Cheeky Pint

Evan Spiegel, Snap co-founder and CEO, drops into a lively chat about life after smartphones. He explores why AR glasses could make computing feel more human. There is talk of the brutal challenge of building stylish spatial computers, why Snap built its own software stack, and how AI now writes much of the company’s code. The conversation also turns to messaging, teen phone habits, moderation, and Norway’s early Snapchat love.

Tony Xu, DoorDash cofounder and CEO who turned a Stanford project into a delivery giant, talks retention over discounts, brutal restaurant economics, fraud in the physical world, and the near-disaster where refunds ate 40% of remaining cash. He also gets into loyalty, ghost kitchens, why Google stumbled, and Dot, DoorDash’s autonomous robot tackling the last two feet.

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

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 for a lively chat on turning compliance into software at scale. She gets into why startups buy compliance before security, the Dropbox pain that sparked the idea, AI’s collision with audits and questionnaires, the surprisingly effective 101 billboards, and why market sizing can send founders in the wrong direction.

Dmitri Dolgov, Waymo co-CEO and an early Google self-driving engineer, charts the 20-year road from lab experiment to 500,000 rides a week. He gets into why lidar still matters, how Teacher and Critic models train the driving AI, why supervised cars will not simply become robotaxis, and what it takes to scale autonomy across cities.

Luana Lopes Lara, Kalshi co-founder and former MIT math and CS student, joins Tarek Mansour, Kalshi co-founder and CEO behind America’s first federally regulated prediction market. They get into suing the CFTC, explosive growth, election markets, AI traders, insider-trading lines, sports contract ethics, and a future where everything from GPUs to the Oscars gets a price.

Bret Taylor, Sierra cofounder and CEO and chair of the OpenAI board, dives into AI agents, why software may charge for outcomes instead of seats, and why companies miss the real gains by optimizing org charts instead of processes. He also gets into boardroom turbulence, hyper-generalists, and a future where smartphones may fade as agents become the interface.

Garrett Langley, founder and CEO of Flock Safety, builds license-plate-reading cameras, drones, and a public-safety OS. He talks about solving opportunistic crime at scale. Topics include solar-powered cameras, autonomous drones, orchestration with 911, privacy trade-offs, hardware one-way decisions, and how tech helps clear crimes faster.

Reiner Pope, co-founder and CEO of MatX and former Google TPU architect, explains why current AI chips hit a wall and how MatX rethinks memory and numerics. He discusses the latency vs throughput trade-off, combining HBM and SRAM, manufacturing at TSMC scale, and why Rust and mental iteration shape their design approach.