
Stripe cofounder John Collison interviews founders, builders, and leaders over a pint.
| Publishes | Weekly | Episodes | 31 | Founded | 10 months ago |
|---|---|---|---|---|---|
| Number of Listeners | Categories | BusinessEntrepreneurshipTechnology | |||

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” dynamic, the drama behind their famous 101-billboard campaign, and why she believes... more
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 scaling. He gives a masterclass on the sensor stack (and why you still need Lid... more
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 discuss growing their revenue 11x in six months, why they sued their own regulator ... more
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 why outcome-based pricing is the future of software business models, and why he... more
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Loved the pod but questions, discussion points and views are pretty repetitive.
He should start a payments company or something; seems very knowledgeable
I love this show, but the transition sound to commercial sounds just like the Doppler effect of a car horn speeding towards you. It gives me a heart attack every time. Users first.
Great show
Why do you have to add Stripe cofounder for your identity here?
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Apple Podcasts | #232 |
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A candid, tech-forward interview series where founders, builders, and leaders share practical insights from starting up to scaling, often touching on regulatory, governance, and market-shaping implications. Conversations span prediction markets, AI governance, safety tech, energy innovation, and financial infrastructure, with a common thread of translating complex technologies into real-world impact. Listeners can expect thoughtful questions, problem-solving mindset, and relatable founder journeys, all anchored by a casual, conversational vibe over a pint. A standout hallmark is exploring high-stakes tradeoffs between regulation, growth, and responsible innovation across diverse industries, making it useful for executives, product/tech lead... more
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Cheeky Pint launched 10 months ago and published 31 episodes to date. You can find more information about this podcast including rankings, audience demographics and engagement in our podcast database.
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Recent guests on Cheeky Pint include:
1. Tarek Mansour
2. Luana Lara
3. Bret Taylor
4. Garrett Langley
5. Zach Abrams
6. Henri Stern
7. Casey Handmer
8. Mackenzie Burnett
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