Cheeky Pint artwork

Technology · Stripe

Cheeky Pint

by Stripe

Stripe cofounder John Collison interviews founders, builders, and leaders over a pint.

Chart trend

Position in the Technology chart (US), last 90 days.

#7
all-time peak
2
days in the top 10 since Aug 2025

Latest episodes

Showing 20 · updated from the feed

What comes after smartphones, with Snap CEO Evan Spiegel

Snap CEO Evan Spiegel joins John at the pub for a deep dive into Snap's "crucible moment" of 2026: the long-awaited consumer launch of Spectacles. Evan explains why he be

Apr 27
1 h 02 min

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

Tony Xu, cofounder and CEO of DoorDash, joins John for a pint to discuss how they won a crowded market by obsessing over retention and the reality of fighting fraud in th

Apr 21
1 h 20 min

The world of voice AI, with Mati Staniszewski of ElevenLabs

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

Apr 14
1 h 00 min

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

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

Apr 7
1 h 09 min

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

Christina Cacioppo, founder and CEO of Vanta, joins the pub to discuss building the future of agentic trust. She explains why compliance has a “vitamin vs painkiller” dyn

Mar 31
57 min

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

Waymo is now doing nearly 500,000 rides a week across 10 cities. Co-CEO Dmitri Dolgov came to the pub to discuss how they moved from scientific research to massive global

Mar 24
1 h 02 min

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

Tarek Mansour and Luana Lopes Lara are the co-founders of Kalshi, the first federally regulated prediction market in the US. They sit down with John and Matt Huang to dis

Mar 17
1 h 16 min

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

Bret Taylor, co-founder of Sierra and Chair of the OpenAI board, joins John for a pint to discuss the rapid shift toward an agentic future. In this episode, Bret explains

Mar 10
1 h 41 min

Garrett Langley of Flock Safety on building technology to solve crime

Garrett Langley is the founder and CEO of Flock Safety, a public safety operating system that helps communities and law enforcement eliminate crime. He sits down with Joh

Mar 5
1 h 44 min

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

Reiner Pope is the co-founder and CEO of MatX, designing specialized chips for Large Language Models. A former Google TPU architect, he joins John to discuss why the curr

Feb 26
1 h 13 min

Stripe’s 2025 annual letter

The internet economy accelerated in 2025. The fastest-growing companies got even faster, agentic commerce and stablecoin payments started to kick into gear, and total pay

Feb 24
27 min

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

Eric Glyman is the cofounder and CEO of Ramp, the finance automation platform that now powers over 2% of all corporate spend in the US. He sits down with John and co-host

Feb 17
1 h 11 min

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

Ben Thompson, the internet’s premier tech analyst, joins John for a wide-ranging conversation on the mechanics of the internet economy. They discuss the origins of Strate

Feb 12
1 h 30 min

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

John Collison and Dwarkesh Patel sit down with Elon Musk to discuss why the future of AI isn’t on Earth, but in the "always sunny" vacuum of space. Between pints, they di

Feb 5
2 h 46 min

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

Julia DeWahl is the cofounder of Antares, a company developing nuclear micro-reactors for the US military and critical infrastructure. She sits down with John to discuss

Nov 25 2025
45 min

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

Satya Nadella, CEO of Microsoft, sits down with John to discuss the diffusion of AI inside the enterprise. He explains why “all your data at your fingertips” is the everg

Nov 18 2025
1 h 18 min

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

Dave Ricks, the CEO of Eli Lilly, the world's most valuable pharmaceutical company, sits down with John and Patrick to discuss the complex business of drug development. D

Nov 11 2025
2 h 05 min

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

Zach Abrams, the CEO and cofounder of Bridge, the leading stablecoin orchestration platform, and Henri Stern, CEO and cofounder of Privy, the leading crypto wallet infras

Nov 4 2025
1 h 14 min

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

Description Casey Handmer is the founder of Terraform Industries, who is developing a machine that makes synthetic natural gas from sunlight and air. He joins the podcas

Oct 28 2025
1 h 16 min

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

Seasoned public and private investor Dan Sundheim sits down with John to discuss the harrowing GameStop short squeeze, waking up at 3am for the European market open, and

Oct 22 2025
1 h 38 min

Chart positions

Where Cheeky Pint ranks today in each Apple Podcasts chart (US, Sep 4, 2026).

#167 ▲ 14 Technology US

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