Cheeky Pint
Stripe cofounder John Collison interviews founders, builders, and leaders over a pint.
| Platform |  | Pricing | Only free issues | Publishes | Weekly |
|---|---|---|---|---|---|
| Issues | 34 | Founded | 10 months ago | Last Issue | a month ago |
| Active | |||||
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cheekypint.substack.comLatest Issues
Why the smartphone era is ending, with Evan Spiegel of Snap
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 believes the smartphone has become an isolating legacy device and how tr...
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 the physical world. They cover the harsh economics of the restaurant ind...
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 Turing Test” and why AI has conquered text but still struggles with co...
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 budget, and why 2026 is the year of the supply crunch. They cover the...
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” dynamic, the drama behind their famous 101-billboard campaign, and why sh...
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Stripe cofounder John Collison interviews founders, builders, and leaders over a pint.
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