Cheeky Pint

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 (00:27:53) 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:…

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…

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

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

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

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

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 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

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/

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 &…

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 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:…

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 logistical challenge of manufacturing chips at scale with TSMC. Reiner also shares his predictions for AI in 2027, why he prefers Rust for hardware design, and why the best iteration loops happen in your head before writing a line of code. Timestamps (00:00:15) Google’s AI revival (00:07:54) MatX (00:17:11) AI supply chain (00:21:48) Designing chips (00:37:11) TSMC (00:44:17) Token pricing (00:44:55) RL-ing chip design (00:49:26) Design to production (00:56:05) MatX culture (01:02:57) Rust (01:05:21) Cuckoo hashing (01:09:35) Unexplored model architectures

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 sorting machine (05:45) Global by default (09:01) Stable progress (12:14) Working capital’s working. Capital! (15:09) Escaping from low revenue mode (18:33) The five levels of agentic commerce (23:52) A Republic of Permissions

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 a liability), how Ramp uses AI agents to review 100,000 expenses a day with 99% accuracy, and why their internal data suggests the US economy is much stronger than the Census Bureau reports. Timestamps (00:00:21) Ramp business today (00:04:27) The *correct* expense policy (00:11:07) Bill Pay (00:16:52) AI and software (00:32:23) Stablecoin-backed cards (00:33:06) Ramp data (00:36:25) How to cut your expenses (00:41:13) Ramp strategy (00:57:08) Capital One (01:06:34) Treasury

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 failure to control the TikTok algorithm is a disaster, why he’s a "crypto defender" in an age of infinite AI content, and gives John some very direct feedback on Stripe’s ACH implementation. Timestamps (00:00:20) Visiting Taiwan (00:04:59) Aggregation and AI (00:23:53) TikTok/Bytedance (00:29:58) Aggregation and AI redux (00:35:31) Agentic commerce (00:45:08) Is SaaS canceled? (00:52:21) Stratechery (01:03:36) How Ben uses AI (01:06:06) The TSMC break (01:13:53) Rapid fire (01:20:53) Feedback on Stripe

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, and DOGE. Timestamps 00:00:23 Space GPUs 00:35:39 Alignment 00:58:48 xAI 01:15:01 Optimus 01:28:03 China 01:40:46 Management 02:16:38 DOGE 02:34:58 Space GPUs redux

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 of reactors), and why true energy resilience requires more than just solar and batteries. Julia also shares lessons from the early days of Opendoor and Starlink, including why customer obsession sometimes means sitting outside a bagel shop. Timestamps (00:00) Lessons from SpaceX and Opendoor (02:46) Introducing Antares (06:30) The path to market (12:20) Nuclear vibe shift (15:11) Regulation (19:21) Possible energy futures (24:02) Stripe Radar (24:55) Nuclear supply chains (26:43) Antares origin story (30:24) Funding Antares (36:09) If Julia was energy tsar (42:33) Restarting shuttered plants

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 run the company. Links [Read] Softwar: An Intimate Portrait of Larry Ellison and Oracle, Matthew Symonds [Try] Superwhisper [Read] The Internet Tidal Wave, Bill Gates Timestamps (00:00) AI adoption in the enterprise (07:47) How Satya runs Microsoft (13:45) New UIs (20:44) Microsoft tackling the early internet (25:58) Are we in a bubble? (31:35) Data sovereignty (38:10) Excel (42:01) Agentic commerce (52:45) AI brand loyalty (59:44) Product bundling (01:08:18) Microsoft’s culture (01:12:12) The law of very large companies (01:16:20) What’s in the water in Hyderabad?

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. They cover the "shadow generic" industry undermining patents, the challenges associated with clinical trial enrollment, and what drove insulin list prices to $275 (while the net price was $40). This is a rare, candid look into the strategies, science, and future of pharma from one of the industry's most influential leaders. Timestamps (00:00) Introducing Dave Ricks (05:07) Making R&D decisions (10:10) Clinical trials (24:59) Drug pricing (32:43) Stimulating more R&D (54:15) Pros and cons of US healthcare (58:20) New pharma business models (01:05:53) Stripe and enterprises (01:07:00) China (01:16:31) Generics (01:22:37) GLP-1s…

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 is changing financial infrastructure. Key moments (00:00) Introducing Bridge + Privy (06:39) How stablecoins are being used today (14:27) US Dollar dominance (25:50) The future of banking (34:35) Blockchains (42:27) Building a modular stack (47:14) Open issuance (56:55) M&A (01:11:02) The future of stablecoins

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 start. They also discuss the lessons of the underappreciated industrialist Henry Kaiser, Casey's new venture in solar-powered desalination, his grand plan to refill the Salton Sea, and why he believes "hard-edged" leaders are essential for hardware success. Show notes [Read] Ashlee Vance: Elon Musk [Read] Francis Spufford: Red plenty [Listen] Beneath the Surface, Episode 2 : Salton Sea [Read] Marc Reisner: Cadillac Desert [Read] Albert P. Heiner: Henry J. Kaiser [Read] Mark S. Foster: Henry Kaiser [Read] Ernest K. Gann: Fate is the Hunter [Read] Captain W. E. Johns: Biggles: The Camels are Coming Key moments (00:00) Intro (02:28) Henry Kaiser (08:49) Introducing Terraform (13:08) Where electricity…

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 that comes from years of investing. This is a rare, candid look into the strategies and mindset of a top public markets investor. Show notes [Read] The Essays of Warren Buffett: Lessons for Corporate America by Lawrence A. Cunningham [Read] The Buffett Partnership Letters (1957-1970) [Read] Value Investors Club (VIC) Timestamps (00:00) The D1 operating model (07:54) Getting it wrong on NFLX (11:44) What makes a good stock picker (18:16) Portfolio-building (24:35) GameStop (35:57) The art of short-selling (41:48) How to spot a turnaround (47:12) Waking up at 3 AM (53:14) Money management (59:31) Dan’s 10-year hands-off stock…

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 2 (18:37) Developing the first electric pickup truck (27:36) John pitches some car features (36:46) Stripe’s payment methods (37:54) Autonomous driving (44:51) Component progress (53:17) The new economics of cars (01:01:11) Manufacturing in the US

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 notes [Buy] Momax: 140W Universal Travel Adapter [Read] Benjamin Bloom: The 2 Sigma Problem [Buy] Ikigai: vitamin cases [Read] Kevin Kelly: 1,000 True Fans [Read] Erich Gamma: Design Patterns [Read] Charles Calomiris: Fragile by Design [Listen] Business Breakdowns: Formula One [Watch] Netflix: Formula 1: Drive to Survive [Read] Mark Robichaux: Cable Cowboy Key Moments (00:00) Intro (07:07) How internal software shapes culture (16:32) The Shopify vision (27:49) Peak transaction capacity (34:36) Agentic commerce (49:15) Shop Pay (55:29) Stablecoins (59:20) Stripe + Shopify (1:12:23) Learning from the Coinbase board (1:17:23)…

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-Term Capital Management David Swensen: Pioneering Portfolio Management Ian M Banks: Consider Phlebas: A Culture Novel Walter Isaacson: Elon Musk Thomas Rid: Rise of the Machines: A Cybernetic History George McGovern: A Politician's Dream Is a Businessman's Nightmare, WSJ Steve Blank: The Secret History of Silicon Valley Tracy Kidder: The Soul of a New Machine John Perry Barlow: A Declaration of the Independence of Cyberspace Martin Gurri: Revolt of the Public John Malone: Born to Be Wired Full transcript on Substack: https://cheekypint.substack.com/p/marc-andreessen-and-charlie-songhurst Subscribe to Cheeky Pint Spotify:…

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-intercom Timestamps: (00:00) Intro (02:58) Reinventing Intercom (06:31) Fin (18:06) 1M resolutions a week (24:22) Selling AI (29:34) Product marketing (37:18) Listening to users (44:14) Usage-based billing (45:14) Advice for startups (52:09) AI pricing (01:07:27) Cofounder dynamics (01:11:04) Predictors of company success (01:15:56) How AI-native is Intercom?

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 End of Accounting and the Path Forward for Investors and Managers Full transcript on Substack: https://cheekypint.substack.com/p/ambrook-ceo-mackenzie-burnett-on Timestamps: (00:00) Introducing Ambrook (05:37) Serving farmers (19:25) Building rural resilience (21:49) The economics of ag (28:03) If Mackenzie ran the USDA (30:53) Vertical SaaS (34:49) The wonders of accounting (38:41) Ambrook-as-fintech (44:00) If Mackenzie ran Stripe (50:53) Joshua Kushner and Dylan Field

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 in China by Patrick McGee Timestamps (00:00) Intro (00:45) 115 million miles flown (04:10) Why drone delivery took so long (07:38) Getting started in Rwanda (13:31) 51% reduction in maternal mortality (15:33) Access vs. waste (21:45) Scaling globally (24:05) Zipline’s Platform 1 (25:50) The Right Stuff (27:22) Drone design and safety (30:12) Getting to 99.9% reliability (34:39) Multimodal logistics (38:15) Zipline’s Platform 2 (44:03) US drone regs and the FAA (48:02) Progress and stagnation in US aviation (51:30) If Keller ran the FAA (54:24) 30% WoW growth in Texas (58:25) Why Texas and not California? (01:00:28) Building 50k drones in California (01:06:18) US vs. Chinese manufacturing (01:11:30)…

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-acquiring Timestamps (00:00) Intro (01:13) Early life and maths competitions (03:47) Addepar job as a high schooler (05:43) Where are all the young founders? (08:45) Moneyball-ification of everything (11:42) Cognition’s AI software engineer, Devin (15:46) Essential and accidental complexity (17:59) How Devin works with enterprises (19:48) IDE productivity (21:56) Nihilist computer use argument (25:55) Benchmarking Devin (27:15) Market structure (30:32) Agent economy (37:21) Cognition’s team of founders (39:31) Jevons paradox and software (42:00) When will we see AI UIs? (45:52) “I think we have AGI” (47:03) Windsurf deal…

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 Substack https://cheekypint.substack.com/p/coinbase-ceo-brian-armstrong-on-bitcoin Timestamps (00:00) Intro (01:14) How Coinbase won the exchange market (06:22) Losing money on every bitcoin purchase (10:54) North Korean hackers (14:54) The Everything Exchange (17:39) Crypto will be bigger than gold (19:22) Stablecoin adoption (23:28) Jamie Dimon and big banks on crypto (26:44) Coinbase as your primary financial account (27:53) Neobanks (29:41) Bitcoin going to $1 million (33:16) Crypto in an investment portfolio (34:43) GENIUS Act (37:10) Electing a pro-crypto Congress (45:24) Reforming accredited investor rules (48:33) Squashing scams (50:11) Bitcoin preserving the American experiment…

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://cheekypint.substack.com/p/robinhood-ceo-vlad-tenev-makes-his Timestamps (00:00) Intro (00:58) Hyperinflation in Bulgaria (04:07) Stablecoins (05:41) Home country bias in investing (06:59) Robinhood’s origins (11:23) What the book Flash Boys got wrong (16:11) Options vs. equities (17:38) Robinhood Gold (19:34) Robinhood Banking (22:04) GameStop advice from Benioff, Zuck, and Elon (26:40) Impact of retail investors on capital markets (31:21) Where retail dollars are coming from (32:10) The gamification narrative (34:17) Tokenizing private companies (41:57) Vlad makes his pitch to tokenize Stripe (45:00) Prediction markets:…

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-ceo Timestamps (00:00) Intro (00:50) Working with your sibling (01:43) Building Anthropic with 7 cofounders (02:52) ~$5 billion in ARR and vertical applications of products (07:18) Developing a platform-first company (10:08) Working with the DoD (11:11) Proving skeptics wrong about revenue projections (13:13) Capitalistic impulses of AI models (15:43) AI market structure and players (16:56) AI models as standalone P&Ls (20:48) The data wall and styles of learning (22:20) AI talent wars (26:04) Pitching Anthropic’s API business to investors (27:49) Cloud providers vs. AI labs (29:05) AI customization and Claude for enterprise (33:01) Dwarkesh’s take on limitations (36:12)…

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 transcript https://cheekypint.transistor.fm/4/transcript Timestamps (00:00) Intro (00:37) Pieter’s resume (01:33) Trying to make money online as a 12 year old (02:43) Being one of the first YouTube creators (03:18) Who should indie hack (04:31) What Pieter hates about VC-backed businesses (07:51) Who is digital nomading for? (09:15) Learning from @patio11 (10:17) 125k tweets and the brand of @levelsio (10:59) Getting referrals from ChatGPT (11:43) What Pieter automates with AI (13:02) Investing and home country bias (15:05) Hacking thermostats (15:57) EU acceleration movement (18:34) Entrepreneurship in the EU (19:26) Pieter's reflections on Stripe’s API (21:21) Looking 5 years into the future

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 transcript https://cheekypint.transistor.fm/3/transcript Timestamps (00:00) Intro (00:38) The Bot Company pitch (02:05) Single-task vs. multi-task robots (04:27) What is the Turing test for robotics? (05:52) Why this time is different for home robots (08:42) The last mile in robotics and self-driving (09:47) Viral demos and hype cycles (10:38) Commercializing frontier tech (13:06) Self-driving CapEx (14:15) Regulatory hurdles (16:18) Tesla vs. Waymo (19:21) Why Kyle regrets selling Cruise (21:39) The next $100 billion company

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 transcript https://cheekypint.transistor.fm/2/transcript Timestamps (00:00) Intro (01:20) Early education and career (02:15) Lessons from Michael Grimes at Morgan Stanley (03:12) Leadership traits and succession planning at Meta (06:05) Mark Zuckerberg’s leadership and culture of feedback (09:06) Financial forecasting and capital allocation (14:18) ROI on Meta’s portfolio of bets (15:05) Investor sentiment in 2022 (17:49) The story behind the “free cash flow” hats (18:58) CapEx trends in the AI era (21:48) A memorable earnings call (24:16) Challenges of allocating compute vs headcount budgets (26:55) AI’s impact on productivity and operations

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/transcript Timestamps (00:00) Intro (02:51) Was OpenAI the first company to take the scaling hypothesis seriously? (04:53) Lessons from Dota about deep learning (08:08) What is a good new Turing test? (08:57) Personalization in AI (09:57) Research-driven product development (10:26) An early moment OpenAI felt doomed (15:01) OS limits on AI product development (17:59) When will AI make novel advancements in math or science? (20:03) Energy bottlenecks (22:30) S curves in AI advancement (24:00) AI coding (26:25) Refactoring as a killer AI use case (27:26) How OpenAI decides what products to built (28:53) Growing up in North Dakota (30:17) How far away is AGI?

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.