Is green tea always your beverage of choice?

Yeah, it gets you right … It’s the only tea I don’t need to put anything in. I’m vegan, it goes along with that lifestyle. I don’t put anything in it.

Will we find you drinking tea at the club?

No, it’s always before. But it’s the remedy to heal you after the club. 

Since we are at Virgin Hotels Chicago in The Casting Room inside Miss Ricky’s, if entrepreneur Richard Branson walked in the room, what would you ask him?

I was in Dubai one night and I told him that I just wanted to be around him. Actually, I asked, “Could I stay at the island?” and he told me yes. I just had to make a call and make sure nobody was staying there and he was going to allow me to stay. He definitely let Mariah Carey get Necker Island one weekend.

Mariah didn’t ask you to join?

No, she didn’t bring me. But I think she told me about it. She was like, “I was staying at Richard Branson’s island.” At that time I wasn’t really up on him having his own island. I really want him to know that I admire him, and he’s definitely one of those people that I keep in my mindset for motivation. He’s definitely that dude.

What’s the craziest rumor you’ve heard about yourself?

There’s so many. I know one that is crazy, and I want to make sure people understand.

Set the record straight.

Anything that people see me do, they should know that I do it as opposed to allowing a situation to happen. I’m speaking on Mariah Carey and me. The press put out that I got fired [as her manager]. As if I could get fired. I can get fired but I hope I’m smart enough to not be put in that position. That was a situation I walked away from because we have such a great friendship and relationship. I didn’t want to go into the zone of being the angry manager. I don’t think she was ready to do the things I was trying to do. We were just moving in two different ways but it was perfect for us.

What’s the best business advice you’ve ever received and who gave it to you?

Never get caught up in doing something once. People don’t take you seriously until you can prove to them you can do it multiple times. I think that was the biggest piece of information I could have ever received in the beginning of my career. Babyface told me that about Kris Kross. Kris Kross was a huge success for me and a huge success for the world, period. At that point I was lost in how I had the number one record. I wasn’t really lost, I knew what I wanted to do, but I was in it. He actually talked about the record like it was small. That day it triggered me to say, “Okay, I’m going to do this as many times as I believe I can do it to prove it to him.” In this business if you get one hit record they’ll put you next to people that had 10 hit records and they’ll start saying, “Jermaine Dupri is the new Babyface,” and that’s not realistic, right? That’s not true until you can do what Babyface has done. I think him saying that to me let me know that. You’re not a producer until you can do it multiple times.

Is it true that at one point you didn’t think you could make a record bigger than “Jump”?

Oh yeah, I still feel that way. Music is looked at in different types of ways. “Jump” is a huge record itself. Kris Kross was one of the most iconic groups of the ’90s and then I wrote “We Belong Together” which was Mariah Carey’s song of the decade. “Jump” still feels like a bigger record to me. More people seem like they were connected to “Jump” than “We Belong Together” but “We Belong Together” being song of the decade means it was the biggest record in 10 years … I can’t make another “Jump” and have it do exactly what “Jump” did. I don’t think I’ll make another record like “We Belong Together” either.

Anything you wish you did differently over the years?

Just being young and arrogant has cost me a lot. A lot more work. I’m not big on confrontation. There were times I had to work a lot harder than if I would have stayed and argued with somebody. Some people like to argue, some people like to just get into it with a person and I’m like, “You want to argue? I’ll see you later.” I’ll leave and a lot of times it’s not the thing you should always do. You should probably argue and I’ve learned you should just have it out with the person. Especially if you like the person. Ya’ll will get past it.

When radio stations weren’t playing your music in the beginning of your career was it ever hard to keep going?

Nah. It’s always been like, “You’re not playing my record right now, you weren’t playing my record two years ago so at least I’m having a conversation with you.” That means I’m moving a little further than where I was two years ago. You have to look at every little thing as progress. That’s what has always moved me. I use every little piece of forward moving as motivation to continue.

Would you say you’re living out your dreams?

For the most part, yes. Your dreams never stop and your dreams continue to get bigger. I have kids now so my dreams are to see them go to college, to see them live their life and to be able to make sure that they do that. My dreams are still out there. I post a quote each day on my social network Global 14. Today I posted a street sign of Berry Gordy Avenue. I don’t feel like I’ve done anything in Atlanta until they give me a street sign. I’m clear to that. If I don’t get a street sign in Atlanta —Jermaine Dupri Avenue, Jermaine Dupri Street— I’m going to die feeling like I haven’t done anything. [Laughs]

Would you rather be stuck in an elevator with Usher, Jay Z, Diddy or Snoop Dogg?

Probably Usher.

Why?

We would have the most fun. Well, Snoop, I’d probably have a lot of fun with Snoop but I don’t smoke weed. Puff and I might…yeah, it’s a toss up. Jay Z and I would have a lot of interesting conversations because that is what we do. We have a lot in common so our conversations would be very intriguing. But as far as fun, Usher and I would figure out something crazy to do like hitting the buttons and calling somebody. We’re a team like that.

Any regrets in life?

No, but I did a song for Aaliyah and I was listening to that song on her birthday. I thought to myself, “Man, I should have done something 100 times better than this.” You don’t know how long a person is going to be in your presence so it was just a weird feeling that I got. I don’t really regret it but I was just thinking I could have made something a lot harder and a lot better. It’s sad that we lost Aaliyah and it’s crazy I got an opportunity to work with her before her passing.

When do your best ideas come to you?

When I’m around a bunch of people that are creative and my mind is going a hundred miles per hour. I found an artist that’s here in Chicago. He’s shooting his own videos and just watching him do it without having anybody from the music world backing him is amazing to me. That inspires me to do more because here I am, a guy that people know and I can go do stuff because I have a track record, and this kid is doing all of this stuff and he doesn’t have any of that. It makes me say, “Am I working hard enough?” We should all ask ourselves if we’re doing enough.

Do you have any flying rituals?

I get on the plane and actually go to sleep. That’s the only time I get uninterrupted sleep.

If you could have a drink with anyone, who would it be?

For me it would be Berry Gordy. I haven’t had an opportunity to have a one-on-one with Berry Gordy. He is my all-time idol as far as creating enough music that a city changes the name to become your record company. I went to Detroit and I went to Motown. I got a chance to walk around the offices and hear stories. He’s another [inspiring] person. He went to a bank and got an $800 loan and started Motown Records. It’s iconic. I look at myself and I think, “Damn, I haven’t done that.” I’ve come close but will it go down in history that people know about Atlanta because of me? He’s the one person if I could have a cup of green tea with I would love to sit right in this restaurant, in this hotel and have a one-on-one.

We’ll let you get off to your dj set. You mentioned your clean diet, do you drink alcohol at all?

I do. Tequila … It’s basically the cleanest alcohol that you can have. If you drink nothing but tequila for the whole night you shouldn’t have a hangover. You should be cool. Just don’t mix it.

We’ll have to do a part two with tequila when you have your street sign.

Yes. When I get Richard to bring this hotel to Atlanta!

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KIRSTEN MICCOLI PHOTOGRAPHY / A DRINK WITH