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 modular stack

(47:14) Open issuance

(56:55) M&A

(01:11:02) The future of stablecoins

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

• [Read] Ashlee Vance: Elon Musk    
• [Read] Francis Spufford: Red plenty
• [Listen] Beneath the Surface, Episode 2 : Salton Sea 
• [Read] Marc Reisner: Cadillac Desert
• [Read] Albert P. Heiner: Henry J. Kaiser
• [Read] Mark S. Foster: Henry Kaiser
• [Read] Ernest K. Gann: Fate is the Hunter
• [Read] Captain W. E. Johns: Biggles: The Camels are Coming

Key moments

(00:00) Intro

(02:28) Henry Kaiser

(08:49) Introducing Terraform

(13:08) Where electricity won’t work

(16:50) The solar maximalist perspective

(22:57) Terraformer Mark One

(27:49) The role of intervention

(37:30) American dynamism

(47:36) The Origins of Efficiency, by Brian Potter

(48:33) Children and education

(37:30) American dynamism

(55:15) Desalination

(01:08:16) Lessons from leadership

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

• [Read] The Essays of Warren Buffett: Lessons for Corporate America by Lawrence A. Cunningham
• [Read] The Buffett Partnership Letters (1957-1970)
• [Read] Value Investors Club (VIC)

Timestamps

(00:00) The D1 operating model

(07:54) Getting it wrong on NFLX

(11:44) What makes a good stock picker

(18:16) Portfolio-building

(24:35) GameStop

(35:57) The art of short-selling

(41:48) How to spot a turnaround

(47:12) Waking up at 3 AM

(53:14) Money management

(59:31) Dan’s 10-year hands-off stock pick

(01:09:52) China

(01:14:44) Are we in a bubble?

(01:20:41) SpaceX

(01:25:04) Investing in private companies

(01:32:55) Thoughts on the banking industry

(01:35:58) Advice for budding investors

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