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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
  • Head of Claude Code: What happens after coding is solved | Boris Cherny

    Head of Claude Code: What happens after coding is solved | Boris Cherny
    Feb 19 2026
    Boris Cherny is the creator and head of Claude Code at Anthropic. What began as a simple terminal-based prototype just a year ago has transformed the role of software engineering and is increasingly transforming all professional work.We discuss:1. How Claude Code grew from a quick hack to 4% of public GitHub commits, with daily active users doubling last month2. The counterintuitive product principles that drove Claude Code’s success3. Why Boris believes coding is “solved”4. The latent demand that shaped Claude Code and Cowork5. Practical tips for getting the most out of Claude Code and Cowork6. How underfunding teams and giving them unlimited tokens leads to better AI products7. Why Boris briefly left Anthropic for Cursor, then returned after just two weeks8. Three principles Boris shares with every new team member—Brought to you by:DX—The developer intelligence platform designed by leading researchers: https://getdx.com/lennySentry—Code breaks, fix it faster: https://sentry.io/lennyMetaview—The AI platform for recruiting: https://metaview.ai/lenny—Episode transcript: https://www.lennysnewsletter.com/p/head-of-claude-code-what-happens—Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0—Where to find Boris Cherny:• X: https://x.com/bcherny• LinkedIn: https://www.linkedin.com/in/bcherny• Website: https://borischerny.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 Boris and Claude Code(03:45) Why Boris briefly left Anthropic for Cursor (and what brought him back)(05:35) One year of Claude Code(08:41) The origin story of Claude Code(13:29) How fast AI is transforming software development(15:01) The importance of experimentation in AI innovation(16:17) Boris’s current coding workflow (100% AI-written)(17:32) The next frontier(22:24) The downside of rapid innovation (24:02) Principles for the Claude Code team(26:48) Why you should give engineers unlimited tokens(27:55) Will coding skills still matter in the future?(32:15) The printing press analogy for AI’s impact(36:01) Which roles will AI transform next?(40:41) Tips for succeeding in the AI era(44:37) Poll: Which roles are enjoying their jobs more with AI(46:32) The principle of latent demand in product development(51:53) How Cowork was built in just 10 days(54:04) The three layers of AI safety at Anthropic(59:35) Anxiety when AI agents aren’t working(01:02:25) Boris’s Ukrainian roots(01:03:21) Advice for building AI products(01:08:38) Pro tips for using Claude Code effectively(01:11:16) Thoughts on Codex(01:12:13) Boris’s post-AGI plans(01:14:02) Lightning round and final thoughts—References: https://www.lennysnewsletter.com/p/head-of-claude-code-what-happens—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 28 mins
  • Sequoia CEO coach: Why it’s never been easier to start a company, and never been harder to scale one | Brian Halligan (co-founder, HubSpot)

    Sequoia CEO coach: Why it’s never been easier to start a company, and never been harder to scale one | Brian Halligan (co-founder, HubSpot)
    Feb 15 2026
    Brian Halligan co-founded HubSpot, ran it as CEO for about 15 years, and now coaches Sequoia’s fastest-growing founders as their in-house CEO coach.We discuss:1. His LOCKS framework for evaluating founders2. Why you should build your team like the 2004 Red Sox3. Why hiring “spicy” candidates beats consensus picks4. Why enterprise sales will be the last white-collar job AI replaces5. Some of my favorite “Halliganisms”—Brought to you by:Sentry—Code breaks, fix it faster: http://sentry.io/lennyDatadog—Now home to Eppo, the leading experimentation and feature flagging platform: https://www.datadoghq.com/lennyWorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs: https://workos.com/lenny—Episode transcript: https://www.lennysnewsletter.com/p/sequoia-ceo-coach-why-its-never-been—Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0—Where to find Brian Halligan• X: https://x.com/bhalligan• LinkedIn: linkedin.com/in/brianhalligan• Delphi: https://www.delphi.ai/bhalligan• Podcast: https://sequoiacap.com/series/long-strange-trip—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 Brian Halligan(03:56) The perpetual state of constructive dissatisfaction(05:25) Coaching CEOs(07:49) The art of interviewing and hiring(11:21) Getting the most out of reference calls(13:10) Homegrown talent vs. big company hires(16:31) Traits of successful CEOs(19:40) Brian’s LOCKS framework for evaluating founders(21:34) Are great CEO’s born or made?(23:41) Giving effective feedback(25:54) The future of go-to-market strategies(31:56) Understanding forward deployed engineers(34:17) How the CEO role has evolved over the last 20 years(38:10) Halliganisms(01:01:18) The CEO’s role in scaling a company(01:02:41) Lightning round and final thoughts—Referenced:• Dev Ittycheria on LinkedIn: https://www.linkedin.com/in/dittycheria• HubSpot: https://www.hubspot.com• Parker Conrad on LinkedIn: https://www.linkedin.com/in/parkerconrad• McKinsey & Company: https://www.mckinsey.com• Brian Chesky’s new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach• Jensen Huang on LinkedIn: https://www.linkedin.com/in/jenhsunhuang• Winston Weinberg on LinkedIn: https://www.linkedin.com/in/winston-weinberg• James Cadwallader on LinkedIn: https://www.linkedin.com/in/jsca• Gabriel Stengel on LinkedIn: https://www.linkedin.com/in/gabestengel• He saved OpenAI, invented the “Like” button, and built Google Maps: Bret Taylor on the future of careers, coding, agents, and more: https://www.lennysnewsletter.com/p/he-saved-openai-bret-taylor• Scaling Entrepreneurial Ventures: https://orbit.mit.edu/classes/scaling-entrepreneurial-ventures-15.392• OpenClaw: https://openclaw.ai• Ruth Porat on LinkedIn: https://www.linkedin.com/in/ruth-porat• Mike Krzyzewski: https://goduke.com/sports/mens-basketball/roster/coaches/mike-krzyzewski/4159• Dalai Lama’s 18 Rules for Living: https://www.prm.nau.edu/prm205/Dalai-Lama-18-rules-for-living.htm• Zigging vs. zagging: How HubSpot built a $30B company | Dharmesh Shah (co-founder/CTO): https://www.lennysnewsletter.com/p/lessons-from-30-years-of-building• Kareem Amin on LinkedIn: https://www.linkedin.com/in/kareemamin• Glassdoor: https://www.glassdoor.com• Tobi Lütke’s leadership playbook: Playing infinite games, operating from first principles, and maximizing human potential (founder and CEO of Shopify): https://www.lennysnewsletter.com/p/tobi-lutkes-leadership-playbook• Katie Burke on LinkedIn: https://www.linkedin.com/in/katie-burke-965767a• Jerry Garcia: https://en.wikipedia.org/wiki/Jerry_Garcia• Bob Weir: https://en.wikipedia.org/wiki/Bob_Weir• Phil Lesh: https://en.wikipedia.org/wiki/Phil_Lesh• Ron “Pigpen” McKernan: https://en.wikipedia.org/wiki/Ron_%22Pigpen%22_McKernan• Marc Andreessen: The real AI boom hasn’t even started yet: https://www.lennysnewsletter.com/p/marc-andreessen-the-real-ai-boom• The American Revolution: https://www.pbs.org/kenburns/the-american-revolution• Delphi: https://www.delphi.ai• Sonos: https://www.sonos.com• Yamini Rangan on LinkedIn: https://www.linkedin.com/in/yaminirangan• The Boston Red Sox: https://www.mlb.com/redsox—Recommended book:• Marketing Lessons from the Grateful Dead: What Every Business Can Learn from the Most Iconic Band in History: https://www.amazon.com/Marketing-Lessons-Grateful-Dead-Business/dp/0470900520—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 15 mins
  • “Engineers are becoming sorcerers” | The future of software development with OpenAI’s Sherwin Wu

    “Engineers are becoming sorcerers” | The future of software development with OpenAI’s Sherwin Wu
    Feb 12 2026
    Sherwin Wu leads engineering for OpenAI’s API platform, where roughly 95% of engineers use Codex, often working with fleets of 10 to 20 parallel AI agents.We discuss:1. What OpenAI did to cut code review times from 10-15 minutes to 2-3 minutes2. How AI is changing the role of managers3. Why the productivity gap between AI power users and everyone else is widening4. Why “models will eat your scaffolding for breakfast”5. Why the next 12 to 24 months are a rare window where engineers can leap ahead before the role fully transforms—Brought to you by:DX—The developer intelligence platform designed by leading researchersSentry—Code breaks, fix it fasterDatadog—Now home to Eppo, the leading experimentation and feature flagging platform—Episode transcript: https://www.lennysnewsletter.com/p/engineers-are-becoming-sorcerers—Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0—Where to find Sherwin Wu:• X: https://x.com/sherwinwu• LinkedIn: https://www.linkedin.com/in/sherwinwu1—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 Sherwin Wu(03:10) AI’s role in coding at OpenAI(06:53) The future of software engineering with AI(12:26) The stress of managing agents(15:07) Codex and code review automation(19:29) The changing role of engineering managers(24:14) The one-person billion-dollar startup(31:40) Management lessons(37:28) Challenges and best practices in AI deployment(43:56) Hot takes on AI and customer feedback(48:57) Building for future AI capabilities(50:16) Where models are headed in the next 18 months(53:35) Business process automation(57:22) OpenAI’s ecosystem and platform strategy(01:00:50) OpenAI’s mission and global impact(01:05:21) Building on OpenAI’s API and tools(01:08:16) Lightning round and final thoughts—Referenced:• Codex: https://openai.com/codex• 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• OpenClaw: https://openclaw.ai• The creator of Clawd: “I ship code I don’t read”: https://newsletter.pragmaticengineer.com/p/the-creator-of-clawd-i-ship-code• The Sorcerer’s Apprentice: https://en.wikipedia.org/wiki/The_Sorcerer%27s_Apprentice_(Dukas)• Quora: https://www.quora.com• Marc Andreessen: The real AI boom hasn’t even started yet: https://www.lennysnewsletter.com/p/marc-andreessen-the-real-ai-boom• Sarah Friar on LinkedIn: https://www.linkedin.com/in/sarah-friar• Sam Altman on X: https://x.com/sama• Nicolas Bustamante’s “LLMs Eat Scaffolding for Breakfast” post on X: https://x.com/nicbstme/status/2015795605524901957• The Bitter Lesson: http://www.incompleteideas.net/IncIdeas/BitterLesson.html• Overton window: https://en.wikipedia.org/wiki/Overton_window• Developers can now submit apps to ChatGPT: https://openai.com/index/developers-can-now-submit-apps-to-chatgpt• Responses: https://platform.openai.com/docs/api-reference/responses• Agents SDK: https://platform.openai.com/docs/guides/agents-sdk• AgentKit: https://openai.com/index/introducing-agentkit• Ubiquiti: https://ui.com• Jujutsu Kaisen on Crunchyroll: https://www.crunchyroll.com/series/GRDV0019R/jujutsu-kaisen?srsltid=AfmBOoqvfzKQ6SZOgzyJwNQ43eceaJTQA2nUxTQfjA1Ko4OxlpUoBNRB• eero: https://eero.com• Opendoor: https://www.opendoor.com—Recommended books:• Structure and Interpretation of Computer Programs: https://www.amazon.com/Structure-Interpretation-Computer-Programs-Engineering/dp/0262510871• The Mythical Man-Month: Essays on Software Engineering: https://www.amazon.com/Mythical-Man-Month-Software-Engineering-Anniversary/dp/0201835959• There Is No Antimemetics Division: A Novel: https://www.amazon.com/There-No-Antimemetics-Division-Novel/dp/0593983750• Breakneck: China’s Quest to Engineer the Future: https://www.amazon.com/Breakneck-Chinas-Quest-Engineer-Future/dp/1324106034• Apple in China: The Capture of the World’s Greatest Company: https://www.amazon.com/Apple-China-Capture-Greatest-Company/dp/1668053373—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 20 mins
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