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Cheeky Pint

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

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Cheeky PintEN · 50 min

The company building underwater drones for $50,000

John CollisonChris SaccaWill O'Brien

Ulysses’ Mako can sell for as little as $50,000 to navies versus roughly $5 million for the common U.S.Navy autonomous underwater vehicle, while Leviathan supports persistent, modular missions.Demand already exceeds manufacturing capacity, with a factory planned next year; slow procurement could become a moat once deployments make undersea monitoring sticky and bankable.

Cheeky PintEN · 81 min

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

John CollisonTony Xu

DoorDash won by proving retention and frequency before buying growth, with product reliability, service recovery, and scarce-capital discipline establishing an “unfair advantage” before acquisition spending accelerated.Its larger opportunity now spans 3–5x incremental restaurant margins, SevenRooms-powered customer identity, and multimodal delivery, but AI interfaces matter only if DoorDash solves inventory, exceptions, and post-checkout reliability end to end.