Cheeky Pint

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 cars

(01:01:11) Manufacturing in the US

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

• [Buy] Momax: 140W Universal Travel Adapter
• [Read] Benjamin Bloom: The 2 Sigma Problem
• [Buy] Ikigai: vitamin cases 
• [Read] Kevin Kelly: 1,000 True Fans
• [Read] Erich Gamma: Design Patterns 
• [Read] Charles Calomiris: Fragile by Design
• [Listen] Business Breakdowns: Formula One
• [Watch] Netflix: Formula 1: Drive to Survive
• [Read] Mark Robichaux: Cable Cowboy

Key Moments

(00:00) Intro

(07:07) How internal software shapes culture

(16:32) The Shopify vision

(27:49) Peak transaction capacity

(34:36) Agentic commerce

(49:15) Shop Pay

(55:29) Stablecoins

(59:20) Stripe + Shopify

(1:12:23) Learning from the Coinbase board

(1:17:23) Is Tobi ungovernable?

(1:25:02) Entrepreneurship

(1:31:50) Advice for Mark Carney

(1:36:40) Motor racing

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:

• Roger Lowenstein: When Genius Failed: The Rise and Fall of Long-Term Capital Management
• David Swensen: Pioneering Portfolio Management
• Ian M Banks: Consider Phlebas: A Culture Novel
• Walter Isaacson: Elon Musk
• Thomas Rid: Rise of the Machines: A Cybernetic History
• George McGovern: A Politician's Dream Is a Businessman's Nightmare, WSJ
• Steve Blank: The Secret History of Silicon Valley
• Tracy Kidder: The Soul of a New Machine
• John Perry Barlow: A Declaration of the Independence of Cyberspace
• Martin Gurri: Revolt of the Public
• John Malone: Born to Be Wired

Full transcript on Substack: https://cheekypint.substack.com/p/marc-andreessen-and-charlie-songhurst 

Subscribe to Cheeky Pint

Spotify: https://open.spotify.com/show/2IHbGJJMpiFoz5YrvRfTFw

Apple Podcasts: https://podcasts.apple.com/us/podcast/cheeky-pint/id1821055332

Substack: https://cheekypint.substack.com/

Key moments

(00:00) Marc needs to know: what is a cheeky pint?

(04:30) Are we in a bubble?

(14:55) Do VCs matter?

(19:01) The history of Silicon Valley

(32:25) How Digital Research almost made it

(39:02) A bear case on the internet

(59:52) AI productivity

(01:12:10) Stripe + AI

(01:13:08) Crypto

(01:24:08) Should a16z start a hedge fund?

(01:29:51) Big companies

(01:35:33) Boards

(01:40:27) The Elon method

(01:52:59) The future of media

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 dynamics

(01:11:04) Predictors of company success

(01:15:56) How AI-native is Intercom?

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:

• Where Soil is Holy, and Climate Change Is Seldom Mentioned
• Farming goes digital
• The End of Accounting and the Path Forward for Investors and Managers 

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 USDA

(30:53) Vertical SaaS

(34:49) The wonders of accounting

(38:41) Ambrook-as-fintech

(44:00) If Mackenzie ran Stripe

(50:53) Joshua Kushner and Dylan Field

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

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

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

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