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

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...