Episodes

What comes after smartphones, with Snap CEO Evan Spiegel

cheeky-pint · Apr 27, 2026 · 1:02:26

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

cheeky-pint · Apr 21, 2026 · 1:20:56

The world of voice AI, with Mati Staniszewski of ElevenLabs

cheeky-pint · Apr 14, 2026 · 1:00:22

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

cheeky-pint · Apr 7, 2026 · 1:09:23

Compliance at scale and why TAM is a distraction with Christina Cacioppo of Vanta

cheeky-pint · Mar 31, 2026 · 57:27

The 20-year journey to fully autonomous cars with Dmitri Dolgov of Waymo

cheeky-pint · Mar 24, 2026 · 1:02:20

Creating prediction markets (and suing the CFTC) with Tarek Mansour and Luana Lopes Lara

cheeky-pint · Mar 17, 2026 · 1:16:30

Bret Taylor of Sierra on AI agents, outcome-based pricing, and the OpenAI board

cheeky-pint · Mar 10, 2026 · 1:41:23

Garrett Langley of Flock Safety on building technology to solve crime

cheeky-pint · Mar 5, 2026 · 1:44:15

Reiner Pope of MatX on accelerating AI with transformer-optimized chips

cheeky-pint · Feb 26, 2026 · 1:13:07

Stripe’s 2025 annual letter

cheeky-pint · Feb 24, 2026 · 27:44

Ramp founder Eric Glyman on the many ways AI is changing corporate spending

cheeky-pint · Feb 17, 2026 · 1:11:10

Ben Thompson from Stratechery on AI ads, the end of SaaS, and the future of media

cheeky-pint · Feb 12, 2026 · 1:30:15

Elon Musk on Space GPUs, AI, Optimus, and his manufacturing method

cheeky-pint · Feb 5, 2026 · 2:46:02

Julia DeWahl of Antares on building nuclear reactors for the US military

cheeky-pint · Nov 25, 2025 · 45:17

Satya Nadella describes how lessons from Microsoft’s history apply to today’s boom

cheeky-pint · Nov 18, 2025 · 1:18:51

Dave Ricks, CEO of Eli Lilly, on GLP-1s and the business of pharma

cheeky-pint · Nov 11, 2025 · 2:05:15

Stablecoin special: Zach Abrams (Bridge) and Henri Stern (Privy)

cheeky-pint · Nov 4, 2025 · 1:14:09

Casey Handmer of Terraform Industries on solar maximalism, hard tech, and reclaiming the Salton Sea

cheeky-pint · Oct 28, 2025 · 1:16:07

Dan Sundheim of D1 Capital on the art of public market investing

cheeky-pint · Oct 22, 2025 · 1:38:08

How to build a $16B car company with RJ Scaringe, founder of Rivian

cheeky-pint · Oct 14, 2025 · 1:08:48

Tobi Lütke is still captivated by internet commerce, 20 years later

cheeky-pint · Oct 6, 2025 · 1:42:55

Marc Andreessen and Charlie Songhurst on the past, present, and future of Silicon Valley

cheeky-pint · Oct 1, 2025 · 2:07:56

Des Traynor on reinventing Intercom twice and the “four horsemen” of good AI companies

cheeky-pint · Sep 24, 2025 · 1:18:20

Ambrook CEO Mackenzie Burnett on American agriculture, rural resilience, and carrying 50lbs of fresh pork on Amtrak

cheeky-pint · Sep 17, 2025 · 54:53

Zipline CEO Keller Cliffton on air-dropping blood to Rwandan hospitals and getting to 50,000 aircraft per year

cheeky-pint · Sep 10, 2025 · 1:14:12

Cognition CEO Scott Wu on acquiring Windsurf, AI replacing engineers, and the Moneyball-ification of everything

cheeky-pint · Aug 27, 2025 · 57:53

Coinbase CEO Brian Armstrong on bitcoin going to $1 million, electing a pro-crypto Congress, and Jamie Dimon

cheeky-pint · Aug 20, 2025 · 1:16:31

Robinhood CEO Vlad Tenev on tokenizing private companies, changing the SEC, and Frank Slootman

cheeky-pint · Aug 13, 2025 · 1:05:50

Anthropic CEO Dario Amodei on designing AGI-pilled products, model economics, and 19th-century vitalism

cheeky-pint · Aug 6, 2025 · 1:02:51

Serial entrepreneur Pieter Levels on building in public and living as a digital nomad

cheeky-pint · Jul 9, 2025 · 22:37

The Bot Company founder and CEO Kyle Vogt on home robots and why he’ll never sell another company

cheeky-pint · Jun 25, 2025 · 22:31

OpenAI cofounder Greg Brockman on the scaling hypothesis and refactoring as a killer AI use case

cheeky-pint · Jun 18, 2025 · 31:51

Meta CFO Susan Li on headcount vs. GPU allocation, “free cash flow” hats, and almost becoming a PM

cheeky-pint · Jun 18, 2025 · 29:43

Cheeky Pint hosted by Stripe cofounder John Collison

cheeky-pint · Jun 16, 2025 · 0:56