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Cheeky Pint: Daily Summaries Delivered
by Stripe
Stripe cofounder John Collison interviews founders, builders, and leaders over a pint.
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- Apr 27, 20261h 2m
What comes after smartphones, with Snap CEO Evan Spiegel
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 Snap’s crucible moment Specs AR as the right form factor Stablecoin payouts on Stripe Monetizing the camera Social media vs messaging Content moderation Snap’s evolution
- Apr 21, 2026interview1h 20m5-min read
The economics and trends of the restaurant industry, with Tony Xu of DoorDash
DoorDash's success stemmed from an obsessive focus on product quality, retention, and solving the full logistics stack early, rather than relying on capital to win. CEO Tony Xu attributes their dominance to getting the complex, multivariate experience—selection, speed, cost, reliability, and customer service—right when they had no money to spend on growth.
- Apr 14, 20261h 0m
The world of voice AI, with Mati Staniszewski of ElevenLabs
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 How audio models work ElevenLabs business model The conversational Turing Test Link by Stripe Cascaded vs speech-to-speech Universal translation Designing an AI-native org
- Apr 7, 2026interview1h 9m6-min read
The history and future of AI at Google, with Sundar Pichai
Sundar Pichai reflects on Google's decade-long AI leadership, emphasizing that Transformers were developed with product intent, not pure research, and that Google’s vertical integration across AI infrastructure, models, and applications positions it uniquely in the current AI race. Despite early missteps in productizing AI, Google is now accelerating through compute constraints, agentic workflows, and long-term bets like robotics, quantum, and even space-based data centers.
- Mar 31, 202657 min
Compliance at scale and why TAM is a distraction with Christina Cacioppo of Vanta
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 Vanta How compliance works Breaches Stripe Tax AI and compliance Go-to-market Lessons from USV
- Mar 24, 20261h 2m
The 20-year journey to fully autonomous cars with Dmitri Dolgov of Waymo
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 Russia Waymo architecture Why now? Driving nuance Stripe Agentic Commerce Suite Hardware Emergent behavior Scaling Google Article: EMMA: End-to-End Multimodal Model for Autonomous Driving – Waymo Research: https://waymo.com/research/emma/
- Mar 17, 20261h 16m
Creating prediction markets (and suing the CFTC) with Tarek Mansour and Luana Lopes Lara
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 Suing the government Why now? Kalshi by numbers Solving market making Agentic trading Sharps Stripe Connect Evolving Kalshi Who loses from Kalshi? Insider trading The ethics of sports contracts New derivatives Politics Article(s): On the Observational Implications of Knightian Uncertainty – Kevin Hassett & Weifeng Zhong (AEI) The 2028 Global Intelligence Crisis – Citrini Research
- Mar 10, 20261h 41m
Bret Taylor of Sierra on AI agents, outcome-based pricing, and the OpenAI board
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 Coding Sierra Agentic UX Building support agents Co-developing with the models SaaSpocalypse Stripe Sessions Outcome-based pricing Is Sierra short AGI? AI productivity How to structure a tech business Board drama AI predictions
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About Cheeky Pint
Stripe cofounder John Collison interviews founders, builders, and leaders over a pint.
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