BAY AREA — Jomboy Media, the sports media company founded by Jimmy O'Brien, appointed his sister Courtney Hirsch as its chief executive officer in March 2025. Hirsch had previously served as the company's chief operating officer after joining in 2020.

O'Brien, a New York Yankees fan who grew up in suburban Connecticut, built the company from informal video projects into a 60-employee operation. He got his first camera in seventh or eighth grade during the heyday of reality-TV shows such as MTV's "The Real World" and "Jackass." O'Brien's mother, who was from the Bronx, suggested he use a pseudonym for his social-media handle, and he chose "Jomboy," an autocorrect of "Jimmy."

After attending several colleges while working various gig jobs, O'Brien lived in the Bay Area, where he worked as a wedding videographer and lived with his girlfriend, now his wife. In 2017, he started the podcast "Talkin' Yanks" with his friend Jake Storiale and began making short videos about Yankees-related episodes, including a brawl with the Detroit Tigers and a team photo showing players with their thumbs down.

In 2019, O'Brien posted a video breaking down Yankees manager Aaron Boone's rant at an umpire by lip-reading and captioning it. The video went viral and led to T-shirts quoting the tirade being sold on the "Talkin' Yanks" website. A few months later, he posted a video breaking down the Houston Astros' sign-stealing scheme by highlighting the sound of a banging trash can, which was viewed by millions.

O'Brien's "breakdowns" of hot-mike moments, ejections, and other high-emotion events became a hallmark of Jomboy Media content. He has built his career around covering people losing composure on the field. "The subjects of my videos seem to get a kick out of it," O'Brien said.

O'Brien refrains from posting videos if lip-reading reveals content that could genuinely get the subject in trouble. He recently halted production of merchandise quoting a remark by an injured Yankees catcher that was part of a longer, somber statement. "I think if I had started younger, it's probably easier to try and be angsty or edgy," he said.

Major League Baseball had a strict copyright policy and sent O'Brien letters requiring the removal of non-licensed video content. Other professional sports leagues, particularly the NBA, were making cultural inroads with young audiences in ways MLB was not. The league began to recognize that influencers like O'Brien were attracting the young followers it wanted, and last year MLB bought a minority stake in Jomboy Media for an undisclosed sum as part of efforts to generate new fans.

O'Brien says baseball's pacing is part of its appeal. "I like baseball because it's slow," he said. "The secret is that Americans like slow sports."

Hirsch, who had worked as an ad-sales executive at Uber before joining her brother's company, agreed to help only if she could be fully committed. "I'm a very all-or-nothing person," Hirsch said. The company now has 60 employees, including O'Brien and his youngest brother, Luke.

Jomboy Media is projecting revenues to surpass $20 million this year, double its revenue from two years ago. Increasing numbers of people, including those who do not consider themselves baseball fans, consume the company's content.