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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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The most recent episodes — sign up to get AI-powered summaries of each one.
- 2 days agointerview1h 19m7-min read
The airline CEO putting Starlink on every plane
Scott Kirby, CEO of United Airlines, discusses how counterintuitive bets during the pandemic—like a massive aircraft order and investing in Starlink Wi-Fi—positioned United to dominate a stagnant airline industry. By rejecting expert consensus, embracing technology, and focusing on customer experience through AI and real-time communication, United is creating lasting brand loyalty in a sector long seen as commoditized.
- 1 weeks agointerview1h 11m6-min read
How Toto Wolff built the most valuable team in F1
John Collison and Toto Wolff explore the intricacies of talent identification, team culture, and innovation in Formula 1, drawing parallels between motorsport and tech entrepreneurship. Wolff emphasizes that success in F1 hinges not just on measurable performance but on intangible qualities like resilience, humility, and an almost genetic connection to the car.
- 2 weeks agointerview49 min6-min read
The company building underwater drones for $50,000
Ulysses, co-founded by Will O'Brien, is building a scalable fleet of autonomous underwater robots to transform ocean operations—from seagrass restoration to defense and offshore energy—by drastically reducing costs and enabling persistent, intelligent robotic presence in the world’s oceans. The company’s modular, vertically integrated platform aims to unlock a $10 trillion maritime economy by making underwater work routine, affordable, and scalable.
- 2 weeks agoconversational2h 14m6-min read
Muse Wonder: Zuckerberg and Wang's $100B AI
Meta, led by Mark Zuckerberg and Alexandr Wang, has launched Muse Wonder, a frontier-class AI model designed as a personal and professional superintelligence agent. The model emphasizes multimodal capabilities, active memory, persistence, and domain expertise, with a focus on consumer usability and privacy. Despite massive upfront costs—tens of billions of dollars in compute and infrastructure—Meta believes Muse will be self-sustaining through subscriptions, commerce, and enterprise adoption.
- 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.
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About Cheeky Pint
Stripe cofounder John Collison interviews founders, builders, and leaders over a pint.
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