Everyone familiar with Matthew Cherry already knows his story. The former NFL player left his career on the field to pursue a career in entertainment, taking a job as a production assistant before directing music videos and later projects of his own, including The Last Fall and 9 Rides, which was impressively shot on an iPhone.

Cherry has since been attached as a producer to projects like BlacKkKlansman and The Last O.G., starring Tracy Morgan, and is currently an executive at Jordan Peele’s Monkeypaw Productions.

His successful turn in the entertainment business comes as no surprise to the Chicago native, who’s been pursuing the field since he was a teenager — from joining the radio club in high school to being part of the radio station in college.

“I majored in radio-TV broadcast and media production,” Cherry told ESSENCE. “I always knew that when I retired that something in entertainment was going to be in my future. I didn’t know exactly what. Already having an interest growing up really helped that transition be even smoother.”

The producer-director is the perfect person to look to if you’re interested in pursuing entertainment professionally. Although he admitted that he’s still learning, he’s established enough to have a few gems of wisdom, especially when it comes to figuring out how to maneuver in the industry.

“When you’re coming up as an indie filmmaker, you don’t have access to a lot of resources so you have to tell stories that are more personal and things that you relate to on a personal level,” Cherry advised. “Since I’ve been able to work here at Monkeypaw —shout out to Jordan Peele. He’s really given me an opportunity to work on some cool stuff—[I’ve been able to work on] projects [that] are trying to say something, projects that use genres to kind of put the medicine with the candy in some ways and make things that are fun, but also impactful.”

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Despite having worked with major talent on big-budget productions, Cherry hasn’t quite gotten used to his new role.

“To be honest, everything is surreal. Anytime you grow up, and you’re a fan of the business, and then you end up working with real people in real life and having conversations with people and actually becoming friends with some of these folks, it’s just crazy,” he said.

“I remember being a [production assistant] on Girlfriends and then just [being amazed…] because I used to grow up watching this show. Seeing Tracee Ellis Ross in person and even directing, and seeing Tracy Morgan [on The Last O.G.]. I’m like, ‘I used to watch him on Def Comedy Jam and Martin,‘” Cherry continued “It’s just been really amazing to work with these people that I’ve just been a fan of on a deeper level.”

And Cherry continues to branch out with other projects to explore other interests. He’s added author to his resumé with Hair Love, which hits shelves on May 14. Sony Animation picked up his book and will soon release it as an animated short as well.

Cherry said the love and support he’s received for the project, which went viral on Twitter, has been amazing.

“Anytime you have an idea, you never really know how it’s going to connect with people. This all just started with an idea. Wanting to tell a story about a Black father trying to figure out how to do his daughter’s hair for the first time. So it’s just crazy,” he gushed.