Podcasts · Technology · Business

Cheeky Pint

Stripe

39 episodes

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

Episodes

  1. The airline CEO putting Starlink on every plane

    · 1 h 20 min · Episode 38

    Scott Kirby, CEO of United Airlines, joins John and Ben Thompson to break down the airline business and United’s contrarian bets shaping commercial aviation. Scott details United’s massive COVID fleet expansion while…

  2. How Toto Wolff built the most valuable team in F1

    · 1 h 11 min · Episode 37

    Toto Wolff, Team Principal and Co-Owner of the Mercedes-AMG PETRONAS F1 Team, joins John Collison for a pint to discuss the engineering, management, and economics behind modern Formula 1. Toto breaks down how Mercedes…

  3. The company building underwater drones for $50,000

    · 50 min · Episode 36

    Will O'Brien, founder and CEO of Ulysses, joins John and Chris Sacca for a pint to discuss how underwater autonomous robots are scaling up to solve critical ocean challenges. They cover the technical history of…

  4. Muse Wonder: Zuckerberg and Wang's $100B AI

    · 2 h 14 min · Episode 35

    As Meta scales its AI infrastructure past five gigawatts, Mark Zuckerberg (founder and CEO, Meta) and Alexandr Wang (Chief AI Officer, Meta Superintelligence Labs) join John for a pint to discuss the launch of Muse…

  5. What comes after smartphones, with Snap CEO Evan Spiegel

    · 1 h 02 min · Episode 34

    Snap CEO Evan Spiegel joins John at the pub for a deep dive into Snap's "crucible moment" of 2026: the long-awaited consumer launch of Spectacles. Evan explains why he believes the smartphone has become an isolating…

  6. The economics and trends of the restaurant industry, with Tony Xu of DoorDash

    · 1 h 21 min · Episode 33

    Tony Xu, cofounder and CEO of DoorDash, joins John for a pint to discuss how they won a crowded market by obsessing over retention and the reality of fighting fraud in the physical world. They cover the harsh economics…

  7. The world of voice AI, with Mati Staniszewski of ElevenLabs

    · 1 h 00 min · Episode 32

    Mati Staniszewski is the co-founder of ElevenLabs, the research company making audio accessible across languages and voices. He sits down with John to discuss the "voice Turing Test" and why AI has conquered text but…

  8. The history and future of AI at Google, with Sundar Pichai

    · 1 h 09 min · Episode 31

    Sundar Pichai is the CEO of Google and Alphabet. He sits down with John and Elad Gil to discuss Google’s resurgence in the AI race, managing a massive $180 billion CapEx budget, and why 2026 is the year of the supply…

  9. Compliance at scale and why TAM is a distraction with Christina Cacioppo of Vanta

    · 57 min · Episode 30

    Christina Cacioppo, founder and CEO of Vanta, joins the pub to discuss building the future of agentic trust. She explains why compliance has a “vitamin vs painkiller” dynamic, the drama behind their famous…

  10. The 20-year journey to fully autonomous cars with Dmitri Dolgov of Waymo

    · 1 h 02 min · Episode 29

    Waymo is now doing nearly 500,000 rides a week across 10 cities. Co-CEO Dmitri Dolgov came to the pub to discuss how they moved from scientific research to massive global scaling. He gives a masterclass on the sensor…

  11. Creating prediction markets (and suing the CFTC) with Tarek Mansour and Luana Lopes Lara

    · 1 h 17 min · Episode 28

    Tarek Mansour and Luana Lopes Lara are the co-founders of Kalshi, the first federally regulated prediction market in the US. They sit down with John and Matt Huang to discuss growing their revenue 11x in six months,…

  12. Bret Taylor of Sierra on AI agents, outcome-based pricing, and the OpenAI board

    · 1 h 41 min · Episode 27

    Bret Taylor, co-founder of Sierra and Chair of the OpenAI board, joins John for a pint to discuss the rapid shift toward an agentic future. In this episode, Bret explains why outcome-based pricing is the future of…

  13. Garrett Langley of Flock Safety on building technology to solve crime

    · 1 h 44 min · Episode 26

    Garrett Langley is the founder and CEO of Flock Safety, a public safety operating system that helps communities and law enforcement eliminate crime. He sits down with John to discuss why most crime is opportunistic,…

  14. Reiner Pope of MatX on accelerating AI with transformer-optimized chips

    · 1 h 13 min · Episode 25

    Reiner Pope is the co-founder and CEO of MatX, designing specialized chips for Large Language Models. A former Google TPU architect, he joins John to discuss why the current generation of AI hardware is hitting a wall.…

  15. Stripe’s 2025 annual letter

    · 28 min · Episode 24

    The internet economy accelerated in 2025. The fastest-growing companies got even faster, agentic commerce and stablecoin payments started to kick into gear, and total payment volume on Stripe grew by a third as our…

  16. Ramp founder Eric Glyman on the many ways AI is changing corporate spending

    · 1 h 11 min · Episode 23

    Eric Glyman is the cofounder and CEO of Ramp, the finance automation platform that now powers over 2% of all corporate spend in the US. He sits down with John and co-host Alex Rampell to discuss how Ramp scaled to over…

  17. Ben Thompson from Stratechery on AI ads, the end of SaaS, and the future of media

    · 1 h 30 min · Episode 22

    Ben Thompson, the internet’s premier tech analyst, joins John for a wide-ranging conversation on the mechanics of the internet economy. They discuss the origins of Stratechery and the "1,000 true fans" model, why…

  18. Elon Musk on Space GPUs, AI, Optimus, and his manufacturing method

    · 2 h 46 min · Episode 21

    John Collison and Dwarkesh Patel sit down with Elon Musk to discuss why the future of AI isn’t on Earth, but in the "always sunny" vacuum of space. Between pints, they discuss the brutal physics of scaling—from the…

  19. Julia DeWahl of Antares on building nuclear reactors for the US military

    · 45 min · Episode 20

    Julia DeWahl is the cofounder of Antares, a company developing nuclear micro-reactors for the US military and critical infrastructure. She sits down with John to discuss the vision for the "Starlink of electricity",…

  20. Satya Nadella describes how lessons from Microsoft’s history apply to today’s boom

    · 1 h 19 min · Episode 19

    Satya Nadella, CEO of Microsoft, sits down with John to discuss the diffusion of AI inside the enterprise. He explains why “all your data at your fingertips” is the evergreen pitch, why this AI CapEx cycle is different…

  21. Dave Ricks, CEO of Eli Lilly, on GLP-1s and the business of pharma

    · 2 h 05 min · Episode 18

    Dave Ricks, the CEO of Eli Lilly, the world's most valuable pharmaceutical company, sits down with John and Patrick to discuss the complex business of drug development. Dave explains the true origin story of GLP-1s…

  22. Stablecoin special: Zach Abrams (Bridge) and Henri Stern (Privy)

    · 1 h 14 min · Episode 17

    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…

  23. Casey Handmer of Terraform Industries on solar maximalism, hard tech, and reclaiming the Salton Sea

    · 1 h 16 min · Episode 16

    Description Casey 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…

  24. Dan Sundheim of D1 Capital on the art of public market investing

    · 1 h 38 min · Episode 15

    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…

  25. How to build a $16B car company with RJ Scaringe, founder of Rivian

    · 1 h 09 min · Episode 14

    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…

  26. Tobi Lütke is still captivated by internet commerce, 20 years later

    · 1 h 43 min · Episode 13

    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…

  27. Marc Andreessen and Charlie Songhurst on the past, present, and future of Silicon Valley

    · 2 h 08 min · Episode 12

    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…

  28. Des Traynor on reinventing Intercom twice and the “four horsemen” of good AI companies

    · 1 h 18 min · Episode 11

    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…

  29. Ambrook CEO Mackenzie Burnett on American agriculture, rural resilience, and carrying 50lbs of fresh pork on Amtrak

    · 55 min · Episode 10

    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…

  30. Zipline CEO Keller Cliffton on air-dropping blood to Rwandan hospitals and getting to 50,000 aircraft per year

    · 1 h 14 min · Episode 9

    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.…

  31. Cognition CEO Scott Wu on acquiring Windsurf, AI replacing engineers, and the Moneyball-ification of everything

    · 58 min · Episode 8

    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…

  32. Coinbase CEO Brian Armstrong on bitcoin going to $1 million, electing a pro-crypto Congress, and Jamie Dimon

    · 1 h 17 min · Episode 7

    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…

  33. Robinhood CEO Vlad Tenev on tokenizing private companies, changing the SEC, and Frank Slootman

    · 1 h 06 min · Episode 6

    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…

  34. Anthropic CEO Dario Amodei on designing AGI-pilled products, model economics, and 19th-century vitalism

    · 1 h 03 min · Episode 5

    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…

  35. Serial entrepreneur Pieter Levels on building in public and living as a digital nomad

    · 23 min · Episode 4

    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…

  36. The Bot Company founder and CEO Kyle Vogt on home robots and why he’ll never sell another company

    · 23 min · Episode 3

    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…

  37. Meta CFO Susan Li on headcount vs. GPU allocation, “free cash flow” hats, and almost becoming a PM

    · 30 min · Episode 2

    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…

  38. OpenAI cofounder Greg Brockman on the scaling hypothesis and refactoring as a killer AI use case

    · 32 min · Episode 1

    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…

  39. Cheeky Pint hosted by Stripe cofounder John Collison

    · 0:56 · Trailer

    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…

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