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

Nick Turley is Head of ChatGPT, the fastest-growing product in history, with 700 million weekly active users (10% of the world’s population). He was part of the original hackathon team that shipped ChatGPT in just 10 days, helped it grow from zero to billions in revenue, and leads product for what may be the most consequential product of our time. We recorded this the day before GPT-5 launched. *We discuss:* 1. The 10-day sprint from deciding to ship ChatGPT to Sam Altman’s tweet (and why it was originally called “Chat with GPT-3.5”) 2. How they ran a willingness-to-pay Van Westendorp survey in their Discord to decide on the $20/month price point that everyone copied 3. The “Is it maximally accelerated?” philosophy that drives OpenAI’s insane shipping velocity 4. Why ChatGPT’s retention curve “smiles”—users leave, then come back months later using it more 5. The accidental decisions that changed history, including not having a waitlist 6. The impact ChatGPT will have on SEO and product growth 7. The counterintuitive reason why shipping unpolished AI features beats waiting for perfection 8. Why ChatGPT intentionally shipped with that “ugly” model-chooser dropdown 9. How TikTok comments became a primary user research channel early on *Brought to you by:* Orkes—The enterprise platform for reliable applications and agentic workflows: https://www.orkes.io/ Vanta—Automate compliance. Simplify security: https://vanta.com/lenny PostHog—How developers build successful products: https://posthog.com/lenny *Transcript:* https://www.lennysnewsletter.com/p/inside-chatgpt-nick-turley *My biggest takeaways (for paid newsletter subscribers):* https://www.lennysnewsletter.com/i/170411252/my-biggest-takeaways-from-this-conversation *Where to find Nick Turley* • X: https://x.com/nickaturley • LinkedIn: https://www.linkedin.com/in/nicholasturley/ • Website: https://nickturley.com/ *Where to find Lenny:* • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ *In this episode, we cover:* (00:00) Introduction to Nick Turley (04:52) GPT-5 launch (09:13) The vision for ChatGPT and AI assistants (13:52) The early days of ChatGPT (17:14) The success and impact of ChatGPT (20:44) Product development and iteration (23:11) Maximally accelerated: the OpenAI approach (26:17) Retention and user engagement (33:42) The future of chat interfaces (36:31) The evolution of ChatGPT (38:52) Subscription model and pricing strategies (42:10) Enterprise adoption and challenges (44:10) Balancing multiple product lines (52:13) Emergent use cases and user feedback (01:02:15) OpenAI’s unique product development approach (01:05:07) The importance of team composition (01:08:50) Balancing speed and quality in AI development (01:14:23) The role of evals in product development (01:16:13) The future of AI-driven content and GPTs (01:21:51) Philosophy and product leadership (01:23:47) Career journey and advice (01:27:49) Lightning round and final thoughts *Referenced:* • GPT-5 and the new era of work: https://openai.com/index/gpt-5-new-era-of-work/ • Instacart: https://www.instacart.com/ • OpenAI’s CPO on how AI changes must-have skills, moats, coding, startup playbooks, more | Kevin Weil (CPO at OpenAI, ex-Instagram, Twitter): https://www.lennysnewsletter.com/p/kevin-weil-open-ai • Sam Altman on X: https://x.com/sama • Figma: https://www.figma.com/ • Van Westendorp’s Price Sensitivity Meter: https://en.wikipedia.org/wiki/Van_Westendorp%27s_Price_Sensitivity_Meter • Rahul Vohra on LinkedIn: https://www.linkedin.com/in/rahulvohra/ • Superhuman’s secret to success: Ignoring most customer feedback, manually onboarding every new user, obsessing over every detail, and positioning around a single attribute: speed | Rahul Vohra (CEO): https://www.lennysnewsletter.com/p/superhumans-secret-to-success-rahul-vohra • Dropbox: http://dropbox.com/ • Airtable: https://www.airtable.com/ • Notion: https://www.notion.com/ • Instant Pot: https://instantpot.com/ • MS-DOS: https://en.wikipedia.org/wiki/MS-DOS • Expanding on what we missed with sycophancy: https://openai.com/index/expanding-on-sycophancy/ • What we’re optimizing ChatGPT for: https://openai.com/index/how-we're-optimizing-chatgpt/ • Charlie Munger’s quote: https://www.goodreads.com/quotes/11903426-show-me-the-incentive-and-i-ll-show-you-the-outcome • Anthropic’s CPO on what comes next | Mike Krieger (co-founder of Instagram): https://www.lennysnewsletter.com/p/anthropics-cpo-heres-what-comes-next • Beyond vibe checks: A PM’s complete guide to evals: https://www.lennysnewsletter.com/p/beyond-vibe-checks-a-pms-complete ...References continued at: https://www.lennysnewsletter.com/p/inside-chatgpt-nick-turley _Production and marketing by https://penname.co/._ _For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com._ Lenny may be an investor in the companies discussed.

Bret Taylor’s legendary career includes being CTO of Meta, co-CEO of Salesforce, chairman of the board at OpenAI (yes, during that drama), co-creating both Google Maps and the Like button, and founding three companies. Today he’s the founder and CEO of Sierra, an AI agent company transforming customer service. He’s one of the few people I’ve met who’s been wildly successful at every level—from engineer to C-suite executive to founder—and across almost every discipline, including PM, engineer, CTO, COO, CPO, CEO, and board member. *In this conversation, you’ll learn:* 1. The brutal product review that nearly ended his Google career—and how that failure led to creating Google Maps 2. The question Sheryl Sandberg taught him to ask every morning (“What’s the most impactful thing I can do today?”) that transformed how he approached every role 3. The three AI market segments that matter 4. Why AI agents will replace SaaS products 5. His framework for knowing whose advice to actually listen to—and how that came in handy during the OpenAI board drama 6. The counterintuitive go-to-market strategy most AI startups get wrong 7. Sierra’s outcome-based pricing model that’s transforming how enterprise software is sold (and why every SaaS company should adopt it) 8. What he’s teaching his kids about AI that every parent should know *Brought to you by:* CodeRabbit—Cut code review time and bugs in half. Instantly: https://coderabbit.link/lenny Basecamp—The famously straightforward project management system from 37signals: https://www.basecamp.com/lenny Vanta—Automate compliance. Simplify security: https://vanta.com/lenny *Transcript:* https://www.lennysnewsletter.com/p/he-saved-openai-bret-taylor *My biggest takeaways (for paid newsletter subscribers):* https://www.lennysnewsletter.com/i/168905359/my-biggest-takeaways-from-this-conversation *Where to find Bret Taylor:* • X: https://x.com/btaylor • LinkedIn: https://www.linkedin.com/in/brettaylor/ *Where to find Lenny:* • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ *In this episode, we cover:* (00:00) Introduction to Bret Taylor (04:10) Bret’s early career and first major mistake (08:24) The birth of Google Maps (11:57) Lessons from FriendFeed and the importance of honest feedback (31:30) The future of coding and AI’s role (45:26) Preparing the next generation for an AI-driven world (48:46) AI in education (52:05) Business strategies in the AI market (01:04:38) Outcome-based pricing in AI (01:09:15) Productivity gains and AI (01:17:35) Go-to-market strategies for AI products (01:21:49) Lightning round and final thoughts *Referenced:* • Marissa Mayer on LinkedIn: https://www.linkedin.com/in/marissamayer/ • “Lazy Sunday”—SNL: https://www.youtube.com/watch?v=sRhTeaa_B98 • Quip: https://quip.com/ • Sierra: https://sierra.ai/ • FriendFeed: https://en.wikipedia.org/wiki/FriendFeed • Sheryl Sandberg on LinkedIn: https://www.linkedin.com/in/sheryl-sandberg-5126652/ • Jim Norris on LinkedIn: https://www.linkedin.com/in/halfspin/ • Paul Buchheit on X: https://x.com/paultoo • Sanjeev Singh on LinkedIn: https://www.linkedin.com/in/sanjeev-singh-20a1b72/ • Barack Obama: https://www.obamalibrary.gov/obamas/president-barack-obama • Oprah Winfrey: https://en.wikipedia.org/wiki/Oprah_Winfrey • Ashton Kutcher: https://en.wikipedia.org/wiki/Ashton_Kutcher • PayPal Mafia: https://en.wikipedia.org/wiki/PayPal_Mafia • Sam Altman on X: https://x.com/sama • Warren Buffett on X: https://x.com/warrenbuffett • Unix: https://en.wikipedia.org/wiki/Unix • Fortran: https://en.wikipedia.org/wiki/Fortran • C: https://en.wikipedia.org/wiki/C_(programming_language) • Python: https://www.python.org/ • Perl: https://www.perl.org/ • Rust: https://www.rust-lang.org/ • Eleven Labs: https://elevenlabs.io/ • The exact AI playbook (using MCPs, custom GPTs, Granola) that saved ElevenLabs $100k+ and helps them ship daily | Luke Harries (Head of Growth): https://www.lennysnewsletter.com/p/the-ai-marketing-stack • Confluent: https://www.confluent.io/ • Databricks: https://www.databricks.com/ • Snowflake: https://www.snowflake.com • Harvey: https://www.harvey.ai/ • Behind the founder: Marc Benioff: https://www.lennysnewsletter.com/p/behind-the-founder-marc-benioff • Larry Summers’s website: https://larrysummers.com/ • AutoCAD: https://www.autodesk.com/products/autocad/overview • Revit: https://www.autodesk.com/products/revit/ ...References continued at: https://www.lennysnewsletter.com/p/he-saved-openai-bret-taylor _Production and marketing by https://penname.co/._ _For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com._ Lenny may be an investor in the companies discussed.

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

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

Dan Shipper is the co-founder and CEO of Every. With just 15 people, Every publishes a daily AI newsletter, ships multiple AI products, and operates a million-dollar-a-year consulting arm—all while their engineers write virtually zero code. It’s the most radical example of AI-first operations, and Dan is a prolific writer who has become a leading voice on how AI is transforming the way we build and work. *Learn:* 1. Why Dan thinks AI won’t steal jobs en masse—and may actually reshore many jobs to the U.S. 2. The most underrated AI tool for non-programmers 3. An inside look at Every’s AI-first workflow 4. Why every company needs an “AI operations lead” 5. How Dan’s team uses an arsenal of AI agents (Claude, Codex, “Friday,” “Charlie”) in parallel, treating each AI like a specialist with unique strengths 6. Why generalists will thrive in an AI-first world, as rigid job titles blur and everyone becomes a “manager” of AI tools 7. Dan’s playbook for making any company AI-first—from the CEO setting the example, to hosting internal prompt-sharing sessions, to upskilling teams on AI tools *Brought to you by:* CodeRabbit—Cut code review time and bugs in half. Instantly: https://coderabbit.link/lenny DX—A platform for measuring and improving developer productivity: https://getdx.com/lenny PostHog—How developers build successful products: https://posthog.com/lenny *Transcript:* https://www.lennysnewsletter.com/p/inside-every-dan-shipper *My biggest takeaways (for paid newsletter subscribers):* https://www.lennysnewsletter.com/i/167681269/my-biggest-takeaways-from-this-conversation *Where to find Dan Shipper:* • X: https://x.com/danshipper • LinkedIn: https://www.linkedin.com/in/danshipper/ • Podcast: https://every.to/podcast *Where to find Lenny:* • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ *In this episode, we cover:* (00:00) Welcome and introduction (04:04) Hot takes on AI and job reshoring (07:06) The power of Claude Code for non-coders (14:35) The future of AI in business operations (18:45) AI’s role in enhancing human skills (22:26) The evolution of AI tools and their applications (25:40) Building an AI-first company (29:50) Innovative AI operations and team dynamics (35:35) Dan's AI stack (41:26) Compounding engineering (48:29) The impact of AI on learning and development (50:10) Accelerating career growth with AI (51:36) Revolutionizing code review and workflow (53:07) The importance of coding knowledge (57:26) Building AI-driven products (01:02:01) Innovative fundraising strategies (01:08:45) Consulting and AI adoption in companies (01:17:01) The allocation economy and future skills (01:20:12) The value of generalists in the AI age (01:24:07) Lightning round and final thoughts *Referenced:* • Claude Code: https://www.anthropic.com/claude-code • Gemini CLI: https://blog.google/technology/developers/introducing-gemini-cli-open-source-ai-agent/ • Microsoft Copilot: https://copilot.microsoft.com/ • Cursor: https://www.cursor.com/ • Base44: https://base44.com/ • Solo founder, $80M exit, 6 months: The Base44 bootstrapped startup success story | Maor Shlomo: https://www.lennysnewsletter.com/p/the-base44-bootstrapped-startup-success-story-maor-shlomo • The rise of Cursor: The $300M ARR AI tool that engineers can’t stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell • Plato’s Argument Against Writing: https://fs.blog/an-old-argument-against-writing/ • From ChatGPT to Instagram to Uber: The quiet architect behind the world’s most popular products | Peter Deng: https://www.lennysnewsletter.com/p/the-quiet-architect-peter-deng • Granola: https://www.granola.ai/ • Tobi Lutke’s post on X about context engineering: https://x.com/tobi/status/1935533422589399127 • Tobi Lütke’s leadership playbook: Playing infinite games, operating from first principles, and maximizing human potential (founder and CEO of Shopify): https://www.lennysnewsletter.com/p/tobi-lutkes-leadership-playbook • Every: https://every.to/ • Cora: https://www.cora.computer/ • Sparkle: https://makeitsparkle.co/ • Spiral: https://spiral.computer/ • Lex: https://lex.page/ • Nathan Baschez on LinkedIn: https://www.linkedin.com/in/nbashaw/ • Kate Lee on LinkedIn: https://www.linkedin.com/in/kate-lee-506768/ • Katie Parrott on LinkedIn: https://www.linkedin.com/in/katieparrott/ • Animalz: https://www.animalz.co/ • Rachel Woods on X: https://x.com/rachel_l_woods • Nityesh Agarwal on LinkedIn: https://www.linkedin.com/in/nityeshaga • Claude Opus 4: https://www.anthropic.com/claude/opus *...References continued at:* https://www.lennysnewsletter.com/p/inside-every-dan-shipper _Production and marketing by https://penname.co/._ _For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com._ Lenny may be an investor in the companies discussed.

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

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