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
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
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.
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
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:
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) What is cheeky? Why a pint?
(04:30) Bubbles
(14:55) Do VCs matter?
(19:01) The history of Silicon Valley
(32:25) The parable of Digital Research Inc.
(39:02) The internet; a bear case
(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 Collision 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 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:
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
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.
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—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.
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
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.
Timestamps
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.
Timestamps:
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?
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.
