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Cheeky Pint
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Cheeky Pint
Stripe
Stripe cofounder John Collison interviews founders, builders, and leaders over a pint.
Cheeky Pint
Stripe
Stripe cofounder John Collison interviews founders, builders, and leaders over a pint.
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Updated at Nov 25, 2025
5 DAYS AGO
Julia DeWahl of Antares on building nuclear reactors for the US military
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", and why AI hyperscalers are driving a nu...
Nov 18
Satya Nadella describes how lessons from Microsoft’s history apply to today’s boom
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 from the .com bubble, and his vision ...
Nov 11
Dave Ricks, CEO of Eli Lilly, on GLP-1s and the business of pharma
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 (from Gila monster saliva), why their pot...
Nov 04
Stablecoin special: Zach Abrams (Bridge) and Henri Stern (Privy)
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 i...
Oct 28
Casey Handmer of Terraform Industries on solar maximalism, hard tech, and reclaiming the Salton Sea
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 he believes solar costs will drop ano...
Oct 22
Dan Sundheim of D1 Capital on the art of public market investing
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 succ...
Oct 14
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...
Oct 06
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 softwar...
Oct 01
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 mista...
Sep 24
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 ...
Sep 17
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 H...
Sep 10
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 referen...
Aug 27
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...
Aug 20
AI Ready
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 accou...
Aug 13
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 ap...
Aug 06
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 epis...
Jul 09
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...
Jun 25
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 ...
Jun 18
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: h...
Jun 18
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 ht...
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