Lenny's Podcast: Product | Career | Growth

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 [https://workos.com/lenny]—Modern identity platform for B2B SaaS, free up to 1 million MAUs Vanta [https://vanta.com/lenny]—Automate compliance, manage risk, and accelerate trust with AI — Episode transcript: https://www.lennysnewsletter.com/p/why-half-of-product-managers-are-in-trouble [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 [https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0] — Where to find Cat Wu: • X: https://x.com/_catwu [https://x.com/_catwu] • LinkedIn: linkedin.com/in/cat-wu [http://linkedin.com/in/cat-wu] • Newsletter: https://catwu.substack.com [https://catwu.substack.com] — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com [https://www.lennysnewsletter.com] • X: https://twitter.com/lennysan [https://twitter.com/lennysan] • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ [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 [https://www.lennysnewsletter.com/p/how-anthropics-product-team-moves] — Production and marketing by https://penname.co/ [https://penname.co/]. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com [podcast@lennyrachitsky.com]. — Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com [https://www.lennysnewsletter.com?utm_medium=podcast&utm_campaign=show-notes-no-free-preview-language]

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 [https://workos.com/lenny]—Modern identity platform for B2B SaaS, free up to 1 million MAUs Vanta [https://vanta.com/lenny]—Automate compliance, manage risk, and accelerate trust with AI — Episode transcript: https://www.lennysnewsletter.com/p/why-half-of-product-managers-are-in-trouble [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 [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 [https://www.linkedin.com/in/nikhyl] • X: https://x.com/nikhyl [https://x.com/nikhyl] • Podcast & Newsletter: https://skip.show [https://skip.show] • Skip Community: https://skip.community [https://skip.community] • Skip Coach: https://skip.coach [https://skip.coach] • Skip.help [http://Skip.help]: https://skip.help [https://skip.help] — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com [https://www.lennysnewsletter.com] • X: https://twitter.com/lennysan [https://twitter.com/lennysan] • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ [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 [https://www.lennysnewsletter.com/p/building-a-long-and-meaningful-career] • COBOL: https://en.wikipedia.org/wiki/COBOL [https://en.wikipedia.org/wiki/COBOL] • United Airlines: https://www.united.com [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 [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 [https://www.lennysnewsletter.com/p/anthropics-1b-to-19b-growth-run] • Demis Hassabis on X: https://x.com/demishassabis [https://x.com/demishassabis] • Sam Altman on X: https://x.com/sama [https://x.com/sama] • Dario Amodei on X: https://x.com/DarioAmodei [https://x.com/DarioAmodei] • Cross on Prime Video: https://www.amazon.com/Cross-Season-1/dp/B0D6X7ZZHC [https://www.amazon.com/Cross-Season-1/dp/B0D6X7ZZHC] • Jack Ryan on Prime Video: https://www.amazon.com/Tom-Clancys-Jack-Ryan/dp/B0CNDCMN8R [https://www.amazon.com/Tom-Clancys-Jack-Ryan/dp/B0CNDCMN8R] • 24 on Prime Video: https://www.amazon.com/24-Season-1/dp/B000HPF85A [https://www.amazon.com/24-Season-1/dp/B000HPF85A] • Claude Code: https://code.claude.com [https://code.claude.com] • Codex: https://chatgpt.com/codex [https://chatgpt.com/codex] • Lovable: https://lovable.dev [https://lovable.dev] • Sonos: https://www.sonos.com [https://www.sonos.com] • “There are only four jobs” on X: https://x.com/yrechtman/status/2039012253341495462 [https://x.com/yrechtman/status/2039012253341495462] • Paradise on Hulu: https://www.hulu.com/series/paradise-2b4b8988-50c9-4097-bf93-bc34a99a5b4f [https://www.hulu.com/series/paradise-2b4b8988-50c9-4097-bf93-bc34a99a5b4f] • Lioness on Paramount+: https://www.paramountplus.com/shows/lioness [https://www.paramountplus.com/shows/lioness] • Tesla: https://www.tesla.com [https://www.tesla.com] • Albert Einstein’s quote: https://www.goodreads.com/quotes/115696-genius-is-1-talent-and-99-percent-hard-work [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 [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 [https://www.amazon.com/Adventures-Huckleberry-Finn-Unabridged-Uncensored/dp/195483943X] — Production and marketing by https://penname.co/ [https://penname.co/]. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com [podcast@lennyrachitsky.com]. — Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com [https://www.lennysnewsletter.com?utm_medium=podcast&utm_campaign=show-notes-no-free-preview-language]

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 [https://workos.com/lenny]—Modern identity platform for B2B SaaS, free up to 1 million MAUs Vanta [https://vanta.com/lenny]—automate compliance, manage risk, and accelerate trust with AI — Episode transcript: https://www.lennysnewsletter.com/p/hard-truths-about-building-in-the-ai-era [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 [https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0] — Where to find Keith Rabois: • X: https://x.com/rabois [https://x.com/rabois] • LinkedIn: linkedin.com/in/keith [http://linkedin.com/in/keith] • Website: https://www.khoslaventures.com [https://www.khoslaventures.com] — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com [https://www.lennysnewsletter.com] • X: https://twitter.com/lennysan [https://twitter.com/lennysan] • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ [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 [https://squareup.com] • Jack Dorsey on X: https://x.com/jack [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 [https://www.lennysnewsletter.com/p/head-of-claude-code-what-happens] • Simon Willison’s Weblog: https://simonwillison.net [https://simonwillison.net] • Vinod Khosla on X: https://x.com/vkhosla [https://x.com/vkhosla] • Peter Thiel on X: https://x.com/peterthiel [https://x.com/peterthiel] • Max Levchin on X: https://x.com/mlevchin [https://x.com/mlevchin] • David Sacks on LinkedIn: https://www.linkedin.com/in/davidoliversacks [https://www.linkedin.com/in/davidoliversacks] • Tony Xu on X: https://x.com/t_xu [https://x.com/t_xu] • David Sze on X: https://x.com/davidsze [https://x.com/davidsze] • Faire: https://www.faire.com [https://www.faire.com] • Max Rhodes on X: https://x.com/MaxRhodesOK [https://x.com/MaxRhodesOK] • Jeffrey Kolovson on LinkedIn: https://www.linkedin.com/in/jeffreykolovson [https://www.linkedin.com/in/jeffreykolovson] • Uncapped | Comparative Advantages w/ Keith Rabois: https://www.khoslaventures.com/posts/uncapped-comparative-advantages-w-keith-rabois [https://www.khoslaventures.com/posts/uncapped-comparative-advantages-w-keith-rabois] • Lattice: https://lattice.com [https://lattice.com] • Taylor Francis on LinkedIn: https://www.linkedin.com/in/taylor-francis-4ba49640 [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 [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 [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) [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 [https://x.com/eglyman] • Mike Moore on LinkedIn: https://www.linkedin.com/in/mike-moore-802223177 [https://www.linkedin.com/in/mike-moore-802223177] • Brian Chesky’s new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach [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 [https://marginalrevolution.com/marginalrevolution/2026/03/why-you-should-work-much-harder-right-now.html] • Opendoor: https://www.opendoor.com [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 [https://www.youtube.com/watch?v=vRiblwiXt-Q] • Lovable: https://lovable.dev [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 [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 [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 [https://www.lennysnewsletter.com/p/marc-andreessen-the-real-ai-boom] • Jeremy Stoppelman on X: https://x.com/jeremys [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 [https://www.lennysnewsletter.com/p/the-design-process-is-dead] • Andy Warhol: https://en.wikipedia.org/wiki/Andy_Warhol [https://en.wikipedia.org/wiki/Andy_Warhol] • Curation and Algorithms: https://stratechery.com/2015/curation-and-algorithms [https://stratechery.com/2015/curation-and-algorithms] • Ernest Hemingway: https://en.wikipedia.org/wiki/Ernest_Hemingway [https://en.wikipedia.org/wiki/Ernest_Hemingway] • William Shakespeare: https://en.wikipedia.org/wiki/William_Shakespeare [https://en.wikipedia.org/wiki/William_Shakespeare] • Evan Moore on X: https://x.com/evancharles [https://x.com/evancharles] • Andrew Mason on X: https://x.com/andrewmason [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 [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 [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 [https://www.lennysnewsletter.com/p/how-to-spot-a-top-1-startup-early] • David Weiden on LinkedIn: https://www.linkedin.com/in/davidweiden [https://www.linkedin.com/in/davidweiden] • Alfred Lin on LinkedIn: https://www.linkedin.com/in/linalfred [https://www.linkedin.com/in/linalfred] • Keith’s post about vertical integration on X: https://x.com/rabois/status/870673635375104000 [https://x.com/rabois/status/870673635375104000] • Jon Chu on X: https://x.com/jonchu [https://x.com/jonchu] • Kanu Gulati on X: https://x.com/KanuGulati [https://x.com/KanuGulati] • Rogo: https://rogo.ai [https://rogo.ai] • Profound: https://www.tryprofound.com [https://www.tryprofound.com] • Basis: https://www.getbasis.ai [https://www.getbasis.ai] • Spellbook: https://www.spellbook.legal [https://www.spellbook.legal] • Roelof Botha on X: https://x.com/roelofbotha [https://x.com/roelofbotha] • Delian Asparouhov on LinkedIn: https://www.linkedin.com/in/delian-asparouhov-87447742 [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 [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 [https://www.lennysnewsletter.com/p/velocity-over-everything-how-ramp] • Nuremberg on AppleTV+: https://tv.apple.com/us/movie/nuremberg/umc.cmc.3sg4y0382byupy76bfy7307k4 [https://tv.apple.com/us/movie/nuremberg/umc.cmc.3sg4y0382byupy76bfy7307k4] • Eight Sleep: https://www.eightsleep.com [https://www.eightsleep.com] • “NO DAYS OFF”—Bill Belichick on X: https://x.com/SNFonNBC/status/829036279069364224 [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 [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 [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 [https://www.amazon.com/Upside-Stress-Why-Good-You/dp/1101982934] — Production and marketing by https://penname.co/ [https://penname.co/]. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com [podcast@lennyrachitsky.com]. — Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com [https://www.lennysnewsletter.com?utm_medium=podcast&utm_campaign=show-notes-no-free-preview-language]

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 [https://workos.com/lenny]—Modern identity platform for B2B SaaS, free up to 1 million MAUs Vanta [https://vanta.com/lenny]—Automate compliance, manage risk, and accelerate trust with AI — Episode transcript: https://www.lennysnewsletter.com/p/anthropics-1b-to-19b-growth-run [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 [https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0] — Where to find Amol Avasare: • X: https://x.com/TheAmolAvasare [https://x.com/TheAmolAvasare] • LinkedIn: https://www.linkedin.com/in/amolavasare [https://www.linkedin.com/in/amolavasare] — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com [https://www.lennysnewsletter.com] • X: https://twitter.com/lennysan [https://twitter.com/lennysan] • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ [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 [https://www.lennysnewsletter.com/p/anthropics-1b-to-19b-growth-run] — Production and marketing by https://penname.co/ [https://penname.co/]. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com [podcast@lennyrachitsky.com]. — Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com [https://www.lennysnewsletter.com?utm_medium=podcast&utm_campaign=show-notes-no-free-preview-language]

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 [http://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 [https://workos.com/lenny]—Modern identity platform for B2B SaaS, free up to 1 million MAUs Vanta [https://vanta.com/lenny]—automate compliance, manage risk, and accelerate trust with AI — Episode transcript: https://www.lennysnewsletter.com/p/an-ai-state-of-the-union [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 [https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0] — Where to find Simon Willison: • X: https://x.com/simonw [https://x.com/simonw] • LinkedIn: https://www.linkedin.com/in/simonwillison [https://www.linkedin.com/in/simonwillison] • Website: https://simonwillison.net [https://simonwillison.net] • Agentic Engineering Patterns: https://simonwillison.net/guides/agentic-engineering-patterns [https://simonwillison.net/guides/agentic-engineering-patterns] — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com [https://www.lennysnewsletter.com] • X: https://twitter.com/lennysan [https://twitter.com/lennysan] • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ [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 [https://www.lennysnewsletter.com/p/an-ai-state-of-the-union] — Production and marketing by https://penname.co/ [https://penname.co/]. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com [podcast@lennyrachitsky.com]. — Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com [https://www.lennysnewsletter.com?utm_medium=podcast&utm_campaign=show-notes-no-free-preview-language]