successful products(45:16) GitHub Copilot and code generation(48:34) Excel's enduring success(50:27) Pivotal career moments(54:55) The future of human-agent collaboration(56:25) Lightning round and final thoughts—Referenced:• Google Lens: https://lens.google/• Saturday Night Live: https://www.nbc.com/saturday-night-live• Reid Hoffman on LinkedIn: https://www.linkedin.com/in/reidhoffman/• Robinhood: https://robinhood.com/• eBay: https://www.ebay.com/• Capital One: https://www.capitalone.com/• Microsoft: https://www.microsoft.com/• Aparna's LinkedIn post about enterprise vs. consumer: https://www.linkedin.com/posts/aparnacd_every-enterprise-user-feature-has-a-shadow-activity-7321176091610542080-8X-E/• The Epic Split: https://en.wikipedia.org/wiki/The_Epic_Split• AI Frontiers: https://www.microsoft.com/en-us/research/lab/ai-frontiers/• OpenAI's CPO on how AI changes must-have skills, moats, coding, startup playbooks, more | Kevin Weil (CPO at OpenAI, ex-Instagram, Twitter): https://www.lennysnewsletter.com/p/kevin-weil-open-ai• Deepseek: https://www.deepseek.com/• Satya Nadella on LinkedIn: https://www.linkedin.com/in/satyanadella/• Tobi Lütke's leadership playbook: Playing infinite games, operating from first principles, and maximizing human potential (founder and CEO of Shopify): https://www.lennysnewsletter.com/p/tobi-lutkes-leadership-playbook• Tobi Lütke's post on X about reflexive AI: https://x.com/tobi/status/1909251946235437514• GitHub Copilot: https://github.com/features/copilot• Sundar Pichai on LinkedIn: https://www.linkedin.com/in/sundarpichai/• South Park “Underwear Gnomes” episode: https://southpark.cc.com/episodes/13y790/south-park-gnomes-season-2-ep-17• Google Home: https://home.google.com/welcome/• Cursor: https://www.cursor.com/• v0: https://v0.dev/• Bolt: https://bolt.net/• Lovable: https://lovable.dev/• Replit: https://replit.com/• Inside Bolt: From near-death to ~$40m ARR in 5 months—one of the fastest-growing products in history | Eric Simons (founder and CEO of StackBlitz): https://www.lennysnewsletter.com/p/inside-bolt-eric-simons• Building Lovable: $10M ARR in 60 days with 15 people | Anton Osika (CEO and co-founder): https://www.lennysnewsletter.com/p/building-lovable-anton-osika• Everyone's an engineer now: Inside v0's mission to create a hundred million builders | Guillermo Rauch (founder and CEO of Vercel, creators of v0 and Next.js): https://www.lennysnewsletter.com/p/everyones-an-engineer-now-guillermo-rauch• The rise of Cursor: The $300M ARR AI tool that engineers can't stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell• Behind the product: Replit | Amjad Masad (co-founder and CEO): https://www.lennysnewsletter.com/p/behind-the-product-replit-amjad-masad• Microsoft Excel World Championship: https://fmworldcup.com/microsoft-excel-world-championship/• Google Now: https://en.wikipedia.org/wiki/Google_Now• Hacks on Max: https://www.max.com/shows/hacks/67e940b7-aab2-46ce-a62b-c7308cde9de7• Granola: https://www.granola.ai/• Alan Kay quote: https://www.brainyquote.com/quotes/alan_kay_100831• Sindhu Vee's website: https://sindhuvee.com/• Nate Bargatze's website: https://natebargatze.com/—Recommended book:• A Brief History of Intelligence: Evolution, AI, and the Five Breakthroughs That Made Our Brains: https://www.amazon.com/Brief-History-Intelligence-Evolution-Breakthroughs/dp/0063286351—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Dmitry Zlokazov is the head of product at Revolut, the $45 billion fintech giant operating in over 50 countries, serving more than 50 million customers, and producing some of the world's top product leaders. Dmitry shares his hard-won lessons, contrarian org design principles, and day-to-day practices that power Revolut's relentless shipping velocity, culture of ownership, and unparalleled “wow” product experience.What you'll learn:1. Revolut's unique organizational approach, where “product owners” manage cross-functional pods as “local CEOs,” with genuine end-to-end ownership and hiring/firing power2. How a radical, ultra-flat structure enables more than 150 product owners to maintain founder-level quality and velocity across dozens of parallel launches3. How Revolut maintains quality while shipping hundreds of features across over 50 countries4. Why Revolut favors “raw intellect and hunger” over experience, and how internal transfers (including ex-engineers and ops managers) become the company's most successful product leaders5. How Revolut's founders review every single UI shipped, and why this founder detail obsession scales rather than limits innovation6. Their framework for launching new products—from ideation, validation, and first user cohort to rapid “algorithmization” and scaling across countries7. The importance of treating products that are 99% done as closer to 0% done, vs. 100% done—This entire episode is brought to you by Stripe—Helping companies of all sizes grow revenue.—Where to find Dmitry Zlokazov:• X: https://x.com/Dzlokazov• LinkedIn: https://www.linkedin.com/in/zlokazov/—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Dmitry and Revolut(03:41) Revolut's unique approach to product management(06:58) The role and responsibilities of product owners(09:28) Types of product owners at Revolut(15:50) Building “wow” products(25:00) Hiring practices(31:33) Managing teams and projects(41:07) Revolut's diverse product offerings(44:40) Scaling new products successfully(52:10) Attracting top talent(58:43) Failure corner(01:02:49) Lightning round and final thoughts—Referenced:• Revolut: https://www.revolut.com/• Intercom: https://www.intercom.com/• Palantir: https://www.palantir.com/• Which companies produce the best product managers: https://www.lennysnewsletter.com/p/which-companies-produce-the-best• Which companies accelerate PM careers most: https://www.lennysnewsletter.com/p/which-companies-accelerate-your-pm• Deliver WOW to our customers: https://www.revolut.com/blog/post/deliver-wow/• Nik Storonsky on LinkedIn: https://www.linkedin.com/in/nstoronsky• Vlad Yatsenko on LinkedIn: https://www.linkedin.com/in/yatsenko/• How Palantir built the ultimate founder factory | Nabeel S. Qureshi (entrepreneur and writer, ex-Palantir): https://www.lennysnewsletter.com/p/inside-palantir-nabeel-qureshi• Gokul Rajaram on designing your product development process, when and how to hire your first PM, a playbook for hiring leaders, getting ahead in you career, how to get started angel investing, more: https://www.lennysnewsletter.com/p/gokul-rajaram-on-designing-your-product• Gokul Rajaram on X: https://x.com/gokulr• Brian Chesky's new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach• Schlep blindness: https://www.paulgraham.com/schlep.html• Revolut Launches RevPoints Loyalty Programme, Turning Daily Expenses into Exclusive Rewards: https://www.revolut.com/news/revolut_launches_revpoints_loyalty_programme_turning_daily_expenses_into_exclusive_rewards/• Gemini: https://gemini.google.com/• ChatGPT: https://chatgpt.com/• Figma: https://www.figma.com/• Oppenheimer: https://www.imdb.com/title/tt15398776/• Manus: https://manus.im/• Eisenhower quote: https://quoteinvestigator.com/2017/11/18/planning/• Wealth protection: https://help.revolut.com/help/security-logging-in/wealth-protection/what-is-wealth-protection/—Recommended books:• The Hard Thing About Hard Things: Building a Business when There Are No Easy Answers―Straight Talk on the Challenges of Entrepreneurship: https://www.amazon.com/Hard-Thing-About-Things-Building/dp/0062273205• Build: An Unorthodox Guide to Making Things Worth Making―Personal Journey from Product Designer to Mentor: https://www.amazon.com/Build-Unorthodox-Guide-Making-Things/dp/0063046067—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Nabeel Qureshi is an entrepreneur, writer, researcher, and visiting scholar of AI policy at the Mercatus Center (alongside Tyler Cowen). Previously, he spent nearly eight years at Palantir, working as a forward-deployed engineer. His work at Palantir ranged from accelerating the Covid-19 response to applying AI to drug discovery to optimizing aircraft manufacturing at Airbus. Nabeel was also a founding employee and VP of business development at GoCardless, a leading European fintech unicorn.What you'll learn:• Why almost a third of all Palantir's PMs go on to start companies• How the “forward-deployed engineer” model works and why it creates exceptional product leaders• How Palantir transformed from a “sparkling Accenture” into a $200 billion data/software platform company with more than 80% margins• The unconventional hiring approach that screens for independent-minded, intellectually curious, and highly competitive people• Why the company intentionally avoids traditional titles and career ladders—and what they do instead• Why they built an ontology-first data platform that LLMs love• How Palantir's controversial “bat signal” recruiting strategy filtered for specific talent types• The moral case for working at a company like Palantir—Brought to you by:• WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs• Attio—The powerful, flexible CRM for fast-growing startups• OneSchema—Import CSV data 10x faster—Where to find Nabeel S. Qureshi:• X: https://x.com/nabeelqu• LinkedIn: https://www.linkedin.com/in/nabeelqu/• Website: https://nabeelqu.co/—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Nabeel S. Qureshi(05:10) Palantir's unique culture and hiring(13:29) What Palantir looks for in people(16:14) Why they don't have titles(19:11) Forward-deployed engineers at Palantir(25:23) Key principles of Palantir's success(30:00) Gotham and Foundry(36:58) The ontology concept(38:02) Life as a forward-deployed engineer(41:36) Balancing custom solutions and product vision(46:36) Advice on how to implement forward-deployed engineers(50:41) The current state of forward-deployed engineers at Palantir(53:15) The power of ingesting, cleaning and analyzing data(59:25) Hiring for mission-driven startups(01:05:30) What makes Palantir PMs different(01:10:00) The moral question of Palantir(01:16:03) Advice for new startups(01:21:12) AI corner(01:24:00) Contrarian corner(01:25:42) Lightning round and final thoughts—Referenced:• Reflections on Palantir: https://nabeelqu.co/reflections-on-palantir• Palantir: https://www.palantir.com/• Intercom: https://www.intercom.com/• Which companies produce the best product managers: https://www.lennysnewsletter.com/p/which-companies-produce-the-best• Gotham: https://www.palantir.com/platforms/gotham/• Foundry: https://www.palantir.com/platforms/foundry/• Peter Thiel on X: https://x.com/peterthiel• Alex Karp: https://en.wikipedia.org/wiki/Alex_Karp• Stephen Cohen: https://en.wikipedia.org/wiki/Stephen_Cohen_(entrepreneur)• Joe Lonsdale on LinkedIn: https://www.linkedin.com/in/jtlonsdale/• Tyler Cowen's website: https://tylercowen.com/• This Scandinavian City Just Won the Internet With Its Hilarious New Tourism Ad: https://www.afar.com/magazine/oslos-new-tourism-ad-becomes-viral-hit• Safe Superintelligence: https://ssi.inc/• Mira Murati on X: https://x.com/miramurati• Stripe: https://stripe.com/• Building product at Stripe: craft, metrics, and customer obsession | Jeff Weinstein (Product lead): https://www.lennysnewsletter.com/p/building-product-at-stripe-jeff-weinstein• Airbus: https://www.airbus.com/en• NIH: https://www.nih.gov/• Jupyter Notebooks: https://jupyter.org/• Shyam Sankar on LinkedIn: https://www.linkedin.com/in/shyamsankar/• Palantir Gotham for Defense Decision Making: https://www.youtube.com/watch?v=rxKghrZU5w8• Foundry 2022 Operating System Demo: https://www.youtube.com/watch?v=uF-GSj-Exms• SQL: https://en.wikipedia.org/wiki/SQL• Airbus A350: https://en.wikipedia.org/wiki/Airbus_A350• SAP: https://www.sap.com/index.html• Barry McCardel on LinkedIn: https://www.linkedin.com/in/barrymccardel/• Understanding ‘Forward Deployed Engineering' and Why Your Company Probably Shouldn't Do It: https://www.barry.ooo/posts/fde-culture• David Hsu on LinkedIn: https://www.linkedin.com/in/dvdhsu/• Retool's Path to Product-Market Fit—Lessons for Getting to 100 Happy Customers, Faster: https://review.firstround.com/retools-path-to-product-market-fit-lessons-for-getting-to-100-happy-customers-faster/• How to foster innovation and big thinking | Eeke de Milliano (Retool, Stripe): https://www.lennysnewsletter.com/p/how-to-foster-innovation-and-big• Looker: https://cloud.google.com/looker• Sorry, that isn't an FDE: https://tedmabrey.substack.com/p/sorry-that-isnt-an-fde• Glean: https://www.glean.com/• Limited Engagement: Is Tech Becoming More Diverse?: https://www.bkmag.com/2017/01/31/limited-engagement-creating-diversity-in-the-tech-industry/• Operation Warp Speed: https://en.wikipedia.org/wiki/Operation_Warp_Speed• Mark Zuckerberg testifies: https://www.businessinsider.com/facebook-ceo-mark-zuckerberg-testifies-congress-libra-cryptocurrency-2019-10• Anduril: https://www.anduril.com/• SpaceX: https://www.spacex.com/• Principles: https://nabeelqu.co/principles• Wispr Flow: https://wisprflow.ai/• Claude code: https://docs.anthropic.com/en/docs/agents-and-tools/claude-code/overview• Gemini Pro 2.5: https://deepmind.google/technologies/gemini/pro/• DeepMind: https://deepmind.google/• Latent Space newsletter: https://www.latent.space/• Swyx on x: https://x.com/swyx• Neural networks in chess programs: https://www.chessprogramming.org/Neural_Networks• AlphaZero: https://en.wikipedia.org/wiki/AlphaZero• The top chess players in the world: https://www.chess.com/players• Decision to Leave: https://www.imdb.com/title/tt12477480/• Oldboy: https://www.imdb.com/title/tt0364569/• Christopher Alexander: https://en.wikipedia.org/wiki/Christopher_Alexander—Recommended books:• The Technological Republic: Hard Power, Soft Belief, and the Future of the West: https://www.amazon.com/Technological-Republic-Power-Belief-Future/dp/0593798694• Zero to One: Notes on Startups, or How to Build the Future: https://www.amazon.com/Zero-One-Notes-Startups-Future/dp/0804139296• Impro: Improvisation and the Theatre: https://www.amazon.com/Impro-Improvisation-Theatre-Keith-Johnstone/dp/0878301178/• William Shakespeare: Histories: https://www.amazon.com/Histories-Everymans-Library-William-Shakespeare/dp/0679433120/• High Output Management: https://www.amazon.com/High-Output-Management-Andrew-Grove/dp/0679762884• Anna Karenina: https://www.amazon.com/Anna-Karenina-Leo-Tolstoy/dp/0143035002—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Jerry Colonna is a world-renowned executive coach, a former venture capitalist, and the co-founder and CEO of Reboot, an executive coaching firm that combines practical leadership development with deeper self-inquiry. With over 27 years of coaching experience, he has guided countless leaders through the challenges of scaling companies, building teams, and navigating the emotional complexities of leadership. Known for his radical-self-inquiry approach, Jerry helps leaders uncover the unconscious patterns that hold them back and empowers them to lead with authenticity, compassion, and clarity.In our conversation, we cover:1. A powerful question that unlocks self-awareness: “How have I been complicit in creating the conditions I say I don't want?”2. Jerry's foundational equation for leadership success: practical skills + radical self-inquiry + shared experiences = enhanced leadership and resilience3. Why teams most often fail (hint: it's not lack of talent or strategy)4. How busyness often masks deeper issues of self-worth5. Why a “growth mindset” can be problematic6. The importance of legacy and what it means to live a meaningful life7. The role of AI in self-inquiry and how tools like ChatGPT can help uncover blind spots8. Jerry's advice for navigating the unsettling rise of AI and its implications for leadership and humanity—Brought to you by:Eppo—Run reliable, impactful experimentsContentsquare—Create better digital experiencesOneSchema—Import CSV data 10x faster—Where to find Jerry Colonna:• X: https://x.com/jerrycolonna• LinkedIn: https://www.linkedin.com/in/jerry-colonna-reboot/• Website: https://reunion.reboot.io/—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Jerry Colonna(04:12) Jerry's key question(06:55) The equation for great leadership(09:37) The big lie of success and happiness(12:12) The consciousness hack(15:56) Getting over the fear of consequences(20:23) The problem with bypassing our childhood baggage(23:22) Radical self-inquiry: asking the tough questions(27:05) Shared experiences: the power of community(30:25) The trap of busyness and attachment(40:45) Understanding our own intentions(46:58) Legacy and purpose(55:43) Writing for self-discovery(57:12) The impact of AI on humanity(01:05:00) Turning a growth mindset into a fixed mindset(01:11:30) The role of radical self-inquiry in leadership(01:19:24) Final thoughts and reflections—Referenced:• Naropa University: https://www.naropa.edu/• Fitler Club: https://fitlerclub.com• Chris Fralic on LinkedIn: https://www.linkedin.com/in/chrisfralic/• Will Smith on the price of fame: ‘I have been deeply humbled and deeply inspired': https://www.today.com/popculture/news/will-smith-fame-rcna127830• Seth Godin's best tactics for building remarkable products, strategies, brands, and more: https://www.lennysnewsletter.com/p/seth-godins-tactics-for-building-remarkable-products• The life of Buddha: https://www.britannica.com/summary/Buddha-founder-of-Buddhism• 10% Happier with Dan Harris podcast: https://podcasts.apple.com/us/podcast/10-happier-with-dan-harris/id1087147821• Simon Sinek's website: https://simonsinek.com/• Mike Tyson Gives Morbid Response to Young Interviewer's Question About His “Legacy”: https://www.vibe.com/news/entertainment/mike-tyson-morbid-response-young-interviewer-legacy-1234944054/• Dan Shipper's post on X about asking ChatGPT for blind spots: https://x.com/danshipper/status/1910387987487318318• Evernote: https://evernote.com/• Claude: https://claude.ai• Peter Senge on X: https://x.com/petersenge• Carl Jung's quote: https://www.goodreads.com/quotes/44379-until-you-make-the-unconscious-conscious-it-will-direct-your• Parker Palmer on LinkedIn: https://www.linkedin.com/in/parker-j-palmer-5a92b110/• The unexamined life is not worth living: https://en.wikipedia.org/wiki/The_unexamined_life_is_not_worth_living—Recommended books:• Reboot: Leadership and the Art of Growing Up: https://www.amazon.com/Reboot-Leadership-Art-Growing-Up/dp/0062749536• Reunion: Leadership and the Longing to Belong: https://www.amazon.com/Reunion-Leadership-Longing-Jerry-Colonna/dp/0063142139• Born to Run: https://www.amazon.com/Born-Run-Bruce-Springsteen/dp/1501141511• 10% Happier: How I Tamed the Voice in My Head, Reduced Stress Without Losing My Edge, and Found Self-Help That Actually Works—A True Story: https://www.amazon.com/10-Happier-Self-Help-Actually-Works/dp/0062265431• Soldiers and Kings: Survival and Hope in the World of Human Smuggling: https://www.amazon.com/Soldiers-Kings-Survival-World-Smuggling/dp/0593298586• The Giving Tree: https://www.amazon.com/Giving-Tree-Shel-Silverstein/dp/0060256656/—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Scott Wu is the co-founder and CEO of Cognition, the company behind Devin—the world's first autonomous AI software engineer. Unlike other AI coding tools, Devin works like an autonomous engineer that you can interact with through Slack, Linear, and GitHub, just like with a remote engineer. With Scott's background in competitive programming and a previous AI-powered startup, Lunchclub, teaching AI to code has become his ultimate passion.What you'll learn:1. How a team of “Devins” are already producing 25% of Cognition's pull requests, and they are on track to hit 50% by year's end2. How each engineer on Cognition's 15-person engineering team works with about five Devins each3. How Devin has evolved from a “high school CS student” to a “junior engineer” over the past year4. Why engineering will shift from “bricklayers” to “architects”5. Why AI tools will lead to more engineering jobs rather than fewer6. How Devin creates its own wiki to understand and document complex codebases7. The eight pivots Cognition went through before landing on their current approach8. The cultural shifts required to successfully adopt AI engineers—Brought to you by:Enterpret—Transform customer feedback into product growthParagon—Ship every SaaS integration your customers wantAttio—The powerful, flexible CRM for fast-growing startups—Where to find Scott Wu:• X: https://x.com/scottwu46• LinkedIn: https://www.linkedin.com/in/scott-wu-8b94ab96/—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Scott Wu and Devin(09:13) Scaling and future prospects(10:23) Devin's origin story(17:26) The idea of Devin as a person(22:19) How a team of “Devins” are already producing 25% of Cognition's pull requests(25:17) Important skills in the AI era(30:21) How Cognition's engineering team works with Devin's(34:37) Live demo(42:20) Devin's codebase integration(44:50) Automation with Linear(46:53) What Devin does best(52:56) The future of AI in software engineering(57:13) Moats and stickiness in AI(01:01:57) The tech that enables Devin(01:04:14) AI will be the biggest technology shift of our lives(01:07:25) Adopting Devin in your company(01:15:13) Startup wisdom and hiring practices(01:22:32) Lightning round and final thoughts—Referenced:• Devin: https://devin.ai/• GitHub: https://github.com/• Linear: https://linear.app/• Waymo: https://waymo.com/• GitHub Copilot: https://github.com/features/copilot• Cursor: https://www.cursor.com/• Anysphere: https://anysphere.inc/• Bolt: https://bolt.new/• StackBlitz: https://stackblitz.com/• Cognition: https://cognition.ai/• v0: https://v0.dev/• Vercel: https://vercel.com/• Everyone's an engineer now: Inside v0's mission to create a hundred million builders | Guillermo Rauch (founder and CEO of Vercel, creators of v0 and Next.js): https://www.lennysnewsletter.com/p/everyones-an-engineer-now-guillermo-rauch• Inside Bolt: From near-death to ~$40m ARR in 5 months—one of the fastest-growing products in history | Eric Simons (founder and CEO of StackBlitz): https://www.lennysnewsletter.com/p/inside-bolt-eric-simons• Assembly: https://en.wikipedia.org/wiki/Assembly_language• Pascal: https://en.wikipedia.org/wiki/Pascal_(programming_language)• Python: https://www.python.org/• Jevons paradox: https://en.wikipedia.org/wiki/Jevons_paradox• Datadog: https://www.datadoghq.com/• Bending the universe in your favor | Claire Vo (LaunchDarkly, Color, Optimizely, ChatPRD): https://www.lennysnewsletter.com/p/bending-the-universe-in-your-favor• OpenAI's CPO on how AI changes must-have skills, moats, coding, startup playbooks, more | Kevin Weil (CPO at OpenAI, ex-Instagram, Twitter): https://www.lennysnewsletter.com/p/kevin-weil-open-ai• Behind the product: Replit | Amjad Masad (co-founder and CEO): https://www.lennysnewsletter.com/p/behind-the-product-replit-amjad-masad• Windsurf: https://windsurf.com/• COBOL: https://en.wikipedia.org/wiki/COBOL• Fortran: https://en.wikipedia.org/wiki/Fortran• Magic the Gathering: https://magic.wizards.com/en• Aura frames: https://auraframes.com/• AirPods: https://www.apple.com/airpods/• Steven Hao on LinkedIn: https://www.linkedin.com/in/steven-hao-160b9638/• Walden Yan on LinkedIn: https://www.linkedin.com/in/waldenyan/—Recommended books:• How to Win Friends & Influence People: https://www.amazon.com/How-Win-Friends-Influence-People/dp/0671027034• The Power Law: Venture Capital and the Making of the New Future: https://www.amazon.com/Power-Law-Venture-Capital-Making/dp/052555999X• The Great Gatsby: https://www.amazon.com/Great-Gatsby-F-Scott-Fitzgerald/dp/0743273567—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed. Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe

Michael Truell is the co-founder and CEO of Anysphere, the company behind Cursor—the fastest-growing AI code editor in the world, reaching $300 million in annual recurring revenue just two years after its launch. In this conversation, Michael shares his vision for the future, lessons learned, and advice for preparing for the fast-approaching AI future.What you'll learn:• Cursor's early pivot from automating CAD to automating code• Michael's vision for “what comes after code” and how programming will evolve• Why Cursor built their own custom AI models despite not starting there• Key lessons from Cursor's rapid growth• Why “taste” and logic design will become more valuable engineering skills than technical coding ability• Why the market for AI coding tools is much larger than people realize—and why there will likely be one dominant winner• Michael's advice for engineers and product teams preparing for the AI future—Brought to you by:Eppo—Run reliable, impactful experimentsVanta—Automate compliance. Simplify securityOneSchema—Import CSV data 10x faster—Where to find Michael Truell:• X: https://x.com/mntruell• LinkedIn: https://www.linkedin.com/in/michael-t-5b1bbb122/• Website: https://mntruell.com/—In this episode, we cover:(00:00) Introduction to Michael Truell and Cursor(04:20) What comes after code(08:32) The importance of taste(12:39) Cursor's origin story(18:31) Why they chose to build an IDE(22:39) Will everyone become engineering managers?(24:31) How they decided it was time to ship(26:45) Reflecting on Cursor's success(32:03) Counterintuitive lessons on building AI products(34:02) Inside Cursor's stack(38:42) Defensibility and market dynamics in AI(46:13) Tips for using Cursor(51:25) Hiring and building a strong team(59:10) Staying focused amid rapid AI advancements(01:02:31) Final thoughts and advice for aspiring AI innovators—Referenced:• Cursor: https://www.cursor.com/• Microsoft Copilot: https://copilot.microsoft.com/• Scaling laws for neural language models: https://openai.com/index/scaling-laws-for-neural-language-models/• MIT: https://www.mit.edu/• Telegram: https://telegram.org/• Signal: https://signal.org/• WhatsApp: https://www.whatsapp.com/• Devin: https://devin.ai/• Visual Studio Code: https://code.visualstudio.com/• Chromium: https://chromium.googlesource.com/chromium/src/base/• Exploring ChatGPT (GPT) Wrappers—What They Are and How They Work: https://learnprompting.org/blog/gpt_wrappers• OpenAI's CPO on how AI changes must-have skills, moats, coding, startup playbooks, more | Kevin Weil (CPO at OpenAI, ex-Instagram, Twitter): https://www.lennysnewsletter.com/p/kevin-weil-open-ai• Behind the founder: Marc Benioff: https://www.lennysnewsletter.com/p/behind-the-founder-marc-benioff• DALL-E 3: https://openai.com/index/dall-e-3/• Stable Diffusion 3: https://stability.ai/news/stable-diffusion-3—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed. Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe

Daniel Lereya, the Chief Product and Technology Officer at monday.com, shares how he and his team realized they were being outpaced by competitors and how that realization completely transformed how they operate and allowed them to build a global powerhouse, doing over $1 billion in ARR, with 245,000 customers worldwide.What you'll learn:1. How they used seemingly impossible goals, like building 25 new features in one month, to unlock bigger thinking on their team2. How sharing real-time metrics with the entire company—even during interviews—created a culture of accountability and alignment3. How focusing on impact, rather than just shipping features, has transformed the company's culture4. The story behind monday.com's decision to launch five new products simultaneously and how it redefined their market positioning5. How they use “traps” (timeboxed deadlines) to drive focus, avoid scope creep, and deliver faster6. Daniel's personal journey of navigating impostor syndrome and scaling challenges, and the mental models he uses to stay grounded and effective—Brought to you by:• Enterpret—Transform customer feedback into product growth• Airtable ProductCentral—Launch to new heights with a unified system for product development• Vanta—Automate compliance. Simplify security—Where to find Daniel Lereya:• LinkedIn: https://www.linkedin.com/in/daniel-lereya-aa487646/—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Daniel and monday.com(04:20) The pivotal moment: competitors shipping faster(08:50) Setting ambitious goals(17:44) Focusing on impact rather than features(27:07) Transforming your product quarterly(32:07) Scaling monday.com: challenges and strategies(39:14) How monday.com maintains transparency as a public company(45:40) The importance of taking risks(51:02) Counterintuitive lessons in product development(54:33) The value of timeboxing and deadlines(57:28) Embracing user feedback(59:54) Adapting leadership styles(01:04:43) Personal reflections on leadership(01:10:41) Handling crises and strategic planning(01:17:28) The role of AI in work and personal life(01:22:13) Final thoughts and lightning round—Referenced:• Monday.com: https://monday.com/• The basics of a monday.com board: https://support.monday.com/hc/en-us/articles/115005317249-The-basics-of-a-board• Eran Zinman on LinkedIn: https://www.linkedin.com/in/eranzinman/• Roy Mann on LinkedIn: https://www.linkedin.com/in/manroy/• Tal Harari on LinkedIn: https://www.linkedin.com/in/tal-harari-a2515215/• Four-minute mile: https://en.wikipedia.org/wiki/Four-minute_mile• A better way to plan, build, and ship products | Ryan Singer (creator of “Shape Up,” early employee at 37signals): https://www.lennysnewsletter.com/p/shape-up-ryan-singer• Brian Chesky's new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach• AI blocks: https://support.monday.com/hc/en-us/articles/18433811274386-AI-Automation-blocks• Unpacking Amazon's unique ways of working | Bill Carr (author of Working Backwards): https://www.lennysnewsletter.com/p/unpacking-amazons-unique-ways-of• Behind the founder: Drew Houston (Dropbox): https://www.lennysnewsletter.com/p/behind-the-founder-drew-houston-dropbox• SpaceX: https://www.spacex.com/• Why and how to lead with transparency: https://monday.com/blog/monday-insights/may-30th/• How to win in the AI era: Ship a feature every week, embrace technical debt, ruthlessly cut scope, and create magic your competitors can't copy | Gaurav Misra (CEO and co-founder of Captions): https://www.lennysnewsletter.com/p/how-to-win-in-the-ai-era-gaurav-misra• This Week #5: Overcoming impostor syndrome, introducing growth to an org, and how to partner with your data scientist: https://www.lennysnewsletter.com/p/this-week-overcoming-impostor-syndrome• Sheryl Sandberg on LinkedIn: https://www.linkedin.com/in/sheryl-sandberg-5126652/• Bryan Johnson on LinkedIn: https://www.linkedin.com/in/bryanrjohnson/• ChatGPT: https://chatgpt.com/• Cursor: https://www.cursor.com/• How to build deeper, more robust relationships | Carole Robin (Stanford GSB professor, “Touchy Feely”): https://www.lennysnewsletter.com/p/build-robust-relationships-carole-robin• FIFA 22: https://store.playstation.com/en-us/concept/10002538/• Formula 1: Drive to Survive on Netflix: https://www.netflix.com/title/80204890• Google Photos: https://photos.google.com/—Recommended books:• Shape Up: Stop Running in Circles and Ship Work that Matters: https://basecamp.com/shapeup• Working Backwards: Insights, Stories, and Secrets from Inside Amazon: https://www.amazon.com/Working-Backwards-Insights-Stories-Secrets/dp/1250267595• No Rules Rules: Netflix and the Culture of Reinvention: https://www.amazon.com/No-Rules-Netflix-Culture-Reinvention/dp/1984877860• Nonviolent Communication: A Language of Life: Life-Changing Tools for Healthy Relationships: https://www.amazon.com/Nonviolent-Communication-Language-Life-Changing-Relationships/dp/189200528X/—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed. Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe

AI is rapidly changing how we live and work. It's exciting, but also overwhelming. If you're struggling to keep up, and wondering how to actually use these magical new tools to improve the quality and efficiency of your work, I'm thrilled to introduce How I AI with Claire Vo—the first ever new podcast under the Lenny's Podcast network. Claire is an engineer, three-time CPO, and AI builder. In each episode, her guest shows you a specific, practical, and impactful way they've learned to use AI. Forget theoretical debates—this podcast is about real, valuable use cases. Expect 30-minute episodes, live demos, and tips/tricks/workflows you can implement immediately. Whether you're building products, leading teams, or just looking to level up your AI skills, How I AI is for you.—SUBSCRIBE TO THE SHOW→ YouTube: ⁠https://www.youtube.com/channel/UCRYY7IEbkHLH_ScJCu9eWDQ⁠→ Spotify: ⁠https://open.spotify.com/show/4aRP2XSavdtrLG5FZoonOK→ Apple: https://podcasts.apple.com/us/podcast/how-i-ai/id1809663079 Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe

Varun Mohan is the co-founder and CEO of Windsurf (formerly Codeium), an AI-powered development environment (IDE) that has been used by over 1 million developers in just four months and has quickly emerged as a leader in transforming how developers build software. Prior to finding success with Windsurf, the company pivoted twice—first from GPU virtualization infrastructure to an IDE plugin, and then to their own standalone IDE.In this conversation, you'll learn:1. Why Windsurf walked away from a profitable GPU infrastructure business and bet the company on helping engineers code2. The surprising UI discovery that tripled adoption rates overnight.3. The secret behind Windsurf's B2B enterprise plan, and why they invested early in an 80-person sales team despite conventional startup wisdom.4. How non-technical staff at Windsurf built their own custom tools instead of purchasing SaaS products, saving them over $500k in software costs5. Why Varun believes 90% of code will be AI-generated, but engineering jobs will actually increase6. How training on millions of incomplete code samples gives Windsurf an edge, and creates a moat long-term7. Why agency is the most undervalued and important skill in the AI era—Brought to you by:• Brex—The banking solution for startups• Productboard—Make products that matter• Coda—The all-in-one collaborative workspace—Where to find Varun Mohan:• X: https://x.com/_mohansolo• LinkedIn: https://www.linkedin.com/in/varunkmohan/—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Varun's background(03:57) Building and scaling Windsurf(12:58) Windsurf: The new purpose-built IDE to harness magic(17:11) The future of engineering and AI(21:30) Skills worth investing in(23:07) Hiring philosophy and company culture(35:22) Sales strategy and market position(39:37) JetBrains vs. VS Code: extensibility and enterprise adoption(41:20) Live demo: building an Airbnb for dogs with Windsurf(42:46) Tips for using Windsurf effectively(46:38) AI's role in code modification and review(48:56) Empowering non-developers to build custom software(54:03) Training Windsurf(01:00:43) Windsurf's unique team structure and product strategy(01:06:40) The importance of continuous innovation(01:08:57) Final thoughts and advice for aspiring developers—Referenced:• Windsurf: https://windsurf.com/• VS Code: https://code.visualstudio.com/• JetBrains: https://www.jetbrains.com/• Eclipse: https://eclipseide.org/• Visual Studio: https://visualstudio.microsoft.com/• Vim: https://www.vim.org/• Emacs: https://www.gnu.org/software/emacs/• Lessons from a two-time unicorn builder, 50-time startup advisor, and 20-time company board member | Uri Levine (co-founder of Waze): https://www.lennysnewsletter.com/p/lessons-from-uri-levine• IntelliJ: https://www.jetbrains.com/idea/• Julia: https://julialang.org/• Parallel computing: https://en.wikipedia.org/wiki/Parallel_computing• Douglas Chen on LinkedIn: https://www.linkedin.com/in/douglaspchen/• Carlos Delatorre on LinkedIn: https://www.linkedin.com/in/cadelatorre/• MongoDB: https://www.mongodb.com/• Cursor: https://www.cursor.com/• GitHub Copilot: https://github.com/features/copilot• Llama: https://www.llama.com/• Mistral: https://mistral.ai/• Building Lovable: $10M ARR in 60 days with 15 people | Anton Osika (CEO and co-founder): https://www.lennysnewsletter.com/p/building-lovable-anton-osika• Inside Bolt: From near-death to ~$40m ARR in 5 months—one of the fastest-growing products in history | Eric Simons (founder & CEO of StackBlitz): https://www.lennysnewsletter.com/p/inside-bolt-eric-simons• Behind the product: Replit | Amjad Masad (co-founder and CEO): https://www.lennysnewsletter.com/p/behind-the-product-replit-amjad-masad• React: https://react.dev/• Sonnet: https://www.anthropic.com/claude/sonnet• OpenAI: https://openai.com/• FedRamp: https://www.fedramp.gov/• Dario Amodei on LinkedIn: https://www.linkedin.com/in/dario-amodei-3934934/• Amdahl's law: https://en.wikipedia.org/wiki/Amdahl%27s_law• How to win in the AI era: Ship a feature every week, embrace technical debt, ruthlessly cut scope, and create magic your competitors can't copy | Gaurav Misra (CEO and co-founder of Captions): https://www.lennysnewsletter.com/p/how-to-win-in-the-ai-era-gaurav-misra—Recommended book:• Fall in Love with the Problem, Not the Solution: A Handbook for Entrepreneurs: https://www.amazon.com/Fall-Love-Problem-Solution-Entrepreneurs/dp/1637741987—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed. Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe

Guillermo Rauch is the founder and CEO of Vercel, creators of v0 (one of the most popular AI app building tools), and the mind behind foundational JavaScript frameworks like Next.js and Socket.io. An open source pioneer and legendary engineer, Guillermo has built tools that power some of the internet's most innovative products, including Midjourney, Grok, and Notion. His mission is to democratize product creation, expanding the pool of potential builders from 5 million developers to over 100 million people worldwide. In this episode, you'll learn:1. How AI will radically speed up product development—and the three critical skills PMs and engineers should master now to stay ahead2. Why the future of building apps is shifting toward prompts instead of code, and how that affects traditional product teams3. Specific ways to improve your design “taste,” plus practical tips to consistently create beautiful, user-loved products4. How Guillermo built a powerful app in under two hours for $20 (while flying and using plane Wi-Fi) that would normally take weeks and thousands of dollars in engineering time5. The exact strategies Vercel uses internally to leverage AI tools like v0 and Cursor, enabling their team of 600 to ship faster and better than ever before6. Guillermo's actionable advice on increasing your product quality through rapid iteration, real-world user feedback, and creating intentional “exposure hours” for your team—Brought to you by:• WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs• Vanta — Automate compliance. Simplify security• LinkedIn Ads—Reach professionals and drive results for your business—Where to find Guillermo Rauch:• X: https://x.com/rauchg• LinkedIn: https://www.linkedin.com/in/rauchg/• Website: https://rauchg.com/—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Guillermo Rauch(04:43) v0's mission(07:03) The impact and growth of v0(15:54) The future of product development with AI(19:05) Empowering engineers and product builders(24:01) Skills for the future: coding, math, and eloquence(35:05) v0 in action: real-world applications(36:40) Tips for using v0 effectively(45:46) Core skills for building AI apps(49:44) Live demo(59:45) Understanding how AI thinks(01:04:35) AI integration and future prospects(01:07:22) Building taste(01:13:43) Limitations of v0(01:16:54) Improving the design of your product(01:20:09) The secret to product quality(01:22:35) Vercel's AI-driven development(01:25:43) Guillermo's vision for the future—Referenced:• v0: https://v0.dev/• Vercel: https://vercel.com/• GitHub: https://github.com/• Cursor: https://www.cursor.com/• Next.js Framework: https://nextjs.org/• Claude: https://claude.ai/new• Grok: https://x.ai/• Midjourney: https://www.midjourney.com• SocketIO: https://socket.io/• Notion's lost years, its near collapse during Covid, staying small to move fast, the joy and suffering of building horizontal, more | Ivan Zhao (CEO and co-founder): https://www.lennysnewsletter.com/p/inside-notion-ivan-zhao• Notion: https://www.notion.com/• Automattic: https://automattic.com/• Inside Bolt: From near-death to ~$40m ARR in 5 months—one of the fastest-growing products in history | Eric Simons (founder & CEO of StackBlitz): https://www.lennysnewsletter.com/p/inside-bolt-eric-simons• v0 Community: https://v0.dev/chat/community• Figma: https://www.figma.com/• Git Commit: https://www.atlassian.com/git/tutorials/saving-changes/git-commit• What are Artifacts and how do I use them?: https://support.anthropic.com/en/articles/9487310-what-are-artifacts-and-how-do-i-use-them• Design Engineering at Vercel: https://vercel.com/blog/design-engineering-at-vercel• CSS: https://en.wikipedia.org/wiki/CSS• Tailwind: https://tailwindcss.com/• Wordcel / Shape Rotator / Mathcel: https://knowyourmeme.com/memes/wordcel-shape-rotator-mathcel• Steve Jobs's Ultimate Lesson for Companies: https://hbr.org/2011/08/steve-jobss-ultimate-lesson-fo• Bloom Hackathon: https://bloom.build/• Expenses Should Do Themselves | Saquon Barkley x Ramp (Super Bowl Ad): https://www.youtube.com/watch?v=p1Tgsy7D0Jg• Velocity over everything: How Ramp became the fastest-growing SaaS startup of all time | Geoff Charles (VP of Product): https://www.lennysnewsletter.com/p/velocity-over-everything-how-ramp• JavaScript: https://www.javascript.com/• React: https://react.dev/• Mapbox: https://www.mapbox.com/• Leaflet: https://leafletjs.com/• Escape hatches: https://react.dev/learn/escape-hatches• Supreme: https://supreme.com/• Shadcn: https://ui.shadcn.com/• Charles Schwab: https://www.schwab.com/• Fortune: https://fortune.com/• Semafor: https://www.semafor.com/• AI SDK: https://sdk.vercel.ai/• DeepSeek: https://www.deepseek.com/• Stripe: https://stripe.com/• Vercel templates: https://vercel.com/templates• GC AI: https://getgc.ai/• OpenEvidence: https://www.openevidence.com/• Paris Fashion Week: https://www.fhcm.paris/en/paris-fashion-week• Guillermo's post on X about making great products: https://x.com/rauchg/status/1887314115066274254• Everybody Can Cook billboard: https://www.linkedin.com/posts/evilrabbit_activity-7242975574242037760-uRW9/• Ratatouille: https://www.imdb.com/title/tt0382932/—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed. Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe

Kevin Weil is the chief product officer at OpenAI, where he oversees the development of ChatGPT, enterprise products, and the OpenAI API. Prior to OpenAI, Kevin was head of product at Twitter, Instagram, and Planet, and was instrumental in the development of the Libra (later Novi) cryptocurrency project at Facebook.In this episode, you'll learn:1. How OpenAI structures its product teams and maintains agility while developing cutting-edge AI2. The power of model ensembles—using multiple specialized models together like a company of humans with different skills3. Why writing effective evals (AI evaluation tests) is becoming a critical skill for product managers4. The surprisingly enduring value of chat as an interface for AI, despite predictions of its obsolescence5. How “vibe coding” is changing how companies operate6. What OpenAI looks for when hiring product managers (hint: high agency and comfort with ambiguity)7. “Model maximalism” and why today's AI is the worst you'll ever use again8. Practical prompting techniques that improve AI interactions, including example-based prompting—Brought to you by:• Eppo—Run reliable, impactful experiments• Persona—A global leader in digital identity verification• OneSchema—Import CSV data 10x faster—Where to find Kevin Weil:• X: https://x.com/kevinweil• LinkedIn: https://www.linkedin.com/in/kevinweil/—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Kevin's background(04:06) OpenAI's new image model(06:52) The role of chief product officer at OpenAI(10:18) His recruitment story and joining OpenAI(17:20) The importance of evals in AI(24:59) Shipping quickly and consistently(28:34) Product reviews and iterative deployment(39:35) Chat as an interface for AI(43:59) Collaboration between researchers and product teams(46:41) Hiring product managers at OpenAI(48:45) Embracing ambiguity in product management(51:41) The role of AI in product teams(53:21) Vibe coding and AI prototyping(55:55) The future of product teams and fine-tuned models(01:04:36) AI in education(01:06:42) Optimism and concerns about AI's future(01:16:37) Reflections on the Libra project(01:20:37) Lightning round and final thoughts—Referenced:• OpenAI: https://openai.com/• The AI-Generated Studio Ghibli Trend, Explained: https://www.forbes.com/sites/danidiplacido/2025/03/27/the-ai-generated-studio-ghibli-trend-explained/• Introducing 4o Image Generation: https://openai.com/index/introducing-4o-image-generation/• Waymo: https://waymo.com/• X: https://x.com• Facebook: https://www.facebook.com/• Instagram: https://www.instagram.com/• Planet: https://www.planet.com/• Sam Altman on X: https://x.com/sama• A conversation with OpenAI's CPO Kevin Weil, Anthropic's CPO Mike Krieger, and Sarah Guo: https://www.youtube.com/watch?v=IxkvVZua28k• OpenAI evals: https://github.com/openai/evals• Deep Research: https://openai.com/index/introducing-deep-research/• Ev Williams on X: https://x.com/ev• OpenAI API: https://platform.openai.com/docs/overview• Dwight Eisenhower quote: https://www.brainyquote.com/quotes/dwight_d_eisenhower_164720• Inside Bolt: From near-death to ~$40m ARR in 5 months—one of the fastest-growing products in history | Eric Simons (founder & CEO of StackBlitz): https://www.lennysnewsletter.com/p/inside-bolt-eric-simons• StackBlitz: https://stackblitz.com/• Claude 3.5 Sonnet: https://www.anthropic.com/news/claude-3-5-sonnet• Anthropic: https://www.anthropic.com/• Four-minute mile: https://en.wikipedia.org/wiki/Four-minute_mile• Chad: https://chatgpt.com/g/g-3F100ZiIe-chad-open-a-i• Dario Amodei on LinkedIn: https://www.linkedin.com/in/dario-amodei-3934934/• Figma: https://www.figma.com/• Julia Villagra on LinkedIn: https://www.linkedin.com/in/juliavillagra/• Andrej Karpathy on X: https://x.com/karpathy• Silicon Valley CEO says ‘vibe coding' lets 10 engineers do the work of 100—here's how to use it: https://fortune.com/2025/03/26/silicon-valley-ceo-says-vibe-coding-lets-10-engineers-do-the-work-of-100-heres-how-to-use-it/• Cursor: https://www.cursor.com/• Windsurf: https://codeium.com/windsurf• GitHub Copilot: https://github.com/features/copilot• Patrick Srail on X: https://x.com/patricksrail• Khan Academy: https://www.khanacademy.org/• CK-12 Education: https://www.ck12.org/• Sora: https://openai.com/sora/• Sam Altman's post on X about creative writing: https://x.com/sama/status/1899535387435086115• Diem (formerly known as Libra): https://en.wikipedia.org/wiki/Diem_(digital_currency)• Novi: https://about.fb.com/news/2020/05/welcome-to-novi/• David Marcus on LinkedIn: https://www.linkedin.com/in/dmarcus/• Peter Zeihan on X: https://x.com/PeterZeihan• The Wheel of Time on Prime Video: https://www.amazon.com/Wheel-Time-Season-1/dp/B09F59CZ7R• Top Gun: Maverick on Prime Video: https://www.amazon.com/Top-Gun-Maverick-Joseph-Kosinski/dp/B0DM2LYL8G• Thinking like a gardener not a builder, organizing teams like slime mold, the adjacent possible, and other unconventional product advice | Alex Komoroske (Stripe, Google): https://www.lennysnewsletter.com/p/unconventional-product-advice-alex-komoroske• MySQL: https://www.mysql.com/—Recommended books:• Co-Intelligence: Living and Working with AI: https://www.amazon.com/Co-Intelligence-Living-Working-Ethan-Mollick/dp/059371671X• The Accidental Superpower: Ten Years On: https://www.amazon.com/Accidental-Superpower-Ten-Years/dp/1538767341• Cable Cowboy: https://www.amazon.com/Cable-Cowboy-Malone-Modern-Business/dp/047170637X—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed. Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe

Wes Kao is an entrepreneur, coach, and advisor. She co-founded the live learning platform Maven, backed by First Round and a16z. Before Maven, Wes co-created the altMBA with best-selling author Seth Godin. Today, Wes teaches a popular course on executive communication and influence. Through her course and one-on-one coaching, she's helped thousands of operators, founders, and product leaders master the art of influence through clear, compelling communication. Known for her surgical writing style and no-BS frameworks, Wes returns to the pod to deliver a tactical master class on becoming a sharper, more persuasive communicator—at work, in meetings, and across your career.What you'll learn:1. The #1 communication mistake leaders make—and Wes's proven fix to instantly gain buy-in2. Wes's MOO (Most Obvious Objection) framework to consistently anticipate and overcome pushback in meetings3. How to master concise communication—including Wes's tactical approach for brevity without losing meaning4. The art of executive presence: actionable strategies for conveying confidence and clarity, even under pressure5. The “sales, then logistics” framework—and why your ideas keep getting ignored without it6. The power of “signposting”—and why executives skim your docs without it7. Exactly how to give feedback that works—Wes's “strategy, not self-expression” principle to drive behavior change without friction8. Practical ways to instantly improve your writing, emails, and Slack messages—simple techniques Wes teaches executives9. Managing up like a pro: Wes's clear, practical advice on earning trust, building credibility, and aligning with senior leaders10. Career accelerators: specific habits and tactics from Wes for growing your influence, advancing your career, and standing out11. Real-world communication examples—Wes breaks down real scenarios she's solved, providing step-by-step solutions you can copy today—Brought to you by:• WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs• Vanta—Automate compliance. Simplify security• Coda—The all-in-one collaborative workspace—Where to find Wes Kao:• LinkedIn: https://www.linkedin.com/in/weskao/• Website: https://www.weskao.com/• Maven course: https://maven.com/wes-kao/executive-communication-influence—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Wes Kao(05:34) Working with Wes(06:58) The importance of communication(10:44) Sales before logistics(18:20) Being concise(24:31) Books to help you become a better writer(27:30) Signposting and formatting(32:05) How to develop and practice your communication skills(40:41) Slack communication(42:23) Confidence in communication(50:17) The MOO framework(54:00) Staying calm in high-stakes conversations(57:36) Which tactic to start with(58:53) Effective tactics for managing up(01:04:53) Giving constructive feedback: strategy, not self-expression(01:09:39) Delegating effectively while maintaining high standards(01:16:36) The swipe file: collecting inspiration for better communication(01:19:59) Leveraging AI for better communication(01:22:01) Lightning round—Referenced:• Persuasive communication and managing up | Wes Kao (Maven, Seth Godin, Section4): https://www.lennysnewsletter.com/p/persuasive-communication-wes-kao• Making Meta | Andrew ‘Boz' Bosworth (CTO): https://www.lennysnewsletter.com/p/making-meta-andrew-boz-bosworth-cto• Communication is the job: https://boz.com/articles/communication-is-the-job• Maven: https://maven.com/• Sales, not logistics: https://newsletter.weskao.com/p/sales-not-logistics• How to be more concise: https://newsletter.weskao.com/p/how-to-be-concise• Signposting: How to reduce cognitive load for your reader: https://newsletter.weskao.com/p/sign-posting-how-to-reduce-cognitive• Airbnb's Vlad Loktev on embracing chaos, inquiry over advocacy, poking the bear, and “impact, impact, impact” (Partner at Index Ventures, Airbnb GM/VP Product): https://www.lennysnewsletter.com/p/impact-impact-impact-vlad-loktev• Tone and words: Use accurate language: https://newsletter.weskao.com/p/tone-and-words-use-accurate-language• Quote by Joan Didion: https://www.goodreads.com/quotes/264509-i-don-t-know-what-i-think-until-i-write-it• Strategy, not self-expression: How to decide what to say when giving feedback: https://newsletter.weskao.com/p/strategy-not-self-expression• Tobi Lütke's leadership playbook: Playing infinite games, operating from first principles, and maximizing human potential (founder and CEO of Shopify): https://www.lennysnewsletter.com/p/tobi-lutkes-leadership-playbook• The CEDAF framework: Delegating gets easier when you get better at explaining your ideas: https://newsletter.weskao.com/p/delegating-and-explaining• Swipe file: https://en.wikipedia.org/wiki/Swipe_file• Apple Notes: https://apps.apple.com/us/app/notes/id1110145109• Claude: https://claude.ai/new• ChatGPT: https://chatgpt.com/• Arianna Huffington's phone bed charging station (Oak): https://www.amazon.com/Arianna-Huffingtons-Phone-Charging-Station/dp/B079C5DBF4?th=1• The Harlan Coben Collection on Netflix: https://www.netflix.com/browse/genre/81180221• Oral-B Pro 1000 rechargeable electric toothbrush: https://www.amazon.com/dp/B003UKM9CO/• The Best Electric Toothbrush: https://www.nytimes.com/wirecutter/reviews/best-electric-toothbrush/• Glengarry Glen Ross on Prime Video: https://www.amazon.com/Glengarry-Glen-Ross-James-Foley/dp/B002NN5F7A• 1,000,000: https://www.lennysnewsletter.com/p/1000000—Recommended books:• On Writing Well: The Classic Guide to Writing Nonfiction: https://www.amazon.com/Writing-Well-Classic-Guide-Nonfiction/dp/0060891548/• Stein on Writing: A Master Editor of Some of the Most Successful Writers of Our Century Shares His Craft Techniques and Strategies: https://www.amazon.com/Stein-Writing-Successful-Techniques-Strategies/dp/0312254210/• On Writing: A Memoir of the Craft: https://www.amazon.com/Writing-Memoir-Craft-Stephen-King/dp/1982159375• Several Short Sentences About Writing: https://www.amazon.com/Several-Short-Sentences-About-Writing/dp/0307279413/• High Output Management: https://www.amazon.com/High-Output-Management-Andrew-Grove/dp/0679762884• Your Brain at Work: Strategies for Overcoming Distraction, Regaining Focus, and Working Smarter All Day Long: https://www.amazon.com/Your-Brain-Work-Revised-Updated/dp/0063003155/—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed. Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe