Inside the growing sports media empire where the business is all fun and games

With Jomboy Media, the baseball-loving hosts of the Talkin’ Yanks podcast have created the un-Barstool Sports—a fun-loving sports media company that’s playing by its own rules.

September is always a big month for Jomboy Media. Baseball is the six-year-old sports content company’s meat and potatoes, and September is when Major League Baseball’s playoff push accelerates from foot race to sprint. Jimmy “Jomboy” O’Brien and Jake Storiale, best friends since high school in suburban Connecticut, launched the company in 2018 with a New York Yankees–focused podcast called Talkin’ Yanks. Since then, the company’s programming lineup has swollen to 44 podcasts and 20 YouTube channels covering multiple sports in multiple cities, often cohosted by former pro athletes, but all of its top performers are baseball-themed—a modern, forward-thinking media company propelled, incongruously, by the starchiest of pro sports. And the cornerstone of Jomboy’s business—the gateway drug to the Jomboy universe and its band of merry sports junkies—is O’Brien’s trademark YouTube creation, “The Breakdown,” a recurring series in which he applies his uncanny gift for lip-reading and the film-production chops he honed as a former wedding videographer to piece together code-cracking reconstructions of viral on-field incidents, fights, ejections, and dramatic twists of fate.