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Cheeky Pint
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Cheeky Pint
Stripe
Stripe cofounder John Collison interviews founders, builders, and leaders over a pint.
Cheeky Pint
Stripe
Stripe cofounder John Collison interviews founders, builders, and leaders over a pint.
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Updated at Apr 07, 2026
Apr 07
The history and future of AI at Google, with Sundar Pichai
Sundar Pichai is the CEO of Google and Alphabet. He sits down with John and Elad Gil to discuss Google’s resurgence in the AI race, managing a massive $180 billion CapEx budget, and why 2026 is the year of the supply crunch. They cover the constraints of m...
1h 9m
Mar 31
Compliance at scale and why TAM is a distraction with Christina Cacioppo of Vanta
Christina Cacioppo, founder and CEO of Vanta, joins the pub to discuss building the future of agentic trust. She explains why compliance has a “vitamin vs painkiller” dynamic, the drama behind their famous 101-billboard campaign, and why she believes "mark...
57m
Mar 24
The 20-year journey to fully autonomous cars with Dmitri Dolgov of Waymo
Waymo is now doing nearly 500,000 rides a week across 10 cities. Co-CEO Dmitri Dolgov came to the pub to discuss how they moved from scientific research to massive global scaling. He gives a masterclass on the sensor stack (and why you still need Lidar), h...
1h 2m
Mar 17
Creating prediction markets (and suing the CFTC) with Tarek Mansour and Luana Lopes Lara
Tarek Mansour and Luana Lopes Lara are the co-founders of Kalshi, the first federally regulated prediction market in the US. They sit down with John and Matt Huang to discuss growing their revenue 11x in six months, why they sued their own regulator to lis...
1h 16m
Mar 10
Bret Taylor of Sierra on AI agents, outcome-based pricing, and the OpenAI board
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 belie...
1h 41m
Mar 05
Garrett Langley of Flock Safety on building technology to solve crime
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 c...
1h 44m
Feb 26
AI Ready
Reiner Pope of MatX on accelerating AI with transformer-optimized chips
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-o...
1h 13m
Feb 24
Stripe’s 2025 annual letter
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 annu...
27m
Feb 17
Ramp founder Eric Glyman on the many ways AI is changing corporate spending
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 y...
1h 11m
Feb 12
Ben Thompson from Stratechery on AI ads, the end of SaaS, and the future of media
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...
1h 30m
Feb 05
Elon Musk on Space GPUs, AI, Optimus, and his manufacturing method
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...
2h 46m
2025/11/25
Julia DeWahl of Antares on building nuclear reactors for the US military
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 nu...
45m
2025/11/18
AI Ready
Satya Nadella describes how lessons from Microsoft’s history apply to today’s boom
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 ...
1h 18m
2025/11/11
Dave Ricks, CEO of Eli Lilly, on GLP-1s and the business of pharma
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 pot...
2h 5m
2025/11/04
Stablecoin special: Zach Abrams (Bridge) and Henri Stern (Privy)
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 i...
1h 14m
2025/10/28
Casey Handmer of Terraform Industries on solar maximalism, hard tech, and reclaiming the Salton Sea
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 ano...
1h 16m
2025/10/22
Dan Sundheim of D1 Capital on the art of public market investing
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 succ...
1h 38m
2025/10/14
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...
1h 8m
2025/10/06
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 softwar...
1h 42m
2025/10/01
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 mista...
2h 7m
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