
Cheeky Pint
Stripe cofounder John Collison interviews founders, builders, and leaders over a pint.
Latest episodes

204 snips
Jul 9, 2025 • 23min
Serial entrepreneur Pieter Levels on building in public and living as a digital nomad
Pieter Levels, a serial entrepreneur and the mind behind Nomad List and Remote OK, shares his journey of building online businesses while living as a digital nomad. He discusses the challenges of monetizing digital content since a young age and contrasts indie hacking with traditional VC funding. Pieter reveals how he leverages automation tools like ChatGPT for efficiency and humorously reflects on the quirks of entrepreneurship in Europe, all while arguing for a more supportive environment for innovation. His insights are both practical and thought-provoking!

94 snips
Jun 25, 2025 • 23min
The Bot Company founder and CEO Kyle Vogt on home robots and why he’ll never sell another company
Kyle Vogt, founder and CEO of The Bot Company and cofounder of Twitch and Cruise, dives into the future of home robotics. He explains the differences between single-task and multi-task robots, emphasizing their potential to revolutionize everyday chores. Vogt reflects on the complexities of developing intelligent systems and navigating regulatory hurdles in self-driving tech. He also shares his regrets about selling Cruise and predicts that the next $100 billion company will be efficiently run by fewer than 100 people.

104 snips
Jun 18, 2025 • 30min
Meta CFO Susan Li on headcount vs. GPU allocation, “free cash flow” hats, and almost becoming a PM
Susan Li, the youngest CFO of a Fortune 100 company, shares her journey at Meta since 2008. She delves into the evolution of Mark Zuckerberg's leadership style and the culture of feedback at Meta. The conversation highlights the intricate balance of capital allocation between GPUs and headcount, as well as the humorous story behind "free cash flow" hats. Susan also discusses financial forecasting challenges and how AI is reshaping productivity, making room for more meaningful work in tech.

250 snips
Jun 18, 2025 • 32min
OpenAI cofounder Greg Brockman on the scaling hypothesis and refactoring as a killer AI use case
Greg Brockman, cofounder of OpenAI and Stripe's first engineer, shares his journey through AI's evolution alongside John Collison. They discuss OpenAI's unique approach to the scaling hypothesis and the pivotal lessons learned from deep learning adventures in Dota. Brockman reflects on a moment when he thought OpenAI was doomed and explores the future of AI in math and science. Key topics include energy bottlenecks, personalization, and the idea of refactoring as a groundbreaking AI use case. His insights reveal both excitement and caution for AI's potential.

Jun 16, 2025 • 56sec
Cheeky Pint hosted by Stripe cofounder John Collison
Join founders over a pint as they reminisce about the intersection of nostalgia and technology. Engaging anecdotes bring humor to their past educational experiences. They tackle the complexities of artificial intelligence, blending laughs with thought-provoking insights. From old photos to future tech predictions, it's a delightful mix of reflection and innovation.