Jimmy “Jomboy” O’Brien is an online personality and content creator — with over 375,000 Twitter followers — specializing in MLB videos. The lifelong Yankees fan runs the rapidly growing Jomboy Media, with some of the most popular podcasts in the industry. He first went viral (over 8 million views) with a recap of Aaron Boone berating an umpire, then drew national media attention with his breakdown of the Astros’ cheating scandal.
Sports Section sat down with O’Brien to discuss the origins of Jomboy Media, his baseball fandom, and much more.
Below is an excerpt from out sitdown with Jomboy:
Were you always a baseball guy?
I’ve always been a baseball fan. I’m born into it. I remember when I was 7 years old and the Yankees won the 1996 World Series and we were at a friend’s house — all the adults were hugging and clapping, and I was watching in awe as the Yankees dogpiled on the mound.
How did Jomboy Media evolve?
It’s a hobby that has become a media company. We went from just tweeting and GIFs to writing articles to a podcast — then (tech entrepreneur) Andrew Chapin saw it and said, “Hey, if I gave you $25,000, would you try to turn this into a full-time gig and try building something?” The growth has been insane and organic, really rewarding. I give a lot of credit to our audience.
Is it fair to say the Aaron Boone video was the first one that really put you on the map?
That was the first that went beyond the internet world. When it happened, I was getting interviewed on the radio, MLB Network was having me on to talk about it, and ESPN was writing an article about it. It was the first time people outside the internet grabbed it and shared it to other places.
Did you imagine making a living the way you do now?
I always liked writing, but it was always taking part-time jobs, so I had space to do some creative stuff on the side. And maybe, deep down, I lived that way because I thought this could become what it did.
Read the full conversation here.