Cheeky Pint

Julia DeWahl is the cofounder of Antares, a company developing nuclear micro-reactors for the US military and critical infrastructure. She sits down with John to discuss the vision for the "Starlink of electricity", and why AI hyperscalers are driving a nuclear renaissance. They cover the bipartisan shift in nuclear regulation (and why the NRC’s old mandate made "zero" the safest number of reactors), and why true energy resilience requires more than just solar and batteries. Julia also shares lessons from the early days of Opendoor and Starlink, including why customer obsession sometimes means sitting outside a bagel shop.

Satya Nadella, CEO of Microsoft, sits down with John to discuss the diffusion of AI inside the enterprise. He explains why “all your data at your fingertips” is the evergreen pitch, why this AI CapEx cycle is different from the .com bubble, and his vision for "agentic commerce". They also cover Microsoft's product bundling strategy and how he "wanders the virtual corridors" of Teams to run the company.

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Dave Ricks, the CEO of Eli Lilly, the world's most valuable pharmaceutical company, sits down with John and Patrick to discuss the complex business of drug development. Dave explains the true origin story of GLP-1s (from Gila monster saliva), why their potential goes far beyond weight loss to addiction and inflammation, and how "self-pay" has become the #1 way new patients get Zepbound. They cover the "shadow generic" industry undermining patents, the challenges associated with clinical trial enrollment, and what drove insulin list prices to $275 (while the net price was $40). This is a rare, candid look into the strategies...

Zach Abrams, the CEO and cofounder of Bridge, the leading stablecoin orchestration platform, and Henri Stern, CEO and cofounder of Privy, the leading crypto wallet infrastructure, sit down with John to discuss the future of stablecoins, issuing, and what it will take for crypto to become ubiquitous. Both companies recently joined Stripe, and are uniquely positioned to dissect how crypto is changing financial infrastructure.

Key moments

(00:00) Introducing Bridge + Privy

(06:39) How stablecoins are being used today

(14:27) US Dollar dominance

(25:50) The future of banking

(34:35) Blockchains

(42:27) Building a...

Description

Casey Handmer is the founder of Terraform Industries, who is developing a machine that makes synthetic natural gas from sunlight and air. He joins the podcast to explain his solar maximalist worldview, why he believes solar costs will drop another 10x, and the core physics that doomed Hyperloop from the start. They also discuss the lessons of the underappreciated industrialist Henry Kaiser, Casey's new venture in solar-powered desalination, his grand plan to refill the Salton Sea, and why he believes "hard-edged" leaders are essential for hardware success.

Show notes

Seasoned public and private investor Dan Sundheim sits down with John to discuss the harrowing GameStop short squeeze, waking up at 3am for the European market open, and the emotional asymmetry of managing billions of dollars. They cover why he thinks successful private companies should avoid the public markets, the real genius of Elon Musk's business approach, and the pattern recognition that comes from years of investing. This is a rare, candid look into the strategies and mindset of a top public markets investor.

Show notes

RJ Scaringe, founder and CEO of Rivian, sits down for a cheeky pint with John Collison to discuss what it takes to build a car company from scratch, developing the first electric pickup truck, the shift to a software-defined zonal architecture, Rivian's AI-driven approach to autonomy, and the strategy behind their recent $5.8 billion deal with Volkswagen.

Timestamps
(00:00) Gen 1

(12:32) Gen 2

(18:37) Developing the first electric pickup truck

(27:36) John pitches some car features

(36:46) Stripe’s payment methods

(37:54) Autonomous driving

(44:51) Component progress

(53:17) The new economics of ca...

Shopify founder and CEO Tobi Lütke joins John Collison to discuss the philosophies driving one of the internet’s most foundational companies. Tobi shares his perspective on why companies are a form of technology, how internal tools and "opinionated software" shape an organization's culture and accelerate its evolution, and why the best gift is finding a beautiful, unsolvable problem.

Show notes

Marc Andreessen, cofounder of Netscape and Andreessen Horowitz, sits down for a Cheeky Pint with John Collison and Charlie Songhurst to discuss the history of Silicon Valley, spotting bubbles in real time, the "Elon method" of management, and why the mistakes that haunt you are the companies you don't invest in.

Show notes:

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-intercom

Timestamps: 

(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 users

(44:14) Usage-based billing

(45:14) Advice for startups

(52:09) AI pricing

(01:07:27) Cofounder dyn...

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:

Full transcript on Substack: https://cheekypint.substack.com/p/ambrook-ceo-mackenzie-burnett-on 

Timestamps:
(00:00) Introducing Ambrook

(05:37) Serving farmers

(19:25) Building rural resilience

(21:49) The economics of ag

(28:03) If Mackenzie ran the...

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:

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) Sca...

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

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 Everyt...

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 th...

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...

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 digi...

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...

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...

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 ...

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.