Tyler and Jake are live in Louisville, Kentucky for the 152nd Kentucky Derby — and before the gates open, they're breaking down everything that makes this two-minute race a week-long American institution.

From the fascinating origins of Churchill Downs and the "Run for the Roses" tradition to the mechanics of pari-mutuel betting and $5,000 mint julep cups, this episode covers the history, culture, and business of one of the most iconic events in sports. Whether you're a die-hard racing fan or just showing up for the hats, this is your ultimate Derby primer.

⏱️ Timestamps

00:00 — Intro

00:33 — Why this episode is different

02:23 — Kentucky Derby history: Founded in 1875, Lewis & Clark connections, early Black jockeys

04:44 — The race format: Three-year-olds only, 1.25 miles, first Saturday in May

07:23 — The "Run for the Roses": Origin of the rose tradition & the Kroger garland

09:59 — Mint Juleps: History, the "too much ice" debate & $5,000 Woodford Reserve cups

16:44 — The Twin Spires: How a 24-year-old architect accidentally created an icon

19:18 — The hats, fashion & Kentucky Derby as a high-society tradition

25:37 — Betting 101: Pari-mutuel wagering, $349M wagered, post position superstitions

32:44 — Jake's Derby side quests: Petting a horse, bourbon ice cream & the hot brown

39:01 — The social media strategy behind the Derby & influencer marketing

48:10 — What Tyler & Jake are actually doing on the social team all week

50:34 — Derby Week schedule: From Opening Day to the 6:57pm post on Saturday

55:18 — Outro