Cheeky Pint

Stripe
  • 4.9 (34)
  • TECHNOLOGY

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

  1. How to build a $16B car company with RJ Scaringe, founder of Rivian

    2D AGO

    How to build a $16B car company with RJ Scaringe, founder of Rivian

    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

    1h 9m
  2. Tobi Lütke is still captivated by internet commerce, 20 years later

    OCT 6

    Tobi Lütke is still captivated by internet commerce, 20 years later

    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

    1h 43m
  3. Marc Andreessen and Charlie Songhurst on the past, present, and future of Silicon Valley

    OCT 1

    Marc Andreessen and Charlie Songhurst on the past, present, and future of Silicon Valley

    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) 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

    2h 8m
  4. Des Traynor on reinventing Intercom twice and the “four horsemen” of good AI companies

    SEP 24

    Des Traynor on reinventing Intercom twice and the “four horsemen” of good AI companies

    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?

    1h 18m
  5. Ambrook CEO Mackenzie Burnett on American agriculture, rural resilience, and carrying 50lbs of fresh pork on Amtrak

    SEP 17

    Ambrook CEO Mackenzie Burnett on American agriculture, rural resilience, and carrying 50lbs of fresh pork on Amtrak

    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

    55 min
  6. Zipline CEO Keller Cliffton on air-dropping blood to Rwandan hospitals and getting to 50,000 aircraft per year

    SEP 10

    Zipline CEO Keller Cliffton on air-dropping blood to Rwandan hospitals and getting to 50,000 aircraft per year

    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

    1h 14m
  7. Cognition CEO Scott Wu on acquiring Windsurf, AI replacing engineers, and the Moneyball-ification of everything

    AUG 27

    Cognition CEO Scott Wu on acquiring Windsurf, AI replacing engineers, and the Moneyball-ification of everything

    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

    58 min
  8. Coinbase CEO Brian Armstrong on bitcoin going to $1 million, electing a pro-crypto Congress, and Jamie Dimon

    AUG 20

    Coinbase CEO Brian Armstrong on bitcoin going to $1 million, electing a pro-crypto Congress, and Jamie Dimon

    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

    1h 17m
See All (15)

Trailer

4.9
out of 5
34 Ratings

About

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

Information

  • Creator
    Stripe
  • Years Active
    2K
  • Episodes
    15
  • Rating
    Clean
  • Copyright
    © 2025 Stripe

You Might Also Like