1821055332
Cheeky Pint

Advertise on podcast: Cheeky Pint

Rating
★★★★★
4.9
from
64 reviews
This podcast has
41 episodes
Language
English
Publisher
Stripe
Explicit
No
Date created
2025/06/16
Latest episode
2026/11/03
Average duration
75 min.
Release period
18 days

Description

Stripe cofounder John Collison interviews founders, builders, and leaders over a pint.

Unlock Cheeky Pint podcast Email contact info,
Listeners & Audience details

Email contact information

Direct podcast contact details

Listeners

Audience numbers & engagement insights

Audience details

Podcast Insights

Podcast episodes

Check latest episodes from Cheeky Pint podcast


The company building America’s uranium supply from scratch
2026/11/03
Scott Nolan, Co-Founder and CEO of General Matter, joins John for a pint to discuss the engineering, economics, and geopolitics behind uranium enrichment. Scott breaks down why advanced reactors can't scale without High-Assay Low-Enriched Uranium (HALEU), why the US outsourced its fuel supply following the Cold War, and how General Matter is building a domestic facility in Paducah, Kentucky, to replace Russian imports. He also shares lessons as an early employee at SpaceX, and why 1970s interest rates stalled nuclear. Timestamps (00:00:00) Introduction (00:00:41) America’s missing nuclear fuel(00:05:27) Why small reactors need stronger fuel (00:11:42) Can nuclear power the AI buildout? (00:15:25) Why nuclear became so expensive (00:22:24) The startups reinventing nuclear (00:25:31) General Matter’s race to 2030 (00:29:44) Stripe Press’ new books (00:30:22) The SpaceX playbook applied to nuclear (00:35:18) Uranium enrichment, explained (00:45:53) How small startups beat stagnant incumbents
Why Sam Altman is against a single superintelligence
2026/10/29
Sam Altman, CEO of OpenAI, joins John to break down how models uncovered critical PHP vulnerabilities, why test-time compute unlocks massive agent swarms, and OpenAI's internal experiments proving complex math problems like Navier-Stokes. He also shares why sandboxing superhuman models is an unsolved safety dilemma, how robotics will scale future gigawatt data centers, and why businesses must adapt as personal agents replace traditional web forms and mobile apps. Timestamps (00:00:00) Introduction (00:00:12) PHP week(00:02:37) Internet early days (00:07:33) Cyber Blue (00:08:54) Sandboxing (00:15:47) Math (00:23:12) Agent swarms (00:24:48) Stripe Atlas (00:25:17) Compute (00:37:53) Revenue per gigawatt (00:49:27) Token pricing is fake
The airline CEO putting Starlink on every plane
2026/10/27
Scott Kirby, CEO of United Airlines, joins John and Ben Thompson to break down the airline business and United’s contrarian bets shaping commercial aviation.  Scott details United’s massive COVID fleet expansion while competitors shrank, why customer surveys are useless for predicting the future, and rolling out SpaceX’s Starlink across the entire fleet. They also cover in-housing seatback software, why low-cost carriers fail, air traffic control bottlenecks, and Scott’s weekend vibe coding projects. Timestamps (00:00:00) Introduction (00:00:26) Buying planes while the world shrank(00:06:35) Owning the airline tech stack (00:22:02) Aviation’s biggest bottleneck (00:26:21) Stripe Economics (00:26:59) Hidden economics of airline networks (00:30:19) Starlink (00:38:28) What Wall Street gets wrong about aviation (00:43:43) It’s the routes  (00:55:44) Why Spirit failed but Ryanair works (01:15:38) Kirby’s unusual time management hacks Scott’s reading list:  Unreasonable Hospitality – Will Guidara The Impossible Factory – Josh Dean Freedom’s Forge – Arthur Herman The Sleepless Ape – David R. Samson Sea of Tranquility – Emily St. John Mandel The End of Eternity – Isaac Asimov Tolkien and the Great War – John Garth
How Toto Wolff built the most valuable team in F1
2026/10/20
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" hiring policy across 2,500 employees, and how the F1 cost cap transformed racing teams into $1B+ assets. He also shares his early career as a dot-com investor, the team’s "Navy SEALs" approach to car development, and why he believes live sports are immune to AI disruption. Timestamps (00:00:22) Spotting driver talent (00:06:24) Engineering and team selection (00:09:11) The F1 cost cap (00:25:21) Toto’s early investing career (00:38:15) Running Mercedes as an owner (00:46:47) Why F1 team values exploded (01:08:24) Succession planning
The company building underwater drones for $50,000
2026/10/15
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 super-sequester of carbon, and the engineering required to operate robots thousands of meters beneath the surface. Will also breaks down Ulysses' vertical integration strategy, the reality of eco-pragmatism versus "green tape," and what it takes to sell hard tech to defense and offshore energy sectors. Timestamps (00:00:30) R&D at Guinness (00:05:43) Planting seagrass with robots (00:16:53) Lowering the cost of doing things in the ocean (00:19:00) Landing in a Chinese prison(00:20:38) Works in Progress (00:27:53) Building robots to withstand saltwater (00:31:08) Live use cases for underwater robots (00:46:03) The undersea cable vulnerability Resources: Guinness Quality Standards: https://www.guinnesscelebrate.com/our-quality/quality-standards No Great Stagnation in Guinness by Will O’Brien: https://www.thefitzwilliam.com/p/no-great-stagnation-in-guinness
Muse Wonder: Zuckerberg and Wang's $100B AI
2026/10/12
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 of Meta Superintelligence Labs (MSL), the decision to execute a complete talent reboot, and what it really feels like to make a $100B+ CapEx commitment before knowing if the model will work. They dive deep into the architecture of Muse Wonder—including active memory, multimodal perception, and frontier coding—while laying out their vision for agentic commerce, hardware form factors like smart glasses, and why superintelligence belongs in the hands of billions. Timestamps (00:00:24) Muse’s breakout use cases (00:07:28) Why the model is the product (00:14:35) Meet Muse Wonder (00:24:56) How frontier models are actually built (00:48:26) Betting $100B(01:07:21) Agentic commerce (01:19:34) OpenRouter (01:20:06) Beyond the smartphone (01:27:00) Funding(01:34:06) Why AI won’t be winner-take-all (01:40:46) Meta Superintelligence Labs (MSL) (02:08:11) Working for Mark Zuckerberg
What comes after smartphones, with Snap CEO Evan Spiegel
2026/04/27
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 glasses form factor, why Snap built its own OS from scratch, and how Claude is transforming their software development, with over two-thirds of Snap’s new code now written by AI. Plus, the pair dig into the complex reality of teen phone usage, the distinction between social and media, and why Norway was the first country to embrace Snapchat. Timestamps (00:00:15) Snap’s crucible moment (00:01:05) Specs (00:09:12) AR as the right form factor (00:20:45) Stablecoin payouts on Stripe (00:21:46) Monetizing the camera (00:28:13) Social media vs messaging (00:47:37) Content moderation (00:59:49) Snap’s evolution
The economics and trends of the restaurant industry, with Tony Xu of DoorDash
2026/04/21
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 reputation. Tony introduces Dot, their new autonomous delivery robot, and explains why true autonomy requires solving for the “last two feet” of delivery. Finally, he shares lessons from the early days, including why customer obsession sometimes means baking cookies. Timestamps (00:00:25) Why did DoorDash win? (00:10:50) China (00:17:10) Restaurant trends (00:27:59) Loyalty (00:30:40) Stripe Issuing (00:44:09) Delivery modalities (00:51:11) Fraud (00:58:32) New products (01:13:26) Dot
The world of voice AI, with Mati Staniszewski of ElevenLabs
2026/04/14
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 massive potential for voice agents in everything from farming to healthcare. Mati also opens up about ElevenLabs’ rapid ascent to an $11 billion valuation and gives a behind-the-scenes look at how Ukraine is using their tech for digital government services. Timestamps (00:00:27) How audio models work (00:08:52) ElevenLabs business model (00:17:50) The conversational Turing Test (00:21:01) Link by Stripe (00:26:02) Cascaded vs speech-to-speech (00:31:53) Universal translation (00:51:41) Designing an AI-native org
The history and future of AI at Google, with Sundar Pichai
2026/04/07
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" optimism. Sundar also shares details on long-term bets like data centers in space, why he wishes he had funded Waymo even faster, and the small thing inside Google that still ignites his passion for building. Timestamps (00:00:18) The history of Google and AI (00:05:17) Speed and Search (00:12:12) Google’s AI comeback (00:27:03) Stripe network intelligence (00:27:53) Bottlenecks (00:41:25) Capital allocation (01:00:44) How Google works
Compliance at scale and why TAM is a distraction with Christina Cacioppo of Vanta
2026/03/31
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 b******t." They cover the tension between vibe coding and rigorous security, how Vanta is using agents to generate UI, and why the best founders are relentless truth-seekers. Timestamps (00:00:17) Vanta (00:12:30) How compliance works (00:15:06) Breaches (00:23:52) Stripe Tax (00:24:43) AI and compliance (00:44:50) Go-to-market (00:47:22) Lessons from USV
The 20-year journey to fully autonomous cars with Dmitri Dolgov of Waymo
2026/03/24
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 naturally evolve into robotaxis. They also cover the new custom-built vehicle that feels like a living room, the economics of ride-hailing in rural Alaska, and the "Russian math nerd" diaspora that seems to run the UK tech scene. Timestamps (00:00:22) Russia (00:02:51) Waymo architecture (00:09:59) Why now? (00:19:46) Driving nuance (00:29:37) Stripe Agentic Commerce Suite (00:30:17) Hardware (00:40:20) Emergent behavior (00:46:36) Scaling (00:57:56) Google Article: EMMA: End-to-End Multimodal Model for Autonomous Driving – Waymo Research: https://waymo.com/research/emma/
Creating prediction markets (and suing the CFTC) with Tarek Mansour and Luana Lopes Lara
2026/03/17
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 antidote to social media polarization, the mechanics of market making for culture, and their vision for trading everything from GPU shipments to the Oscars and the weather. Timestamps (00:01:39) Suing the government (00:14:42) Why now? (00:17:12) Kalshi by numbers (00:20:58) Solving market making (00:31:33) Agentic trading (00:33:43) Sharps (00:38:45) Stripe Connect (00:39:33) Evolving Kalshi (00:44:50) Who loses from Kalshi? (00:47:35) Insider trading (00:53:28) The ethics of sports contracts (00:58:08) New derivatives (01:04:27) Politics Article(s): On the Observational Implications of Knightian Uncertainty – Kevin Hassett & Weifeng Zhong (AEI)The 2028 Global Intelligence Crisis – Citrini Research
Bret Taylor of Sierra on AI agents, outcome-based pricing, and the OpenAI board
2026/03/10
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 “shipping their org charts.” Bret also discusses a new type of hyper-generalist, reflects on his experience with the OpenAI and Twitter boards, and explains why he believes we might see the end of the smartphone era. Timestamps (00:00:26) Coding (00:16:23) Sierra (00:27:14) Agentic UX (00:38:47) Building support agents (00:45:43) Co-developing with the models (00:50:08) SaaSpocalypse (01:00:50) Stripe Sessions (01:01:33) Outcome-based pricing (01:09:14) Is Sierra short AGI? (01:13:50) AI productivity (01:23:47) How to structure a tech business (01:30:25) Board drama (01:38:24) AI predictions
Garrett Langley of Flock Safety on building technology to solve crime
2026/03/05
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 of criminal technology, why hardware requires making "one-way door" decisions, and his vision for a future where technology prevents crime before it happens. Timestamps(00:00:19) Flock (00:19:51) Safety vs privacy (00:23:54) Crime and technology (00:32:36) Crime rates (00:43:56) Corporate security (00:52:16) Stripe Radar (00:52:54) Competitive landscape (01:02:41) Drones (01:09:01) The Flock business (01:11:39) Building hardware (01:20:01) Cameras (01:25:17) PD procurement (01:32:56) Building your own drones (01:40:52) What’s next for Flock? Books: The Digital Silk Road: https://www.amazon.com/Digital-Silk-Road-Chinas-Future/dp/0063046288 Boyd: https://www.amazon.co.uk/Boyd-Fighter-Pilot-Who-Changed/dp/0316796883

Podcast reviews

Read Cheeky Pint podcast reviews


4.9 out of 5
64 reviews
★★★★★
edwinarbus 2025/11/29
Host is very smart
He should start a payments company or something; seems very knowledgeable
★☆☆☆☆
Anonymous college kid 2025/09/25
Please change this
I love this show, but the transition sound to commercial sounds just like the Doppler effect of a car horn speeding towards you. It gives me a heart a...
★★★★★
Avid pod listener7 2025/09/13
Longer is better
Great show
★★★★★
ZachTXM 2025/06/20
Love it!
I love how they keep the episodes reasonable short instead of like an hour. Guests have been great so far. Gotta finish your beer though
check all reviews on apple podcasts

Podcast sponsorship advertising

Start advertising on Cheeky Pint relevant audience podcasts


What do you want to promote?