Podcast
Cheeky Pint
Hosted by Stripe · EN
Stripe cofounder John Collison interviews founders, builders, and leaders over a pint.
35episodes
Episodes
Newest firstAll episodes
How to build a $16B car company with RJ Scaringe, founder of Rivian
Oct 1401:08:48Summary readyRJ Scaringe, founder and CEO of Rivian, sits down for a cheeky pint with John Collison to discuss what it takes to build a car company from scratch, developing the first electric pickup truck, the shift to a software-defined zonal architecture, Rivian's AI-driven approach to autonomy, and the strategy behind their recent $5.8 billion deal with Volkswagen.Timestamps(00:00) Gen 1(12:32) Gen 2(18:37) Developing the first electric pickup truck(27:36) John pitches some car features(36:46) Stripe’s payment methods(37:54) Autonomous driving(44:51) Component progress(53:17) The new economics of cars(01:01:11) Manufacturing in the US
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Tobi Lütke is still captivated by internet commerce, 20 years later
Oct 601:42:55Summary readyShopify founder and CEO Tobi Lütke joins John Collison to discuss the philosophies driving one of the internet’s most foundational companies. Tobi shares his perspective on why companies are a form of technology, how internal tools and "opinionated software" shape an organization's culture and accelerate its evolution, and why the best gift is finding a beautiful, unsolvable problem.Show notes[Buy] Momax: 140W Universal Travel Adapter[Read] Benjamin Bloom: The 2 Sigma Problem[Buy] Ikigai: vitamin cases [Read] Kevin Kelly: 1,000 True Fans[Read] Erich Gamma: Design Patterns [Read] Charles Calomiris: Fragile by Design[Listen] Business Breakdowns: Formula One[Watch] Netflix: Formula 1: Drive to Survive[Read] Mark Robichaux: Cable CowboyKey Moments(00:00) Intro(07:07) How internal software shapes culture(16:32) The Shopify vision(27:49) Peak transaction capacity(34:36) Agentic commerce(49:15) Shop Pay(55:29) Stablecoins(59:20) Stripe + Shopify(1:12:23) Learning from the Coinbase board(1:17:23) Is Tobi ungovernable?(1:25:02) Entrepreneurship(1:31:50) Advice for Mark Carney(1:36:40) Motor racing
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Marc Andreessen and Charlie Songhurst on the past, present, and future of Silicon Valley
Oct 102:07:56Summary readyMarc Andreessen, cofounder of Netscape and Andreessen Horowitz, sits down for a Cheeky Pint with John Collison and Charlie Songhurst to discuss the history of Silicon Valley, spotting bubbles in real time, the "Elon method" of management, and why the mistakes that haunt you are the companies you don't invest in.Show notes:Roger Lowenstein: When Genius Failed: The Rise and Fall of Long-Term Capital ManagementDavid Swensen: Pioneering Portfolio ManagementIan M Banks: Consider Phlebas: A Culture NovelWalter Isaacson: Elon MuskThomas Rid: Rise of the Machines: A Cybernetic HistoryGeorge McGovern: A Politician's Dream Is a Businessman's Nightmare, WSJSteve Blank: The Secret History of Silicon ValleyTracy Kidder: The Soul of a New MachineJohn Perry Barlow: A Declaration of the Independence of CyberspaceMartin Gurri: Revolt of the PublicJohn Malone: Born to Be WiredFull transcript on Substack: https://cheekypint.substack.com/p/marc-andreessen-and-charlie-songhurst Subscribe to Cheeky PintSpotify: https://open.spotify.com/show/2IHbGJJMpiFoz5YrvRfTFwApple Podcasts: https://podcasts.apple.com/us/podcast/cheeky-pint/id1821055332Substack: https://cheekypint.substack.com/Key moments(00:00) Marc needs to know: what is a cheeky pint?(04:30) Are we in a bubble?(14:55) Do VCs matter?(19:01) The history of Silicon Valley(32:25) How Digital Research almost made it(39:02) A bear case on the internet(59:52) AI productivity(01:12:10) Stripe + AI(01:13:08) Crypto(01:24:08) Should a16z start a hedge fund?(01:29:51) Big companies(01:35:33) Boards(01:40:27) The Elon method(01:52:59) The future of media
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Des Traynor on reinventing Intercom twice and the “four horsemen” of good AI companies
Sep 2401:18:20Summary readyDes Traynor, cofounder of Intercom, sits down for a Cheeky Pint with John Collison to discuss the growth of Fin (Intercom’s AI customer service agent), why selling AI products is hard, advice for product marketers, and cofounder dynamics.Full transcript on Substack: https://cheekypint.substack.com/p/des-traynor-on-reinventing-intercomTimestamps: (00:00) Intro(02:58) Reinventing Intercom(06:31) Fin(18:06) 1M resolutions a week(24:22) Selling AI(29:34) Product marketing(37:18) Listening to users(44:14) Usage-based billing(45:14) Advice for startups(52:09) AI pricing(01:07:27) Cofounder dynamics(01:11:04) Predictors of company success(01:15:56) How AI-native is Intercom?
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Ambrook CEO Mackenzie Burnett on American agriculture, rural resilience, and carrying 50lbs of fresh pork on Amtrak
Sep 1700:54:53Summary readyMackenzie Burnett joins John Collision to talk about American agriculture, labor and immigration challenges, building rural resilience, ERPs, and the principle of money movement. She also shares some feedback for Stripe. Show notes:Where Soil is Holy, and Climate Change Is Seldom MentionedFarming goes digitalThe End of Accounting and the Path Forward for Investors and Managers Timestamps:(00:00) Introducing Ambrook(05:37) Serving farmers(19:25) Building rural resilience(21:49) The economics of ag(28:03) If Mackenzie ran the USDA(30:53) Vertical SaaS(34:49) The wonders of accounting(38:41) Ambrook-as-fintech(44:00) If Mackenzie ran Stripe(50:53) Joshua Kushner and Dylan Field
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Zipline CEO Keller Cliffton on air-dropping blood to Rwandan hospitals and getting to 50,000 aircraft per year
Sep 1001:14:12Summary readyKeller Cliffton joins John Collison to talk about Zipline’s journey to 115 million miles flown, the lost art of American airplanes, building 50k drones a year in California, getting to 99.9% reliability, and US vs. Chinese manufacturing. Books referenced:The Right Stuff by Tom WolfeSkunk Works by Ben RichApple in China by Patrick McGeeTimestamps(00:00) Intro(00:45) 115 million miles flown(04:10) Why drone delivery took so long(07:38) Getting started in Rwanda(13:31) 51% reduction in maternal mortality(15:33) Access vs waste(21:45) Scaling globally(24:05) Zipline’s Platform 1 (25:50) The Right Stuff(27:22) Drone design and safety(30:12) Getting to 99.9% reliability(34:39) Multimodal logistics(38:15) Zipline’s Platform 2(44:03) US drone regs and the FAA(48:02) Progress and stagnation in US aviation(51:30) If Keller ran the FAA(54:24) 30% WoW growth in Texas(58:25) Why Texas and not California?(01:00:28) Building 50k drones in California(01:06:18) US vs Chinese manufacturing(01:11:30) Advice for hardtech founders
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Cognition CEO Scott Wu on acquiring Windsurf, AI replacing engineers, and the Moneyball-ification of everything
Aug 2700:57:53Summary readyScott Wu joins John Collison to talk about Cognition’s AI software engineer, the Moneyball-ification of everything, math competitions with Alexandr Wang in 6th grade, acquiring Windsurf over a weekend, whether coding tools will be replaced by the labs, and why he thinks we already have AGI.Full transcript on Substack: https://open.substack.com/pub/cheekypint/p/cognition-ceo-scott-wu-on-acquiringTimestamps(00:00) Intro(01:13) Early life and maths competitions(03:47) Addepar job as a high schooler(05:43) Where are all the young founders?(08:45) Moneyball-ification of everything(11:42) Cognition’s AI software engineer, Devin(15:46) Essential and accidental complexity(17:59) How Devin works with enterprises(19:48) IDE productivity(21:56) Nihilist computer use argument (25:55) Benchmarking Devin (27:15) Market structure (30:32) Agent economy(37:21) Cognition’s team of founders(39:31) Jevons paradox and software (42:00) When will we see AI UIs?(45:52) “I think we have AGI”(47:03) Windsurf deal(52:37) M&A in AI(54:21) Cognition’s culture (55:48) Learning as a CEO(57:12) Scott’s information diet
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Coinbase CEO Brian Armstrong on bitcoin going to $1 million, electing a pro-crypto Congress, and Jamie Dimon
Aug 2001:16:31Summary readyBrian Armstrong joins John Collison to talk about what’s happening behind the scenes at Coinbase: battling North Korean hackers, war stories from early scaling, confronting people who won’t use AI to code, Coinbase becoming people’s primary financial account, and why banks are now embracing crypto.Full episode transcript on Substackhttps://cheekypint.substack.com/p/coinbase-ceo-brian-armstrong-on-bitcoinTimestamps(00:00) Intro(01:14) How Coinbase won the exchange market(06:22) Losing money on every bitcoin purchase(10:54) North Korean hackers(14:54) The Everything Exchange(17:39) Crypto will be bigger than gold(19:22) Stablecoin adoption(23:28) Jamie Dimon and big banks on crypto(26:44) Coinbase as your primary financial account(27:53) Neobanks(29:41) Bitcoin going to $1 million(33:16) Crypto in an investment portfolio(34:43) GENIUS Act(37:10) Electing a pro-crypto Congress(45:24) Reforming accredited investor rules(48:33) Squashing scams(50:11) Bitcoin preserving the American experiment(57:09) Balaji Srinivasan(01:01:05) The mission-first company announcement(01:05:50) How does Coinbase focus?(01:07:44) Venture bets and Brian vetoing USDC(01:12:02) Brian’s AI coding mandate(01:15:13) Advice for Stripe
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Robinhood CEO Vlad Tenev on tokenizing private companies, changing the SEC, and Frank Slootman
Aug 1301:05:50Summary readyVlad Tenev joins John Collison to discuss Bulgarian hyperinflation, Robinhood Banking, details from the GameStop saga—including advice from Marc Benioff, Mark Zuckerberg, and Elon Musk, payment for order flow economics and Michael Lewis’ Flash Boys, his approach to leadership through the Frank Slootman framework, and how he would change the SEC.Full episode transcript on Substack: https://cheekypint.substack.com/p/robinhood-ceo-vlad-tenev-makes-hisTimestamps(00:00) Intro(00:58) Hyperinflation in Bulgaria(04:07) Stablecoins (05:41) Home country bias in investing(06:59) Robinhood’s origins(11:23) What the book Flash Boys got wrong(16:11) Options vs. equities(17:38) Robinhood Gold(19:34) Robinhood Banking (22:04) GameStop advice from Benioff, Zuck, and Elon(26:40) Impact of retail investors on capital markets(31:21) Where retail dollars are coming from(32:10) The gamification narrative(34:17) Tokenizing private companies(41:57) Vlad makes his pitch to tokenize Stripe(45:00) Prediction markets: tennis, the pope, and AI(49:26) If Vlad ran the SEC(51:15) How does Robinhood ship so fast?(52:38) Remote work and Robinhood’s founder community (55:39) “What would Frank Slootman do?”(57:32) Active traders(59:46) Killing Robinhood’s cash card(01:02:36) Harmonic and mathematical superintelligence
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Anthropic CEO Dario Amodei on designing AGI-pilled products, model economics, and 19th-century vitalism
Aug 6, 202501:02:51Summary readyDario Amodei joins John Collison to talk about Anthropic's growth to ~$5 billion in ARR, how AI models show capitalistic impulses, predictions for an agentic future, the economics of model businesses, and the 19th-century concept of vitalism.Full episode transcript on Substack: https://cheekypint.substack.com/p/a-cheeky-pint-with-anthropic-ceoTimestamps(00:00) Intro(00:50) Working with your sibling(01:43) Building Anthropic with 7 cofounders(02:52) ~$5 billion in ARR and vertical applications of products(07:18) Developing a platform-first company(10:08) Working with the DoD(11:11) Proving skeptics wrong about revenue projections(13:13) Capitalistic impulses of AI models(15:43) AI market structure and players(16:56) AI models as standalone P&Ls(20:48) The data wall and styles of learning(22:20) AI talent wars(26:04) Pitching Anthropic’s API business to investors(27:49) Cloud providers vs. AI labs(29:05) AI customization and Claude for enterprise(33:01) Dwarkesh’s take on limitations(36:12) 19th-century notion of vitalism(37:27) AI in medicine, customer service, and taxes(40:59) How to solve for hallucinations(42:41) The double-standard for AI mistakes(44:14) Evolving from researcher to CEO(46:59) Designing AGI-pilled products(47:57) AI-native UIs(50:09) Model progress and building products(52:22) Open-source models(54:43) Keeping Anthropic AGI-pilled(57:11) AI advancements vs. safety regulations(01:02:04) How Dario uses AI
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