Stripe's Cheeky Pint
Stripe's Cheeky Pint episodes converted into bullet points.
Episodes
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What comes after smartphones, with Evan Spiegel of Snap
Snap CEO Evan Spiegel joins John at the pub for a deep dive into Snap's "crucible moment" of 2026: the long-awaited consumer launch of Spectacles. Evan explains why he believes the smartphone has become an isolating legacy device and how true AR glasses represent the first step toward making comp...
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The economics and trends of the restaurant industry, with Tony Xu of DoorDash
Tony Xu, cofounder and CEO of DoorDash, joins John for a pint to discuss how they won a crowded market by obsessing over retention and the reality of fighting fraud in the physical world. They cover the harsh economics of the restaurant industry, why DoorDash succeeded where Google failed, and th...
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The world of voice AI, with Mati Staniszewski of ElevenLabs
Mati Staniszewski is the co-founder of ElevenLabs, the research company making audio accessible across languages and voices. He sits down with John to discuss the "voice Turing Test" and why AI has conquered text but still struggles with conversational speech. They discuss the future of human-com...
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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 memory and power, why he believes the US e...
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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 "market sizing is bullshit." They cover the te...
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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), how they use "Simulation" and "Critic" mod...
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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 list election markets, and how they are buil...
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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 believes the atomic unit of AI productivity is...
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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 crimes a year, and the engineering challen...
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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-off" between latency and throughput for cu...
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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.
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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 years, and why the future of fintech is "s...
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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 (and the best Uber Eats market), and why...
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Elon Musk – "In 36 months, the cheapest place to put AI will be space”
In this episode, John and I got to do a real deep-dive with Elon. We discuss the economics of orbital data centers, the difficulties of scaling power on Earth, what it would take to manufacture humanoids at high-volume in America, xAI’s business and alignment plans, DOGE, and much more.