Lenny's Podcast: Product | Growth | Career

Guillermo Rauch is the founder and CEO of Vercel, creators of v0 (one of the most popular AI app building tools), and the mind behind foundational JavaScript frameworks like Next.js and Socket.io. An open source pioneer and legendary engineer, Guillermo has built tools that power some of the internet’s most innovative products, including Midjourney, Grok, and Notion. His mission is to democratize product creation, expanding the pool of potential builders from 5 million developers to over 100 million people worldwide. In this episode, you’ll learn:1. How AI will radically speed up product development—and the three critical skills PMs and engineers should master now to stay ahead2. Why the future of building apps is shifting toward prompts instead of code, and how that affects traditional product teams3. Specific ways to improve your design “taste,” plus practical tips to consistently create beautiful, user-loved products4. How Guillermo built a powerful app in under two hours for $20 (while flying and using plane Wi-Fi) that would normally take weeks and thousands of dollars in engineering time5. The exact strategies Vercel uses internally to leverage AI tools like v0 and Cursor, enabling their team of 600 to ship faster and better than ever before6. Guillermo’s actionable advice on increasing your product quality through rapid iteration, real-world user feedback, and creating intentional “exposure hours” for your team—Brought to you by:• WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs• Vanta — Automate compliance. Simplify security• LinkedIn Ads—Reach professionals and drive results for your business—Where to find Guillermo Rauch:• X: https://x.com/rauchg• LinkedIn: https://www.linkedin.com/in/rauchg/• Website: https://rauchg.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 Guillermo Rauch(04:43) v0's mission(07:03) The impact and growth of v0(15:54) The future of product development with AI(19:05) Empowering engineers and product builders(24:01) Skills for the future: coding, math, and eloquence(35:05) v0 in action: real-world applications(36:40) Tips for using v0 effectively(45:46) Core skills for building AI apps(49:44) Live demo(59:45) Understanding how AI thinks(01:04:35) AI integration and future prospects(01:07:22) Building taste(01:13:43) Limitations of v0(01:16:54) Improving the design of your product(01:20:09) The secret to product quality(01:22:35) Vercel’s AI-driven development(01:25:43) Guillermo's vision for the future—Referenced:• v0: https://v0.dev/• Vercel: https://vercel.com/• GitHub: https://github.com/• Cursor: https://www.cursor.com/• Next.js Framework: https://nextjs.org/• Claude: https://claude.ai/new• Grok: https://x.ai/• Midjourney: https://www.midjourney.com• SocketIO: https://socket.io/• Notion’s lost years, its near collapse during Covid, staying small to move fast, the joy and suffering of building horizontal, more | Ivan Zhao (CEO and co-founder): https://www.lennysnewsletter.com/p/inside-notion-ivan-zhao• Notion: https://www.notion.com/• Automattic: https://automattic.com/• Inside Bolt: From near-death to ~$40m ARR in 5 months—one of the fastest-growing products in history | Eric Simons (founder & CEO of StackBlitz): https://www.lennysnewsletter.com/p/inside-bolt-eric-simons• v0 Community: https://v0.dev/chat/community• Figma: https://www.figma.com/• Git Commit: https://www.atlassian.com/git/tutorials/saving-changes/git-commit• What are Artifacts and how do I use them?: https://support.anthropic.com/en/articles/9487310-what-are-artifacts-and-how-do-i-use-them• Design Engineering at Vercel: https://vercel.com/blog/design-engineering-at-vercel• CSS: https://en.wikipedia.org/wiki/CSS• Tailwind: https://tailwindcss.com/• Wordcel / Shape Rotator / Mathcel: https://knowyourmeme.com/memes/wordcel-shape-rotator-mathcel• Steve Jobs’s Ultimate Lesson for Companies: https://hbr.org/2011/08/steve-jobss-ultimate-lesson-fo• Bloom Hackathon: https://bloom.build/• Expenses Should Do Themselves | Saquon Barkley x Ramp (Super Bowl Ad): https://www.youtube.com/watch?v=p1Tgsy7D0Jg• Velocity over everything: How Ramp became the fastest-growing SaaS startup of all time | Geoff Charles (VP of Product): https://www.lennysnewsletter.com/p/velocity-over-everything-how-ramp• JavaScript: https://www.javascript.com/• React: https://react.dev/• Mapbox: https://www.mapbox.com/• Leaflet: https://leafletjs.com/• Escape hatches: https://react.dev/learn/escape-hatches• Supreme: https://supreme.com/• Shadcn: https://ui.shadcn.com/• Charles Schwab: https://www.schwab.com/• Fortune: https://fortune.com/• Semafor: https://www.semafor.com/• AI SDK: https://sdk.vercel.ai/• DeepSeek: https://www.deepseek.com/• Stripe: https://stripe.com/• Vercel templates: https://vercel.com/templates• GC AI: https://getgc.ai/• OpenEvidence: https://www.openevidence.com/• Paris Fashion Week: https://www.fhcm.paris/en/paris-fashion-week• Guillermo’s post on X about making great products: https://x.com/rauchg/status/1887314115066274254• Everybody Can Cook billboard: https://www.linkedin.com/posts/evilrabbit_activity-7242975574242037760-uRW9/• Ratatouille: https://www.imdb.com/title/tt0382932/—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. Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe

Kevin Weil is the chief product officer at OpenAI, where he oversees the development of ChatGPT, enterprise products, and the OpenAI API. Prior to OpenAI, Kevin was head of product at Twitter, Instagram, and Planet, and was instrumental in the development of the Libra (later Novi) cryptocurrency project at Facebook.In this episode, you’ll learn:1. How OpenAI structures its product teams and maintains agility while developing cutting-edge AI2. The power of model ensembles—using multiple specialized models together like a company of humans with different skills3. Why writing effective evals (AI evaluation tests) is becoming a critical skill for product managers4. The surprisingly enduring value of chat as an interface for AI, despite predictions of its obsolescence5. How “vibe coding” is changing how companies operate6. What OpenAI looks for when hiring product managers (hint: high agency and comfort with ambiguity)7. “Model maximalism” and why today’s AI is the worst you’ll ever use again8. Practical prompting techniques that improve AI interactions, including example-based prompting—Brought to you by:• Eppo—Run reliable, impactful experiments• Persona—A global leader in digital identity verification• OneSchema—Import CSV data 10x faster—Where to find Kevin Weil:• X: https://x.com/kevinweil• LinkedIn: https://www.linkedin.com/in/kevinweil/—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) Kevin’s background(04:06) OpenAI’s new image model(06:52) The role of chief product officer at OpenAI(10:18) His recruitment story and joining OpenAI(17:20) The importance of evals in AI(24:59) Shipping quickly and consistently(28:34) Product reviews and iterative deployment(39:35) Chat as an interface for AI(43:59) Collaboration between researchers and product teams(46:41) Hiring product managers at OpenAI(48:45) Embracing ambiguity in product management(51:41) The role of AI in product teams(53:21) Vibe coding and AI prototyping(55:55) The future of product teams and fine-tuned models(01:04:36) AI in education(01:06:42) Optimism and concerns about AI’s future(01:16:37) Reflections on the Libra project(01:20:37) Lightning round and final thoughts—Referenced:• OpenAI: https://openai.com/• The AI-Generated Studio Ghibli Trend, Explained: https://www.forbes.com/sites/danidiplacido/2025/03/27/the-ai-generated-studio-ghibli-trend-explained/• Introducing 4o Image Generation: https://openai.com/index/introducing-4o-image-generation/• Waymo: https://waymo.com/• X: https://x.com• Facebook: https://www.facebook.com/• Instagram: https://www.instagram.com/• Planet: https://www.planet.com/• Sam Altman on X: https://x.com/sama• A conversation with OpenAI’s CPO Kevin Weil, Anthropic’s CPO Mike Krieger, and Sarah Guo: https://www.youtube.com/watch?v=IxkvVZua28k• OpenAI evals: https://github.com/openai/evals• Deep Research: https://openai.com/index/introducing-deep-research/• Ev Williams on X: https://x.com/ev• OpenAI API: https://platform.openai.com/docs/overview• Dwight Eisenhower quote: https://www.brainyquote.com/quotes/dwight_d_eisenhower_164720• Inside Bolt: From near-death to ~$40m ARR in 5 months—one of the fastest-growing products in history | Eric Simons (founder & CEO of StackBlitz): https://www.lennysnewsletter.com/p/inside-bolt-eric-simons• StackBlitz: https://stackblitz.com/• Claude 3.5 Sonnet: https://www.anthropic.com/news/claude-3-5-sonnet• Anthropic: https://www.anthropic.com/• Four-minute mile: https://en.wikipedia.org/wiki/Four-minute_mile• Chad: https://chatgpt.com/g/g-3F100ZiIe-chad-open-a-i• Dario Amodei on LinkedIn: https://www.linkedin.com/in/dario-amodei-3934934/• Figma: https://www.figma.com/• Julia Villagra on LinkedIn: https://www.linkedin.com/in/juliavillagra/• Andrej Karpathy on X: https://x.com/karpathy• Silicon Valley CEO says ‘vibe coding’ lets 10 engineers do the work of 100—here’s how to use it: https://fortune.com/2025/03/26/silicon-valley-ceo-says-vibe-coding-lets-10-engineers-do-the-work-of-100-heres-how-to-use-it/• Cursor: https://www.cursor.com/• Windsurf: https://codeium.com/windsurf• GitHub Copilot: https://github.com/features/copilot• Patrick Srail on X: https://x.com/patricksrail• Khan Academy: https://www.khanacademy.org/• CK-12 Education: https://www.ck12.org/• Sora: https://openai.com/sora/• Sam Altman’s post on X about creative writing: https://x.com/sama/status/1899535387435086115• Diem (formerly known as Libra): https://en.wikipedia.org/wiki/Diem_(digital_currency)• Novi: https://about.fb.com/news/2020/05/welcome-to-novi/• David Marcus on LinkedIn: https://www.linkedin.com/in/dmarcus/• Peter Zeihan on X: https://x.com/PeterZeihan• The Wheel of Time on Prime Video: https://www.amazon.com/Wheel-Time-Season-1/dp/B09F59CZ7R• Top Gun: Maverick on Prime Video: https://www.amazon.com/Top-Gun-Maverick-Joseph-Kosinski/dp/B0DM2LYL8G• Thinking like a gardener not a builder, organizing teams like slime mold, the adjacent possible, and other unconventional product advice | Alex Komoroske (Stripe, Google): https://www.lennysnewsletter.com/p/unconventional-product-advice-alex-komoroske• MySQL: https://www.mysql.com/—Recommended books:• Co-Intelligence: Living and Working with AI: https://www.amazon.com/Co-Intelligence-Living-Working-Ethan-Mollick/dp/059371671X• The Accidental Superpower: Ten Years On: https://www.amazon.com/Accidental-Superpower-Ten-Years/dp/1538767341• Cable Cowboy: https://www.amazon.com/Cable-Cowboy-Malone-Modern-Business/dp/047170637X—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. Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe

Wes Kao is an entrepreneur, coach, and advisor. She co-founded the live learning platform Maven, backed by First Round and a16z. Before Maven, Wes co-created the altMBA with best-selling author Seth Godin. Today, Wes teaches a popular course on executive communication and influence. Through her course and one-on-one coaching, she’s helped thousands of operators, founders, and product leaders master the art of influence through clear, compelling communication. Known for her surgical writing style and no-BS frameworks, Wes returns to the pod to deliver a tactical master class on becoming a sharper, more persuasive communicator—at work, in meetings, and across your career.What you’ll learn:1. The #1 communication mistake leaders make—and Wes’s proven fix to instantly gain buy-in2. Wes’s MOO (Most Obvious Objection) framework to consistently anticipate and overcome pushback in meetings3. How to master concise communication—including Wes’s tactical approach for brevity without losing meaning4. The art of executive presence: actionable strategies for conveying confidence and clarity, even under pressure5. The “sales, then logistics” framework—and why your ideas keep getting ignored without it6. The power of “signposting”—and why executives skim your docs without it7. Exactly how to give feedback that works—Wes’s “strategy, not self-expression” principle to drive behavior change without friction8. Practical ways to instantly improve your writing, emails, and Slack messages—simple techniques Wes teaches executives9. Managing up like a pro: Wes’s clear, practical advice on earning trust, building credibility, and aligning with senior leaders10. Career accelerators: specific habits and tactics from Wes for growing your influence, advancing your career, and standing out11. Real-world communication examples—Wes breaks down real scenarios she’s solved, providing step-by-step solutions you can copy today—Brought to you by:• WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs• Vanta—Automate compliance. Simplify security• Coda—The all-in-one collaborative workspace—Where to find Wes Kao:• LinkedIn: https://www.linkedin.com/in/weskao/• Website: https://www.weskao.com/• Maven course: https://maven.com/wes-kao/executive-communication-influence—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 Wes Kao(05:34) Working with Wes(06:58) The importance of communication(10:44) Sales before logistics(18:20) Being concise(24:31) Books to help you become a better writer(27:30) Signposting and formatting(32:05) How to develop and practice your communication skills(40:41) Slack communication(42:23) Confidence in communication(50:17) The MOO framework(54:00) Staying calm in high-stakes conversations(57:36) Which tactic to start with(58:53) Effective tactics for managing up(01:04:53) Giving constructive feedback: strategy, not self-expression(01:09:39) Delegating effectively while maintaining high standards(01:16:36) The swipe file: collecting inspiration for better communication(01:19:59) Leveraging AI for better communication(01:22:01) Lightning round—Referenced:• Persuasive communication and managing up | Wes Kao (Maven, Seth Godin, Section4): https://www.lennysnewsletter.com/p/persuasive-communication-wes-kao• Making Meta | Andrew ‘Boz’ Bosworth (CTO): https://www.lennysnewsletter.com/p/making-meta-andrew-boz-bosworth-cto• Communication is the job: https://boz.com/articles/communication-is-the-job• Maven: https://maven.com/• Sales, not logistics: https://newsletter.weskao.com/p/sales-not-logistics• How to be more concise: https://newsletter.weskao.com/p/how-to-be-concise• Signposting: How to reduce cognitive load for your reader: https://newsletter.weskao.com/p/sign-posting-how-to-reduce-cognitive• Airbnb’s Vlad Loktev on embracing chaos, inquiry over advocacy, poking the bear, and “impact, impact, impact” (Partner at Index Ventures, Airbnb GM/VP Product): https://www.lennysnewsletter.com/p/impact-impact-impact-vlad-loktev• Tone and words: Use accurate language: https://newsletter.weskao.com/p/tone-and-words-use-accurate-language• Quote by Joan Didion: https://www.goodreads.com/quotes/264509-i-don-t-know-what-i-think-until-i-write-it• Strategy, not self-expression: How to decide what to say when giving feedback: https://newsletter.weskao.com/p/strategy-not-self-expression• 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• The CEDAF framework: Delegating gets easier when you get better at explaining your ideas: https://newsletter.weskao.com/p/delegating-and-explaining• Swipe file: https://en.wikipedia.org/wiki/Swipe_file• Apple Notes: https://apps.apple.com/us/app/notes/id1110145109• Claude: https://claude.ai/new• ChatGPT: https://chatgpt.com/• Arianna Huffington’s phone bed charging station (Oak): https://www.amazon.com/Arianna-Huffingtons-Phone-Charging-Station/dp/B079C5DBF4?th=1• The Harlan Coben Collection on Netflix: https://www.netflix.com/browse/genre/81180221• Oral-B Pro 1000 rechargeable electric toothbrush: https://www.amazon.com/dp/B003UKM9CO/• The Best Electric Toothbrush: https://www.nytimes.com/wirecutter/reviews/best-electric-toothbrush/• Glengarry Glen Ross on Prime Video: https://www.amazon.com/Glengarry-Glen-Ross-James-Foley/dp/B002NN5F7A• 1,000,000: https://www.lennysnewsletter.com/p/1000000—Recommended books:• On Writing Well: The Classic Guide to Writing Nonfiction: https://www.amazon.com/Writing-Well-Classic-Guide-Nonfiction/dp/0060891548/• Stein on Writing: A Master Editor of Some of the Most Successful Writers of Our Century Shares His Craft Techniques and Strategies: https://www.amazon.com/Stein-Writing-Successful-Techniques-Strategies/dp/0312254210/• On Writing: A Memoir of the Craft: https://www.amazon.com/Writing-Memoir-Craft-Stephen-King/dp/1982159375• Several Short Sentences About Writing: https://www.amazon.com/Several-Short-Sentences-About-Writing/dp/0307279413/• High Output Management: https://www.amazon.com/High-Output-Management-Andrew-Grove/dp/0679762884• Your Brain at Work: Strategies for Overcoming Distraction, Regaining Focus, and Working Smarter All Day Long: https://www.amazon.com/Your-Brain-Work-Revised-Updated/dp/0063003155/—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. Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe

Ryan Singer is one of the earliest employees and the former Head of Strategy at 37signals (the makers of Basecamp), where he spent nearly two decades refining a product development approach that helped the company build super-successful products with small teams. Based on these lessons, he wrote "Shape Up: Stop Running in Circles and Ship Work that Matters," and Ryan now works with companies of all sizes to them them escape the cycle of endless sprints, missed deadlines, and dragging projects.What you’ll learn:1. Why traditional Agile and Scrum methods often lead teams into endless cycles of work without meaningful shipping milestones.2. The “appetite-driven” approach to product development where teams set fixed timeboxes (usually six weeks maximum) and vary the scope instead of expanding timelines.3. The exact process for running effective “shaping” sessions that collaboratively define projects before committing resources.4. Why most teams struggle with too little detail in their planning, not too much.5. Why a 30-to-50-person team size is the critical breaking point when growing startups need to adopt more structured processes.6. Practical techniques for bridging the engineering-design divide by bringing technical and product perspectives together earlier in the process.7. The powerful “breadboarding” and “fat marker sketching” techniques that help teams align on solutions without getting lost in high-fidelity details.8. The clear warning signs that your current development process is failing before it’s too late to change course.9. Proven strategies to implement Shape Up methods, whether you’re working in a startup or enterprise environment.10. A step-by-step approach to transitioning from Scrum to Shape Up by piloting the methodology with a single team before broader implementation.11. Why the PM role shifts upstream in Shape Up, focusing more on problem definition than project management.12. How to adapt Shape Up principles to your company’s unique context, even if it’s nothing like Basecamp.—Brought to you by:• WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs• Merge—A single API to add hundreds of integrations into your app• Airtable ProductCentral—Launch to new heights with a unified system for product development—Where to find Ryan Singer:• X: https://x.com/rjs• LinkedIn: https://www.linkedin.com/in/feltpresence/• Website: https://www.ryansinger.co/• Course: https://www.ryansinger.co/srl/—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) Ryan’s background(04:38) The origins of Shape Up(07:40) Implementing Shape Up in different companies(09:56) How Shape Up is different(19:02) The core elements of Shape Up(26:29) Shaping sessions and timeboxing(37:23) Flexible sprint planning(38:56) The output of a shaping session(46:57) Balancing detail and flexibility(53:50) A deep dive into shaping sessions(01:01:32) Fat marker sketches(01:02:48) Getting started using Shape Up(01:13:20) Signs it's time to try the Shape Up method(01:18:25) Feature factories(01:25:59) The role of the PM in Shape Up(01:28:26) What makes Basecamp unique(01:35:55) The second edition of the book(01:38:30) Linking product strategy and shaping(01:41:53) Conclusion and final thoughts—Referenced:• Basecamp: https://basecamp.com/• David Heinemeier Hansson on LinkedIn: https://www.linkedin.com/in/david-heinemeier-hansson-374b18221/• Jason Fried on LinkedIn: https://www.linkedin.com/in/jason-fried/• Jason Fried challenges your thinking on fundraising, goals, growth, and more: https://www.lennysnewsletter.com/p/jason-fried-challenges-your-thinking• Des Traynor on LinkedIn: https://www.linkedin.com/in/destraynor/• Intercom: https://www.intercom.com/• The ultimate guide to JTBD | Bob Moesta (co-creator of the framework): https://www.lennysnewsletter.com/p/the-ultimate-guide-to-jtbd-bob-moesta• How to find work you love | Bob Moesta (Jobs-to-be-Done co-creator, author of “Job Moves”): https://www.lennysnewsletter.com/p/how-to-find-work-you-love-bob-moesta• Scrum: https://www.scrum.org/• 37signals: https://37signals.com/• Jobs to Be Done Theory: https://www.christenseninstitute.org/theory/jobs-to-be-done/—Recommended books:• Shape Up: Stop Running in Circles and Ship Work That Matters: https://basecamp.com/shapeup• Demand-Side Sales 101: Stop Selling and Help Your Customers Make Progress: https://www.amazon.com/Demand-Side-Sales-101-Customers-Progress/dp/1544509987/• Competing Against Luck: The Story of Innovation and Customer Choice: https://www.amazon.com/Competing-Against-Luck-Innovation-Customer/dp/0062435612/• Job Moves: 9 Steps for Making Progress in Your Career: https://www.amazon.com/Job-Moves-Making-Progress-Career/dp/0063283581—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. Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe

Gaurav Misra is the co-founder and CEO of Captions, an AI-powered video creation company and one of the most successful consumer AI products in the world today. Previously he was a product leader at Snap, where he created the design engineering function and spent years helping develop features used by hundreds of millions of users worldwide. With a background in both engineering and design, Gaurav brings a unique cross-functional perspective to product development.What you’ll learn:1. Why the “ship a marketable feature every week” approach helps his team stay focused and the product stay top of mind for users amid constant AI breakthroughs2. How to balance rapid shipping with maintaining quality by cutting scope rather than compromising on timelines3. The “secret roadmap” strategy that helps Captions develop breakthrough features competitors never see coming4. Why taking on strategic technical debt is essential for startups to outpace larger companies5. How Captions accidentally ignored their most successful product for 1.5 years (and why it still grew to 500K users with no updates or support)6. How Snap’s unique product development approach—with designers functioning as PMs—enabled their success as the last major social network to break through7. Why AI video will transform marketing before other industries—Brought to you by:• Brex — The banking solution for startups• Paragon—Ship every SaaS integration your customers want• Coda—The all-in-one collaborative workspace—Find the transcript at: https://www.lennysnewsletter.com/p/how-to-win-in-the-ai-era-gaurav-misra—Where to find Gaurav Misra:• X: https://x.com/gmharhar• LinkedIn: https://www.linkedin.com/in/gamisra1/—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) Gaurav’s background(04:47) The exciting era of AI and startups(09:30) Staying top of mind(11:26) Tips for staying focused(13:14) Shipping marketable features weekly(19:03) Managing technical debt in startups(25:31) Snap’s unique product development approach(32:09) Brainstorming with AI(35:09) What Snap got right(41:06) Scaling with a small, agile team(49:33) The shift toward prototyping in product management(51:47) The product manager role(55:40) Snap’s mission and product decisions(01:02:13) The future of AI-generated video(01:10:20) Leveraging AI for marketing(01:14:37) Failure corner(01:20:21) Lightning round and closing thoughts—Referenced:• Snap: https://www.snap.com/• Captions: https://www.captions.ai/• Iron Man on Disney+: https://www.disneyplus.com/movies/iron-man/6aM2a8mZATiu• J.A.R.V.I.S.: https://en.wikipedia.org/wiki/J.A.R.V.I.S.• Cursor: https://www.cursor.com/• Devin: https://devin.ai/• Eye contact: https://www.captions.ai/eye-contact• Nvidia: https://www.nvidia.com• Descript: https://www.descript.com• Evan Spiegel on LinkedIn: https://www.linkedin.com/in/evan-spiegel-8ab74034a/• TikTok: https://www.tiktok.com/• Spotlight: https://www.snapchat.com/spotlight/• Building product at Stripe: craft, metrics, and customer obsession | Jeff Weinstein (Product lead): https://www.lennysnewsletter.com/p/building-product-at-stripe-jeff-weinstein• Patrick Collison on X: https://x.com/patrickc• DeepSeek: https://www.deepseek.com/• ByteDance Goku: New video generation AI model, better than OpenAI Sora: https://medium.com/data-science-in-your-pocket/bytedance-goku-new-video-generation-ai-model-better-than-openai-sora-56c017a320a5• Will Smith eating spaghetti and other weird AI benchmarks that took off in 2024: https://techcrunch.com/2024/12/31/will-smith-eating-spaghetti-and-other-weird-ai-benchmarks-that-took-off-in-2024/• Silo on AppleTV+: https://tv.apple.com/us/show/silo/umc.cmc.3yksgc857px0k0rqe5zd4jice• Severance on AppleTV+: https://tv.apple.com/us/show/severance/umc.cmc.1srk2goyh2q2zdxcx605w8vtx• Linear: https://linear.app/• Superhuman: https://superhuman.com/• Notion: https://www.notion.com• Perplexity: https://www.perplexity.ai/• OmniHuman-1 AI Video Generation Looks Too Real: https://www.youtube.com/watch?v=fY0KB516m-E—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. Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe

Rahul Vohra is the founder and CEO of Superhuman. Prior to Superhuman, Rahul founded Rapportive, the first Gmail plug-in to scale to millions of users, which he sold to LinkedIn in 2012. He is also a prominent angel investor, and his fund has invested $50 million in over 120 companies, including Placer, Supabase, Mercury, Zip, ClassDojo, and Writer.What you’ll learn:• The unexpected insight about virality Rahul gained from LinkedIn’s head of growth.• Why Rahul restructured his entire executive team to spend 60% to 70% of his time on product, design, and marketing instead of the typical CEO responsibilities.• The counterintuitive approach to finding product-market fit using a methodical system inspired by Sean Ellis, and how this algorithmically determines your roadmap.• How manually onboarding every user (Superhuman had 20 full-time people doing this at peak) created superfans and allowed engineers to focus on product rather than onboarding flows.• The “Single Decisive Reason” framework for making better decisions by avoiding collections of weak justifications.• How Superhuman’s AI features have evolved to create a truly intelligent email experience that works while you sleep.—Brought to you by:• Eppo—Run reliable, impactful experiments• Fundrise Flagship Fund—Invest in $1.1 billion of real estate• OneSchema—Import CSV data 10x faster—Find the transcript at: https://www.lennysnewsletter.com/p/superhumans-secret-to-success-rahul-vohra—Where to find Rahul Vohra:• X: https://x.com/rahulvohra• LinkedIn: https://www.linkedin.com/in/rahulvohra/• Email: Rahul@superhuman.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 Rahul and Superhuman(05:00) The most pivotal moment in Rahul's career(07:01) The secret to virality(11:02) Superhuman’s product evolution and core values(13:32) Overcoming slowdowns at scale(18:06) Time management and meditation(27:35) The role of a president(30:56) Attention to detail(43:00) Finding your unique position(47:32) The power of manual onboarding(52:37) Mastering product-market fit(59:33) Game design in business software(01:05:35) Contrarian pricing strategies(01:09:29) Leveraging AI(01:15:40) Transitioning to enterprise solutions(01:19:08) The Single Decisive Reason framework(01:22:32) Conclusion and final thoughts—Referenced:• Superhuman: https://superhuman.com/• Rapportive: https://techcrunch.com/2012/02/22/rapportive-linkedin-acquisition/• Elliot Shmukler on LinkedIn: https://www.linkedin.com/in/eshmu/• What Are ‘Whales’ in Video Games: https://gamerant.com/video-games-whales-concept-term-explained/• Figma: https://www.figma.com/• Notion: https://www.notion.com/• Loom: https://www.loom.com/• How to use Team Comments to reimagine email collaboration: https://blog.superhuman.com/how-to-use-team-comments-to-reimagine-email-collaboration/• Rajiv Ayyangar’s post on X about Superhuman: https://x.com/rajivayyangar/status/1816176308130570385• Transcendental Meditation: https://www.tm.org/• Laurent Valosek on LinkedIn: https://www.linkedin.com/in/laurent-valosek-18708b5a/• Peak Leadership Institute: https://www.peakleadershipinstitute.com/• Ed Sim’s website: https://edsim.net/• Adelle Sans: https://fonts.adobe.com/fonts/adelle-sans• Comic Sans: https://en.wikipedia.org/wiki/Comic_Sans• Greenfield project: https://en.wikipedia.org/wiki/Greenfield_project• Why Mailbox died: https://www.theverge.com/2015/12/8/9873268/why-dropbox-mailbox-shutdown• Bill Trenchard on X: https://x.com/btrenchard• How Superhuman Built an Engine to Find Product-Market Fit: https://review.firstround.com/how-superhuman-built-an-engine-to-find-product-market-fit/• Using the Sean Ellis Test for Measuring Your Product-Market Fit: https://medium.productcoalition.com/using-sean-ellis-test-for-measuring-your-product-market-fit-c8ac98053c2c• Sean Ellis on LinkedIn: https://www.linkedin.com/in/seanellis/• The original growth hacker reveals his secrets | Sean Ellis (author of “Hacking Growth”): https://www.lennysnewsletter.com/p/the-original-growth-hacker-sean-ellis• The Trouble with Rewards: https://www.kornferry.com/insights/briefings-magazine/issue-13/519-the-trouble-with-rewards• The art and science of pricing | Madhavan Ramanujam (Monetizing Innovation, Simon-Kucher): https://www.lennysnewsletter.com/p/the-art-and-science-of-pricing-madhavan•  Van Westendorp Price Sensitivity Meter: https://en.wikipedia.org/wiki/Van_Westendorp%27s_Price_Sensitivity_Meter• AI-powered email for high-performing teams: https://superhuman.com/ai• Linear’s secret to building beloved B2B products | Nan Yu (Head of Product): https://www.lennysnewsletter.com/p/linears-secret-to-building-beloved-b2b-products-nan-yu• Single Decisive Reason: decision-making for fast-scaling startups: https://blog.superhuman.com/single-decisive-reason-decision-making-for-fast-scaling-startups/• Reid Hoffman on LinkedIn: https://www.linkedin.com/in/reidhoffman/—Recommended books:• Positioning: The Battle for Your Mind: https://www.amazon.com/Positioning-Battle-Your-Al-Ries/dp/0071373586• Monetizing Innovation: How Smart Companies Design the Product Around the Price: https://www.amazon.com/Monetizing-Innovation-Companies-Design-Product/dp/1119240867—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. Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe

Susan Cain, author of the groundbreaking bestseller Quiet: The Power of Introverts in a World That Can’t Stop Talking, shares a guide for how introverts can thrive in the workplace without sacrificing their authentic selves. Drawing from her extensive research and personal experience, Cain offers a powerful reframing: success doesn’t require becoming more extroverted—it demands becoming more fully yourself.—What you’ll learn:1. A simple definition of introversion and how it differs from shyness—plus a simple two-question test to determine where you fall on the spectrum2. Five practical tactics introverts can use to be more successful in business while staying true to their natural temperament3. How to handle challenging workplace scenarios like meetings dominated by loud voices and networking events that drain your energy4. Specific strategies for managers and founders to create environments where introverted team members can contribute their best work5. Practical techniques for saying no to energy-draining commitments6. Strategies for managers to better support and leverage introverted team members7. Practical advice for raising introverted children to help them develop confidence while honoring their natural temperament8. Why seeking to become “more extroverted” is the wrong goal—and what to focus on instead to achieve professional success—Brought to you by:• Enterpret—Transform customer feedback into product growth• Vanta—Automate compliance. Simplify security• Fundrise Flagship Fund—Invest in $1.1 billion of real estate—Find the transcript at: https://www.lennysnewsletter.com/p/the-hidden-power-of-introverts-susan-cain—Where to find Susan Cain:• X: https://x.com/susancain• LinkedIn: https://www.linkedin.com/in/susancain/• Website: https://susancain.net/• Instagram: https://www.instagram.com/susancainauthor/#• Facebook: https://www.facebook.com/authorsusancain• Substack: https://thequietlife.net/—In this episode, we cover:(00:00) Introduction to Susan Cain(05:07) Understanding introversion(08:55) The spectrum of introversion and extroversion(13:27) Overcoming public speaking anxiety(17:13) Learning to embrace your introverted self(23:16) The power of leaning into your strengths(24:36) Strategies for introverts to thrive in their career(34:06) The importance of saying no(38:35) What to do instead of networking(41:59) Effective meeting participation for introverts(47:31) Creating a productive work environment(51:14) Raising an introverted child(57:58) Finding the right career fit(01:08:09) Lightning round and final thoughts—Referenced:• The power of introverts: https://www.ted.com/talks/susan_cain_the_power_of_introverts• The hidden power of sad songs and rainy days: https://www.ted.com/talks/susan_cain_and_min_kym_the_hidden_power_of_sad_songs_and_rainy_days• Why bittersweet emotions underscore life’s beauty: https://www.ted.com/talks/susan_cain_why_bittersweet_emotions_underscore_life_s_beauty• Desensitization: https://en.wikipedia.org/wiki/Desensitization_(psychology)• Malcolm Gladwell’s website: https://www.gladwellbooks.com/• Warren Buffett on X: https://x.com/warrenbuffett• Dale Carnegie speaking courses: https://www.dalecarnegie.com/en/presentation-skills-public-speaking-training• Bill Gates on X: https://x.com/billgates• Kathy Fish on LinkedIn: https://www.linkedin.com/in/kathy-fish-23b5777/• Why most public speaking advice is wrong—and how to finally overcome your speaking anxiety | Tristan de Montebello (CEO & co-founder of Ultraspeaking): https://www.lennysnewsletter.com/p/master-public-speaking-tristan-de-montebello• Ultraspeaking: https://ultraspeaking.com/lenny/• Rethinking the Extraverted Sales Ideal: The Ambivert Advantage: https://faculty.wharton.upenn.edu/wp-content/uploads/2013/06/Grant_PsychScience2013.pdf• Cutco: https://www.cutco.com/• Tim Ferriss’s post about his new book: https://x.com/tferriss/status/1878936085033791817•  Mihaly Csikszentmihalyi: https://en.wikipedia.org/wiki/Mihaly_Csikszentmihalyi• Naval on X: https://x.com/naval• On saying no: https://www.lennysnewsletter.com/p/how-to-say-no• Susan Cain—How to Overcome Fear and Embrace Creativity: https://tim.blog/2019/01/24/susan-cain/• Zigging vs. zagging: How HubSpot built a $30B company | Dharmesh Shah (co-founder/CTO): https://www.lennysnewsletter.com/p/lessons-from-30-years-of-building• Renee Wood on LinkedIn: https://www.linkedin.com/in/recoale/• The Sopranos on Max: https://play.max.com/show/818c3d9d-1831-48a6-9583-0364a7f98453• The Talented Mr. Ripley on Prime Video: https://www.primevideo.com/detail/The-Talented-Mr-Ripley/0HA0GNFQ4ZXYPDNJHQEENK2Q6Q• Tugboat Institute: https://www.tugboatinstitute.com/• Leonard Cohen quote: https://www.goodreads.com/quotes/4484-there-is-a-crack-in-everything-that-s-how-the-light—Recommended books:• Quiet: The Power of Introverts in a World That Can’t Stop Talking: https://www.amazon.com/Quiet-Power-Introverts-World-Talking/dp/0307352153• Creativity: Flow and the Psychology of Discovery and Invention: https://www.amazon.com/Creativity-Flow-Psychology-Discovery-Invention/dp/0062283251• Quiet Power: The Secret Strengths of Introverted Kids: https://www.amazon.com/Quiet-Power-Secret-Strengths-Introverted/dp/0147509920• Gandhi: An Autobiography—The Story of My Experiments with Truth: https://www.amazon.com/Gandhi-Autobiography-Story-Experiments-Truth/dp/0807059099• Flow: The Psychology of Optimal Experience: https://www.amazon.com/Flow-Psychology-Experience-Perennial-Classics/dp/0061339202• The Power of Myth: https://www.amazon.com/Power-Myth-Joseph-Campbell/dp/0385418868/• Bittersweet: How Sorrow and Longing Make Us Whole: https://www.amazon.com/Bittersweet-Oprahs-Book-Club-Longing/dp/0451499794• Good Energy: The Surprising Connection Between Metabolism and Limitless Health: https://www.amazon.com/Good-Energy-Surprising-Connection-Metabolism/dp/0593712641• The 5 Types of Wealth: A Transformative Guide to Design Your Dream Life: https://www.amazon.com/Types-Wealth-Transformative-Guide-Design/dp/059372318X—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. Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe

Eric Simons is the founder and CEO of StackBlitz, the company behind Bolt—the #1 web-based AI coding agent and one of the fastest-growing products in history. After nearly shutting down, StackBlitz launched Bolt on Twitter and exploded from zero to $40 million ARR and 1 million monthly active users in about five months.What you’ll learn:1. How Bolt reached nearly $40M ARR and 3 million registered users in just five months with a team of only 15 to 20 people2. How Bolt leverages WebContainer technology—a browser-based operating system developed over seven years—to create a dramatically faster, more reliable AI coding experience than competitors3. Why Anthropic’s 3.5 Sonnet model was the critical breakthrough that made AI-generated code production-ready and unlocked the entire text-to-app market4. Why PMs may be better positioned than engineers in the AI era5. How AI will dramatically reshape company org charts6. Eric’s wild founder story (including squatting at AOL’s HQ) and how scrappiness fueled his innovation—Brought to you by:• Eppo—Run reliable, impactful experiments• Fundrise Flagship Fund—Invest in $1.1 billion of real estate• OneSchema—Import CSV data 10x faster—Find the transcript at: https://www.lennysnewsletter.com/p/inside-bolt-eric-simons—Where to find Eric Simons:• X: https://x.com/ericsimons40• LinkedIn: https://www.linkedin.com/in/eric-simons-a464a664/• Email: Eric@stackblitz.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 Eric Simons and StackBlitz(04:46) Unprecedented growth and user adoption(10:40) Demo: Building a Spotify clone with Bolt(15:28) Expanding to native mobile apps with Expo(19:09) The journey and technology behind WebContainer(25:03) Lessons learned and future outlook(29:15) Post-launch analysis(34:15) Growing fast with a small team(41:00) Prioritization at Bolt(45:51) Tooling and PRD's(48:42) Integration and use cases of Bolt(52:24) Limitations of Bolt(54:24) The role of PMs and developers in the AI era(59:56) Skills for the future(01:14:18) Upcoming features of Bolt(01:20:17) How to get the most out of Bolt(01:23:00) Eric’s journey and final thoughts—Referenced:• Bolt: https://bolt.new/• Cursor: https://www.cursor.com/• Wix: https://www.wix.com/• Squarespace: https://www.squarespace.com/• Dylan Field on LinkedIn: https://www.linkedin.com/in/dylanfield/• Evan Wallace’s website: https://madebyevan.com/• WebGL: https://en.wikipedia.org/wiki/WebGL• WebAssembly: https://webassembly.org/• CloudNine: https://cloudnine.com/• Canva: https://www.canva.com/• StackBlitz: https://stackblitz.com/• Lessons from 1,000+ YC startups: Resilience, tar pit ideas, pivoting, more | Dalton Caldwell (Y Combinator, Managing Director): https://www.lennysnewsletter.com/p/lessons-from-1000-yc-startups• Y Combinator: https://www.ycombinator.com/• Anthropic: https://www.anthropic.com/• Dario Amodei on LinkedIn: https://www.linkedin.com/in/dario-amodei-3934934/• Linear: https://linear.app/• Notion: https://www.notion.com/• Salesforce: https://www.salesforce.com/• Atlassian: https://www.atlassian.com/• Photoshop: https://www.adobe.com/products/photoshop/• Figma: https://www.figma.com/• Greenfield projects: https://en.wikipedia.org/wiki/Greenfield_project• Gartner: https://www.gartner.com/• OpenAI researcher on why soft skills are the future of work | Karina Nguyen (Research at OpenAI, ex-Anthropic): https://www.lennysnewsletter.com/p/why-soft-skills-are-the-future-of-work-karina-nguyen• Albert Pai on LinkedIn: https://www.linkedin.com/in/albertpai/• Bolt’s post on X about “Bolt Builders”: https://x.com/boltdotnew/status/1887546089294995943• Sonnet: https://www.anthropic.com/claude/sonnet• ChatGPT: https://chatgpt.com/• Breaking the Rules: The Young Entrepreneur Who Squatted at AOL: https://www.inc.com/john-mcdermott/eric-simons-interview-young-entrepreneur-squatted-at-aol.html• Imagine K12: http://www.imaginek12.com/• Geoff Ralston on LinkedIn: https://www.linkedin.com/in/geoffralston/• AOL: https://www.aol.com/• Bolt on X: https://x.com/boltdotnew—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. Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe

Anton Osika is the co-founder and CEO of Lovable, which is building what they call “the last piece of software”—an AI-powered tool that turns descriptions into working products without requiring any coding knowledge. Since launching three months ago, Lovable hit $4 million ARR in the first four weeks and $10 million ARR in two months with a team of just 15 people, making it Europe’s fastest-growing startup ever.—What you’ll learn:1. Why you need to be in the top 1% of AI tool users2. Watch Lovable build a functional Airbnb clone in 30 seconds—complete with working features and modern design3. The unconventional hiring approach that helped build a 15-person team capable of extraordinary execution4. How traditional product development will look with AI5. What skills will matter most to product teams going forward6. How Anton’s team discovered a breakthrough in AI “unsticking itself”—Brought to you by:• Sinch—Build messaging, email, and calling into your product• Persona—A global leader in digital identity verification• Fundrise Flagship Fund—Invest in $1.1 billion of real estate—Find the transcript at: https://www.lennysnewsletter.com/p/building-lovable-anton-osika—Where to find Anton Osika:• X: https://x.com/antonosika• LinkedIn: https://www.linkedin.com/in/antonosika/—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 Anton and Lovable(05:12) Lovable’s rapid growth(09:39) Live demo: Building an Airbnb clone(18:34) Tips for mastering Lovable(21:42) The origin story(26:50) Scaling laws and getting AI unstuck(33:20) Reliability and unique features(36:25) The vision and future of Lovable(38:14) Skills and job market evolution in the age of AI(40:30) Hiring philosophy and team dynamics(46:21) Building in Europe(48:02) Prioritization and product roadmap(51:38) Tools and work environment(53:17) Tactics for moving fast(54:37) Advice for building product teams(57:11) Empowering non-technical founders(58:31) Future developments and user support(01:01:23) Failure corner(01:05:20) Final thoughts and advice—Referenced:• Lovable: https://lovable.dev/• Lovable Launched: https://launched.lovable.app/• Cloudflare: https://www.cloudflare.com/• Supabase: https://supabase.com/• GPT engineer: https://github.com/gpt-engineer-org/gptengineer.app• Microsoft Copilot: https://copilot.microsoft.com/chats/cmFw8dTsGU8D6b9siqQ6U• Fabian Hedin on LinkedIn: https://www.linkedin.com/in/fabian-hedin-2377b0144/• Behind the product: Replit | Amjad Masad (co-founder and CEO): https://www.lennysnewsletter.com/p/behind-the-product-replit-amjad-masad• Replit: https://replit.com/• Cursor: https://www.cursor.com• Bolt: https://bolt.new/• GitHub: https://github.com/• Lane Shackleton on LinkedIn: https://www.linkedin.com/in/laneshackleton/• FigJam: https://www.figma.com/figjam/• Linear: https://linear.app/• Sana Labs: https://sanalabs.com/• Duolingo: https://www.duolingo.com/• Claude: https://claude.ai/• ChatGPT: https://chatgpt.com/• Lovable on X: https://x.com/Lovable_dev—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. Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe

Ivan Zhao is the co-founder and CEO of Notion. Ivan shares the untold story of Notion, from nearly running out of database space during Covid to finding product-market fit after several “lost years,” and the hard-won lessons along the way.—What you’ll learn:1. Why you sometimes need to “hide your vision” behind something people actually want—what Ivan calls “sugar-coating the broccoli”2. How Ivan and his co-founder persevered through multiple product resets and complete code rewrites3. Why Notion prioritized systems over headcount, keeping the team small and focused even at scale4. Why Ivan believes in craft and values as the foundation for product development, balancing technical excellence with aesthetic sensibility5. The surprising story of how Notion nearly collapsed during Covid when their single database almost ran out of space with only weeks to spare6. Community-led growth tactics7. Ivan’s unique journey from a small town in China8. Much more—Brought to you by:• Eppo—Run reliable, impactful experiments• Airtable ProductCentral—Launch to new heights with a unified system for product development• Sinch—Build messaging, email, and calling into your product—Find the transcript at: https://www.lennysnewsletter.com/p/inside-notion-ivan-zhao—Where to find Ivan Zhao:• X: https://x.com/ivanhzhao• LinkedIn: https://www.linkedin.com/in/ivanhzhao/—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 Ivan Zhao(04:41) Ivan’s early life and education(07:46) Discovering the vision for Notion(10:49) The lost years of Notion(13:56) Rebuilding and perseverance(17:14) Layoffs and company morale(18:53) Advice for startup founders(25:08) Product-market fit(29:56) Staying lean and efficient(34:27) Creating a unique office culture(37:20) Craft and values: the foundation of Notion’s philosophy(38:44) Navigating tradeoffs in product and business building(41:24) Leadership and personal growth(49:11) Challenges and crises: lessons from Notion’s journey(51:08) Building horizontal software: joys and pains(01:02:40) Philosophy of tools and human potential(01:06:17) Lightning round and final thoughts—Referenced:• Ürümqi: https://en.wikipedia.org/wiki/%C3%9Cr%C3%BCmqi• Notion: https://www.notion.com/• SpongeBob SquarePants: https://en.wikipedia.org/wiki/SpongeBob_SquarePants• Augmenting Human Intellect: https://web.stanford.edu/class/history34q/readings/Engelbart/Engelbart_AugmentIntellect.html• Alan Kay: https://en.wikipedia.org/wiki/Alan_Kay• Ted Nelson: https://en.wikipedia.org/wiki/Ted_Nelson• Steve Jobs on Why Computers Are Like a Bicycle for the Mind (1990): https://www.themarginalian.org/2011/12/21/steve-jobs-bicycle-for-the-mind-1990/• Xerox Alto: https://en.wikipedia.org/wiki/Xerox_Alto• React: https://react.dev/• Simon Last on LinkedIn: https://www.linkedin.com/in/simon-last-41404140/• Magna-Tiles: https://www.magnatiles.com/• Design on a deadline: How Notion pulled itself back from the brink of failure: https://www.figma.com/blog/design-on-a-deadline-how-notion-pulled-itself-back-from-the-brink-of-failure/• Bryan Johnson on X: https://x.com/bryan_johnson• 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• Smalltalk: https://en.wikipedia.org/wiki/Smalltalk#:• Lisp: https://en.wikipedia.org/wiki/Lisp_(programming_language)• DeepSeek: https://www.deepseek.com/• Shana Fisher: https://www.crunchbase.com/person/shana-fisher• LAMY 2000 fountain pens: https://www.jetpens.com/LAMY-2000-Fountain-Pens/• Macintosh 128K: https://en.wikipedia.org/wiki/Macintosh_128K• Toshiba rice cooker: https://www.toshiba-lifestyle.com/us/cooking-appliances/rice-cooker• Transistor radio: https://en.wikipedia.org/wiki/Transistor_radio• Jira: https://www.atlassian.com/software/jira• Salesforce: https://www.salesforce.com/• HubSpot: https://www.hubspot.com/• Zendesk: https://www.zendesk.com/• Misattributed McLuhan quote: https://mcluhangalaxy.wordpress.com/2013/04/01/we-shape-our-tools-and-thereafter-our-tools-shape-us/• Phin Barnes on LinkedIn: https://www.linkedin.com/in/phineasbarnes/• Hacker News: https://news.ycombinator.com/• Pablo Picasso quote: https://www.goodreads.com/quotes/629531-good-artists-copy-great-artists-steal#:~• Connections with James Burke on Prime Video: https://www.amazon.com/gp/video/detail/amzn1.dv.gti.484e32c5-60bd-4493-a800-e44fd0940312• The Enneagram Institute: https://www.enneagraminstitute.com/—Recommended book:• The Romance of the Three Kingdoms: https://www.amazon.com/Romance-Three-Kingdoms-Luo-Guanzhong/dp/024133277X—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. Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe

Matt Mullenweg is the co-founder of WordPress, the open source platform powering a staggering 43% of the internet. He also serves as CEO of Automattic—the parent company of brands like WordPress.com, WooCommerce, and Tumblr—which is worth over $7 billion, with over 1,700 employees across 90 countries. In this episode, he discusses some of the most controversial topics surrounding WordPress, Automattic, and the broader open source community.—What you’ll learn:• Matt’s response to public criticism• Why products like Meta’s Llama are “fake open source”• How his team is turning around Tumblr after acquiring it for just $3 million (after Yahoo bought it for $1.1 billion)• Why he mortgaged his home to fund San Francisco’s iconic Bay Lights project• Matt’s philosophy: “Don’t just build a product; build a movement”• Why open source matters: “If the Founding Fathers were around today, they’d be open source advocates”—Brought to you by:• WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs• Vanta—Automate compliance. Simplify security.• Loom—The easiest screen recorder you’ll ever use—Find the transcript at: https://www.lennysnewsletter.com/p/the-creator-of-wordpress-opens-up-matt-mullenweg—Where to find Matt Mullenweg:• X: https://x.com/photomatt• LinkedIn: https://www.linkedin.com/in/mattm/• Instagram: https://www.instagram.com/photomatt/• Website: https://ma.tt/—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 Mullenweg(05:10) Matt’s career journey(11:15) Bay Lights project and philanthropy(17:28) How Matt got involved with open source(23:25) Why products like Meta’s Llama are “fake open source”(27:14) The future of open source and how to get involved(35:25) Building a successful online community(39:12) The WP Engine controversy(50:24) Facing criticism and controversy(55:29) Addressing community concerns(01:08:29) Forking Advanced Custom Fields(01:11:15) The role of social media and public perception(01:16:43) Acquiring and reviving Tumblr(01:24:25) Automattic’s acquisition strategy(01:28:51) Final thoughts and future plans—Referenced:• WordPress: https://wordpress.com/• Automattic: https://automattic.com/• CNET: https://www.cnet.com/• Akismet: https://akismet.com/wordpress/• Jetpack: https://jetpack.com/• Toni Schneider on LinkedIn: https://www.linkedin.com/in/tonischneider/• WooCommerce: https://woocommerce.com/• Beeper: https://www.beeper.com/• Day One: https://dayoneapp.com/• Simplenote: https://simplenote.com/• Pocket Casts: https://pocketcasts.com/• Creative Commons: https://creativecommons.org/• Audrey Capital: https://audrey.co/• Stripe: https://stripe.com/• SpaceX: https://www.spacex.com/• Calm: https://www.calm.com/• August: https://august.com/• Daylight Computer: https://daylightcomputer.com/• Keys Jazz Bistro: https://keysjazzbistro.com/• Joomla: https://www.joomla.org/• Drupal: https://new.drupal.org/• Shopify: https://www.shopify.com/• Wix: https://www.wix.com/• Squarespace: https://www.squarespace.com/• Tumblr: https://www.tumblr.com/• Gravatar: https://gravatar.com/• The Bay Lights: https://illuminate.org/projects/thebaylights/• The Bay Lights 360: https://illuminate.org/the-bay-lights-360/• Ben Davis on LinkedIn: https://www.linkedin.com/in/ben-davis-sf/• Kinder High School for the Performing and Visual Arts: https://www.houstonisd.org/hspva• Jack Dorsey: We’re Losing our Free Will to Algorithms: https://www.youtube.com/watch?v=9_8NganZSFI• Marc Andreessen: https://a16z.com/author/marc-andreessen/• Bill Gurley on LinkedIn: https://www.linkedin.com/in/billgurley/• An inside look at X’s Community Notes | Keith Coleman (VP of Product) and Jay Baxter (ML Lead): https://www.lennysnewsletter.com/p/how-x-built-the-best-fact-checking-system-on-the-internet• Llama: https://www.llama.com/• WordCamp US & Ecosystem Thinking: https://ma.tt/2024/09/ecosystem-thinking/• As Wall Street Chases Profits, Fire Departments Have Paid the Price: https://www.nytimes.com/2025/02/17/us/fire-engines-shortage-private-equity.html• WordCamp Asia: https://asia.wordcamp.org/2025/• Justin Baldoni Hit with Defamation Suit as PR Teams Turn on Each Other over Blake Lively’s ‘It Ends with Us’ Smear Campaign Allegations: https://deadline.com/2024/12/justin-baldoni-defamation-lawsuit-publicist-blake-lively-1236241784/• How WordPress Hot Nacho Scandal Shapes WP Engine Dispute: https://www.searchenginejournal.com/how-wordpress-hot-nacho-scandal-shapes-wp-engine-dispute/539069/• Gutenberg: https://wordpress.org/gutenberg/• ClassicPress: https://www.classicpress.net/• Behind the founder: Marc Benioff: https://www.lennysnewsletter.com/p/behind-the-founder-marc-benioff• Mary Hubbard on LinkedIn: https://www.linkedin.com/in/maryfhubbard/• Brian Chesky’s new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach• Founder mode: https://paulgraham.com/foundermode.html• Cow.com: https://www.cow.com/• David Karp on X: https://x.com/davidkarp• Marissa Mayer on LinkedIn: https://www.linkedin.com/in/marissamayer/• Alibaba: https://www.alibaba.com/• WP Engine Tracker: https://wordpressenginetracker.com/• Kumbh Mela: https://en.wikipedia.org/wiki/Kumbh_Mela—Recommended book:• Maintenance: Of Everything (in progress): https://books.worksinprogress.co/book/maintenance-of-everything/addenda/page/introduction—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. Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe

Keith Coleman (VP of product) and Jay Baxter (founding ML engineer), the minds behind Community Notes, reveal how a small, scrappy team inside Twitter/X built the most trusted crowdsourced information system on the internet—one that’s changing the way we understand truth online. What you’ll learn:1. How Community Notes actually works—a deep dive into the groundbreaking algorithm that rewards “bridging agreement” instead of majority rule2. The seemingly crazy yet brilliant way this idea survived multiple CEO changes—from Jack to Parag to Elon3. How this project started with a dumpster fire GIF (literally)—the untold backstory of its early launch4. The secret to running ultra-fast, high-impact product teams—no OKRs, no Jira; just one Google Doc5. What Meta’s adoption of Community Notes means for the future of online (mis)information—why this open source system is becoming the industry standard—Brought to you by:• WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs• Productboard—Make products that matter• Wix Studio—The web creation platform built for agencies—Find the transcript at: https://www.lennysnewsletter.com/p/how-x-built-the-best-fact-checking-system-on-the-internet—Where to find Keith Coleman:• X: https://x.com/kcoleman• LinkedIn: https://www.linkedin.com/in/keith-coleman-19b12b46/—Where to find Jay Baxter:• X: https://x.com/_jaybaxter_• LinkedIn: https://www.linkedin.com/in/jaybaxter/• Website: http://jaybaxter.net/—In this episode, we cover:(00:00) Introduction to Community Notes(06:56) How the “bridging-based” algorithm works(13:33) The impact and scale of Community Notes(17:24) Understanding the note publishing threshold(21:32) Challenges and philosophies(26:26) The effect of notes on re-sharing content(29:41) Origin story(35:46) Embracing small teams for big impact(40:23) The thermal project approach(47:47) Algorithm development and internal competitions(50:34) An inside look at how the team operates(58:56) Working with Elon(01:05:30) Launching Birdwatch(01:10:48) The core principles behind Community Notes(01:26:15) Anonymity and pseudonymity in contributions(01:32:17) Sustaining the project through leadership changes(01:37:57) Future directions for Community Notes(01:42:12) Final thoughts and optimism for the future—Referenced:• Community Notes on X: https://x.com/CommunityNotes• Sign up to be a Community Notes contributor: https://communitynotes.x.com/guide/en/contributing/signing-up• The Making of Community Notes: https://asteriskmag.com/issues/08/the-making-of-community-notes• “Readers added a Community Note to this Tweet”: https://x.com/HelpfulNotes/status/1718103364792205704• Note-ranking algorithm: https://communitynotes.x.com/guide/en/under-the-hood/ranking-notes#matrix-factorization• Study: Community Notes on X could be key to curbing misinformation: https://giesbusiness.illinois.edu/news/2024/11/18/study--community-notes-on-x-could-be-key-to-curbing-misinformation• Study Finds X’s (Formerly Twitter’s) Community Notes Provide Accurate, Credible Answers to Vaccine Misinformation: https://qi.ucsd.edu/study-finds-xs-formerly-twitters-community-notes-provide-accurate-credible-answers-to-vaccine-misinformation/• Did the Roll-Out of Community Notes Reduce Engagement with Misinformation on X/Twitter?: https://dl.acm.org/doi/10.1145/3686967• Kayvon Beykpour on LinkedIn: https://www.linkedin.com/in/kayvz/• Jack Dorsey on X: https://x.com/jack• “Birdwatch gives me the creeps” tweet: https://x.com/elonmusk/status/1589454464611540992• Blake Scholl on LinkedIn: https://www.linkedin.com/in/blakescholl/• Creating Truthtelling Incentives with the Bayesian Truth Serum: https://www.eecs.harvard.edu/cs286r/courses/fall12/papers/DW08.pdf• Asana: https://asana.com/• Spaces: https://blog.x.com/en_us/topics/product/2021/spaces-is-here• Amazon MTurk: https://www.mturk.com/• Community notes on GitHub: https://github.com/twitter/communitynotes• What do I think about Community Notes?: https://vitalik.eth.limo/general/2023/08/16/communitynotes.html• X’s community-led approach: tackling inaccurate and misleading information: https://blog.x.com/en_us/topics/company/2023/xs-community-led-approach-tackling-inaccurate-and-misleading-information• Linda Yaccarino on LinkedIn: https://www.linkedin.com/in/lindayaccarino/• Messi-Ronaldo rivalry: https://en.wikipedia.org/wiki/Messi%E2%80%93Ronaldo_rivalry• Supernotes paper: https://arxiv.org/pdf/2411.06116v1—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. Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe

Bob Moesta, co-creator of the Jobs to Be Done framework, recently published a new book, Job Moves. Drawing from interviews with over 1,000 people about their career transitions, it offers a practical playbook for career development. In our conversation, we discuss:• The four different “quests” that drive career changes• Why job features (salary, title) matter less than experiences• How to identify what gives you energy vs. drains you• The power of taking a “jobcation”• A template for crafting your career story• Tips for hiring and retaining great talent• The importance of prototyping potential careers• Much more—Brought to you by:• Eppo—Run reliable, impactful experiments• Vanta—Automate compliance. Simplify security• OneSchema—Import CSV data 10x faster—Find the transcript at: https://www.lennysnewsletter.com/p/how-to-find-work-you-love-bob-moesta—Where to find Bob Moesta:• X: https://x.com/bmoesta• LinkedIn: https://www.linkedin.com/in/bobmoesta/• Website: https://www.jobmoves.com/• Podcast: https://pca.st/gg6goo1n• The Re-Wired Group: https://therewiredgroup.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) Bob's background(05:10) Bob’s new book, Job Moves(09:31) Job features vs. job experiences(11:16) Four reasons people leave jobs(17:20) Energy drivers and energy drains(31:05) Prototyping your next job(34:32) Pushes and pulls(40:01) Understanding that no job is perfect(43:18) Taking a jobcation(51:22) Finding the right next step(55:18) Navigating job applications and interviews(58:28) How to craft your career story(01:04:04) Strengths and weaknesses: leveraging your superpowers(01:06:21) Hiring and writing job descriptions(01:11:20) Self-awareness and founding a startup(01:21:24) Conclusion and final thoughts—Referenced:• The ultimate guide to JTBD | Bob Moesta (co-creator of the framework): https://www.lennysnewsletter.com/p/the-ultimate-guide-to-jtbd-bob-moesta• Ethan S. Bernstein on LinkedIn: https://www.linkedin.com/in/ethanbernstein/• National Geographic: https://www.nationalgeographic.com/• Radical Candor: From theory to practice with author Kim Scott: https://www.lennysnewsletter.com/p/radical-candor-from-theory-to-practice• Building a long and meaningful career | Nikhyl Singhal (Meta, Google): https://www.lennysnewsletter.com/p/building-a-long-and-meaningful-career• The Story Spine (also known as Pixar’s Story Structure): https://www.storyprompt.com/blog/the-story-spine-also-known-as-pixars-story-structure• Tobi Lütke on LinkedIn: https://www.linkedin.com/in/tobiaslutke• Job Moves resources: https://www.jobmoves.com/resources• Why Employees Quit: https://hbr.org/2024/11/why-employees-quit—Recommended book:• Job Moves: 9 Steps for Making Progress in Your Career: https://www.amazon.com/Job-Moves-Making-Progress-Career/dp/0063283581—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. Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe

Uri Levine is a co-founder of Waze (which was acquired by Google for $1.3 billion in 2013), along with nine other companies (including another company he sold for over $1 billion). He’s also been on 20 boards and has been an advisor to over 50 startups. He recently released a new chapter of his best-selling book Fall in Love with the Problem, Not the Solution, which provides a guide to surviving crises at your company. In this episode, we cover:• The two types of startup crisis and how to handle them• Why speed of action is the most important thing• How to keep your team motivated when things look dire• A framework for deciding whether or not to pivot• What to do when product-market fit disappears• How to approach raising money during a crisis• More—Brought to you by:• WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs• Rippling—Automate HR, IT, and finance so you can scale faster• OneSchema—Import CSV data 10x faster—Find the transcript at: https://www.lennysnewsletter.com/p/a-founders-guide-to-crisis-management-uri-levine—Where to find Uri Levine:• X: https://twitter.com/urilevine1• LinkedIn: https://www.linkedin.com/in/uri-levine• Website: https://urilevine.com• Book: https://www.amazon.com/Fall-Love-Problem-Solution-Entrepreneurs/dp/1637746601/ref=tmm_pap_swatch_0?_encoding=UTF8&qid=&sr=—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, Uri!(05:10) The new chapter: navigating crises(08:15) Types of crises founders face(29:10) Navigating cash crises(38:31) The importance of never giving up(46:26) How to keep people engaged through a crises(47:59) Transparency in crisis management(56:58) Navigating product-market-fit challenges(59:27) Deciding when to pivot or shut down(01:13:34) Real-life startup survival stories(01:17:06) Avoiding and preparing for crises(01:21:21) Final thoughts and book promotion—Referenced:• Waze: https://www.waze.com/• Moovit: https://en.wikipedia.org/wiki/Moovit• Order Chat: https://www.crunchbase.com/organization/order-chat• Fibo: https://finder.startupnationcentral.org/company_page/fibo• Behind the founder: Drew Houston (Dropbox): https://www.lennysnewsletter.com/p/behind-the-founder-drew-houston-dropbox• TomTom: https://www.tomtom.com/• Khosla Ventures: https://www.khoslaventures.com/• WeSki: https://www.weski.com/• Larry Silverstein: https://en.wikipedia.org/wiki/Larry_Silverstein• Oversee: https://oversee.biz/• Lessons from 1,000+ YC startups: Resilience, tar pit ideas, pivoting, more | Dalton Caldwell (Y Combinator, Managing Director): https://www.lennysnewsletter.com/p/lessons-from-1000-yc-startups• 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• Harley Finkelstein on LinkedIn: https://www.linkedin.com/in/harleyf/• Zip: https://zip.co/us• Qualcomm: https://www.qualcomm.com/• Einstein quote: https://www.brainyquote.com/quotes/albert_einstein_148788—Recommended book:• Fall in Love with the Problem, Not the Solution: A Handbook for Entrepreneurs (updated 2025 version): https://urilevine.com/book/#Pre-order—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. Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe

Karina Nguyen leads research at OpenAI, where she’s been pivotal in developing groundbreaking products like Canvas, Tasks, and the o1 language model. Before OpenAI, Karina was at Anthropic, where she led post-training and evaluation work for Claude 3 models, created a document upload feature with 100,000 context windows, and contributed to numerous other innovations. With experience as an engineer at the New York Times and as a designer at Dropbox and Square, Karina has a rare firsthand perspective on the cutting edge of AI and large language models. In our conversation, we discuss:• How OpenAI builds product• What people misunderstand about AI model training• Differences between how OpenAI and Anthropic operate• The role of synthetic data in model development• How to build trust between users and AI models• Why she moved from engineering to research• Much more—Brought to you by:• Enterpret—Transform customer feedback into product growth• Vanta—Automate compliance. Simplify security• Loom—The easiest screen recorder you’ll ever use—Find the transcript at: https://www.lennysnewsletter.com/p/why-soft-skills-are-the-future-of-work-karina-nguyen—Where to find Karina Nguyen:• X: https://x.com/karinanguyen_• LinkedIn: https://www.linkedin.com/in/karinanguyen28• Website: https://karinanguyen.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 Karina Nguyen(04:42) Challenges in model training(08:21) Synthetic data and its importance(12:38) Creating Canvas(18:33) Day-to-day operations at OpenAI(20:28) Writing evaluations(23:22) Prototyping and product development(26:57) Building Canvas and Tasks(33:34) Understanding the job of a researcher(35:36) The future of AI and its impact on work and education(42:15) Soft skills in the age of AI(47:50) AI’s role in creativity and strategy development(53:34) Comparing Anthropic and OpenAI(57:11) Innovations and future visions(01:07:13) The potential of AI agents(01:11:36) Final thoughts and career advice—Referenced:• What’s in your stack: The state of tech tools in 2025: https://www.lennysnewsletter.com/p/whats-in-your-stack-the-state-of• Anthropic: https://www.anthropic.com/• OpenAI: https://openai.com/• What is synthetic data—and how can it help you competitively?: https://mitsloan.mit.edu/ideas-made-to-matter/what-synthetic-data-and-how-can-it-help-you-competitively• GPQA: https://datatunnel.io/glossary/gpqa/• Canvas: https://openai.com/index/introducing-canvas/• Barret Zoph on LinkedIn: https://www.linkedin.com/in/barret-zoph-65990543/• Mira Murati on LinkedIn: https://www.linkedin.com/in/mira-murati-4b39a066/• JSON Schema: https://json-schema.org/• Anthropic—100K Context Windows: https://www.anthropic.com/news/100k-context-windows• Claude 3 Haiku: https://www.anthropic.com/news/claude-3-haiku• A.I. Chatbots Defeated Doctors at Diagnosing Illness: https://www.nytimes.com/2024/11/17/health/chatgpt-ai-doctors-diagnosis.html• Cursor: https://www.cursor.com/• How AI will impact product management: https://www.lennysnewsletter.com/p/how-ai-will-impact-product-management• Lee Byron on LinkedIn: https://www.linkedin.com/in/lee-byron/• GraphQL: https://graphql.org/• Claude in Slack: https://www.anthropic.com/claude-in-slack• Sam Altman on X: https://x.com/sama• Jakub Pachocki on LinkedIn: https://www.linkedin.com/in/jakub-pachocki/• Lennybot: https://www.lennybot.com/• ElevenLabs: https://elevenlabs.io/• Westworld on Prime Video: https://www.amazon.com/Westworld-Season-1/dp/B01N05UD06• A conversation with OpenAI’s CPO Kevin Weil, Anthropic’s CPO Mike Krieger, and Sarah Guo: https://www.youtube.com/watch?v=IxkvVZua28k• Tuple: https://tuple.app/• How Shopify builds a high-intensity culture | Farhan Thawar (VP and Head of Eng): https://www.lennysnewsletter.com/p/how-shopify-builds-a-high-intensity-culture-farhan-thawar—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. Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe

Tobi Lütke is the founder and CEO of Shopify, a $130 billion business that powers over 10% of all U.S. e-commerce. Starting as a snowboard shop in 2004, Shopify has become the leading commerce platform by consistently approaching problems differently. Tobi remains deeply technical, frequently coding alongside his team, and is known for his unique approach to leadership, product development, and company building. In our conversation, we discuss:• Why complexity kills entrepreneurship• How to develop and leverage your unique talent stack• How specifically Tobi approaches thinking from first principles• The importance of focusing on unquantifiable qualities like joy and delight• Why Tobi works backward from a 100-year vision• Why metrics should support decisions, not make them• The power of following your curiosity• What Tobi believes it takes to be a great product leader• Much more—Brought to you by:• Sinch—Build messaging, email, and calling into your product• Liveblocks—Ready-made collaborative features to drop into your product• Loom—The easiest screen recorder you’ll ever use—Find the transcript at: https://www.lennysnewsletter.com/p/tobi-lutkes-leadership-playbook—Where to find Tobi Lütke:• X: https://x.com/tobi• LinkedIn: https://www.linkedin.com/in/tobiaslutke/• Website: https://tobi.lutke.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) Welcome and introduction(04:17) The Tobi tornado(07:10) Maximizing human potential(11:05) Education and personal growth(16:47) Operating without KPIs(25:00) First-principles thinking(40:04) Remote work(45:59) Why Tobi never stopped coding(54:46) Embracing disagreement(01:01:27) The 100-year vision(01:09:29) Balancing tactics and positioning(01:17:15) Encouraging entrepreneurship(01:19:34) The power of good UX(01:28:42) The talent stack and unique opportunities(01:34:30) The role of passion in product development(01:36:39) Final thoughts and farewell—Referenced:• How Shopify builds a high-intensity culture | Farhan Thawar (VP and Head of Eng): https://www.lennysnewsletter.com/p/how-shopify-builds-a-high-intensity-culture-farhan-thawar• Breaking the rules of growth: Why Shopify bans KPIs, optimizes for churn, prioritizes intuition, and builds toward a 100-year vision | Archie Abrams (VP Product, Head of Growth at Shopify): https://www.lennysnewsletter.com/p/shopifys-growth-archie-abrams• The ultimate guide to performance marketing | Timothy Davis (Shopify): https://www.lennysnewsletter.com/p/performance-marketing-timothy-davis• Brandon Chu on building product at Shopify, how writing changed the trajectory of his career, the habits that make you a great PM, pros and cons of being a platform PM, how Shopify got through Covid: https://www.lennysnewsletter.com/p/brandon-chu-on-what-its-like-to-build• IRC: https://en.wikipedia.org/wiki/IRC• Goodhart’s law: https://en.wikipedia.org/wiki/Goodhart%27s_law• Glen Coates on LinkedIn: https://www.linkedin.com/in/glcoates/• How Shopify builds product: https://www.lennysnewsletter.com/p/how-shopify-builds-product• The Last Dance on Netflix: https://www.netflix.com/title/80203144• Autoregressive Models for Natural Language Processing: https://medium.com/@zaiinn440/autoregressive-models-for-natural-language-processing-b95e5f933e1f• Archimedean property: https://en.wikipedia.org/wiki/Archimedean_property• Tabula rasa: https://en.wikipedia.org/wiki/Tabula_rasa• Daniel Weinand on LinkedIn: https://www.linkedin.com/in/danielweinand/• World of Warcraft: https://worldofwarcraft.blizzard.com• Harley Finkelstein on LinkedIn: https://www.linkedin.com/in/harleyf/• Monorepo: https://en.wikipedia.org/wiki/Monorepo• The Sarbanes Oxley Act: https://sarbanes-oxley-act.com/• Shopify builds Shopify Balance with Stripe to give small businesses an easier way to manage money: https://stripe.com/customers/shopify• Stanford marshmallow experiment: https://en.wikipedia.org/wiki/Stanford_marshmallow_experiment• Brian Armstrong on LinkedIn: https://www.linkedin.com/in/barmstrong/• We are the Web: https://link.wired.com/public/32945405—Recommended books:• Finite and Infinite Games: https://www.amazon.com/Finite-Infinite-Games-James-Carse/dp/1476731713• The Infinite Game: https://www.amazon.com/Infinite-Game-Simon-Sinek/dp/073521350X/—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. Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe

Nan Yu is the head of product at Linear, one of the most beloved and fastest-growing B2B SaaS products out there today, and the gold standard for high-performing tech teams. In our conversation, we discuss:• Why speed and quality aren’t actually at odds• Linear’s unique approach to product development• Nan’s systematic approach to creativity• Linear’s philosophy on deadlines• The “double triangle” framework for product management• Nan’s approach to landing his dream product roles• Much more—Brought to you by:• Sinch—Build messaging, email, and calling into your product• Paragon—Ship every SaaS integration your customers want• Wix Studio—The web creation platform built for agencies—Find the transcript at: https://www.lennysnewsletter.com/p/linears-secret-to-building-beloved-b2b-products-nan-yu—Where to find Nan Yu:• X: https://x.com/thenanyu• LinkedIn: https://www.linkedin.com/in/thenanyu/—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 Nan Yu and Linear(04:54) Survey insights: Linear vs. Jira(07:51) The speed vs. quality myth(09:24) Building and iterating quickly(15:31) Avoiding bloat in enterprise software(23:57) Understanding user needs deeply(30:09) How to approach customer calls(34:10) Creating strong emotional hooks(40:31) Managing the product backlog(44:46) Systemizing creativity(48:16) Demo: Saving drafts in Linear(51:38) Breaking constraints and building at extremes(54:15) Adopting new tools(58:22) The “double triangle” framework for product management(01:04:23) Effective job-hunting strategies for PMs(01:09:15) Thoughts on deadlines(01:14:15) Lightning round—Referenced:• Jira: https://www.atlassian.com/software/jira• Linear: https://linear.app/• Patrick Collison’s post on X: https://x.com/patrickc/status/1869422495985750459• Magnus Carlsen on X: https://x.com/magnuscarlsen• Hikaru Nakamura on X: https://x.com/gmhikaru• Geoffrey Moore on finding your beachhead, crossing the chasm, and dominating a market: https://www.lennysnewsletter.com/p/geoffrey-moore-on-finding-your-beachhead• Customer Request feature on Linear: https://linear.app/customer-requests• Everlane: https://www.everlane.com/• Schlep Blindness: https://paulgraham.com/schlep.html• Linear’s triage tool: https://linear.app/docs/triage• Patrick Collison’s post about mental models on X: https://x.com/patrickc/status/1443215022029619200• Brian Chesky’s new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach• Unpacking Amazon’s unique ways of working | Bill Carr (author of Working Backwards): https://www.lennysnewsletter.com/p/unpacking-amazons-unique-ways-of• Mode: https://mode.com/• The Diplomat on Netflix: https://www.netflix.com/title/81288983• Sakura Micron pens: https://www.amazon.com/SAKURA-PIGMA-MICRON-ESSENTIAL-COLORS/dp/B07VJFXT3C/—Recommended books:• Crossing the Chasm: Marketing and Selling Disruptive Products to Mainstream Customers: https://www.amazon.com/Crossing-Chasm-3rd-Disruptive-Mainstream/dp/0062292986• The Design of Everyday Things: https://www.amazon.com/Design-Everyday-Things-Revised-Expanded/dp/0465050654/—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. Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe

Chandra Janakiraman is the chief product officer, executive vice president, and a board member at VRChat. Previously, he was a product leader at Meta, where he led Facebook’s social experience interfaces and Reality Labs’ growth; served as CPO at Headspace, where he helped relaunch the platform, driving a 4x subscriber boost; and was a GM at Zynga, delivering massive hit games that reached hundreds of millions. In our conversation, Chandra shares:• His playbook for developing a product strategy• The difference between “small s” and “big S” strategy• How to run strategy sprints• Who should be involved in strategy work• Common pitfalls in strategy development• The role of AI in future strategy development• More—Brought to you by:• Eppo—Run reliable, impactful experiments• Airtable ProductCentral—Launch to new heights with a unified system for product development• OneSchema—Import CSV data 10x faster—Find the transcript at: https://www.lennysnewsletter.com/p/an-operators-guide-to-product-strategy-chandra-janakiraman—Where to find Chandra Janakiraman:• LinkedIn: https://www.linkedin.com/in/chandramohanj/—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) Chandra’s background(04:47) The importance of strategy(12:40) Defining product strategy(15:42) Developing a winning strategy: an overview(18:51) The preparation phase(30:46) The strategy sprint process(45:51) The design sprint (51:19) Document writing(57:39) Rolling out your strategy(01:01:28) Resourcing and roadmapping(01:04:42) Strategy lessons from Zynga(01:11:34) Strategy lessons from Meta(01:15:55) Big S strategy(01:26:58) AI in strategy formulation(01:38:12) Final thoughts and lightning round—Referenced:• Headspace: https://www.headspace.com/• Good Strategy, Bad Strategy | Richard Rumelt: https://www.lennysnewsletter.com/p/good-strategy-bad-strategy-richard• 5 essential questions to craft a winning strategy | Roger Martin (author, advisor, speaker): https://www.lennysnewsletter.com/p/the-ultimate-guide-to-strategy-roger-martin• VRChat: https://hello.vrchat.com/• Andrew Chen on LinkedIn: https://www.linkedin.com/in/pmandrewchen/• Template: Working Backwards PR FAQ: https://www.workingbackwards.com/resources/working-backwards-pr-faq• How LinkedIn became interesting: The inside story | Tomer Cohen (CPO at LinkedIn): https://www.lennysnewsletter.com/p/how-linkedin-became-interesting-tomer-cohen• 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• Identify your bullseye customer in one day | Michael Margolis (UX Research Partner at Google Ventures): https://www.lennysnewsletter.com/p/finding-your-bullseye-customer-michael-margolis• Chandra’s flow chart: https://docs.google.com/document/d/1SLmQ0oRFadzJnNM3MJetnLUvB18U4W4GXU4KtJ2ujEQ/edit?tab=t.0• Chandra’s strategy template: https://docs.google.com/document/d/1iNeYUaMnpicvkpVZO-gj9cCxLeHfWN0xtGm_QoxgemE/edit?tab=t.0#heading=h.5d3jz6v86yrs• Zynga: https://www.zynga.com/• David Foster Wallace’s quote about water: https://www.goodreads.com/quotes/97082-there-are-these-two-young-fish-swimming-along-and-they• Oculus: https://en.wikipedia.org/wiki/Oculus• Elon Musk’s quote: https://www.youtube.com/shorts/wf8TadbGYok• Concept car: https://en.wikipedia.org/wiki/Concept_car• Acquired podcast: The Mark Zuckerberg interview: https://www.acquired.fm/episodes/the-mark-zuckerberg-interview• Armand Ruiz on LinkedIn: https://www.linkedin.com/in/armand-ruiz/• What is a multi-armed bandit? Full explanation: https://amplitude.com/explore/experiment/multi-armed-bandit• IF on Prime Video: https://www.amazon.com/IF-John-Krasinski/dp/B0CW19SCVW• Dune: Part 2 on AppleTV+: https://tv.apple.com/us/movie/dune-part-two/umc.cmc.363aycnv6vy9qgekvew6fveb9• Dune Prophecy on Max: https://www.max.com/shows/dune-prophecy-2024/57660b16-a32a-476f-89da-3302ac379e91• Capybara Go on the App Store: https://apps.apple.com/ph/app/capybara-go/id6596787726• Bluesky: https://bsky.app/• Steve Jobs: The Lost Interview on Prime Video: https://www.amazon.com/Steve-Jobs-Lost-Interview/dp/B01IJD1BES—Recommended books:• The Art of War: https://www.amazon.com/Art-War-Sun-Tzu/dp/1599869772• Competitive Strategy: Techniques for Analyzing Industries and Competitors: https://www.amazon.com/Competitive-Strategy-Techniques-Industries-Competitors/dp/0684841487/• Good Strategy Bad Strategy: The Difference and Why It Matters: https://www.amazon.com/Good-Strategy-Bad-Difference-Matters/dp/0307886239/• Playing to Win: How Strategy Really Works: https://www.amazon.com/Playing-Win-Strategy-Really-Works/dp/142218739X• Make Time: How to Focus on What Matters Every Day: https://www.amazon.com/Make-Time-Focus-Matters-Every/dp/0525572422• Sprint: https://www.amazon.com/SPRINT-Jake-Zeratsky-Knapp/dp/0593076117• Walt Disney: The Triumph of the American Imagination: https://www.amazon.com/Walt-Disney-Triumph-American-Imagination/dp/0679757473• Creativity, Inc.: Overcoming the Unseen Forces That Stand in the Way of True Inspiration: https://www.amazon.com/Creativity-Inc-Expanded-Overcoming-Inspiration/dp/0593594649/• The Ten Faces of Innovation: Strategies for Heightening Creativity: https://www.amazon.com/dp/0385512074—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. Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe

Elena Verna is one of Silicon Valley’s most sought-after growth advisors and operators. She previously led growth at companies like Amplitude, Miro, Dropbox, and SurveyMonkey and is currently doing full-time advising for high-growth tech companies. In our conversation, Elena and I discuss:• 10 growth tactics that never work• Her 3 favorite growth frameworks• How to increase your career optionality—Brought to you by:• Sinch—Build messaging, email, and calling into your product• Vanta—Automate compliance. Simplify security• OneSchema—Import CSV data 10x faster—Find the transcript at: https://www.lennysnewsletter.com/p/10-growth-tactics-that-never-work-elena-verna—Where to find Elena Verna:• Newsletter: https://www.elenaverna.com/• X: https://x.com/elenaverna• LinkedIn: https://www.linkedin.com/in/elenaverna—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, Elena!(06:02) Common mistakes growth teams make(08:31) #1: Hiring for growth roles too soon(15:09) #2: Hiring a head of growth to fix your problems(19:20) #3: Doing a rebrand to drive growth(25:11) #4: Obsessing over your competition(34:00) #5: Believing that your problems are unique(42:32) #6: Prioritizing other growth channels above earned channels(50:55) #7: Failing to evolve your growth model(01:01:06) #8: Not hiring advisors(01:05:55) #9: Over-experimenting(01:10:44) #10: Color optimizations, third-party signups, one-email wonders, and removing friction(01:15:00) Elena’s favorite growth frameworks(01:18:50) Contrarian corner: full-time jobs(01:26:05) Lightning round and final thoughts—Referenced:• Elena Verna on how B2B growth is changing, product-led growth, product-led sales, why you should go freemium not trial, what features to make free, and much more: https://www.lennysnewsletter.com/p/elena-verna-on-why-every-company• The ultimate guide to product-led sales | Elena Verna: https://www.lennysnewsletter.com/p/the-ultimate-guide-to-product-led• Six rules of hiring for growth: https://www.lennysnewsletter.com/p/hiring-growth• Figma: https://www.figma.com/• Miro: https://www.figma.com/• Notion: https://www.figma.com/• Carol Wong on LinkedIn: https://www.linkedin.com/in/carol-wong-14133927/• Dropbox: https://www.dropbox.com/• The Law of Shitty Clickthroughs: https://andrewchen.com/the-law-of-shitty-clickthroughs/• Miroverse: https://miro.com/miroverse/• GitHub: https://github.com/• My 9 Favorite Growth Frameworks: https://www.elenaverna.com/p/my-9-favorite-growth-frameworks• Growth Loops are the New Funnels: https://www.reforge.com/blog/growth-loops• Racecar Growth Framework: https://www.reforge.com/blog/racecar-growth-framework• The Adjacent User: https://andrewchen.com/the-adjacent-user-theory/• Unorthodox frameworks for growing your product, career, and impact | Bangaly Kaba (YouTube, Instagram, Facebook, Instacart): https://www.lennysnewsletter.com/p/frameworks-for-growing-your-career-bangaly-kaba• Why I’m Unquitting Full-Time Roles: https://www.elenaverna.com/p/why-im-unquitting-full-time-roles• Noah Smith’s newsletter: https://www.noahpinion.blog/• Beef on Netflix: https://www.netflix.com/title/81447461• Veep on Max: https://www.max.com/shows/veep/37cb4217-c710-4166-8e9f-352a61f2cd3a• The Last of Us on Max: https://www.max.com/shows/last-of-us/93ba22b1-833e-47ba-ae94-8ee7b9eefa9a• Heated boots: https://www.amazon.com/heated-boots/s?k=heated+boots• Airpods Max: https://www.apple.com/airpods-max/• Memes by Elena: https://www.elenaverna.com/p/ten-funniest-growth-memes—Recommended books:• Project Hail Mary: https://www.amazon.com/Project-Hail-Mary-Andy-Weir/dp/0593135229/• The Martian: https://www.amazon.com/Martian-Andy-Weir/dp/0553418025• We Are Legion (Bobiverse #1): https://www.amazon.com/We-Are-Legion-Bob-Bobiverse/dp/1680680587• Fire Upon the Deep: https://www.amazon.com/Fire-Upon-Deep-Zones-Thought/dp/0812515285—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed. Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe

Graham Weaver teaches a top-rated course at Stanford’s Graduate School of Business (GSB), where he often unexpectedly ends up helping students figure out what to do with their lives. He is also the founder and CEO of Alpine Investors, a people-driven private equity firm. In our conversation, we discuss:• Why everything worthwhile requires suffering• Why most people operate on autopilot, and how to break free• The “genie methodology” for discovering your true path• The Nine Lives exercise for exploring different life possibilities• How to overcome limiting beliefs that hold you back• Why “not now” is often just another way of saying “never”• More—Brought to you by:• Merge—A single API to add hundreds of integrations into your app• Persona—A global leader in digital identity verification• Liveblocks—Ready-made collaborative features to drop into your product—Find the transcript at: https://www.lennysnewsletter.com/p/how-to-break-out-of-autopilot-graham-weaver—Where to find Graham Weaver:• LinkedIn: https://www.linkedin.com/in/graham-weaver-2b79• Instagram: https://www.instagram.com/grahamcweaver• YouTube: https://www.youtube.com/@grahamcweaver• Website: https://www.grahamweaver.com• TikTok: https://www.tiktok.com/@grahamcweaver—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) Graham’s background(05:30) Helping students find their true path(07:40) The genie methodology(12:36) Breaking free from autopilot mode(17:54) Identifying and overcoming limiting beliefs(20:33) Teaching entrepreneurship and personal fulfillment(22:53) The reality of long-term success(35:14) The role of accountability and executive coaching(40:22) Daily goal setting for success(43:11) The Nine Lives framework(48:01) The dangers of the “not now” mentality(55:27) Navigating life’s transitions(57:19) Failure corner(01:00:24) When to quit and when to persevere(01:02:18) Final thoughts and lightning round—Referenced:• Setting Goals: Demystified: https://www.grahamweaver.com/blog/goals• Tony Robbins’s website: https://www.tonyrobbins.com• Alpine Investors: https://alpineinvestors.com• Stanford GSB Last Lecture 2024—How to Live Your Life at Full Power: https://www.grahamweaver.com/blog/stanford-graduate-business-school-last-lecture-2024• I turned 50 today. Here is the most important thing I learned in my first half century: https://www.grahamweaver.com/blog/turning-50• Where the Crawdads Sing on Prime Video: https://www.amazon.com/Where-Crawdads-Sing-Daisy-Edgar-Jones/dp/B0B5KBKDNL• Chilipad Cube Bed Cooling System: https://www.amazon.com/Chilipad-Cube-Bed-Cooling-System/dp/B07GT9MYRW• Sleepme OOLER Sleep System: https://www.amazon.com/OOLER-Sleep-System-Temperature-Integration/dp/B07RX8LT9G• Eightsleep: https://www.eightsleep.com• Howard Thurman’s quote: https://www.goodreads.com/quotes/6273-don-t-ask-what-the-world-needs-ask-what-makes-you—Recommended books:• Switch: How to Change Things when Change Is Hard: https://www.amazon.com/Switch-Change-Things-When-Hard/dp/0385528752• The Untethered Soul: The Journey Beyond Yourself: https://www.amazon.com/Untethered-Soul-Journey-Beyond-Yourself/dp/1572245379• Don’t Believe Everything You Think: Why Your Thinking Is the Beginning and End of Suffering: https://www.amazon.com/Dont-Believe-Everything-Think-Expanded/dp/B0D47VYQMY• How to Win Friends and Influence People: https://www.amazon.com/How-Win-Friends-Influence-People/dp/0671027034—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed. Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe