Lenny's Podcast: Product | Career | Growth

Lenny Rachitsky

Interviews with world-class product leaders and growth experts to uncover concrete, actionable, and tactical advice to help you build, launch, and grow your own product.

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20 episodes
Updated July 26

Episodes20

Newest first

July 26 · 1 hr 33 min
Anthropic’s first technical PM on token maxing, the jagged edge, and living in the future | Dianne Penn
Dianne Penn is Head of Product for Anthropic’s AI Research and Labs teams. She joined in 2023 as Anthropic’s first technical product manager, when the entire product team was five engineers, and has since helped ship every model from Claude 2 through Fable, and helped incubate Claude Code, MCP, Skills, computer use, tool use, and reasoning. Before Anthropic, she helped build Alexa’s AI at Amazon and, before that, traded high-yield bonds at JP Morgan Chase. In our in-depth conversation, we discuss: 1. What Anthropic’s early days were like 2. The inflection points that turned Anthropic from an underdog into the fastest-growing company in history 3. How exactly Claude got so good at coding 4. The eval-driven development loop her team is pioneering 5. How to find joy in AI when everything is moving this fast 6. Why Claude’s willingness to push back is key to its success 7. Where human judgment remains irreplaceable — Brought to you by: WorkOS—Make your app enterprise-ready, with SSO, SCIM, RBAC, and more Mercury—Radically different banking, now with Command — Episode transcript: https://www.lennysnewsletter.com/p/anthropics-first-technical-pm-on — Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0 — Where to find Dianne Penn: • LinkedIn: linkedin.com/in/dianne-na-penn — 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 (02:31) Early Anthropic days (08:55) Big milestones (13:50) Inside the exponential (20:02) Token maxing (23:30) Anthropic Labs and the incubation model (27:30) How the research role works (31:35) How to become a top researcher (35:18) Frontier model safeguards (39:38) Hiring in the AI era (44:16) Building an eval set (47:48) Evals vs PRDs (49:55) The importance of hands-on leadership (52:46) Finding joy in AI (58:10) How Dianne uses Claude (01:01:05) Avoiding overreliance on AI (01:03:50) The constitution that makes Claude better (01:07:11) AI writing and verification (01:11:40) Where human brains will continue to be valuable (01:14:10) Navigating AI with kids (01:16:26) Alignment, the future of the PM role, and burnout (01:21:54) Lightning round and final thoughts — Referenced: • Anthropic: https://www.anthropic.com • Golden Gate Claude: https://www.anthropic.com/news/golden-gate-claude • Dario Amodei’s website: https://darioamodei.com • Scaling Laws and Interpretability of Learning from Repeated Data: https://www.anthropic.com/research/scaling-laws-and-interpretability-of-learning-from-repeated-data • Tokenmaxxing: How Top Builders Use AI To Do The Work Of 400 Engineers: https://www.ycombinator.com/library/Pa-tokenmaxxing-how-top-builders-use-ai-to-do-the-work-of-400-engineers • Garry Tan on X: https://x.com/garrytan • 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 • Anthropic’s CPO on what comes next | Mike Krieger (co-founder of Instagram): https://www.lennysnewsletter.com/p/anthropics-cpo-heres-what-comes-next • Introducing Labs: https://www.anthropic.com/news/introducing-anthropic-labs • Louis CK | about airplane Wi Fi: https://www.youtube.com/watch?v=me4BZBsHwZs • What happens after coding is solved? | Fiona Fung (Manager of the Claude Code and Cowork Teams): https://www.lennysnewsletter.com/p/building-the-most-ai-pilled-engineering • The Anthropic Hive Mind: https://steve-yegge.medium.com/the-anthropic-hive-mind-d01f768f3d7b • How to build a company that withstands any era | Eric Ries, Lean Startup author: https://www.lennysnewsletter.com/p/how-to-build-a-company-that-withstands • Fallout on Prime Video: https://www.amazon.com/dp/B0CN4GGGQ2 • Fallout (video game): https://fallout.bethesda.net • Claude Tag: https://www.anthropic.com/news/introducing-claude-tag — Recommended books: • Crucial Conversations: Tools for Talking When Stakes Are High: https://www.amazon.com/dp/0071771328 • How to Raise an Adult: Break Free of the Overparenting Trap and Prepare Your Kid for Success: https://www.amazon.com/How-Raise-Adult-Overparenting-Prepare/dp/1627791779 • Incorruptible: Why Good Companies Go Bad... and How Great Companies Stay Great: https://www.amazon.com/dp/B0FWZZBPZB — 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
July 19 · 1 hr 12 min
Why Netflix is betting on systems thinkers—not specialists—in the AI era | Elizabeth Stone (CPTO)
Elizabeth Stone is the Chief Product and Technology Officer (CPTO) at Netflix, where she oversees Engineering, Product, and Design. Since her first appearance on the podcast two years ago—which remained my second-most-popular episode for more than a year—she has expanded her role to lead product, in addition to engineering. Before Netflix, Elizabeth was VP of Science at Lyft, Chief Operating Officer at Nuna, an economist at Analysis Group, and a trader at Merrill Lynch. In our in-depth conversation, we discuss: 1. Why “systems thinking” is now the most important skill she looks for 2. How to manage the flood of AI-generated output without losing quality or signal 3. How Netflix thinks about AI fluency as a universal expectation rather than a level-specific skill 4. What “excellence as an operating system” means — Brought to you by: WorkOS—Make your app enterprise-ready, with SSO, SCIM, RBAC, and more: https://workos.com/lenny Mercury—Radically different banking, now with Command: https://mercury.com/command?utm_source=lennys&utm_medium=sponsored_newsletter&utm_campaign=26q3_brand_campaign — Episode transcript: https://www.lennysnewsletter.com/p/netflix-cpto-on-ai-and-the-future — Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0 — Where to find Elizabeth Stone: • LinkedIn: https://www.linkedin.com/in/elizabeth-stone-608a754 — 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 (02:25) AI and role confusion: the storming phase before the forming phase (07:36) How roles have changed in the past two and a half years (11:55) Will functions survive? The case for craft specialism (13:26) What Netflix is hiring more of—and less of (17:22) Why systems thinking is the rising skill across every function (20:20) Is the design process dead? (22:08) Skills trending down (28:33) AI fluency and Netflix’s career ladder overlay (31:00) AI use cases beyond coding (35:12) Netflix’s AI history (38:36) Excellence as an operating system (41:11) The pillars of the excellence OS (46:41) The keeper’s test—and why it’s mostly a positive conversation (50:21) Attracting top talent in the age of frontier AI labs (52:54) Junior talent, craft mastery, and the mentorship question (56:25) Where engineering goes in 5 to 10 years (59:45) The future of entertainment: beyond film and TV (1:02:18) AI in Hollywood: Netflix’s creator-enablement position (1:06:15) Lightning round and final thoughts — Referenced: • How Netflix builds a culture of excellence | Elizabeth Stone (CTO): https://www.lennysnewsletter.com/p/how-netflix-builds-a-culture-of-excellence • Brian Chesky’s new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach • The design process is dead. Here’s what’s replacing it. | Jenny Wen (head of design at Claude): https://www.lennysnewsletter.com/p/the-design-process-is-dead • Claude Code: https://www.anthropic.com/product/claude-code • Claude Cowork: https://www.anthropic.com/product/claude-cowork • Netflix’s “Keeper Test” and Why You Need It | Lorne Rubis: https://www.highlights.lornerubis.com/2015/08/the-netflix-keeper-test-and-the-courage-to-take-it • Innovation for Filmmaking, By Filmmakers: Why InterPositive Is Joining Netflix: https://about.netflix.com/en/news/why-interpositive-is-joining-netflix • InterPositive: https://weareinterpositive.com • Netflix Prize: https://en.wikipedia.org/wiki/Netflix_Prize • Quarterback on Netflix: https://www.netflix.com/title/81482895 • The Bill Simmons Podcast on Netflix: https://www.netflix.com/title/82186214 • Spencer Pratt on Instagram: https://www.instagram.com/spencerpratt • Salman Rushdie’s Substack: https://salmanrushdie.substack.com • Remarkably Bright Creatures on Netflix: https://www.netflix.com/title/81911351 • Eight Sleep: https://www.eightsleep.com • Tour de France: https://www.letour.fr/en — Recommended books: • Thinking in Systems: https://www.amazon.com/Thinking-Systems-Donella-H-Meadows/dp/1603580557 • Into Thin Air: A Personal Account of the Mt. Everest Disaster: https://www.amazon.com/Into-Thin-Air-Personal-Disaster/dp/0385494785 • Liar’s Poker: https://www.amazon.com/Liars-Poker-Norton-Paperback-Michael/dp/039333869X — 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
July 12 · 1 hr 36 min
How tech workers actually feel about AI in 2026 | Annual AI sentiment survey (Noam Segal)
Noam Segal is a longtime research leader across Airbnb, Meta, Twitter, Zapier, Intercom, and Figma, a certified coach, AI builder, and my community research lead. Together, we run the annual Tech Worker Sentiment Survey, now in its second year and one of the largest of its kind: a quantitative study of how people in tech actually feel about their jobs, AI, burnout, and the future of their careers. This year’s survey captured responses from thousands of workers across product, engineering, design, research, marketing, data, and sales, and the results are striking. In our in-depth conversation, we discuss: 1. Why AI has split the tech workforce almost exactly in half—one half that’s thriving, another that’s shaken 2. The four emotional archetypes defining tech workers right now (the Energized, the Conflicted, the Disoriented, and the Resentful) 3. Why burnout has jumped an alarming 11 points in a single year 4. Why nobody in tech would recommend their job to someone entering the industry today 5. The #1 fear in tech right now (it’s not job loss to AI) 6. Why managers are the single biggest lever for employee well-being 7. Concrete advice for what employees and leaders can do right now — Brought to you by: WorkOS—Make your app enterprise-ready, with SSO, SCIM, RBAC, and more: https://workos.com/lenny Mercury—Radically different banking, now with Command: https://mercury.com/command?utm_source=lennys&utm_medium=sponsored_newsletter&utm_campaign=26q3_brand_campaign — Episode transcript: https://www.lennysnewsletter.com/p/how-tech-workers-actually-feel-about — Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0 — Where to find Noam Segal: • X: https://x.com/noamseg • LinkedIn: https://www.linkedin.com/in/noamsegal — 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 Noam Segal (02:34) About the survey: methodology and scope (06:04) The core finding: AI has split the tech workforce in half (13:03) The AI identity stance (14:40) The four archetypes: Energized, Conflicted, Disoriented, Resentful (19:35) Burnout is surging (and why shipping faster is making it worse) (22:53) A glimmer of hope (24:55) Layoff worries (29:15) The career recommendation NPS score (36:45) The ladder metaphor: rungs disappearing beneath our feet (45:14) AI is making us faster, not better (52:53) The #1 fear: being squeezed to do more for the same pay (55:55) The emotional landscape and “smiling exhaustion” (01:01:02) Designers and researchers: the most negative group two years running (01:06:27) Who’s happiest (01:12:18) Managers: the single biggest lever on well-being (01:18:47) The industry is “chaotic” (01:24:53) What employees and leaders can do right now (01:31:32) AI guilt and closing thoughts — Referenced: • How tech workers are feeling in 2026: a workforce splitting in two: https://www.lennysnewsletter.com/p/how-tech-workers-are-feeling-in-2026 • How tech’s most resilient workers handle burnout: https://www.lennysnewsletter.com/p/how-techs-most-resilient-workers • Please stop the AI Confidence Theater: https://www.elenaverna.com/p/please-stop-the-ai-confidence-theater • 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 • NPS Is The Worst: https://www.npsistheworst.com • The Terminator: https://www.imdb.com/title/tt0088247 • Skynet: https://terminator.fandom.com/wiki/Skynet • 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 • Devin: https://devin.ai • An AI state of the union: We’ve passed the inflection point, dark factories are coming, and automation timelines | Simon Willison: https://www.lennysnewsletter.com/p/an-ai-state-of-the-union • Redeploying Fable 5: https://www.anthropic.com/news/redeploying-fable-5 • Why half of product managers are in trouble | Nikhyl Singhal (Meta, Google): https://www.lennysnewsletter.com/p/why-half-of-product-managers-are-in-trouble • Inside Linear: Building with taste, craft, and focus | Karri Saarinen (co-founder, designer, CEO): https://www.lennysnewsletter.com/p/inside-linear-building-with-taste • Building beautiful products with Stripe’s Head of Design | Katie Dill (Stripe, Airbnb, Lyft): https://www.lennysnewsletter.com/p/building-beautiful-products-with • The design process is dead. Here’s what’s replacing it. | Jenny Wen (head of design at Claude): https://www.lennysnewsletter.com/p/the-design-process-is-dead • OpenAI Codex lead on the new shape of product work | Andrew Ambrosino: https://www.lennysnewsletter.com/p/openai-codex-lead-on-the-new-shape • Elon Musk: ‘Chances are we’re all living in a simulation’: https://www.theguardian.com/technology/2016/jun/02/elon-musk-tesla-space-x-paypal-hyperloop-simulation — 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
July 9 · 1 hr 8 min
Adam Mosseri: AI is a tailwind for authenticity
Adam Mosseri is the Head of Instagram, where he oversees an app used by over 3 billion people. He also leads the team building Threads. Adam has run Instagram for longer than its founders did, after taking over from Kevin Systrom and Mike Krieger in 2018. A designer by training, he spent over 15 years at Meta, starting as a designer on Facebook’s mobile app, rising to lead Facebook’s News Feed, and eventually chosen to lead Instagram. During his tenure, Instagram’s user base has more than tripled. In our in-depth conversation, we discuss: 1. How the canonical product team structure is changing in 2026, from baker’s-dozen specialist teams to lean pods of four to six generalists 2. The rise of the “product staff” role—a blending of PM, design, data science, and research into one generalist operator 3. Why Adam is bullish on designers even as functional boundaries dissolve, and which roles are most at risk 4. What the Instagram algorithm knows about you, and why it’s only now catching up to what people assumed it knew years ago 5. Why the rise of AI-generated content is a tailwind for Instagram, and how the company is thinking about creator identity in a synthetic-content world 6. The two biggest product failures of Adam’s career—Facebook Home and the first version of Reels — Brought to you by: WorkOS—Make your app enterprise-ready, with SSO, SCIM, RBAC, and more: https://workos.com/lenny Mercury—Radically different banking, now with Command: https://mercury.com/command?utm_source=lennys&utm_medium=sponsored_newsletter&utm_campaign=26q3_brand_campaign — Episode transcript: https://www.lennysnewsletter.com/p/adam-mosseri-ai-is-a-tailwind-for — Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0 — Where to find Adam Mosseri: • X: https://x.com/mosseri • LinkedIn: linkedin.com/in/mosseri • Instagram: https://www.instagram.com/mosseri • Threads: https://www.threads.com/@mosseri — 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 Adam Mosseri (02:09) How product teams are changing inside Meta (05:48) Blurring roles and career anxiety (14:01) Hiring traits that matter now (16:48) How AI is resetting who succeeds at work (19:38) How Meta thinks about token spend and AI costs (23:23) Where human judgment still matters (25:56) Why AI is not automatically great at strategy (30:36) Why great product leaders are curators (34:23) What Instagram’s algorithm actually knows about you (38:08) Why chronological feeds often disappoint users (40:56) Why AI content may be a tailwind for Instagram (43:42) The future of AI and human content in the feed (48:00) What Adam admires about other social platforms (52:05) How he handles public criticism (56:31) Lessons from the Instagram feed redesign backlash (01:00:21) Adam’s biggest failure: Instagram on iPad (01:03:03) His approach to kids, screens, and social media (01:06:56) What Adam wants listeners to remember — Referenced: • What happens after coding is solved? | Fiona Fung (Manager of the Claude Code and Cowork Teams): https://www.lennysnewsletter.com/p/building-the-most-ai-pilled-engineering • Claude Code: https://www.anthropic.com/product/claude-code • Claude Cowork: https://www.anthropic.com/product/claude-cowork • Head of Claude Code: What happens after coding is solved | Boris Cherny: https://www.lennysnewsletter.com/p/head-of-claude-code-what-happens • A rational conversation on where AI is actually going | Benedict Evans: https://www.lennysnewsletter.com/p/a-rational-conversation-on-where • 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 • Mythos: https://www.anthropic.com/claude/mythos • Fable: https://www.anthropic.com/claude/fable • Pluralistic: The Reverse-Centaur’s Guide to Criticizing AI: https://pluralistic.net/2025/12/05/pop-that-bubble • Plastic Dream Sequence on Instagram: https://www.instagram.com/plasticdreamsequence • TikTok: https://www.tiktok.com • Facebook–Cambridge Analytica data scandal: https://en.wikipedia.org/wiki/Facebook%E2%80%93Cambridge_Analytica_data_scandal • Facebook Home: https://en.wikipedia.org/wiki/Facebook_Home — 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
June 28 · 1 hr 9 min
OpenAI Codex lead on the new shape of product work | Andrew Ambrosino
Andrew Ambrosino leads development of the Codex desktop app at OpenAI. Nearly 100% of OpenAI employees—not just engineers—now use Codex weekly. A lifelong builder with a background spanning engineering, design, product management, and founding companies, he is now responsible for turning the Codex desktop experience into what he calls “the best desktop app that has ever existed, full stop.” In our in-depth conversation, we discuss: 1. Why AI has completely flipped the product development process 2. What “taste” really means as a professional skill, and why it is emerging as the most valuable capability in an AI-first workplace 3. Why Andrew believes the Codex app would have failed if they launched it last November (vs. in February) 4. The “zone defense” model for how product managers at OpenAI operate when everyone can build anything 5. How roles are collapsed on Andrew’s team, and why eliminating the concept of roles entirely is a big mistake 6. How Andrew uses Codex to run his own workflows 7. The vision for a home base that coordinates work across ChatGPT, Codex, and the tools people already use. — Brought to you by: WorkOS—Make your app enterprise-ready, with SSO, SCIM, RBAC, and more Mercury—Radically different banking, now with Command — Episode transcript: https://www.lennysnewsletter.com/p/openais-codex-lead-on-the-new-shape — Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0 — Where to find Andrew Ambrosino: • X: https://x.com/ajambrosino • LinkedIn: https://www.linkedin.com/in/ajambrosino • Website: https://ambrosino.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 Andrew Ambrosino (02:30) How AI is changing the shape of product work (06:32) When to use documents vs. prototypes (10:25) What “taste” actually means (12:06) Why AI is still bad at design (16:18) Is the design process really dead? (21:35) What the design process looks like on the Codex team (23:41) Are product functions disappearing? (27:22) Team structure (30:12) IC vs. management (31:37) Planning roadmaps (35:16) Building features that don’t work yet (38:13) The ambition problem: when you’re too AGI-pilled (39:17) The latest frontier: loops and autonomous development (52:05) How Andrew uses Codex to automate his entire job (46:52) The power of computer use and browser automation (49:10) Will we run all our SaaS apps inside Codex? (52:05) The future vision for Codex (57:20) The videographer who built a Premiere Pro extension with Codex (59:30) Failure corner (1:01:50) Lightning round (1:07:03) BTS: How our producer uses Codex for editing — References: https://www.lennysnewsletter.com/p/openais-codex-lead-on-the-new-shape — 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
June 21 · 1 hr 38 min
What happens after coding is solved? | Fiona Fung (Manager of the Claude Code and Cowork Teams)
Fiona Fung leads the teams behind Claude Code and Cowork at Anthropic (overseeing Boris Cherny and the entire engineering and PM team). Before Anthropic, she spent 11 years at Microsoft building Visual Studio and TypeScript and then moved to Meta, where she started Facebook Marketplace (now generating over $100 billion in GMV annually), worked on Meta’s first smart glasses and AR glasses, and led infrastructure, growth, integrity, and safety teams at Instagram. She’s been an engineer for over 25 years and has a unique perspective on how the role of building software is changing. In our in-depth conversation, we discuss: 1. What she’s learned about running a team that’s shipping 8x more code than before 2. Which roles AI will transform next 3. Specific ways her team uses AI 4. How Claude “routines” have changed how she operates as a manager 5. The context-switching problem no one has solved yet 6. The biggest unsolved problem in AI 7. What keeps her up at night — Brought to you by: WorkOS—Make your app enterprise-ready, with SSO, SCIM, RBAC, and more: https://workos.com/lenny Mercury—Radically different banking, now with Command: https://mercury.com/ — Where to find Fiona Fung: • LinkedIn: linkedin.com/in/fionafung — 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 Fiona Fung (02:31) How the engineering role has transformed over 25 years (09:28) What an AI-pilled software team looks like in 2026 (12:26) Using Claude to manage and review team output (14:40) The evolution of code review and verification (16:55) Who to hire: creative builders and deep systems experts (18:18) The shift to ambitious thinking (19:40) The growth mindset required to thrive in AI-native teams (25:52) Helping small businesses adopt AI tools (31:46) How Anthropic spots latent demand and builds for it (35:08) The next frontier: asynchronous work with AI routines (38:06) Agency and accountability in AI-native teams (39:40) The vibe shift from token-maxing to ROI measurement (44:24) The “bad vs. sad” quality framework (49:34) Why all managers start as ICs at Anthropic (55:24) Preventing skill atrophy (58:43) Managing context switching with 20 AI agents running (1:00:08) How PM and data science roles are transforming (1:03:40) The importance of dogfooding and using your own product (1:08:36) Outstanding questions (1:12:48) The future of engineering jobs and education (1:17:59) What keeps Fiona up at night: team culture at scale (1:22:53) From six-month roadmaps to JIT (just-in-time) monthly planning (1:27:03) Lightning round — References: https://www.lennysnewsletter.com/p/building-the-most-ai-pilled-engineering — 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
June 14 · 1 hr 39 min
The hidden pattern behind successful products | Mark Pincus (founder of Zynga)
Mark Pincus founded Zynga—the company behind Words With Friends, FarmVille, and Zynga Poker—and has arguably created more hit consumer products than anyone in history. At Zynga, eight of 10 major game launches became massive hits, reaching over a billion players. Over the past five years, Mark has been synthesizing everything he’s learned about building successful consumer products and turning it into a book, Life at the Speed of Play, which comes out on June 23. This is the first interview he’s done about the book. In our in-depth conversation, we discuss: 1. His “Proven, Better, New” framework: copy what’s proven, make it better so that 10 out of 10 people say “f*ck yes, I’ll use this”—then add something new 2. Why being less ambitious is the path to the most ambitious ideas 3. His rule of thumb that your instincts are right 95% of the time, but your ideas are wrong 75% of the time 4. “Kill hope before hope kills you” 5. How to raise kids in the age of AI — Brought to you by: WorkOS—Make your app enterprise-ready, with SSO, SCIM, RBAC, and more Vanta—Automate compliance, manage risk, and accelerate trust with AI — Episode transcript: https://www.lennysnewsletter.com/p/the-common-pattern-behind-successful — Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0 — Where to find Mark Pincus: • X: https://x.com/markpinc • LinkedIn: https://www.linkedin.com/in/markpincus • Website: https://www.lifeatthespeedofplay.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 Mark Pincus (02:46) The Proven Better New framework overview (07:29) Earning the right to innovate (08:30) What “better” really means (12:03) Quick summary of the framework (12:40) Examples of the framework in action (13:30) How to use proven correctly on your platform (15:13) The moral arbitrage of copying (23:55) Be less ambitious (28:25) The Bolt.new story and staying humble (33:15) Kill hope before hope kills you (37:00) Using AI as a failure machine (40:08) Why Zynga’s games succeeded (it wasn’t virality) (48:36) The future of consumer social apps (57:05) How to know if your product is a B+ (1:01:25) Distribution in the age of AI (1:15:39) Make everyone a CEO (1:18:18) Stay close to the metal (1:21:35) Why Mark says micromanagement is beautiful (1:23:35) The expert witness (1:25:05) The number one job of a CEO is to be right (1:26:35) What Mark is teaching his five kids (1:35:14) Mark’s “why” (1:37:08) Mark’s new book: Life at The Speed of Play — Referenced: • Tribe.net: https://en.wikipedia.org/wiki/Tribe.net • Zynga: https://www.zynga.com • Sid Meier: https://en.wikipedia.org/wiki/Sid_Meier • Electronic Arts: https://www.ea.com • CityVille: https://en.wikipedia.org/wiki/CityVille • Words With Friends: https://wordswithfriends.com/ • Scrabble: https://playscrabble.com • Reddit: https://www.reddit.com • TED Radio Hour, MIT Media Lab founder, 1984 TED talk.: https://www.ted.com/talks/nicholas_negroponte_5_predictions_from_1984 • Peter Thiel on LinkedIn: https://www.linkedin.com/in/peterthiel • FarmVille: https://en.wikipedia.org/wiki/FarmVille • Craig Newmark: https://en.wikipedia.org/wiki/Craig_Newmark • How to consistently go viral: Nikita Bier’s playbook for winning at consumer apps (co-founder of TBH, Gas, advisor, investor): https://www.lennysnewsletter.com/p/how-to-consistently-go-viral-nikita-bier • Angry Birds: https://www.angrybirds.com/ • OMGPop: https://en.wikipedia.org/wiki/OMGPop • Draw Something: https://en.wikipedia.org/wiki/Draw_Something • Slack founder: Mental models for building products people love ft. Stewart Butterfield: https://www.lennysnewsletter.com/p/slack-founder-stewart-butterfield • Brian Chesky’s new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach • Garry Tan on LinkedIn: https://www.linkedin.com/in/garrytan • Brian Armstrong on LinkedIn: https://www.linkedin.com/in/barmstrong • Jason Citron on X: https://x.com/jasoncitron • Stanislav Vishnevskiy on LinkedIn: https://www.linkedin.com/in/svishnevskiy • Jeff Bezos on X: https://x.com/JeffBezos • Andy Jassy on X: https://x.com/ajassy • Niantic: https://nianticlabs.com • Pokémon Go: https://pokemongo.com • Bing Gordon on LinkedIn: https://www.linkedin.com/in/binggordon — Recommended book: • Life at the Speed of Play: Launch Products People Love!: https://www.amazon.com/Life-Speed-Play-Launch-Products/dp/0063352575/ref=tmm_hrd_swatch_0 — 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
June 7 · 1 hr 35 min
Father of the iPod and iPhone on building taste, judgment, and creativity in the AI era | Tony Fadell
Tony Fadell created the iPod, co-created the iPhone, and founded Nest (which he sold to Google for $3.2 billion). He’s co-authored over 300 patents, was part of the legendary team at General Magic, and wrote one of the most important and inspiring books for builders, called Build. In our in-depth conversation, we discuss: 1. The heated internal debates about whether the iPhone should have a physical keyboard 2. Why opinion-based decisions are essential for v1 products 3. Why marketing matters as much as the product itself, and how the iPod almost failed 4. Why voice will eventually become the primary interface with AI 5. Why cognitive surrender to AI is the biggest risk facing product builders today — Brought to you by: WorkOS—Make your app enterprise-ready, with SSO, SCIM, RBAC, and more: https://workos.com/lenny Vanta—Automate compliance, manage risk, and accelerate trust with AI: https://vanta.com/lenny — Episode transcript: https://www.lennysnewsletter.com/p/father-of-the-ipod-and-iphone-on — Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0 — Where to find Tony Fadell: • X: https://x.com/tfadell • LinkedIn: https://www.linkedin.com/in/tonyfadell • Website: https://www.buildc.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 Tony Fadell (02:23) The Blackberry vs. iPhone keyboard debate (07:50) Micromanaging vs. kind lies: what great products actually need (15:57) The Nest thermostat and smoke alarm story (21:22) How to decide what’s worth building: pain plus new technology (27:36) The three-generation rule: why nothing works the first time (34:20) The full customer journey: why marketing defines your product (40:53) The power of storytelling and the press-release-first approach (48:37) The evolution of product management and the builder role (50:27) Why AI-generated code creates brittle, unmaintainable products (58:00) Storytelling techniques (1:05:45) The next iPhone (1:13:15) Hardware is back (1:17:01) What Tony is most excited about (1:21:38) Working with Tony (1:25:36) Ethics, morals, and the responsibility of product builders (1:32:40) How to connect with Tony and Build Collective — References: https://www.lennysnewsletter.com/p/father-of-the-ipod-and-iphone-on — 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
May 31 · 1 hr 19 min
A rational conversation on where AI is actually going | Benedict Evans
Benedict Evans is an independent analyst and former partner at Andreessen Horowitz, where he spent years as their in-house “thinker” tracking the most important technology trends. For the past six years, he’s been publishing deeply researched presentations on where tech is heading, most recently focused on AI’s transformation of the economy. His work is read by founders, investors, and operators trying to make sense of a noisy field. His most controversial opinion: AI is as big a deal as the internet or mobile—and only as big. In our in-depth conversation, we discuss: 1. Why we’re in “1997” for AI—early, exciting, and deeply uncertain about what comes next 2. Where value will actually accrue in the AI stack 3. The anti-AI backlash, and where it may lead 4. The surprising boom in consulting and professional services at AI companies 5. Why distribution is becoming the ultimate moat as software gets easier to build 6. Why the right question about your job isn’t “What percent can AI do?” but “Is this a task or a job?” 7. Why things will probably be okay—and what you need to do to prepare — Brought to you by: WorkOS—Make your app enterprise-ready, with SSO, SCIM, RBAC, and more: https://workos.com/lenny Vanta—Automate compliance, manage risk, and accelerate trust with AI: https://vanta.com/lenny — Episode transcript: https://www.lennysnewsletter.com/p/a-rational-conversation-on-where — Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0 — Where to find Benedict Evans: • LinkedIn: https://www.linkedin.com/in/benedictevans • Newsletter: https://www.ben-evans.com/newsletter • Website: https://www.ben-evans.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 Benedict Evans (02:19) What people aren’t pricing in about AI’s impact (06:24) Why we’re in the 1997 moment of AI (09:44) The unexpected boom in professional services and consultants (17:44) Why distribution is becoming the ultimate moat (23:17) The coming job transformation: what’s real vs. panic (27:33) Why AGI definitions keep shifting (38:11) Where value will accrue: models vs. applications (42:55) Distribution wars: Google, Meta, Apple, and OpenAI (48:12) The anti-AI sentiment and backlash (53:11) How to raise kids in an AI future (58:27) What jobs to steer toward or away from (59:20) The question nobody’s asking about AI (1:06:25) How to be successful in this coming future (1:08:43) AI corner (1:11:43) Lightning round — Referenced: https://www.lennysnewsletter.com/p/a-rational-conversation-on-where — 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
May 24 · 1 hr 34 min
The AI paradox: More automation, more humans, more work | Dan Shipper
Dan Shipper is the co-founder and CEO of Every, a media and software company that’s become a living laboratory for the future of work. Everyone at his company of about 30 people is an AI early adopter; from editors to ops people, they use AI to do much of their work, giving Every a unique lens into where the world is heading. A year ago on this show, Dan predicted that people were sleeping on Claude Code for nontechnical work, which proved to be remarkably prescient. Today he’s back with another set of calls: the SaaS apocalypse is dumb, CLIs are over, the forward deployed engineer is the most valuable new hire, and the only thing you need to do to stay employed is ride the models. Dan’s predictions: 1. The future of work will happen inside Codex or Claude Code. 2. Every company will have one “super-agent” inside their Slack that every employee talks to regularly. 3. SaaS is not dead—in fact, Dan is bullish on SaaS stocks. His contrarian take: “I would buy SaaS stocks right now.” 4. SaaS economics will shift: users will bring their own AI tokens into apps, which actually improves SaaS margins. 5. PMs will thrive in the AI era. 6. Full-stack designers will become superheroes. 7. The AI job apocalypse is not happening. 8. Forward deployed engineer is the new most essential role. 9. CLIs are over. 10. Automation is a lie. 11. We will read way more AI-generated writing and we will like it. 12. We’ll be building software for humans and agents to use together. — Brought to you by: WorkOS—Make your app enterprise-ready, with SSO, SCIM, RBAC, and more: https://workos.com/lenny Vanta—Automate compliance, manage risk, and accelerate trust with AI: https://vanta.com/lenny — Episode transcript: https://www.lennysnewsletter.com/p/the-ai-paradox-dan-shipper — Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0 — Where to find Dan Shipper: • X: https://x.com/danshipper • LinkedIn: https://www.linkedin.com/in/danshipper/ • Podcast: https://every.to/podcast • Website: https://danshipper.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 Dan Shipper (02:56) Dan’s unique position living in the AI future (09:17) How the way we work will change in the coming year (16:39) The case for general agents (18:08) Codex and Claude Code as the new operating system for work (25:39) How Cursor fits in (27:42) How this changes what SaaS companies should build (31:13) Why CLI is already over (33:34) Two agents are better than one (36:22) Why Dan is bullish on SaaS stocks (39:01) Why automation doesn’t reduce human work (47:00) The value of human-written code (48:36) Quick recap (50:15) How work is changing (56:17) Why data scientists are drowning in bad analysis (58:24) Which product/tech roles are least changed by AI (1:02:17) We will read way more AI-generated writing and we will like it (1:08:28) Why product managers will dominate the AI era (1:11:05) Full-stack designers are the other big winners (1:13:11) The AI job apocalypse won’t happen (1:16:00) How to “ride the models” to stay relevant (1:21:02) Final predictions and advice (1:25:24) Lightning round — References: https://www.lennysnewsletter.com/p/the-ai-paradox-dan-shipper — 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
May 17 · 1 hr 39 min
Why we’re at the beginning of the AI hardware boom | Caitlin Kalinowski (ex–OpenAI, Meta, Apple)
Caitlin Kalinowski was most recently at OpenAI helping build their robotics and hardware teams from scratch. Prior to that, she was head of AR glasses and VR hardware at Meta, where she led the teams building every generation of the Quest, Rift, and Orion, and was Meta’s first consumer electronics hire. Before this, she was technical lead on MacBook Air and Mac Pro at Apple, and helped engineer the original unibody MacBook Pro. She’s designed and engineered some of the hardest and most beloved consumer hardware products in history and is now focused on the next frontier: robotics. In our in-depth conversation, we discuss: 1. VR—what happened? 2. The coming memory price shock and why she’s telling startups to pre-buy now 3. How the technologies built for VR became the foundation of modern warfare 4. Why humanoid robots are still just prototypes, and what’s actually gating mass deployment 5. Lessons from Steve Jobs, Mark Zuckerberg, and Sam Altman 6. Why she left OpenAI — Brought to you by: WorkOS—Make your app enterprise-ready, with SSO, SCIM, RBAC, and more: https://workos.com/lenny Vanta—Automate compliance, manage risk, and accelerate trust with AI: https://vanta.com/lenny — Episode transcript: https://www.lennysnewsletter.com/p/why-were-at-the-beginning-of-the — Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0 — Where to find Caitlin Kalinowski: • X: https://x.com/kalinowski007 • LinkedIn: https://www.linkedin.com/in/ckalinowski • Website: https://www.caitlinkalinowski.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 Caitlin Kalinowski (02:32) Why VR didn’t take off despite incredible hardware (04:55) The future of AR glasses and physical AI (08:45) Why robotics and hardware are suddenly hot (13:33) Why humanoid robots aren’t ready yet (16:13) Supply chain bottlenecks threatening robotics (17:31) Why magnets and actuators are critical dependencies (20:51) The geopolitical implications of hardware supply chains (24:48) AI safety concerns with physical robots (26:50) Apple’s approach to hardware excellence (30:10) Building a hardware program from scratch at Meta (31:39) The Quest 2 cost reduction story (33:07) Critical principles for hardware development (39:58) The MacBook Air manila envelope moment (41:01) The butterfly keyboard situation (41:43) Lessons from Apple on customer feedback (44:46) The memory price crisis coming for hardware (49:31) How many components go into a robot (52:53) When to use off-the-shelf vs. custom components (55:02) How AI is changing hardware engineering (1:00:27) Why humanoids aren’t the answer for most use cases (1:03:05) When robots will build other robots (1:06:23) What makes a robot feel human and connected (1:09:15) Robots in the home (1:12:00) What the next five years look like (1:15:38) Why she left OpenAI (1:18:09) How to hire exceptional hardware teams (1:23:42) Lessons from Steve Jobs, Mark Zuckerberg, and Sam Altman (1:27:27) Failure corner (1:32:33) Lightning round — References: https://www.lennysnewsletter.com/p/why-were-at-the-beginning-of-the — 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
May 10 · 1 hr 39 min
How to build a company that withstands any era | Eric Ries, Lean Startup author
Eric Ries is the author of The Lean Startup, a book that reshaped how a generation of founders think about building companies. His new book, Incorruptible, explains how successful companies are destroyed by failing to protect what makes them valuable, and how to change it. In our in-depth conversation, we discuss: 1. Why 80% of venture-backed founders are ousted within three years of going public 2. The governance structures that protect companies like Anthropic, Costco, and Novo Nordisk 3. The simple legal filing that takes two pages and could save your company 4. Financial gravity: why successful companies predictably get corrupted into mediocrity 5. Why mission-aligned companies like Anthropic reap major benefits from protecting their mission through governance 6. Why success won’t protect you—it instead makes you a bigger target — Brought to you by: WorkOS—Make your app enterprise-ready, with SSO, SCIM, RBAC, and more: https://workos.com/lenny Vanta—Automate compliance, manage risk, and accelerate trust with AI: https://vanta.com/lenny — Episode transcript: https://www.lennysnewsletter.com/p/how-to-build-a-company-that-withstands — Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0 — Where to find Eric Ries: • X: https://x.com/ericries • LinkedIn: https://www.linkedin.com/in/eries • Website: https://www.incorruptible.co • Newsletter: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://news.theleanstartup.com/ • Podcast:⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ https://ericriesshow.com • YouTube: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.youtube.com/@theericriesshow⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ — 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 Eric Ries (02:26) Introducing Incorruptible (06:26) Protecting what you’ve built (11:35) Why founders get ousted (14:58) Too early, too late (19:32) The blueprint: ethos plus integrity (20:49) Novo Nordisk’s 100-year governance fortress (26:41) The Vectura Group and Philip Morris (33:16) The “harder is easier” principle (37:22) Cloudflare’s mission emergence story (42:43) Groupon’s email frequency death spiral (45:37) How to define your purpose (51:09) Mission-driven vs. mission-hopeful companies (54:46) Integrity: structural and personal (57:47) Shareholder primacy: the 40-year-old “natural law” (01:00:04) Public benefit corporations: the easiest protection (01:04:24) Downsides and objections (01:06:08) The Anthropic example: fastest-growing company ever (01:08:39) The torchbearers in every organization (01:10:37) The culture bank: deposits and withdrawals (01:12:28) OpenAI and Anthropic governance (01:16:21) Mission guardians explained (01:18:29) Spiritual holding companies (01:21:53) The founder control trap (01:25:25) Three things to do this week (01:30:10) AI alignment and human alignment (01:34:00) Conway’s law: org charts in architecture (01:37:31) Book resources and farewell — References: https://www.lennysnewsletter.com/p/how-to-build-a-company-that-withstands — 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
May 3 · 1 hr 27 min
Why cultivating agency matters more than cultivating skills in the AI era | Max Schoening (Head of Product, Notion)
Max Schoening is head of product at Notion, where he’s been especially effective at getting designers and PMs to ship code, prototype in the terminal, and launch extremely successful AI products. He was previously a PM at Google, ran design at Heroku, was VP of Design (and a part-time engineer) at GitHub, and is a two-time founder. He’s one of the most AI-forward product leaders out there and one of the deepest thinkers on how AI changes how we build and use software. We discuss: 1. What’s most worked in getting designers and PMs to embrace AI 2. Why agency—not skills—is the thing that separates people who thrive from those who fall behind 3. How the first 10% of every project is now “free,” and what that means for product development 4. Max’s “tiny core” theory of great products: iPhone multitouch, the GitHub pull request, Notion blocks, Dropbox’s menu bar icon 5. Why the SaaSpocalypse is overstated 6. Why the amount of software has exploded but the quality hasn’t, and why that gap creates opportunity — Brought to you by: WorkOS—Make your app Enterprise Ready, with SSO, SCIM, RBAC, and more: https://workos.com/lenny Vanta—Automate compliance, manage risk, and accelerate trust with AI: https://vanta.com/lenny — Episode transcript: https://www.lennysnewsletter.com/p/why-cultivating-agency-matters-more — Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0 — Where to find Max Schoening: • X: https://x.com/mschoening • LinkedIn: https://www.linkedin.com/in/max-schoening • Website: https://max.dev — 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 Max Schoening (01:55) The origin story of designers coding at Notion (06:30) How much designers and PMs are shipping today (08:24) The balance between shipping code and strategic work (10:32) Why agency will help you thrive in the AI era (11:49) Examples of high agency at Notion (13:52) What we might lose as roles merge (15:56) Advice for developing agency (17:42) Malleable software explained (20:43) The Dieter Rams video and design philosophy (24:00) The SaaS apocalypse debate (28:25) How product building has changed in the past two years (30:27) What’s next in how we build products (34:16) Token spend and ROI conversations (37:39) Getting people to change how they work (39:04) Max’s AI stack (41:41) Which roles AI will transform next (44:26) When companies will start caring about ROI (48:38) Why Notion AI is so successful (51:47) How to ship more quickly while maintaining quality (56:40) Building taste through iterations (1:00:09) What matters most in building successful products (1:05:06) Using the jobs-to-be-done framework (1:07:28) Hot take on universal basic income (1:09:26) What Max would do with AGI (1:10:53) Contrarian corner (1:13:14) Failure corner (1:16:20) Advice for young people in Silicon Valley (1:19:20) Lightning round and final thoughts — Referenced: https://www.lennysnewsletter.com/p/why-cultivating-agency-matters-more — 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
April 26 · 1 hr 10 min
Snapchat CEO: Why distribution has become the most important moat | Evan Spiegel
Evan Spiegel, the co-founder and CEO of Snap, is one of the very few people in the world who has successfully built and scaled a lasting consumer social product. Snapchat has nearly 1 billion MAUs, and Evan and his team invented some of the most important consumer products and features, including Stories, AR glasses, swipe-based navigation, the camera as the primary UX, and a lot more. In our in-depth conversation, we discuss: 1. Why distribution is now the biggest challenge for creating a consumer technology business 2. How Snap innovates at scale with a 9-to-12-person design team: no titles, no hierarchy, hundreds of ideas reviewed weekly with the CEO 3. Why a pure software business is no longer a moat, and what actually creates durable competitive advantages today 4. How AI is changing the way designers work and why they’re now shipping code 5. Why every major Snap feature was copied and how that forced the company to work differently 6. Evan’s prediction that humanity’s comfort with AI will be a bigger bottleneck than the technology itself 7. This year’s crucible moment for Snap — Brought to you by: WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs: https://workos.com/lenny Vanta—Automate compliance, manage risk, and accelerate trust with AI: https://vanta.com/lenny — Episode transcript: https://www.lennysnewsletter.com/p/snapchat-ceo-why-distribution-is — Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0 — Where to find Evan Spiegel: • X: https://x.com/evanspiegel • Snapchat: https://www.snapchat.com/@evan • LinkedIn: https://www.linkedin.com/in/evan-spiegel • Website: https://www.spiegelfamilyfund.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 Evan Spiegel (02:28) Why consumer social products are so hard to build (04:31) How Snapchat cracked distribution with close friends, not network size (05:50) Why distribution is the new moat in the AI era (08:39) Snapchat’s innovation track record (and why software isn’t a moat) (11:39) Why Snap is betting on two of the hardest businesses: consumer social and hardware (16:00) Specs use cases (17:56) The innovation process (21:34) The velocity of design work at Snapchat (25:07) Why Evan says you must talk to customers (26:06) The origin story of Stories (28:25) How screenshot detection saved early Snapchat (31:03) Why they waited to hire PMs—and what role they play now (34:41) How AI is shifting the designer-PM-engineer triad (36:10) Design as an intentional bottleneck for product cohesion (37:24) Why staying close to customers matters for any leader (39:39) What Evan looks for when hiring designers (41:57) How to develop young design talent (44:16) Designers shipping code with AI—and the guardrails needed at scale (47:20) Using jobs-to-be-done to organize AI transformation (48:50) How the CEO job has changed over 15 years (51:30) Learning to communicate (54:08) Why this year is Snapchat’s “crucible moment” (56:22) Being the “middle child” in tech (57:51) Screen-time philosophy with four kids (ages 2 to 15) (1:01:08) AI Corner (1:04:02) Contrarian Corner (1:06:04) Lightning round and final thoughts — References: https://www.lennysnewsletter.com/p/snapchat-ceo-why-distribution-is — 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
April 23 · 1 hr 25 min
How Anthropic’s product team moves faster than anyone else | Cat Wu (Head of Product, Claude Code)
Cat Wu is Head of Product for Claude Code and Cowork at Anthropic, building one of the most important AI products of this generation. Before joining Anthropic, Cat spent years as an engineer and briefly worked in VC. Today, she’s interviewing hundreds of product managers who are trying to break into AI—and seeing firsthand what separates those who thrive from those who fall behind. We discuss: 1. How Anthropic’s shipping cadence went from months to weeks to days 2. The emerging skills PMs need to develop right now 3. Why you need to build products that don’t yet fully work, so you’re ready when the next model closes the gap 4. Cat’s most underrated AI skill: asking the model to introspect on its own mistakes 5. Why Claude’s personality is core to its success 6. Why Anthropic’s mission alignment eliminates the friction that slows most large organizations 7. Why “just do things” is the most important principle for working at AI-native companies — Brought to you by: WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs Vanta—Automate compliance, manage risk, and accelerate trust with AI — Episode transcript: https://www.lennysnewsletter.com/p/why-half-of-product-managers-are-in-trouble — Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0 — Where to find Cat Wu: • X: https://x.com/_catwu • LinkedIn: linkedin.com/in/cat-wu • Newsletter: https://catwu.substack.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 Cat Wu (01:29) Working with Boris Cherny (04:29) What Anthropic looks for when hiring PMs (06:18) How to help your teams move fast (08:58) How PRDs and roadmaps have evolved at Anthropic (10:28) The Mythos model and Anthropic’s shipping velocity (11:54) What happened with the Claude Code source code leak (12:53) Integrating with OpenClaw (14:19) How the PM team is structured at Anthropic (15:42) How engineer and PM roles are merging (17:54) Why product taste is the most valuable skill (20:10) Where human brains will continue to be useful (22:23) How to stay sane in constant chaos (24:16) What gets sacrificed when you ship so fast (27:47) The /powerup command (28:32) Why Anthropic has been so successful (32:28) When to use Claude Code vs. Desktop vs. Cowork (35:58) Tips for getting started with Cowork (38:44) Demo: Using Cowork to build slide decks overnight (41:48) Cat’s PM tech stack and internal tools (46:47) Which teams use the most tokens (51:15) The emerging skills PMs need for AI companies (55:00) Why building evals is underappreciated (58:44) Why Claude’s character and personality matter so much (1:00:44) How new models force product changes (1:05:11) The vision for Claude Code and Cowork (1:07:22) Advice for thriving in an AI-driven world (1:09:18) Why 95% automation isn’t good enough (1:11:58) Build apps you use every day, not prototypes (1:13:41) The divide between AI skeptics and believers (1:15:19) Lightning round — Referenced: https://www.lennysnewsletter.com/p/how-anthropics-product-team-moves — 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
April 19 · 1 hr 35 min
Why half of product managers are in trouble | Nikhyl Singhal (Meta, Google)
Nikhyl Singhal is the founder of The Skip, a community for senior product leaders; a former product exec at Meta, Google, and Credit Karma; and a many-time founder. He’s also one of the most honest, unfiltered voices on what’s actually happening in product management right now. In our in-depth conversation, we discuss: 1. Why the next two years will be the most chaotic period in product management history 2. Why half of current product managers are at risk, and what separates those who’ll do well 3. Why you need to find your “moments of joy” with AI 4. The “smiling exhaustion” he’s seeing across the product community 5. The psychological barriers that prevent people from reinventing themselves 6. Why your resume’s fancy logos matter less than ever, and what matters now 7. His prediction that companies will shed 30,000 people and rehire 8,000—all AI-first — Brought to you by: WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs Vanta—Automate compliance, manage risk, and accelerate trust with AI — Episode transcript: https://www.lennysnewsletter.com/p/why-half-of-product-managers-are-in-trouble — Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0 — Where to find Nikhyl Singhal: • LinkedIn: https://www.linkedin.com/in/nikhyl • X: https://x.com/nikhyl • Podcast & Newsletter: https://skip.show • Skip Community: https://skip.community • Skip Coach: https://skip.coach • Skip.help: https://skip.help — 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 Nikhyl Singhal (02:25) The big picture: what’s changing for product managers (10:00) Are product leaders doing better than 2-3 years ago? (11:44) What will change in the next couple of years (14:23) How companies are changing the way they build products (15:51) What “judgment” really means for PMs (17:46) Why there won’t be any more bad software (20:25) The skills you need to be effective today (23:31) Why there are more PM roles than ever (24:27) The builder versus information-mover divide (30:14) The non-builder problem (30:53) Should PMs code? (34:15) Why experienced leaders still matter (35:44) The diversity setback nobody’s talking about (37:21) Why your brand doesn’t matter as much anymore (39:54) How valued skills are flipping upside down (40:49) Why change is so hard for humans (43:53) The “equal disappointment” algorithm (46:39) You must cross the threshold (48:37) This chaos will settle (53:19) Finding your moment of joy (58:50) Nikhyl’s AI stack and what he’s building (1:00:53) The obsolescence mindset (1:05:24) Specific advice for PMs right now (1:08:58) The four jobs that will exist in the future (1:11:59) Why alignment is changing (but not disappearing) (1:15:40) How engineering is changing even more than PM (1:17:04) The surprising design plateau (1:18:49) Finding optimism in the chaos (1:21:12) Lightning round — Referenced: • Building a long and meaningful career | Nikhyl Singhal (Meta, Google): https://www.lennysnewsletter.com/p/building-a-long-and-meaningful-career • COBOL: https://en.wikipedia.org/wiki/COBOL • United Airlines: https://www.united.com • State of the product job market in early 2026: https://www.lennysnewsletter.com/p/state-of-the-product-job-market-in-ee9 • Head of Growth (Anthropic): “Claude is growing itself at this point” | Amol Avasare: https://www.lennysnewsletter.com/p/anthropics-1b-to-19b-growth-run • Demis Hassabis on X: https://x.com/demishassabis • Sam Altman on X: https://x.com/sama • Dario Amodei on X: https://x.com/DarioAmodei • Cross on Prime Video: https://www.amazon.com/Cross-Season-1/dp/B0D6X7ZZHC • Jack Ryan on Prime Video: https://www.amazon.com/Tom-Clancys-Jack-Ryan/dp/B0CNDCMN8R • 24 on Prime Video: https://www.amazon.com/24-Season-1/dp/B000HPF85A • Claude Code: https://code.claude.com • Codex: https://chatgpt.com/codex • Lovable: https://lovable.dev • Sonos: https://www.sonos.com • “There are only four jobs” on X: https://x.com/yrechtman/status/2039012253341495462 • Paradise on Hulu: https://www.hulu.com/series/paradise-2b4b8988-50c9-4097-bf93-bc34a99a5b4f • Lioness on Paramount+: https://www.paramountplus.com/shows/lioness • Tesla: https://www.tesla.com • Albert Einstein’s quote: https://www.goodreads.com/quotes/115696-genius-is-1-talent-and-99-percent-hard-work — Recommended books: • James: https://www.amazon.com/James-Novel-Percival-Everett/dp/0385550367 • The Adventures of Huckleberry Finn: https://www.amazon.com/Adventures-Huckleberry-Finn-Unabridged-Uncensored/dp/195483943X — 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
April 12 · 1 hr 22 min
Hard truths about building in the AI era | Keith Rabois (Khosla Ventures)
Keith Rabois was an early executive at PayPal (part of the famous PayPal Mafia), COO at Square, VP of Corporate Development at LinkedIn, and an early investor in Stripe, DoorDash, Airbnb, YouTube, Ramp, and Palantir. Currently he’s managing director at Khosla Ventures. Also, he hasn’t touched a computer since September 2010 (he does everything from an iPad). In our in-depth conversation, Keith shares: 1. The barrels vs. ammunition hiring framework (and how to spot barrels) 2. Why talking to customers is actively harmful for consumer products 3. How to identify undiscovered talent 4. Why the PM role is dying 5. The three traits of the best-performing companies right now 6. The specific interview question he asks every senior candidate 7. Why CMOs (not engineers) are becoming the #1 consumer of tokens — Brought to you by: WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs Vanta—automate compliance, manage risk, and accelerate trust with AI — Episode transcript: https://www.lennysnewsletter.com/p/hard-truths-about-building-in-the-ai-era — Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0 — Where to find Keith Rabois: • X: https://x.com/rabois • LinkedIn: linkedin.com/in/keith • Website: https://www.khoslaventures.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 Keith Rabois (01:59) Why Keith hasn’t used a computer since 2010 (04:52) The team you build is the company you build (07:40) How Keith learned to identify talent at PayPal (10:05) Tactics for getting better at hiring (15:31) The barrels vs. ammunition framework (18:52) What makes someone a barrel (22:36) How to attract the best talent (26:18) Building companies on undiscovered talent (27:53) Why better performance requires more pressure (32:36) Career advice in the age of AI (35:14) The future of the product triad (41:03) Why design and code are merging (49:35) What practicing law taught Keith about entrepreneurship (51:22) Contrarian takes on customer feedback (1:02:33) Identifying great AI opportunities (1:05:13) Advice for evaluating statrups (1:12:36) Criticizing in public vs. private (1:15:05) Failure corner (1:17:29) Lightning round — Referenced: • Square: https://squareup.com • Jack Dorsey on X: https://x.com/jack • Head of Claude Code: What happens after coding is solved | Boris Cherny: https://www.lennysnewsletter.com/p/head-of-claude-code-what-happens • Simon Willison’s Weblog: https://simonwillison.net • Vinod Khosla on X: https://x.com/vkhosla • Peter Thiel on X: https://x.com/peterthiel • Max Levchin on X: https://x.com/mlevchin • David Sacks on LinkedIn: https://www.linkedin.com/in/davidoliversacks • Tony Xu on X: https://x.com/t_xu • David Sze on X: https://x.com/davidsze • Faire: https://www.faire.com • Max Rhodes on X: https://x.com/MaxRhodesOK • Jeffrey Kolovson on LinkedIn: https://www.linkedin.com/in/jeffreykolovson • Uncapped | Comparative Advantages w/ Keith Rabois: https://www.khoslaventures.com/posts/uncapped-comparative-advantages-w-keith-rabois • Lattice: https://lattice.com • Taylor Francis on LinkedIn: https://www.linkedin.com/in/taylor-francis-4ba49640 • Building product at Stripe: craft, metrics, and customer obsession | Jeff Weinstein (Product lead): https://www.lennysnewsletter.com/p/building-product-at-stripe-jeff-weinstein • The art of hiring: insights from Khosla Ventures, Airbnb, Ramp and Traba: https://ramp.com/velocity/the-art-of-hiring-insights • Eric Glyman: Seek out super individual contributors (ICs): https://ramp.com/velocity/the-art-of-hiring-insights#Eric-Glyman:-Seek-out-super-individual-contributors-(ICs) • Eric Glyman on X: https://x.com/eglyman • Mike Moore on LinkedIn: https://www.linkedin.com/in/mike-moore-802223177 • Brian Chesky’s new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach • Why you should work much harder RIGHT NOW: https://marginalrevolution.com/marginalrevolution/2026/03/why-you-should-work-much-harder-right-now.html • Opendoor: https://www.opendoor.com • The Craft of Early Stage Venture | Peter Fenton, General Partner at Benchmark | Uncapped with Jack Altman: https://www.youtube.com/watch?v=vRiblwiXt-Q • Lovable: https://lovable.dev • The rise of the professional vibe coder (a new AI-era job) | Lazar Jovanovic (Professional Vibe Coder): https://www.lennysnewsletter.com/p/getting-paid-to-vibe-code • Building Lovable: $10M ARR in 60 days with 15 people | Anton Osika (co-founder and CEO): https://www.lennysnewsletter.com/p/building-lovable-anton-osika • Marc Andreessen: The real AI boom hasn’t even started yet: https://www.lennysnewsletter.com/p/marc-andreessen-the-real-ai-boom • Jeremy Stoppelman on X: https://x.com/jeremys • The design process is dead. Here’s what’s replacing it. | Jenny Wen (head of design at Claude): https://www.lennysnewsletter.com/p/the-design-process-is-dead • Andy Warhol: https://en.wikipedia.org/wiki/Andy_Warhol • Curation and Algorithms: https://stratechery.com/2015/curation-and-algorithms • Ernest Hemingway: https://en.wikipedia.org/wiki/Ernest_Hemingway • William Shakespeare: https://en.wikipedia.org/wiki/William_Shakespeare • Evan Moore on X: https://x.com/evancharles • Andrew Mason on X: https://x.com/andrewmason • Read Taylor Swift’s Full Viral Speech After Record-Breaking Awards Sweep: https://www.newsweek.com/entertainment/read-taylor-swift-full-acceptance-speech-record-breaking-awards-sweep-11745941 • The Chainsmokers: Stories Behind the Songs, AI’s Impact on Music, and Venture Investing | Uncapped with Jack Altman: https://www.youtube.com/watch?v=9GMSC-2pYnw&list=PLtpH7YnTL8ihy0nR2BV32n5VkRtqlDAS1&index=16 • How to spot a top 1% startup early: https://www.lennysnewsletter.com/p/how-to-spot-a-top-1-startup-early • David Weiden on LinkedIn: https://www.linkedin.com/in/davidweiden • Alfred Lin on LinkedIn: https://www.linkedin.com/in/linalfred • Keith’s post about vertical integration on X: https://x.com/rabois/status/870673635375104000 • Jon Chu on X: https://x.com/jonchu • Kanu Gulati on X: https://x.com/KanuGulati • Rogo: https://rogo.ai • Profound: https://www.tryprofound.com • Basis: https://www.getbasis.ai • Spellbook: https://www.spellbook.legal • Roelof Botha on X: https://x.com/roelofbotha • Delian Asparouhov on LinkedIn: https://www.linkedin.com/in/delian-asparouhov-87447742 • Lessons From Keith Rabois, Essay 1: How to become a Venture Capitalist: https://delian.io/lessons-1 • 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 • Nuremberg on AppleTV+: https://tv.apple.com/us/movie/nuremberg/umc.cmc.3sg4y0382byupy76bfy7307k4 • Eight Sleep: https://www.eightsleep.com • “NO DAYS OFF”—Bill Belichick on X: https://x.com/SNFonNBC/status/829036279069364224 — Recommended books: • Creativity, Inc.: Overcoming the Unseen Forces That Stand in the Way of True Inspiration: https://www.amazon.com/Creativity-Inc-Overcoming-Unseen-Inspiration/dp/0812993012 • The Jordan Rules: The Inside Story of One Turbulent Season with Michael Jordan and the Chicago Bulls: https://www.amazon.com/Jordan-Rules-Sam-Smith/dp/0671796666 • The Upside of Stress: Why Stress Is Good for You, and How to Get Good at It: https://www.amazon.com/Upside-Stress-Why-Good-You/dp/1101982934 — 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
April 5 · 1 hr 52 min
Head of Growth (Anthropic): “Claude is growing itself at this point” | Amol Avasare
Amol Avasare is Head of Growth at Anthropic, which is going through the most unprecedented growth trajectory in history—scaling from $1 billion to over $19 billion in ARR in just 14 months. Previously, Amol worked on the growth teams at Mercury and MasterClass. Before that he was a founder, and he cold emailed his way into the Anthropic role when no job listing existed. Most remarkably, he overcame a traumatic brain injury from a Muay Thai match that meant he couldn't work for nearly a year. In our in-depth discussion, Amol shares: 1. How Amol landed his role by cold emailing Anthropic’s CPO Mike Krieger 2. How Anthropic is automating growth experiments with Claude (their internal tool called “CASH”) 3. Why the ratio of PMs to engineers might need to flip (more PMs than engineers) as AI makes engineers exponentially more productive 4. Why activation is the single highest-leverage growth problem in AI 5. Why Anthropic indexes 70/30 toward big bets (the opposite of most growth teams) 6. How he uses Cowork to detect team misalignment in Slack 7. How the company’s focus on AI coding created a research flywheel that accelerated their models — Brought to you by: WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs Vanta—Automate compliance, manage risk, and accelerate trust with AI — Episode transcript: https://www.lennysnewsletter.com/p/anthropics-1b-to-19b-growth-run — Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0 — Where to find Amol Avasare: • X: https://x.com/TheAmolAvasare • LinkedIn: https://www.linkedin.com/in/amolavasare — 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 Amol and Anthropic’s growth (03:15) The story of cold emailing Mike Krieger to get the job (08:28) What it’s like leading growth at the fastest-growing company ever (10:46) What the growth team actually does at Anthropic (12:16) The concept of “success disasters” (13:55) Why activation is the biggest challenge in AI products (18:05) Improving Mercury’s onboarding experience (20:57) The importance of adding the right kind of friction (25:10) Anthropic’s org structure (27:06) Why Anthropic focuses on big bets over micro-optimizations (33:34) Automating growth experiments with Claude (CASH) (38:20) How AI is starting to identify what experiments to run (41:07) The future of PM, engineering, and design roles (47:19) Why you might need more PMs as engineers get more productive (51:13) How Amol uses AI to prototype ideas and skip PRDs (58:10) Amol’s morning routine: AI analyzes 20 to 25 charts automatically (1:03:31) Getting coaching from an AI version of your manager (1:06:27) How Anthropic’s focus on coding and B2B drove their success (1:12:10) Balancing growth with AI safety as a core mission (1:18:09) Advice for thriving in an AI-first future (1:22:53) Anthropic’s culture and the “notebook channels” on Slack (1:35:12) Failure corner: Shutting down his startup after raising money (1:38:25) The traumatic brain injury that changed everything (1:46:49) Lightning round — References: https://www.lennysnewsletter.com/p/anthropics-1b-to-19b-growth-run — 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
April 2 · 1 hr 39 min
An AI state of the union: We’ve passed the inflection point, dark factories are coming, and automation timelines | Simon Willison
Simon Willison is a prolific independent software developer, a blogger, and one of the most visible and trusted voices on the impact AI is having on builders. He co-created Django, the web framework that powers Instagram, Pinterest, and tens of thousands of other websites. He coined the term “prompt injection,” popularized the terms “AI slop” and “agentic engineering,” and has built over 100 open source projects, including Datasette, a data analysis tool used by investigative journalists worldwide. What makes Simon unique is that he’s made the leap from traditional software engineering to AI-native development more fully and visibly than almost anyone—and he’s been documenting everything he learns in real time on his blog, SimonWillison.net. In our in-depth conversation, Simon shares: 1. Why November 2025 was the inflection point when AI coding agents crossed from “mostly works” to “actually works” 2. How Simon writes 95% of his code from his phone now and why he’s mentally exhausted by 11 a.m. 3. Why mid-career engineers (not juniors) are most at risk right now 4. The three agentic engineering patterns Simon uses daily (red/green TDD, templates, hoarding) 5. The next leap: the “dark factory” pattern where nobody writes or reviews code and AI does its own QA 6. Why prompt injection is an unsolved security problem and the “lethal trifecta” that will likely lead to an AI Challenger disaster 7. Why the pelican riding a bicycle became the unofficial benchmark for AI model quality — Brought to you by: WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs Vanta—automate compliance, manage risk, and accelerate trust with AI — Episode transcript: https://www.lennysnewsletter.com/p/an-ai-state-of-the-union — Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0 — Where to find Simon Willison: • X: https://x.com/simonw • LinkedIn: https://www.linkedin.com/in/simonwillison • Website: https://simonwillison.net • Agentic Engineering Patterns: https://simonwillison.net/guides/agentic-engineering-patterns — 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 Simon Willison (02:40) The November 2025 inflection point (08:01) What’s possible now with AI coding (10:42) Vibe coding vs. agentic engineering (13:57) The dark-factory pattern (20:41) Where bottlenecks have shifted (23:36) Where human brains will continue to be valuable (25:32) Defending of software engineers (29:12) Why experienced engineers get better results (30:48) Advice for avoiding the permanent underclass (33:52) Leaning into AI to amplify your skills (35:12) Why Simon says he’s working harder than ever (37:23) The market for pre-2022 human-written code (40:01) Prediction: 50% of engineers writing 95% AI code by the end of 2026 (44:34) The impact of cheap code (48:27) Simon’s AI stack (54:08) Using AI for research (55:12) The pelican-riding-a-bicycle benchmark (59:01) The inherent ridiculousness of AI (1:00:52) Hoarding things you know how to do (1:08:21) Red/green TDD pattern for better AI code (1:14:43) Starting projects with good templates (1:16:31) The lethal trifecta and prompt injection (1:21:53) Why 97% effectiveness is a failing grade (1:25:19) The normalization of deviance (1:28:32) OpenClaw: the security nightmare everyone is looking past (1:34:22) What’s next for Simon (1:36:47) Zero-deliverable consulting (1:38:05) Good news about Kakapo parrots — References: https://www.lennysnewsletter.com/p/an-ai-state-of-the-union — 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
March 29 · 1 hr 46 min
From skeptic to true believer: How OpenClaw changed my life | Claire Vo
Claire Vo is the host of our sister podcast, “How I AI,” a former product executive and engineer, and founder of an AI startup called ChatPRD. Claire now runs her business, podcast, and family life with the help of nine OpenClaw agents running on multiple Mac Minis and old laptops. In this episode, Claire shares her journey from OpenClaw skeptic (it deleted her family calendar the first time she tried it) to true believer, and gives a masterclass in using AI agents in real life. We discuss: 1. The exact step-by-step process to install and set up OpenClaw (it’s easier than you think) 2. How to avoid the biggest OpenClaw mistakes (don’t install it on your main computer) 3. Actual use cases that have changed Claire’s life (e.g. family scheduling, inbound sales, podcast prep, and course management) 4. Why multiple specialized agents beat one general-purpose agent 5. The security risks everyone worries about—and how to handle them 6. Browser limitations, memory issues, and practical workarounds — Brought to you by: Mercury—Radically different banking Omni—AI analytics your customers can trust Orkes—The enterprise platform for reliable applications and agentic workflows — Where to find Claire Vo: • X: https://x.com/clairevo • LinkedIn: https://www.linkedin.com/in/clairevo • Podcast: https://www.youtube.com/@howiaipodcast • Website: https://clairevo.com • ChatPRD: https://www.chatprd.ai — 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 Claire and OpenClaw (08:00) The journey from OpenClaw skeptic to believer (11:50) What OpenClaw actually does that’s useful (13:35) OpenClaw vs. other AI agent products (17:05) How to actually install OpenClaw: the basics (18:49) Setting up like you’d onboard a real assistant (20:41) Security and privacy considerations (24:53) Live demo: Installing OpenClaw step-by-step (28:47) Setting up Q: an agent for her kids’ homework (34:08) Understanding “soul,” “identity,” and “memory” (40:40) The unlock: multiple agents, not just one (45:02) How to run multiple agents on one machine (47:28) Jesse Genet’s homeschooling use case (49:58) Real examples and use cases (56:41) Finn, Claire’s family agent (1:00:05) Sage the Course Bot (1:02:15) Common issues and workarounds (1:08:08) The Exa/Perplexity web search workaround (1:09:29) Memory management and context overload (1:12:09) Pro tip: Screen sharing to manage Mac Minis (1:14:18) Using Google Workspace for agent collaboration (1:16:24) What makes OpenClaw special (1:20:15) The “yappers API” and ramble mode (1:22:04) Using Claude Code as your OpenClaw brain surgeon (1:25:16) Bringing management skills to AI agents (1:29:32) Why this matters (1:32:37) Lightning round and final thoughts — Referenced: • OpenClaw: https://openclaw.ai • Claude Cowork: https://claude.com/product/cowork • Fry’s Electronics: https://en.wikipedia.org/wiki/Fry%27s_Electronics • Peter Steinberger on LinkedIn: https://www.linkedin.com/in/steipete • Telegram: https://telegram.org • WhatsApp: https://www.whatsapp.com • Fin: https://fin.ai • Why OpenClaw feels alive even though it’s not (this AI has a heartbeat but not a brain): https://x.com/clairevo/status/2017741569521271175 • 5 OpenClaw agents run my home, finances, and code | Jesse Genet: https://www.youtube.com/watch?v=96Vl8s3EQhk • Executive Playbook for AI in Engineering, Product, and Design: https://maven.com/clairevo/ai-native-epd-org • Zach Davis on LinkedIn: https://www.linkedin.com/in/zach-m-davis/ • ChatGPT Atlas: https://chatgpt.com/atlas • Perplexity Comet: https://www.perplexity.ai/comet • Browser (OpenClaw-managed): https://docs.openclaw.ai/tools/browser • Buffer: https://buffer.com • Brave: https://brave.com/search/api/ • Exa: https://exa.ai • Hilary Gridley on X: https://x.com/yourgirlhils • 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.youtube.com/watch?v=xDMkkOC-EhI • How to debug a team that isn’t working: the Waterline Model: https://www.lennysnewsletter.com/p/how-to-debug-a-team-that-isnt-working • Jensen Huang on LinkedIn: https://www.linkedin.com/in/jenhsunhuang • How I built a 1M+ subscriber newsletter and top 10 tech podcast | Lenny Rachitsky: https://www.lennysnewsletter.com/p/how-i-built-a-1m-subscriber-newsletter • Age of Attraction on Netflix: https://www.netflix.com/title/81779095 • Oura Ring: https://ouraring.com/ • Eight Sleep: https://www.eightsleep.com • Hoopsalytics: https://hoopsalytics.com • DJI Osmo smartphone gimbal: https://www.amazon.com/DJI-Stabilizer-Tracking-Extension-Stabilization/dp/B0FJ2L67HJ?ref_=ast_sto_dp • Silent basketball: https://www.amazon.com/Rzkipdy-Silent-Basketball-Size-27-5/dp/B0FHFSQWPP/ref=sr_1_9 • Marc Andreessen: The real AI boom hasn’t even started yet: https://www.lennysnewsletter.com/p/marc-andreessen-the-real-ai-boom — Recommended books: • Treasure Island: https://www.amazon.com/Treasure-Island-Robert-Louis-Stevenson/dp/1505297400 • Alice’s Adventures in Wonderland: https://www.amazon.com/Alices-Adventures-Wonderland-Illustrated-Illustrations/dp/991673268X • Charts for Babies: A Picture Book: https://www.amazon.com/Charts-Babies-Picture-Book/dp/1419785184 — 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

Lenny's Podcast: Product | Career | Growth

Anthropic’s first technical PM on token maxing, the jagged edge, and living in the future | Dianne Penn

Why Netflix is betting on systems thinkers—not specialists—in the AI era | Elizabeth Stone (CPTO)

How tech workers actually feel about AI in 2026 | Annual AI sentiment survey (Noam Segal)

Adam Mosseri: AI is a tailwind for authenticity

OpenAI Codex lead on the new shape of product work | Andrew Ambrosino

What happens after coding is solved? | Fiona Fung (Manager of the Claude Code and Cowork Teams)

The hidden pattern behind successful products | Mark Pincus (founder of Zynga)

Father of the iPod and iPhone on building taste, judgment, and creativity in the AI era | Tony Fadell

A rational conversation on where AI is actually going | Benedict Evans

The AI paradox: More automation, more humans, more work | Dan Shipper

Why we’re at the beginning of the AI hardware boom | Caitlin Kalinowski (ex–OpenAI, Meta, Apple)

How to build a company that withstands any era | Eric Ries, Lean Startup author

Why cultivating agency matters more than cultivating skills in the AI era | Max Schoening (Head of Product, Notion)

Snapchat CEO: Why distribution has become the most important moat | Evan Spiegel

How Anthropic’s product team moves faster than anyone else | Cat Wu (Head of Product, Claude Code)

Why half of product managers are in trouble | Nikhyl Singhal (Meta, Google)

Hard truths about building in the AI era | Keith Rabois (Khosla Ventures)

Head of Growth (Anthropic): “Claude is growing itself at this point” | Amol Avasare

An AI state of the union: We’ve passed the inflection point, dark factories are coming, and automation timelines | Simon Willison

From skeptic to true believer: How OpenClaw changed my life | Claire Vo