Jimmy “Jomboy” O’Brien won’t be watching his beloved New York Yankees in the World Series this year.
But he will be watching every pitch of the Dodgers-Blue Jays matchup, anyway, from a studio at his media company’s office in midtown Manhattan, where O’Brien has built a sleek new media venture alongside his best friend, streaming partner and co-founder, Jake Storiale.
That’s where Jomboy and Storiale, along with a bunch of other baseball-obsessed creators, churn out a ton of YouTube content, which is the foundation for the Jomboy Media empire.
The office, which is home to most of the company’s 54 employees, has the vibe of a very well-funded college newspaper: young faces, lots of movement, games streaming on multiple TVs, and a designated spot for visitors to show off their pitching skills.
From live streaming games to pre and post-game shows to “Talkin’ Baseball,” the daily news and analysis show Storiale co-hosts alongside former MLB player Trevor Plouffe, the company has whatever fix hardball fans are looking for.
Not to mention what they are best known for — O’Brien’s video breakdowns, where he uses his innate lipreading skills to give fans an idea of what players are saying on the field or during a brawl.
“Yeah I’m good! Yeah! Let’s go!” Jomboy told viewers, as he read the lips of Toronto Blue Jays pitcher Max Scherzer yelling at his coach on the mound when he went to take him out of the game last week.
O’Brien and Storiale have come a long way from Lavallete, N.J., where O’Brien started streaming about baseball in 2017. Now, Jomboy Media has 2.2 million subscribers on YouTube, and another 723,300 followers on TikTok.
The two mid-30s uber-fans have had plenty of help along the way from O’Brien’s sister, Courtney Hirsch, who was named Jomboy Media CEO earlier this year. She joined her brother’s budding operation in late 2020 after leaving a high-ranking advertising job at Uber.
Since then, Jomboy Media has struck a number of key sponsorship deals, including with DraftKings, and raised more than $6 million from investors, including ex-players like Plouffe, stars like Christian Yelich, and actor Patrick Schwarzenegger.
And their biggest deal to date came in June, when Major League Baseball acquired a stake in Jomboy Media for an undisclosed sum.
O’Brien and Hirsch, in an interview with TheWrap, said the deal has not changed one thing about their company’s irreverent-but-lighthearted approach to talking about the sport they love.
“For us, nothing really changed about what we’re doing, except we get more access and support from the league itself,” Hirsch said. “They want us to keep doing what we’re doing.”
O’Brien added: “If we have opinions, we’re going to share them.”
And that is his specialty. O’Brien and Storiale provide the fan’s eye view Jomboy is founded on, while Hirsch handles the heavy lifting on the business side.
TheWrap talked to O’Brien and Hirsch about running a media business together, O’Brien’s lip reading skills, their new MLB deal, and what advice O’Brien would share with upstart YouTubers. The following is an interview edited for clarity and brevity.
First off — what’s the dynamic like working with your sibling? And can you tell me about the process of coming aboard a few years ago and then moving up to CEO earlier this year?
Courtney Hirsch: My background is in media and ad sales — and we never, ever, ever thought we would work together. But when Jimmy and Jake were building this, they were really focused on content, and then, back in 2020, I think was the first time they started to think about monetization and building a team.
So my skill set just naturally made sense, because the fastest, quickest way to monetize was through advertising sales. At that point, we talked to our parents about ‘Should I do it?” [Laughs]
Yeah, was there any trepidation on the other side, simply about mixing business and family?
Hirsch: No, it’s going fine.
Jimmy O’Brien: I would tell Courtney that Jake and I did some sales deals back in 2020 — one being with DraftKings — which helped us a ton. But then I would bring stuff to Courtney to get her thoughts and she would say ‘Jim, you could be getting so much more.’ And I was like, ‘Oh, okay.’
Our dad set us up wrong. I asked him and he said, just offer her a one-year deal and see if she likes it or not. So I talked to Courtney about that and she said “No, if I do this, I want to be all in.”
Hirsch: I’m very black-and-white, all-in. [Laughs]
O’Brien: And I was then like “Thanks, dad!” [Laughs] But Jake and I are best friends, and at that point, my wife was working for us, doing all the ad administration — we’re super family oriented. So we [got a bigger deal done] with Courtney.
When you two do have different opinions on the business — what’s that look like? Do you ever butt heads?
Hirsch: Where do we butt heads … I don’t think we ever do. I think I’m trying to constantly help make sure that we’re doing stuff that is true to who we are and true to the content. So I’m usually pressing “Is this the right decision for the content?”
I don’t want us to be distracted by something that could be a quick sales win or a quick revenue number, because I want it to be a long-term business move. I’m just trying to find the core reason for why we’re doing something, then build it from there. And make sure it’s consistent with how the company has grown.
I’d love to hear more on that, how you balance what could be a good short-term move but not necessarily long-term. How do you weigh that?
Hirsch: I think if a brand came to us and they had a big check, but the brand doesn’t really align with who we are and what we do, that’s a good example.
I think we’ve made some of those “yeses” in the past, because back a couple years ago, when the economy was tanking, we had all these expenses, advertisers were pulling back a little bit, and we wanted to do what’s right for the company and its people, and we may have been a bit looser with a “yes” for a brand deal that didn’t like 100% represent our values. We kind of make those decisions together, though.
We have very separate lanes, where I’m [more focused on the business and Jimmy handles the content.]
O’Brien: I think, if anything, if there’s a disconnect — we’re very eager to try and understand where the other’s coming from or what’s missing. And Courtney is super supportive of the creative side and making sure we stay true to who we are.
The only thing is when she’s implementing structure — in meetings, she’s telling me ‘Don’t be late, pay attention [laughs], you are a culture leader, so I need you on my side.’
Those are things I’m not going to fight her on, they’re just a reminder to be united.
Give me an idea of the production process for you. You have 30 teams to keep track of during the season — how are you staying on top of what breakdowns to do on a daily basis?
O’Brien: Oh, we get suggested so many things, and so many things happen. Baseball’s really quick, there’s 15 games every day.
Some weeks it is really heavy — a few months back, I put out a joke [on X] like “Can managers stop getting ejected for one second?” [Laughs]
But we have to do three or more [breakdowns] every week. So on light weeks, it’s just trying to figure out what to do, go find something. And then there are certain ones that you know are going to be good, because it’s a hot topic or it’s lipreading — and then there are other times where we need to service a certain part of our audience or go get new audiences by doing women’s basketball or cricket or a different sport. There’s endless options.
When did you notice you had this gift for lipreading? And do you ever worry about, almost from a legal standpoint, getting something wrong?
O’Brien: Yeah, well I still can’t lip read. I couldn’t just look through the window and say ‘Here’s what they’re saying.’ [Laughs] Context looms very large: “What are they talking about? Okay, they might be saying this.” Then you find one word and then it unravels. I can do it more than the average person — sometimes I can watch and get it right away, other times it’s really tough.
Hirsch: Oh, You show me [clips] on the train, he’s like “Court, what are they saying?” I’m like “I have no F****** idea.” [laughs] I think it is more of a skill than he’s making it out to be.
O’Brien: Sometimes, but I could do it when I was a kid. But only sports stuff, just kind of guessing what they’re saying and then seeing it.
And then yeah, I am, in a sense, spying on players and taking their private conversations and relaying them to the world. So that is not cool sometimes. I try to never put something out there that would screw someone over, where they’re going to get questions at their locker because they said something out of hand.
There’s been a couple times where I saw someone saying something and I’m like, eh, it’s not worth it. But the feedback from the players and the managers is that they enjoy it and find it funny.
The way I’m delivering it, I’m not trying to go “‘look what he f****** said!” It’s more like “ha ha, listen to them, they’re both so mad. They’re goin’ crazy.”
And then, if I put the words on the screen, that means I really think they said it. If I don’t put the words on the screen, I’m kind of making a joke or messing around. But I’m usually pretty honest with the audience and let them know “Hey, I couldn’t figure this one out. Let me know if you got it.” And then someone usually comments what it is and makes me feel dumb. [Laughs]
Can you speak to trying to reach baseball fans on social, where they are now, rather than what the approach may have been a few years ago?
O’Brien: MLB Commissioner Rob Manfred recently addressed this too, and he said “We got this wrong” [on trying to reach younger fans on social media].
I believe the guy who was in charge of all those decisions — making it tougher for fans to use footage — left after 2016. And I just happened to start doing this in 2017, so it was just kind of perfect timing.
In 2017, nobody was posting GIFS or videos or games in-the-moment on social media besides me. I had 3,000 followers, but that’s why I skyrocketed to like 100,000 followers quickly. Because Barstool was scared to do it. Everyone else was scared to do it — teams couldn’t do it! They wouldn’t post GIFs or highlights from their own games. You think about that now and you’re like, “Really?”
And the technology to do it wasn’t there. The iPhone didn’t have screen recording, so I downloaded these programs, and taught myself how to do it. Now, it’s everywhere. It’s crazy. But it really was such a differentiator in 2017.
That makes me think of this latest deal you guys signed. Can you tell me why it was a good match for you guys to officially partner with MLB?
Hirsch: I think the timing is perfect, because they’ve had this change in mindset where they realize to grow the game, they need to reach fans where they’re already consuming content. And they need to stretch outside of baseball fans, and that’s what Jimmy and our company is really great at. We can make content that reaches the casual sports fan and create a new baseball fan, or bring someone back to baseball.
For us, they don’t want any creative control over content, which was a showstopper for us. And we get so much more access — access to MLB events and games. We’re going to come out with co-branded apparel, Jomboy Media apparel. We’re going to get access to players and do content collaborations with them.
For us, nothing really changed about what we’re doing, except we get more access and support from the league itself. They want us to keep doing what we’re doing.
Jomboy has an irreverent fan tone to the content, not that you’re really going after anyone. Is there any concern in the back of your mind where, now that you’re officially partnered with MLB, that you can’t go quite as hard as you want?
O’Brien: That’s been in the back of our mind when we do NFL or NHL. We used to say it on our wall: Don’t burn a bridge that hasn’t been built yet.
It’s in our nature to care about the people or sport we’re talking about — to not come off negative for clicks or do tear-downs. That’s not changing because we signed with MLB — that’s how we built our tone and we’re going to stay true to that.
But if we have opinions, we’re going to share them. Like, I think MLB’s [replay review] is broken, and I tweeted that. And a guy from MLB met me during all-star weekend and we debated — it was friendly banter — about why I felt that way.
Hirsch: The league also made us feel very comfortable during the negotiations that they wanted us to continue being ourselves and not do anything differently.
And now, with this infusion, what’s the next thing you’re looking to do?
Hirsch: I think we can do a lot with the people and staff that we already have. There are a lot more opportunities with brand sponsors and we have a full roster of creators in-house, and now we can do so much more with them. That’s what we’re excited about.
Last thing, if you were sharing advice with someone starting a YouTube channel, what advice would you give them?
O’Brien: I would say lose yourself in it for a little bit, and say no to everything… as in, all of the people who come offering you a penny, or who offer to do some editing for you. You need to learn how to do it yourself before you hand it off to someone else.
If it’s very early, do everything yourself.
