Cheeky Pint
Episodes
Compliance at scale and why TAM is a distraction with Christina Cacioppo of Vanta
31 Mar 2026
Contributed by Lukas
Christina Cacioppo, founder and CEO of Vanta, joins the pub to discuss building the future of agentic trust. She explains why compliance has a “vita...
The 20-year journey to fully autonomous cars with Dmitri Dolgov of Waymo
24 Mar 2026
Contributed by Lukas
Waymo is now doing 500,000 rides a week across 11 cities. Co-CEO Dmitri Dolgov came to the pub to discuss how the team went from scientific research t...
Creating prediction markets (and suing the CFTC) with Tarek Mansour and Luana Lopes Lara
17 Mar 2026
Contributed by Lukas
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 a...
Bret Taylor of Sierra on AI agents, outcome-based pricing, and the OpenAI board
10 Mar 2026
Contributed by Lukas
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 ep...
Garrett Langley of Flock Safety on building technology to solve crime
05 Mar 2026
Contributed by Lukas
Garrett Langley is the founder and CEO of Flock Safety, a public safety operating system that helps communities and law enforcement eliminate crime. H...
Reiner Pope of MatX on accelerating AI with transformer-optimized chips
26 Feb 2026
Contributed by Lukas
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 ...
Stripe’s 2025 annual letter
24 Feb 2026
Contributed by Lukas
The internet economy accelerated in 2025. The fastest-growing companies got even faster, agentic commerce and stablecoin payments started to kick into...
Ramp founder Eric Glyman on the many ways AI is changing corporate spending
17 Feb 2026
Contributed by Lukas
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 w...
Ads as a societal good, the looming chip shortage, and the future of media, with Ben Thompson
12 Feb 2026
Contributed by Lukas
Ben Thompson, the internet’s premier tech analyst, joins John for a wide-ranging conversation on the mechanics of the internet economy. They discuss...
Elon Musk on Space GPUs, AI, Optimus, and his manufacturing method
05 Feb 2026
Contributed by Lukas
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. ...
Julia DeWahl of Antares on building nuclear reactors for the US military
25 Nov 2025
Contributed by Lukas
Julia DeWahl is the cofounder of Antares, a company developing nuclear micro-reactors for the US military and critical infrastructure. She sits down w...
Satya Nadella describes how lessons from Microsoft’s history apply to today’s boom
18 Nov 2025
Contributed by Lukas
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 fi...
Dave Ricks, CEO of Eli Lilly, on GLP-1s and the business of pharma
11 Nov 2025
Contributed by Lukas
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...
Stablecoin special: Zach Abrams (Bridge) and Henri Stern (Privy)
04 Nov 2025
Contributed by Lukas
Zach Abrams, the CEO and cofounder of Bridge, the leading stablecoin orchestration platform, and Henri Stern, CEO and cofounder of Privy, the leading ...
Casey Handmer of Terraform Industries on solar maximalism, hard tech, and reclaiming the Salton Sea
28 Oct 2025
Contributed by Lukas
DescriptionCasey Handmer is the founder of Terraform Industries, who is developing a machine that makes synthetic natural gas from sunlight and air. H...
Dan Sundheim of D1 Capital on the art of public market investing
22 Oct 2025
Contributed by Lukas
Seasoned public and private investor Dan Sundheim sits down with John to discuss the harrowing GameStop short squeeze, waking up at 3am for the Europe...
How to build a $16B car company with RJ Scaringe, founder of Rivian
14 Oct 2025
Contributed by Lukas
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, d...
Tobi LĂĽtke is still captivated by internet commerce, 20 years later
06 Oct 2025
Contributed by Lukas
Shopify founder and CEO Tobi Lütke joins John Collison to discuss the philosophies driving one of the internet’s most foundational companies. Tobi ...
Marc Andreessen and Charlie Songhurst on the past, present, and future of Silicon Valley
01 Oct 2025
Contributed by Lukas
Marc Andreessen, cofounder of Netscape and Andreessen Horowitz, sits down for a Cheeky Pint with John Collison and Charlie Songhurst to discuss the hi...
Des Traynor on reinventing Intercom twice and the “four horsemen” of good AI companies
24 Sep 2025
Contributed by Lukas
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 agen...
Ambrook CEO Mackenzie Burnett on American agriculture, rural resilience, and carrying 50lbs of fresh pork on Amtrak
17 Sep 2025
Contributed by Lukas
Mackenzie Burnett joins John Collison to talk about American agriculture, labor and immigration challenges, building rural resilience, ERPs, and the p...
Zipline CEO Keller Cliffton on air-dropping blood to Rwandan hospitals and getting to 50,000 aircraft per year
10 Sep 2025
Contributed by Lukas
Keller Cliffton joins John Collison to talk about Zipline’s journey to 115 million miles flown, the lost art of American airplanes, building 50k dro...
Cognition CEO Scott Wu on acquiring Windsurf, AI replacing engineers, and the Moneyball-ification of everything
27 Aug 2025
Contributed by Lukas
Scott Wu joins John Collison to talk about Cognition’s AI software engineer, the Moneyball-ification of everything, math competitions with Alexandr ...
Coinbase CEO Brian Armstrong on bitcoin going to $1 million, electing a pro-crypto Congress, and Jamie Dimon
20 Aug 2025
Contributed by Lukas
Brian Armstrong joins John Collison to talk about what’s happening behind the scenes at Coinbase: battling North Korean hackers, war stories from ea...
Robinhood CEO Vlad Tenev on tokenizing private companies, changing the SEC, and Frank Slootman
13 Aug 2025
Contributed by Lukas
Vlad Tenev joins John Collison to discuss Bulgarian hyperinflation, Robinhood Banking, details from the GameStop saga—including advice from Marc Ben...
Anthropic CEO Dario Amodei on designing AGI-pilled products, model economics, and 19th-century vitalism
06 Aug 2025
Contributed by Lukas
Dario Amodei joins John Collison to talk about Anthropic's growth to ~$5 billion in ARR, how AI models show capitalistic impulses, predictions for an ...
Serial entrepreneur Pieter Levels on building in public and living as a digital nomad
09 Jul 2025
Contributed by Lukas
Pieter Levels joins John Collison to discuss building successful online businesses as a digital nomad, thoughts on European accelerationism, and Piete...
The Bot Company founder and CEO Kyle Vogt on home robots and why he’ll never sell another company
25 Jun 2025
Contributed by Lukas
The Bot Company founder and CEO Kyle Vogt—who also cofounded Twitch and Cruise—joins John Collison to talk about applying AI to home robots, the s...
OpenAI cofounder Greg Brockman on the scaling hypothesis and refactoring as a killer AI use case
18 Jun 2025
Contributed by Lukas
Greg Brockman—OpenAI cofounder and Stripe's first engineer—joins John Collison to talk about research-driven product development, an early moment ...
Meta CFO Susan Li on headcount vs. GPU allocation, “free cash flow” hats, and almost becoming a PM
18 Jun 2025
Contributed by Lukas
Susan Li of Meta—the youngest chief financial officer of a Fortune 100 company—joins John Collison to talk about capital allocation, managing inve...
Cheeky Pint hosted by Stripe cofounder John Collison
16 Jun 2025
Contributed by Lukas
John sits down with founders and builders over a pint—Greg Brockman (cofounder of OpenAI), Susan Li (chief financial officer at Meta), Kyle Vogt (fo...