Jimmy O’Brien’s videos breaking down major events turned Jomboy Media into a big business, but O’Brien still sees himself as a fan. “I don’t plan on changing.”
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Just after 7 one recent morning, Jimmy O’Brien zipped up the elevator to his office in Midtown Manhattan, iced black coffee in hand and one thing in mind: the Rocco Baldelli ejection.
“People are going to be upset if we don’t put that one out first,” O’Brien said.
For the next two and a half hours, he squinted through the early-morning glare in his corner office as Baldelli, the manager of the Minnesota Twins, fumed and fulminated on the two screens in front of him. O’Brien scrutinized every syllable of Baldelli’s interaction with the umpires as if it were crime footage.
Pause. Rewind. Slow motion. Pause. Rewind.
“Oh!” O’Brien shouted.
He exhaled, having cracked the code by reading Baldelli’s lips, and continued: “He says: ‘It’s the rule. They just don’t call it.’”
He typed the sentence into a script he would later narrate. The YouTube video went on to collect more than a million views.
Relative to other manager tirades, Baldelli’s confrontation was decidedly milquetoast — a low-stakes outburst over a close call at home plate in the middle of baseball’s dog days. But O’Brien doesn’t miss many opportunities to entertain — and often enlighten — his growing audience of baseball worshipers. He has built a digital sports media empire on it.
Jomboy Media, a start-up that sprouted from O’Brien’s GIF-laden social media feeds and then grew exponentially because of its coverage of a baseball scandal, has nearly tripled its work force to 64 since 2021. It recently closed a $5 million funding round led by Connect Ventures that included a handful of athletes and celebrities. It is the type of legitimacy that could spoil something born of love, but thus far O’Brien and his company have managed the transition from hobby to big business without getting away from what made them relatable in the first place.
From their bright, white office space — where the walls are adorned with poster board, mock plaques and frog images (a company mascot) — Jomboy employees fill the company’s feeds with sundry sports clips for 1.6 million YouTube subscribers and an additional 900,000 or so followers on Twitter and Instagram. The company’s podcast network now includes nearly two dozen shows. In March, Jomboy signed a partnership with YES Network, which broadcasts Yankees games, to produce content and simulcast shows.
At the center of it all is a sports media personality who never intended to be one. O’Brien, 33, has graying hair, sharp blue eyes, a thick beard and a husky voice fit for sports-talk radio. Except he never had an interest in broadcasting.
“I would never call myself a reporter,” O’Brien said. “I’m still just a biased fan. And I don’t plan on changing.”
O’Brien and Jake Storiale, his best friend and creative partner, co-host a podcast, “Talkin’ Yanks,” that they tape after Yankees games. In August, as the first-place Yankees swooned, the tone of the show became increasingly somber. But they reject comparisons to the rant-filled, take-driven sports commentary on the radio dial.
“I think what we provide are conversations that people feel like they would actually be part of with their buddies,” O’Brien said.
Negativity just isn’t part of the vibe here.
The company’s rise, from friends having fun to full-fledged media outlet, can be traced to a single viral moment. In November 2019, The Athletic broke the story of the Houston Astros’ sophisticated scheme for tipping pitches to their hitters. But, in many ways, it was a video breakdown by O’Brien, in which he read lips and identified other cues in a game between the Astros and the White Sox, that offered fans the first visual evidence of the sign-stealing scandal.
The video took off on social media, catapulting Jomboy’s account into a must-follow for baseball Twitter. O’Brien was three years removed from working full time as a wedding videographer who delivered food in his spare evenings and wondered what he was going to do with his life. He was a year into doing the podcast with Storiale, who worked in marketing for an electrical products conglomerate in Denver.
Suddenly, followers were clamoring for more of O’Brien’s editing artistry. He has since done breakdowns involving cricket, lacrosse, pickleball, “Wheel of Fortune” and Will Smith’s slap of Chris Rock at the Oscars.
As the company has grown, O’Brien and Storiale have kept up the positivity and energy that made them popular in the first place. Their banter adheres to their utmost principle, which O’Brien calls being “fun, not funny.”
“The easiest way to get laughs sometimes is to knock other people down or go negative,” he said. “That isn’t really our vibe.”
This can be construed as an attempt at virtuousness, but he insists it is nothing out of character for them. He and Storiale just generally don’t like confrontation.
“We’ve both been diagnosed as conflict averse because we have older sisters who fought their moms,” O’Brien joked. “We were the peacemakers.”
They call themselves the “clapping company” because they cheer so much for their co-workers. When the team traveled to Los Angeles to film and to network during festivities for this year’s All-Star Game, it rented Airbnbs rather than hotel rooms.
“Twenty of us all stayed together,” said O’Brien, who lives in Bloomfield, N.J., with his wife and 10-month-old son. “We eat meals together. I grew up in a big family. That’s just how I grew up, and that’s what I like. Everyone wakes up at a different time and goes in the kitchen and there’s bagels out. That’s what we do. We’ll see how long we can do it.”
It has so far landed them in the good graces of Major League Baseball and many of its players, including Ian Happ, an outfielder for the Chicago Cubs who hosts a weekly podcast on Jomboy’s network. It has also resulted in plenty of goofy content that is clearly engineered for generating traffic — Storiale wandering around the office asking employees random questions, for instance — rather than sophisticated discourse.
Joe Favorito, a sports industry analyst and lecturer in Columbia University’s sports management program, contrasted Jomboy’s goofier, more inviting approach to the path forged by Barstool Sports, the insurgent media group now worth more than half a billion dollars.
“They’re the less edgy premise of what Barstool is overall,” Favorito said. “They’ve taken that unique, irreverent position while also being respectful of baseball — with some really good insight.”
Jomboy’s escape from the toxicity and polarization on social media is what attracted some big-name investors, including Alexis Ohanian of Reddit and Seven Seven Six, who joined in its latest funding round.
“The pendulum has swung back,” Ohanian wrote in an email. “People crave the good vibes.”
He added: “They’re making the sport of baseball accessible to an entire generation. I think that lands beyond the Yankees fan base. I’d love to see them expand even deeper into other sports.”
Expansion like that would require extra homework for O’Brien, who still selects, edits and narrates the popular “breakdown” videos by himself, at an average of three to four hours per video.
His preternatural ability to read lips is a mystery. There is no deafness in the family. O’Brien says he just has a knack for it.
“When I would watch games with my dad, if a pitcher was coming off a mound yelling and screaming, he would pause it and rewind it and ask me, ‘What did he say, Jim?’” O’Brien said. “And I would tell him.”
Some visual cues are easier to decipher than others. O’Brien, for instance, struggled for hours attempting to pin down a specific phrase screamed by Yankees Manager Aaron Boone when he was ejected for arguing a strike call in July.
“I’m looking at it and I’m like, ‘I’m pretty sure he’s saying, ‘buffer zone,’” O’Brien said. “We Googled it, and there had been a whole article out recently about how M.L.B. umpires get a two-inch buffer zone on the sides of the plate.”
He produced the video, which included an explanation of the buffer zone and why Boone was about to burst a blood vessel arguing about it. It has been viewed 735,000 times.
“He’s a great storyteller,” said Andrew Patterson, the former senior director of new media at MLB Advanced Media who was hired in July as Jomboy Media’s first chief executive. “What he finds aren’t always highlight moments. They’re often the little moments that are overlooked. And he draws out a story that people find compelling.”
Jomboy, which still does not have its own website, has continued to build its large social media presence. Last month, O’Brien cut and posted a video that quickly topped his record for Twitter views (37 million impressions). It was a 58-second highlight of an Oklahoma Little League player comforting the pitcher who had just hit him in the head with a pitch.
O’Brien was riding high that day for another reason. He had received a message from a friend who was close to Baldelli, the Twins’ manager.
“He said Baldelli told me to tell you, ‘You nailed it,’” O’Brien said.