When Checkmate passed Instagram to hit #1 on the App Store (above ChatGPT, on $0 in ad spend, built by a team of five), co-founder and CTO Rory Garton-Smith was on vacation in Fiji. His honest reaction: "I felt sick."

Here's the part that doesn't compute. Before tech, Rory Garton-Smith was a Sony-signed producer and DJ under the name Elk Road. He put a Britney Spears remix of "Toxic" on SoundCloud that went viral overnight, and Britney Spears' management messaged him just to say "We like this." He once had to follow the Jack U set from Skrillex and Diplo, told not to touch the CDJ for a six-minute outro he still calls "the longest six minutes of his life." He also traded oil futures off the shadows in satellite images of oil tanks, taught himself to code, and cold-DM'd his way into a job at Apple.

Now Paris Hilton is personally on his cap table and The Chainsmokers help him recruit engineers away from Meta. We also get the real NYC texture: Rao's ("you need to know a crime family"), Cafe Cluny, the Erewhon status tax, and Noriel's Shabbat, before Rory Garton-Smith answers the one question we ask everyone: who's the coolest person you know?