Cheeky Pint

Latest Episodes:

Serial entrepreneur Pieter Levels on building in public and living as a digital nomad Jul 09, 2025

Show notes

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 online as a 12 year old

(02:43) Being one of the first YouTube creators

(03:18) Who should indie hack

(04:31) What Pieter hates about VC-backed businesses

(07:51) Who is digital nomading for?

(09:15) Learning from @patio11

(10:17) 125k tweets and the brand of @levelsio

(10:59) Getting referrals from ChatGPT

(11:43) What Pieter automates with AI

(13:02) Investing and home country bias

(15:05) Hacking thermostats

(15:57) EU acceleration movement

(18:34) Entrepreneurship in the EU

(19:26) Pieter's reflections on Stripe’s API

(21:21) Looking 5 years into the future

The Bot Company founder and CEO Kyle Vogt on home robots and why he’ll never sell another company Jun 25, 2025

Show notes

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) 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 self-driving

(09:47) Viral demos and hype cycles

(10:38) Commercializing frontier tech

(13:06) Self-driving CapEx

(14:15) Regulatory hurdles

(16:18) Tesla vs. Waymo

(19:21) Why Kyle regrets selling Cruise

(21:39) The next $100 billion company

Meta CFO Susan Li on headcount vs. GPU allocation, “free cash flow” hats, and almost becoming a PM Jun 18, 2025

Show notes

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 leadership and culture of feedback

(09:06) Financial forecasting and capital allocation

(14:18) ROI on Meta’s portfolio of bets

(15:05) Investor sentiment in 2022

(17:49) The story behind the “free cash flow” hats

(18:58) CapEx trends in the AI era

(21:48) A memorable earnings call

(24:16) Challenges of allocating compute vs headcount budgets

(26:55) AI’s impact on productivity and operations

OpenAI cofounder Greg Brockman on the scaling hypothesis and refactoring as a killer AI use case Jun 18, 2025

Show notes

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 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) An early moment OpenAI felt doomed

(15:01) OS limits on AI product development

(17:59) When will AI make novel advancements in math or science?

(20:03) Energy bottlenecks

(22:30) S curves in AI advancement

(24:00) AI coding

(26:25) Refactoring as a killer AI use case

(27:26) How OpenAI decides what products to built

(28:53) Growing up in North Dakota

(30:17) How far away is AGI?

Cheeky Pint hosted by Stripe cofounder John Collison Jun 16, 2025

Show notes

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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