Cheeky Pint

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) GoogleArticle: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) PoliticsArticle(s):On the Observational Implications of Knightian Uncertainty – Kevin Hassett & Weifeng Zhong (AEI)The 2028 Global Intelligence Crisis – Citrini Research

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: https://www.amazon.com/Digital-Silk-Road-Chinas-Future/dp/0063046288Boyd: https://www.amazon.co.uk/Boyd-Fighter-Pilot-Who-Changed/dp/0316796883 

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.Timestamps00:00:23 Space GPUs00:35:39 Alignment00:58:48 xAI01:15:01 Optimus01:28:03 China01:40:46 Management02:16:38 DOGE02:34:58 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 GatesTimestamps(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(1:37:43) r/Peptides(01:41:25) LillyDirect(01:46:35) Why do investors love LLY?

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

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 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 ComingKey moments(00:00) Intro(02:28) Henry Kaiser(08:49) Introducing Terraform(13:08) Where electricity won’t work(16:50) The solar maximalist perspective(22:57) Terraformer Mark One(27:49) The role of intervention(37:30) American dynamism(47:36) The Origins of Efficiency, by Brian Potter(48:33) Children and education(37:30) American dynamism(55:15) Desalination(01:08:16) Lessons from leadership

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 pick(01:09:52) China(01:14:44) Are we in a bubble?(01:20:41) SpaceX(01:25:04) Investing in private companies(01:32:55) Thoughts on the banking industry(01:35:58) Advice for budding investors

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 CowboyKey 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) Is Tobi ungovernable?(1:25:02) Entrepreneurship(1:31:50) Advice for Mark Carney(1:36:40) Motor racing

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 ManagementDavid Swensen: Pioneering Portfolio ManagementIan M Banks: Consider Phlebas: A Culture NovelWalter Isaacson: Elon MuskThomas Rid: Rise of the Machines: A Cybernetic HistoryGeorge McGovern: A Politician's Dream Is a Businessman's Nightmare, WSJSteve Blank: The Secret History of Silicon ValleyTracy Kidder: The Soul of a New MachineJohn Perry Barlow: A Declaration of the Independence of CyberspaceMartin Gurri: Revolt of the PublicJohn Malone: Born to Be WiredFull transcript on Substack: https://cheekypint.substack.com/p/marc-andreessen-and-charlie-songhurst Subscribe to Cheeky PintSpotify: https://open.spotify.com/show/2IHbGJJMpiFoz5YrvRfTFwApple Podcasts: https://podcasts.apple.com/us/podcast/cheeky-pint/id1821055332Substack: https://cheekypint.substack.com/Key moments(00:00) Marc needs to know: what is a cheeky pint?(04:30) Are we in a bubble?(14:55) Do VCs matter?(19:01) The history of Silicon Valley(32:25) How Digital Research almost made it(39:02) A bear case on the internet(59:52) AI productivity(01:12:10) Stripe + AI(01:13:08) Crypto(01:24:08) Should a16z start a hedge fund?(01:29:51) Big companies(01:35:33) Boards(01:40:27) The Elon method(01:52:59) The future of media