Lenny's Podcast: Product | Growth | Career

• Inside monday.com’s transformation: radical transparency, impact over output, and their path to $1B ARR | Daniel Lereya (Chief Product and Technology Officer)

  Daniel Lereya, the Chief Product and Technology Officer at monday.com, shares how he and his team realized they were being outpaced by competitors and how that realization completely transformed how they operate and allowed them to build a global powerhouse, doing over $1 billion in ARR, with 245,000 customers worldwide.What you’ll learn:1. How they used seemingly impossible goals, like building 25 new features in one month, to unlock bigger thinking on their team2. How sharing real-time metrics with the entire company—even during interviews—created a culture of accountability and alignment3. How focusing on impact, rather than just shipping features, has transformed the company’s culture4. The story behind monday.com’s decision to launch five new products simultaneously and how it redefined their market positioning5. How they use “traps” (timeboxed deadlines) to drive focus, avoid scope creep, and deliver faster6. Daniel’s personal journey of navigating impostor syndrome and scaling challenges, and the mental models he uses to stay grounded and effective—Brought to you by:• Enterpret—Transform customer feedback into product growth• Airtable ProductCentral—Launch to new heights with a unified system for product development• Vanta—Automate compliance. Simplify security—Where to find Daniel Lereya:• LinkedIn: https://www.linkedin.com/in/daniel-lereya-aa487646/—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 Daniel and monday.com(04:20) The pivotal moment: competitors shipping faster(08:50) Setting ambitious goals(17:44) Focusing on impact rather than features(27:07) Transforming your product quarterly(32:07) Scaling monday.com: challenges and strategies(39:14) How monday.com maintains transparency as a public company(45:40) The importance of taking risks(51:02) Counterintuitive lessons in product development(54:33) The value of timeboxing and deadlines(57:28) Embracing user feedback(59:54) Adapting leadership styles(01:04:43) Personal reflections on leadership(01:10:41) Handling crises and strategic planning(01:17:28) The role of AI in work and personal life(01:22:13) Final thoughts and lightning round—Referenced:• Monday.com: https://monday.com/• The basics of a monday.com board: https://support.monday.com/hc/en-us/articles/115005317249-The-basics-of-a-board• Eran Zinman on LinkedIn: https://www.linkedin.com/in/eranzinman/• Roy Mann on LinkedIn: https://www.linkedin.com/in/manroy/• Tal Harari on LinkedIn: https://www.linkedin.com/in/tal-harari-a2515215/• Four-minute mile: https://en.wikipedia.org/wiki/Four-minute_mile• A better way to plan, build, and ship products | Ryan Singer (creator of “Shape Up,” early employee at 37signals): https://www.lennysnewsletter.com/p/shape-up-ryan-singer• Brian Chesky’s new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach• AI blocks: https://support.monday.com/hc/en-us/articles/18433811274386-AI-Automation-blocks• Unpacking Amazon’s unique ways of working | Bill Carr (author of Working Backwards): https://www.lennysnewsletter.com/p/unpacking-amazons-unique-ways-of• Behind the founder: Drew Houston (Dropbox): https://www.lennysnewsletter.com/p/behind-the-founder-drew-houston-dropbox• SpaceX: https://www.spacex.com/• Why and how to lead with transparency: https://monday.com/blog/monday-insights/may-30th/• How to win in the AI era: Ship a feature every week, embrace technical debt, ruthlessly cut scope, and create magic your competitors can’t copy | Gaurav Misra (CEO and co-founder of Captions): https://www.lennysnewsletter.com/p/how-to-win-in-the-ai-era-gaurav-misra• This Week #5: Overcoming impostor syndrome, introducing growth to an org, and how to partner with your data scientist: https://www.lennysnewsletter.com/p/this-week-overcoming-impostor-syndrome• Sheryl Sandberg on LinkedIn: https://www.linkedin.com/in/sheryl-sandberg-5126652/• Bryan Johnson on LinkedIn: https://www.linkedin.com/in/bryanrjohnson/• ChatGPT: https://chatgpt.com/• Cursor: https://www.cursor.com/• How to build deeper, more robust relationships | Carole Robin (Stanford GSB professor, “Touchy Feely”): https://www.lennysnewsletter.com/p/build-robust-relationships-carole-robin• FIFA 22: https://store.playstation.com/en-us/concept/10002538/• Formula 1: Drive to Survive on Netflix: https://www.netflix.com/title/80204890• Google Photos: https://photos.google.com/—Recommended books:• Shape Up: Stop Running in Circles and Ship Work that Matters: https://basecamp.com/shapeup• Working Backwards: Insights, Stories, and Secrets from Inside Amazon: https://www.amazon.com/Working-Backwards-Insights-Stories-Secrets/dp/1250267595• No Rules Rules: Netflix and the Culture of Reinvention: https://www.amazon.com/No-Rules-Netflix-Culture-Reinvention/dp/1984877860• Nonviolent Communication: A Language of Life: Life-Changing Tools for Healthy Relationships: https://www.amazon.com/Nonviolent-Communication-Language-Life-Changing-Relationships/dp/189200528X/—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].—Lenny may be an investor in the companies discussed. Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe

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• Announcing a brand-new podcast: “How I AI” with Claire Vo 🔥

  AI is rapidly changing how we live and work. It’s exciting, but also overwhelming. If you’re struggling to keep up, and wondering how to actually use these magical new tools to improve the quality and efficiency of your work, I’m thrilled to introduce How I AI with Claire Vo—the first ever new podcast under the Lenny’s Podcast network. Claire is an engineer, three-time CPO, and AI builder. In each episode, her guest shows you a specific, practical, and impactful way they’ve learned to use AI. Forget theoretical debates—this podcast is about real, valuable use cases. Expect 30-minute episodes, live demos, and tips/tricks/workflows you can implement immediately. Whether you’re building products, leading teams, or just looking to level up your AI skills, How I AI is for you.—SUBSCRIBE TO THE SHOW→ YouTube: ⁠https://www.youtube.com/channel/UCRYY7IEbkHLH_ScJCu9eWDQ⁠→ Spotify: ⁠https://open.spotify.com/show/4aRP2XSavdtrLG5FZoonOK→ Apple: https://podcasts.apple.com/us/podcast/how-i-ai/id1809663079 Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe

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• Building a magical AI code editor used by over 1 million developers in four months: The untold story of Windsurf | Varun Mohan (co-founder & CEO)

  Varun Mohan is the co-founder and CEO of Windsurf (formerly Codeium), an AI-powered development environment (IDE) that has been used by over 1 million developers in just four months and has quickly emerged as a leader in transforming how developers build software. Prior to finding success with Windsurf, the company pivoted twice—first from GPU virtualization infrastructure to an IDE plugin, and then to their own standalone IDE.In this conversation, you'll learn:1. Why Windsurf walked away from a profitable GPU infrastructure business and bet the company on helping engineers code2. The surprising UI discovery that tripled adoption rates overnight.3. The secret behind Windsurf's B2B enterprise plan, and why they invested early in an 80-person sales team despite conventional startup wisdom.4. How non-technical staff at Windsurf built their own custom tools instead of purchasing SaaS products, saving them over $500k in software costs5. Why Varun believes 90% of code will be AI-generated, but engineering jobs will actually increase6. How training on millions of incomplete code samples gives Windsurf an edge, and creates a moat long-term7. Why agency is the most undervalued and important skill in the AI era—Brought to you by:• Brex—The banking solution for startups• Productboard—Make products that matter• Coda—The all-in-one collaborative workspace—Where to find Varun Mohan:• X: https://x.com/_mohansolo• LinkedIn: https://www.linkedin.com/in/varunkmohan/—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) Varun’s background(03:57) Building and scaling Windsurf(12:58) Windsurf: The new purpose-built IDE to harness magic(17:11) The future of engineering and AI(21:30) Skills worth investing in(23:07) Hiring philosophy and company culture(35:22) Sales strategy and market position(39:37) JetBrains vs. VS Code: extensibility and enterprise adoption(41:20) Live demo: building an Airbnb for dogs with Windsurf(42:46) Tips for using Windsurf effectively(46:38) AI’s role in code modification and review(48:56) Empowering non-developers to build custom software(54:03) Training Windsurf(01:00:43) Windsurf’s unique team structure and product strategy(01:06:40) The importance of continuous innovation(01:08:57) Final thoughts and advice for aspiring developers—Referenced:• Windsurf: https://windsurf.com/• VS Code: https://code.visualstudio.com/• JetBrains: https://www.jetbrains.com/• Eclipse: https://eclipseide.org/• Visual Studio: https://visualstudio.microsoft.com/• Vim: https://www.vim.org/• Emacs: https://www.gnu.org/software/emacs/• Lessons from a two-time unicorn builder, 50-time startup advisor, and 20-time company board member | Uri Levine (co-founder of Waze): https://www.lennysnewsletter.com/p/lessons-from-uri-levine• IntelliJ: https://www.jetbrains.com/idea/• Julia: https://julialang.org/• Parallel computing: https://en.wikipedia.org/wiki/Parallel_computing• Douglas Chen on LinkedIn: https://www.linkedin.com/in/douglaspchen/• Carlos Delatorre on LinkedIn: https://www.linkedin.com/in/cadelatorre/• MongoDB: https://www.mongodb.com/• Cursor: https://www.cursor.com/• GitHub Copilot: https://github.com/features/copilot• Llama: https://www.llama.com/• Mistral: https://mistral.ai/• Building Lovable: $10M ARR in 60 days with 15 people | Anton Osika (CEO and co-founder): https://www.lennysnewsletter.com/p/building-lovable-anton-osika• 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• Behind the product: Replit | Amjad Masad (co-founder and CEO): https://www.lennysnewsletter.com/p/behind-the-product-replit-amjad-masad• React: https://react.dev/• Sonnet: https://www.anthropic.com/claude/sonnet• OpenAI: https://openai.com/• FedRamp: https://www.fedramp.gov/• Dario Amodei on LinkedIn: https://www.linkedin.com/in/dario-amodei-3934934/• Amdahl’s law: https://en.wikipedia.org/wiki/Amdahl%27s_law• How to win in the AI era: Ship a feature every week, embrace technical debt, ruthlessly cut scope, and create magic your competitors can't copy | Gaurav Misra (CEO and co-founder of Captions): https://www.lennysnewsletter.com/p/how-to-win-in-the-ai-era-gaurav-misra—Recommended book:• Fall in Love with the Problem, Not the Solution: A Handbook for Entrepreneurs: https://www.amazon.com/Fall-Love-Problem-Solution-Entrepreneurs/dp/1637741987—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].—Lenny may be an investor in the companies discussed. Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe

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• Everyone’s an engineer now: Inside v0’s mission to create a hundred million builders | Guillermo Rauch (founder & CEO of Vercel, creators of v0 and Next.js)

  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 [email protected].—Lenny may be an investor in the companies discussed. Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe

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  1:27:44
• OpenAI’s CPO on how AI changes must-have skills, moats, coding, startup playbooks, more | Kevin Weil (CPO at OpenAI, ex-Instagram, Twitter)

  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 [email protected].—Lenny may be an investor in the companies discussed. Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe

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  1:31:41

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