Episodes

  • 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)

    Rapidly test and validate any startup idea with the 2-day Foundation Sprint (from the creators of the Design Sprint) | Jake Knapp & John Zeratsky (Character Capital)
    Jul 13 2025
    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-...
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    1 hr and 42 mins
  • Solo founder, $80M exit, 6 months: The Base44 bootstrapped startup success story | Maor Shlomo

    Solo founder, $80M exit, 6 months: The Base44 bootstrapped startup success story | Maor Shlomo
    Jul 6 2025
    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 podcast@lennyrachitsky.com.Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com
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    1 hr and 32 mins
  • 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
  • AI prompt engineering in 2025: What works and what doesn’t | Sander Schulhoff (Learn Prompting, HackAPrompt)

    AI prompt engineering in 2025: What works and what doesn’t | Sander Schulhoff (Learn Prompting, HackAPrompt)
    Jun 19 2025
    Sander Schulhoff is the OG prompt engineer. He created the very first prompt engineering guide on the internet (two months before ChatGPT’s release) and recently wrote the most comprehensive study of prompt engineering ever conducted (co-authored with OpenAI, Microsoft, Google, Princeton, and Stanford), analyzing over 1,500 academic papers and covering more than 200 prompting techniques. He also partners with OpenAI to run what was the first and is the largest AI red teaming competition, HackAPrompt, which helps discover the most state-of-the-art prompt injection techniques (i.e. ways to get LLMS to do things it shouldn’t). Sander teaches AI red teaming on Maven, advises AI companies on security, and has educated millions of people on the most state-of-the-art prompt engineering techniques.In this episode, you’ll learn:1. The 5 most effective prompt engineering techniques2. Why “role prompting” and threatening the AI no longer works—and what to do instead3. The two types of prompt engineering: conversational and product/system prompts4. A primer on prompt injection and AI red teaming—including real jailbreak tactics that are still fooling top models5. Why AI agents and robots will be the next major security threat6. How to get started in AI red teaming and prompt engineering7. Practical defense to put in place for your AI products—Brought to you by:Eppo—Run reliable, impactful experimentsStripe—Helping companies of all sizes grow revenueVanta—Automate compliance. Simplify security—Where to find Sander Schulhoff:• X: https://x.com/sanderschulhoff• LinkedIn: https://www.linkedin.com/in/sander-schulhoff/• Website: https://sanderschulhoff.com/• AI Red Teaming and AI Security Masterclass on Maven: https://bit.ly/44lLSbC• Free Lightning Lesson “How to Secure Your AI System” on 6/24: https://bit.ly/4ld9vZL—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 Sander Schulhoff(04:29) The importance of prompt engineering(06:30) Real-world applications and examples(10:54) Basic prompt engineering techniques(23:46) Advanced prompt engineering techniques(29:00) The role of context and additional information(39:24) Ensembling techniques and thought generation(49:48) Conversational techniques for better results(50:46) Introduction to prompt injection(52:27) AI red teaming and competitions(54:23) The growing importance of AI security(01:02:45) Techniques to bypass AI safeguards(01:05:21) Challenges in AI security and future outlook(01:18:33) Misalignment and AI's potential risks(01:25:03) Final thoughts and lightning round—Referenced:• Reid Hoffman’s tweet about using AI agents: https://x.com/reidhoffman/status/1930416063616884822• AI Engineer World’s Fair: https://www.ai.engineer/• What Is Artificial Social Intelligence?: https://learnprompting.org/blog/asi• Devin: https://devin.ai/• Cursor: https://www.cursor.com/• Inside Devin: The world’s first autonomous AI engineer that’s set to write 50% of its company’s code by end of year | Scott Wu (CEO and co-founder of Cognition): https://www.lennysnewsletter.com/p/inside-devin-scott-wu• 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• Granola: https://www.granola.ai/• 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 & 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• Technique #3: Examples in Prompts: From Zero-Shot to Few-Shot: https://learnprompting.org/docs/basics/few_shot?srsltid=AfmBOor2owyGXtzJZ8n0fJVCctM7UPZgZmH-mBuxRW4t9-kkaMd3LJVv• The Prompt Report: Insights from the Most Comprehensive Study of Prompting Ever Done: https://learnprompting.org/blog/the_prompt_report?srsltid=AfmBOoo7CRNNCtavzhyLbCMxc0LDmkSUakJ4P8XBaITbE6GXL1i2SvA0• State-of-the-Art Prompting for AI Agents | Y Combinator: https://www.youtube.com/watch?v=DL82mGde6wo• Use XML tags to structure your prompts: https://docs.anthropic.com/en/docs/build-with-claude/prompt-engineering/use-xml-tags• Role Prompting: https://learnprompting.org/docs/basics/roles?srsltid=...
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    1 hr and 38 mins
  • How to build a team that can “take a punch”: A playbook for building resilient, high-performing teams | Hilary Gridley (Head of Core Product, Whoop)

    How to build a team that can “take a punch”: A playbook for building resilient, high-performing teams | Hilary Gridley (Head of Core Product, Whoop)
    Jun 15 2025
    Hilary Gridley is the Head of Core Product at WHOOP and a passionate thought leader in leveraging AI to elevate product teams and management practices. With extensive experience tackling challenging problems in regulated industries and high-stakes environments, Hilary emphasizes the importance of building resilience and adaptability within teams. Previously, she was a senior director of product at Big Health and a senior product marketing manager at Dropbox.In this episode, you’ll learn:• How to teach your team to be able to “take a punch”• Specific tactics to counter negative perceptions and reframe setbacks productively• Powerful behavioral strategies to form positive habits• Practical approaches for creating space in your workday to encourage creativity and deep thinking• The underestimated potential of AI in accelerating your personal and professional growth• Why you’re not the protagonist at your company (and why that’s liberating)• How WHOOP uses reward loops to drive real behavior change—Brought to you by:WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUsPersona—A global leader in digital identity verificationAttio—The powerful, flexible CRM for fast-growing startups—Where to find Hilary Gridley:• X: https://x.com/yourgirlhils• LinkedIn: https://www.linkedin.com/in/hilarygridley/• Newsletter: https://hils.substack.com/• Maven course: https://maven.com/hilary-gridley/ai-powered-people-management—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) Hilary’s background(04:31) Teaching teams to handle criticism and setbacks(17:57) Behavioral activation and mental health in the workplace(22:59) The importance of putting yourself out there(27:51) Transparency and communication in leadership(38:10) How to respectfully disagree with your manager(41:49) How to use “magic questions” to decode how people think(49:54) Why you’re not the protagonist at your company(52:48) Aligning with the CEO's vision(01:01:02) Building effective habits(01:11:14) Promoting team well-being(01:14:28) Creating space for creativity(01:20:45) AI’s role in accelerating learning(01:30:35) Pivotal career moments(01:37:21) Lessons from failure(01:39:49) Exciting new features of WHOOP 5.0(01:44:19) Lightning round and final thoughts—Referenced:• How to become a supermanager with AI: https://www.lennysnewsletter.com/p/how-to-become-a-supermanager-with• How custom GPTs can make you a better manager | Hilary Gridley (Head of Core Product at Whoop): https://www.lennysnewsletter.com/p/how-custom-gpts-can-make-you-a-better-manager• WHOOP: https://www.whoop.com/• Big Health: https://www.bighealth.com/• What is behavioral activation?: https://www.medicalnewstoday.com/articles/behavioral-activation• Will Ahmed on LinkedIn: https://www.linkedin.com/in/willahmed/• Joe Gebbia on LinkedIn: https://www.linkedin.com/in/jgebbia/• Zach Abrams on LinkedIn: https://www.linkedin.com/in/zacharyabrams/• Coinbase: https://www.coinbase.com/• Bridge: https://www.bridge.xyz/• Stripe: https://stripe.com/• The paths to power: How to grow your influence and advance your career | Jeffrey Pfeffer (author of 7 Rules of Power, professor at Stanford GSB): https://www.lennysnewsletter.com/p/the-paths-to-power-jeffrey-pfeffer• Paths to Power course: https://jeffreypfeffer.com/wp-content/uploads/2019/10/Pfeffer-OB377-Course-Outline-2018.pdf• VO₂ max: https://en.wikipedia.org/wiki/VO2_max• Peter Attia on X: https://x.com/PeterAttiaMD• Hilary Gridley’s 30 days of GPT: https://docs.google.com/spreadsheets/d/1zJ4rbi9YcQuGqGxc6-AQD0-44oT9l4Eyono0AdpgJbA/edit?gid=0#gid=0• The Handle Bar in Boston: https://www.thehandlebarstudios.com/ourstudios/charlestown• From chalkboards to chatbots: Transforming learning in Nigeria, one prompt at a time: https://blogs.worldbank.org/en/education/From-chalkboards-to-chatbots-Transforming-learning-in-Nigeria• Product Management Logic Coach GPT: https://chatgpt.com/g/g-673290301700819084afa36bdbcdfa3b-product-management-logic-coach• Dropbox: https://www.dropbox.com/• WHOOP Advanced Labs: https://www.whoop.com/us/en/waitlist/?srsltid=AfmBOor2pP5qC3n7I23Z0ZIrYE99CjAKT9xSHQxbuyxmz_wFUBGH3e-n• Negative capability: https://en.wikipedia.org/wiki/Negative_capability• John Keats: https://en.wikipedia.org/wiki/John_Keats• The Rehearsal: https://www.hbo.com/the-rehearsal• Zwift: https://www.zwift.com/• Beavis and Butthead Do ‘Creep’: https://www.youtube.com/watch?v=zv_gSmH0Ieg• “Sea Grapes” by Derek Walcott: https://www.poetryfoundation.org/poems/57111/sea-grapes• Free month of WHOOP: https://join.whoop.com/us/en/hilary/—Recommended books:• 7 Rules of Power: https://jeffreypfeffer.com/books/7-rules-of-power/• Outlive: The Science and Art of Longevity: https://...
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    1 hr and 55 mins
  • 35 years of product design wisdom from Apple, Disney, Pinterest, and beyond | Bob Baxley

    35 years of product design wisdom from Apple, Disney, Pinterest, and beyond | Bob Baxley
    Jun 12 2025
    Bob Baxley is a design leader who has shaped products used by billions at Apple, Pinterest, Yahoo, and ThoughtSpot. During his eight years at Apple, he led design for the online store and the App Store, and witnessed the iPhone’s transformative launch while working under Steve Jobs. A student of history turned software craftsman, Bob discovered his calling after exploring photography, filmmaking, and music, ultimately recognizing software as the most powerful creative medium of our time. Bob champions the moral obligation designers have to reduce frustration in people’s daily digital interactions.What you’ll learn:• Why design should report to engineering, not product• The “Beatles principle”—why the best products come from teams of 4 to 6, not 40 to 60• How to create design tenets vs. principles (with real examples)• The counterintuitive reason to delay drawing or prototyping as long as possible• Why software is fundamentally a medium, like film or music (not just a tool)• Why Bob “bounced off the culture” at Pinterest, and lessons from failure• The lunar landing story that teaches us about championing radical ideas• How to evaluate if a company truly values design before joining• The moral obligation of software makers to build great products—This entire episode is brought to you by Stripe—helping companies of all sizes grow revenue.—Where to find Bob Baxley:• Instagram: https://www.instagram.com/baxley/• LinkedIn: https://www.linkedin.com/in/bbaxley/• Website: http://www.bobbaxley.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 Bob Baxley(03:52) Apple's lasting culture(06:15) Navigating unique company cultures(13:19) Finding a company that truly values your role(15:46) What is design?(17:17) How to help founders understand the value of design(23:08) How to align product managers and designers(26:31) Design reporting to engineering(30:54) Integrating engineers early in the design process(33:43) The maker mindset(35:14) Challenging the assumption that design is time-intensive(38:04) Design tenets vs. design principles(45:25) The moral obligation of great design(51:48) Understanding software as a medium(01:01:20) Reducing ambiguity for product teams(01:07:04) Giving designers space for creativity(01:08:48) The "primal mark" concept(01:12:05) AI prototyping tools: benefits and risks(01:17:00) AI as a life coach(01:21:22) Life lessons from the Apollo program(01:28:24) Lightning round and final thoughts—Referenced:• Steve Jobs: https://en.wikipedia.org/wiki/Steve_Jobs• Walt Disney: https://en.wikipedia.org/wiki/Walt_Disney• Pinterest: https://www.pinterest.com/• X: https://x.com/• Uber: https://www.uber.com/• Airbnb: https://www.airbnb.com/• Slack: https://slack.com/• Ed Catmull on X: https://x.com/edcatmull• John Lasseter on X: https://x.com/johnlasseter5• Apple patented a pizza box, for pizzas: https://www.theverge.com/2017/5/16/15646154/apple-pizza-box-patent-come-on• Humane: https://en.wikipedia.org/wiki/Humane_Inc.• Jony Ive: https://en.wikipedia.org/wiki/Jony_Ive• Tony Fadell on LinkedIn: https://www.linkedin.com/in/tonyfadell/• Hiroki Asai on LinkedIn: https://www.linkedin.com/in/hiroki-asai-a44137110/• Tim Cook on X: https://x.com/tim_cook• ThoughtSpot: https://www.thoughtspot.com/• Ben Silbermann on LinkedIn: https://www.linkedin.com/in/silbermann/• Ajeet Singh on LinkedIn: https://www.linkedin.com/in/ajeetsinghmann/• Honeywell: https://www.honeywell.com• IDEO: https://www.ideo.com/• Nutanix: https://www.nutanix.com/• Lego: https://www.lego.com/• Leica: https://leica-camera.com/• Porsche: https://www.porsche.com/• Patagonia: https://www.patagonia.com• Brian Eno’s website: https://www.brian-eno.net/• Scenius: why creatives are stronger together: https://thecreativelife.net/scenius/• The Beatles website: https://www.thebeatles.com/• Disneyland: https://disneyland.disney.go.com/destinations/disneyland/• Tomorrowland: https://disneyland.disney.go.com/destinations/disneyland/tomorrowland/• Unconventional product lessons from Binance, N26, Google, more | Mayur Kamat (CPO at N26, ex-Binance Head of Product): https://www.lennysnewsletter.com/p/unorthodox-product-lessons-from-n26-and-more• Larry Page: https://en.wikipedia.org/wiki/Larry_Page• Sergey Brin: https://en.wikipedia.org/wiki/Sergey_Brin• Design Principles: https://principles.design/• Tableau: https://www.tableau.com/• Figma: https://www.figma.com/• Target self-checkout: https://corporate.target.com/press/fact-sheet/2024/03/checkout-improvements• 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/...
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    1 hr and 42 mins