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Cheeky Pint

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Rating
★★★★★
4.9
from
48 reviews
This podcast has
22 episodes
Language
English
Publisher
Stripe
Explicit
No
Date created
2025/06/16
Latest episode
2026/02/05
Average duration
88 min.
Release period
13 days

Description

Stripe cofounder John Collison interviews founders, builders, and leaders over a pint.

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Elon Musk on Space GPUs, AI, Optimus, and his manufacturing method
2026/02/05
John Collison and Dwarkesh Patel sit down with Elon Musk to discuss why the future of AI isn’t on Earth, but in the "always sunny" vacuum of space. Between pints, they discuss the brutal physics of scaling—from the "farcically cheap" solar cells coming out of China to switching Starship from carbon fiber to stainless steel—as well as the “infinite money glitch” of humanoid robots, China, and DOGE. Timestamps 00:00:23 Space GPUs 00:35:39 Alignment 00:58:48 xAI 01:15:01 Optimus 01:28:03 China 01:40:46 Management 02:16:38 DOGE 02:34:58 Space GPUs redux
Julia DeWahl of Antares on building nuclear reactors for the US military
2025/11/25
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. Timestamps(00:00) Lessons from SpaceX and Opendoor (02:46) Introducing Antares (06:30) The path to market (12:20) Nuclear vibe shift (15:11) Regulation (19:21) Possible energy futures (24:02) Stripe Radar (24:55) Nuclear supply chains (26:43) Antares origin story (30:24) Funding Antares (36:09) If Julia was energy tsar (42:33) Restarting shuttered plants
Satya Nadella describes how lessons from Microsoft’s history apply to today’s boom
2025/11/18
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. Links [Read] Softwar: An Intimate Portrait of Larry Ellison and Oracle, Matthew Symonds[Try] Superwhisper[Read] The Internet Tidal Wave, Bill Gates Timestamps (00:00) AI adoption in the enterprise(07:47) How Satya runs Microsoft (13:45) New UIs (20:44) Microsoft tackling the early internet (25:58) Are we in a bubble? (31:35) Data sovereignty (38:10) Excel (42:01) Agentic commerce (52:45) AI brand loyalty (59:44) Product bundling (01:08:18) Microsoft’s culture (01:12:12) The law of very large companies (01:16:20) What’s in the water in Hyderabad?
Dave Ricks, CEO of Eli Lilly, on GLP-1s and the business of pharma
2025/11/11
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, science, and future of pharma from one of the industry's most influential leaders. Timestamps (00:00) Introducing Dave Ricks (05:07) Making R&D decisions (10:10) Clinical trials (24:59) Drug pricing (32:43) Stimulating more R&D (54:15) Pros and cons of US healthcare (58:20) New pharma business models (01:05:53) Stripe and enterprises (01:07:00) China (01:16:31) Generics (01:22:37) GLP-1s (1:37:43) r/Peptides (01:41:25) LillyDirect (01:46:35) Why do investors love LLY?
Stablecoin special: Zach Abrams (Bridge) and Henri Stern (Privy)
2025/11/04
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
Casey Handmer of Terraform Industries on solar maximalism, hard tech, and reclaiming the Salton Sea
2025/10/28
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 ComingKey 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
Dan Sundheim of D1 Capital on the art of public market investing
2025/10/22
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
How to build a $16B car company with RJ Scaringe, founder of Rivian
2025/10/14
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
Tobi Lütke is still captivated by internet commerce, 20 years later
2025/10/06
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 CowboyKey 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 and Charlie Songhurst on the past, present, and future of Silicon Valley
2025/10/01
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 ManagementDavid Swensen: Pioneering Portfolio ManagementIan M Banks: Consider Phlebas: A Culture NovelWalter Isaacson: Elon MuskThomas Rid: Rise of the Machines: A Cybernetic HistoryGeorge McGovern: A Politician's Dream Is a Businessman's Nightmare, WSJSteve Blank: The Secret History of Silicon ValleyTracy Kidder: The Soul of a New MachineJohn Perry Barlow: A Declaration of the Independence of CyberspaceMartin Gurri: Revolt of the PublicJohn Malone: Born to Be WiredFull 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 on reinventing Intercom twice and the “four horsemen” of good AI companies
2025/09/24
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?
Ambrook CEO Mackenzie Burnett on American agriculture, rural resilience, and carrying 50lbs of fresh pork on Amtrak
2025/09/17
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 MentionedFarming goes digitalThe 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
Zipline CEO Keller Cliffton on air-dropping blood to Rwandan hospitals and getting to 50,000 aircraft per year
2025/09/10
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 WolfeSkunk Works by Ben RichApple 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
Cognition CEO Scott Wu on acquiring Windsurf, AI replacing engineers, and the Moneyball-ification of everything
2025/08/27
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
Coinbase CEO Brian Armstrong on bitcoin going to $1 million, electing a pro-crypto Congress, and Jamie Dimon
2025/08/20
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

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4.9 out of 5
48 reviews
★★★★★
edwinarbus 2025/11/29
Host is very smart
He should start a payments company or something; seems very knowledgeable
★★★★★
Avid pod listener7 2025/09/13
Longer is better
Great show
★☆☆☆☆
Anonymous college kid 2025/09/25
Please change this
I love this show, but the transition sound to commercial sounds just like the Doppler effect of a car horn speeding towards you. It gives me a heart a...
★★★★★
ZachTXM 2025/06/20
Love it!
I love how they keep the episodes reasonable short instead of like an hour. Guests have been great so far. Gotta finish your beer though
check all reviews on apple podcasts

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