All Episodes

Ethan Smith is the CEO of Graphite—the leading SEO growth agency—and my go-to expert on SEO. After 18 years of mastering traditional SEO, Ethan has been at the forefront of what is called AEO: answer engine optimization, or, more simply, getting your product to show up in ChatGPT/Claude/Gemini/Perplexity answers. He’s discovered that ChatGPT traffic converts six times better than Google search—and most companies are completely missing this opportunity. *In our conversation, we discuss:* 1. His 7-step playbook to rank #1 in ChatGPT 2. Why ChatGPT traffic converts 6x better than Google 3. How early-stage startups can win at AEO immediately (unlike with SEO, which takes years) 4. The three tactics that actually work: landing pages, YouTube videos, and Reddit comments 5. Why help-center content can suddenly be your highest-ROI investment 6. The specific Reddit strategy that works (spoiler: be authentic) 7. Why AI-generated content doesn’t work *Brought to you by:* Orkes—The enterprise platform for reliable applications and agentic workflows: https://www.orkes.io/ Vanta—Automate compliance. Simplify security: https://vanta.com/lenny Great Question—Empower everyone to run great research: https://www.greatquestion.com/lenny *Transcript:* https://www.lennysnewsletter.com/p/the-ultimate-guide-to-aeo-ethan-smith *My biggest takeaways (for paid newsletter subscribers):* https://www.lennysnewsletter.com/i/172703231/my-biggest-takeaways-from-this-conversation *Where to find Ethan Smith:* • Twitter: https://twitter.com/ethan_l_s • LinkedIn: https://bit.ly/ethans-linkedin • Graphite: https://graphite.io/ • Graphite Research Papers: https://bit.ly/graphite-five-percent *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) Welcome back, Ethan (04:34) The changing landscape of SEO (06:19) AEO (answer engine optimization) vs. GEO (generative engine optimization) (08:13) The impact of AEO (11:51) How early-stage startups can win at AEO (14:34) The quality of AEO leads (15:35) On-site vs. off-site traffic (16:32) Reddit’s role in AEO and avoiding spam (20:11) How AI models use citations (RAG) (21:41) Key principles for winning at AEO (25:00) Avoiding hyper-SEOed content, and the importance of originality (28:55) Actionable AEO playbook: steps and experiments (33:35) Tracking, measuring, and share of voice (38:34) Adapting AEO for B2B, commerce, and early-stage companies (41:11) Is letting AI index your content good? (43:06) Experimentation, control groups, and measuring results (46:15) The future of AEO, SEO, and search channels (51:35) AI-generated content: what works and what doesn’t (55:25) The dangers of infinite AI derivatives (58:44) The future: convergence of LLMs and search (01:00:40) Help-center optimization and the long tail (01:03:18) Lightning round and final thoughts *Referenced:* • AEO Tools: https://bit.ly/graphite-aeo-tool • The ultimate guide to SEO | Ethan Smith (Graphite): https://www.lennysnewsletter.com/p/the-ultimate-guide-to-seo-ethan-smith • Inside ChatGPT: The fastest-growing product in history | Nick Turley (Head of ChatGPT at OpenAI): https://www.lennysnewsletter.com/p/inside-chatgpt-nick-turley • Webflow: https://webflow.com/ • YouTube: https://youtube.com/ • Reddit: https://www.reddit.com/ • Quora: https://www.quora.com/ • An inside look at Deel’s unprecedented growth | Meltem Kuran Berkowitz (Head of Growth): https://www.lennysnewsletter.com/p/an-inside-look-at-deels-unprecedented • Dotdash Meredith: https://www.people.inc/ • Forbes: https://www.forbes.com/ • Vimeo: https://vimeo.com/ • Perplexity: https://www.perplexity.ai/ • Gemini: https://gemini.google.com/ • ChatGPT: https://chatgpt.com/ • Claude: https://claude.ai/ • TechRadar: https://www.techradar.com/ • Yelp: https://www.yelp.com • Tripadvisor: https://www.tripadvisor.com/ • TikTok: https://www.tiktok.com/ • Why ChatGPT will be the next big growth channel (and how to capitalize on it) | Brian Balfour (Reforge): https://www.lennysnewsletter.com/p/why-chatgpt-will-be-the-next-big-growth-channel-brian-balfour • AI SEO: Latest Market Intelligence & Landscape Analysis—Summer Sessions: https://www.youtube.com/watch?v=cm589PmhIOY • AI Content Study: https://bit.ly/ai-content-white-paper • Free AI detector: https://surferseo.com/ai-content-detector/ • Common Crawl: https://commoncrawl.org/ • AI models collapse when trained on recursively generated data: https://www.nature.com/articles/s41586-024-07566-y • Looker: https://cloud.google.com/looker/ ...References continued at: https://www.lennysnewsletter.com/p/the-ultimate-guide-to-aeo-ethan-smith _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.

Ben Horowitz is the co-founder of Andreessen Horowitz, Silicon Valley’s largest and most influential venture capital firm, with over $46B in committed capital across multiple funds. He took Loudcloud public with just $2 million in revenue (dubbed “the IPO from hell”), sold it for $1.6 billion, and has backed companies from Facebook to Stripe to Airbnb to OpenAI to Databricks (now worth more than $100 billion). His management philosophy—forged through near-death experiences and refined through coaching hundreds of CEOs—contradicts most conventional startup wisdom. *In our conversation, Ben shares:* 1. Why “founder mode” is half right and half dangerously wrong 2. The story behind “Good Product Manager/Bad Product Manager” and why it went viral despite being written in anger 3. Where the biggest AI startup opportunities remain 4. Why you need to run toward fear, never away 5. The one trait that predicts that a founder will fail as CEO 6. Inside Paid in Full, Ben’s nonprofit awarding pensions to pioneering hip-hop artists *Brought to you by:* DX—The developer intelligence platform designed by leading researchers: https://getdx.com/lenny Basecamp—The famously straightforward project management system from 37signals: https://www.basecamp.com/lenny Miro—A collaborative visual platform where your best work comes to life: https://miro.com/lenny *Transcript:* https://www.lennysnewsletter.com/p/46b-of-hard-truths-from-ben-horowitz *My biggest takeaways (for paid newsletter subscribers):* ⁠https://www.lennysnewsletter.com/i/172439345/my-biggest-takeaways-from-this-conversation *Where to find Ben Horowitz:* • X: https://x.com/bhorowitz • LinkedIn: https://www.linkedin.com/in/behorowitz/ • Website: https://benhorowitz.com/ • Andreessen Horowitz’s website: https://a16z.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 Ben Horowitz (04:09) Important leadership lessons from Shaka Senghor (10:15) Running toward fear and why hesitation kills companies (19:35) Who shouldn’t start a company (22:36) The Databricks story: thinking bigger (24:54) Managerial leverage and CEO psychology (28:06) When founders should be replaced as CEOs (31:20) Normalizing failure for CEOs (37:57) Counterintuitive lessons about building companies (42:31) “Good Product Manager/Bad Product Manager” (48:21) Product managers as leaders (51:16) Why a16z invested in Adam Neumann after WeWork (56:23) Is AI in a bubble? (01:02:43) The biggest opportunities in AI (01:12:51) Why U.S. leadership in AI matters (01:18:53) The Paid in Full Foundation for hip-hop pioneers (01:23:18) Lightning round: book recommendations, products, and life mottos *Referenced:* • Shaka Senghor on The Joe Rogan Experience: https://open.spotify.com/episode/79neOSawKbrxY6Tl2wV1Kx • 1999 Martha’s Vineyard plane crash: https://en.wikipedia.org/wiki/1999_Martha%27s_Vineyard_plane_crash • John Reed: https://en.wikipedia.org/wiki/John_S._Reed# • LoudCrowd: https://loudcrowd.com/ • Marc Andreessen on X: https://x.com/pmarca • Ali Ghodsi on LinkedIn: https://www.linkedin.com/in/alighodsi/ • Databricks: https://www.databricks.com/ • Ion Stoica on LinkedIn: https://www.linkedin.com/in/ionstoica/ • Hadoop: https://hadoop.apache.org/ • The Sad Truth About Developing Executives: https://a16z.com/the-sad-truth-about-developing-executives/ • Mark Zuckerberg on Facebook: https://www.facebook.com/zuck/ • Sam Altman on X: https://x.com/sama • Brian Chesky’s new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach • Brian Chesky—Founder Mode & The Art of Hiring: https://www.youtube.com/watch?v=aFOGlNL39xs • Bob Iger: https://en.wikipedia.org/wiki/Bob_Iger • Larry Page: https://en.wikipedia.org/wiki/Larry_Page • Kanye West: https://en.wikipedia.org/wiki/Kanye_West • Diddy: https://en.wikipedia.org/wiki/Sean_Combs • Arsalan Tavakoli on LinkedIn: https://www.linkedin.com/in/arsalantavakoli/ • Good Product Manager/Bad Product Manager: https://a16z.com/good-product-manager-bad-product-manager/ • Netscape: https://en.wikipedia.org/wiki/Netscape • Jensen Huang on LinkedIn: https://www.linkedin.com/in/jenhsunhuang/ • David Weiden on LinkedIn: https://www.linkedin.com/in/davidweiden/ • Raghu Raghuram on LinkedIn: https://www.linkedin.com/in/raghuraghuram/ • Adam Neumann on X: https://en.wikipedia.org/wiki/Adam_Neumann • WeWork: https://www.wework.com/ • Cluely: https://cluely.com/ ...References continued at: https://www.lennysnewsletter.com/p/46b-of-hard-truths-from-ben-horowitz _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.

Howie Liu is the co-founder and CEO of Airtable, the no-code platform valued at around $12 billion. After a viral tweet declared “Airtable is dead” based on incorrect data, Howie led a radical transformation: reorganizing the entire company around AI, becoming an “IC CEO” who codes daily, and achieving over $100 million in free cash flow. *What you’ll learn:* 1. The “fast thinking” vs. “slow thinking” team structure that lets Airtable ship AI features weekly (inspired by Daniel Kahneman) 2. Why Howie uses AI hourly (not daily) and is Airtable’s #1 inference-cost user globally 3. Why CEOs must become ICs again in the AI era (and how to restructure your calendar to make it possible) 4. Why “playing” with AI tools should be mandatory—Howie tells employees to cancel all meetings for a week to experiment 5. The specific skills product managers, engineers, and designers need to develop to succeed in the AI era 6. Why evals can kill innovation (and when to use “vibes” instead) *Brought to you by:* LucidLink—Real-time cloud storage for teams: https://www.lucidlink.com/lenny DX—The developer intelligence platform designed by leading researchers: http://getdx.com/lenny Claude.ai—The AI for problem solvers and enterprise: http://claude.ai/ *Transcript:* ⁠⁠⁠https://www.lennysnewsletter.com/p/how-we-restructured-airtables-entire-org-for-ai *My biggest takeaways (for paid newsletter subscribers):* ⁠https://www.lennysnewsletter.com/i/171904193/my-biggest-takeaways-from-this-conversation *Where to find Howie Liu* • X: https://x.com/howietl • LinkedIn: https://www.linkedin.com/in/howieliu/ • Email: howie@airtable.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 Howie Liu and Airtable (04:05) The “Airtable is dead” viral tweet controversy (08:07) The rise of IC CEOs (10:57) AI’s paradigm shift in product development (16:27) Specific changes Airtable has made (21:38) Fast- and slow-thinking teams (32:57) The emergence of new form factors in AI models (34:48) Airtable’s vision and philosophy (40:20) Empowering teams with AI tools (46:50) Encouraging experimentation and play (50:55) Cross-functional skills in product teams (01:03:35) The importance of evals and open-ended testing (01:08:06) Key strategies for AI-driven success (01:12:43) Counterintuitive startup wisdom (01:22:21) Don't step away from the details that you love (01:25:50) Advice for aspiring engineers and designers (01:30:00) Lightning round and final thoughts *Referenced:* • Airtable: https://www.airtable.com/ • All In podcast: https://allin.com/ • Nikita Bier on X: https://x.com/nikitabier • Figma: https://www.figma.com/ • The AI-native startup: 5 products, 7-figure revenue, 100% AI-written code | Dan Shipper (co-founder and CEO of Every): https://www.lennysnewsletter.com/p/inside-every-dan-shipper • Every: https://every.to/ • 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 • Windsurf: https://windsurf.com/ • Building a magical AI code editor used by over 1 million developers in four months: The untold story of Windsurf | Varun Mohan (co-founder and CEO): https://www.lennysnewsletter.com/p/the-untold-story-of-windsurf-varun-mohan • Rippling: https://www.rippling.com/ • Omni: https://www.airtable.com/lp/ai-psu-plp • How ChatGPT accidentally became the fastest-growing product in history | Nick Turley (Head of ChatGPT at OpenAI): https://www.lennysnewsletter.com/p/inside-chatgpt-nick-turley • Palantir: https://www.palantir.com/ • Harvey: https://www.harvey.ai/ • v0: https://v0.dev/ • 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 • Lovable: https://lovable.dev/ • Building Lovable: $10M ARR in 60 days with 15 people | Anton Osika (CEO and co-founder): https://www.lennysnewsletter.com/p/building-lovable-anton-osika ...References continued at: https://www.lennysnewsletter.com/p/how-we-restructured-airtables-entire-org-for-ai _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.

Asha Sharma leads AI product strategy at Microsoft, where she works with thousands of companies building AI products and has unique visibility into what’s working (and what’s not) across more than 15,000 startups and enterprises. Before Microsoft, Asha was COO at Instacart, and VP of Product & Engineering at Meta, notably leading product for Messenger. *What you’ll learn:* 1. Why we’re moving from “product as artifact” to “product as organism” and what this means for builders 2. Microsoft’s “seasons” planning framework that allows them to adapt quickly in the AI era 3. The death of the org chart: how agents are turning hierarchies into task networks and why “the loop, not the lane” is the new organizing principle 4. Why post-training will soon see more investment than pre-training—and how to build your own AI moat with fine-tuning 5. Her prediction for the “agentic society”—where org charts become work charts and agents outnumber humans in your company 6. The three-phase pattern every successful AI company follows (and why most fail at phase one) 7. The rise of code-native interfaces and why GUIs might be going the way of the desktop 8. What Asha learned from Satya Nadella about optimism *Brought to you by:* Enterpret—Transform customer feedback into product growth: https://enterpret.com/lenny DX—The developer intelligence platform designed by leading researchers: https://getdx.com/lenny Fin—The #1 AI agent for customer service: https://fin.ai/lenny *Transcript:* ⁠https://www.lennysnewsletter.com/p/how-80000-companies-build-with-ai-asha-sharma⁠⁠ *My biggest takeaways (for paid newsletter subscribers):* ⁠https://www.lennysnewsletter.com/i/171413445/my-biggest-takeaways-from-this-conversation *Where to find Asha Sharma:* • LinkedIn: https://www.linkedin.com/in/aboutasha/ • Blog: https://azure.microsoft.com/en-us/blog/author/asha-sharma/ *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 Asha Sharma (04:18) From “product as artifact” to “product as organism” (06:20) The rise of post-training and the future of AI product development (09:10) Successful AI companies: patterns and pitfalls (12:01) The evolution of full-stack builders (14:15) “The loop, not the lane”—the new organizing principle (16:24) The future of user interfaces: from GUI to code-native (19:34) The rise of the agentic society (22:58) The “work chart” vs. the “org chart” (26:24) How Microsoft is using agents (28:23) Planning and strategy in the AI landscape (35:38) The importance of platform fundamentals (39:31) Lessons from industry giants (42:10) What’s driving Asha (44:30) Reinforcement learning (RL) and optimization loops (49:19) Lightning round and final thoughts *Referenced:* • Copilot: https://copilot.microsoft.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 • Inside ChatGPT: The fastest growing product in history | Nick Turley (Head of ChatGPT at OpenAI): https://www.lennysnewsletter.com/p/inside-chatgpt-nick-turley • GitHub: https://github.com • Dragon Medical One: https://www.microsoft.com/en-us/health-solutions/clinical-workflow/dragon-medical-one • Windsurf: https://windsurf.com/ • Building a magical AI code editor used by over 1 million developers in four months: The untold story of Windsurf | Varun Mohan (co-founder and CEO): https://www.lennysnewsletter.com/p/the-untold-story-of-windsurf-varun-mohan • Lovable: https://lovable.dev/ • Building Lovable: $10M ARR in 60 days with 15 people | Anton Osika (CEO and co-founder): https://www.lennysnewsletter.com/p/building-lovable-anton-osika • Bolt: http://bolt.com • 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 • 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 • 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 • Sierra: https://sierra.ai/ • Spark: https://github.com/features/spark • Peter Yang on X: https://x.com/petergyang • How AI will impact product management: https://www.lennysnewsletter.com/p/how-ai-will-impact-product-management ...References continued at: https://www.lennysnewsletter.com/p/how-80000-companies-build-with-ai-asha-sharma _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.

Garrett Lord is co-founder and CEO of Handshake, which started as a career network for college students and new grads but recently discovered something extraordinary: they were sitting on the world’s largest network of academic experts—exactly what frontier AI labs desperately needed. With 500,000 PhDs and 3 million advanced degree holders creating training data, in just eight months they’ve built a new business that hit $50 million in revenue in its first four months and is on track to blow past $100M in the first 12 months. *What you’ll learn:* 1. How Handshake found an opportunity to leverage their proprietary network of experts to launch a data-labeling business that’s on track to blow past $100 million ARR in 12 months 2. Why AI models need human experts (e.g. physics PhDs) to improve, and what this “data labeling” actually involves 3. Inside the actual work: what a biology PhD does for 8 hours that makes GPT-5 smarter 4. The playbook for building a startup inside a startup: separate teams, separate offices, separate everything 5. Why the shift from “generalist” to “expert” data labeling created a once-in-a-lifetime business opportunity 6. Why AI won’t eliminate entry-level jobs—it’s creating “Iron Man suits” that make junior employees 10x more productive *Brought to you by:* CodeRabbit—Cut code review time and bugs in half. Instantly: https://coderabbit.link/lenny Orkes—The enterprise platform for reliable applications and agentic workflows: https://www.orkes.io/ Claude.ai—The AI for problem solvers and enterprise: https://www.claude.ai/lenny *Transcript:* https://www.lennysnewsletter.com/p/inside-handshake-garrett-lord *My biggest takeaways (for paid newsletter subscribers):* https://www.lennysnewsletter.com/i/171410958/my-biggest-takeaways-from-this-conversation *Where to find Garrett Lord:* • X: https://x.com/garrettlord • LinkedIn: https://www.linkedin.com/in/garrettlord/ • Email: Garrett@joinhandshake.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 Garrett Lord (05:00) Understanding data labeling and its importance (13:08) The role of experts in AI model training (15:35) The future of AI and human collaboration (24:17) Why AI won’t eliminate entry-level jobs (27:58) The continuous improvement of AI models (33:05) The emergence of Handshake’s new business model (37:07) Incubating new ideas in established companies (40:42) Handshake's competitive advantage (45:43) Scaling up and meeting market demand (48:38) Overcoming challenges and adapting (53:08) The importance of separate teams and ownership (57:26) The future of job matching with AI (01:00:30) The biggest bottlenecks to advancing models further (01:02:37) Lightning round and final thoughts *Referenced:* • GPQA: https://github.com/idavidrein/gpqa • Handshake: https://joinhandshake.com/ • 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 • 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 • Goldman Sachs: https://www.goldmansachs.com/ • General Motors: https://www.gm.com/ • Google: https://about.google/ • Sahil Bhaiwala on LinkedIn: https://www.linkedin.com/in/sahil-bhaiwala-459b0354/ • Francisco “Paco” Guzman on LinkedIn: https://www.linkedin.com/in/guzmanhe/ • Avery Yip on LinkedIn: https://www.linkedin.com/in/averyyip/ • Game of Thrones on HBO: https://www.hbomax.com/shows/game-of-thrones/4f6b4985-2dc9-4ab6-ac79-d60f0860b0ac • SNOO: https://www.happiestbaby.com/products/snoo-smart-bassinet • Careers at Handshake: https://joinhandshake.com/careers/ *Recommended books:* • Zero to One: Notes on Startups, or How to Build the Future: https://www.amazon.com/Zero-One-Notes-Startups-Future/dp/0804139296 • The Hard Thing About Hard Things: Building a Business When There Are No Easy Answers―Straight Talk on the Challenges of Entrepreneurship: https://www.amazon.com/Hard-Thing-About-Things-Building/dp/0062273205 _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.

Eoghan McCabe is the founder and CEO of Intercom, a customer service platform that has successfully pivoted to become an AI-first company with its agent product, Fin. After stepping away from the CEO role in 2020 due to health issues, Eoghan returned to find the company’s growth had stalled. Just one month after his return, ChatGPT launched, and within six weeks, Intercom had a working prototype of what would become Fin. In this conversation, Eoghan shares the brutal reality of transforming a late-stage SaaS business valued at multiple billions into an AI-first company that’s now growing faster than most public software companies. *We discuss:* 1. Why Eoghan believes most late-stage companies won’t survive the AI transition 2. The “founder mode” transformation that required firing 40% of staff and resulted in 98% employee satisfaction 3. Why having “nothing to lose” is the ultimate advantage in AI transformation (and why comfortable companies will fail) 4. How Intercom transformed from a plateauing SaaS business to an AI-first company growing at 300%+ 5. How Intercom’s pricing evolved from “the most hated in SaaS” to a model that charges just $0.99 per resolved ticket 6. The cultural transformation required to compete with AI-native startups 7. How 12 years of therapy and a period of “ego death” shaped Eoghan’s leadership approach *Transcript:* https://www.lennysnewsletter.com/p/how-intercom-rose-from-the-ashes-eoghan-mccabe *My biggest takeaways (for paid newsletter subscribers):* https://www.lennysnewsletter.com/i/170710700/my-biggest-takeaways-from-this-conversation *Brought to you by:* Great Question—Empower everyone to run great research: https://www.greatquestion.com/lenny WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs: https://workos.com/lenny DX—The developer intelligence platform designed by leading researchers: https://getdx.com/lenny *Where to find Eoghan McCabe:* • X: https://x.com/eoghan • LinkedIn: https://www.linkedin.com/in/eoghanmccabe/ • Website: https://eoghanmccabe.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 Eoghan (05:00) The state of Intercom (09:53) The decision to pivot to AI (12:33) Why Eoghan is "anti-bot" in customer service (16:19) Pricing strategy evolution (19:26) Implementing the AI transformation (26:11) Cultural and organizational changes (31:18) Surviving a coup attempt (40:05) The future of AI and business (45:11) AI's impact on jobs (48:44) AI and human creativity (50:26) The importance of young AI talent (55:00) The cultural shift in AI adoption (58:00) Personal growth and leadership (01:04:34) Intercom’s success in producing product leaders (01:11:05) Intercom’s unique company culture (01:14:11) Lightning round and final thoughts *Referenced:* • Intercom: https://www.intercom.com/ • Fin: https://fin.ai/ • Des Traynor on LinkedIn: https://www.linkedin.com/in/destraynor/ • 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 • Brian Chesky’s new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach • Behind the founder: Marc Benioff: https://www.lennysnewsletter.com/p/behind-the-founder-marc-benioff • 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 • Fergal Reid on LinkedIn: https://www.linkedin.com/in/fergalreid/ • How Perplexity builds product: https://www.lennysnewsletter.com/p/how-perplexity-builds-product • Yosi Amram’s website: https://yamram.com/ • (Nathaniel Russell) Ego Death Now: https://heythereprojects.shop/products/copy-of-nathaniel-russell-space-is-a-place • Daniel Kahneman: https://en.wikipedia.org/wiki/Daniel_Kahneman • Palantir: https://www.palantir.com/ • Stripe: https://stripe.com/ • Revolut: https://www.revolut.com/en-US/ • Paul Adams on LinkedIn: https://www.linkedin.com/in/pauladams • What AI means for your product strategy | Paul Adams (CPO of Intercom): https://www.lennysnewsletter.com/p/what-ai-means-for-your-product-strategy ...References continued at: ⁠https://www.lennysnewsletter.com/p/how-intercom-rose-from-the-ashes-eoghan-mccabe⁠ _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.

Brian Balfour is the founder of Reforge, the former VP of Growth at HubSpot, and a student (and teacher) of product growth. Brian has studied every major platform shift—from Facebook to Apple to Google—and he’s spotted a pattern that’s about to repeat with ChatGPT. *In this conversation, you’ll learn:* 1. The 4-step cycle every platform follows (and why ChatGPT just entered step 2) 2. Why ChatGPT’s platform launch could be bigger than Facebook’s early platform 3. The exact signals that ChatGPT will launch a third-party platform within six months 4. Why you have six months (not years) to make your platform bet 5. Why companies that don’t integrate with ChatGPT will lose to competitors that do 6. How Zynga grew to $1B by betting on Facebook’s platform early (before it was obvious) 7. Why so few companies are actually doing what they need to be doing right now *Brought to you by:* DX—The developer intelligence platform designed by leading researchers: http://getdx.com/lenny Basecamp—The famously straightforward project management system from 37signals: https://www.basecamp.com/lenny Miro—A collaborative visual platform where your best work comes to life: https://miro.com/lenny *Transcript:* https://www.lennysnewsletter.com/p/why-chatgpt-will-be-the-next-big-growth-channel-brian-balfour *My biggest takeaways (for paid newsletter subscribers):* https://www.lennysnewsletter.com/i/170294620/my-biggest-takeaways-from-this-conversation *Where to find Brian Balfour:* • X: https://twitter.com/bbalfour • LinkedIn: https://www.linkedin.com/in/bbalfour/ • Website: https://brianbalfour.com/ • Substack: https://blog.brianbalfour.com/ • Podcast: https://www.reforge.com/podcast/unsolicited-feedback *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) Welcome back, Brian! (04:13) The changing landscape of product growth (05:09) The importance of distribution (08:14) The role of new distribution platforms (09:45) The four-step cycle of distribution platforms (17:38) Examples of platform cycles (30:01) The rise of ChatGPT (44:47) The future of AI agents (46:01) Preferred partners and platform credibility (47:18) Monetization mechanisms and free tiers (48:14) Betting strategies for startups (01:04:34) Adopting AI tools: challenges and strategies (01:08:41) The importance of hard constraints (01:14:23) Effective AI adoption in companies (01:19:05) Lightning round and final thoughts *Referenced:* • The Next Great Distribution Shift: https://blog.brianbalfour.com/p/the-next-great-distribution-shift • Brian Balfour: 10 lessons on career, growth, and life: https://www.lennysnewsletter.com/p/brian-balfour-10-lessons-on-career • This Week #9: Breaking into growth, leading with influence, and (not) stepping on toes: https://www.lennysnewsletter.com/p/this-week-9-breaking-into-growth • Distribution vs. Innovation: https://a16z.com/distribution-vs-innovation/ • On Platform Shifts and AI: https://caseyaccidental.com/on-platform-shifts-and-ai/ • How to sell your ideas and rise within your company | Casey Winters, Eventbrite: https://www.lennysnewsletter.com/p/how-to-sell-your-ideas-and-rise-within • Thinking beyond frameworks | Casey Winters (Pinterest, Eventbrite, Airbnb, Tinder, Canva, Reddit, Grubhub): https://www.lennysnewsletter.com/p/thinking-beyond-frameworks-casey • ChatGPT: https://chatgpt.com/ • Claude: https://claude.ai/ • Gemini: https://gemini.google.com/ • Vine: https://en.wikipedia.org/wiki/Vine_(service) • Periscope: https://en.wikipedia.org/wiki/Periscope_(service) • Myspace: https://en.wikipedia.org/wiki/Myspace • Friendster: https://en.wikipedia.org/wiki/Friendster • AltaVista: https://en.wikipedia.org/wiki/AltaVista • Lycos: https://www.lycos.com/ • HubSpot: https://www.hubspot.com/ • Zynga: https://www.zynga.com/ • TBPN: https://www.tbpn.com/ • Deedy Das on LinkedIn: https://www.linkedin.com/in/debarghyadas/ • ChatGPT’s product retention curves are a product manager's wet dream: https://www.linkedin.com/posts/debarghyadas_chatgpts-product-retention-curves-are-a-activity-7338384752393035776-ice1/ • Windsurf: https://windsurf.com/ • Building a magical AI code editor used by over 1 million developers in four months: The untold story of Windsurf | Varun Mohan (co-founder and CEO): https://www.lennysnewsletter.com/p/the-untold-story-of-windsurf-varun-mohan ...References continued at: https://www.lennysnewsletter.com/p/why-chatgpt-will-be-the-next-big-growth-channel-brian-balfour _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.

Matt LeMay spent 13 years as a music critic at Pitchfork before becoming one of product management’s most influential voices. He’s consulted with companies from startups to Fortune 500s and authored two essential PM books, including Impact-First Product Teams. After watching countless product teams get laid off despite “doing everything right,” he discovered a harsh truth: most PMs are optimizing for the wrong things. *In this conversation, you’ll learn:* 1. The one question that predicts if your team will survive the next layoffs (and why most teams can’t answer it) 2. Why following product “best practices” perfectly can actually accelerate your path to unemployment 3. The “low-impact PM death spiral”—how teams accidentally make themselves irrelevant 4. How to push back on executives without saying “no” (the options, plus a recommendation framework) 5. The counterintuitive reason why the happiest PMs are also the most commercially minded 6. The Liz Phair review that made Matt an internet villain for 22 years—and what it taught him about product management *Brought to you by:* Enterpret—Transform customer feedback into product growth: https://enterpret.com/lenny Pragmatic Institute—Industry‑recognized product, marketing, and AI training & certifications: https://pragmaticinstitute.com/lenny Claude.ai—The AI for problem solvers and enterprise: http://claude.ai/ *Transcript:* https://www.lennysnewsletter.com/p/the-one-question-that-saves-product-careers-matt-lemay *My biggest takeaways (for paid newsletter subscribers):* https://www.lennysnewsletter.com/i/168109376/my-biggest-takeaways-from-this-conversation *Where to find Matt LeMay:* • Instagram: https://www.instagram.com/mttlmy • LinkedIn: https://www.linkedin.com/in/mattlemay/ • Website: https://mattlemay.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 LeMay (04:23) Matt’s background and transition to product management (06:47) The goal of Matt's new book (12:00) How to stress test your thinking as a PM (15:32) Thinking like the CEO (17:33) The role of a product manager (23:36) The low-impact PM death spiral (27:47) Case study: Mailchimp’s transition to a platform company (32:53) Radical acceptance (41:24) Embracing constraints in product management (44:23) Steps to become an impact-first product team (49:38) Setting effective goals (01:02:15) Prioritization and impact estimation (01:07:58) Navigating stakeholder management (01:12:35) Summarizing the 3 steps (01:16:36) Lightning round and final thoughts *Referenced:* • Pitchfork: https://pitchfork.com/ • Daniel Ek’s memo: https://newsroom.spotify.com/2023-12-04/an-update-on-december-2023-organizational-changes/ • How to create a winning product strategy | Melissa Perri: https://www.lennysnewsletter.com/p/how-to-create-a-winning-product-strategy • Everything you’ve ever wanted to know about SAFe and the product owner role | Melissa Perri (author, founder of Product Institute): https://www.lennysnewsletter.com/p/product-owners-melissa-perri • Mailchimp: https://mailchimp.com/ • Intuit: https://www.intuit.com/ • Natalia Williams on LinkedIn: https://www.linkedin.com/in/nataliatwilliams/ • The ultimate guide to OKRs | Christina Wodtke (Stanford): https://www.lennysnewsletter.com/p/the-ultimate-guide-to-okrs-christina • Miro: https://miro.com/ • Prioritizing: https://www.lennysnewsletter.com/p/prioritizing • Temptation Island on Netflix: https://www.netflix.com/title/81744518 • Mark L. Walberg’s website: https://markwalbergtv.com/about • Antiques Roadshow on PBS: https://www.pbs.org/wgbh/roadshow/ • Milkman amp: https://milkmansound.com/collections/amplifiers/products/the-amp • Matt’s review of Liz Phair’s self-titled album: https://pitchfork.com/reviews/albums/6255-liz-phair/ • Pitchfork Critic Apologizes for Bashing Liz Phair Album; Singer Graciously Accepts: https://variety.com/2019/music/news/pitchfork-critic-apologizes-liz-phair-album-review-zero-score-1203326897/ • RedMonk: https://redmonk.com/ *Recommended books:* • Product Management in Practice: A Practical, Tactical Guide for Your First Day and Every Day After: https://www.amazon.com/Product-Management-Practice-Practical-Tactical/dp/1098119738/r • Impact-First Product Teams: Define Success. Do Work That Matters. Be Indispensable.: https://www.amazon.com/Impact-first-Product-Teams-Success-Indispensable/dp/B0DVH4R3QJ • Escaping the Build Trap: How Effective Product Management Creates Real Value: https://www.amazon.com/Escaping-Build-Trap-Effective-Management/dp/B08B46C8R1/ ...Resources continued at: https://www.lennysnewsletter.com/p/the-one-question-that-saves-product-careers-matt-lemay _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.

Nick Turley is Head of ChatGPT, the fastest-growing product in history, with 700 million weekly active users (10% of the world’s population). He was part of the original hackathon team that shipped ChatGPT in just 10 days, helped it grow from zero to billions in revenue, and leads product for what may be the most consequential product of our time. We recorded this the day before GPT-5 launched. *We discuss:* 1. The 10-day sprint from deciding to ship ChatGPT to Sam Altman’s tweet (and why it was originally called “Chat with GPT-3.5”) 2. How they ran a willingness-to-pay Van Westendorp survey in their Discord to decide on the $20/month price point that everyone copied 3. The “Is it maximally accelerated?” philosophy that drives OpenAI’s insane shipping velocity 4. Why ChatGPT’s retention curve “smiles”—users leave, then come back months later using it more 5. The accidental decisions that changed history, including not having a waitlist 6. The impact ChatGPT will have on SEO and product growth 7. The counterintuitive reason why shipping unpolished AI features beats waiting for perfection 8. Why ChatGPT intentionally shipped with that “ugly” model-chooser dropdown 9. How TikTok comments became a primary user research channel early on *Brought to you by:* Orkes—The enterprise platform for reliable applications and agentic workflows: https://www.orkes.io/ Vanta—Automate compliance. Simplify security: https://vanta.com/lenny PostHog—How developers build successful products: https://posthog.com/lenny *Transcript:* https://www.lennysnewsletter.com/p/inside-chatgpt-nick-turley *My biggest takeaways (for paid newsletter subscribers):* https://www.lennysnewsletter.com/i/170411252/my-biggest-takeaways-from-this-conversation *Where to find Nick Turley* • X: https://x.com/nickaturley • LinkedIn: https://www.linkedin.com/in/nicholasturley/ • Website: https://nickturley.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 Nick Turley (04:52) GPT-5 launch (09:13) The vision for ChatGPT and AI assistants (13:52) The early days of ChatGPT (17:14) The success and impact of ChatGPT (20:44) Product development and iteration (23:11) Maximally accelerated: the OpenAI approach (26:17) Retention and user engagement (33:42) The future of chat interfaces (36:31) The evolution of ChatGPT (38:52) Subscription model and pricing strategies (42:10) Enterprise adoption and challenges (44:10) Balancing multiple product lines (52:13) Emergent use cases and user feedback (01:02:15) OpenAI’s unique product development approach (01:05:07) The importance of team composition (01:08:50) Balancing speed and quality in AI development (01:14:23) The role of evals in product development (01:16:13) The future of AI-driven content and GPTs (01:21:51) Philosophy and product leadership (01:23:47) Career journey and advice (01:27:49) Lightning round and final thoughts *Referenced:* • GPT-5 and the new era of work: https://openai.com/index/gpt-5-new-era-of-work/ • Instacart: https://www.instacart.com/ • 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 • Sam Altman on X: https://x.com/sama • Figma: https://www.figma.com/ • Van Westendorp’s Price Sensitivity Meter: https://en.wikipedia.org/wiki/Van_Westendorp%27s_Price_Sensitivity_Meter • Rahul Vohra on LinkedIn: https://www.linkedin.com/in/rahulvohra/ • Superhuman’s secret to success: Ignoring most customer feedback, manually onboarding every new user, obsessing over every detail, and positioning around a single attribute: speed | Rahul Vohra (CEO): https://www.lennysnewsletter.com/p/superhumans-secret-to-success-rahul-vohra • Dropbox: http://dropbox.com/ • Airtable: https://www.airtable.com/ • Notion: https://www.notion.com/ • Instant Pot: https://instantpot.com/ • MS-DOS: https://en.wikipedia.org/wiki/MS-DOS • Expanding on what we missed with sycophancy: https://openai.com/index/expanding-on-sycophancy/ • What we’re optimizing ChatGPT for: https://openai.com/index/how-we're-optimizing-chatgpt/ • Charlie Munger’s quote: https://www.goodreads.com/quotes/11903426-show-me-the-incentive-and-i-ll-show-you-the-outcome • Anthropic’s CPO on what comes next | Mike Krieger (co-founder of Instagram): https://www.lennysnewsletter.com/p/anthropics-cpo-heres-what-comes-next • Beyond vibe checks: A PM’s complete guide to evals: https://www.lennysnewsletter.com/p/beyond-vibe-checks-a-pms-complete ...References continued at: https://www.lennysnewsletter.com/p/inside-chatgpt-nick-turley _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.

Chip Conley is the founder of Joie de Vivre hotels, the second-largest boutique hotel brand in the world. At age 52, he joined Airbnb as Head of Global Hospitality and Strategy, reporting to CEO Brian Chesky, who was 21 years younger. He earned the title of Airbnb’s “Modern Elder” by guiding the young founders on leadership and culture while learning Silicon Valley’s tech mindset himself. Today, Chip leads the Modern Elder Academy, the world’s first midlife wisdom school, and is the author of best-selling books like Wisdom@Work and Peak. He champions the idea that age and experience are assets—and that midlife can be a launchpad for renewed purpose and impact. *In this conversation, we discuss:* 1. The reality of Brian Chesky in “founder mode”—the good, bad, and stressful 2. How Chip went from running 52 boutique hotels to becoming Airbnb’s in-house mentor in his 50s 3. The “mentor and intern” mindset: how to simultaneously teach others and stay curious like a beginner 4. Why AI might actually favor older workers (hint: human wisdom vs. artificial intelligence) 5. His framework for navigating midlife transitions and finding meaning after 40 6. Specific tactics for older professionals to thrive in tech companies 7. Surprising data that midlife is often the happiest time of life—and how to leverage your 40s, 50s, and beyond 8. Chip’s formula for managing anxiety and fear (and how to regain control when worry strikes) *Brought to you by:* Great Question—Empower everyone to run great research: https://www.greatquestion.com/lenny Vanta—Automate compliance. Simplify security: https://vanta.com/lenny Coda—The all-in-one collaborative workspace: https://coda.io/lenny *Transcript:* https://www.lennysnewsletter.com/p/chip-conley *My biggest takeaways (for paid newsletter subscribers):* https://www.lennysnewsletter.com/i/168435278/my-biggest-takeaways-from-this-conversation *Where to find Chip Conley:* • LinkedIn: https://www.linkedin.com/in/chipconleysf/ • Website: https://chipconley.com/ • Modern Elder Academy: https://www.meawisdom.com/ • Podcast: https://www.meawisdom.com/podcast/ *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 Chip Conley (04:30) Chip’s journey with Airbnb (11:44) Insights on working with Brian Chesky (18:27) Tactics to be effective when working with founders in founder mode (21:08) The value of intergenerational collaboration (27:03) Addressing ageism in tech (31:18) Advice for thriving as an older individual in tech (35:01) Advice for hiring managers (42:37) Chip’s early career and founding Joie de Vivre (44:12) A life-changing near-death experience (47:51) The importance of company culture (52:20) The Peak Model (57:09) The Modern Elder Academy (MEA) (01:00:30) The upside of aging (01:06:43) Who MEA is for (01:08:05) AI in daily life (01:10:20) Lightning round and final thoughts *Referenced:* • Brian Chesky on LinkedIn: https://www.linkedin.com/in/brianchesky/ • Brian Chesky’s new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach • Natalie Tucci on LinkedIn: https://www.linkedin.com/in/natalietuccishoff/ • Laura Modi on LinkedIn: https://www.linkedin.com/in/laurahughes6/ • How to build a cult-like brand | Laura Modi (Bobbie): https://www.lennysnewsletter.com/p/from-growth-to-slowth-the-making • George Tenet: https://en.wikipedia.org/wiki/George_Tenet • Joie de Vivre Hospitality: https://www.hyatt.com/jdv-by-hyatt/en-US • Fest300: https://en.wikipedia.org/wiki/Fest300 • John Q. Smith on LinkedIn: https://www.linkedin.com/in/johnqsmith/ •Will A.I. Replace New Hires or Middle Managers?: https://www.nytimes.com/2025/07/07/business/ai-job-cuts.html • Burning Man: https://burningman.org/ • Sheryl Sandberg on LinkedIn: https://www.linkedin.com/in/sheryl-sandberg-5126652/ • Bill Graham: https://en.wikipedia.org/wiki/Bill_Graham_(promoter) • Maslow’s hierarchy: https://en.wikipedia.org/wiki/Maslow%27s_hierarchy_of_needs • Measuring what makes life worthwhile: https://www.ted.com/talks/chip_conley_measuring_what_makes_life_worthwhile • Jonathan Mildenhall on LinkedIn: https://www.linkedin.com/in/mildenhall/ • Becca Levy’s website: https://becca-levy.com/ • Kabuki Springs & Spa: https://kabukisprings.com/ • How positive age beliefs can support positive health outcomes with Becca Levy, PhD: https://www.ama-assn.org/delivering-care/population-care/how-positive-age-beliefs-can-support-positive-health-outcomes-becca • The U-shape of Happiness Across the Life Course: Expanding the Discussion: https://pmc.ncbi.nlm.nih.gov/articles/PMC7529452/ ...References continued at: https://www.lennysnewsletter.com/p/chip-conley _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.

Bret Taylor’s legendary career includes being CTO of Meta, co-CEO of Salesforce, chairman of the board at OpenAI (yes, during that drama), co-creating both Google Maps and the Like button, and founding three companies. Today he’s the founder and CEO of Sierra, an AI agent company transforming customer service. He’s one of the few people I’ve met who’s been wildly successful at every level—from engineer to C-suite executive to founder—and across almost every discipline, including PM, engineer, CTO, COO, CPO, CEO, and board member. *In this conversation, you’ll learn:* 1. The brutal product review that nearly ended his Google career—and how that failure led to creating Google Maps 2. The question Sheryl Sandberg taught him to ask every morning (“What’s the most impactful thing I can do today?”) that transformed how he approached every role 3. The three AI market segments that matter 4. Why AI agents will replace SaaS products 5. His framework for knowing whose advice to actually listen to—and how that came in handy during the OpenAI board drama 6. The counterintuitive go-to-market strategy most AI startups get wrong 7. Sierra’s outcome-based pricing model that’s transforming how enterprise software is sold (and why every SaaS company should adopt it) 8. What he’s teaching his kids about AI that every parent should know *Brought to you by:* CodeRabbit—Cut code review time and bugs in half. Instantly: https://coderabbit.link/lenny Basecamp—The famously straightforward project management system from 37signals: https://www.basecamp.com/lenny Vanta—Automate compliance. Simplify security: https://vanta.com/lenny *Transcript:* https://www.lennysnewsletter.com/p/he-saved-openai-bret-taylor *My biggest takeaways (for paid newsletter subscribers):* https://www.lennysnewsletter.com/i/168905359/my-biggest-takeaways-from-this-conversation *Where to find Bret Taylor:* • X: https://x.com/btaylor • LinkedIn: https://www.linkedin.com/in/brettaylor/ *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 Bret Taylor (04:10) Bret’s early career and first major mistake (08:24) The birth of Google Maps (11:57) Lessons from FriendFeed and the importance of honest feedback (31:30) The future of coding and AI’s role (45:26) Preparing the next generation for an AI-driven world (48:46) AI in education (52:05) Business strategies in the AI market (01:04:38) Outcome-based pricing in AI (01:09:15) Productivity gains and AI (01:17:35) Go-to-market strategies for AI products (01:21:49) Lightning round and final thoughts *Referenced:* • Marissa Mayer on LinkedIn: https://www.linkedin.com/in/marissamayer/ • “Lazy Sunday”—SNL: https://www.youtube.com/watch?v=sRhTeaa_B98 • Quip: https://quip.com/ • Sierra: https://sierra.ai/ • FriendFeed: https://en.wikipedia.org/wiki/FriendFeed • Sheryl Sandberg on LinkedIn: https://www.linkedin.com/in/sheryl-sandberg-5126652/ • Jim Norris on LinkedIn: https://www.linkedin.com/in/halfspin/ • Paul Buchheit on X: https://x.com/paultoo • Sanjeev Singh on LinkedIn: https://www.linkedin.com/in/sanjeev-singh-20a1b72/ • Barack Obama: https://www.obamalibrary.gov/obamas/president-barack-obama • Oprah Winfrey: https://en.wikipedia.org/wiki/Oprah_Winfrey • Ashton Kutcher: https://en.wikipedia.org/wiki/Ashton_Kutcher • PayPal Mafia: https://en.wikipedia.org/wiki/PayPal_Mafia • Sam Altman on X: https://x.com/sama • Warren Buffett on X: https://x.com/warrenbuffett • Unix: https://en.wikipedia.org/wiki/Unix • Fortran: https://en.wikipedia.org/wiki/Fortran • C: https://en.wikipedia.org/wiki/C_(programming_language) • Python: https://www.python.org/ • Perl: https://www.perl.org/ • Rust: https://www.rust-lang.org/ • Eleven Labs: 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 • Confluent: https://www.confluent.io/ • Databricks: https://www.databricks.com/ • Snowflake: https://www.snowflake.com • Harvey: https://www.harvey.ai/ • Behind the founder: Marc Benioff: https://www.lennysnewsletter.com/p/behind-the-founder-marc-benioff • Larry Summers’s website: https://larrysummers.com/ • AutoCAD: https://www.autodesk.com/products/autocad/overview • Revit: https://www.autodesk.com/products/revit/ ...References continued at: https://www.lennysnewsletter.com/p/he-saved-openai-bret-taylor _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.

Madhavan Ramanujam is the world’s foremost expert on pricing and monetization strategy. As managing partner at Simon-Kucher, he helped over 250 companies, including 30 unicorns, architect their pricing strategies. He’s the author of the definitive book on pricing, Monetizing Innovation. Now he’s back with a sequel, Scaling Innovation, which reveals how to build enduring businesses by dominating both market share and wallet share. He recently left Simon-Kucher to launch his own fund, 49 Palms, focused on helping early-stage AI companies. *In this conversation, we discuss:* 1. The 2x2 framework that identifies your optimal pricing model 2. Why AI companies can capture 25% to 50% of value created, vs. 10% to 20% for traditional SaaS products 3. Why popular AI coding tools may have already doomed themselves with underpricing 4. The “give-and-get” framework top negotiators use to extract maximum value from every deal 5. The negotiation strategy that helped one founder 4x their deal size overnight 6. How to frame POCs as “business case creation” instead of technical demos (and why this changes everything) 7. Why AI companies must get monetization right from day one—not “figure it out later” 8. How companies like Intercom’s Fin and Sierra pioneered outcome-based pricing (charging $0.99 per AI resolution) 9. The single question that reveals if your pricing is too complex *Brought to you by:* Enterpret—Transform customer feedback into product growth: https://enterpret.com/lenny DX—A platform for measuring and improving developer productivity: https://getdx.com/lenny Persona—A global leader in digital identity verification: https://withpersona.com/lenny *Transcript:* https://www.lennysnewsletter.com/p/pricing-and-scaling-your-ai-product-madhavan-ramanujam *My biggest takeaways (for paid newsletter subscribers):* https://www.lennysnewsletter.com/i/168109183/my-biggest-takeaways-from-this-conversation *Where to find Madhavan Ramanujam:* • X: https://x.com/madhavansf • LinkedIn: https://www.linkedin.com/in/madhavansf/ • Promo email for Scaling Innovation: promo@49palmsvc.com — If you’re purchasing more than five copies, send a screenshot of your receipt to enter Madhavan’s exclusive bundle raffle. *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 Madhavan and his work (04:30) The core thesis of Scaling Innovation (09:20) Common traps founders fall into (12:06) Beautifully simple pricing (15:00) Mastering negotiations (26:51) Other strategies for effective pricing and monetization (27:35) How AI pricing is different (31:33) Handling POCs (36:25) The importance of mastering monetization (38:58) Choosing the right AI pricing model (43:13) Current trends in AI pricing (44:48) Strategizing for outcome-based models (50:23) Packaging strategies for scaling (51:37) Adapting pricing strategies over time (53:40) Key axioms for pricing success (58:00) Takeaways for founders (01:01:33) Lightning round and final thoughts *Referenced:* • The art and science of pricing | Madhavan Ramanujam (Monetizing Innovation, Simon-Kucher): https://www.lennysnewsletter.com/p/the-art-and-science-of-pricing-madhavan • Cursor: https://www.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 • Sierra Finn: http://www.sierrafinn.com/ • Chargeflow: https://www.chargeflow.io/ • GitHub: https://github.com/ • Intercom: https://www.intercom.com/ • Warren Buffett’s quote: https://www.goodreads.com/quotes/11478913-if-you-ve-got-the-power-to-raise-prices-without-losing • Sierra: https://sierra.ai/ • Clay Bavor on LinkedIn: https://www.linkedin.com/in/claybavor/ • Mission: Impossible—The Final Reckoning: https://www.imdb.com/title/tt9603208/ • Delphi: https://www.delphi.ai/ • Dara Ladjevardian on LinkedIn: https://www.linkedin.com/in/dara-ladjevardian/ • Sam Spelsberg on LinkedIn: https://www.linkedin.com/in/samuel-spelsberg/ • Lennybot: https://www.lennybot.com/ • Granola: https://www.granola.ai/ • Simon-Kucher: https://www.simon-kucher.com/ • Josh Bloom on LinkedIn: https://www.linkedin.com/in/joshuabloompricingconsulting/ *Recommended books:* • Monetizing Innovation: How Smart Companies Design the Product Around the Price: https://www.amazon.com/Monetizing-Innovation-Companies-Design-Product/dp/1119240867 • Scaling Innovation: How Smart Companies Architect Profitable Growth: https://www.amazon.com/dp/1119633060 ...References continued at: https://www.lennysnewsletter.com/p/pricing-and-scaling-your-ai-product-madhavan-ramanujam _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.

Benjamin Mann is a co-founder of Anthropic, an AI startup dedicated to building aligned, safety-first AI systems. Prior to Anthropic, Ben was one of the architects of GPT-3 at OpenAI. He left OpenAI driven by the mission to ensure that AI benefits humanity. In this episode, Ben opens up about the accelerating progress in AI and the urgent need to steer it responsibly. *In this conversation, we discuss:* 1. The inside story of leaving OpenAI with the entire safety team to start Anthropic 2. How Meta’s $100M offers reveal the true market price of top AI talent 3. Why AI progress is still accelerating (not plateauing), and how most people misjudge the exponential 4. Ben’s “economic Turing test” for knowing when we’ve achieved AGI—and why it’s likely coming by 2027-2028 5. Why he believes 20% unemployment is inevitable 6. The AI nightmare scenarios that concern him most—and how he believes we can still avoid them 7. How focusing on AI safety created Claude’s beloved personality 8. What three skills he’s teaching his kids instead of traditional academics *Brought to you by:* Sauce—Turn customer pain into product revenue: https://sauce.app/lenny LucidLink—Real-time cloud storage for teams: https://www.lucidlink.com/lenny Fin—The #1 AI agent for customer service: https://fin.ai/lenny *Transcript:* https://www.lennysnewsletter.com/p/anthropic-co-founder-benjamin-mann *My biggest takeaways (for paid newsletter subscribers):* https://www.lennysnewsletter.com/i/168107911/my-biggest-takeaways-from-this-conversation *Where to find Ben Mann:* • X: https://x.com/8enmann • LinkedIn: https://www.linkedin.com/in/benjamin-mann/ • Website: https://benjmann.net/ *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 Benjamin (04:43) The AI talent war (06:28) AI progress and scaling laws (10:50) Defining AGI and the economic Turing test (12:26) The impact of AI on jobs (17:45) Preparing for an AI future (24:05) Founding Anthropic (27:06) Balancing AI safety and progress (29:10) Constitutional AI and model alignment (34:21) The importance of AI safety (43:40) The risks of autonomous agents (45:40) Forecasting superintelligence (48:36) How hard is it to align AI? (53:19) Reinforcement learning from AI feedback (RLAIF) (57:03) AI's biggest bottlenecks (01:00:11) Personal reflections on responsibilities (01:02:36) Anthropic’s growth and innovations (01:07:48) Lightning round and final thoughts *Referenced:* • Dario Amodei on LinkedIn: https://www.linkedin.com/in/dario-amodei-3934934/ • Anthropic CEO: AI Could Wipe Out 50% of Entry-Level White Collar Jobs: https://www.marketingaiinstitute.com/blog/dario-amodei-ai-entry-level-jobs • Alexa+: https://www.amazon.com/dp/B0DCCNHWV5 • Azure: https://azure.microsoft.com/ • Sam Altman on X: https://x.com/sama • Opus 3: https://www.anthropic.com/news/claude-3-family • Claude’s Constitution: https://www.anthropic.com/news/claudes-constitution • Greg Brockman on X: https://x.com/gdb • Anthropic’s Responsible Scaling Policy: https://www.anthropic.com/news/anthropics-responsible-scaling-policy • Agentic Misalignment: How LLMs could be insider threats: https://www.anthropic.com/research/agentic-misalignment • Anthropic’s CPO on what comes next | Mike Krieger (co-founder of Instagram): https://www.lennysnewsletter.com/p/anthropics-cpo-heres-what-comes-next • 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 • Unitree: https://www.unitree.com/ • Arthur C. Clarke: https://en.wikipedia.org/wiki/Arthur_C._Clarke • How Reinforcement Learning from AI Feedback Works: https://www.assemblyai.com/blog/how-reinforcement-learning-from-ai-feedback-works • RLHF: https://en.wikipedia.org/wiki/Reinforcement_learning_from_human_feedback • Jared Kaplan on LinkedIn: https://www.linkedin.com/in/jared-kaplan-645843213/ • Moore’s law: https://en.wikipedia.org/wiki/Moore%27s_law • Machine Intelligence Research Institute: https://intelligence.org/ • Raph Lee on LinkedIn: https://www.linkedin.com/in/raphaeltlee/ • “The Last Question”: https://en.wikipedia.org/wiki/The_Last_Question • Beth Barnes on LinkedIn: https://www.linkedin.com/in/elizabethmbarnes/ • “The Last Question”: https://en.wikipedia.org/wiki/The_Last_Question • Good Strategy, Bad Strategy | Richard Rumelt: https://www.lennysnewsletter.com/p/good-strategy-bad-strategy-richard • Pantheon on Netflix: https://www.netflix.com/title/81937398 *...References continued at:* https://www.lennysnewsletter.com/p/anthropic-co-founder-benjamin-mann _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.

Dan Shipper is the co-founder and CEO of Every. With just 15 people, Every publishes a daily AI newsletter, ships multiple AI products, and operates a million-dollar-a-year consulting arm—all while their engineers write virtually zero code. It’s the most radical example of AI-first operations, and Dan is a prolific writer who has become a leading voice on how AI is transforming the way we build and work. *Learn:* 1. Why Dan thinks AI won’t steal jobs en masse—and may actually reshore many jobs to the U.S. 2. The most underrated AI tool for non-programmers 3. An inside look at Every’s AI-first workflow 4. Why every company needs an “AI operations lead” 5. How Dan’s team uses an arsenal of AI agents (Claude, Codex, “Friday,” “Charlie”) in parallel, treating each AI like a specialist with unique strengths 6. Why generalists will thrive in an AI-first world, as rigid job titles blur and everyone becomes a “manager” of AI tools 7. Dan’s playbook for making any company AI-first—from the CEO setting the example, to hosting internal prompt-sharing sessions, to upskilling teams on AI tools *Brought to you by:* CodeRabbit—Cut code review time and bugs in half. Instantly: https://coderabbit.link/lenny DX—A platform for measuring and improving developer productivity: https://getdx.com/lenny PostHog—How developers build successful products: https://posthog.com/lenny *Transcript:* https://www.lennysnewsletter.com/p/inside-every-dan-shipper *My biggest takeaways (for paid newsletter subscribers):* https://www.lennysnewsletter.com/i/167681269/my-biggest-takeaways-from-this-conversation *Where to find Dan Shipper:* • X: https://x.com/danshipper • LinkedIn: https://www.linkedin.com/in/danshipper/ • Podcast: https://every.to/podcast *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) Welcome and introduction (04:04) Hot takes on AI and job reshoring (07:06) The power of Claude Code for non-coders (14:35) The future of AI in business operations (18:45) AI’s role in enhancing human skills (22:26) The evolution of AI tools and their applications (25:40) Building an AI-first company (29:50) Innovative AI operations and team dynamics (35:35) Dan's AI stack (41:26) Compounding engineering (48:29) The impact of AI on learning and development (50:10) Accelerating career growth with AI (51:36) Revolutionizing code review and workflow (53:07) The importance of coding knowledge (57:26) Building AI-driven products (01:02:01) Innovative fundraising strategies (01:08:45) Consulting and AI adoption in companies (01:17:01) The allocation economy and future skills (01:20:12) The value of generalists in the AI age (01:24:07) Lightning round and final thoughts *Referenced:* • Claude Code: https://www.anthropic.com/claude-code • Gemini CLI: https://blog.google/technology/developers/introducing-gemini-cli-open-source-ai-agent/ • Microsoft Copilot: https://copilot.microsoft.com/ • Cursor: https://www.cursor.com/ • 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 • 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 • Plato’s Argument Against Writing: https://fs.blog/an-old-argument-against-writing/ • 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 • Granola: https://www.granola.ai/ • Tobi Lutke’s post on X about context engineering: https://x.com/tobi/status/1935533422589399127 • 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 • Every: https://every.to/ • Cora: https://www.cora.computer/ • Sparkle: https://makeitsparkle.co/ • Spiral: https://spiral.computer/ • Lex: https://lex.page/ • Nathan Baschez on LinkedIn: https://www.linkedin.com/in/nbashaw/ • Kate Lee on LinkedIn: https://www.linkedin.com/in/kate-lee-506768/ • Katie Parrott on LinkedIn: https://www.linkedin.com/in/katieparrott/ • Animalz: https://www.animalz.co/ • Rachel Woods on X: https://x.com/rachel_l_woods • Nityesh Agarwal on LinkedIn: https://www.linkedin.com/in/nityeshaga • Claude Opus 4: https://www.anthropic.com/claude/opus *...References continued at:* https://www.lennysnewsletter.com/p/inside-every-dan-shipper _Production and marketing by https://penname.co/._ _For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com._ Lenny may be an investor in the companies discussed.

Jake Knapp and John Zeratsky are the co-creators of the Design Sprint (the famous five-day product innovation process) and authors of the bestselling book Sprint. After decades of working with over 300 startups in the earliest stages, they discovered that most startups fail not because they can’t build, but because they build the wrong thing. The very beginning of a startup is your highest-leverage moment, and most teams waste months or years by skipping a few critical early questions. Jake and John developed the Foundation Sprint to help startups validate ideas and compress months of work into just two days. *What you’ll learn:* 1. The step-by-step Foundation Sprint process that compresses three or four months of validation into two days—including templates you can use immediately 2. Why differentiation is the #1 predictor of startup success (with the 2x2 framework that you can use with your team) 3. The three fundamental questions every founder should answer before writing a line of code 4. The “note and vote” technique that eliminates groupthink and gets honest answers from your colleagues 5. The seven “magic lenses” for choosing between multiple product ideas 6. The biggest mistake engineers make when building with AI tools 7. The paradox of speed: why “building nothing first” can get you to product-market fit faster *Brought to you by:* Brex—The banking solution for startups: https://www.brex.com/product/business-account?ref_code=bmk_dp_brand1H25_ln_new_fs Paragon—Ship every SaaS integration your customers want: https://www.useparagon.com/lenny Coda—The all-in-one collaborative workspace: https://coda.io/lenny *Transcript:* https://www.lennysnewsletter.com/p/the-foundation-sprint-jake-knapp-and-john-zeratsky *My biggest takeaways (for paid newsletter subscribers):* https://www.lennysnewsletter.com/i/167485876/my-biggest-takeaways-from-this-conversation *Where to find Jake Knapp:* • X: https://twitter.com/jakek • LinkedIn: https://www.linkedin.com/in/jake-knapp/ • Website: https://jakeknapp.com/ *Where to find John Zeratsky:* • X: https://twitter.com/jazer • LinkedIn: https://www.linkedin.com/in/johnzeratsky/ • Website: https://johnzeratsky.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 Jake Knapp and John Zeratsky (04:41) Origins of the Design Sprint (11:06) The Foundation Sprint process (14:40) Phase one: The basics (16:57) Case study: Latchet (28:50) Phase two: Differentiation (36:24) The importance of differentiation (40:15) Thoughts on price differentiation (43:37) Case study: Mellow (46:04) Custom differentiators (49:30) The mini manifesto (52:02) Phase three: Approach to the project (54:50) Magic lenses activity (01:02:39) Prototyping and testing (01:10:00) Real-world examples and success stories (01:15:15) Motivation behind The Foundation Sprint (01:17:15) The outcome of the sprint: The founding hypothesis (01:19:28) The Design Sprint (01:28:19) The role of AI in prototyping (01:36:50) Final thoughts and resources *Referenced:* • Introducing the Foundation Sprint: From the creators of the Design Sprint: https://www.lennysnewsletter.com/p/introducing-the-foundation-sprint • Making time for what matters | Jake Knapp and John Zeratsky (authors of Sprint and Make Time, co-founders of Character Capital): https://www.lennysnewsletter.com/p/making-time-for-what-matters-jake • Eli Blee-Goldman on LinkedIn: https://www.linkedin.com/in/eli-blee-goldman/ • Character Capital: https://www.character.vc/ • Character Labs: https://www.character.vc/labs • Etsy: https://www.etsy.com/ • Shopify: https://www.shopify.com/ • Naming expert shares the process behind creating billion-dollar brand names like Azure, Vercel, Windsurf, Sonos, Blackberry, and Impossible Burger | David Placek (Lexicon Branding): https://www.lennysnewsletter.com/p/naming-expert-david-placek • Sonos: https://www.sonos.com/ • Vercel: https://vercel.com/ • Windsurf: https://windsurf.com/ • April Dunford on product positioning, segmentation, and optimizing your sales process: https://www.lennysnewsletter.com/p/april-dunford-on-product-positioning • Positioning: https://www.lennysnewsletter.com/p/positioning ...References continued at: https://www.lennysnewsletter.com/p/the-foundation-sprint-jake-knapp-and-john-zeratsky *Recommended books:* • Sprint: How to Solve Big Problems and Test New Ideas in Just Five Days: https://www.amazon.com/Sprint-audiobook/dp/B019R2DQIY • Make Time: How to Focus on What Matters Every Day: https://www.amazon.com/Make-Time-Focus-Matters-Every/dp/0525572422 • Click: How to Make What People Want: https://www.amazon.com/Click-Make-What-People-Want/dp/1668072114 _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.

Andrew Wilkinson is the co‑founder of Tiny, a holding company that quietly owns more than three dozen profitable internet and consumer brands, including Dribbble and the AeroPress coffee maker. Starting as a teenage barista and web designer, he’s created a portfolio approaching $300 million in yearly sales (and he was personally worth over $1 billion at one point)—all without ever raising venture capital. *In this conversation, you’ll learn:* 1. The “fish where the fish are” framework for spotting high‑margin niches no one else notices 2. The exact agent stack (Lindy, Replit, Limitless, and more) that supercharges Andrew’s day-to-day productivity (and has replaced his assistant) 3. How Andrew evaluates companies in less than 15 minutes using Buffett‑style moats and “lazy leadership” 4. Telltale signs you should shut down (or never start) that startup idea 5. His journey from crippling anxiety to clarity through SSRIs and ADHD medication 6. His prediction that most knowledge work will be automated—and the skills to teach your kids now *Transcript:* https://www.lennysnewsletter.com/p/ive-run-75-businesses-andrew-wilkinson *Brought to you by:* Sauce—Turn customer pain into product revenue: http://sauce.app/lenny Enterpret—Transform customer feedback into product growth: https://enterpret.com/lenny Miro—A collaborative visual platform where your best work comes to life: https://miro.com/lenny *Where to find Andrew Wilkinson:* • X: https://x.com/awilkinson • LinkedIn: https://www.linkedin.com/in/awilkinson/ *Where to find Lenny:* • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ *In this episode, we cover:* (00:00) Introduction to Andrew Wilkinson (04:07) Finding the right business idea (07:18) Avoiding common business pitfalls (11:58) Finding your unfair advantage (17:08) Fish where the fish are (20:08) Why boring is good (25:30) Bootstrapping vs. venture capital (31:20) Lessons from acquiring and managing businesses (36:47) Avoiding people problems (42:39) Leveraging AI in business and life (49:30) The Limitless device (53:13) Job displacement and AI’s future impact (58:20) Advice for new grads (01:02:50) Parenting in the age of AI (01:05:26) The pursuit of happiness beyond wealth (01:10:10) Mental health and medication (01:16:45) Lightning round and final thoughts *Referenced:* • Andrew’s post on X with the Charlie Munger quote: https://x.com/awilkinson/status/1265653805443506182 • Metalab: https://www.metalab.com/ • Letterboxd: https://letterboxd.com/ • AeroPress: https://aeropress.com/ • Brian Armstrong on X: https://x.com/brian_armstrong • Warren Buffett’s quote: https://quotefancy.com/quote/931119/Warren-Buffett-I-am-a-better-investor-because-I-am-a-businessman-and-a-better-businessman • Flow: https://www.getflow.com/ • Instacart: https://www.instacart.com/ • Things: https://culturedcode.com/things/ • Dustin Moskovitz on LinkedIn: https://www.linkedin.com/in/dmoskov/ • Salesforce: https://www.salesforce.com/ • Serato: https://serato.com/ • Chris Sparling on X: https://x.com/_sparling_ • Lindy: https://www.lindy.ai/ • 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 • David Ogilvy: https://en.wikipedia.org/wiki/David_Ogilvy_(businessman) • Malcolm Gladwell’s website: https://www.gladwellbooks.com/ • 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 • Building Lovable: $10M ARR in 60 days with 15 people | Anton Osika (CEO and co-founder): https://www.lennysnewsletter.com/p/building-lovable-anton-osika • Limitless: https://www.limitless.ai/ • Perplexity: https://www.perplexity.ai/ • Claude: https://claude.ai/ • ChatGPT: https://chatgpt.com/ • Gemini: https://gemini.google.com/app • William Gibson’s quote: https://www.goodreads.com/quotes/681-the-future-is-already-here-it-s-just-not-evenly • Palm Treo: https://en.wikipedia.org/wiki/Palm_Treo ...References continued at: https://www.lennysnewsletter.com/p/ive-run-75-businesses-andrew-wilkinson *Recommended books:* • The Laws of Human Nature: https://www.amazon.com/Laws-Human-Nature-Robert-Greene/dp/0525428143 • How to Get Rich: One of the World’s Greatest Entrepreneurs Shares His Secrets: https://www.amazon.com/How-Get-Rich-Greatest-Entrepreneurs/dp/1591842719 _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.

David Placek is the founder of Lexicon Branding, a company that focuses exclusively on the development of brand names for competitive advantage. Lexicon is behind iconic names such as Sonos, Microsoft’s Azure, Windsurf, Vercel, Impossible Foods, BlackBerry, Intel’s Pentium, Apple’s PowerBook, and Swiffer. Over 40 years, David’s team has named nearly 4,000 brands and companies, employing over 250 linguists and pioneering naming innovation. *What you’ll learn:* 1. The three-step process that generated names like Windsurf and Vercel 2. How a name can give you the edge that no marketing budget can buy 3. Why you won’t “know it when you see it” 4. Why Microsoft called Azure “a dumb name” before it became their billion-dollar cloud platform 5. Why polarizing opinions are the strongest signal that you’ve found the right name 6. How every letter of the alphabet creates a specific psychological vibration 7. The diamond framework: a 4-step process any founder can use to find their perfect name 8. Why domain names don’t matter anymore in the age of AI *Transcript:* ⁠https://www.lennysnewsletter.com/p/naming-expert-david-placek *Brought to you by:* WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs: https://workos.com/lenny Stripe—Helping companies of all sizes grow revenue: https://stripe.com/ OneSchema—Import CSV data 10x faster: https://oneschema.co/lenny *Where to find David Placek:* • LinkedIn: https://www.linkedin.com/in/david-placek-05a82/ • Website: https://www.lexiconbranding.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 David and Lexicon Branding (04:44) The story of Sonos (09:27) The psychology of naming (11:33) The initial resistance to Microsoft's Azure (14:35) The importance of a great brand name (18:11) The three steps of naming: create, invent, implement (28:23) Qualities of great brand name creators (31:24) How long the naming process takes (32:12) The Windsurf case study (36:10) Naming in the AI era (39:37) When to change your name (43:10) The role of linguists (45:54) The power of letters in branding (48:15) The Vercel case study (50:12) The implementation phase (52:52) Client management and market success (55:16) The diamond exercise (01:04:23) Suspending judgment (01:07:31) Polarization and boldness (01:11:01) Domain names (01:12:48) Final thoughts and lightning round *Referenced:* • PowerBook: https://en.wikipedia.org/wiki/PowerBook • Pentium: https://en.wikipedia.org/wiki/Pentium • BlackBerry: https://en.wikipedia.org/wiki/BlackBerry • Swiffer: https://www.swiffer.com/ • Impossible Burger: https://impossiblefoods.com/ • Vercel: https://vercel.com/ • Windsurf: https://windsurf.com/ • CapCut: https://www.capcut.com/ • Azure: https://azure.microsoft.com/ • Sonos: https://www.sonos.com/ • John MacFarlane on LinkedIn: https://www.linkedin.com/in/john-macfarlane-08a8aa20/ • Harry Potter: https://en.wikipedia.org/wiki/Harry_Potter_(film_series) • The Call of the Wild: https://en.wikipedia.org/wiki/The_Call_of_the_Wild • 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 • Sound symbolism: https://en.wikipedia.org/wiki/Sound_symbolism • Anduril: https://www.anduril.com/ • Anthropic: https://www.anthropic.com/ • 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 • 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 • Building a magical AI code editor used by over 1 million developers in four months: The untold story of Windsurf | Varun Mohan (co-founder and CEO): https://www.lennysnewsletter.com/p/the-untold-story-of-windsurf-varun-mohan • Y Combinator: https://www.ycombinator.com/ • Chevrolet Corvette: https://en.wikipedia.org/wiki/Chevrolet_Corvette • Viagra: https://www.viagra.com/ • In vino veritas: https://en.wikipedia.org/wiki/In_vino_veritas • Infoseek: https://en.wikipedia.org/wiki/Infoseek • Andy Grove: https://en.wikipedia.org/wiki/Andrew_Grove • Churchill at War on Netflix: https://www.netflix.com/title/81609374 ...References continued at: https://www.lennysnewsletter.com/p/naming-expert-david-placek _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.

Peter Deng has led product teams at OpenAI, Instagram, Uber, Facebook, Airtable, and Oculus and helped build products used by billions—including Facebook’s News Feed, the standalone Messenger app, Instagram filters, Uber Reserve, ChatGPT, and more. Currently he’s investing in early-stage founders at Felicis. In this episode, Peter dives into his most valuable lessons from building and scaling some of tech’s most iconic products and companies. *What you’ll learn:* 1. Peter’s one‑sentence test for hiring superstars 2. Why your product (probably) doesn’t matter 3. Why you don’t need a tech breakthrough to build a huge business 4. The five PM archetypes, and how to build a team of Avengers 5. Counterintuitive lessons on growing products from 0 to 1, and 1 to 100 6. The importance of data flywheels and workflows *Transcript:* https://www.lennysnewsletter.com/p/the-quiet-architect-peter-deng *Brought to you by:* Paragon—Ship every SaaS integration your customers want: https://www.useparagon.com/lenny Pragmatic Institute—Industry‑recognized product, marketing, and AI training and certifications: https://pragmaticinstitute.com/lenny Contentsquare—Create better digital experiences: https://contentsquare.com/lenny/ *Where to find Peter Deng:* • X: https://x.com/pxd • LinkedIn: https://www.linkedin.com/in/peterxdeng/ *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 Peter Deng (05:41) AI and AGI insights (11:35) The future of education with AI (16:53) The power of language in leadership (21:01) Building iconic products (36:44) Scaling from zero to 100 (41:56) Balancing short- and long-term goals (47:12) Creating a healthy tension in teams (50:02) The five archetypes of product managers (55:39) Primary and secondary archetypes (58:47) Hiring for growth mindset and autonomy (01:15:52) Effective management and communication strategies (01:19:23) Presentation advice and self-advocacy (01:25:50) Balancing craft and practicality in product management (01:30:40) The importance of empathy in design thinking (01:35:45) Career decisions and learning opportunities (01:42:05) Lessons from product failures (01:45:42) Lightning round and final thoughts *Referenced:* • OpenAI: https://openai.com/ • Artificial general intelligence (AGI): https://en.wikipedia.org/wiki/Artificial_general_intelligence • Head of ChatGPT answers philosophical questions about AI at SXSW 2024 with SignalFire’s Josh Constine: https://www.youtube.com/watch?v=mgbgI0R6XCw • Professors Are Using A.I., Too. Now What?: https://www.npr.org/2025/05/21/1252663599/kashmir-hill-ai#:~:text=Now%20What • Herbert H. Clark: https://web.stanford.edu/~clark/ • Russian speakers get the blues: https://www.newscientist.com/article/dn11759-russian-speakers-get-the-blues/ • Ilya Sutskever (OpenAI Chief Scientist)—Building AGI, Alignment, Future Models, Spies, Microsoft, Taiwan, & Enlightenment: https://www.dwarkesh.com/p/ilya-sutskever • Anthropic’s CPO on what comes next | Mike Krieger (co-founder of Instagram): https://www.lennysnewsletter.com/p/anthropics-cpo-heres-what-comes-next • Kevin Systrom on LinkedIn: https://www.linkedin.com/in/kevinsystrom/ • Building a magical AI code editor used by over 1 million developers in four months: The untold story of Windsurf | Varun Mohan (co-founder and CEO): https://www.lennysnewsletter.com/p/the-untold-story-of-windsurf-varun-mohan • Microsoft CPO: If you aren’t prototyping with AI, you’re doing it wrong | Aparna Chennapragada: https://www.lennysnewsletter.com/p/microsoft-cpo-on-ai • 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 • Building Lovable: $10M ARR in 60 days with 15 people | Anton Osika (CEO and co-founder): https://www.lennysnewsletter.com/p/building-lovable-anton-osika • Granola: https://www.granola.ai/ • 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 • 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 • Fidji Simo on LinkedIn: https://www.linkedin.com/in/fidjisimo/ • Airtable: https://www.airtable.com/ • George Lee on LinkedIn: https://www.linkedin.com/in/geolee/ • Andrew Chen on LinkedIn: https://www.linkedin.com/in/andrewchen/ ...References continued at: https://www.lennysnewsletter.com/p/the-quiet-architect-peter-deng _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.

Mike Krieger is the chief product officer of Anthropic and the co-founder of Instagram. After leaving Meta, he co-founded Artifact, an AI-powered news app that I absolutely loved, and joined Anthropic to lead product in 2024. *In this episode, you'll learn:* 1. How Anthropic uses AI to write 90-95% of code for some products and the surprising new bottlenecks this creates 2. Why embedding product managers with AI researchers yields 10x the impact of traditional product development 3. The three areas where product teams can still add massive value as AI gets smarter 4. How Anthropic plans to compete with OpenAI long-term 5. How to use Claude as your product strategy partner (with specific prompting techniques) 6. Why Mike shut down Artifact despite loving the product, and what founders can learn from it 7. Where AI startups should build to avoid getting killed by OpenAI, Anthropic, and Google 8. Why MCP (Model Context Protocol) might reshape how all software works 9. The counterintuitive product metrics that matter for AI 10. How to evaluate whether your company is maximizing AI’s potential or just scratching the surface *Transcript:* https://www.lennysnewsletter.com/p/anthropics-cpo-heres-what-comes-next *Brought to you by:* Productboard—Make products that matter: https://www.productboard.com/lenny Stripe—Helping companies of all sizes grow revenue: https://stripe.com/ OneSchema—Import CSV data 10x faster: https://oneschema.co/lenny *Where to find Mike Krieger:* • X: https://x.com/mikeyk • LinkedIn: https://www.linkedin.com/in/mikekrieger/ *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 Mike Krieger (04:25) What Mike has changed his mind about regarding AI capabilities (07:43) How to avoid scary AI scenarios (09:00) Skills kids will need in an AI world (11:58) How product development changes when 90% of code is written by AI (17:12) Claude helping with product strategy (21:21) A new way of working (24:00) The future value of product teams in an AI world (27:23) Prompting tricks to get more out of Claude (29:57) The Rick Rubin collaboration on “vibe coding” (32:47) How Mike was recruited to Anthropic (36:00) Why Mike shut down Artifact (42:46) Anthropic vs. OpenAI (47:16) Where AI founders should play to avoid getting squashed (52:03) How companies can best leverage Anthropic’s models and APIs (54:34) The role of MCPs (Model Context Protocols) (58:30) Claude’s questions for Mike (01:03:20) Claude’s heartfelt message to Mike *Referenced:* • Anthropic: https://www.anthropic.com/ • Claude Opus 4: https://www.anthropic.com/claude/opus • Dario Amodei on X: https://x.com/darioamodei • AI 2027: https://ai-2027.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 • Claude Shannon: https://en.wikipedia.org/wiki/Claude_Shannon • Information theory: https://en.wikipedia.org/wiki/Information_theory • TypeScript: https://www.typescriptlang.org/ • Python: https://www.python.org/ • Rust: https://www.rust-lang.org/ • Bending the universe in your favor | Claire Vo (LaunchDarkly, Color, Optimizely, ChatPRD): https://www.lennysnewsletter.com/p/bending-the-universe-in-your-favor • Announcing a brand-new podcast: “How I AI” with Claire Vo: https://www.lennysnewsletter.com/p/announcing-a-brand-new-podcast-how • A conversation with OpenAI’s CPO Kevin Weil, Anthropic’s CPO Mike Krieger, and Sarah Guo: https://www.youtube.com/watch?v=IxkvVZua28k • Jack Clark on LinkedIn: https://www.linkedin.com/in/jack-clark-5a320317/ • Artifact: https://en.wikipedia.org/wiki/Artifact_(app) • Joel Lewenstein on LinkedIn: https://www.linkedin.com/in/joel-lewenstein/ • Daniela Amodei on LinkedIn: https://www.linkedin.com/in/daniela-amodei-790bb22a/ • Boris Cherny on LinkedIn: https://www.linkedin.com/in/bcherny/ • Gunnar Gray on LinkedIn: https://www.linkedin.com/in/gunnargray/ • The Model Context Protocol: https://www.anthropic.com/news/model-context-protocol ...References continued at: https://www.lennysnewsletter.com/p/anthropics-cpo-heres-what-comes-next *Recommended books:* • The Goal: A Process of Ongoing Improvement: https://www.amazon.com/Goal-Process-Ongoing-Improvement/dp/0884271951 • The Way of the Code: The Timeless Art of Vibe Coding: https://www.thewayofcode.com/ • The Hard Thing About Hard Things: Building a Business when There Are No Easy Answers―Straight Talk on the Challenges of Entrepreneurship: https://www.amazon.com/Hard-Thing-About-Things-Building/dp/0062273205 _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.

*Nabeel Qureshi* is an entrepreneur, writer, researcher, and visiting scholar of AI policy at the Mercatus Center (alongside Tyler Cowen). Previously, he spent nearly eight years at Palantir, working as a forward-deployed engineer. His work at Palantir ranged from accelerating the Covid-19 response to applying AI to drug discovery to optimizing aircraft manufacturing at Airbus. Nabeel was also a founding employee and VP of business development at GoCardless, a leading European fintech unicorn. *What you’ll learn:* 1. Why almost a third of all Palantir’s PMs go on to start companies 2. How the “forward-deployed engineer” model works and why it creates exceptional product leaders 3. How Palantir transformed from a “sparkling Accenture” into a $200 billion data/software platform company with more than 80% margins 4. The unconventional hiring approach that screens for independent-minded, intellectually curious, and highly competitive people 5. Why the company intentionally avoids traditional titles and career ladders—and what they do instead 6. Why they built an ontology-first data platform that LLMs love 7. How Palantir’s controversial “bat signal” recruiting strategy filtered for specific talent types 8. The moral case for working at a company like Palantir *Transcript:* https://www.lennysnewsletter.com/p/inside-palantir-nabeel-qureshi *Brought to you by:* • WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs: https://workos.com/lenny • Attio—The powerful, flexible CRM for fast-growing startups: https://attio.com/lenny?utm_source=lennyrachitsky&utm_medium=sponsorship&utm_campaign=lenny-20230625 • OneSchema—Import CSV data 10x faster: https://oneschema.co/lenny *Where to find Nabeel S. Qureshi:* • X: https://x.com/nabeelqu • LinkedIn: https://www.linkedin.com/in/nabeelqu/ • Website: https://nabeelqu.co/ *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 Nabeel S. Qureshi (05:10) Palantir’s unique culture and hiring (13:29) What Palantir looks for in people (16:14) Why they don't have titles (19:11) Forward-deployed engineers at Palantir (25:23) Key principles of Palantir's success (30:00) Gotham and Foundry (36:58) The ontology concept (38:02) Life as a forward-deployed engineer (41:36) Balancing custom solutions and product vision (46:36) Advice on how to implement forward-deployed engineers (50:41) The current state of forward-deployed engineers at Palantir (53:15) The power of ingesting, cleaning and analyzing data (59:25) Hiring for mission-driven startups (01:05:30) What makes Palantir PMs different (01:10:00) The moral question of Palantir (01:16:03) Advice for new startups (01:21:12) AI corner (01:24:00) Contrarian corner (01:25:42) Lightning round and final thoughts *Referenced:* • Reflections on Palantir: https://nabeelqu.co/reflections-on-palantir • Palantir: https://www.palantir.com/ • Intercom: https://www.intercom.com/ • Which companies produce the best product managers: https://www.lennysnewsletter.com/p/which-companies-produce-the-best • Gotham: https://www.palantir.com/platforms/gotham/ • Foundry: https://www.palantir.com/platforms/foundry/ • Peter Thiel on X: https://x.com/peterthiel • Alex Karp: https://en.wikipedia.org/wiki/Alex_Karp • Stephen Cohen: https://en.wikipedia.org/wiki/Stephen_Cohen_(entrepreneur) • Joe Lonsdale on LinkedIn: https://www.linkedin.com/in/jtlonsdale/ • Tyler Cowen’s website: https://tylercowen.com/ • This Scandinavian City Just Won the Internet With Its Hilarious New Tourism Ad: https://www.afar.com/magazine/oslos-new-tourism-ad-becomes-viral-hit • Safe Superintelligence: https://ssi.inc/ • Mira Murati on X: https://x.com/miramurati • Stripe: https://stripe.com/ • Building product at Stripe: craft, metrics, and customer obsession | Jeff Weinstein (Product lead): https://www.lennysnewsletter.com/p/building-product-at-stripe-jeff-weinstein • Airbus: https://www.airbus.com/en • NIH: https://www.nih.gov/ • Jupyter Notebooks: https://jupyter.org/ • Shyam Sankar on LinkedIn: https://www.linkedin.com/in/shyamsankar/ • Palantir Gotham for Defense Decision Making: https://www.youtube.com/watch?v=rxKghrZU5w8 • Foundry 2022 Operating System Demo: https://www.youtube.com/watch?v=uF-GSj-Exms • SQL: https://en.wikipedia.org/wiki/SQL • Airbus A350: https://en.wikipedia.org/wiki/Airbus_A350 • SAP: https://www.sap.com/index.html • Barry McCardel on LinkedIn: https://www.linkedin.com/in/barrymccardel/ ...References continued at: https://www.lennysnewsletter.com/p/inside-palantir-nabeel-qureshi _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.

Annie Duke is a former professional poker player, a decision-making expert, and a special partner at First Round Capital. She is the author of Thinking in Bets (a national bestseller) and Quit: The Power of Knowing When to Walk Away and the co-founder of the Alliance for Decision Education, a nonprofit whose mission is to improve lives by empowering students through decision skills education. In our conversation, we cover: • What Annie learned from the late Daniel Kahneman • The power of pre-mortems and “kill criteria” • The relationship between money and happiness • The power of “mental time travel” • The nominal group technique for better decision quality • How First Round Capital improved their decision-making process • Many tactical decision-making frameworks — Brought to you by: • Vanta—Automate compliance. Simplify security: https://vanta.com/lenny • UserTesting—Human understanding. Human experiences: https://www.usertesting.com/lenny • LinkedIn Ads—Reach professionals and drive results for your business: https://www.linkedin.com/podlenny Find the transcript at: https://www.lennysnewsletter.com/p/making-better-decisions-annie-duke Where to find Annie Duke: • X: https://twitter.com/AnnieDuke • LinkedIn: https://www.linkedin.com/in/annie-duke/ • Website: https://www.annieduke.com/ • Substack: https://www.annieduke.com/substack/ 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) Annie’s background (03:53) Lessons from Daniel Kahneman: humility, curiosity, and open-mindedness (09:15) The importance of unconditional love in parenting (15:15) Mental time travel and “nevertheless” (20:06) The extent of improvement possible in decision-making (24:54) Independent brainstorming for better decisions (35:36) Making sure people feel heard (42:41) The “3Ds” framework to make better decisions (44:49) Decision quality (55:46) Improving decision-making at First Round Capital (01:05:05) Using pre-mortems and kill criteria (01:10:15) Making explicit what’s implicit (01:10:55) The challenges of quitting and knowing when to walk away (01:19:23) Where to find Annie Referenced: • Daniel Kahneman, Who Plumbed the Psychology of Economics, Dies at 90: https://www.nytimes.com/2024/03/27/business/daniel-kahneman-dead.html • Adversarial collaboration: https://en.wikipedia.org/wiki/Adversarial_collaboration • Does more money correlate with greater happiness?: https://penntoday.upenn.edu/news/does-more-money-correlate-greater-happiness-Penn-Princeton-research# • Income and emotional well-being: A conflict resolved: https://pubmed.ncbi.nlm.nih.gov/36857342/ • Strategic decisions: When can you trust your gut?: https://www.mckinsey.com/capabilities/strategy-and-corporate-finance/our-insights/strategic-decisions-when-can-you-trust-your-gut • Cass Sunstein on X: https://twitter.com/CassSunstein • Dr. Becky on Instagram: https://www.instagram.com/drbeckyatgoodinside • A framework for finding product-market fit | Todd Jackson (First Round Capital): https://www.lennysnewsletter.com/p/a-framework-for-finding-product-market • First Round Capital: https://firstround.com/ • Brett Berson on X: https://twitter.com/brettberson • Renegade Partners: https://www.renegadepartners.com/ • Renata Quintini on X: https://twitter.com/rquintini • Roseanne Wincek on X: https://twitter.com/imthemusic • Josh Kopelman on X: https://twitter.com/joshk • Bill Trenchard on X: https://twitter.com/btrenchard • Linnea Gandhi on X: https://twitter.com/linneagandhi • Maurice Schweitzer on X: https://twitter.com/me_schweitzer • Create a Solid Plan on How to Fail Big This Year: https://www.forbes.com/sites/forbesfinancecouncil/2020/02/07/create-a-solid-plan-on-how-to-fail-big-this-year/ • Quit: The Power of Knowing When to Walk Away: https://www.amazon.com/Quit-Power-Knowing-When-Walk/dp/0593422996/ • Richard Thaler on X: https://twitter.com/R_Thaler • Stewart Butterfield on X: https://twitter.com/stewart • Glitch: https://en.wikipedia.org/wiki/Glitch_(video_game) • How the Founder of Slack & Flickr Turned Colossal Failures into Billion-Dollar Companies: https://medium.com/swlh/how-the-founder-of-slack-flickr-turned-failures-into-million-and-billion-dollar-companies-7bcaf0d35d66 • The Most Fascinating Profile You’ll Ever Read About a Guy and His Boring Startup: https://www.wired.com/2014/08/the-most-fascinating-profile-youll-ever-read-about-a-guy-and-his-boring-startup/ • The Alliance for Decision Education: https://alliancefordecisioneducation.org/ • Make Better Decisions course on Maven: https://maven.com/annie-duke/make-better-decisions 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.

Claire Vo is the chief product officer at LaunchDarkly and the founder of ChatPRD, likely the most popular PM-specific AI product out there. Before LaunchDarkly, she was a longtime chief product officer at Color and Optimizely. Claire has founded and managed two other companies, Pretty HQ and Experiment Engine, the latter of which Optimizely acquired in 2017. In our conversation, we discuss: • Knowing what you want in your career and being clear about it • Finding your zone of genius and how to operate within it • How to maintain a fast pace in larger companies • How to make it easy for your boss to help you achieve your goals • Advice for navigating the tech industry as a woman • The role of a CPTO and the benefits it brings to organizations • Why she built ChatPRD • Tips for building your own AI tools • The impact of AI on product management and what skills will continue to be important — Brought to you by: • Orb—The flexible billing engine for modern pricing: https://www.withorb.com/lenny • Dovetail—Bring your customer into every decision: https://dovetailapp.com/lenny • Vanta—Automate compliance. Simplify security: https://vanta.com/lenny Find the full transcript at: https://www.lennysnewsletter.com/p/bending-the-universe-in-your-favor Where to find Claire Vo: • X: https://twitter.com/clairevo • LinkedIn: https://www.linkedin.com/in/clairevo/ • TikTok: https://www.tiktok.com/@chiefproductofficer 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) Claire’s background (04:50) How to achieve career progression (10:11) Avoiding promotion obsession (13:50) How Claire stepped into leadership roles (17:24) Operating in your zone of genius (23:03) How to maintain a fast pace (27:46) Setting a high bar for quality and talent (29:54) Normalizing feedback (33:09) Being a woman in tech (47:09) The role of a CPTO (54:19) Building ChatPRD (59:39) Tips for building a GPT (01:02:27) The impact of AI on product management (01:08:08) How AI is changing the product management role (01:14:36) Efficiency gains with ChatPRD (01:16:39) Contrarian corner: sales-led product organizations (01:20:11) Lightning round Referenced: • LaunchDarkly: https://launchdarkly.com/ • Define your zone of genius: Laura Garnett at TEDxMillRiver: https://www.youtube.com/watch?v=gQ7_r2oWlrw • Energy Audit: https://beta.mocharymethod.com/blog-post/energy-audit • How to fire people with grace, work through fear, and nurture innovation | Matt Mochary: https://www.lennyspodcast.com/videos/how-to-fire-people-with-grace-work-through-fear-and-nurture-innovation-matt-mochary/ • Radical Candor: From theory to practice with author Kim Scott: https://www.lennyspodcast.com/radical-candor-from-theory-to-practice-with-author-kim-scott/ • Optimizely: https://www.optimizely.com/ • GitLab: https://about.gitlab.com/ • ChatPRD: https://www.chatprd.ai/ • You should be playing with GPTs at work: https://www.lennysnewsletter.com/p/you-should-be-playing-with-gpts-at • SpaceX’s Starship: https://www.spacex.com/vehicles/starship/ • GitHub Copilot: https://github.com/features/copilot • Product management theater | Marty Cagan (Silicon Valley Product Group): https://www.lennyspodcast.com/product-management-theater-marty-cagan-silicon-valley-product-group/ • High Growth Handbook: Scaling Startups from 10 to 10,000 People: https://www.amazon.com/High-Growth-Handbook-Elad-Gil/dp/1732265100 • Scaling People: Tactics for Management and Company Building: https://www.amazon.com/Scaling-People-Tactics-Management-Building/dp/1953953212 • Stripe Press: https://press.stripe.com/ • Circe: https://www.amazon.com/Circe-Madeline-Miller/dp/0316556327 • Poor Things: https://www.imdb.com/title/tt14230458/ • Mythic Quest on AppleTV+: https://tv.apple.com/us/show/mythic-quest/umc.cmc.1nfdfd5zlk05fo1bwwetzldy3 • Silicon Valley on HBO: https://www.hbo.com/silicon-valley • Chrysler Pacifica: https://www.chrysler.com/pacifica.html • Waymo: https://waymo.com/ 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.

Will Larson is the chief technology officer at Carta. Prior to joining Carta, he was the CTO at Calm and held engineering leadership roles at Stripe, Uber, and Digg. He is the author of two foundational engineering career books, An Elegant Puzzle and Staff Engineer, and The Engineering Executive’s Primer, which will be released in February of next year. In our conversation, we discuss: • Systems thinking: what it is and how to apply it • Advice for product managers on fostering productive relationships with engineering managers • Why companies should treat engineers like adults • How to best measure developer productivity • Writing and its impact on his career • How to balance writing with a demanding job • How to develop your company values — Brought to you by DX—A platform for measuring and improving developer productivity: https://getdx.com/lenny | OneSchema—Import CSV data 10x faster: https://oneschema.co/lenny | Vanta—Automate compliance. Simplify security: https://vanta.com/lenny Find the transcript and references at: https://www.lennysnewsletter.com/p/the-engineering-mindset-will-larson Where to find Will Larson: • X: https://twitter.com/Lethain • LinkedIn: https://www.linkedin.com/in/will-larson-a44b543/ • Website: https://lethain.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) Will’s background (04:12) Changes in the field of engineering (06:27) We need to stop treating engineers like children (08:32) Systems thinking (13:23) Implementing systems thinking in hiring (16:32) Engineering strategy (20:21) Examples of engineering strategies (25:08) How to get good at strategy (26:48) The importance of writing about things that excite you (32:40) The biggest risk to content creation is quitting too soon (35:24) How to make time for writing (37:41) Tips for aspiring writers (41:18) Building productive relationships between product managers and engineers (43:45) Giving the same performance rating to EMs and PMs (48:24) Measuring engineering productivity (55:53) Defining company values (01:02:10) Failure corner: the Digg rewrite (01:11:05) Will’s upcoming book, The Engineering Executive’s Primer (01:12:04) Lightning round 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.