Cheeky Pint – Details, episodes & analysis

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.

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

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?

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

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

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 sibling

(01:43) Building Anthropic with 7 cofounders

(02:52) ~$5 billion in ARR and vertical applications of products

(07:18) Developing a platform-first company

(10:08) Working with the DoD

(11:11) Proving skeptics wrong about revenue projections

(13:13) Capitalistic impulses of AI models

(15:43) AI market structure and players

(16:56) AI models as standalone P&Ls

(20:48) The data wall and styles of learning

(22:20) AI talent wars

(26:04) Pitching Anthropic’s API business to investors

(27:49) Cloud providers vs. AI labs

(29:05) AI customization and Claude for enterprise

(33:01) Dwarkesh’s take on limitations

(36:12) 19th-century notion of vitalism

(37:27) AI in medicine, customer service, and taxes

(40:59) How to solve for hallucinations

(42:41) The double-standard for AI mistakes

(44:14) Evolving from researcher to CEO

(46:59) Designing AGI-pilled products

(47:57) AI-native UIs

(50:09) Model progress and building products

(52:22) Open-source models

(54:43) Keeping Anthropic AGI-pilled

(57:11) AI advancements vs. safety regulations

(01:02:04) How Dario uses AI

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-his

Timestamps

(00:00) Intro

(00:58) Hyperinflation in Bulgaria

(04:07) Stablecoins 

(05:41) Home country bias in investing

(06:59) Robinhood’s origins

(11:23) What the book Flash Boys got wrong

(16:11) Options vs. equities

(17:38) Robinhood Gold

(19:34) Robinhood Banking 

(22:04) GameStop advice from Benioff, Zuck, and Elon

(26:40) Impact of retail investors on capital markets

(31:21) Where retail dollars are coming from

(32:10) The gamification narrative

(34:17) Tokenizing private companies

(41:57) Vlad makes his pitch to tokenize Stripe

(45:00) Prediction markets: tennis, the pope, and AI

(49:26) If Vlad ran the SEC

(51:15) How does Robinhood ship so fast?

(52:38) Remote work and Robinhood’s founder community 

(55:39) “What would Frank Slootman do?”

(57:32) Active traders

(59:46) Killing Robinhood’s cash card

(01:02:36) Harmonic and mathematical superintelligence

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-on-bitcoin

Timestamps

(00:00) Intro

(01:14) How Coinbase won the exchange market

(06:22) Losing money on every bitcoin purchase

(10:54) North Korean hackers

(14:54) The Everything Exchange

(17:39) Crypto will be bigger than gold

(19:22) Stablecoin adoption

(23:28) Jamie Dimon and big banks on crypto

(26:44) Coinbase as your primary financial account

(27:53) Neobanks

(29:41) Bitcoin going to $1 million

(33:16) Crypto in an investment portfolio

(34:43) GENIUS Act

(37:10) Electing a pro-crypto Congress

(45:24) Reforming accredited investor rules

(48:33) Squashing scams

(50:11) Bitcoin preserving the American experiment

(57:09) Balaji Srinivasan

(01:01:05) The mission-first company announcement

(01:05:50) How does Coinbase focus?

(01:07:44) Venture bets and Brian vetoing USDC

(01:12:02) Brian’s AI coding mandate

(01:15:13) Advice for Stripe

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

(04:10) Why drone delivery took so long

(07:38) Getting started in Rwanda

(13:31) 51% reduction in maternal mortality

(15:33) Access vs. waste

(21:45) Scaling globally

(24:05) Zipline’s Platform 1 

(25:50) The Right Stuff

(27:22) Drone design and safety

(30:12) Getting to 99.9% reliability

(34:39) Multimodal logistics

(38:15) Zipline’s Platform 2

(44:03) US drone regs and the FAA

(48:02) Progress and stagnation in US aviation

(51:30) If Keller ran the FAA

(54:24) 30% WoW growth in Texas

(58:25) Why Texas and not California?

(01:00:28) Building 50k drones in California

(01:06:18) US vs. Chinese manufacturing

(01:11:30) Advice for hardtech founders

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

Timestamps

(00:00) Intro

(01:13) Early life and maths competitions

(03:47) Addepar job as a high schooler

(05:43) Where are all the young founders?

(08:45) Moneyball-ification of everything

(11:42) Cognition’s AI software engineer, Devin

(15:46) Essential and accidental complexity

(17:59) How Devin works with enterprises

(19:48) IDE productivity

(21:56) Nihilist computer use argument 

(25:55) Benchmarking Devin 

(27:15) Market structure 

(30:32) Agent economy

(37:21) Cognition’s team of founders

(39:31) Jevons paradox and software 

(42:00) When will we see AI UIs?

(45:52) “I think we have AGI”

(47:03) Windsurf deal

(52:37) M&A in AI

(54:21) Cognition’s culture 

(55:48) Learning as a CEO

(57:12) Scott’s information diet