Cheeky Pint

What comes after smartphones, with Snap CEO Evan Spiegel Apr 27, 2026 3746 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 computing human again. They discuss the technical hurdles of fitting a spatial computer into a gla

The economics and trends of the restaurant industry, with Tony Xu of DoorDash Apr 21, 2026 4856 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 the harrowing story of spending 40% of their remaining cash on refunds to save the company’s rep

The world of voice AI, with Mati Staniszewski of ElevenLabs Apr 14, 2026 3622 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-computer interaction, including why we still can't get our phones to read a PDF properly and the

The history and future of AI at Google, with Sundar Pichai Apr 7, 2026 4163 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 economy will grow significantly due to AI, and the internal cultural shift back to "Googley" op

Compliance at scale and why TAM is a distraction with Christina Cacioppo of Vanta Mar 31, 2026 3447 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 tension between vibe coding and rigorous security, how Vanta is using agents to generate UI, and

The 20-year journey to fully autonomous cars with Dmitri Dolgov of Waymo Mar 24, 2026 3740 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" models to train the AI, and why he believes cars that require human supervision will never natura

Creating prediction markets (and suing the CFTC) with Tarek Mansour and Luana Lopes Lara Mar 17, 2026 4590 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 building the "New York Stock Exchange of events." They cover why prediction markets are an antidot

Bret Taylor of Sierra on AI agents, outcome-based pricing, and the OpenAI board Mar 10, 2026 6083 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 “

Garrett Langley of Flock Safety on building technology to solve crime Mar 5, 2026 6255 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

Reiner Pope of MatX on accelerating AI with transformer-optimized chips Feb 26, 2026 4387 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 logist

Stripe’s 2025 annual letter Feb 24, 2026 1664 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 sor

Ramp founder Eric Glyman on the many ways AI is changing corporate spending Feb 17, 2026 4270 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

Ben Thompson from Stratechery on AI ads, the end of SaaS, and the future of media Feb 12, 2026 5415 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 failur

Elon Musk on Space GPUs, AI, Optimus, and his manufacturing method Feb 5, 2026 9962 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,

Julia DeWahl of Antares on building nuclear reactors for the US military Nov 25, 2025 2717 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 o

Satya Nadella describes how lessons from Microsoft’s history apply to today’s boom Nov 18, 2025 4731 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 ru

Dave Ricks, CEO of Eli Lilly, on GLP-1s and the business of pharma Nov 11, 2025 7515 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. T

Stablecoin special: Zach Abrams (Bridge) and Henri Stern (Privy) Nov 4, 2025 4449 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 i

Casey Handmer of Terraform Industries on solar maximalism, hard tech, and reclaiming the Salton Sea Oct 28, 2025 4567 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

Dan Sundheim of D1 Capital on the art of public market investing Oct 22, 2025 5888 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

How to build a $16B car company with RJ Scaringe, founder of Rivian Oct 14, 2025 4128 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

Tobi Lütke is still captivated by internet commerce, 20 years later Oct 6, 2025 6175 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

Marc Andreessen and Charlie Songhurst on the past, present, and future of Silicon Valley Oct 1, 2025 7676 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-Ter

Des Traynor on reinventing Intercom twice and the “four horsemen” of good AI companies Sep 24, 2025 4700 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(0

Ambrook CEO Mackenzie Burnett on American agriculture, rural resilience, and carrying 50lbs of fresh pork on Amtrak Sep 17, 2025 3293 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 transcr

Zipline CEO Keller Cliffton on air-dropping blood to Rwandan hospitals and getting to 50,000 aircraft per year Sep 10, 2025 4452 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

Cognition CEO Scott Wu on acquiring Windsurf, AI replacing engineers, and the Moneyball-ification of everything Aug 27, 2025 3473 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-ac

Coinbase CEO Brian Armstrong on bitcoin going to $1 million, electing a pro-crypto Congress, and Jamie Dimon Aug 20, 2025 4591 Brian Armstrong joins John Collison to talk about what’s happening behind the scenes at Coinbase: battling North Korean hackers, war stories from early scaling, confronting people who won’t use AI to code, Coinbase becoming people’s primary financial account, and why banks are now embracing crypto.Full episode transcript on Substackhttps://cheekypint.substack.com/p/coinbase-ceo-brian-arms

Robinhood CEO Vlad Tenev on tokenizing private companies, changing the SEC, and Frank Slootman Aug 13, 2025 3950 Vlad Tenev joins John Collison to discuss Bulgarian hyperinflation, Robinhood Banking, details from the GameStop saga—including advice from Marc Benioff, Mark Zuckerberg, and Elon Musk, payment for order flow economics and Michael Lewis’ Flash Boys, his approach to leadership through the Frank Slootman framework, and how he would change the SEC.Full episode transcript on Substack: https:/

Anthropic CEO Dario Amodei on designing AGI-pilled products, model economics, and 19th-century vitalism Aug 6, 2025 3771 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 agentic future, the economics of model businesses, and the 19th-century concept of vitalism.Full episode transcript on Substack: https://cheekypint.substack.com/p/a-cheeky-pint-with-anthropic-ceoTimestamps(00:00) Intro(00:50) Working with yo

Serial entrepreneur Pieter Levels on building in public and living as a digital nomad Jul 9, 2025 1357 Pieter Levels joins John Collison to discuss building successful online businesses as a digital nomad, thoughts on European accelerationism, and Pieter’s unconventional methods and philosophy as a bootstrapped founder making over $3 million per year.Full episode transcripthttps://cheekypint.transistor.fm/4/transcriptTimestamps(00:00) Intro(00:37) Pieter’s resume(01:33) Trying to make mone

The Bot Company founder and CEO Kyle Vogt on home robots and why he’ll never sell another company Jun 25, 2025 1351 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 similarities between robotics and self-driving, and why the next $100 billion company will have fewer than 100 people.Full episode transcripthttps://cheekypint.transistor.fm/3/transcriptTimestamps(00:00) Intro(00:38) The Bot Company pitch(02:05)

Meta CFO Susan Li on headcount vs. GPU allocation, “free cash flow” hats, and almost becoming a PM Jun 18, 2025 1783 Susan Li of Meta—the youngest chief financial officer of a Fortune 100 company—joins John Collison to talk about capital allocation, managing investors, and how Mark Zuckerberg has changed over the 17 years of working together.Full episode transcripthttps://cheekypint.transistor.fm/2/transcriptTimestamps(00:00) Intro(01:20) Early education and career(02:15) Lessons from Michael Grimes at

OpenAI cofounder Greg Brockman on the scaling hypothesis and refactoring as a killer AI use case Jun 18, 2025 1911 Greg Brockman—OpenAI cofounder and Stripe's first engineer—joins John Collison to talk about research-driven product development, an early moment he thought OpenAI was doomed, S curves in AI advancement, and energy bottlenecks.Full episode transcript:https://cheekypint.transistor.fm/1/transcriptTimestamps(00:00) Intro(02:51) Was OpenAI the first company to take the scaling hypothesis seri

Cheeky Pint hosted by Stripe cofounder John Collison Jun 16, 2025 56 John sits down with founders and builders over a pint—Greg Brockman (cofounder of OpenAI), Susan Li (chief financial officer at Meta), Kyle Vogt (founder of The Bot Company and cofounder of Twitch and Cruise), and Pieter Levels (indie hacker).Watch Cheeky Pint on YouTube: https://youtube.com/@stripe.

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