All Episodes

Zach Abrams, the CEO and cofounder of Bridge, the leading stablecoin orchestration platform, and Henri Stern, CEO and cofounder of Privy, the leading crypto wallet infrastructure, sit down with John to discuss the future of stablecoins, issuing, and what it will take for crypto to become ubiquitous. Both companies recently joined Stripe, and are uniquely positioned to dissect how crypto is changing financial infrastructure.Key moments(00:00) Introducing Bridge + Privy(06:39) How stablecoins are being used today(14:27) US Dollar dominance(25:50) The future of banking(34:35) Blockchains(42:27) Building a modular stack(47:14) Open issuance(56:55) M&A(01:11:02) The future of stablecoins

DescriptionCasey Handmer is the founder of Terraform Industries, who is developing a machine that makes synthetic natural gas from sunlight and air. He joins the podcast to explain his solar maximalist worldview, why he believes solar costs will drop another 10x, and the core physics that doomed Hyperloop from the start. They also discuss the lessons of the underappreciated industrialist Henry Kaiser, Casey's new venture in solar-powered desalination, his grand plan to refill the Salton Sea, and why he believes "hard-edged" leaders are essential for hardware success.Show notes[Read] Ashlee Vance: Elon Musk    [Read] Francis Spufford: Red plenty[Listen] Beneath the Surface, Episode 2 : Salton Sea [Read] Marc Reisner: Cadillac Desert[Read] Albert P. Heiner: Henry J. Kaiser[Read] Mark S. Foster: Henry Kaiser[Read] Ernest K. Gann: Fate is the Hunter[Read] Captain W. E. Johns: Biggles: The Camels are ComingKey moments(00:00) Intro(02:28) Henry Kaiser(08:49) Introducing Terraform(13:08) Where electricity won’t work(16:50) The solar maximalist perspective(22:57) Terraformer Mark One(27:49) The role of intervention(37:30) American dynamism(47:36) The Origins of Efficiency, by Brian Potter(48:33) Children and education(37:30) American dynamism(55:15) Desalination(01:08:16) Lessons from leadership

Seasoned public and private investor Dan Sundheim sits down with John to discuss the harrowing GameStop short squeeze, waking up at 3am for the European market open, and the emotional asymmetry of managing billions of dollars. They cover why he thinks successful private companies should avoid the public markets, the real genius of Elon Musk's business approach, and the pattern recognition that comes from years of investing. This is a rare, candid look into the strategies and mindset of a top public markets investor.Show notes[Read] The Essays of Warren Buffett: Lessons for Corporate America by Lawrence A. Cunningham[Read] The Buffett Partnership Letters (1957-1970)[Read] Value Investors Club (VIC)Timestamps(00:00) The D1 operating model(07:54) Getting it wrong on NFLX(11:44) What makes a good stock picker(18:16) Portfolio-building(24:35) GameStop(35:57) The art of short-selling(41:48) How to spot a turnaround(47:12) Waking up at 3 AM(53:14) Money management(59:31) Dan’s 10-year hands-off stock pick(01:09:52) China(01:14:44) Are we in a bubble?(01:20:41) SpaceX(01:25:04) Investing in private companies(01:32:55) Thoughts on the banking industry(01:35:58) Advice for budding investors

RJ 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

Shopify 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

Marc 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

Des 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?

Mackenzie Burnett joins John Collison 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 Full transcript on Substack: https://cheekypint.substack.com/p/ambrook-ceo-mackenzie-burnett-on 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

Keller 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

Scott 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

Brian 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

Vlad 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

Dario 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

Pieter Levels joins John Collison to discuss building successful online businesses as a digital nomad, thoughts on European accelerationism, and Pieter’s unconventional methods and philosophy as a bootstrapped founder making over $3 million per year.Full episode transcripthttps://cheekypint.transistor.fm/4/transcriptTimestamps(00:00) Intro(00:37) Pieter’s resume(01:33) Trying to make money online as a 12 year old(02:43) Being one of the first YouTube creators(03:18) Who should indie hack(04:31) What Pieter hates about VC-backed businesses(07:51) Who is digital nomading for?(09:15) Learning from @patio11(10:17) 125k tweets and the brand of @levelsio(10:59) Getting referrals from ChatGPT(11:43) What Pieter automates with AI(13:02) Investing and home country bias(15:05) Hacking thermostats(15:57) EU acceleration movement(18:34) Entrepreneurship in the EU(19:26) Pieter's reflections on Stripe’s API(21:21) Looking 5 years into the future

The Bot Company founder and CEO Kyle Vogt—who also cofounded Twitch and Cruise—joins John Collison to talk about applying AI to home robots, the similarities between robotics and self-driving, and why the next $100 billion company will have fewer than 100 people.Full episode transcripthttps://cheekypint.transistor.fm/3/transcriptTimestamps(00:00) Intro(00:38) The Bot Company pitch(02:05) Single-task vs. multi-task robots(04:27) What is the Turing test for robotics?(05:52) Why this time is different for home robots(08:42) The last mile in robotics and self-driving(09:47) Viral demos and hype cycles(10:38) Commercializing frontier tech(13:06) Self-driving CapEx(14:15) Regulatory hurdles(16:18) Tesla vs. Waymo(19:21) Why Kyle regrets selling Cruise(21:39) The next $100 billion company

Greg Brockman—OpenAI cofounder and Stripe's first engineer—joins John Collison to talk about research-driven product development, an early moment he thought OpenAI was doomed, S curves in AI advancement, and energy bottlenecks.Full episode transcript:https://cheekypint.transistor.fm/1/transcriptTimestamps(00:00) Intro(02:51) Was OpenAI the first company to take the scaling hypothesis seriously? (04:53) Lessons from Dota about deep learning (08:08) What is a good new Turing test?(08:57) Personalization in AI (09:57) Research-driven product development(10:26) An early moment OpenAI felt doomed (15:01) OS limits on AI product development(17:59) When will AI make novel advancements in math or science?(20:03) Energy bottlenecks(22:30) S curves in AI advancement (24:00) AI coding (26:25) Refactoring as a killer AI use case(27:26) How OpenAI decides what products to built(28:53) Growing up in North Dakota(30:17) How far away is AGI?

Susan Li of Meta—the youngest chief financial officer of a Fortune 100 company—joins John Collison to talk about capital allocation, managing investors, and how Mark Zuckerberg has changed over the 17 years of working together.Full episode transcripthttps://cheekypint.transistor.fm/2/transcriptTimestamps(00:00) Intro(01:20) Early education and career(02:15) Lessons from Michael Grimes at Morgan Stanley(03:12) Leadership traits and succession planning at Meta(06:05) Mark Zuckerberg’s leadership and culture of feedback(09:06) Financial forecasting and capital allocation(14:18) ROI on Meta’s portfolio of bets(15:05) Investor sentiment in 2022(17:49) The story behind the “free cash flow” hats(18:58) CapEx trends in the AI era(21:48) A memorable earnings call(24:16) Challenges of allocating compute vs headcount budgets (26:55) AI’s impact on productivity and operations

John sits down with founders and builders over a pint—Greg Brockman (cofounder of OpenAI), Susan Li (chief financial officer at Meta), Kyle Vogt (founder of The Bot Company and cofounder of Twitch and Cruise), and Pieter Levels (indie hacker).Watch Cheeky Pint on YouTube: https://youtube.com/@stripe.