PODCAST

Cheeky Pint

Stripe

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

technology entrepreneurship

All Episodes

101:23

Bret Taylor of Sierra on AI agents, outcome-based...

Cheeky Pint ·

2026/03/10

Bret Taylor, co-founder of Sierra and Chair of the OpenAI board, joins John for a pint to discuss the rapid shift toward an agentic future. In this episode, Bret explains why outcome-based pricing is the future of software business models, and why he believes the atomic unit of AI productivity is a process, not a person. They cover why big companies struggle to adopt AI because they are “shipping their org charts.” Bret also discusses a new type of hyper-generalist, reflects on his

104:15

Garrett Langley of Flock Safety on building...

Cheeky Pint ·

2026/03/05

Garrett Langley is the founder and CEO of Flock Safety, a public safety operating system that helps communities and law enforcement eliminate crime. He sits down with John to discuss why most crime is opportunistic, how Flock helps clear over one million crimes a year, and the engineering challenges of building solar-powered cameras and autonomous drones. They cover the shifting landscape of criminal technology, why hardware requires making "one-way door" decisions, and his vision for a

73:07

Reiner Pope of MatX on accelerating AI with...

Cheeky Pint ·

2026/02/26

Reiner Pope is the co-founder and CEO of MatX, designing specialized chips for Large Language Models. A former Google TPU architect, he joins John to discuss why the current generation of AI hardware is hitting a wall. They cover the "uncomfortable trade-off" between latency and throughput for current chips, why MatX is betting on combining HBM and SRAM to solve it, and the massive logistical challenge of manufacturing chips at scale with TSMC. Reiner also shares his predictions for AI in

27:44

Stripe’s 2025 annual letter

Cheeky Pint ·

2026/02/24

The internet economy accelerated in 2025. The fastest-growing companies got even faster, agentic commerce and stablecoin payments started to kick into gear, and total payment volume on Stripe grew by a third as our customers continued to prosper.Our annual letter covers the trends that we think are worth paying close attention to as the pace of change accelerates.Timestamps(01:48) The sorting machine(05:45) Global by default(09:01) Stable progress(12:14) Working capital’s working

71:18

Ramp founder Eric Glyman on the many ways AI is...

Cheeky Pint ·

2026/02/17

Eric Glyman is the cofounder and CEO of Ramp, the finance automation platform that now powers over 2% of all corporate spend in the US. He sits down with John and co-host Alex Rampell to discuss how Ramp scaled to over $1 billion in revenue in just seven years, and why the future of fintech is "selling time, not money." They cover the "SaaS apocalypse" (and why lines of code are becoming a liability), how Ramp uses AI agents to review 100,000 expenses a day with 99% accuracy, and why their

90:15

Ben Thompson from Stratechery on AI ads, the end of...

Cheeky Pint ·

2026/02/12

Ben Thompson, the internet’s premier tech analyst, joins John for a wide-ranging conversation on the mechanics of the internet economy. They discuss the origins of Stratechery and the "1,000 true fans" model, why Taiwan is the most convenient place to live (and the best Uber Eats market), and why the public markets are wrong to think SaaS is "canceled." Ben also explains why the US failure to control the TikTok algorithm is a disaster, why he’s a "crypto defender" in an age of infinite AI

166:02

Elon Musk on Space GPUs, AI, Optimus, and his...

Cheeky Pint ·

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.Timestamps00:00:23 Space GPUs00:35:39 Alignment00:58:48 xAI01:15:01 Optimus01:28:03

45:17

Julia DeWahl of Antares on building nuclear reactors...

Cheeky Pint ·

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

78:51

Satya Nadella describes how lessons from Microsoft’s...

Cheeky Pint ·

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

125:15

Dave Ricks, CEO of Eli Lilly, on GLP-1s and the...

Cheeky Pint ·

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

74:09

Stablecoin special: Zach Abrams (Bridge) and Henri...

Cheeky Pint ·

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

76:07

Casey Handmer of Terraform Industries on solar...

Cheeky Pint ·

2025/10/28

DescriptionCasey 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

98:08

Dan Sundheim of D1 Capital on the art of public...

Cheeky Pint ·

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

68:48

How to build a $16B car company with RJ Scaringe,...

Cheeky Pint ·

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)

102:55

Tobi Lütke is still captivated by internet commerce,...

Cheeky Pint ·

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:

127:56

Marc Andreessen and Charlie Songhurst on the past,...

Cheeky Pint ·

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

78:20

Des Traynor on reinventing Intercom twice and the...

Cheeky Pint ·

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-intercomTimestamps: (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

54:53

Ambrook CEO Mackenzie Burnett on American...

Cheeky Pint ·

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)

74:12

Zipline CEO Keller Cliffton on air-dropping blood to...

Cheeky Pint ·

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 McGeeTimestamps(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

57:53

Cognition CEO Scott Wu on acquiring Windsurf, AI...

Cheeky Pint ·

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-acquiringTimestamps(00:00) Intro(01:13) Early life and maths competitions(03:47) Addepar job as a high

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