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What comes after smartphones, with Snap CEO Evan Spiegel
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…
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 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…
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…
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…
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…
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…
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…
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…
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…
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…
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…
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…
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…
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…
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…
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…
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…
Casey Handmer of Terraform Industries on solar maximalism, hard tech, and reclaiming the Salton Sea
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…
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…
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Cheeky Pint has published 35 episodes since June 2025, covering topics in Business, Entrepreneurship.
Cheeky Pint is currently sporadic with new episodes weekly. Average episode length is 1h 9m.
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