Like Clint Eastwood and Christopher Nolan, Maverick Carter has his office on the Warner Bros. studio lot. Once you get past security, you drive by pinup western storefronts to a section of cookie-cutter houses with vinyl siding. (Gilmore Girls was filmed here.) Even the grass looks like it's from Milwaukee. Outside one of the houses are reserved parking spots that read: “M. Carter” and “L. James.” That and the shiny silver Maybach parked out front are the only tells that inside this unassuming house, the future of sports marketing and entertainment is being crafted. This is where Maverick Carter gets to work.

Carter is LeBron's friend from Akron—he was a senior at St. Vincent-St. Mary High when 'Bron was a freshman. He's also the Cavs star's business manager. But most important, he's the creative director of all things King James. What does that entail? Well, NBA basketball and an apparel empire. A Hollywood production company. (The Starz show Survivor's Remorse is Mav's.) A scholarship program. And a media platform called Uninterrupted, where players tell their own stories.

Here, the man who just played a central role in the largest celebrity apparel deal of all time breaks down his negotiating strategies, his regrets—and how he turned a ballplayer from Akron into a billion-dollar global brand.

GQ Style: You're really making a go of this Hollywood thing. Was this always the goal? Was 8-year-old Maverick Carter dreaming about Hollywood?

Maverick Carter: No. It was never my dream.

When did it become your dream?

When people ask what college I graduated from, I say: I didn't graduate from college. I graduated from Nike. I started my career as an intern getting coffee. I was working in sports marketing, which means building the brands of Nike and the athletes. What I realized after I left Nike is that they tell stories. These shoes I have on are just shoes. Obviously, they put some technology in it. This is knit. This is lunar. Blah blah blah. But they tell you the best story ever about this sneaker. They tell better stories than anyone in Hollywood. So it was just a natural evolution: marketing, storytelling, building your brand, producing content. I'd been doing it my whole life already.

What do you think is the biggest mistake you've made so far?

[takes a moment to think] When I first left Nike to go work with LeBron and manage him, I was really bullish about managing other athletes. I really wanted to get more athletes besides LeBron and build this big management practice. And in hindsight that was a mistake.

Why was it a mistake?

A couple of reasons. One is that there's only one LeBron. Another reason is that other athletes always viewed me as LeBron's guy. They thought: He can't be my guy, too. It was a mistake because I lost time on it. And managing LeBron was enough. It was plenty to do.

Do you regret managing Johnny Manziel?

No, I don't regret it. I met Johnny and liked him. He obviously was who he was coming out, which is gigantic. I feel like we did a great job with Johnny and helped him a lot. But he was his biggest opponent. He's a very intelligent guy—he's just his biggest opponent. Still is. But to this day, if he called me, I'd go help him in a second. So that's another reason why I can't regret it: I made relationships with him and his family that'll probably last a lifetime.

When did you and LeBron decide Hollywood was the next frontier?

It was the natural evolution. Obviously, the goal was to figure out ways to take his talent, who he is, what he represents, and build businesses around that. Because being a great basketball player, there's a very tight window.

So you guys have always been working on life after basketball?

Once basketball is over, you've got fucking 50 years left to live. So you gotta hit 'em while you got the muscle, as they say in The Godfather.

“Some people are more prepared to take risks. I grew up a gambler. That’s my name: Maverick. That’s what it comes from.”—Maverick Carter

What did you want to be when you grew up?

Well, like every kid playing basketball, I dreamed of being an NBA player. It's kinda like that Chris Rock joke: In the hood, there's only a couple professions. My dad was a drug dealer. My mom was a social worker. In seventh grade, I was on an AAU team, and we went up to this neighborhood called Hudson. It was nice, with big houses. I was like, Holy shit, people live like this? And to the Chris Rock joke, the guy whose house I was at, his dad was just an athletic trainer. He was an athletic trainer for the Cleveland Indians. He wasn't a basketball star or a musician. Chris Rock says the white guy who lives next door is a dentist. The black guy has to be the greatest in the world. So when I saw that, I wanted to be an athletic trainer.

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Are you close to your father?

Very close.

You have to have a knack for business to sell drugs successfully. Did any of your father's wisdom rub off on you?

Yes, a hundred percent. He gave me the foundation, and I built on top of it. He dropped out of school in ninth grade to be on the street, but our foundations are the same. And that's being passionately curious. Always wanting to know.

When I was a kid, being a businessman meant that you wore a suit every day and ate steak dinners. But you're wearing sweats, drinking a green juice. What does being a businessman in 2016 mean to you?

The biggest thing it means is that you have to be infinitely flexible. Tech is changing every industry every single day. All the cards are on the table now. And when all the cards are on the table, the game changes. You have to play it a different way. So I think it means being curious and flexible while still having principles you live by and guardrails that you do business within.