8 Lessons For Content Creators From Jomboy

  1. Make content you like
  2. 1k true fans
  3. Find a wedge
  4. Stick to your niche
  5. Content creators > content
  6. Going viral helps
  7. It’s not always fun
  8. Celebrate wins

As a content creator, I like to observe other content creators. As a Yankee fan, I like to consume Yankees content. This makes me a natural fan of Jimmy “Jomboy” O’Brien, a prolific creator of Yankees content and founder of Jomboy Media, a digital media startup that just raised $5M in funding. Jomboy recently appeared on the Joe Pompliano podcast and shared his story of going from a 28-year-old wedding videographer to founding one of the hottest media startups in the U.S.

The conversation taught me a lot about what it takes to succeed as a content creator. Here are some of my favorite takeaways:

1. Make Content You Like

Before formally launching Jomboy Media in 2017, Jimmy was grinding out two YouTube videos per week to his personal channel of 4k subscribers. He had no intention of launching a business—he simply enjoyed making videos on nights and weekends. When he applied his skills to covering his favorite team, the Yankees, that joy and enthusiasm came across, which was contagious to fans.

“If an idea is so stupid it makes me laugh, I enjoy doing that. It was selfish. I was bored and I was a hobbyist guy who needed something to entertain myself at night.”

The takeaway: The best way to make good content is to make content that interests you.

2. 1,000 True Fans

Jomboy’s growth was fueled by Yankee fans. In 2017, the Yankees were a competitive team after several years of mediocrity. Fans suddenly had a reason to start paying attention again, and Jomboy was there to capture that attention. They discovered his content, then amplified it to others.

“We picked up the diehard Yankee fan in each friend group and got them on board. Then they shared our content with their friends.”

The takeaway: You don’t have to reach everyone, just the right people.

3. Find a Wedge

In 2017, MLB changed their rules and allowed content creators to reshare official MLB content (previously only MLB could share game content on social). Jomboy became one of the first people to take advantage by posting Yankee game highlights to Twitter in real-time. After each game’s conclusion, he’d shoot a 1-minute reaction video (if the video went longer than 1 minute, he’d cut it and reshoot) and post it to Twitter. Crucially, he’d often be the first to reply to the final score tweet from the official Yankees account—thereby maximizing his content’s exposure.

This differentiated approach to Yankees coverage allowed him to stand out in a saturated sports media landscape.

“I was the only person posting Yankee GIFs of the play right after it happened, and I was first person posting thoughts on the game and jokes in real time. Nobody was doing those things. I grew my following that way.”

The takeaway: You can insert yourself into any market by bringing something new to the conversation (especially on Twitter).

4. Stick to Your Niche

Some content creators find a niche but then expand in ways that aren’t true to what made them initially successful. Jomboy knew his success came from the “casual fan, sitting on the coach in the basement” tone of his coverage. As he scaled the business, he aimed to maintain this fan-like passion while upping the quality and professionalism of the content production.

“I wanted things to feel professional by broadcast but amateurish by tone. Very casual but it also looks good.”

The takeaway: Double down on what works, shed the rest.

5. Content Creators > Content

Part of sticking to your niche is hiring people who also fit that niche. Jomboy Media hires passionate sports fans who are adept at creating content in multiple formats. This allows Jomboy Media to maintain its “sitting on the coach” tone with creators who can monetize their influence in multiple ways.

“The sport isn’t important, it’s the person and the tone and brand. It’s hard to find folks we feel fit and understand the work ethic in this space. Like, someone wants to do a Jets podcast. But it’s like, what else? If Jake (Jomboy’s co-founder) and I just did the Talkin’ Yanks podcast, it’d be a side job. You need multiple formats and to diversify your content. We like to ask people what would be the ‘menu’ of their show.”

The takeaway: Hire subject matter experts and let them tell you what to do.

6. Going Viral Always Helps

Jomboy had two viral hits in 2019: Aaron Boone’s “Savages in the Box” video (2.6M views on YouTube), and the video where he broke down the Houston Astros cheating scandal (above). The former left the scope of baseball and became a nationwide sports story, the latter left the scope of sports and became a nationwide news story. The Astros video in particular worked because of elegant articulation (he explained their cheating scandal in a 2-minute video). These viral hits got Jomboy’s name out there, and once they did, fans discovered his entire back catalogue of content.

“The viral hits didn’t create spikes in traffic, but new plateaus because we had reached a new level of exposure. People realized we put out this content a lot and they knew to start coming back to us. So instead of a blip on the radar, we stayed at this elevated status.”

The takeaway: Going viral is a tide that lifts all boats. You can increase your chances of going viral by taking a lot of shots on goal.

7. It’s a Grind

In 2019, Jomboy said he worked from 9AM – 2AM every day recording podcasts, making breakdown videos, managing social media, and doing live commentary for Yankee games (Jomboy Media had received a $25k investment that year, allowing Jomboy to pay himself $500 per month). In his own words, it sucked:

“It was bad for my health and my relationship with my wife. I don’t look back fondly on that tome because I let personal relationships slip. My girlfriend had to sit down and have a serious conversation with me over what i was doing. So I don’t look back fondly on it.”

The takeaway: Success is great, but the work it takes to get there is unglamorous and often painful.

8. Celebrate Wins

Jomboy said his dream scenario when he launched the business was to make $60-$65k per year talking about the Yankees. Today, Jomboy Media is valued in the millions and has 50+ employees and a show on YES Network. Jomboy said he got there by ignoring what “could be” and doing the work:

“I let other people do the dreaming for me, because I was too busy working”

That’s not to say Jomboy doesn’t appreciate how far he’s come. In fact, he goes out of his way to appreciate whenever anything cool happens.

“Derek Jeter said he regretted never enjoying the moment after he retired because he was always thinking about the next thing. I’m the complete opposite. Anytime something cool happens, Jake and I take a moment and text eachother. Sometimes we cry.”

The takeaway: Content creators don’t get any validation for most of the content they put out. If and when you finally do, it’s worth savoring.


  1. To make good content, make content that interests you.
  2. You don’t need to attract a ton of fans, just the right people.
  3. Differentiation is a wedge into the market.
  4. When you find something that works, double down on it.
  5. Hire people who know more than you and let them tell you what to do.
  6. Publishing a lot of content increases the chances of going viral, and going viral improves the performance of all your content.
  7. The road to success is lonely and difficult.
  8. If you do see success, savor it. It’s rare.
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