Lenny's Podcast: Product | Career | Growth

• 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 Maps2. 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 role3. The three AI market segments that matter4. Why AI agents will replace SaaS products5. His framework for knowing whose advice to actually listen to—and how that came in handy during the OpenAI board drama6. The counterintuitive go-to-market strategy most AI startups get wrong7. 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/lennyBasecamp—The famously straightforward project management system from 37signals: https://www.basecamp.com/lennyVanta—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 [email protected] may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

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• 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 model2. Why AI companies can capture 25% to 50% of value created, vs. 10% to 20% for traditional SaaS products3. Why popular AI coding tools may have already doomed themselves with underpricing4. The “give-and-get” framework top negotiators use to extract maximum value from every deal5. The negotiation strategy that helped one founder 4x their deal size overnight6. 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/lennyDX—A platform for measuring and improving developer productivity: https://getdx.com/lennyPersona—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: [email protected] — 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 [email protected] may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

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• 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 Anthropic2. How Meta’s $100M offers reveal the true market price of top AI talent3. Why AI progress is still accelerating (not plateauing), and how most people misjudge the exponential4. Ben’s “economic Turing test” for knowing when we’ve achieved AGI—and why it’s likely coming by 2027-20285. Why he believes 20% unemployment is inevitable6. The AI nightmare scenarios that concern him most—and how he believes we can still avoid them7. How focusing on AI safety created Claude’s beloved personality8. 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/lennyLucidLink—Real-time cloud storage for teams: https://www.lucidlink.com/lennyFin—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 [email protected] may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

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• 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-programmers3. An inside look at Every’s AI-first workflow4. 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 strengths6. Why generalists will thrive in an AI-first world, as rigid job titles blur and everyone becomes a “manager” of AI tools7. 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/lennyDX—A platform for measuring and improving developer productivity: https://getdx.com/lennyPostHog—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 [email protected] may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

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• 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 immediately2. 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 code4. The “note and vote” technique that eliminates groupthink and gets honest answers from your colleagues5. The seven “magic lenses” for choosing between multiple product ideas6. The biggest mistake engineers make when building with AI tools7. 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_fsParagon—Ship every SaaS integration your customers want: https://www.useparagon.com/lennyCoda—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/1668072114Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].—Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

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