Lenny's Podcast: Product | Career | Growth

Lenny Rachitsky

Interviews with world-class product leaders and growth experts to uncover concrete, actionable, and tactical advice to help you build, launch, and grow your own product.

  1. 13H AGO

    The one question that saves product careers | Matt LeMay

    Matt LeMay spent 13 years as a music critic at Pitchfork before becoming one of product management’s most influential voices. He’s consulted with companies from startups to Fortune 500s and authored two essential PM books, including Impact-First Product Teams. After watching countless product teams get laid off despite “doing everything right,” he discovered a harsh truth: most PMs are optimizing for the wrong things. In this conversation, you’ll learn: 1. The one question that predicts if your team will survive the next layoffs (and why most teams can’t answer it) 2. Why following product “best practices” perfectly can actually accelerate your path to unemployment 3. The “low-impact PM death spiral”—how teams accidentally make themselves irrelevant 4. How to push back on executives without saying “no” (the options, plus a recommendation framework) 5. The counterintuitive reason why the happiest PMs are also the most commercially minded 6. The Liz Phair review that made Matt an internet villain for 22 years—and what it taught him about product management — Brought to you by: Enterpret—Transform customer feedback into product growth: https://enterpret.com/lenny Pragmatic Institute—Industry‑recognized product, marketing, and AI training & certifications: https://pragmaticinstitute.com/lenny Claude.ai—The AI for problem solvers and enterprise: http://claude.ai/ — Transcript: https://www.lennysnewsletter.com/p/the-one-question-that-saves-product-careers-matt-lemay — My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/168109376/my-biggest-takeaways-from-this-conversation — Where to find Matt LeMay: • Instagram: https://www.instagram.com/mttlmy • LinkedIn: https://www.linkedin.com/in/mattlemay/ • Website: https://mattlemay.com/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction to Matt LeMay (04:23) Matt’s background and transition to product management (06:47) The goal of Matt's new book (12:00) How to stress test your thinking as a PM (15:32) Thinking like the CEO (17:33) The role of a product manager (23:36) The low-impact PM death spiral (27:47) Case study: Mailchimp’s transition to a platform company (32:53) Radical acceptance (41:24) Embracing constraints in product management (44:23) Steps to become an impact-first product team (49:38) Setting effective goals (01:02:15) Prioritization and impact estimation (01:07:58) Navigating stakeholder management (01:12:35) Summarizing the 3 steps (01:16:36) Lightning round and final thoughts — Referenced: • Pitchfork: https://pitchfork.com/ • Daniel Ek’s memo: https://newsroom.spotify.com/2023-12-04/an-update-on-december-2023-organizational-changes/ • How to create a winning product strategy | Melissa Perri: https://www.lennysnewsletter.com/p/how-to-create-a-winning-product-strategy • Everything you’ve ever wanted to know about SAFe and the product owner role | Melissa Perri (author, founder of Product Institute): https://www.lennysnewsletter.com/p/product-owners-melissa-perri • Mailchimp: https://mailchimp.com/ • Intuit: https://www.intuit.com/ • Natalia Williams on LinkedIn: https://www.linkedin.com/in/nataliatwilliams/ • The ultimate guide to OKRs | Christina Wodtke (Stanford): https://www.lennysnewsletter.com/p/the-ultimate-guide-to-okrs-christina • Miro: https://miro.com/ • Prioritizing: https://www.lennysnewsletter.com/p/prioritizing • Temptation Island on Netflix: https://www.netflix.com/title/81744518 • Mark L. Walberg’s website: https://markwalbergtv.com/about • Antiques Roadshow on PBS: https://www.pbs.org/wgbh/roadshow/ • Milkman amp: https://milkmansound.com/collections/amplifiers/products/the-amp • Matt’s review of Liz Phair’s self-titled album: https://pitchfork.com/reviews/albums/6255-liz-phair/ • Pitchfork Critic Apologizes for Bashing Liz Phair Album; Singer Graciously Accepts: https://variety.com/2019/music/news/pitchfork-critic-apologizes-liz-phair-album-review-zero-score-1203326897/ • RedMonk: https://redmonk.com/ — Recommended books: • Product Management in Practice: A Practical, Tactical Guide for Your First Day and Every Day After: https://www.amazon.com/Product-Management-Practice-Practical-Tactical/dp/1098119738/r • Impact-First Product Teams: Define Success. Do Work That Matters. Be Indispensable.: https://www.amazon.com/Impact-first-Product-Teams-Success-Indispensable/dp/B0DVH4R3QJ • Escaping the Build Trap: How Effective Product Management Creates Real Value: https://www.amazon.com/Escaping-Build-Trap-Effective-Management/dp/B08B46C8R1/ • Radical Focus: Achieving Your Most Important Goals with Objectives and Key Results: https://www.amazon.com/Radical-Focus-Achieving-Important-Objectives/dp/0996006028 • The Wisdom of Insecurity: A Message for an Age of Anxiety: https://www.amazon.com/Wisdom-Insecurity-Message-Age-Anxiety/dp/0307741206/ — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com. Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

    1h 32m

  2. 5D AGO

    Inside ChatGPT: The fastest growing product in history | Nick Turley (Head of ChatGPT at OpenAI)

    Nick Turley is Head of ChatGPT, the fastest-growing product in history, with 700 million weekly active users (10% of the world’s population). He was part of the original hackathon team that shipped ChatGPT in just 10 days, helped it grow from zero to billions in revenue, and leads product for what may be the most consequential product of our time. We recorded this the day before GPT-5 launched. We discuss: 1. The 10-day sprint from deciding to ship ChatGPT to Sam Altman’s tweet (and why it was originally called “Chat with GPT-3.5”) 2. How they ran a willingness-to-pay Van Westendorp survey in their Discord to decide on the $20/month price point that everyone copied 3. The “Is it maximally accelerated?” philosophy that drives OpenAI’s insane shipping velocity 4. Why ChatGPT’s retention curve “smiles”—users leave, then come back months later using it more 5. The accidental decisions that changed history, including not having a waitlist 6. The impact ChatGPT will have on SEO and product growth 7. The counterintuitive reason why shipping unpolished AI features beats waiting for perfection 8. Why ChatGPT intentionally shipped with that “ugly” model-chooser dropdown 9. How TikTok comments became a primary user research channel early on — Brought to you by: Orkes—The enterprise platform for reliable applications and agentic workflows: https://www.orkes.io/ Vanta—Automate compliance. Simplify security: https://vanta.com/lenny PostHog—How developers build successful products: https://posthog.com/lenny — Transcript: https://www.lennysnewsletter.com/p/inside-chatgpt-nick-turley — My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/170411252/my-biggest-takeaways-from-this-conversation — Where to find Nick Turley • X: https://x.com/nickaturley • LinkedIn: https://www.linkedin.com/in/nicholasturley/ • Website: https://nickturley.com/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction to Nick Turley (04:52) GPT-5 launch (09:13) The vision for ChatGPT and AI assistants (13:52) The early days of ChatGPT (17:14) The success and impact of ChatGPT (20:44) Product development and iteration (23:11) Maximally accelerated: the OpenAI approach (26:17) Retention and user engagement (33:42) The future of chat interfaces (36:31) The evolution of ChatGPT (38:52) Subscription model and pricing strategies (42:10) Enterprise adoption and challenges (44:10) Balancing multiple product lines (52:13) Emergent use cases and user feedback (01:02:15) OpenAI’s unique product development approach (01:05:07) The importance of team composition (01:08:50) Balancing speed and quality in AI development (01:14:23) The role of evals in product development (01:16:13) The future of AI-driven content and GPTs (01:21:51) Philosophy and product leadership (01:23:47) Career journey and advice (01:27:49) Lightning round and final thoughts — References: https://www.lennysnewsletter.com/p/inside-chatgpt-nick-turley — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com. Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

    1h 36m
  3. Brian Chesky's secret mentor who died 9 times, started the Burning Man board, and built the world's first midlife wisdom school | Chip Conley (founder of MEA)

    AUG 3

    Brian Chesky's secret mentor who died 9 times, started the Burning Man board, and built the world's first midlife wisdom school | Chip Conley (founder of MEA)

    Chip Conley is the founder of Joie de Vivre hotels, the second-largest boutique hotel brand in the world. At age 52, he joined Airbnb as Head of Global Hospitality and Strategy, reporting to CEO Brian Chesky, who was 21 years younger. He earned the title of Airbnb’s “Modern Elder” by guiding the young founders on leadership and culture while learning Silicon Valley’s tech mindset himself. Today, Chip leads the Modern Elder Academy, the world’s first midlife wisdom school, and is the author of best-selling books like Wisdom@Work and Peak. He champions the idea that age and experience are assets—and that midlife can be a launchpad for renewed purpose and impact. In this conversation, we discuss: 1. The reality of Brian Chesky in “founder mode”—the good, bad, and stressful 2. How Chip went from running 52 boutique hotels to becoming Airbnb’s in-house mentor in his 50s 3. The “mentor and intern” mindset: how to simultaneously teach others and stay curious like a beginner 4. Why AI might actually favor older workers (hint: human wisdom vs. artificial intelligence) 5. His framework for navigating midlife transitions and finding meaning after 40 6. Specific tactics for older professionals to thrive in tech companies 7. Surprising data that midlife is often the happiest time of life—and how to leverage your 40s, 50s, and beyond 8. Chip’s formula for managing anxiety and fear (and how to regain control when worry strikes) — Brought to you by: Great Question—Empower everyone to run great research: https://www.greatquestion.com/lenny Vanta—Automate compliance. Simplify security: https://vanta.com/lenny Coda—The all-in-one collaborative workspace: https://coda.io/lenny — Transcript: https://www.lennysnewsletter.com/p/chip-conley — My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/168435278/my-biggest-takeaways-from-this-conversation — Where to find Chip Conley: • LinkedIn: https://www.linkedin.com/in/chipconleysf/ • Website: https://chipconley.com/ • Modern Elder Academy: https://www.meawisdom.com/ • Podcast: https://www.meawisdom.com/podcast/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction to Chip Conley (04:09) Chip’s journey with Airbnb (10:35) Insights on working with Brian Chesky (19:56) The value of intergenerational collaboration (25:57) Addressing ageism in tech (41:33) Chip’s early career and founding Joie de Vivre (43:54) A life-changing near-death experience (46:39) The importance of company culture (55:57) The Modern Elder Academy (59:21) The upside of aging (01:06:53) AI in daily life (01:09:14) Lightning round and final thoughts — Referenced: • Brian Chesky on LinkedIn: https://www.linkedin.com/in/brianchesky/ • Brian Chesky’s new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach • Natalie Tucci on LinkedIn: https://www.linkedin.com/in/natalietuccishoff/ • Laura Modi on LinkedIn: https://www.linkedin.com/in/laurahughes6/ • How to build a cult-like brand | Laura Modi (Bobbie): https://www.lennysnewsletter.com/p/from-growth-to-slowth-the-making • George Tenet: https://en.wikipedia.org/wiki/George_Tenet • Joie de Vivre Hospitality: https://www.hyatt.com/jdv-by-hyatt/en-US • Fest300: https://en.wikipedia.org/wiki/Fest300 • John Q. Smith on LinkedIn: https://www.linkedin.com/in/johnqsmith/ •Will A.I. Replace New Hires or Middle Managers?: https://www.nytimes.com/2025/07/07/business/ai-job-cuts.html • Burning Man: https://burningman.org/ • Sheryl Sandberg on LinkedIn: https://www.linkedin.com/in/sheryl-sandberg-5126652/ • Bill Graham: https://en.wikipedia.org/wiki/Bill_Graham_(promoter) • Maslow’s hierarchy: https://en.wikipedia.org/wiki/Maslow%27s_hierarchy_of_needs • Measuring what makes life worthwhile: https://www.ted.com/talks/chip_conley_measuring_what_makes_life_worthwhile • Jonathan Mildenhall on LinkedIn: https://www.linkedin.com/in/mildenhall/ • Becca Levy’s website: https://becca-levy.com/ • Kabuki Springs & Spa: https://kabukisprings.com/ • How positive age beliefs can support positive health outcomes with Becca Levy, PhD: https://www.ama-assn.org/delivering-care/population-care/how-positive-age-beliefs-can-support-positive-health-outcomes-becca • The U-shape of Happiness Across the Life Course: Expanding the Discussion: https://pmc.ncbi.nlm.nih.gov/articles/PMC7529452/ • The Midlife Unraveling: https://brenebrown.com/articles/2018/05/24/the-midlife-unraveling/ • Four Seasons: https://www.fourseasons.com/ • Blue Zones: https://www.bluezones.com/ • The Esalen Institute: https://www.esalen.org/ • Wisdom Well blog: https://www.meawisdom.com/wisdom-well/ • Elizabeth Gilbert TED Talk: Your elusive creative genius: https://www.ted.com/talks/elizabeth_gilbert_your_elusive_creative_genius • Ted Lasso on AppleTV+: https://tv.apple.com/us/show/ted-lasso/umc.cmc.vtoh0mn0xn7t3c643xqonfzy • I’ll Push You: https://www.illpushyou.com/ • Vuori shorts: https://vuoriclothing.com/collections/shorts • Fly Ranch: https://flyranch.burningman.org/ — Recommended books: • Wisdom at Work: The Making of a Modern Elder: https://www.amazon.com/Wisdom-Work-Making-Modern-Elder/dp/0525572902 • Range: Why Generalists Triumph in a Specialized World: https://www.amazon.com/Range-Generalists-Triumph-Specialized-World/dp/0735214484 • Peak: How Great Companies Get Their Mojo from Maslow: https://www.amazon.com/Peak-Great-Companies-Their-Maslow/dp/0787988618 • Learning to Love Midlife: 12 Reasons Why Life Gets Better with Age: https://www.amazon.com/Learning-Love-Midlife-Reasons-Better/dp/0316567027 • Man’s Search for Meaning: https://www.amazon.com/Mans-Search-Meaning-Viktor-Frankl/dp/0807060100/ • Emotional Equations: Simple Steps for Creating Happiness + Success in Business + Life: https://www.amazon.com/Emotional-Equations-Creating-Happiness-Business/dp/1451607261/ • Big Magic: Creative Living Beyond Fear: https://www.amazon.com/Big-Magic-Creative-Living-Beyond/dp/1594634726 — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com. Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

    1h 20m
  4. He saved OpenAI, invented the “Like” button, and built Google Maps: Bret Taylor on the future of careers, coding, agents, and more

    JUL 31

    He saved OpenAI, invented the “Like” button, and built Google Maps: Bret Taylor on the future of careers, coding, agents, and more

    Bret Taylor’s legendary career includes being CTO of Meta, co-CEO of Salesforce, chairman of the board at OpenAI (yes, during that drama), co-creating both Google Maps and the Like button, and founding three companies. Today he’s the founder and CEO of Sierra, an AI agent company transforming customer service. He’s one of the few people I’ve met who’s been wildly successful at every level—from engineer to C-suite executive to founder—and across almost every discipline, including PM, engineer, CTO, COO, CPO, CEO, and board member. In this conversation, you’ll learn: 1. The brutal product review that nearly ended his Google career—and how that failure led to creating Google Maps 2. The question Sheryl Sandberg taught him to ask every morning (“What’s the most impactful thing I can do today?”) that transformed how he approached every role 3. The three AI market segments that matter 4. Why AI agents will replace SaaS products 5. His framework for knowing whose advice to actually listen to—and how that came in handy during the OpenAI board drama 6. The counterintuitive go-to-market strategy most AI startups get wrong 7. Sierra’s outcome-based pricing model that’s transforming how enterprise software is sold (and why every SaaS company should adopt it) 8. What he’s teaching his kids about AI that every parent should know — Brought to you by: CodeRabbit—Cut code review time and bugs in half. Instantly: https://coderabbit.link/lenny Basecamp—The famously straightforward project management system from 37signals: https://www.basecamp.com/lenny Vanta—Automate compliance. Simplify security: https://vanta.com/lenny — Transcript: https://www.lennysnewsletter.com/p/he-saved-openai-bret-taylor — My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/168905359/my-biggest-takeaways-from-this-conversation — Where to find Bret Taylor: • X: https://x.com/btaylor • LinkedIn: https://www.linkedin.com/in/brettaylor/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction to Bret Taylor (04:10) Bret’s early career and first major mistake (08:24) The birth of Google Maps (11:57) Lessons from FriendFeed and the importance of honest feedback (31:30) The future of coding and AI’s role (45:26) Preparing the next generation for an AI-driven world (48:46) AI in education (52:05) Business strategies in the AI market (01:04:38) Outcome-based pricing in AI (01:09:15) Productivity gains and AI (01:17:35) Go-to-market strategies for AI products (01:21:49) Lightning round and final thoughts — Referenced: • Marissa Mayer on LinkedIn: https://www.linkedin.com/in/marissamayer/ • “Lazy Sunday”—SNL: https://www.youtube.com/watch?v=sRhTeaa_B98 • Quip: https://quip.com/ • Sierra: https://sierra.ai/ • FriendFeed: https://en.wikipedia.org/wiki/FriendFeed • Sheryl Sandberg on LinkedIn: https://www.linkedin.com/in/sheryl-sandberg-5126652/ • Jim Norris on LinkedIn: https://www.linkedin.com/in/halfspin/ • Paul Buchheit on X: https://x.com/paultoo • Sanjeev Singh on LinkedIn: https://www.linkedin.com/in/sanjeev-singh-20a1b72/ • Barack Obama: https://www.obamalibrary.gov/obamas/president-barack-obama • Oprah Winfrey: https://en.wikipedia.org/wiki/Oprah_Winfrey • Ashton Kutcher: https://en.wikipedia.org/wiki/Ashton_Kutcher • PayPal Mafia: https://en.wikipedia.org/wiki/PayPal_Mafia • Sam Altman on X: https://x.com/sama • Warren Buffett on X: https://x.com/warrenbuffett • Unix: https://en.wikipedia.org/wiki/Unix • Fortran: https://en.wikipedia.org/wiki/Fortran • C: https://en.wikipedia.org/wiki/C_(programming_language) • Python: https://www.python.org/ • Perl: https://www.perl.org/ • Rust: https://www.rust-lang.org/ • Eleven Labs: https://elevenlabs.io/ • The exact AI playbook (using MCPs, custom GPTs, Granola) that saved ElevenLabs $100k+ and helps them ship daily | Luke Harries (Head of Growth): https://www.lennysnewsletter.com/p/the-ai-marketing-stack • Confluent: https://www.confluent.io/ • Databricks: https://www.databricks.com/ • Snowflake: https://www.snowflake.com • Harvey: https://www.harvey.ai/ • Behind the founder: Marc Benioff: https://www.lennysnewsletter.com/p/behind-the-founder-marc-benioff • Larry Summers’s website: https://larrysummers.com/ • AutoCAD: https://www.autodesk.com/products/autocad/overview • Revit: https://www.autodesk.com/products/revit/ • The art and science of pricing | Madhavan Ramanujam (Monetizing Innovation, Simon-Kucher): https://www.amazon.com/Monetizing-Innovation-Companies-Design-Product/dp/1119240867 • Pricing your AI product: Lessons from 400+ companies and 50 unicorns | Madhavan Ramanujam: https://lenny.substack.com/p/pricing-and-scaling-your-ai-product-madhavan-ramanujam • Cursor: https://cursor.com/ • CodeX: https://openai.com/codex/ • Claude Code: https://www.anthropic.com/claude-code • The rise of Cursor: The $300M ARR AI tool that engineers can’t stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell • DirecTV: https://www.directv.com/ • SiriusXM: https://www.siriusxm.com/ • Wayfair: https://www.wayfair.com/ • Akai: https://www.akaipro.com/ • Chubbies Shorts: https://www.chubbiesshorts.com/ • Weight Watchers: https://www.weightwatchers.com/ • CLEAR: https://www.clearme.com/ • Stripe: https://stripe.com/ • Building product at Stripe: craft, metrics, and customer obsession | Jeff Weinstein (Product lead): https://www.lennysnewsletter.com/p/building-product-at-stripe-jeff-weinstein • Twilio: https://www.twilio.com/ • ServiceNow: https://www.servicenow.com/ • Adobe: https://www.adobe.com/ • Jobs to be done: https://jobs-to-be-done.com/jobs-to-be-done-a-framework-for-customer-needs-c883cbf61c90 • The ultimate guide to JTBD | Bob Moesta (co-creator of the framework): https://www.lennysnewsletter.com/p/the-ultimate-guide-to-jtbd-bob-moesta • Inception: https://www.imdb.com/title/tt1375666/ • Alan Kay’s quote: https://www.brainyquote.com/quotes/alan_kay_100831 • Jobs at Sierra: https://sierra.ai/careers — Recommended books: • Monetizing Innovation: How Smart Companies Design the Product Around the Price: https://www.amazon.com/Monetizing-Innovation-Companies-Design-Product/dp/1119240867 • Competing Against Luck: The Story of Innovation and Customer Choice: https://www.amazon.com/Competing-Against-Luck-Innovation-Customer/dp/0062435612 • Endurance: Shackleton’s Incredible Voyage: https://www.amazon.com/Endurance-Shackletons-Incredible-Alfred-Lansing/dp/0465062881 — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com. Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

    1h 29m
  5. Pricing your AI product: Lessons from 400+ companies and 50 unicorns | Madhavan Ramanujam

    JUL 27

    Pricing your AI product: Lessons from 400+ companies and 50 unicorns | Madhavan Ramanujam

    Madhavan Ramanujam is the world’s foremost expert on pricing and monetization strategy. As managing partner at Simon-Kucher, he helped over 250 companies, including 30 unicorns, architect their pricing strategies. He’s the author of the definitive book on pricing, Monetizing Innovation. Now he’s back with a sequel, Scaling Innovation, which reveals how to build enduring businesses by dominating both market share and wallet share. He recently left Simon-Kucher to launch his own fund, 49 Palms, focused on helping early-stage AI companies. In this conversation, we discuss: 1. The 2x2 framework that identifies your optimal pricing model 2. Why AI companies can capture 25% to 50% of value created, vs. 10% to 20% for traditional SaaS products 3. Why popular AI coding tools may have already doomed themselves with underpricing 4. The “give-and-get” framework top negotiators use to extract maximum value from every deal 5. The negotiation strategy that helped one founder 4x their deal size overnight 6. How to frame POCs as “business case creation” instead of technical demos (and why this changes everything) 7. Why AI companies must get monetization right from day one—not “figure it out later” 8. How companies like Intercom’s Fin and Sierra pioneered outcome-based pricing (charging $0.99 per AI resolution) 9. The single question that reveals if your pricing is too complex — Brought to you by: Enterpret—Transform customer feedback into product growth: https://enterpret.com/lenny DX—A platform for measuring and improving developer productivity: https://getdx.com/lenny Persona—A global leader in digital identity verification: https://withpersona.com/lenny — Transcript: https://www.lennysnewsletter.com/p/pricing-and-scaling-your-ai-product-madhavan-ramanujam — My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/168109183/my-biggest-takeaways-from-this-conversation — Where to find Madhavan Ramanujam: • X: https://x.com/madhavansf • LinkedIn: https://www.linkedin.com/in/madhavansf/ • Promo email for Scaling Innovation: promo@49palmsvc.com — If you’re purchasing more than five copies, send a screenshot of your receipt to enter Madhavan’s exclusive bundle raffle. — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction to Madhavan and his work (04:30) The core thesis of Scaling Innovation (09:20) Common traps founders fall into (12:06) Beautifully simple pricing (15:00) Mastering negotiations (26:51) Other strategies for effective pricing and monetization (27:35) How AI pricing is different (31:33) Handling POCs (36:25) The importance of mastering monetization (38:58) Choosing the right AI pricing model (43:13) Current trends in AI pricing (44:48) Strategizing for outcome-based models (50:23) Packaging strategies for scaling (51:37) Adapting pricing strategies over time (53:40) Key axioms for pricing success (58:00) Takeaways for founders (01:01:33) Lightning round and final thoughts — Referenced: • The art and science of pricing | Madhavan Ramanujam (Monetizing Innovation, Simon-Kucher): https://www.lennysnewsletter.com/p/the-art-and-science-of-pricing-madhavan • Cursor: https://www.cursor.com/ • The rise of Cursor: The $300M ARR AI tool that engineers can’t stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell • Sierra Finn: http://www.sierrafinn.com/ • Chargeflow: https://www.chargeflow.io/ • GitHub: https://github.com/ • Intercom: https://www.intercom.com/ • Warren Buffett’s quote: https://www.goodreads.com/quotes/11478913-if-you-ve-got-the-power-to-raise-prices-without-losing • Sierra: https://sierra.ai/ • Clay Bavor on LinkedIn: https://www.linkedin.com/in/claybavor/ • Mission: Impossible—The Final Reckoning: https://www.imdb.com/title/tt9603208/ • Delphi: https://www.delphi.ai/ • Dara Ladjevardian on LinkedIn: https://www.linkedin.com/in/dara-ladjevardian/ • Sam Spelsberg on LinkedIn: https://www.linkedin.com/in/samuel-spelsberg/ • Lennybot: https://www.lennybot.com/ • Granola: https://www.granola.ai/ • Simon-Kucher: https://www.simon-kucher.com/ • Josh Bloom on LinkedIn: https://www.linkedin.com/in/joshuabloompricingconsulting/ — Recommended books: • Monetizing Innovation: How Smart Companies Design the Product Around the Price: https://www.amazon.com/Monetizing-Innovation-Companies-Design-Product/dp/1119240867 • Scaling Innovation: How Smart Companies Architect Profitable Growth: https://www.amazon.com/dp/1119633060 • Business Model Generation: A Handbook for Visionaries, Game Changers, and Challengers: https://www.amazon.com/Business-Model-Generation-Visionaries-Challengers/dp/0470876417 • Thinking Fast and Slow: https://www.amazon.com/Thinking-Fast-Slow-Daniel-Kahneman/dp/0374533555/ • Contagious: Why Things Catch On: https://www.amazon.com/Contagious-Things-Catch-Jonah-Berger/dp/1451686587/ — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com. Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

    1h 12m
  6. Anthropic co-founder on quitting OpenAI, AGI predictions, $100M talent wars, 20% unemployment, and the nightmare scenarios keeping him up at night | Ben Mann

    JUL 20

    Anthropic co-founder on quitting OpenAI, AGI predictions, $100M talent wars, 20% unemployment, and the nightmare scenarios keeping him up at night | Ben Mann

    Benjamin Mann is a co-founder of Anthropic, an AI startup dedicated to building aligned, safety-first AI systems. Prior to Anthropic, Ben was one of the architects of GPT-3 at OpenAI. He left OpenAI driven by the mission to ensure that AI benefits humanity. In this episode, Ben opens up about the accelerating progress in AI and the urgent need to steer it responsibly. In this conversation, we discuss: 1. The inside story of leaving OpenAI with the entire safety team to start Anthropic 2. How Meta’s $100M offers reveal the true market price of top AI talent 3. Why AI progress is still accelerating (not plateauing), and how most people misjudge the exponential 4. Ben’s “economic Turing test” for knowing when we’ve achieved AGI—and why it’s likely coming by 2027-2028 5. Why he believes 20% unemployment is inevitable 6. The AI nightmare scenarios that concern him most—and how he believes we can still avoid them 7. How focusing on AI safety created Claude’s beloved personality 8. What three skills he’s teaching his kids instead of traditional academics — Brought to you by: Sauce—Turn customer pain into product revenue: https://sauce.app/lenny LucidLink—Real-time cloud storage for teams: https://www.lucidlink.com/lenny Fin—The #1 AI agent for customer service: https://fin.ai/lenny — Transcript: https://www.lennysnewsletter.com/p/anthropic-co-founder-benjamin-mann — My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/168107911/my-biggest-takeaways-from-this-conversation — Where to find Ben Mann: • X: https://x.com/8enmann • LinkedIn: https://www.linkedin.com/in/benjamin-mann/ • Website: https://benjmann.net/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction to Benjamin (04:43) The AI talent war (06:28) AI progress and scaling laws (10:50) Defining AGI and the economic Turing test (12:26) The impact of AI on jobs (17:45) Preparing for an AI future (24:05) Founding Anthropic (27:06) Balancing AI safety and progress (29:10) Constitutional AI and model alignment (34:21) The importance of AI safety (43:40) The risks of autonomous agents (45:40) Forecasting superintelligence (48:36) How hard is it to align AI? (53:19) Reinforcement learning from AI feedback (RLAIF) (57:03) AI's biggest bottlenecks (01:00:11) Personal reflections on responsibilities (01:02:36) Anthropic’s growth and innovations (01:07:48) Lightning round and final thoughts — Referenced: • Dario Amodei on LinkedIn: https://www.linkedin.com/in/dario-amodei-3934934/ • Anthropic CEO: AI Could Wipe Out 50% of Entry-Level White Collar Jobs: https://www.marketingaiinstitute.com/blog/dario-amodei-ai-entry-level-jobs • Alexa+: https://www.amazon.com/dp/B0DCCNHWV5 • Azure: https://azure.microsoft.com/ • Sam Altman on X: https://x.com/sama • Opus 3: https://www.anthropic.com/news/claude-3-family • Claude’s Constitution: https://www.anthropic.com/news/claudes-constitution • Greg Brockman on X: https://x.com/gdb • Anthropic’s Responsible Scaling Policy: https://www.anthropic.com/news/anthropics-responsible-scaling-policy • Agentic Misalignment: How LLMs could be insider threats: https://www.anthropic.com/research/agentic-misalignment • Anthropic’s CPO on what comes next | Mike Krieger (co-founder of Instagram): https://www.lennysnewsletter.com/p/anthropics-cpo-heres-what-comes-next • AI prompt engineering in 2025: What works and what doesn’t | Sander Schulhoff (Learn Prompting, HackAPrompt): https://www.lennysnewsletter.com/p/ai-prompt-engineering-in-2025-sander-schulhoff • Unitree: https://www.unitree.com/ • Arthur C. Clarke: https://en.wikipedia.org/wiki/Arthur_C._Clarke • How Reinforcement Learning from AI Feedback Works: https://www.assemblyai.com/blog/how-reinforcement-learning-from-ai-feedback-works • RLHF: https://en.wikipedia.org/wiki/Reinforcement_learning_from_human_feedback • Jared Kaplan on LinkedIn: https://www.linkedin.com/in/jared-kaplan-645843213/ • Moore’s law: https://en.wikipedia.org/wiki/Moore%27s_law • Machine Intelligence Research Institute: https://intelligence.org/ • Raph Lee on LinkedIn: https://www.linkedin.com/in/raphaeltlee/ • “The Last Question”: https://en.wikipedia.org/wiki/The_Last_Question • Beth Barnes on LinkedIn: https://www.linkedin.com/in/elizabethmbarnes/ • “The Last Question”: https://en.wikipedia.org/wiki/The_Last_Question • Good Strategy, Bad Strategy | Richard Rumelt: https://www.lennysnewsletter.com/p/good-strategy-bad-strategy-richard • Pantheon on Netflix: https://www.netflix.com/title/81937398 • Ted Lasso on AppleTV+: https://tv.apple.com/us/show/ted-lasso/umc.cmc.vtoh0mn0xn7t3c643xqonfzy • Kurzgesagt—In a Nutshell: https://www.youtube.com/channel/UCsXVk37bltHxD1rDPwtNM8Q • 5 tips to poop like a champion: https://8enmann.medium.com/5-tips-to-poop-like-a-champion-3292481a9651 — Recommended books: • Superintelligence: Paths, Dangers, Strategies: https://www.amazon.com/Superintelligence-Dangers-Strategies-Nick-Bostrom/dp/0198739834 • The Hacker and the State: Cyber Attacks and the New Normal of Geopolitics: https://www.amazon.com/Hacker-State-Attacks-Normal-Geopolitics/dp/0674987551 • Replacing Guilt: Minding Our Way: https://www.amazon.com/Replacing-Guilt-Minding-Our-Way/dp/B086FTSB3Q • Good Strategy/Bad Strategy: The Difference and Why It Matters: https://www.amazon.com/Good-Strategy-Bad-Difference-Matters/dp/0307886239 • The Alignment Problem: Machine Learning and Human Values: https://www.amazon.com/Alignment-Problem-Machine-Learning-Values/dp/0393635821 — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com. Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

    1h 15m
  7. The AI-native startup: 5 products, 7-figure revenue, 100% AI-written code | Dan Shipper (co-founder/CEO of Every)

    JUL 17

    The AI-native startup: 5 products, 7-figure revenue, 100% AI-written code | Dan Shipper (co-founder/CEO of Every)

    Dan Shipper is the co-founder and CEO of Every. With just 15 people, Every publishes a daily AI newsletter, ships multiple AI products, and operates a million-dollar-a-year consulting arm—all while their engineers write virtually zero code. It’s the most radical example of AI-first operations, and Dan is a prolific writer who has become a leading voice on how AI is transforming the way we build and work. Learn: 1. Why Dan thinks AI won’t steal jobs en masse—and may actually reshore many jobs to the U.S. 2. The most underrated AI tool for non-programmers 3. An inside look at Every’s AI-first workflow 4. Why every company needs an “AI operations lead” 5. How Dan’s team uses an arsenal of AI agents (Claude, Codex, “Friday,” “Charlie”) in parallel, treating each AI like a specialist with unique strengths 6. Why generalists will thrive in an AI-first world, as rigid job titles blur and everyone becomes a “manager” of AI tools 7. Dan’s playbook for making any company AI-first—from the CEO setting the example, to hosting internal prompt-sharing sessions, to upskilling teams on AI tools — Brought to you by: CodeRabbit—Cut code review time and bugs in half. Instantly: https://coderabbit.link/lenny DX—A platform for measuring and improving developer productivity: https://getdx.com/lenny PostHog—How developers build successful products: https://posthog.com/lenny — Transcript: https://www.lennysnewsletter.com/p/inside-every-dan-shipper — My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/167681269/my-biggest-takeaways-from-this-conversation — Where to find Dan Shipper: • X: https://x.com/danshipper • LinkedIn: https://www.linkedin.com/in/danshipper/ • Podcast: https://every.to/podcast — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Welcome and introduction (04:04) Hot takes on AI and job reshoring (07:06) The power of Claude Code for non-coders (14:35) The future of AI in business operations (18:45) AI’s role in enhancing human skills (22:26) The evolution of AI tools and their applications (25:40) Building an AI-first company (29:50) Innovative AI operations and team dynamics (35:35) Dan's AI stack (41:26) Compounding engineering (48:29) The impact of AI on learning and development (50:10) Accelerating career growth with AI (51:36) Revolutionizing code review and workflow (53:07) The importance of coding knowledge (57:26) Building AI-driven products (01:02:01) Innovative fundraising strategies (01:08:45) Consulting and AI adoption in companies (01:17:01) The allocation economy and future skills (01:20:12) The value of generalists in the AI age (01:24:07) Lightning round and final thoughts — Referenced: • Claude Code: https://www.anthropic.com/claude-code • Gemini CLI: https://blog.google/technology/developers/introducing-gemini-cli-open-source-ai-agent/ • Microsoft Copilot: https://copilot.microsoft.com/ • Cursor: https://www.cursor.com/ • Base44: https://base44.com/ • Solo founder, $80M exit, 6 months: The Base44 bootstrapped startup success story | Maor Shlomo: https://www.lennysnewsletter.com/p/the-base44-bootstrapped-startup-success-story-maor-shlomo • The rise of Cursor: The $300M ARR AI tool that engineers can’t stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell • Plato’s Argument Against Writing: https://fs.blog/an-old-argument-against-writing/ • From ChatGPT to Instagram to Uber: The quiet architect behind the world’s most popular products | Peter Deng: https://www.lennysnewsletter.com/p/the-quiet-architect-peter-deng • Granola: https://www.granola.ai/ • Tobi Lutke’s post on X about context engineering: https://x.com/tobi/status/1935533422589399127 • Tobi Lütke’s leadership playbook: Playing infinite games, operating from first principles, and maximizing human potential (founder and CEO of Shopify): https://www.lennysnewsletter.com/p/tobi-lutkes-leadership-playbook • Every: https://every.to/ • Cora: https://www.cora.computer/ • Sparkle: https://makeitsparkle.co/ • Spiral: https://spiral.computer/ • Lex: https://lex.page/ • Nathan Baschez on LinkedIn: https://www.linkedin.com/in/nbashaw/ • Kate Lee on LinkedIn: https://www.linkedin.com/in/kate-lee-506768/ • Katie Parrott on LinkedIn: https://www.linkedin.com/in/katieparrott/ • Animalz: https://www.animalz.co/ • Rachel Woods on X: https://x.com/rachel_l_woods • Nityesh Agarwal on LinkedIn: https://www.linkedin.com/in/nityeshaga • Claude Opus 4: https://www.anthropic.com/claude/opus • Codex: https://openai.com/index/introducing-codex/ • Superwhisper: https://superwhisper.com/ • Wispr Flow: https://wisprflow.ai/ • Notion: https://www.notion.com/ • Kieran Klaassen on LinkedIn: https://www.linkedin.com/in/kieran-klaassen/ • Friday: https://www.friday.run/ • Charlie: https://www.gocharlie.ai/product/ai-agents/ • Avengers: https://en.wikipedia.org/wiki/Avengers_(Marvel_Cinematic_Universe) • Alex Duffy on LinkedIn: https://www.linkedin.com/in/alex-d/ • Danny Aziz on LinkedIn: https://www.linkedin.com/in/dannyaziz/ • Dia: https://www.diabrowser.com/ • Reid Hoffman’s website: https://www.reidhoffman.org/ • Starting Line VC: https://www.startingline.vc/ • Walleye Capital: https://walleyecapital.com/ • At This $10 Billion Hedge Fund, Using AI Just Became Mandatory: https://every.to/podcast/at-this-10-billion-hedge-fund-using-ai-just-became-mandatory • Reflexive AI usage is now a baseline expectation at Shopify: https://x.com/tobi/status/1909251946235437514 • Klarna CEO Sebastian Siemiatkowski on Getting AI to Do the Work of 700 Customer Service Reps: https://www.sequoiacap.com/podcast/training-data-sebastian-siemiatkowski/ • The Pin Factory: https://www.adamsmithworks.org/pin_factory.html • Deadwood on HBO: https://www.hbo.com/deadwood • Joel Spolsky on X: https://x.com/spolsky • Jason Fried’s website: https://world.hey.com/jason • Jason Fried challenges your thinking on fundraising, goals, growth, and more: https://www.lennysnewsletter.com/p/jason-fried-challenges-your-thinking • Sam Harris’s website: https://www.samharris.org/ • Bill Simmons on X: https://x.com/billsimmons — Recommended books: • War and Peace: https://www.amazon.com/War-Peace-Vintage-Classics-Tolstoy/dp/1400079985 • Anna Karenina: https://www.amazon.com/Anna-Karenina-Leo-Tolstoy/dp/0143035002 • Playing and Reality: https://www.amazon.com/Playing-Reality-Routledge-Classics-86/dp/0415345464 • The Death of Ivan Ilyich: https://www.amazon.com/Death-Ivan-Ilyich-Leo-Tolstoy/dp/1468014315 • A Swim in a Pond in the Rain: https://www.amazon.com/Swim-Pond-Rain-Russians-Writing/dp/1984856022 • The Master and His Emissary: The Divided Brain and the Making of the Western World: https://www.amazon.com/Master-His-Emissary-Divided-Western/dp/0300245920/ — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com. Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

    1h 35m
  8. Rapidly test and validate any startup idea with the 2-day Foundation Sprint (from the creators of the Design Sprint) | Jake Knapp & John Zeratsky (Character Capital)

    JUL 13

    Rapidly test and validate any startup idea with the 2-day Foundation Sprint (from the creators of the Design Sprint) | Jake Knapp & John Zeratsky (Character Capital)

    Jake Knapp and John Zeratsky are the co-creators of the Design Sprint (the famous five-day product innovation process) and authors of the bestselling book Sprint. After decades of working with over 300 startups in the earliest stages, they discovered that most startups fail not because they can’t build, but because they build the wrong thing. The very beginning of a startup is your highest-leverage moment, and most teams waste months or years by skipping a few critical early questions. Jake and John developed the Foundation Sprint to help startups validate ideas and compress months of work into just two days. What you’ll learn: 1. The step-by-step Foundation Sprint process that compresses three or four months of validation into two days—including templates you can use immediately 2. Why differentiation is the #1 predictor of startup success (with the 2x2 framework that you can use with your team) 3. The three fundamental questions every founder should answer before writing a line of code 4. The “note and vote” technique that eliminates groupthink and gets honest answers from your colleagues 5. The seven “magic lenses” for choosing between multiple product ideas 6. The biggest mistake engineers make when building with AI tools 7. The paradox of speed: why “building nothing first” can get you to product-market fit faster — Brought to you by: Brex—The banking solution for startups: https://www.brex.com/product/business-account?ref_code=bmk_dp_brand1H25_ln_new_fs Paragon—Ship every SaaS integration your customers want: https://www.useparagon.com/lenny Coda—The all-in-one collaborative workspace: https://coda.io/lenny — Transcript: https://www.lennysnewsletter.com/p/the-foundation-sprint-jake-knapp-and-john-zeratsky — My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/167485876/my-biggest-takeaways-from-this-conversation — Where to find Jake Knapp: • X: https://twitter.com/jakek • LinkedIn: https://www.linkedin.com/in/jake-knapp/ • Website: https://jakeknapp.com/ — Where to find John Zeratsky: • X: https://twitter.com/jazer • LinkedIn: https://www.linkedin.com/in/johnzeratsky/ • Website: https://johnzeratsky.com/ — In this episode, we cover: (00:00) Introduction to Jake Knapp and John Zeratsky (04:41) Origins of the Design Sprint (11:06) The Foundation Sprint process (14:40) Phase one: The basics (16:57) Case study: Latchet (28:50) Phase two: Differentiation (36:24) The importance of differentiation (40:15) Thoughts on price differentiation (43:37) Case study: Mellow (46:04) Custom differentiators (49:30) The mini manifesto (52:02) Phase three: Approach to the project (54:50) Magic lenses activity (01:02:39) Prototyping and testing (01:10:00) Real-world examples and success stories (01:15:15) Motivation behind The Foundation Sprint (01:17:15) The outcome of the sprint: The founding hypothesis (01:19:28) The Design Sprint (01:28:19) The role of AI in prototyping (01:36:50) Final thoughts and resources — Referenced: • Introducing the Foundation Sprint: From the creators of the Design Sprint: https://www.lennysnewsletter.com/p/introducing-the-foundation-sprint • Making time for what matters | Jake Knapp and John Zeratsky (authors of Sprint and Make Time, co-founders of Character Capital): https://www.lennysnewsletter.com/p/making-time-for-what-matters-jake • Eli Blee-Goldman on LinkedIn: https://www.linkedin.com/in/eli-blee-goldman/ • Character Capital: https://www.character.vc/ • Character Labs: https://www.character.vc/labs • Etsy: https://www.etsy.com/ • Shopify: https://www.shopify.com/ • Naming expert shares the process behind creating billion-dollar brand names like Azure, Vercel, Windsurf, Sonos, Blackberry, and Impossible Burger | David Placek (Lexicon Branding): https://www.lennysnewsletter.com/p/naming-expert-david-placek • Sonos: https://www.sonos.com/ • Vercel: https://vercel.com/ • Windsurf: https://windsurf.com/ • April Dunford on product positioning, segmentation, and optimizing your sales process: https://www.lennysnewsletter.com/p/april-dunford-on-product-positioning • Positioning: https://www.lennysnewsletter.com/p/positioning • 10 things we know to be true: https://about.google/company-info/philosophy/ • Gandalf: https://en.wikipedia.org/wiki/Gandalf • Frodo: https://en.wikipedia.org/wiki/Frodo_Baggins • Mordor: https://en.wikipedia.org/wiki/Mordor • 35 years of product design wisdom from Apple, Disney, Pinterest, and beyond | Bob Baxley: https://www.lennysnewsletter.com/p/35-years-of-product-design-wisdom-bob-baxley • The Primal Mark: How the Beginning Shapes the End in the Development of Creative Ideas: https://www.gsb.stanford.edu/faculty-research/publications/primal-mark-how-beginning-shapes-end-development-creative-ideas • Base44: https://base44.com/ • Solo founder, $80M exit, 6 months: The Base44 bootstrapped startup success story | Maor Shlomo: https://www.lennysnewsletter.com/p/the-base44-bootstrapped-startup-success-story-maor-shlomo • Google Meet: https://meet.google.com/ • Blue Bottle Coffee: https://bluebottlecoffee.com • Reclaim: https://reclaim.ai/ • The official Foundation Sprint + Design Sprint template: https://www.character.vc/miro-template • Rippling: https://www.rippling.com/ • Latchet: https://latchet.com/ • Mellow: http://getmellow.com/ • AxionOrbital: https://axionorbital.space/ — Recommended books: • Sprint: How to Solve Big Problems and Test New Ideas in Just Five Days: https://www.amazon.com/Sprint-audiobook/dp/B019R2DQIY • Make Time: How to Focus on What Matters Every Day: https://www.amazon.com/Make-Time-Focus-Matters-Every/dp/0525572422 • Click: How to Make What People Want: https://www.amazon.com/Click-Make-What-People-Want/dp/1668072114 Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com. — Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

    1h 42m
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