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Cheeky Pint

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

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Why the smartphone era is ending, with Evan Spiegel of Snap
April 27th, 2026•cheekypint.substack.com
The economics and trends of the restaurant industry, with Tony Xu of DoorDash
April 21st, 2026•cheekypint.substack.com
The world of voice AI, with Mati Staniszewski of ElevenLabs
April 14th, 2026•cheekypint.substack.com
The history and future of AI at Google, with Sundar Pichai
April 7th, 2026•cheekypint.substack.com
Compliance at scale and why TAM is a distraction with Christina Cacioppo of Vanta
March 31st, 2026•cheekypint.substack.com
The 20-year journey to fully autonomous cars with Dmitri Dolgov of Waymo
March 24th, 2026•cheekypint.substack.com
Creating prediction markets (and suing the CFTC) with Tarek Mansour and Luana Lopes Lara
March 17th, 2026•cheekypint.substack.com
Bret Taylor of Sierra on AI agents, outcome-based pricing, and the OpenAI board
March 10th, 2026•cheekypint.substack.com
Garrett Langley of Flock Safety on building technology to solve crime
March 5th, 2026•cheekypint.substack.com
Reiner Pope of MatX on accelerating AI with transformer-optimized chips
February 26th, 2026•cheekypint.substack.com
Stripe’s 2025 annual letter
February 24th, 2026•cheekypint.substack.com
Ramp founder Eric Glyman on the many ways AI is changing corporate spending
February 17th, 2026•cheekypint.substack.com
Ben Thompson from Stratechery on AI ads, the end of SaaS, and the future of media
February 12th, 2026•cheekypint.substack.com
Elon Musk on Space GPUs, AI, Optimus, and his manufacturing method
February 5th, 2026•cheekypint.substack.com
Julia DeWahl of Antares on building nuclear reactors for the US military
November 25th, 2025•cheekypint.substack.com
Satya Nadella describes how lessons from Microsoft’s history apply to today’s boom
November 18th, 2025•cheekypint.substack.com
Dave Ricks, CEO of Eli Lilly, on GLP-1s and the business of pharma
November 11th, 2025•cheekypint.substack.com
Stablecoin special: Zach Abrams (Bridge) and Henri Stern (Privy)
November 4th, 2025•cheekypint.substack.com
Casey Handmer of Terraform Industries on solar maximalism, hard tech, and reclaiming the Salton Sea
October 28th, 2025•cheekypint.substack.com
Dan Sundheim of D1 Capital on the art of public market investing
October 22nd, 2025•cheekypint.substack.com