Lenny's Podcast: Product | Career | Growth cover art

Lenny's Podcast: Product | Career | Growth

Lenny's Podcast: Product | Career | Growth

By: Lenny Rachitsky
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 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.Lenny Rachitsky Economics Leadership Management & Leadership
Episodes
  • Hard truths about building in the AI era | Keith Rabois (Khosla Ventures)

    Hard truths about building in the AI era | Keith Rabois (Khosla Ventures)
    Apr 12 2026
    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 products3. How to identify undiscovered talent4. Why the PM role is dying5. The three traits of the best-performing companies right now6. The specific interview question he asks every senior candidate7. 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 MAUsVanta—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• ...
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    1 hr and 23 mins
  • Anthropic’s $1B to $19B growth run: how Claude became the fastest-growing AI product in history | Amol Avasare

    Anthropic’s $1B to $19B growth run: how Claude became the fastest-growing AI product in history | Amol Avasare
    Apr 5 2026
    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 Krieger2. 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 productive4. Why activation is the single highest-leverage growth problem in AI5. Why Anthropic indexes 70/30 toward big bets (the opposite of most growth teams)6. How he uses Cowork to detect team misalignment in Slack7. 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 MAUsVanta—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
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    1 hr and 53 mins
  • An AI state of the union: We’ve passed the inflection point, dark factories are coming, and automation timelines | Simon Willison

    An AI state of the union: We’ve passed the inflection point, dark factories are coming, and automation timelines | Simon Willison
    Apr 2 2026
    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 now4. 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 QA6. Why prompt injection is an unsolved security problem and the “lethal trifecta” that will likely lead to an AI Challenger disaster7. 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 MAUsVanta—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
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    1 hr and 40 mins
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