Lenny's Podcast: Product | Growth | Career Podcast By Lenny Rachitsky cover art

Lenny's Podcast: Product | Growth | Career

Lenny's Podcast: Product | Growth | Career

By: Lenny Rachitsky
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 Interviews with world-class product leaders and growth experts to uncover concrete, actionable, and tactical advice to help you build, launch, and grow your own product.Lenny Rachitsky Economics Leadership Management & Leadership
Episodes
  • I’ve run 75+ businesses. Here’s why you’re probably chasing the wrong idea. | Andrew Wilkinson (co‑founder of Tiny)

    I’ve run 75+ businesses. Here’s why you’re probably chasing the wrong idea. | Andrew Wilkinson (co‑founder of Tiny)
    Jul 3 2025
    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, ...
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    1 hr and 28 mins
  • Naming expert shares the process behind creating billion-dollar brand names like Azure, Vercel, Windsurf, Sonos, Blackberry, and Impossible Burger | David Placek (Lexicon Branding)

    Naming expert shares the process behind creating billion-dollar brand names like Azure, Vercel, Windsurf, Sonos, Blackberry, and Impossible Burger | David Placek (Lexicon Branding)
    Jun 29 2025
    David Placek is the founder of Lexicon Branding, a company that focuses exclusively on the development of brand names for competitive advantage. Lexicon is behind iconic names such as Sonos, Microsoft’s Azure, Windsurf, Vercel, Impossible Foods, BlackBerry, Intel’s Pentium, Apple’s PowerBook, and Swiffer. Over 40 years, David’s team has named nearly 4,000 brands and companies, employing over 250 linguists and pioneering naming innovation.What you’ll learn:1. The three-step process that generated names like Windsurf and Vercel2. How a name can give you the edge that no marketing budget can buy3. Why you won’t “know it when you see it”4. Why Microsoft called Azure “a dumb name” before it became their billion-dollar cloud platform5. Why polarizing opinions are the strongest signal that you’ve found the right name6. How every letter of the alphabet creates a specific psychological vibration7. The diamond framework: a 4-step process any founder can use to find their perfect name8. Why domain names don’t matter anymore in the age of AI—Brought to you by:WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUsStripe—Helping companies of all sizes grow revenueOneSchema—Import CSV data 10x faster—Where to find David Placek:• LinkedIn: https://www.linkedin.com/in/david-placek-05a82/• Website: https://www.lexiconbranding.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 David and Lexicon Branding(04:44) The story of Sonos(09:27) The psychology of naming(11:33) The initial resistance to Microsoft's Azure(14:35) The importance of a great brand name(18:11) The three steps of naming: create, invent, implement(28:23) Qualities of great brand name creators(31:24) How long the naming process takes(32:12) The Windsurf case study(36:10) Naming in the AI era(39:37) When to change your name(43:10) The role of linguists(45:54) The power of letters in branding(48:15) The Vercel case study(50:12) The implementation phase(52:52) Client management and market success(55:16) The diamond exercise(01:04:23) Suspending judgment(01:07:31) Polarization and boldness(01:11:01) Domain names(01:12:48) Final thoughts and lightning round—Referenced:• PowerBook: https://en.wikipedia.org/wiki/PowerBook• Pentium: https://en.wikipedia.org/wiki/Pentium• BlackBerry: https://en.wikipedia.org/wiki/BlackBerry• Swiffer: https://www.swiffer.com/• Impossible Burger: https://impossiblefoods.com/• Vercel: https://vercel.com/• Windsurf: https://windsurf.com/• CapCut: https://www.capcut.com/• Azure: https://azure.microsoft.com/• Sonos: https://www.sonos.com/• John MacFarlane on LinkedIn: https://www.linkedin.com/in/john-macfarlane-08a8aa20/• Harry Potter: https://en.wikipedia.org/wiki/Harry_Potter_(film_series)• The Call of the Wild: https://en.wikipedia.org/wiki/The_Call_of_the_Wild• 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• Sound symbolism: https://en.wikipedia.org/wiki/Sound_symbolism• Anduril: https://www.anduril.com/• Anthropic: https://www.anthropic.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• 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 a magical AI code editor used by over 1 million developers in four months: The untold story of Windsurf | Varun Mohan (co-founder and CEO): https://www.lennysnewsletter.com/p/the-untold-story-of-windsurf-varun-mohan• Y Combinator: https://www.ycombinator.com/• Chevrolet Corvette: https://en.wikipedia.org/wiki/Chevrolet_Corvette• Viagra: https://www.viagra.com/• In vino veritas: https://en.wikipedia.org/wiki/In_vino_veritas• Infoseek: https://en.wikipedia.org/wiki/Infoseek• Andy Grove: https://en.wikipedia.org/wiki/Andrew_Grove• Churchill at War on Netflix: https://www.netflix.com/title/81609374• Yellowstone on Prime Video: https://www.amazon.com/Yellowstone-Season-1/dp/B07D7FBB8Z• 1883 on Prime Video: https://www.amazon.com/1883-Season-1/dp/B0B8JTS8QW• 1923 on Paramount+: https://www.paramountplus.com/shows/1923/• Taylor Sheridan on X: https://x.com/taylorSheridan• Hardy fly rods: https://www.hardyfishing.com/collections/fly-rods• T.E. Lawrence quote: https://www.goodreads.com/quotes/11340-all-men-dream-but-not-equally-those-who-dream-by• Lawrence of Arabia: https://www.imdb.com/title/tt0056172/• DreamWorks: https://...
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    1 hr and 23 mins
  • From ChatGPT to Instagram to Uber: The quiet architect behind the world’s most popular products | Peter Deng

    From ChatGPT to Instagram to Uber: The quiet architect behind the world’s most popular products | Peter Deng
    Jun 22 2025
    Peter Deng has led product teams at OpenAI, Instagram, Uber, Facebook, Airtable, and Oculus and helped build products used by billions—including Facebook’s News Feed, the standalone Messenger app, Instagram filters, Uber Reserve, ChatGPT, and more. Currently he’s investing in early-stage founders at Felicis. In this episode, Peter dives into his most valuable lessons from building and scaling some of tech’s most iconic products and companies.What you’ll learn:1. Peter’s one‑sentence test for hiring superstars2. Why your product (probably) doesn’t matter3. Why you don’t need a tech breakthrough to build a huge business4. The five PM archetypes, and how to build a team of Avengers5. Counterintuitive lessons on growing products from 0 to 1, and 1 to 1006. The importance of data flywheels and workflows—Brought to you by:Paragon—Ship every SaaS integration your customers wantPragmatic Institute—Industry‑recognized product, marketing, and AI training and certificationsContentsquare—Create better digital experiences—Where to find Peter Deng:• X: https://x.com/pxd• LinkedIn: https://www.linkedin.com/in/peterxdeng/—In this episode, we cover:(00:00) Introduction to Peter Deng(05:41) AI and AGI insights(11:35) The future of education with AI(16:53) The power of language in leadership(21:01) Building iconic products(36:44) Scaling from zero to 100(41:56) Balancing short- and long-term goals(47:12) Creating a healthy tension in teams(50:02) The five archetypes of product managers(55:39) Primary and secondary archetypes(58:47) Hiring for growth mindset and autonomy(01:15:52) Effective management and communication strategies(01:19:23) Presentation advice and self-advocacy(01:25:50) Balancing craft and practicality in product management(01:30:40) The importance of empathy in design thinking(01:35:45) Career decisions and learning opportunities(01:42:05) Lessons from product failures(01:45:42) Lightning round and final thoughts—Referenced:• OpenAI: https://openai.com/• Artificial general intelligence (AGI): https://en.wikipedia.org/wiki/Artificial_general_intelligence• Head of ChatGPT answers philosophical questions about AI at SXSW 2024 with SignalFire’s Josh Constine: https://www.youtube.com/watch?v=mgbgI0R6XCw• Professors Are Using A.I., Too. Now What?: https://www.npr.org/2025/05/21/1252663599/kashmir-hill-ai#:~:text=Now%20What• Herbert H. Clark: https://web.stanford.edu/~clark/• Russian speakers get the blues: https://www.newscientist.com/article/dn11759-russian-speakers-get-the-blues/• Ilya Sutskever (OpenAI Chief Scientist)—Building AGI, Alignment, Future Models, Spies, Microsoft, Taiwan, & Enlightenment: https://www.dwarkesh.com/p/ilya-sutskever• Anthropic’s CPO on what comes next | Mike Krieger (co-founder of Instagram): https://www.lennysnewsletter.com/p/anthropics-cpo-heres-what-comes-next• Kevin Systrom on LinkedIn: https://www.linkedin.com/in/kevinsystrom/• Building a magical AI code editor used by over 1 million developers in four months: The untold story of Windsurf | Varun Mohan (co-founder and CEO): https://www.lennysnewsletter.com/p/the-untold-story-of-windsurf-varun-mohan• Microsoft CPO: If you aren’t prototyping with AI, you’re doing it wrong | Aparna Chennapragada: https://www.lennysnewsletter.com/p/microsoft-cpo-on-ai• 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• Granola: https://www.granola.ai/• 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• 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• Fidji Simo on LinkedIn: https://www.linkedin.com/in/fidjisimo/• Airtable: https://www.airtable.com/• George Lee on LinkedIn: https://www.linkedin.com/in/geolee/• Andrew Chen on LinkedIn: https://www.linkedin.com/in/andrewchen/• Lauryn Motamedi on LinkedIn: https://www.linkedin.com/in/laurynmotamedi/• Twilio: https://www.twilio.com/• Nick Turley on LinkedIn: https://www.linkedin.com/in/nicholasturley/• Ian Silber on LinkedIn: https://www.linkedin.com/in/iansilber/• Thomas Dimson on LinkedIn: https://www.linkedin.com/in/thomasdimson/• Joey Flynn on LinkedIn: https://www.linkedin.com/in/joey-flynn-8291586b/• Ryan O’Rourke’s website: https://www.rourkery.com/• Joanne Jang on LinkedIn: https://www.linkedin.com/in/jangjoanne/• Behind the founder: Marc Benioff: https://www.lennysnewsletter.com/p/...
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    1 hr and 55 mins
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