Cheeky Pint

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 (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

The economics and trends of the restaurant industry, with Tony Xu of DoorDash

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

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 (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

The history and future of AI at Google, with Sundar Pichai

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

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 (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