“You have to keep going and you will survive,” says Sean Owolo, partner and executive producer at Big Machine, a full-service production company. “Just choose to keep going.”
Owolo learned that through his own career, which he thought was going to start on Wall Street but ended up in music. After a decade, he saw what Napster was going to do to the music industry and he turned to a new career in television marketing.
But before all of that, Owolo was a student at Howard University in Washington, D.C., planning to get his degree and head to NYC.
“Howard was interesting because I always thought I was going to go to Wall Street. At Howard, I was very much suit and tie. When you grow up in Connecticut, it’s really Wall Street and seeing your friends’ dads on the train commuting to New York to make the money to come back to Connecticut. For a young African-American, that’s the influence in terms of where you think the money is. So that was my mindset.”
But a surprising run-in with a future music mogul had Owolo consider entertainment as a real, lucrative career.
“Along the way, Sean ‘Diddy Combs’ happened. Here comes this really cool kid at Howard that I see on the yard all the time that I was able to strike up conversations with. He was interning at Uptown Records at the time and some people thought that that was weird that he was sneaking away from school in the middle of the week to go back to New York to do this internship. But when he left Howard and took a full-time job at Uptown, I remember just being like ‘hey dude, so there’s real money in music?’ He told me what he was making and it wasn’t particularly a big amount. But, for a kid in college with no money scraping your pennies together to buy a two piece at Church’s Chicken, it was a whole lot of money!”
After graduation, it wasn’t long before Owolo moved to New York to see what he could make happen.
“I ended up doing a string of internships before going into the industry as a full-time music employee, which led me from Washington D.C. to New York City. I ended up working for a record label called H.O.L.A Records. I got to work with some real iconic execs like Steve Stoute.”
He had some success working with artists like Jamie Foxx and Sunshine Anderson, but things started to get uncertain. The emergence of Napster caused record sales to plummet and jobs to disappear. Owolo smelled disaster and jumped ship—or at least tried to.
“The first company I worked for was etour.com. I was employee number 28 or 29. I was pretty early on in the company with a bunch of stock. I thought, ‘This is great. If this thing gets big and goes public like all these companies are going public, I’m going to be rich.’ Very shortly after we ran out of money and people started losing their jobs until the infamous day, like most dotcoms in the early days, when they come in and go ‘we have no more money.’”
Once the dot-com boom evaporated, Owolo looked at other opportunities in an entirely new business.
“It was the first time that I didn’t have this really solid game plan,” he says. “I was like ‘let me just see what I can get in television.‘”
Soon, Owolo landed his first business-development gig in Los Angeles. The relationships he’d built up to that point worked in his favor.
“Relationships are how things get done,” he says. “The challenge that a lot of people have is when you’re looking at something from a business standpoint and going ‘I’ve got to make some contacts here.’ In order for you to be successful in whatever business, they need to like you and you need to like them.”
Now at Big Machine, Owolo and his team have won an Emmy for their work on Nat Geo Wild’s Future Cats. The Big Machine team produced the entire show, including the design and animation. That success led to even more opportunity.
“We started to think about movies and television. We put a couple of sizzles together, pitched them and we got enough traction that agencies in town started to look at us and pursue us as possibly giving us representation. One of the highlights for me is being with William Morris [editor’s note: now WME] because it’s such a big iconic company and I’m a guy that studies industries. When I became interested in movies and television I was reading biographies on people like David Geffen, Steve Ross, the original founder of Warner Brothers, and Michael Ovitz, the founder of C.A.A.”
Owolo’s career path has been full of twists and turns, reinventions and lots of education. His advice to those following in his footsteps? “Just realize when you’re at your lowest point that the sun is going to come out tomorrow whether you like it or not.”
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