Cheeky Pint

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.

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.