Cheeky Pint
Cheeky PintStripe cofounder John Collison interviews founders, builders, and leaders over a pint.
| Platform |  | Pricing | Only free issues | Publishes | Weekly |
|---|---|---|---|---|---|
| Issues | 25 | Subscribers | Read | cheekypint.substack.com |
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Latest Issues
Recent posts by this newsletter. Browse the email archive.
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 current generation of AI hardware is hitting a wall. They cover the "uncom...
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 payment volume on Stripe grew by a third as our customers continued to pr...
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 Alex Rampell to discuss how Ramp scaled to over $1 billion in revenue...
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 Stratechery and the "1,000 true fans" model, why Taiwan is the most convenie...
Authors
The writers behind this newsletter.
Stripe cofounder John Collison interviews founders, builders, and leaders over a pint.
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