Cheeky Pint

Stripe

Stripe cofounder John Collison interviews founders, builders, and leaders over a pint.

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35 episodes
Updated April 27
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Episodes35

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Oct 14, 2025 · 1 hr 8 min
How to build a $16B car company with RJ Scaringe, founder of Rivian
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
Oct 6, 2025 · 1 hr 42 min
Tobi Lütke is still captivated by internet commerce, 20 years later
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 Cowboy Key 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
Oct 1, 2025 · 2 hr 7 min
Marc Andreessen and Charlie Songhurst on the past, present, and future of Silicon Valley
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 Management David Swensen: Pioneering Portfolio Management Ian M Banks: Consider Phlebas: A Culture Novel Walter Isaacson: Elon Musk Thomas Rid: Rise of the Machines: A Cybernetic History George McGovern: A Politician's Dream Is a Businessman's Nightmare, WSJ Steve Blank: The Secret History of Silicon Valley Tracy Kidder: The Soul of a New Machine John Perry Barlow: A Declaration of the Independence of Cyberspace Martin Gurri: Revolt of the Public John Malone: Born to Be Wired Full transcript on Substack: https://cheekypint.substack.com/p/marc-andreessen-and-charlie-songhurst Subscribe to Cheeky Pint Spotify: https://open.spotify.com/show/2IHbGJJMpiFoz5YrvRfTFw Apple Podcasts: https://podcasts.apple.com/us/podcast/cheeky-pint/id1821055332 Substack: 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
Sep 24, 2025 · 1 hr 18 min
Des Traynor on reinventing Intercom twice and the “four horsemen” of good AI companies
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-intercom Timestamps: (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?
Sep 17, 2025 · 54 min
Ambrook CEO Mackenzie Burnett on American agriculture, rural resilience, and carrying 50lbs of fresh pork on Amtrak
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 Mentioned Farming goes digital The 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
Sep 10, 2025 · 1 hr 14 min
Zipline CEO Keller Cliffton on air-dropping blood to Rwandan hospitals and getting to 50,000 aircraft per year
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 Wolfe Skunk Works by Ben Rich Apple in China by Patrick McGee Timestamps (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
Aug 27, 2025 · 57 min
Cognition CEO Scott Wu on acquiring Windsurf, AI replacing engineers, and the Moneyball-ification of everything
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-acquiring Timestamps (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
Aug 20, 2025 · 1 hr 16 min
Coinbase CEO Brian Armstrong on bitcoin going to $1 million, electing a pro-crypto Congress, and Jamie Dimon
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 Substack https://cheekypint.substack.com/p/coinbase-ceo-brian-armstrong-on-bitcoin Timestamps (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
Aug 13, 2025 · 1 hr 5 min
Robinhood CEO Vlad Tenev on tokenizing private companies, changing the SEC, and Frank Slootman
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-his Timestamps (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
Aug 6, 2025 · 1 hr 2 min
Anthropic CEO Dario Amodei on designing AGI-pilled products, model economics, and 19th-century vitalism
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-ceo Timestamps (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
Jul 9, 2025 · 22 min
Serial entrepreneur Pieter Levels on building in public and living as a digital nomad
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 transcript https://cheekypint.transistor.fm/4/transcript Timestamps (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
Jun 25, 2025 · 22 min
The Bot Company founder and CEO Kyle Vogt on home robots and why he’ll never sell another company
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 transcript https://cheekypint.transistor.fm/3/transcript Timestamps (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
Jun 18, 2025 · 31 min
OpenAI cofounder Greg Brockman on the scaling hypothesis and refactoring as a killer AI use case
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/transcript Timestamps (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?
Jun 18, 2025 · 29 min
Meta CFO Susan Li on headcount vs. GPU allocation, “free cash flow” hats, and almost becoming a PM
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 transcript https://cheekypint.transistor.fm/2/transcript Timestamps (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
Jun 16, 2025 · 56 sec
Cheeky Pint hosted by Stripe cofounder John Collison
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.