Cheeky Pint

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 (...

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...

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-o...

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://cheekyp...

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 si...

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 o...

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) Sin...

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 seriousl...

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 Mor...

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.