Jomboy’s $5M Raise Seeks to Expand ‘Fun’ Digital Media Brand

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Jomboy Media recently announced a $5 million raise (details around the valuation were not disclosed). Connect Ventures, an investment partnership between Creative Artists Agency and New Enterprise Associates, led the round. WWE, Reddit co-founder and executive chairman Alexis Ohanian and a collective of professional athletes (including Noah Syndergaard and Karl-Anthony Towns) joined Connect as new investors in the fast growing multimedia company. Founder Jimmy “Jomboy” O’Brien said the company would use the capital to build out its C-suite (including the hire of a CEO) and to add talent. “I want to find up-and-coming talent that we can help build and grow… and we can acquire some big talent [with the money] that helps break down the walls in some other sports” (which will open up new revenue opportunities too).

JWS’ Take: Jomboy Media is a popular brand for baseball content. The company’s YouTube channel has over 1.5 million subscribers, its Twitter handles collectively recorded over 500 million impressions in April, and according to Chartable, Jomboy produces and distributes five of the top 17 baseball podcasts in the U.S. (including top-ranked Talkin’ Baseball).

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Jomboy has built a growing legion of fans by taking a different approach to sports content creation. “We’re not yelling and screaming about opinions that everyone knows we don’t actually hold,” O’Brien said. “That has become a very tired formula, although [it can be] very entertaining at times.”

Instead, the brand treats the game like a game. “There’s a casualness to us, a lack of seriousness that resonates with people,” O’Brien said.

Jomboy’s overarching philosophy is “fun over funny.” O’Brien believes that mentality sets the right tone for the content the brand wants to produce. “We are not comedians. When you try to be funny, it is hard. It puts pressure on you. Sometimes the easiest laugh is to bring someone else down. That is not who we are. It is much less daunting of a task to just have fun.”

Baseball is often criticized for being too slow and boring—the antithesis of fun. O’Brien acknowledges it can be “some of those things.” But he says there are also “intricacies and conversations that are just awesome,” and Jomboy strives to shine a light on them.

O’Brien began creating content for social consumption (think: in-game GIFs, one-minute game recaps) as a hobby during the 2017 MLB season, two years after MLB softened its stance on fan-generated content. Once the “Jomboy” account picked up a bit of traction (~1,000 followers), he added a podcast. Jake Storiale, a college friend, was recruited to co-host.

Following that season, O’Brien was approached with $25,000 and an offer to quit his day job to host Talking Yanks full-time (he was working as an event videographer at the time). He took it and spent the 2018 MLB season “kind of just throwing things at the wall and making content,” he said. “We did all right. We survived.”

O’Brien took on a second $25,000 seed investment at the start of 2019, enabling Storiale to relocate to New York and join Jomboy full time. The duo spent the first half of the ’19 MLB season working tirelessly to produce content and made “no money.” But they put the infrastructure in place that would ultimately allow them to capitalize on a pair of marquee moments later in the season—Yanks manager Aaron Boone’s ejection from a game in which he ranted to the ump that his guys were “savages in the box,” and the discovery of the Astros’ signal-stealing trashcan scam.

“When the ‘savages in the box’ moment came, we knew exactly how to handle it,” O’Brien said. “We had T-shirts out. We had tweets out. We had videos out on all [of the] social media platforms within an hour after it happened… Then when the Astros moment happened, again—same thing.” Jomboy’s reach expanded beyond the Yankees fan base, transcended the internet and made its way to legacy media. O’Brien appeared on ESPN and a host of local sports radio networks in the days that followed.

A number of investors grew interested in backing the burgeoning company. O’Brien and Storiale opted to take $300,000 from a group led by Crypt TV CEO and co-founder Jack Davis, capital they used to get a “shoebox office in the Bronx” and to staff it with five employees.

“Then COVID hit, and we got shut down,” O’Brien said. The company grinded through the lockdown period by expanding into other verticals (think: music, history).

When the abbreviated 2020 MLB season finally began, Jomboy was eager and ready to crank out baseball content again. “Six [one-hour] shows minimum, every day, six days a week,” O’Brien said. The hard work paid off. “We tripled revenue. We tripled the audience. We tripled merch. We tripled everything.”

Pleased with the YoY growth, Davis’ group exercised an option to increase its investment (to $1 million). Jomboy used the additional capital to make more hires during the ’21 season (including former MLB player and investor Trevor Plouffe). The business grew sales to ~$6.5 million last year.

Now armed with another $5 million, 25 new employees and a strategic investor in Connect Ventures, Jomboy is ready for the next step. “[Connect has] the assets and the company building history that could help us in a lot of different [endeavors],” O’Brien said. It is worth noting several CAA athlete clients participated in the most recent round. Davis is the link to Connect Ventures.

Adam Friedman (investor, Connect Ventures) said at the time of the deal that O’Brien’s “ability to become the “people’s voice” is only the beginning, and just a small part of his larger vision for what we all believe Jomboy Media will become.”

Branded content sales made up the bulk of Jomboy’s ’21 revenues. O’Brien believes he can build an equally meaningful merchandise business and plans to hire a “head of e-commerce” to oversee it. The company will look to license more of its content (see: deals with Amazon’s live radio app, Amp and YES Network) and will test the waters on other potential revenue streams (e.g., branded beverages).

It is not a coincidence that the Jomboy Media business plan sounds a lot like the one Barstool employs. O’Brien consumed a lot of Barstool content while in college and took cues from the sometimes controversial sports and pop-culture outlet. “Barstool kind of laid down the map for [digital content companies like ours] to grow … and even Dave [Portnoy] being very transparent behind the scenes of how he did it [was helpful].”

Like Barstool, Jomboy has also started develop its own IP. “We [recently] hosted a Blitzball tournament,” with Chris Rose doing play-by-play and Colorado Rockies reporter Kelsey Wingert doing sidelines. O’Brien called it “a very professional broadcast, in a [crappy] warehouse and a bunch of grown men playing.”

He said it sums up Jomboy’s formula: “The production value should be professional. The content should be amateurish in tone.”

O’Brien can envision hosting floor hockey and mini golf tournaments in the future. “People are buying jerseys of the teams. They are invested. The ceiling on that [IP can be tremendous].”

For those wondering, the Jomboy nickname stems from a typo that took place in a group chat more than a decade ago, after one person’s phone autocorrected Jimmy to Jommy.

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