Podcast · 35 episodes
Cheeky Pint
by Stripe · English
Stripe cofounder John Collison interviews founders, builders, and leaders over a pint.
Latest episodes
What comes after smartphones, with Snap CEO Evan SpiegelSnap’s “crucible moment” heading into late 2025/2026—approaching 1B monthly active users, net income profitability, heavy AI-driven software changes, and the consumer rollout of Snap’s specs glasses…27 Apr 2026 · 1 h 2 min
The economics and trends of the restaurant industry, with Tony Xu of DoorDashDoorDash CEO Tony Xu discusses what drives restaurant delivery economics and broader restaurant industry trends, comparing the U.S.21 Apr 2026 · 1 h 21 min
The world of voice AI, with Mati Staniszewski of ElevenLabsThe episode explains how voice AI works and how ElevenLabs builds and deploys it, from audio model representations (phonemes, spectrograms, waveform) to text-to-speech, speech-to-text, and voice…14 Apr 2026 · 1 h
All episodes
What comes after smartphones, with Snap CEO Evan SpiegelSnap’s “crucible moment” heading into late 2025/2026—approaching 1B monthly active users, net income profitability, heavy AI-driven software changes, and the consumer rollout of Snap’s specs glasses…27 Apr 2026 · 1 h 2 min · 34 chapters
The economics and trends of the restaurant industry, with Tony Xu of DoorDashDoorDash CEO Tony Xu discusses what drives restaurant delivery economics and broader restaurant industry trends, comparing the U.S.21 Apr 2026 · 1 h 21 min · 32 chapters
The world of voice AI, with Mati Staniszewski of ElevenLabsThe episode explains how voice AI works and how ElevenLabs builds and deploys it, from audio model representations (phonemes, spectrograms, waveform) to text-to-speech, speech-to-text, and voice…14 Apr 2026 · 1 h · 29 chapters
The history and future of AI at Google, with Sundar PichaiSundar Pichai discusses Google’s AI history and productization path, the future of search as it evolves toward agentic task completion, and the real-world constraints shaping AI investment (TPUs,…7 Apr 2026 · 1 h 9 min · 29 chapters
Compliance at scale and why TAM is a distraction with Christina Cacioppo of VantaChristina Cacioppo (Vanta) explains why “compliance” is the buying moment for startups, how Vanta automates SOC 2/ISO 27001-style trust management, and how AI is shifting compliance from manual prep…31 Mar 2026 · 57 min · 34 chapters
The 20-year journey to fully autonomous cars with Dmitri Dolgov of WaymoDmitri Dolgov, Co-CEO of Waymo24 Mar 2026 · 1 h 2 min · 26 chapters
Creating prediction markets (and suing the CFTC) with Tarek Mansour and Luana Lopes LaraIn this episode, Tarek Mansour and Luana Lopes Lara, co-founders of Kalshi, discuss the intricacies of running the first federally regulated prediction market in the US.17 Mar 2026 · 1 h 17 min · 34 chapters
Bret Taylor of Sierra on AI agents, outcome-based pricing, and the OpenAI boardIn this engaging episode, Bret Taylor shares his insights on the evolving landscape of AI, the future of software business models, and his experiences on the boards of OpenAI and Twitter.10 Mar 2026 · 1 h 41 min · 39 chapters
Garrett Langley of Flock Safety on building technology to solve crimeIn this episode of Cheeky Pint, John Collison interviews Garrett Langley, founder and CEO of Flock Safety, a public safety operating system aimed at helping communities and law enforcement eliminate…5 Mar 2026 · 1 h 44 min · 14 chapters
Reiner Pope of MatX on accelerating AI with transformer-optimized chipsCo-founder and CEO of MatX, former Google TPU architect26 Feb 2026 · 1 h 13 min · 35 chapters
Stripe’s 2025 annual letterIn this episode of the Cheeky Pint podcast, John Collison, cofounder of Stripe, reads Stripe's Annual Letter for 2025, discussing the accelerated growth of the internet economy, advancements in…24 Feb 2026 · 28 min · 10 chapters
Ramp founder Eric Glyman on the many ways AI is changing corporate spendingIn this episode, Eric Glyman, CEO of Ramp, discusses the rapid growth and innovative approaches of his company, which has become a key player in finance automation for corporate spending.17 Feb 2026 · 1 h 11 min · 27 chapters
Ben Thompson from Stratechery on AI ads, the end of SaaS, and the future of mediaIn this episode of *Cheeky Pint*, John Collison interviews Ben Thompson, founder and author of Stratechery.12 Feb 2026 · 1 h 30 min · 46 chapters
Elon Musk on Space GPUs, AI, Optimus, and his manufacturing methodElon Musk on Space GPUs, AI, Optimus, and his manufacturing method5 Feb 2026 · 2 h 46 min · 77 chapters
Julia DeWahl of Antares on building nuclear reactors for the US militaryJulia DeWahl, Co-founder of Antares25 Nov 2025 · 45 min
Satya Nadella describes how lessons from Microsoft’s history apply to today’s boomIn this episode, John Collison interviews Satya Nadella, the CEO of Microsoft, discussing a range of topics including the integration of AI in enterprises, the significance of data accessibility, and…18 Nov 2025 · 1 h 19 min
Dave Ricks, CEO of Eli Lilly, on GLP-1s and the business of pharmaIn this episode, John Collison interviews Dave Ricks, the CEO of Eli Lilly, the world's most valuable pharmaceutical company.11 Nov 2025 · 2 h 5 min
Stablecoin special: Zach Abrams (Bridge) and Henri Stern (Privy)In this episode of *Cheeky Pint*, John Collison, co-founder of Stripe, interviews Zach Abrams, CEO and co-founder of Bridge, and Henri Stern, CEO and co-founder of Privy.4 Nov 2025 · 1 h 14 min
Casey Handmer of Terraform Industries on solar maximalism, hard tech, and reclaiming the Salton SeaCasey Handmer of Terraform Industries on solar maximalism, hard tech, and reclaiming the Salton Sea28 Oct 2025 · 1 h 16 min
Dan Sundheim of D1 Capital on the art of public market investingIn this episode, John Collison interviews Dan Sundheim, founder of D1 Capital, a prominent hedge fund manager known for his expertise in public market investing.22 Oct 2025 · 1 h 38 min
How to build a $16B car company with RJ Scaringe, founder of RivianIn this episode of Cheeky Pint, John Collison interviews RJ Scaringe, the founder and CEO of Rivian, discussing the intricate journey of building a successful electric vehicle (EV) company from the…14 Oct 2025 · 1 h 9 min
Tobi Lütke is still captivated by internet commerce, 20 years laterIn this episode of *Cheeky Pint*, John Collison interviews Tobi Lütke, the founder and CEO of Shopify.6 Oct 2025 · 1 h 43 min
Marc Andreessen and Charlie Songhurst on the past, present, and future of Silicon ValleyMarc Andreessen and Charlie Songhurst on the past, present, and future of Silicon Valley1 Oct 2025 · 2 h 8 min
Des Traynor on reinventing Intercom twice and the “four horsemen” of good AI companiesDes Traynor, Co-founder of Intercom24 Sep 2025 · 1 h 18 min