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Cheeky Pint

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

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Cheeky PintEN · 62 min

What comes after smartphones, with Evan Spiegel of Snap

John CollisonEvan Spiegel

Snap enters 2026 near 1 billion monthly active users and net-income profitability, with consumer Specs launching after 12 years of investment to pair normal-glasses wearability with spatial-computer capabilities.With over two-thirds of new code AI-written, 25 million Snapchat+ subscribers, and direct revenue above $1 billion, cheaper software may increase the value of Snap’s distribution and proprietary hardware.

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.