Lenny's Podcast: Product | Career | Growth

Jacob Warwick is an executive negotiation coach who helps senior operators negotiate better salary, equity, titles, and severance packages. He has worked with leaders across tech and Hollywood, was previously a founder and CEO himself, and has helped clients secure millions in additional compensation. His approach focuses on collaboration over confrontation, understanding motivations, and treating job searches like enterprise sales processes.We discuss:1. Why a simple “What’s the chance there’s a little more here?” often unlocks a 20% bump2. Why Jacob sees 40% average movement when negotiations are run well3. When negotiation actually starts (hint: it’s much earlier than you think)4. Why information + timing create power5. The biggest mistakes people make when negotiating6. How to navigate the important “What’s your comp expectation?” question without anchoring too low7. Why the best interviews feel more like discovery calls than interrogations—Brought to you by:Orkes—The enterprise platform for reliable applications and agentic workflowsMercury—Radically different bankingOmni—AI analytics your customers can trust—Episode transcript: https://www.lennysnewsletter.com/p/the-tactical-playbook-for-getting-more-comp—Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0—Where to find Jacob Warwick:• Substack: https://www.execsandthecity.com• YouTube: https://www.youtube.com/@ExecsandtheCity• Website: https://www.thinkwarwick.com• Complete Job Search Course: https://www.execsandthecity.com/p/complete-job-search-course—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 Jacob Warwick(04:12) How much comp people leave on the table(07:52) Why you shouldn’t feel greedy asking for more(09:45) What founders should know about negotiation(13:03) How Jacob works behind the scenes(15:35) The biggest mistakes people make when negotiating(19:30) Home-field advantage and controlling the conversation(23:02) The step-by-step approach to negotiating an offer(30:17) Jacob’s passion and why these tips don’t work on kids(32:04) Who should speak first about compensation(35:36) Understanding power(39:52) Breaking out of salary bands by focusing on pain points(45:45) Brief summary(47:20) Selling the vacation: How to visualize success(50:07) Controlling the narrative and planting seeds(59:01) Jacob’s role as hype man(01:01:05) Positioning yourself like a product(01:02:49) Making the process frictionless for hiring managers(01:06:20) Flipping the interview to extract information(01:12:17) Five tactical tips for negotiating comp(01:21:45) What to do when negotiations fall apart(01:25:05) Why negotiation is different for every individual(01:28:55) Why outcomes aren’t predetermined(01:32:52) Wild Hollywood negotiation stories(01:37:35) The first step you should take after getting an offer(01:40:30) Jacob’s personal mission(01:44:42) Lightning round and final thoughts—Referenced:• The ultimate guide to negotiating your comp: https://www.lennysnewsletter.com/p/the-ultimate-guide-to-negotiating• Sam Altman on X: https://x.com/sama• Tom Brady on X: https://x.com/TomBrady• Career Huddle: Interview & Negotiation Master Class with Jacob Warwick: https://www.youtube.com/watch?v=TgjWTiSj8E8• Salesforce: https://www.salesforce.com• Julia Roberts: https://en.wikipedia.org/wiki/Julia_Roberts• Matt Damon: https://en.wikipedia.org/wiki/Matt_Damon• Steven Spielberg: https://en.wikipedia.org/wiki/Steven_Spielberg• Marc Andreessen: The real AI boom hasn’t even started yet: https://www.lennysnewsletter.com/p/marc-andreessen-the-real-ai-boom• Chris Voss’s quote: https://www.goodreads.com/quotes/10181396-remember-never-be-so-sure-of-what-you-want-that• Chris Voss on X: https://x.com/fbinegotiator• Werewolf: https://playwerewolf.co• Modes of persuasion: https://en.wikipedia.org/wiki/Modes_of_persuasion• How to use tactical empathy: https://www.linkedin.com/posts/christophervoss_tacticalempathy-negotiation-customerexperience-activity-7361004118808670212-oeRy• ZOPA, BATNA and Win-Win in Negotiation: https://www.parallelprojecttraining.com/blog/zopa-batna-and-win-win-in-negotiation• Marvel: https://www.marvel.com• Negotiation Made Simple podcast: https://www.buzzsprout.com/2227030• Luca on Disney+: https://www.disneyplus.com/browse/entity-f28b825f-c207-406b-923a-67f85e6d90e0• Minuscule: https://www.youtube.com/user/Minuscule• Claude Cowork: https://claude.com/product/cowork• Macrofactor: https://macrofactor.com• Whoop: https://www.whoop.com• Gemini: https://gemini.google.com/app• The Cody Dieruf Foundation: https://breathinisbelievin.org• Cystic Fibrosis Foundation: https://www.cff.org—Recommended books:• Negotiation Games: https://www.amazon.com/Negotiation-Games-Routledge-Advances-Theory/dp/0415308941• Influence: The Psychology of Persuasion: https://www.amazon.com/Influence-Psychology-Persuasion-Robert-Cialdini/dp/006124189X• You Can Negotiate Anything: How to Get What You Want: https://www.amazon.com/You-Negotiate-Anything-Herb-Cohen/dp/0806541229• Negotiation Made Simple: A Practical Guide for Solving Problems, Building Relationships, and Delivering the Deal: https://www.amazon.com/Negotiation-Made-Simple-Relationships-Delivering/dp/1400336325• Radical Candor: Be a Kick-Ass Boss Without Losing Your Humanity: https://www.amazon.com/Radical-Candor-Kick-Ass-Without-Humanity/dp/1250103509• High Output Management: https://www.amazon.com/High-Output-Management-Andrew-Grove/dp/0679762884• How to Win Friends and Influence People: https://www.amazon.com/How-Win-Friends-Influence-People/dp/0671027034—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

People have been asking me to sit on the other side of the mic for a long time. With my wife’s debut children’s book, Charts for Babies, coming out next month, we figured: why not do it together? What followed was one of the most honest conversations I’ve had on this podcast. Michelle asked things no one else would think to ask—and many things I’ve never shared publicly. You’ll hear about the specific moments that pushed me to start the newsletter, how I think about quality and iteration, what most stresses me out, and the scariest moment of my life. This was so fun, and so special, and I hope you like it.We discuss:1. The collection of moments that led me to what I do now2. When I added a paywall, and how I knew it was working3. The hidden treadmill behind shipping a newsletter post and podcast episode every week4. The most stressful moments I’ve had in business and in life5. How I think about stress, consistency, and keeping the business small—Pre-order Charts for Babies: https://www.amazon.com/Charts-Babies-Picture-Book/dp/1419785184—Brought to you by:WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs: https://workos.com/lennyMetaview—The AI platform for recruiting: https://metaview.ai/lennyDX—The developer intelligence platform designed by leading researchers: https://getdx.com/lenny—Episode transcript: https://www.lennysnewsletter.com/p/how-i-built-a-1m-subscriber-newsletter—Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0—Where to find Michelle Rial:• X: https://x.com/TheRialMichelle• LinkedIn: https://www.linkedin.com/in/michellerial• Website: https://www.michellerial.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 and role reversal(04:06) What would Lenny be doing without the newsletter?(07:20) The moments that led to starting the newsletter(09:58) Does Lenny still enjoy the work?(12:42) Stress management and misophonia(14:00) The psychedelic trip that changed everything(15:45) Online happiness course and baseline optimization(17:30) Thunder round: Lenny’s misophonia worst sounds(20:20) What makes Michelle’s charts so shareable(23:55) Where chart ideas come from (and why meditation helps)(26:59) Where does “Lenny” come from?(28:54) Being recognized in public(31:24) Early projects(36:30) Michelle and Lenny’s yin and yang(37:49) Missing office culture (but not really)(39:37) Lenny’s face blindness(40:47) The $100M fraud attack story(42:50) Michelle’s childbirth emergency(47:22) Michelle’s creative process(51:58) Lenny’s favorite children’s books(54:00) Product management lessons in parenting(55:31) Defining product management in five words(58:23) Why Michelle pivoted to children’s books(01:01:30) The power of iteration and real experience—Resources and episode mentions: https://www.lennysnewsletter.com/p/how-i-built-a-1m-subscriber-newsletter—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com. To hear more, visit www.lennysnewsletter.com

Qasar Younis is the co-founder and CEO of Applied Intuition, a $15 billion AI company that adds intelligence to cars, tractors, planes, submarines, and other vehicles—essentially, Tesla or Waymo without the hardware. He was previously COO of Y Combinator, started his career as an engineer at GM and Bosch, and was born on a farm in Pakistan.We discuss:1. Why the biggest AI revolution will play out in mining, farming, construction, and trucking over the next 5 to 10 years, not in software2. Why Qasar intentionally stayed under the radar for nearly a decade while building Applied Intuition, and why most founders shouldn’t do that3. The truth about China’s AI capabilities and why comparisons to American companies are fundamentally flawed4. The company values that drive Applied Intuition: speed above everything, laugh a lot, half the work is follow-up, never disappoint the customer5. The biggest lessons from Qasar’s stint as YC’s COO, including that the most successful companies show traction very early6. How reading old books is the best way to build taste—Brought to you by:Omni—AI analytics your customers can trustVanta—Automate compliance. Simplify security.Lovable—Build apps by simply chatting with AI—Episode transcript: https://www.lennysnewsletter.com/p/the-most-successful-ai-company-youve-never-heard-of—Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0—Where to find Qasar Younis:• X: https://x.com/qasar• LinkedIn: https://www.linkedin.com/in/qasar• Website: https://qy.co• Reading list: https://qy.co/books—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 Qasar and Applied Intuition(04:01) The optimistic vision: How AI will create abundance(08:49) Why anxiety about AI comes from misunderstanding—and how to fight fear with knowledge(12:58) The market sell-off explained(16:31) Self-driving cars: Why 30,000 annual deaths prove we need autonomy now(20:22) The spectrum of physical AI(28:00) How AI is coming just in time(33:26) Why comparing Chinese AI companies to American AI companies is a category error(39:12) Why Qasar finally joined Twitter after staying silent for a decade(45:08) Why successful companies almost always show early signs of traction(50:40) Applied Intuition’s core values(56:00) Why the company cleans its own office—and never spent a dollar of raised capital(58:50) Quasar’s reading philosophy(01:06:14) How to operationalize listening to naysayers(01:12:53) The importance of decisiveness(01:14:55) Removing emotions from decisions(01:19:02) Why most Silicon Valley CEOs don’t have great taste—and how to develop it—Referenced:• Applied Intuition: https://www.appliedintuition.com• Marc Andreessen: The real AI boom hasn’t even started yet: https://www.lennysnewsletter.com/p/marc-andreessen-the-real-ai-boom• Elad Gil’s website: https://eladgil.com• Bosch: https://www.bosch.com• Berkshire Hathaway: https://www.berkshirehathaway.com• Naval Ravikant on X: https://x.com/naval• Y Combinator: https://www.ycombinator.com• Waymo: https://waymo.com/• Tesla: https://www.tesla.com• DeepSeek: https://www.deepseek.com• Rivian: https://rivian.com• Crate & Barrel: https://www.crateandbarrel.com• OpenClaw: https://openclaw.ai• Sam Altman on X: https://x.com/sama• Peter Ludwig on LinkedIn: https://www.linkedin.com/in/peterwludwig• What Steve Jobs really meant when he said ‘Good artists copy; great artists steal’: https://www.cnet.com/tech/tech-industry/what-steve-jobs-really-meant-when-he-said-good-artists-copy-great-artists-steal• 7 quotes on the power of reading from Charlie Munger: https://www.neil.blog/articles/7-quotes-power-reading-charlie-munger• Andreessen Horowitz: https://a16z.com• John Doerr on LinkedIn: https://www.linkedin.com/in/john-doerr-03248211• Gandhi’s quote: https://www.azquotes.com/author/5308-Mahatma_Gandhi/tag/truth#google_vignette• Steve Ballmer on X: https://x.com/Steven_Ballmer• General Motors: https://www.gm.com—Recommended books:• House of Huawei: The Secret History of China’s Most Powerful Company: https://www.amazon.com/House-Huawei-History-Powerful-Company/dp/0593544633• Maintenance: Of Everything, Part One: https://press.stripe.com/maintenance-part-one• The Autobiography of Malcolm X: As Told to Alex Haley: https://www.amazon.com/Autobiography-Malcolm-Told-Alex-Haley/dp/0345350685• High Output Management: https://www.amazon.com/High-Output-Management-Andrew-Grove/dp/0679762884• The Emperor of All Maladies: A Biography of Cancer: https://www.amazon.com/Emperor-All-Maladies-Biography-Cancer/dp/1439170916• Made in America: https://www.amazon.com/Sam-Walton-Made-America/dp/0553562835• My American Journey: https://www.amazon.com/American-Journey-Autobiography-Colin-Powell/dp/0679432965• Guns, Germs, and Steel: The Fates of Human Societies: https://www.amazon.com/Guns-Germs-Steel-Fates-Societies/dp/0393317552• Collapse: How Societies Choose to Fail or Succeed: https://www.amazon.com/Collapse-Societies-Choose-Succeed-Revised/dp/0143117009• SPQR: A History of Ancient Rome: https://www.amazon.com/SPQR-History-Ancient-Mary-Beard/dp/0871404230• A World Appears: A Journey into Consciousness: https://www.amazon.com/World-Appears-Journey-into-Consciousness/dp/198488199X—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

Jenny Wen leads design for Claude at Anthropic. Prior to this, she was Director of Design at Figma, where she led the teams behind FigJam and Slides. Before that, she was a designer at Dropbox, Square, and Shopify.—We discuss:1. Why the classic discovery → mock → iterate design process is becoming obsolete2. What a day in the life of a designer at Anthropic looks like, including her AI tool stack3. Whether AI will eventually surpass humans in taste and judgment4. Why Jenny left a director role at Figma to return to IC work at Anthropic5. The three archetypes Jenny is hiring for now6. Why chatbot interfaces may be more durable than most people expect—Brought to you by:Mercury—Radically different banking: https://mercury.com/?utm_source=lennys&utm_medium=sponsored_newsletter&utm_campaign=26q1_brand_campaignOrkes—The enterprise platform for reliable applications and agentic workflows: https://www.orkes.io/Omni—AI analytics your customers can trust: https://omni.co/lenny—Episode transcript: https://www.lennysnewsletter.com/p/the-design-process-is-dead—Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0—Where to find Jenny Wen:• X: https://x.com/jenny_wen• LinkedIn: https://www.linkedin.com/in/jennywen• Substack: https://jennywen.substack.com• Website: https://jennywen.ca—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 Jenny Wen(04:23) Why the traditional design process is dead(06:33) The two new types of design work(10:00) How widespread this shift will be(13:00) Day-to-day life as a designer at Anthropic(18:45) Jenny’s AI stack(20:03) Why Figma still matters for exploration(22:25) Advice for working with engineers(24:19) How to maintain craft, quality, and trust in the AI era(27:35) Will AI ever have “taste”?(31:38) The future of chatbot interfaces(35:33) Moving from director back to IC(41:00) The 10-day build of Claude Cowork(46:06) Hiring: the three archetypes(50:44) Advice for new and senior designers(54:42) The value of “low leverage” tasks for managers(57:52) Why the best teams roast each other(01:01:45) The legibility framework(01:07:22) Lightning round and final thoughts—Referenced:• Figma: https://www.figma.com• Anthropic: https://www.anthropic.com• v0: https://v0.app• Navigating a Design Career with Jenny Wen | Figma at Waterloo: https://www.youtube.com/watch?v=OHcBPMh2ivk• Claude Cowork: https://claude.com/product/cowork• Use Claude Code in VS Code: https://code.claude.com/docs/en/vs-code• Claude Code in Slack: https://code.claude.com/docs/en/slack• Lex Fridman’s website: https://lexfridman.com• Head of Claude Code: What happens after coding is solved | Boris Cherny: https://www.lennysnewsletter.com/p/head-of-claude-code-what-happens• OpenClaw: https://openclaw.ai• 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• Marc Andreessen: The real AI boom hasn’t even started yet: https://www.lennysnewsletter.com/p/marc-andreessen-the-real-ai-boom• Socratica: https://www.socratica.info• Anthropic’s CPO on what comes next | Mike Krieger (co-founder of Instagram): https://www.lennysnewsletter.com/p/anthropics-cpo-heres-what-comes-next• Radical Candor: From theory to practice with author Kim Scott: https://www.lennysnewsletter.com/p/radical-candor-from-theory-to-practice• Evan Tana’s ‘legibility matrix’ on X: https://x.com/evantana/status/1927404374252269667• How to spot a top 1% startup early: https://www.lennysnewsletter.com/p/how-to-spot-a-top-1-startup-early• Palantir: https://www.palantir.com• Stripe: https://stripe.com• Linear: https://linear.app• Notion: https://www.notion.com• Julie Zhuo’s website: https://www.juliezhuo.com• Sentimental Value: https://www.imdb.com/title/tt27714581• The Pitt on Prime Video: https://www.amazon.com/The-Pitt-Season-1/dp/B0DNRR8QWD• Noah Wyle: https://en.wikipedia.org/wiki/Noah_Wyle• ER on Prime Video: https://www.amazon.com/gp/video/detail/B0FWZSDYRP• Retro: https://retro.app• Granola: https://www.granola.ai—Recommended books:• Radical Candor: Be a Kick-Ass Boss Without Losing Your Humanity: https://www.amazon.com/Radical-Candor-Kick-Ass-Without-Humanity/dp/1250103509• The Power Broker: Robert Moses and the Fall of New York: https://www.amazon.com/Power-Broker-Robert-Moses-Fall/dp/0394480767• Insomniac City: New York, Oliver Sacks, and Me: https://www.amazon.com/Insomniac-City-New-York-Oliver/dp/162040494X—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

Jeetu Patel is the president and chief product officer at Cisco, where he leads a team of 30,000 people and is playing a central role in the massive AI infrastructure buildout happening right now. Previously, he spent five years as CPO at Box and 17 years running his own startup. Recently Jeetu organized an AI summit featuring industry leaders like Jensen Huang, Sam Altman, Marc Andreessen, and Fei-Fei Li.We discuss:1. How Cisco went AI-first across 90,000 employees2. His six-part framework for building great companies: timing, market, team, product, brand, distribution3. Why he says he couldn’t have done this job without AI4. His “right to win” strategic framework5. His communication framework for preventing “packet loss” across an organization6. Why he flips “praise in public, criticize in private” and does the exact opposite7. The important communication lesson his mother taught him—Brought to you by:Sentry—Code breaks, fix it faster: https://sentry.io/lennyFramer—Build better websites faster: https://framer.com/lennySamsara—Saving lives with AI built for physical operations: https://samsara.com/lenny—Episode transcript: https://www.lennysnewsletter.com/p/ai-is-critical-for-humanitys-survival—Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0—Where to find Jeetu Patel:• X: https://x.com/jpatel41• LinkedIn: https://www.linkedin.com/in/jeetupatel• Website: https://blogs.cisco.com/author/jeetupatel—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction and welcome(04:15) Insights from Cisco’s Al summit(08:45) Transforming Cisco into an Al-first company(15:33) What Cisco actually does in the Al infrastructure stack(19:09) The future of Al(24:36) Raising kids in the AI era(29:46) “Permission to play” framework(36:50) Lessons from great CEOs(42:02) Leading at scale(50:54) Why Jeetu inverts the ‘praise in public, criticize in private’ rule(57:45) Surrounding yourself with good human beings(58:35) Lessons from loss(01:03:21) Career advice: platforms, hunger, and preparation(01:10:21) The six-part framework for building great companies(01:19:05) Lightning round and final thoughts—Resources and episode mentions: https://www.lennysnewsletter.com/p/ai-is-critical-for-humanitys-survival—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

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

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

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

Lazar Jovanovic is a full-time professional vibe coder at Lovable. His job is to build both internal tools and customer-facing products purely using AI, while not having a coding background. In this conversation, he breaks down the tactics, workflows, and framework that let him ship production-quality products using only AI.We discuss:1. Why having no coding background can be an advantage when building with AI2. Why most of your time should go to planning and chat mode, not prompting3. What to do when you get stuck: his 4x4 debugging workflow4. The PRD and Markdown file system that keeps AI agents aligned across complex builds5. Why kicking off four or five parallel prototypes is the best way to clarify your thinking6. Why design skills and taste are going to be the most important skills in the future7. His “genie and three wishes” mental model for making the most of AI’s limitations8. How product, engineering, and design roles are converging—and what that means for your career—Brought to you by:Strella—The AI-powered customer research platform: https://strella.io/lennySamsara—Saving lives with AI built for physical operations: https://samsara.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/getting-paid-to-vibe-code—Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0—Where to find Lazar Jovanovic:• X: https://x.com/lakikentaki• LinkedIn: https://www.linkedin.com/in/lazar-jovanovic• YouTube: https://www.youtube.com/@50in50challenge• Starter Story course: https://build.starterstory.com/build/ai-build-accelerator?via=lazar (code LAZAR15 for 15% off)—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 Lazar and professional vibe coding(04:53) What a professional vibe coder actually does day-to-day(09:26) Why non-technical backgrounds can be an advantage(12:24) The importance of self-awareness(14:42) His “genie and three wishes” mental model(17:43) Developing taste and judgment in the age of AI(21:46) The parallel project approach for better outcomes(29:30) Creating dynamic context windows with PRDs(36:56) Why elite vibe coders focus on planning, not coding(44:43) Creating MD files to guide AI development(50:57) Why prototyping still matters(56:50) Why “good enough” is no longer good enough(01:00:53) The future of engineering in an AI world(01:05:14) What to do when you get stuck: his 4x4 debugging workflow(01:14:27) Helping agents learn from their mistakes(01:15:35) Why watching agent output is more important than code(01:19:08) The incredible pace of AI development(01:22:55) Why emotional intelligence will become more valuable(01:28:30) How to become a professional vibe coder(01:30:10) Why building in public is the fastest path to opportunities(01:37:03) Final thoughts on focusing on quality over tech stack—Referenced:• The new AI growth playbook for 2026: How Lovable hit $200M ARR in one year | Elena Verna (Head of Growth): https://www.lennysnewsletter.com/p/the-new-ai-growth-playbook-for-2026-elena-verna• Elena Verna on how B2B growth is changing, product-led growth, product-led sales, why you should go freemium not trial, what features to make free, and much more: https://www.lennysnewsletter.com/p/elena-verna-on-why-every-company• The ultimate guide to product-led sales | Elena Verna: https://www.lennysnewsletter.com/p/the-ultimate-guide-to-product-led• 10 growth tactics that never work | Elena Verna (Amplitude, Miro, Dropbox, SurveyMonkey): https://www.lennysnewsletter.com/p/10-growth-tactics-that-never-work-elena-verna• Lovable: https://lovable.dev• Lovable + Shopify: https://lovable.dev/shopify• Everyone’s an engineer now: Inside v0’s mission to create a hundred million builders | Guillermo Rauch (founder and CEO of Vercel, creators of v0 and Next.js): https://www.lennysnewsletter.com/p/everyones-an-engineer-now-guillermo-rauch• Mobbin: https://mobbin.com• Dribbble: https://dribbble.com• 21st.dev: https://21st.dev• Lovable base prompt generator: https://chatgpt.com/g/g-67e1da2c9c988191b52b61084438e8ee-lovable-base-prompt• Lovable PRD generator: https://chatgpt.com/g/g-67e1e85fbeac8191a69b95c6d5c42ef6-lovable-prd-generator• Felix Haas’s newsletter: https://designplusai.com• Bauhaus: https://en.wikipedia.org/wiki/Bauhaus• Glassmorphism: https://www.figma.com/community/plugin/1197106608665398190/glassmorphism• UI style guide: http://uistyle.lovable.app• Cloudflare: https://www.cloudflare.com• Ben Tossell on X: https://x.com/bentossell• The rise of Cursor: The $300M ARR AI tool that engineers can’t stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell• Peter Thiel says AI will be ‘worse’ for math nerds than for writers: https://www.businessinsider.com/peter-thiel-ai-worse-for-math-professionals-than-writers-2024-4• Andrej Karpathy on X: https://x.com/karpathy• The 100-person AI lab that became Anthropic and Google’s secret weapon | Edwin Chen (Surge AI): https://www.lennysnewsletter.com/p/surge-ai-edwin-chen• Why experts writing AI evals is creating the fastest-growing companies in history | Brendan Foody (CEO of Mercor): https://www.lennysnewsletter.com/p/experts-writing-ai-evals-brendan-foody• Slumdog Millionaire: https://www.imdb.com/title/tt1010048—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

Dr. Becky Kennedy is a clinical psychologist, the bestselling author of Good Inside, and the founder of a parenting platform used by millions. Known for her practical, psychology-based approach to parenting, Dr. Becky shares how the same principles that help parents raise resilient children can make you a much more effective leader. In this conversation, she breaks down why all human systems—whether families or companies—operate on the same fundamental principles, and how understanding these dynamics can make you more effective in every relationship.We discuss:1. Why repair—not perfection—defines strong leadership2. Why you need to connect before you correct to build cooperation and trust3. The “most generous interpretation” framework for handling difficult behaviors4. How to correctly set boundaries (vs. making requests)5. The power of “I believe you, and I believe in you”6. What it looks like to be a “sturdy” leader—Brought to you by:Merge—Fast, secure integrations for your products and agents: https://merge.dev/lennyMetaview—The AI platform for recruiting: https://metaview.ai/lennyFramer—Builder better websites faster: https://framer.com/lenny—Episode transcript: https://www.lennysnewsletter.com/p/dr-becky-on-the-surprising-overlap—Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0—Where to find Dr. Becky Kennedy:• X: https://x.com/GoodInside• LinkedIn: https://www.linkedin.com/in/drbecky• Instagram: https://www.instagram.com/drbeckyatgoodinside• TikTok: https://www.tiktok.com/@drbeckyatgoodinside• Website: https://www.goodinside.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 Dr. Becky Kennedy(05:14) Connecting parenting and leadership(08:40) The power of repair(11:05) Connecting before correcting(17:45) Good Inside framework at work(22:08) The most generous interpretation (MGI)(25:46) Curiosity over judgment(27:07) Understanding behavior change(31:08) What potty training can teach us about workplace behavior(34:40) Naming your intention(35:41) Sturdy leadership(40:52) How to set boundaries well(46:33) The role of leadership and consensus(50:50) The importance of being “locatable”(52:40) A powerful story of betrayal and realization(57:12) Building resilience over happiness(01:00:34) The power of the phrase “I believe you, and I believe in you.”(01:09:08) The Good Inside community and resources(01:16:22) AI corner(01:19:52) Good Inside’s mission(01:22:26) Lightning round and final thoughts—Referenced:• Shreyas Doshi on pre-mortems, the LNO framework, the three levels of product work, why most execution problems are strategy problems, and ROI vs. opportunity cost thinking: https://www.lennysnewsletter.com/p/episode-3-shreyas-doshi• Radical Candor: From theory to practice with author Kim Scott: https://www.lennysnewsletter.com/p/radical-candor-from-theory-to-practice• From ChatGPT to Instagram to Uber: The quiet architect behind the world’s most popular products | Peter Deng: https://www.lennysnewsletter.com/p/the-quiet-architect-peter-deng• Punch: https://en.wikipedia.org/wiki/Punch_(play)• Figma: https://www.figma.com• Andrew Hogan on LinkedIn: https://www.linkedin.com/in/ahhogan• Replit: https://replit.com• Behind the product: Replit | Amjad Masad (co-founder and CEO): https://www.lennysnewsletter.com/p/behind-the-product-replit-amjad-masad• Lovable: https://lovable.dev• Building Lovable: $10M ARR in 60 days with 15 people | Anton Osika (co-founder and CEO): https://www.lennysnewsletter.com/p/building-lovable-anton-osika• Claude: https://claude.ai• ChatGPT: https://chatgpt.com• Secrets We Keep on Netflix: https://www.netflix.com/title/81697668• K Pop Demon Hunters on Netflix: https://www.netflix.com/title/81498621• Liberty puzzles: https://libertypuzzles.com—Recommended books:• Radical Candor: Be a Kick-Ass Boss Without Losing Your Humanity: https://www.amazon.com/Radical-Candor-Revised-Kick-Ass-Humanity/dp/1250235375• Good Inside: A Practical Guide to Resilient Parenting Prioritizing Connection Over Correction: https://www.amazon.com/Good-Inside-Guide-Becoming-Parent/dp/0063159481• Leave Me Alone!: A Good Inside Story About Deeply Feeling Kids: https://www.amazon.com/Leave-Me-Alone-Inside-Feeling/dp/1250413117• The Power of Moments: Why Certain Experiences Have Extraordinary Impact: https://www.amazon.com/Power-Moments-Certain-Experiences-Extraordinary/dp/1501147765/• The Messy Middle: Finding Your Way Through the Hardest and Most Crucial Part of Any Bold Venture: https://www.amazon.com/Messy-Middle-Finding-Through-Hardest/dp/0735218072• Creativity, Inc.: Overcoming the Unseen Forces That Stand in the Way of True Inspiration: https://www.amazon.com/Creativity-Inc-Expanded-Overcoming-Inspiration/dp/0593594649—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

Marc Andreessen is a founder, investor, and co-founder of Netscape, as well as co-founder of the venture capital firm Andreessen Horowitz (a16z). In this conversation, we dig into why we’re living through a unique and one of the most incredible times in history, and what comes next.We discuss:1. Why AI is arriving at the perfect moment to counter demographic collapse and declining productivity2. How Marc has raised his 10-year-old kid to thrive in an AI-driven world3. What’s actually going to happen with AI and jobs (spoiler: he thinks the panic is “totally off base”)4. The “Mexican standoff” that’s happening between product managers, designers, and engineers5. Why you should still learn to code (even with AI)6. How to develop an “E-shaped” career that combines multiple skills, with AI as a force multiplier7. The career advice he keeps coming back to (“Don’t be fungible”)8. How AI can democratize one-on-one tutoring, potentially transforming education9. His media diet: X and old books, nothing in between—Brought to you by:DX—The developer intelligence platform designed by leading researchersBrex—The banking solution for startupsDatadog—Now home to Eppo, the leading experimentation and feature flagging platform—Episode transcript: https://www.lennysnewsletter.com/p/marc-andreessen-the-real-ai-boom—Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0—Where to find Marc Andreessen:• X: https://x.com/pmarca• Substack: https://pmarca.substack.com• Andreessen Horowitz’s website: https://a16z.com• Andreessen Horowitz’s YouTube channel: https://www.youtube.com/@a16z—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 Marc Andreessen(04:27) The historic moment we’re living in(06:52) The impact of AI on society(11:14) AI’s role in education and parenting(22:15) The future of jobs in an AI-driven world(30:15) Marc's past predictions(35:35) The Mexican standoff of tech roles(39:28) Adapting to changing job tasks(42:15) The shift to scripting languages(44:50) The importance of understanding code(51:37) The value of design in the AI era(53:30) The T-shaped skill strategy(01:02:05) AI’s impact on founders and companies(01:05:58) The concept of one-person billion-dollar companies(01:08:33) Debating AI moats and market dynamics(01:14:39) The rapid evolution of AI models(01:18:05) Indeterminate optimism in venture capital(01:22:17) The concept of AGI and its implications(01:30:00) Marc's media diet(01:36:18) Favorite movies and AI voice technology(01:39:24) Marc's product diet(01:43:16) Closing thoughts and recommendations—Referenced:• Linus Torvalds on LinkedIn: https://www.linkedin.com/in/linustorvalds• The philosopher’s stone: https://en.wikipedia.org/wiki/Philosopher%27s_stone• Alexander the Great: https://en.wikipedia.org/wiki/Alexander_the_Great• Aristotle: https://en.wikipedia.org/wiki/Aristotle• Bloom’s 2 sigma problem: https://en.wikipedia.org/wiki/Bloom%27s_2_sigma_problem• Alpha School: https://alpha.school• In Tech We Trust? A Debate with Peter Thiel and Marc Andreessen: https://a16z.com/in-tech-we-trust-a-debate-with-peter-thiel-and-marc-andreessen• John Woo: https://en.wikipedia.org/wiki/John_Woo• Assembly: https://en.wikipedia.org/wiki/Assembly_language• C programming language: https://en.wikipedia.org/wiki/C_(programming_language)• Python: https://www.python.org• Netscape: https://en.wikipedia.org/wiki/Netscape• Perl: https://www.perl.org• Scott Adams: https://en.wikipedia.org/wiki/Scott_Adams• Larry Summers’s website: https://larrysummers.com• Nano Banana: https://gemini.google/overview/image-generation• Bitcoin: https://bitcoin.org• Ethereum: https://ethereum.org• Satoshi Nakamoto: https://en.wikipedia.org/wiki/Satoshi_Nakamoto• Inside ChatGPT: The fastest-growing product in history | Nick Turley (Head of ChatGPT at OpenAI): https://www.lennysnewsletter.com/p/inside-chatgpt-nick-turley• 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• Inside Google’s AI turnaround: The rise of AI Mode, strategy behind AI Overviews, and their vision for AI-powered search | Robby Stein (VP of Product, Google Search): https://www.lennysnewsletter.com/p/how-google-built-ai-mode-in-under-a-year• DeepSeek: https://www.deepseek.com• Cowork: https://support.claude.com/en/articles/13345190-getting-started-with-cowork• Definite vs. indefinite thinking: Notes from Zero to One by Peter Thiel: https://boxkitemachine.net/posts/zero-to-one-peter-thiel-definite-vs-indefinite-thinking• Henry Ford: https://www.thehenryford.org/explore/stories-of-innovation/visionaries/henry-ford• Lex Fridman Podcast: https://lexfridman.com/podcast• $46B of hard truths from Ben Horowitz: Why founders fail and why you need to run toward fear (a16z co-founder): https://www.lennysnewsletter.com/p/46b-of-hard-truths-from-ben-horowitz• Eddington: https://www.imdb.com/title/tt31176520• Joaquin Phoenix: https://en.wikipedia.org/wiki/Joaquin_Phoenix• Pedro Pascal: https://en.wikipedia.org/wiki/Pedro_Pascal• George Floyd: https://en.wikipedia.org/wiki/George_Floyd• Replit: https://replit.com• Behind the product: Replit | Amjad Masad (co-founder and CEO): https://www.lennysnewsletter.com/p/behind-the-product-replit-amjad-masad• Grok Bad Rudi: https://grok.com/badrudi• Wispr Flow: https://wisprflow.ai• Star Trek: The Next Generation: https://www.imdb.com/title/tt0092455• Star Trek: Starfleet Academy: https://www.imdb.com/title/tt8622160• a16z: The Power Brokers: https://www.notboring.co/p/a16z-the-power-brokers—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Jason Cohen is a four-time founder (including two unicorns, one being WP Engine) and an investor in over 60 startups, and has been sharing his lessons on company building at A Smart Bear for nearly 20 years. In this episode, Jason shares his methodical five-step framework for diagnosing stalled growth—a problem that faces almost every team.We discuss:1. Jason’s five-step framework: logo retention, pricing, NRR, marketing channels, target market2. A small tweak that’ll double response rates on your cancellation surveys3. Why “it’s too expensive” is almost never the real reason customers cancel4. The “elephant curve” of growth5. How repositioning the same product can increase revenue 8x6. When to reconsider if growth is even the right goal for your business—Brought to you by:10Web—Vibe coding platform as an APIStrella—The AI-powered customer research platformBrex—The banking solution for startups—Episode transcript: https://www.lennysnewsletter.com/p/why-your-product-stopped-growing—Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0—Where to find Jason Cohen:• Preorder Jason’s book: https://preorder.hiddenmultipliers.com/• X: https://x.com/asmartbear• LinkedIn: https://www.linkedin.com/in/jasoncohen• Blog: https://longform.asmartbear.com• Website: https://wpengine.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 Jason Cohen(05:19) Jason’s writing journey(08:25) Questions to ask when your product stops growing(18:17) Getting real customer feedback(20:27) Analyzing cancellation reasons(26:54) Onboarding and activation(29:35) Quick summary(35:46) Revisiting pricing strategies(41:46) Positioning strategies(47:52) Why pricing is inseparable from your strategy(52:06) The importance of net revenue retention (NRR)(01:00:25) Asking whether or not this is good for the customer(01:04:34) Leveraging existing customers(01:06:42) Are your acquisition channels saturated? The “elephant curve”(1:09:41) Why all marketing channels eventually decline(01:12:04) Direct vs. indirect marketing channels(1:13:36) Getting creative with new channels(01:19:04) Do you actually need to grow?(01:25:57) Deciding when to quit(01:29:27) Book announcement(01:33:21) AI corner(01:34:35) Contrarian corner(01:37:43) Lightning round and final thoughts—Referenced:• Tyler Cowen’s website: https://tylercowen.com• How to Perform a Customer Churn Analysis (and Why You Should): https://www.groovehq.com/blog/learn-from-customer-churn• Linear: https://linear.app• Jira: https://www.atlassian.com/software/jira• Patrick Campbell’s post on X about pricing: https://x.com/Patticus/status/1702313260547006942• The art and science of pricing | Madhavan Ramanujam (Monetizing Innovation, Simon-Kucher): https://www.lennysnewsletter.com/p/the-art-and-science-of-pricing-madhavan• Pricing your AI product: Lessons from 400+ companies and 50 unicorns | Madhavan Ramanujam: https://www.lennysnewsletter.com/p/pricing-and-scaling-your-ai-product-madhavan-ramanujam• Pricing your SaaS product: https://www.lennysnewsletter.com/p/saas-pricing-strategy• M&A, competition, pricing, and investing | Julia Schottenstein (dbt Labs): https://www.lennysnewsletter.com/p/m-and-a-competition-pricing-and-investing• “Sell the alpha, not the feature”: The enterprise sales playbook for $1M to $10M ARR | Jen Abel: https://www.lennysnewsletter.com/p/the-enterprise-sales-playbook-1m-to-10m-arr• Buffer: https://buffer.com• AG1: https://drinkag1.com• How to find hidden growth opportunities in your product | Albert Cheng (Duolingo, Grammarly, Chess.com): https://www.lennysnewsletter.com/p/how-to-find-hidden-growth-opportunities-albert-cheng• How Duolingo reignited user growth: https://www.lennysnewsletter.com/p/how-duolingo-reignited-user-growth• The Elephant in the room: The myth of exponential hypergrowth: https://longform.asmartbear.com/exponential-growth• HubSpot: https://www.hubspot.com• 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• Adjacency Matrix: How to expand after PMF: https://longform.asmartbear.com/adjacency/• Ecosystem is the next big growth channel: https://www.lennysnewsletter.com/p/ecosystem-is-the-next-big-growth• ChatGPT apps are about to be the next big distribution channel: Here’s how to build one: https://www.lennysnewsletter.com/p/chatgpt-apps-are-about-to-be-the• 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling): https://www.lennysnewsletter.com/p/10-contrarian-leadership-truths• Breaking the rules of growth: Why Shopify bans KPIs, optimizes for churn, prioritizes intuition, and builds toward a 100-year vision | Archie Abrams (VP Product, Head of Growth at Shopify): https://www.lennysnewsletter.com/p/shopifys-growth-archie-abrams• Geoffrey Moore on finding your beachhead, crossing the chasm, and dominating a market: https://www.lennysnewsletter.com/p/geoffrey-moore-on-finding-your-beachhead• ER on Prime Video: https://www.amazon.com/ER-Season-1/dp/B0FWK5WJQ4• The Pitt on Prime Video: https://www.amazon.com/The-Pitt-Season-1/dp/B0DNRR8QWD• Wispr Flow: https://wisprflow.ai• Anker: https://www.anker.com—Recommended books:• Will: https://www.amazon.com/Will-Smith/dp/1984877925• Monetizing Innovation: How Smart Companies Design the Product Around the Price: https://www.amazon.com/Monetizing-Innovation-Companies-Design-Product/dp/1119240867• Hidden Multipliers: Small Things That Accelerate Growth: https://preorder.hiddenmultipliers.com• On Writing Well: The Essential Guide to Mastering Nonfiction Writing and Effective Communication: https://www.amazon.com/Writing-Well-Classic-Guide-Nonfiction/dp/0060891548• Crossing the Chasm, 3rd Edition: The Updated Version of the Insightful Guide on Bringing Cutting-Edge Products to the Mainstream: https://www.amazon.com/Crossing-Chasm-3rd-Disruptive-Mainstream/dp/0062292986—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

Zevi Arnovitz is a product manager at Meta with no technical background who has figured out how to build and ship real products using AI. His engineering team at Meta asks him to teach them how he does what he does. In this episode, Zevi breaks down his complete AI workflow that allows non-technical people to build sophisticated products with Cursor.We discuss:1. The complete AI workflow that lets non-technical people build real products in Cursor2. How to use multiple AI models for different tasks (Claude for planning, Gemini for UI)3. Using slash commands to automate prompts4. Zevi’s “peer review” technique, which uses different AI models to review each other’s code5. Why this might be the best time to be a junior in tech, despite the challenging job market6. How Zevi used AI to prepare for his Meta PM interviews—Brought to you by:10Web—Vibe coding platform as an APIDX—The developer intelligence platform designed by leading researchersFramer—Build better websites faster—Zevi's Slash Command Bank for Claude: ⁠https://zeviarnovitz.com/⁠—Episode transcript: https://www.lennysnewsletter.com/p/the-non-technical-pms-guide-to-building-with-cursor—Archive of all Lenny's Podcast transcripts:https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0—Where to find Zevi Arnovitz• X: https://x.com/ArnovitzZevi• LinkedIn: https://www.linkedin.com/in/zev-arnovitz• Website: https://zeviarnovitz.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 Zevi Arnovitz(04:48) Zevi’s background and journey into AI(07:41) Overview of Zevi’s AI workflow(14:41) Screenshare: Exploring Zevi’s workflow in detail(17:18) Building a feature live: StudyMate app(30:52) Executing the plan with Cursor(38:32) Using multiple AI models for code review(40:40) Personifying AI models(43:37) Peer review process(45:40) The importance of postmortems(51:05) Integrating AI in large companies(53:42) How AI has impacted the PM role(57:02) How to improve AI outputs(58:15) AI-assisted job interviews(01:02:57) Failure corner(01:06:20) Lightning round and final thoughts—Referenced:• Becoming a super IC: Lessons from 12 years as a PM individual contributor | Tal Raviv (Product Lead at Riverside): https://www.lennysnewsletter.com/p/the-super-ic-pm-tal-raviv• Wix: https://www.wix.com• Building AI Apps: From Idea to Viral in 30 Days: https://www.youtube.com/watch?v=j2w4y7pDi8w• Riley Brown on YouTube: https://www.youtube.com/channel/UCMcoud_ZW7cfxeIugBflSBw• Greg Isenberg on YouTube: https://www.youtube.com/@GregIsenberg• Bolt: https://bolt.new• Inside Bolt: From near-death to ~$40m ARR in 5 months—one of the fastest-growing products in history | Eric Simons (founder and CEO of StackBlitz): https://www.lennysnewsletter.com/p/inside-bolt-eric-simons• Lovable: https://lovable.dev• 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• StudyMate: https://studymate.live• Dibur2text: https://dibur2text.app• Claude: https://claude.ai• Everyone should be using Claude Code more: https://www.lennysnewsletter.com/p/everyone-should-be-using-claude-code• Bun: https://bun.com• Zustand: https://zustand.docs.pmnd.rs/getting-started/introduction• Cursor: https://cursor.com• The rise of Cursor: The $300M ARR AI tool that engineers can’t stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell• Wispr Flow: https://wisprflow.ai• Linear: https://linear.app• Linear’s secret to building beloved B2B products | Nan Yu (Head of Product): https://www.lennysnewsletter.com/p/linears-secret-to-building-beloved-b2b-products-nan-yu• Cursor Composer: https://cursor.com/blog/composer• Replit: https://replit.com• Behind the product: Replit | Amjad Masad (co-founder and CEO): https://www.lennysnewsletter.com/p/behind-the-product-replit-amjad-masad• Base44: https://base44.com• Solo founder, $80M exit, 6 months: The Base44 bootstrapped startup success story | Maor Shlomo: https://www.lennysnewsletter.com/p/the-base44-bootstrapped-startup-success-story-maor-shlomo• v0: https://v0.app• Everyone’s an engineer now: Inside v0’s mission to create a hundred million builders | Guillermo Rauch (founder & CEO of Vercel, creators of v0 and Next.js): https://www.lennysnewsletter.com/p/everyones-an-engineer-now-guillermo-rauch• Cursor Browser mode: https://cursor.com/docs/agent/browser• Google Antigravity: https://antigravity.google• Grok: https://grok.com• Zapier: https://zapier.com• Airtable: https://www.airtable.com• Build Your Personal PM Productivity System & AI Copilot: https://maven.com/tal-raviv/product-manager-productivity-system• The definitive guide to mastering analytical thinking interviews: https://www.lennysnewsletter.com/p/the-definitive-guide-to-mastering-f81• AI tools are overdelivering: results from our large-scale AI productivity survey: https://www.lennysnewsletter.com/p/ai-tools-are-overdelivering-results-c08• Yaara Asaf on LinkedIn: https://www.linkedin.com/in/yaarasaf• The Pitt on Prime Video: https://www.amazon.com/The-Pitt-Season-1/dp/B0DNRR8QWD• Severance on AppleTV+: https://tv.apple.com/us/show/severance/umc.cmc.1srk2goyh2q2zdxcx605w8vtx• Loom: https://www.loom.com• Cap: https://cap.so• Supercut: https://supercut.ai...References continued at: https://www.lennysnewsletter.com/p/the-non-technical-pms-guide-to-building-with-cursor—Recommended books:• The Fountainhead: https://www.amazon.com/Fountainhead-Ayn-Rand/dp/0451191153• Shoe Dog: A Memoir by the Creator of Nike: https://www.amazon.com/Shoe-Dog-Memoir-Creator-Nike/dp/1501135910• Mindset: The New Psychology of Success: https://www.amazon.com/Mindset-Psychology-Carol-S-Dweck/dp/0345472322—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

Sam Lessin is a partner at Slow Ventures, a former VP of Product at Facebook, and a two-time founder who’s now teaching etiquette to Silicon Valley’s founders. In this unconventional episode, Sam explains why proper etiquette has become a vital skill for founders in 2026—especially as technology becomes more central to society and trust becomes harder to build. His etiquette book and courses have become surprisingly popular, teaching founders how to “show up in a room with a low heart rate” and quickly build trust.We discuss:1. Why etiquette matters2. Sam’s framework for showing up confidently, with a low heart rate, in any room3. How to navigate introductions, small talk, meetings, and meals like a pro4. Simple hacks for remembering names and handling awkward social situations5. 30+ specific etiquette tips—Brought to you by:10Web—Vibe-coding platform as an APIDX—The developer intelligence platform designed by leading researchersWorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs—Episode transcript: https://www.lennysnewsletter.com/p/silicon-valleys-missing-etiquette-playbook—Archive of all Lenny's Podcast transcripts:https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0—Where to find Sam Lessin:• X: https://x.com/lessin• LinkedIn: https://www.linkedin.com/in/wlessin• Website: https://www.wlessin.com• Podcast: https://moreorlesspod.com• Lettermeme: https://lettermeme.com/lessin—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) Sam’s background(04:18) The role of etiquette in business success(09:30) Introductions and entering a room(16:20) Engaging conversations and building relationships(23:55) Hygiene and dress code essentials(33:42) Dining etiquette(37:15) Tipping etiquette(41:36) The “B&D trick”(43:05) Humor in social settings(45:18) Self-deprecating humor(47:42) Winding down conversations(49:20) Scheduling etiquette(55:23) Communication and email etiquette(01:02:28) Meeting etiquette tips(01:04:03) Virtual meeting best practices(01:05:15) The importance of cleaning up after yourself(01:05:58) Exiting and follow-up etiquette(01:07:24) Final thoughts(01:09:20) AI corner(01:11:13) Contrarian corner(01:16:25) Lightning round—Referenced:• Y Combinator: https://www.ycombinator.com• Kleiner Perkins: https://www.kleinerperkins.com• “Lose Yourself” by Eminem on Spotify: https://open.spotify.com/track/7MJQ9Nfxzh8LPZ9e9u68Fq• Alison Gopnik on Childhood Learning, AI as a Cultural Technology, and Rethinking Nature vs. Nurture: https://conversationswithtyler.com/episodes/alison-gopnik• Garry Tan on LinkedIn: https://www.linkedin.com/in/garrytan• Bain & Company: https://www.bain.com• Evernote: https://evernote.com• Calendly: https://calendly.com• Morning Brew: https://www.morningbrew.com• Cursor: https://cursor.com• The rise of Cursor: The $300M ARR AI tool that engineers can’t stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell• DigitalOcean: https://www.digitalocean.com• Cloudflare: https://www.cloudflare.com• SpaceX: https://www.spacex.com• Marc Andreessen on X: https://x.com/pmarca• Landman on Prime Video: https://www.amazon.com/Landman-Season-1/dp/B0D4D8RTMD• Dave Morin on X: https://x.com/davemorin—Recommended books:• Modern Etiquette in Technology, Finance, Society, and at Home: A Slow Ventures Handbook: https://www.amazon.com/Modern-Etiquette-Technology-Finance-Society-ebook/dp/B0G4HSKSY5• Life, the Universe and Everything: https://www.amazon.com/Universe-Everything-Hitchhikers-Guide-Galaxy-ebook/dp/B001ODEQ7A• The Ancient City: A Study on the Religion, Laws, and Institutions of Greece and Rome: https://www.amazon.com/Ancient-City-Religion-Institutions-Greece/dp/0801823048• Man’s Search for Meaning: https://www.amazon.com/Mans-Search-Meaning-Viktor-Frankl-ebook/dp/B009U9S6FI• Area 51: An Uncensored History of America’s Top Secret Military Base: https://www.amazon.com/Area-51-Uncensored-Americas-Military-ebook/dp/B004THU68Q• The Lessons of History: https://www.amazon.com/Lessons-History-Will-Durant/dp/143914995X• The Fish That Ate the Whale: The Life and Times of America’s Banana King: https://www.amazon.com/Fish-That-Ate-Whale-Americas/dp/1250033314• The Last Kings of Shanghai: The Rival Jewish Dynasties That Helped Create Modern China: https://www.amazon.com/Last-Kings-Shanghai-Jewish-Dynasties/dp/0735224439—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

Aishwarya Naresh Reganti and Kiriti Badam have helped build and launch more than 50 enterprise AI products across companies like OpenAI, Google, Amazon, and Databricks. Based on these experiences, they’ve developed a small set of best practices for building and scaling successful AI products. The goal of this conversation is to save you and your team a lot of pain and suffering.We discuss:1. Two key ways AI products differ from traditional software, and why that fundamentally changes how they should be built2. Common patterns and anti-patterns in companies that build strong AI products versus those that struggle3. A framework they developed from real-world experience to iteratively build AI products that create a flywheel of improvement4. Why obsessing about customer trust and reliability is an underrated driver of successful AI products5. Why evals aren’t a cure-all, and the most common misconceptions people have about them6. The skills that matter most for builders in the AI era—Brought to you by:Merge—The fastest way to ship 220+ integrations: https://merge.dev/lennyStrella—The AI-powered customer research platform: https://strella.io/lennyBrex—The banking solution for startups: https://www.brex.com/product/business-account?ref_code=bmk_dp_brand1H25_ln_new_fs—Transcript: https://www.lennysnewsletter.com/p/what-openai-and-google-engineers-learned—My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/183007822/referenced—Get 15% off Aishwarya and Kiriti’s Maven course, Building Agentic AI Applications with a Problem-First Approach, using this link: https://bit.ly/3V5XJFp—Where to find Aishwarya Naresh Reganti:• LinkedIn: https://www.linkedin.com/in/areganti• GitHub: https://github.com/aishwaryanr/awesome-generative-ai-guide• X: https://x.com/aish_reganti—Where to find Kiriti Badam:• LinkedIn: https://www.linkedin.com/in/sai-kiriti-badam• X: https://x.com/kiritibadam—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 Aishwarya and Kiriti(05:03) Challenges in AI product development(07:36) Key differences between AI and traditional software(13:19) Building AI products: start small and scale(15:23) The importance of human control in AI systems(22:38) Avoiding prompt injection and jailbreaking(25:18) Patterns for successful AI product development(33:20) The debate on evals and production monitoring(41:27) Codex team’s approach to evals and customer feedback(45:41) Continuous calibration, continuous development (CC/CD) framework(58:07) Emerging patterns and calibration(01:01:24) Overhyped and under-hyped AI concepts(01:05:17) The future of AI(01:08:41) Skills and best practices for building AI products(01:14:04) Lightning round and final thoughts—Referenced:• LevelUp Labs: https://levelup-labs.ai/• Why your AI product needs a different development lifecycle: https://www.lennysnewsletter.com/p/why-your-ai-product-needs-a-different• Booking.com: https://www.booking.com• Research paper on agents in production (by Matei Zaharia’s lab): https://arxiv.org/pdf/2512.04123• Matei Zaharia’s research on Google Scholar: https://scholar.google.com/citations?user=I1EvjZsAAAAJ&hl=en• The coming AI security crisis (and what to do about it) | Sander Schulhoff: https://www.lennysnewsletter.com/p/the-coming-ai-security-crisis• Gajen Kandiah on LinkedIn: https://www.linkedin.com/in/gajenkandiah• Rackspace: https://www.rackspace.com• The AI-native startup: 5 products, 7-figure revenue, 100% AI-written code | Dan Shipper (co-founder/CEO of Every): https://www.lennysnewsletter.com/p/inside-every-dan-shipper• Semantic Diffusion: https://martinfowler.com/bliki/SemanticDiffusion.html• LMArena: https://lmarena.ai• Artificial Analysis: https://artificialanalysis.ai/leaderboards/providers• Why humans are AI’s biggest bottleneck (and what’s coming in 2026) | Alexander Embiricos (OpenAI Codex Product Lead): https://www.lennysnewsletter.com/p/why-humans-are-ais-biggest-bottleneck• Airline held liable for its chatbot giving passenger bad advice—what this means for travellers: https://www.bbc.com/travel/article/20240222-air-canada-chatbot-misinformation-what-travellers-should-know• Demis Hassabis on LinkedIn: https://www.linkedin.com/in/demishassabis• We replaced our sales team with 20 AI agents—here’s what happened | Jason Lemkin (SaaStr): https://www.lennysnewsletter.com/p/we-replaced-our-sales-team-with-20-ai-agents• Socrates’s quote: https://en.wikipedia.org/wiki/The_unexamined_life_is_not_worth_living• Noah Smith’s newsletter: https://www.noahpinion.blog• Silicon Valley on HBO Max: https://www.hbomax.com/shows/silicon-valley/b4583939-e39f-4b5c-822d-5b6cc186172d• Clair Obscur: Expedition 33: https://store.steampowered.com/app/1903340/Clair_Obscur_Expedition_33/• Wisprflow: https://wisprflow.ai• Raycast: https://www.raycast.com• Steve Jobs’s quote: https://www.goodreads.com/quotes/463176-you-can-t-connect-the-dots-looking-forward-you-can-only—Recommended books:•  When Breath Becomes Air: https://www.amazon.com/When-Breath-Becomes-Paul-Kalanithi/dp/081298840X• The Three-Body Problem: https://www.amazon.com/Three-Body-Problem-Cixin-Liu/dp/0765382032• A Fire Upon the Deep: https://www.amazon.com/Fire-Upon-Deep-Zones-Thought/dp/0812515285—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

Molly Graham has worked for some of tech’s most effective leaders, including Mark Zuckerberg, Sheryl Sandberg, Chamath Palihapitiya, and Bret Taylor. Today she leads Glue Club, a community for leaders navigating rapid scale, growth, and change. She’s best known for her “Give away your Legos” framework and her collection of practical mental models for leading through hypergrowth.We discuss:1. “Give away your Legos”: a framework for scaling yourself as a leader2. “J-curves vs. stairs”: the two paths of career growth, and why you should pick the scarier path3. “The waterline model” for diagnosing team problems (and why you should “snorkel before you scuba”)4. Six rules for creating effective goals (and aligning everyone around them)5. Rules of thumb for leading through rapid scale and change6. Her biggest leadership lessons from Mark Zuckerberg, Sergey Brin, Larry Page, Sheryl Sandberg, and Bret Taylor—Brought to you by:DX—The developer intelligence platform designed by leading researchersBrex—The banking solution for startupsGoFundMe Giving Funds—Make helping a habit—Transcript: https://www.lennysnewsletter.com/p/the-high-growth-handbook-molly-graham—My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/182877855/my-biggest-takeaways-from-this-conversation—Where to find Molly Graham:• X: https://x.com/molly_g• LinkedIn: https://www.linkedin.com/in/mograham• Substack: https://mollyg.substack.com• Website: https://glueclub.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 Molly Graham(04:28) Molly’s background at Google, Facebook, Quip, and CZI(11:29) The “Give away your Legos” framework(16:44) Managing your inner monster(19:49) When not to give away your Legos(21:28) Embracing a long career(23:25) The J-curve vs. stairs approach to career growth(32:00) The gift of knowing yourself(34:28) Learning to be a professional idiot(38:30) The waterline model: snorkel before you scuba(47:16) Six rules for creating strong alignment around goals(57:15) Rules of thumb for leading through rapid scale(01:07:49) Investing in high performers vs. low performers(01:10:54) Lessons from Zuckerberg, Sandberg, and Bret Taylor(1:21:15) Pivoting from ambition to purpose(1:26:32) Finding stability in instability(01:29:44) Final thoughts—Referenced:• Making an impact through authenticity and curiosity | Ami Vora (CPO at Faire, ex-WhatsApp, FB, IG): https://www.lennysnewsletter.com/p/authenticity-and-curiosity-ami-vora• Sheryl Sandberg on LinkedIn: https://www.linkedin.com/in/sheryl-sandberg-5126652• Elliot Schrage on LinkedIn: https://www.linkedin.com/in/elliotschrage• Quip: https://quip.com• 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• Chan Zuckerberg Initiative: https://chanzuckerberg.com• 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling): https://www.lennysnewsletter.com/p/10-contrarian-leadership-truths• ‘Give Away Your Legos’ and Other Commandments for Scaling Startups: https://review.firstround.com/give-away-your-legos-and-other-commandments-for-scaling-startups• The Muppets: https://muppets.disney.com• Sara Caldwell on LinkedIn: https://www.linkedin.com/in/saramcaldwell• J-Curves vs. Stairs: Two Approaches to Career Growth: https://mollyg.substack.com/p/j-curve• Forget the corporate ladder—winners take risks: https://www.ted.com/talks/molly_graham_forget_the_corporate_ladder_winners_take_risks• Chamath Palihapitiya on LinkedIn: https://www.linkedin.com/in/chamath• Lori Goler on LinkedIn: https://www.linkedin.com/in/lori-goler-6b96921• Joseph Campbell’s quote: https://www.goodreads.com/quotes/192665-the-cave-you-fear-to-enter-holds-the-treasure-you• Zevi Arnovitz on LinkedIn: https://www.linkedin.com/in/zev-arnovitz• Peopling 101: The Waterline Model: https://christinehaskell.com/blog/peopling-101-the-waterline-model• Introduction to NVC: https://www.cnvc.org/learn/what-is-nvc• I hate OKRs... and other thoughts about goal setting: https://mollyg.substack.com/p/i-hate-okrs-and-other-thoughts-about• Lessons from scaling Stripe | Claire Hughes Johnson (former COO of Stripe): https://www.lennysnewsletter.com/p/lessons-from-scaling-stripe-tactics• James Clear’s quote: https://www.goodreads.com/quotes/9614600-problem-1-winners-and-losers-have-the-same-goals• Founder mode: https://paulgraham.com/foundermode.html• Stripe: https://stripe.com• Patrick Collison on X: https://www.linkedin.com/in/patrickcollison• John Collison on X: https://x.com/collision• Seth Godin’s best tactics for building remarkable products, strategies, brands and more: https://www.lennysnewsletter.com/p/seth-godins-tactics-for-building-remarkable-products• Eric Antonow on LinkedIn: https://www.linkedin.com/in/antonow—Recommended books:• The Artist’s Way: https://www.amazon.com/Artists-Way-25th-Anniversary/dp/0143129252• Scaling People: Tactics for Management and Company Building: https://www.amazon.com/Scaling-People-Tactics-Management-Building/dp/1953953212• Atomic Habits: An Easy & Proven Way to Build Good Habits & Break Bad Ones: https://www.amazon.com/Atomic-Habits-Proven-Build-Break/dp/0735211299—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Jason Lemkin is the founder of SaaStr, the world’s largest community for software founders, and a veteran SaaS investor who has deployed over $200 million into B2B startups. After his last salesperson quit, Jason made a radical decision: replace his entire go-to-market team with AI agents. What started as an experiment has transformed into a new operating model, where 20 AI agents managed by just 1.2 humans now do the work previously handled by a team of 10 SDRs and AEs. In this conversation, Jason shares his hands-on experience implementing AI to run his sales org, including what works, what doesn’t, and how the GTM landscape is quickly being transformed.We discuss:1. How AI is fundamentally changing the sales function2. Why most SDRs and BDRs will be “extinct” within a year3. What Jason is observing across his portfolio about AI adoption in GTM4. How to become “hyper-employable” in the age of AI5. The specific AI tools and tactics he’s using that have been working best6. Practical frameworks for integrating AI into your sales motion without losing what works7. Jason’s 2026 predictions on where SaaS and GTM are heading next—Brought to you by:DX—The developer intelligence platform designed by leading researchersVercel—Your collaborative AI assistant to design, iterate, and scale full-stack applications for the webDatadog—Now home to Eppo, the leading experimentation and feature flagging platform—Transcript: https://www.lennysnewsletter.com/p/we-replaced-our-sales-team-with-20-ai-agents—My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/182902716/my-biggest-takeaways-from-this-conversation—Where to find Jason Lemkin:• X: https://x.com/jasonlk• LinkedIn: https://www.linkedin.com/in/jasonmlemkin• Website: https://www.saastr.com• Substack: https://substack.com/@cloud—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Jason Lemkin(04:36) What SaaStr does(07:13) AI’s impact on sales teams(10:11) How SaaStr's AI agents work and their performance(14:18) How go-to-market is changing in the AI era(19:19) The future of SDRs, BDRs, and AEs in sales(22:03) Why leadership roles are safe(23:43) How to be in the 20% who thrive in the AI sales future(28:40) Why you shouldn't build your own AI tools(30:10) Specific AI agents and their applications(36:40) Challenges and learnings in AI deployment(42:11) Making AI-generated emails good (not just acceptable)(47:31) When humans still beat AI in sales(52:39) An overview of SaaStr's org(53:50) The role of human oversight in AI operations(58:37) Advice for salespeople and founders in the AI era(01:05:40) Forward-deployed engineers(01:08:08) What's changing and what's staying the same in sales(01:16:21) Why AI is creating more work, not less(01:19:32) Why Jason says these are magical times(01:25:25) The "incognito mode test" for finding AI opportunities(01:27:19) The impact of AI on jobs(01:30:18) Lightning round and final thoughts—Referenced:• Building a world-class sales org | Jason Lemkin (SaaStr): https://www.lennysnewsletter.com/p/building-a-world-class-sales-org• SaaStr Annual: https://www.saastrannual.com• Delphi: https://www.delphi.ai/saastr/talk• Amelia Lerutte on LinkedIn: https://www.linkedin.com/in/amelialerutte/• Vercel: https://vercel.com• What world-class GTM looks like in 2026 | Jeanne DeWitt Grosser (Vercel, Stripe, Google): https://www.lennysnewsletter.com/p/what-the-best-gtm-teams-do-differently• Everyone’s an engineer now: Inside v0’s mission to create a hundred million builders | Guillermo Rauch (founder and CEO of Vercel, creators of v0 and Next.js): https://www.lennysnewsletter.com/p/everyones-an-engineer-now-guillermo-rauch• Replit: https://replit.com• Behind the product: Replit | Amjad Masad (co-founder and CEO): https://www.lennysnewsletter.com/p/behind-the-product-replit-amjad-masad• ElevenLabs: https://elevenlabs.io• The exact AI playbook (using MCPs, custom GPTs, Granola) that saved ElevenLabs $100k+ and helps them ship daily | Luke Harries (Head of Growth): https://www.lennysnewsletter.com/p/the-ai-marketing-stack• Bolt: https://bolt.new• Lovable: https://lovable.dev• Harvey: https://www.harvey.ai• Samsara: https://www.samsara.com/products/platform/ai-samsara-intelligence• UiPath: https://www.uipath.com• Denise Dresser on LinkedIn: https://www.linkedin.com/in/denisedresser• Agentforce: https://www.salesforce.com/form/agentforce• SaaStr’s AI Agent Playbook: https://saastr.ai/agents• Brian Halligan on LinkedIn: https://www.linkedin.com/in/brianhalligan• Brian Halligan’s AI: https://www.delphi.ai/minds/bhalligan• Sierra: https://sierra.ai• Fin: https://fin.ai• Deccan: https://www.deccan.ai• Artisan: https://www.artisan.co• Qualified: https://www.qualified.com• Claude: https://claude.ai• HubSpot: https://www.hubspot.com• Gamma: https://gamma.app• Sam Blond on LinkedIn: https://www.linkedin.com/in/sam-blond-791026b• Brex: https://www.brex.com• Outreach: https://www.outreach.io• Gong: https://www.gong.io• Salesloft: https://www.salesloft.com• Mixmax: https://www.mixmax.com• “Sell the alpha, not the feature”: The enterprise sales playbook for $1M to $10M ARR | Jen Abel: https://www.lennysnewsletter.com/p/the-enterprise-sales-playbook-1m-to-10m-arr• Clay: https://www.clay.com• Owner: https://www.owner.com• Momentum: https://www.momentum.io• Attention: https://www.attention.com• Granola: https://www.granola.ai• Behind the founder: Marc Benioff: https://www.lennysnewsletter.com/p/behind-the-founder-marc-benioff• Palantir: https://www.palantir.com• Databricks: https://www.databricks.com• Garry Tan on LinkedIn: https://www.linkedin.com/in/garrytan• Rippling: https://www.rippling.com• Cursor: https://cursor.com• The rise of Cursor: The $300M ARR AI tool that engineers can’t stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell• The new AI growth playbook for 2026: How Lovable hit $200M ARR in one year | Elena Verna (Head of Growth): https://www.lennysnewsletter.com/p/the-new-ai-growth-playbook-for-2026-elena-verna• Pluribus on AppleTV+: https://tv.apple.com/us/show/pluribus/umc.cmc.37axgovs2yozlyh3c2cmwzlza• Sora: https://openai.com/sora• Reve: https://app.reve.com• Everything That Breaks on the Way to $1B ARR, with Mailchimp Co-Founder Ben Chestnut: https://www.saastr.com/everything-that-breaks-on-the-way-to-1b-arr-with-mailchimp-co-founder-ben-chestnut/• The Revenue Playbook: Rippling’s Top 3 Growth Tactics at Scale, with Rippling CRO Matt Plank: https://www.youtube.com/watch?v=h3eYtzBpjRw• 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling): https://www.lennysnewsletter.com/p/10-contrarian-leadership-truths—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Matt MacInnis is the chief product officer and former longtime COO at Rippling, a unified workforce management platform valued at over $16 billion.We discuss:1. Why “extraordinary results demand extraordinary efforts”2. Why you should deliberately understaff projects, and how to know when you’ve gone too far3. Matt’s transition from COO to CPO and what surprised him about leading product4. The “high alpha, low beta” framework for evaluating people, processes, and products5. When founders should quit their startups (hint: much earlier than VCs want you to)6. How to fight entropy in your organization through relentless energy and intensity—Brought to you by:Google Gemini—Your everyday AI assistant: https://ai.dev/Datadog—Now home to Eppo, the leading experimentation and feature flagging platform: https://www.datadoghq.com/lennyGoFundMe Giving Funds—Make year-end giving easy: http://gofundme.com/lenny—Transcript: https://www.lennysnewsletter.com/p/10-contrarian-leadership-truths—My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/181916584/my-biggest-takeaways-from-this-conversation—Where to find Matt MacInnis:• X: https://x.com/stanine• LinkedIn: https://www.linkedin.com/in/macinnis• Email: macinnis@rippling.com—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Matt MacInnis and Rippling(04:38) The importance of extraordinary efforts(08:37) The challenges and rewards of relentless effort(10:11) Your job as a leader is to preserve intensity(12:39) You learn far more from success than failure(16:34) Transitioning to chief product officer(19:54) Fixing product management at Rippling(25:27) The “high alpha, low beta” framework(28:55) The PQL framework(35:16) Hiring frameworks and team dynamics(36:52) A helpful interview tactic(40:00) Leading as a COO vs. a CPO(42:34) The reality of product-market fit(46:38) The problem with venture capital(49:29) When founders should quit their startups(41:48) The immutable market(54:13) Lessons from Notion’s success(57:43) Investment strategies and narrative violations(01:00:42) The power of compounding, power law, and entropy(01:07:02) Maintaining intensity and fighting entropy(01:11:33) The importance of feedback and escalations(01:14:31) Rippling’s vision and success(01:17:48) AI’s impact on SaaS and business software(01:23:42) AI corner(01:26:23) Final thoughts and lightning round—Referenced:• Rippling: https://www.rippling.com• Sunil Raman on LinkedIn: https://www.linkedin.com/in/sunilraman• Dan Gill on LinkedIn: https://www.linkedin.com/in/dangill• Carvana: https://www.carvana.com• Brian Chesky’s new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach• Parker Conrad on LinkedIn: https://www.linkedin.com/in/parkerconrad• Inkling: https://www.inkling.com• Akshay Kothari on LinkedIn: https://www.linkedin.com/in/akothari• Notion: https://www.notion.com• Conway’s law: https://en.wikipedia.org/wiki/Conway%27s_law• Seeking Alpha: https://seekingalpha.com• Dennis Rodman’s website: https://dennisrodman.com• Dancing pickle emoji: https://slackmojis.com/emojis/456-dancing_pickle• Pickle Rick: https://en.wikipedia.org/wiki/Pickle_Rick• SPOTAK: The Six Traits I Look for When I’m Hiring: https://finance.yahoo.com/news/spotak-six-traits-look-m-181335267.html• Geoff Lewis on LinkedIn: https://www.linkedin.com/in/geofflewis1• Zenefits: https://en.wikipedia.org/wiki/TriNet_Zenefits• New banking records prove Deel paid thief who stole trade secrets from Rippling: https://www.rippling.com/blog/new-banking-records-prove-deel-paid-thief-who-stole-trade-secrets-from-rippling• Workday: https://www.workday.com• Matic robots: https://maticrobots.com• Wall-E: https://www.imdb.com/title/tt0910970• Conviction: https://www.conviction.com• Mike Vernal on X: https://x.com/mvernal• Sarah Guo on X: https://x.com/saranormous• No Priors: https://linktr.ee/nopriors• Gemini: https://gemini.google.com• ChatGPT: https://chatgpt.com• Claude: https://claude.ai• Bryan Schreier on LinkedIn: https://www.linkedin.com/in/bryanschreier• Heated Rivalry on HBO Max: https://www.hbomax.com/shows/heated-rivalry/50cd4e99-04ee-427b-a3b4-da721ed05d9c• Fellow coffee maker: https://fellowproducts.com/products/aiden-precision-coffee-maker—Recommended books:• Pale Blue Dot: A Vision of the Human Future in Space: https://www.amazon.com/Pale-Blue-Dot-Vision-Future/dp/0345376595• Conscious Business: How to Build Value Through Values: https://www.amazon.com/Conscious-Business-Build-through-Values/dp/1622032020• Thinking in Systems: https://www.amazon.com/Thinking-Systems-Donella-H-Meadows/dp/1603580557• The Effective Executive: The Definitive Guide to Getting the Right Things Done: https://www.amazon.com/Effective-Executive-Definitive-Harperbusiness-Essentials/dp/0060833459—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

Sander Schulhoff is an AI researcher specializing in AI security, prompt injection, and red teaming. He wrote the first comprehensive guide on prompt engineering and ran the first-ever prompt injection competition, working with top AI labs and companies. His dataset is now used by Fortune 500 companies to benchmark their AI systems security, he’s spent more time than anyone alive studying how attackers break AI systems, and what he’s found isn’t reassuring: the guardrails companies are buying don’t actually work, and we’ve been lucky we haven’t seen more harm so far, only because AI agents aren’t capable enough yet to do real damage.We discuss:1. The difference between jailbreaking and prompt injection attacks on AI systems2. Why AI guardrails don’t work3. Why we haven’t seen major AI security incidents yet (but soon will)4. Why AI browser agents are vulnerable to hidden attacks embedded in webpages5. The practical steps organizations should take instead of buying ineffective security tools6. Why solving this requires merging classical cybersecurity expertise with AI knowledge—Brought to you by:Datadog—Now home to Eppo, the leading experimentation and feature flagging platform: https://www.datadoghq.com/lennyMetronome—Monetization infrastructure for modern software companies: https://metronome.com/GoFundMe Giving Funds—Make year-end giving easy: http://gofundme.com/lenny—Transcript: https://www.lennysnewsletter.com/p/the-coming-ai-security-crisis—My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/181089452/my-biggest-takeaways-from-this-conversation—Where to find Sander Schulhoff:• X: https://x.com/sanderschulhoff• LinkedIn: https://www.linkedin.com/in/sander-schulhoff• Website: https://sanderschulhoff.com• AI Red Teaming and AI Security Masterclass on Maven: https://bit.ly/44lLSbC—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Sander Schulhoff and AI security(05:14) Understanding AI vulnerabilities(11:42) Real-world examples of AI security breaches(17:55) The impact of intelligent agents(19:44) The rise of AI security solutions(21:09) Red teaming and guardrails(23:44) Adversarial robustness(27:52) Why guardrails fail(38:22) The lack of resources addressing this problem(44:44) Practical advice for addressing AI security(55:49) Why you shouldn’t spend your time on guardrails(59:06) Prompt injection and agentic systems(01:09:15) Education and awareness in AI security(01:11:47) Challenges and future directions in AI security(01:17:52) Companies that are doing this well(01:21:57) Final thoughts and recommendations—Referenced:• AI prompt engineering in 2025: What works and what doesn’t | Sander Schulhoff (Learn Prompting, HackAPrompt): https://www.lennysnewsletter.com/p/ai-prompt-engineering-in-2025-sander-schulhoff• The AI Security Industry is Bullshit: https://sanderschulhoff.substack.com/p/the-ai-security-industry-is-bullshit• The Prompt Report: Insights from the Most Comprehensive Study of Prompting Ever Done: https://learnprompting.org/blog/the_prompt_report?srsltid=AfmBOoo7CRNNCtavzhyLbCMxc0LDmkSUakJ4P8XBaITbE6GXL1i2SvA0• OpenAI: https://openai.com• Scale: https://scale.com• Hugging Face: https://huggingface.co• Ignore This Title and HackAPrompt: Exposing Systemic Vulnerabilities of LLMs through a Global Scale Prompt Hacking Competition: https://www.semanticscholar.org/paper/Ignore-This-Title-and-HackAPrompt%3A-Exposing-of-LLMs-Schulhoff-Pinto/f3de6ea08e2464190673c0ec8f78e5ec1cd08642• Simon Willison’s Weblog: https://simonwillison.net• ServiceNow: https://www.servicenow.com• ServiceNow AI Agents Can Be Tricked Into Acting Against Each Other via Second-Order Prompts: https://thehackernews.com/2025/11/servicenow-ai-agents-can-be-tricked.html• Alex Komoroske on X: https://x.com/komorama• Twitter pranksters derail GPT-3 bot with newly discovered “prompt injection” hack: https://arstechnica.com/information-technology/2022/09/twitter-pranksters-derail-gpt-3-bot-with-newly-discovered-prompt-injection-hack• MathGPT: https://math-gpt.org• 2025 Las Vegas Cybertruck explosion: https://en.wikipedia.org/wiki/2025_Las_Vegas_Cybertruck_explosion• Disrupting the first reported AI-orchestrated cyber espionage campaign: https://www.anthropic.com/news/disrupting-AI-espionage• Thinking like a gardener not a builder, organizing teams like slime mold, the adjacent possible, and other unconventional product advice | Alex Komoroske (Stripe, Google): https://www.lennysnewsletter.com/p/unconventional-product-advice-alex-komoroske• Prompt Optimization and Evaluation for LLM Automated Red Teaming: https://arxiv.org/abs/2507.22133• MATS Research: https://substack.com/@matsresearch• CBRN: https://en.wikipedia.org/wiki/CBRN_defense• CaMeL offers a promising new direction for mitigating prompt injection attacks: https://simonwillison.net/2025/Apr/11/camel• Trustible: https://trustible.ai• Repello: https://repello.ai• Do not write that jailbreak paper: https://javirando.com/blog/2024/jailbreaks—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

Elena Verna is the head of growth at Lovable, the leading AI-powered app builder that hit $200 million in annual recurring revenue in under a year with just 100 employees. In this record fourth appearance on the podcast, Elena shares how the traditional growth playbook has been completely rewritten for AI companies. She explains why Lovable focuses on innovation over optimization, how they’ve shifted from activation to building new features, and why giving away their product for free has become their most powerful growth strategy.We discuss:1. Why 60% to 70% of traditional growth tactics no longer apply in AI2. Why you have to re-find product-market fit every 3 months3. The specific growth tactics driving Lovable’s unprecedented growth4. Why giving away product is a growth strategy that beats paid ads5. “Minimum lovable product” as the new standard (not minimum viable product)6. Why activation now belongs to product teams, not growth teams7. Whether you should join an AI startup (honest tradeoffs)—Brought to you by:WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUsVercel—Your collaborative AI assistant to design, iterate, and scale full-stack applications for the webPersona—A global leader in digital identity verification—Transcript: ⁠https://www.lennysnewsletter.com/p/the-new-ai-growth-playbook-for-2026-elena-verna⁠—My biggest takeaways (for paid newsletter subscribers): ⁠https://www.lennysnewsletter.com/i/181207556/my-biggest-takeaways-from-this-conversation⁠—Where to find Elena Verna:• X: https://x.com/elenaverna• LinkedIn: https://www.linkedin.com/in/elenaverna• Newsletter: https://www.elenaverna.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 Elena Verna(05:19) The scale and growth of Lovable(08:55) Confidence in Lovable as a business(12:17) Retention at Lovable(15:02) Lovable’s unique growth levers(28:13) The role of marketing in Lovable’s success(38:09) Launching new features(40:59) Hiring and team dynamics(43:17) The value of vibe coding(49:46) The importance of community(51:47) Giving away your product for free(56:26) Tripling their company size(01:00:23) Product-market-fit challenges(01:08:50) Advice for joining AI companies(01:12:00) Work-life balance(01:15:20) What it’s like to work at Lovable(01:19:45) Women in tech(01:25:29) Final thoughts and lightning round—Referenced:• Elena Verna on how B2B growth is changing, product-led growth, product-led sales, why you should go freemium not trial, what features to make free, and much more: https://www.lennysnewsletter.com/p/elena-verna-on-why-every-company• The ultimate guide to product-led sales | Elena Verna: https://www.lennysnewsletter.com/p/the-ultimate-guide-to-product-led• 10 growth tactics that never work | Elena Verna (Amplitude, Miro, Dropbox, SurveyMonkey): https://www.lennysnewsletter.com/p/10-growth-tactics-that-never-work-elena-verna• Lovable: https://lovable.dev• 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• Stripe: https://stripe.com• What differentiates the highest-performing product teams | John Cutler (Amplitude, The Beautiful Mess): https://www.lennysnewsletter.com/p/what-differentiates-the-highest-performing• How to win in the AI era: Ship a feature every week, embrace technical debt, ruthlessly cut scope, and create magic your competitors can’t copy | Gaurav Misra (CEO and co-founder of Captions): https://www.lennysnewsletter.com/p/how-to-win-in-the-ai-era-gaurav-misra• “Dumbest idea I’ve heard” to $100M ARR: Inside the rise of Gamma | Grant Lee (CEO): https://www.lennysnewsletter.com/p/how-50-people-built-a-profitable-ai-unicorn• Eric Ries on LinkedIn: https://www.linkedin.com/in/eries• Elena’s post on LinkedIn about Lovable Missions: https://www.linkedin.com/posts/elenaverna_everythingispossible-lovableway-activity-7401627519646474242-hn6e• SheBuilds: https://shebuilds.lovable.app• Shopify + Lovable: https://lovable.dev/shopify• The Product-Market Fit Treadmill: Why every AI company is sprinting just to stay in place: https://www.elenaverna.com/p/the-product-market-fit-treadmill• Cursor: https://cursor.com• The rise of Cursor: The $300M ARR AI tool that engineers can’t stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell• Unorthodox frameworks for growing your product, career, and impact | Bangaly Kaba (YouTube, Instagram, Facebook, Instacart): https://www.lennysnewsletter.com/p/frameworks-for-growing-your-career-bangaly-kaba• The adjacent user: https://brianbalfour.com/quick-takes/the-adjacent-user• Granola: https://www.granola.ai• Wispr Flow: https://wisprflow.ai• I’m worried about women in tech: https://www.elenaverna.com/p/im-worried-about-women-in-tech• Slack founder: Mental models for building products people love ft. Stewart Butterfield: https://www.lennysnewsletter.com/p/slack-founder-stewart-butterfield—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