How a Yankees podcast grew into a 60-person media company

Jomboy Media began with a simple premise: build an audience first and figure out the business model later.

In 2017, Jimmy O’Brien was a Yankees fan living in California who wanted more people to talk baseball with. He started building an audience on Twitter, launched the Talkin’ Yanks podcast with his best friend Jake Storiale, and soon received a $20,000 investment from a friend that allowed him to quit his job. Another $20,000 followed when Storiale joined full time. There was no elaborate monetization strategy. As Jomboy Media CEO Courtney Hirsch put it, the bet was that “if they built a community, built an audience, that we would figure out how to make money later.”

That bet worked. What started as a Yankees podcast eventually grew into a sports media company with more than 20 channels, 14 full-time creators, roughly 60 employees, an in-house advertising operation, and an original sports franchise called Warehouse Games. Hirsch, who joined in late 2020 to build the company’s sales operation, has helped oversee much of that transformation. Now Jomboy is entering another phase. It is trying to reduce its dependence on advertising by investing in businesses it can own more completely, from apparel to original sports IP. Along the way, it has developed a playbook for how creator-led companies can scale without abandoning the personalities that made them successful in the first place.

In a recent interview, Hirsch explained why the company now builds around creators rather than individual shows, how Warehouse Games could evolve into a major entertainment franchise built on IP Jomboy owns outright, and why she believes apparel could become one of the company’s biggest businesses.

You can check out the interview on YouTube or subscribe to The Business of Content wherever you get your podcasts. [Apple] [Spotify]

Or you can simply keep scrolling to read the key insights from our discussion.

Let’s jump into it…

Jomboy Media’s first major breakthrough came from something that was initially supposed to be marketing for its podcast.

O’Brien had already built a loyal Yankees following by obsessively participating in the online baseball conversation. He replied to reporters, published postgame recaps after virtually every Yankees game, and maintained a relentless content schedule. “The consistency and the volume of content that he was putting out made it almost impossible for him not to find a Yankee audience,” Hirsch said.

But Twitter and podcasting only took the company so far. After O’Brien began publishing his baseball breakdown videos on YouTube, Jomboy suddenly had a product capable of reaching far beyond New York.

The videos were distinctive because they weren’t merely highlights. O’Brien would slow down footage, lip-read players and managers, explain obscure bits of strategy, and turn small moments into stories. One of his videos helped audiences understand the Houston Astros’ sign-stealing scandal by visually illustrating how the team used banging sounds to communicate pitches. Another famous clip focused on Yankees manager Aaron Boone’s “savages in the box” rant.

Some breakdowns eventually attracted more than a million views apiece. A format that had started as promotion for Talkin’ Yanks became a media franchise of its own.

The importance of that shift went beyond audience size. Jomboy was no longer merely a local Yankees podcast. It was producing baseball content that could travel nationally, which in turn attracted national advertisers like SeatGeek and DraftKings.

At the same time, YouTube and Facebook were still throwing off meaningful programmatic revenue. That money allowed the founders to hire editors and producers without first building a large sales organization. The platforms effectively financed the company’s earliest expansion.

But platform revenue alone wasn’t going to build the business Jomboy wanted to become.