Lenny's Podcast: Product | Growth | Career

• 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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• Solo founder, $80M exit, 6 months: The Base44 bootstrapped startup success story | Maor Shlomo

  Maor Shlomo is the founder of Base44, an AI-powered app builder that he bootstrapped to an over $80 million acquisition by Wix in just six months. As a solo founder (with severe ADHD), he hit $1 million ARR just three weeks after launch and grew the product to more than 400,000 users, all while navigating two wars in Israel and never raising a dollar of outside funding.What you’ll learn:1. The growth playbook that took Base44 from three friends to 400,000 users without spending any money on marketing2. How he hasn’t written a single line of front-end code in three months—and how to structure your code repository to make it easier for AI to write your code3. His AI productivity stack that allowed him to compete against heavily funded competitors4. Why being a solo founder in AI might be the ultimate advantage (and the wedding story that almost killed the business)5. The story of signing the $80M acquisition deal while war broke out with Iran6. How to identify when to sell vs. stay independent (and why Maor chose acquisition despite being highly profitable)7. The counterintuitive product decision that tripled activation by removing a “helpful” feature8. How building in public on LinkedIn drove more growth than any paid channel—Brought to you by:Sauce—Turn customer pain into product revenue: https://sauce.app/lennyDscout—The UX platform to capture insights at every stage: from ideation to production: https://www.dscout.com/Contentsquare—Create better digital experiences: https://contentsquare.com/lenny/—Transcript: https://www.lennysnewsletter.com/p/the-base44-bootstrapped-startup-success-story-maor-shlomo—My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/167384119/my-biggest-takeaways-from-this-conversation—Where to find Maor Shlomo:• X: https://x.com/ms_base44• LinkedIn: https://www.linkedin.com/in/maor-shlomo-1088b4144/—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 Maor and Base44(08:16) The origin story: how Base44 came to be(14:55) Bootstrapping and solo founding: challenges and insights(22:52) Productivity hacks and tech stack for solo founders(27:23) How to get started using Base44(28:47) Thoughts on raising money(34:05) Distribution in the age of AI(36:09) Ambition and goals(40:05) Growth strategies: from first users to thousands(51:32) Building in public(57:42) The solo founder journey(01:00:23) Community support(01:03:23) Hackathons and partnerships(01:06:42) The importance of velocity in product development(01:08:20) Technical stack and infrastructure insights(01:15:24) Activation lessons(01:18:19) The acquisition journey with Wix(01:25:14) Final thoughts and advice for founders—Referenced:• Base44: https://base44.com/• Retool: https://retool.com/• Tzofim: https://www.israelscouts.org/• Y Combinator: https://www.ycombinator.com/• RescueTime: https://www.rescuetime.com/• Cursor: https://www.cursor.com/• Wix: https://www.wix.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• Building Lovable: $10M ARR in 60 days with 15 people | Anton Osika (CEO and co-founder): https://www.lennysnewsletter.com/p/building-lovable-anton-osika• Inside Bolt: From near-death to ~$40m ARR in 5 months—one of the fastest-growing products in history | Eric Simons (founder and CEO of StackBlitz): https://www.lennysnewsletter.com/p/inside-bolt-eric-simons• Behind the product: Replit | Amjad Masad (co-founder and CEO): https://www.lennysnewsletter.com/p/behind-the-product-replit-amjad-masad• Everyone’s an engineer now: Inside v0’s mission to create a hundred million builders | Guillermo Rauch (founder and CEO of Vercel, creators of v0 and Next.js): https://www.lennysnewsletter.com/p/everyones-an-engineer-now-guillermo-rauch• Snowflake: https://www.snowflake.com• Yoav Orlev on LinkedIn: https://www.linkedin.com/in/yoav-orlev-4a044b72• WhatsApp: https://www.whatsapp.com/• Amazon: https://www.amazon.com/• Google: https://about.google/• MongoDB: https://www.mongodb.com/• Deloitte: https://www.deloitte.com/• Render: Render.com• Claude 4: https://www.anthropic.com/news/claude-4• Gemini: https://gemini.google.com/app• Cloudflare: https://www.cloudflare.com/—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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• I’ve run 75+ businesses. Here’s why you’re probably chasing the wrong idea. | Andrew Wilkinson (co‑founder of Tiny)

  Andrew Wilkinson is the co‑founder of Tiny, a holding company that quietly owns more than three dozen profitable internet and consumer brands, including Dribbble and the AeroPress coffee maker. Starting as a teenage barista and web designer, he’s created a portfolio approaching $300 million in yearly sales (and he was personally worth over $1 billion at one point)—all without ever raising venture capital.In this conversation, you’ll learn:1. The “fish where the fish are” framework for spotting high‑margin niches no one else notices2. The exact agent stack (Lindy, Replit, Limitless, and more) that supercharges Andrew’s day-to-day productivity (and has replaced his assistant)3. How Andrew evaluates companies in less than 15 minutes using Buffett‑style moats and “lazy leadership”4. Telltale signs you should shut down (or never start) that startup idea5. His journey from crippling anxiety to clarity through SSRIs and ADHD medication6. His prediction that most knowledge work will be automated—and the skills to teach your kids now—Brought to you by:Sauce—Turn customer pain into product revenueEnterpret—Transform customer feedback into product growthMiro—A collaborative visual platform where your best work comes to life—Where to find Andrew Wilkinson:• X: https://x.com/awilkinson• LinkedIn: https://www.linkedin.com/in/awilkinson/—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 Andrew Wilkinson(04:07) Finding the right business idea(07:18) Avoiding common business pitfalls(11:58) Finding your unfair advantage(17:08) Fish where the fish are(20:08) Why boring is good(25:30) Bootstrapping vs. venture capital(31:20) Lessons from acquiring and managing businesses(36:47) Avoiding people problems(42:39) Leveraging AI in business and life(49:30) The Limitless device(53:13) Job displacement and AI’s future impact(58:20) Advice for new grads(01:02:50) Parenting in the age of AI(01:05:26) The pursuit of happiness beyond wealth(01:10:10) Mental health and medication(01:16:45) Lightning round and final thoughts—Referenced:• Andrew’s post on X with the Charlie Munger quote: https://x.com/awilkinson/status/1265653805443506182• Metalab: https://www.metalab.com/• Letterboxd: https://letterboxd.com/• AeroPress: https://aeropress.com/• Brian Armstrong on X: https://x.com/brian_armstrong• Warren Buffett’s quote: https://quotefancy.com/quote/931119/Warren-Buffett-I-am-a-better-investor-because-I-am-a-businessman-and-a-better-businessman• Flow: https://www.getflow.com/• Instacart: https://www.instacart.com/• Things: https://culturedcode.com/things/• Dustin Moskovitz on LinkedIn: https://www.linkedin.com/in/dmoskov/• Salesforce: https://www.salesforce.com/• Serato: https://serato.com/• Chris Sparling on X: https://x.com/_sparling_• Lindy: https://www.lindy.ai/• Replit: https://replit.com/• Behind the product: Replit | Amjad Masad (co-founder and CEO): https://www.lennysnewsletter.com/p/behind-the-product-replit-amjad-masad• David Ogilvy: https://en.wikipedia.org/wiki/David_Ogilvy_(businessman)• Malcolm Gladwell’s website: https://www.gladwellbooks.com/• Inside Bolt: From near-death to ~$40m ARR in 5 months—one of the fastest-growing products in history | Eric Simons (founder and CEO of StackBlitz): https://www.lennysnewsletter.com/p/inside-bolt-eric-simons• Building Lovable: $10M ARR in 60 days with 15 people | Anton Osika (CEO and co-founder): https://www.lennysnewsletter.com/p/building-lovable-anton-osika• Limitless: https://www.limitless.ai/• Perplexity: https://www.perplexity.ai/• Claude: https://claude.ai/• ChatGPT: https://chatgpt.com/• Gemini: https://gemini.google.com/app• William Gibson’s quote: https://www.goodreads.com/quotes/681-the-future-is-already-here-it-s-just-not-evenly• Palm Treo: https://en.wikipedia.org/wiki/Palm_Treo• Sam Altman on X: https://x.com/sama• Dario Amodei on X: https://x.com/darioamodei• Anthropic’s CPO on what comes next | Mike Krieger (co-founder of Instagram): https://www.lennysnewsletter.com/p/anthropics-cpo-heres-what-comes-next• Challengers on AppleTV+: https://tv.apple.com/us/movie/challengers/umc.cmc.53cuz33n4e74ixj8whccj87oc• Matic vacuum: https://maticrobots.com/• Jerzy Gregorek’s quote: https://www.goodreads.com/quotes/8652595-hard-choices-easy-life-easy-choices-hard-life• Tiny: https://www.tiny.com/• Dribbble: https://dribbble.com/—Recommended books:• The Laws of Human Nature: https://www.amazon.com/Laws-Human-Nature-Robert-Greene/dp/0525428143• How to Get Rich: One of the World’s Greatest Entrepreneurs Shares His Secrets: https://www.amazon.com/How-Get-Rich-Greatest-Entrepreneurs/dp/1591842719—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].—Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

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