# Cheeky Pint: the investor podcast, by episode

> Cheeky Pint: Stripe's co-founder over a pint with founders and investors. 38 episodes, each linked to the investors in it.

Source: https://millionrounds.com/podcasts/cheeky-pint (Millionrounds; every figure on the page links to its filing or article)

Founders · new episode 20 Oct 2026

# Cheeky Pint

Hosted by **John Collison, Stripe**

Stripe's co-founder over a pint with founders and investors.

Follow on Apple PodcastsBrowse the episodes

**38** episodes

**12** investors heard as guests

**1h 12m** an average episode

22 in the last 12 months

## The regulars

Investors named as guests in the most episode titles on Cheeky Pint.

[BT *1* **Ben Thompson** GitPrime](https://millionrounds.com/person/ben-thompson)[CC *1* **Christina Cacioppo** 1 episode](https://millionrounds.com/person/christina-cacioppo-2)[EG *1* **Eric Glyman** Silicon Valley Investclub](https://millionrounds.com/person/eric-glyman)[ES *1* **Evan Spiegel** 1 episode](https://millionrounds.com/person/evan-spiegel)[GL *1* **Garrett Langley** Flock Safety](https://millionrounds.com/person/garrett-langley-2)[HS *1* **Henri Stern** Notation Capital](https://millionrounds.com/person/henri-stern)[JD *1* **Julia DeWahl** 1 episode](https://millionrounds.com/person/julia-dewahl)[LL *1* **Luana Lopes** 1 episode](https://millionrounds.com/person/luana-lopes)[RS *1* **RJ Scaringe** Rivian](https://millionrounds.com/person/rj-scaringe)[SN *1* **Satya Nadella** Microsoft](https://millionrounds.com/person/satya-nadella)[SL *1* **Susan Li** Meta](https://millionrounds.com/person/susan-li)[VT *1* **Vlad Tenev** Robinhood](https://millionrounds.com/person/vlad-tenev)

## Every episode 38 · page 1 of 2

- 38 **How Toto Wolff built the most valuable team in F1** 20 Oct 2026 · 1h 11m About this episode Toto Wolff, Team Principal and Co-Owner of the Mercedes-AMG PETRONAS F1 Team, joins John Collison for a pint to discuss the engineering, management, and economics behind modern Formula 1. Toto breaks down how Mercedes spots generational driver talent as early as age eight, why they enforce a strict "No Dickheads"… ▶Show page
- 37 **The company building underwater drones for $50,000** 15 Oct 2026 · 50 min [Chris Sacca](https://millionrounds.com/fund/chris-sacca) About this episode Will O'Brien, founder and CEO of Ulysses, joins John and Chris Sacca for a pint to discuss how underwater autonomous robots are scaling up to solve critical ocean challenges. They cover the technical history of Guinness (including the math breakthrough that created Student's t-test), why seagrass is an overlooked… ▶Show page
- 36 **Muse Wonder: Zuckerberg and Wang's $100B AI** 12 Oct 2026 · 2h 14m [Mark Zuckerberg](https://millionrounds.com/fund/mark-zuckerberg)[Alexandr Wang](https://millionrounds.com/person/alexandr-wang) About this episode As Meta scales its AI infrastructure past five gigawatts, Mark Zuckerberg (founder and CEO, Meta) and Alexandr Wang (Chief AI Officer, Meta Superintelligence Labs) join John for a pint to discuss the launch of Muse Wonder and the future of personal AI agents. In this episode, Mark and Alex open up about the creation… ▶Show page
- 35 **What comes after smartphones, with Snap CEO Evan Spiegel** 27 Apr 2026 · 1h 2m [Evan Spiegel](https://millionrounds.com/person/evan-spiegel) About this episode 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.… ▶Show page
- 34 **The economics and trends of the restaurant industry, with Tony Xu of DoorDash** 21 Apr 2026 · 1h 21m [Tony Xu](https://millionrounds.com/fund/tony-xu)[Google](https://millionrounds.com/fund/google-assistant-investments) About this episode 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… ▶Show page
- 33 **The world of voice AI, with Mati Staniszewski of ElevenLabs** 14 Apr 2026 · 1h 0m [Mati Staniszewski](https://millionrounds.com/fund/mati-staniszewski) About this episode 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,… ▶Show page
- 32 **The history and future of AI at Google, with Sundar Pichai** 7 Apr 2026 · 1h 9m [Google](https://millionrounds.com/fund/google-assistant-investments)[Elad Gil](https://millionrounds.com/fund/elad-gil) About this episode 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… ▶Show page
- 31 **Compliance at scale and why TAM is a distraction with Christina Cacioppo of Vanta** 31 Mar 2026 · 57 min [Christina Cacioppo](https://millionrounds.com/person/christina-cacioppo-2) About this episode 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… ▶Show page
- 30 **The 20-year journey to fully autonomous cars with Dmitri Dolgov of Waymo** 24 Mar 2026 · 1h 2m [Google](https://millionrounds.com/fund/google-assistant-investments) About this episode 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,… ▶Show page
- 29 **Creating prediction markets (and suing the CFTC) with Tarek Mansour and Luana Lopes Lara** 17 Mar 2026 · 1h 17m [Luana Lopes](https://millionrounds.com/person/luana-lopes)[Matt Huang](https://millionrounds.com/fund/matt-huang) About this episode 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… ▶Show page
- 28 **Bret Taylor of Sierra on AI agents, outcome-based pricing, and the OpenAI board** 10 Mar 2026 · 1h 41m [Bret Taylor](https://millionrounds.com/fund/bret-taylor) About this episode 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… ▶Show page
- 27 **Garrett Langley of Flock Safety on building technology to solve crime** 5 Mar 2026 · 1h 44m [Garrett Langley](https://millionrounds.com/person/garrett-langley-2) About this episode 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… ▶Show page
- 26 **Reiner Pope of MatX on accelerating AI with transformer-optimized chips** 26 Feb 2026 · 1h 13m [Google](https://millionrounds.com/fund/google-assistant-investments) About this episode 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… ▶Show page
- 25 **Stripe’s 2025 annual letter** 24 Feb 2026 · 28 min [Republic](https://millionrounds.com/fund/republic-2) About this episode 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… ▶Show page
- 24 **Ramp founder Eric Glyman on the many ways AI is changing corporate spending** 17 Feb 2026 · 1h 11m [Eric Glyman](https://millionrounds.com/person/eric-glyman)[Alex Rampell](https://millionrounds.com/fund/alex-rampell)[Capital One](https://millionrounds.com/fund/capital-one) About this episode 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… ▶Show page
- 23 **Ben Thompson from Stratechery on AI ads, the end of SaaS, and the future of media** 12 Feb 2026 · 1h 30m [Ben Thompson](https://millionrounds.com/person/ben-thompson) About this episode 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… ▶Show page
- 22 **Elon Musk on Space GPUs, AI, Optimus, and his manufacturing method** 5 Feb 2026 · 2h 46m About this episode 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… ▶Show page
- 21 **Julia DeWahl of Antares on building nuclear reactors for the US military** 25 Nov 2025 · 45 min [Julia DeWahl](https://millionrounds.com/person/julia-dewahl) About this episode 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… ▶Show page
- 20 **Satya Nadella describes how lessons from Microsoft’s history apply to today’s boom** 18 Nov 2025 · 1h 19m [Satya Nadella](https://millionrounds.com/person/satya-nadella)[Bill Gates](https://millionrounds.com/fund/bill-gates)[Larry Ellison](https://millionrounds.com/person/larry-ellison) About this episode 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… ▶Show page
- 19 **Dave Ricks, CEO of Eli Lilly, on GLP-1s and the business of pharma** 11 Nov 2025 · 2h 5m [Eli Lilly](https://millionrounds.com/fund/eli-lilly) About this episode 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… ▶Show page
- 18 **Stablecoin special: Zach Abrams (Bridge) and Henri Stern (Privy)** 4 Nov 2025 · 1h 14m [Henri Stern](https://millionrounds.com/person/henri-stern)[Zach Abrams](https://millionrounds.com/fund/zach-abrams) About this episode 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… ▶Show page
- 17 **Casey Handmer of Terraform Industries on solar maximalism, hard tech, and reclaiming the Salton Sea** 28 Oct 2025 · 1h 16m About this episode 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 another 10x, and the core physics that doomed Hyperloop from the… ▶Show page
- 16 **Dan Sundheim of D1 Capital on the art of public market investing** 22 Oct 2025 · 1h 38m About this episode 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… ▶Show page
- 15 **How to build a $16B car company with RJ Scaringe, founder of Rivian** 14 Oct 2025 · 1h 9m [RJ Scaringe](https://millionrounds.com/person/rj-scaringe) About this episode 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… ▶Show page
- 14 **Tobi Lütke is still captivated by internet commerce, 20 years later** 6 Oct 2025 · 1h 43m About this episode 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… ▶Show page
- 13 **Marc Andreessen and Charlie Songhurst on the past, present, and future of Silicon Valley** 1 Oct 2025 · 2h 8m [Charlie Songhurst](https://millionrounds.com/fund/charlie-songhurst)[Marc Andreessen](https://millionrounds.com/fund/marc-andreessen)[Andreessen Horowitz](https://millionrounds.com/fund/andreessen-horowitz) About this episode 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… ▶Show page
- 12 **Des Traynor on reinventing Intercom twice and the “four horsemen” of good AI companies** 24 Sept 2025 · 1h 18m [Des Traynor](https://millionrounds.com/fund/des-traynor) About this episode 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:… ▶Show page
- 11 **Ambrook CEO Mackenzie Burnett on American agriculture, rural resilience, and carrying 50lbs of fresh pork on Amtrak** 17 Sept 2025 · 55 min [Dylan Field](https://millionrounds.com/fund/dylan-field)[Joshua Kushner](https://millionrounds.com/fund/joshua-kushner) About this episode 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 Mentioned Farming goes digital The… ▶Show page
- 10 **Zipline CEO Keller Cliffton on air-dropping blood to Rwandan hospitals and getting to 50,000 aircraft per year** 10 Sept 2025 · 1h 14m About this episode 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 Wolfe Skunk Works by Ben Rich Apple… ▶Show page
- 9 **Cognition CEO Scott Wu on acquiring Windsurf, AI replacing engineers, and the Moneyball-ification of everything** 27 Aug 2025 · 58 min [Alexandr Wang](https://millionrounds.com/person/alexandr-wang) About this episode 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… ▶Show page

## Who the show talks about

Firms named in its episodes, and people named in descriptions: talked about, rather than on the show.

[**Google** *4*](https://millionrounds.com/fund/google-assistant-investments)[M **Mark Zuckerberg** *3*](https://millionrounds.com/fund/mark-zuckerberg)[A **Alexandr Wang** *2*](https://millionrounds.com/person/alexandr-wang)[**Greg Brockman** *2*](https://millionrounds.com/fund/greg-brockman)[K **Kyle Vogt** *2*](https://millionrounds.com/fund/kyle-vogt)[A **Alex Rampell** *1*](https://millionrounds.com/fund/alex-rampell)[**Andreessen Horowitz** *1*](https://millionrounds.com/fund/andreessen-horowitz)[B **Bill Gates** *1*](https://millionrounds.com/fund/bill-gates)[B **Bret Taylor** *1*](https://millionrounds.com/fund/bret-taylor)[C **Capital One** *1*](https://millionrounds.com/fund/capital-one)[C **Charlie Songhurst** *1*](https://millionrounds.com/fund/charlie-songhurst)[**Chris Sacca** *1*](https://millionrounds.com/fund/chris-sacca)

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