Cheeky Pint

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.

A rapid readthrough of Stripe’s 2025 annual letter covering big shifts in the internet economy. Topics include how market sorting is creating runaway winners and a faster, higher-performing startup cohort. Discussion of global-by-default businesses, stablecoins entering real-world payments, a payments-focused blockchain called Tempo, and five levels of agentic commerce.

Eric Glyman, cofounder and CEO of Ramp, the finance automation platform powering corporate spend. He talks about scaling Ramp to billion-dollar revenue, how AI agents review huge volumes of expenses with high accuracy, the changing nature of bill pay and procurement, and why the company believes fintech will pivot to selling time rather than money.

Ben Thompson, founder of Stratechery and leading tech analyst, shares big-picture takes on aggregation, ads as a societal good, and why TikTok’s algorithm is the core national-security worry. He explores AI’s role as a new aggregator, looming chip-supply risks around 2029, and how agentic commerce and ad models may evolve.

Elon Musk, CEO of SpaceX and Tesla and serial tech entrepreneur, joins for a wide‑ranging pub conversation. He talks about moving massive AI compute to space, servicing GPUs in orbit, solar and launch scale for terawatt compute. He also discusses Optimus humanoid robots, mass manufacturing choices, and the engineering tradeoffs behind Starship and lunar industrial plans.

Julia DeWahl, cofounder of Antares, is revolutionizing energy with her vision for small nuclear micro-reactors tailored for military resilience. She discusses the nuclear renaissance fueled by AI hyperscalers and the need for regulatory reform. Julia emphasizes the shift towards 24/7 carbon-free power, highlighting the importance of nuclear alongside solar. Drawing from her experiences at SpaceX and Opendoor, she shares insights on customer obsession and the future of energy procurement. Discover why the nuclear vibe is changing!