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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 devel...
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 so...
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 ElevenL...
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 ...
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 wo...
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 ec...
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 ever...
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 wi...
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 w...
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, ...
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!...
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 inter...
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 conten...
In this episode, Elon Musk details his vision for AI's future, arguing that space-based GPUs are essential for scaling due to Earth's energy constraints and regulatory hurdles. He introduces Optimus robots as an "infinite money glitch" that will recursively build more units, and elaborates on XAI's mission to align AI with truth-seeking to ensure humanity's propagation. Musk also shares insights into China's manufacturing dominance and his "nanomanagement" philosophy for tackling engineering bottlenecks like Starship's steel design.
Julia DeWahl, co-founder of Antares, details their mission to develop compact nuclear micro-reactors for defense and critical infrastructure, aiming for enhanced energy resilience. She explains the significant bipartisan shift in nuclear regulation, lessons learned from customer obsession at Opendoor and Starlink, and the economic and strategic advantages of nuclear in a diverse energy future, including efforts to revitalize the domestic nuclear supply chain.
Microsoft CEO Satya Nadella explains the company's AI strategy, focusing on diffusing intelligence within the enterprise by improving data architecture and developing "AI factories." He shares insights on his management style, the importance of developer relations, and the future of user interfaces. Nadella also reflects on lessons from the internet tidal wave and the dot-com bubble, distinguishing the current AI CapEx cycle, and introduces the vision for agentic commerce, where AI enhances discovery and transaction experiences.
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 en...
Zach Abrams (Bridge) and Henri Stern (Privy) discuss the transformative potential of stablecoins, from facilitating cross-border payments and powering neobanks to redefining corporate treasuries. They explore market adoption, the dominance of dollar stablecoins, the role of blockchain advancements, and the impact of regulatory clarity. The conversation also covers the strategic alignment and integration challenges following Bridge and Privy's acquisition by Stripe, envisioning a future where stablecoins become ubiquitous, yet seamlessly integrated, financial infrastructure.
Casey Handmer, founder of Terraform Industries, explains his "solar maximalist" vision where solar energy dramatically reshapes the economy, enabling synthetic natural gas from air and water, and the end of hydrocarbon dependence. He recounts the underappreciated industrialist Henry Kaiser's impact and shares insights into Elon Musk's hard-edged leadership in hardware. The discussion also covers the geopolitics of energy, US manufacturing revival, addressing demographic decline, and his ambitious plan to refill the Salton Sea using solar-powered desalination.
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 pub...
Rivian founder RJ Scaringe explores the immense challenges of starting a car company, from securing billions in capital to developing innovative electric vehicles like the R1 and the upcoming R2. The discussion highlights Rivian's strategic shift to a software-defined zonal architecture, their AI-driven approach to autonomous driving, and the significance of their $5.8 billion deal with Volkswagen, underlining a unique business model beyond just selling cars.
In this episode, Shopify founder Tobi Lütke shares his insights on building one of the internet's foundational companies, emphasizing that companies themselves are a form of technology. He explains how opinionated internal software can profoundly shape an organization's culture and accelerate its evolution, using Shopify's own tools as examples. Lütke also delves into the exciting future of "agentic commerce," where AI acts as a personal shopper, and the critical role of quality products in combating consumerism. The conversation also touches on Shopify's unique partnership with Stripe and Lütke's personal philosophies on entrepreneurship, learning from challenges, and the allure of motor racing.
Marc Andreessen and Charlie Songhurst delve into Silicon Valley's history, discussing the difficulty of identifying market bubbles and the unique, high-trust ecosystem that fosters innovation. They explore the transformative potential of AI, contrasting it with the early internet's limitations, and reflect on the evolution of financial technology, including crypto and stablecoins. The conversation also covers distinct management philosophies, the dynamics of big companies, the future of media, and the profound societal impact of widespread free speech and global communication, all while maintaining a dispositional optimism for technology's future.
Intercom co-founder Des Traynor joins John Collison to explore the company's dual reinvention, culminating in Fin, an AI customer service agent resolving over a million conversations weekly. They delve into the complexities of selling AI in a crowded market, the shift to usage-based billing, and the critical role of product marketing. Traynor also offers insights on effective leadership, co-founder dynamics, and the often-overlooked value of deeply understanding user needs to achieve sustainable growth and avoid common startup pitfalls.
Mackenzie Burnett, CEO of Ambrook, discusses providing financial tools for American farms, emphasizing their unique approach to complex agricultural accounting and payments. She highlights the need for rural resilience and accessible entrepreneurship, touching on labor challenges, the potential of open banking, and the nuances of climate discussions in farming. Burnett also shares her vision for the future of fintech and Stripe's role in it.
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 mat...
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 sch...
Brian Armstrong, Coinbase CEO, joins John Collison to delve into Coinbase's evolution and the broader crypto landscape. They cover the company's strategic choices that led to its market dominance, the challenges of scaling amidst cyber threats, and their proactive approach to security. Armstrong also shares his vision for a future where crypto acts as a primary financial account, tokenizes all asset classes, and influences global economic freedom and political discourse, alongside insights on AI integration.
Robinhood CEO Vlad Tenev discusses his early experiences with hyperinflation and how they influenced his views on stablecoins and global investing. He details Robinhood's disruptive zero-commission model, its evolution into banking, and the complexities of the GameStop saga, including advice from tech leaders. Tenev also outlines his vision for tokenizing private companies, the role of prediction markets, and his approach to leadership and organizational change.
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 applicati...
