Cheeky Pint

Stripe

Technology

Business

Entrepreneurship

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

Last refreshed: April 28th, 2026 at 10:11 AM ⓘ

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Episodes

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

In this episode, serial entrepreneur Pieter Levels shares his unique journey building multiple successful online businesses as a digital nomad, making over $3 million annually without VC funding. He delves into his philosophy of "indie hacking," his use of AI for business automation and community moderation, and his insights on personal investment strategies. Levels also discusses the European accelerationism movement, highlighting the regulatory burdens and cultural attitudes impacting entrepreneurship in Europe, and offers his reflections on Stripe's API.

Jul 09, 2025•23 min•Ep. 4

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

Kyle Vogt, a serial entrepreneur, shares his vision for The Bot Company, aiming to bring adaptable, multi-task home robots into every home, enabled by recent advancements in AI and neural networks. He draws parallels between the “last mile” challenges in home robotics and self-driving cars, highlighting the distinct approaches of Tesla and Waymo. Vogt also reflects on his experience selling Cruise, emphasizing the drawbacks of large company structures and advocating for small, in-person teams to build the next generation of $100 billion companies.

Jun 25, 2025•23 min•Ep. 3

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 lead...

Jun 18, 2025•30 min•Ep. 2

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

OpenAI cofounder Greg Brockman discusses the scaling hypothesis that propelled OpenAI's success, drawing lessons from the Dota 2 project. The conversation explores the rapid advancements in deep learning, the importance of personalization in AI, and OpenAI's unique research-driven product development strategy. They also cover AI's transformative applications in fields like medicine and coding, potential bottlenecks in energy and data, and Brockman's reflections on the consistently surprising and beneficial nature of AI's evolution and AGI predictions.

Jun 18, 2025•32 min•Ep. 1

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.

Jun 16, 2025•56 sec

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