PODCAST

Cheeky Pint

Stripe

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

technology entrepreneurship

All Episodes

78:20

Des Traynor on reinventing Intercom twice and the...

Cheeky Pint ·

2025/09/24

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

54:53

Ambrook CEO Mackenzie Burnett on American...

Cheeky Pint ·

2025/09/17

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)

74:12

Zipline CEO Keller Cliffton on air-dropping blood to...

Cheeky Pint ·

2025/09/10

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

57:53

Cognition CEO Scott Wu on acquiring Windsurf, AI...

Cheeky Pint ·

2025/08/27

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

76:35

Coinbase CEO Brian Armstrong on bitcoin going to $1...

Cheeky Pint ·

2025/08/20

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

65:50

Robinhood CEO Vlad Tenev on tokenizing private...

Cheeky Pint ·

2025/08/13

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)

62:51

Anthropic CEO Dario Amodei on designing AGI-pilled...

Cheeky Pint ·

2025/08/06

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

22:37

Serial entrepreneur Pieter Levels on building in...

Cheeky Pint ·

2025/07/09

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.Timestamps00:00 Intro00:37 Pieter’s resume01:33 Trying to make money online as a 12 year old02:43 Being one of the first YouTube creators03:18 Who should indie hack04:31 What Pieter hates about VC-backed businesses07:51 Who is digital nomading

22:31

The Bot Company founder and CEO Kyle Vogt on home...

Cheeky Pint ·

2025/06/25

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.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

31:51

OpenAI cofounder Greg Brockman on the scaling...

Cheeky Pint ·

2025/06/18

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.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)

29:43

Meta CFO Susan Li on headcount vs. GPU allocation,...

Cheeky Pint ·

2025/06/18

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.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

0:56

Cheeky Pint hosted by Stripe cofounder John Collison

Cheeky Pint ·

2025/06/16

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.

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Cheeky Pint

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