How Lil Bibby Successfully Transitioned From Rapper to Hip-Hop Executive

Made Me
Lil Bibby is learning that there's way more to life than being a rapper.
Words: Vanessa Satten
Editor’s Note: This story originally appeared in the Summer 2019 issue of XXL Magazine, on stands now.

On a warm sunny day in early June, Lil Bibby wanders around Chicago’s Lacuna Lofts, a former macaroni factory that’s been converted into a colossal creative building with offices and event spaces. The Chicago native doesn’t work in the building, but it’s a good spot for an interview and photo shoot. As Bibby explores the different floors, fans sporadically come up to get a picture with the artist-turned-label-head. He makes time for everyone.

Bibby first broke onto the hip-hop scene in 2013 with his mixtape Free Crack, which was followed by 2014’s Free Crack 2, 2015’s Free Crack 3 and Big Buckz the next year. Along the way, Bibby signed to RCA Records and Dr. Luke’s Kemosabe Records before putting out his FC3: The Epilogue EP and parting ways with RCA. Bibby still has paperwork with Dr. Luke.

For the past few years, the 24-year-old rapper, born Brandon Dickinson, hasn’t been focused on recording his own music but rather on building his label, Grade A Productions, with his brother George “G Money” Dickinson. The two have seen huge success with their first signee, Chi-Town representer Juice Wrld, whose second solo album, Death Race for Love, dropped this March and landed in the No. 1 spot on the U.S. Billboard 200 chart.

Speaking to XXL, Bibby discusses his transition from artist to executive, signing Juice and the rest of the Grade A roster, making money and more.

XXL: You came in the game as a rapper and now are making this transition into label head. What do you define yourself as?

Lil Bibby: I really don’t know. I like to make people a lot of money. I got enough knowledge and I’ve studied this rap stuff and I got enough relationships to help an artist, help his family [and] I get a kick out of it ’cause I see how the label does it and my situation. I feel like just helping people.

If someone asks you what you do for a living, how would you answer?

I make people a lot of money.

When was the last time you were in the studio recording?

I tried it out like two months ago. Before that I probably haven’t recorded in about a year and a half.

Oh, so are you over it?

Nah, if I get out of my contract… It’s easy for me and I still got stories. I feel like, I don’t know too many people that seen or been through the stuff I have been through.

So, you have been focused on your own company? Tell us about it.

My company is called Grade A Productions. I’m working with Juice Wrld, of course that’s going well. I signed this other kid named The Kid Laroi from Australia and I signed this other guy from Alabama named Clever and this other guy from Ohio named Seezyn. So, I kinda have a lot on my plate.

Do you have any problems not being the rapper that’s in front of the camera?

No. I really hate the cameras. I haven’t done any interviews in about four years. I really don’t like attention like that.

Where did the name Grade A Productions come from?

I thought of that name. I had this company about four, five years ago. It sounds like a clean name. It sounds universal and it wasn’t tied to anything. I just like the name.

Of course, Juice is an amazing look as Grade A’s first artist. How did you connect with him?

My brother [G Money] brought Juice to me. He played me the song “All Girls Are the Same” and I was like, “Alright, that’s a good song.” Then he sent over some YouTube links and I heard “Lucid Dreams.” When I heard “Lucid Dreams,” I’m like, “Oh, now this is probably the best song I’ve heard in over 10 years.” That’s when I really knew. I [was] like, “OK, we gotta go with this.” So, I got to making all the calls [to] all the radio people that I know. Everything just worked [out] perfectly. The Cole Bennett video came out and it did wonders and we were already in label talks.

You ended up signing Juice Wrld to Interscope Records. Is Grade A at Interscope or only Juice?

Juice is at Interscope. I didn’t do a label deal anywhere.

Is that the goal? Do you want a major label deal one day?

I don’t think so. I have to talk to my lawyer ’cause he’s talking me into doing a label deal or something like that, but I don’t know if that’s where I want to go. I don’t like to be tied to anything.

And your brother George “G-Money” Dickinson is your partner with everything?

My brother is my partner with everything. He plays a big part. He found Juice [and] he brought him to me. We put the project together, a huge success. He found Clever and we are working on that. He put out two songs and it’s going well. We have this Australian kid [The Kid Laroi] I’m very excited about.

Juice Wrld is from Chicago. Was that important for you to have your first artist be someone that was local or it just worked out that way?

It just worked out that way. I don’t care where they are from. Me and Juice connected a little bit more because I understood his story and where he’s trying to go with the music. He’s from [my] hometown and knows how things work around here.

What do you think of the Chicago hip-hop scene these days?

I like it. There’s a lot of good artists like Lil Zay Osama, Polo G, Calboy, Juice Wrld, of course.

I feel like we have to get the business part right. I want everybody to get the business part right so we can make artists bigger. I’m a big fan of what Atlanta is doing. They got real moguls, real music people that take artists and really mold them. They do the business part right.

What do you think of Chance The Rapper and Kanye West's contributions to Chicago?

I think Chance and Kanye, it’s good to see. It brings motivation for everybody. It’s good to see Chance do it independently. It’s good to see Kanye make it as far as he did, but they gotta share the information. In Chicago, it’s so crazy out here because people have egos and everybody want to be in competition. I tried to share some information and people sometimes look at you like, Who do you think you are? I can do it, too. I can do it just like you.

But it’s just free information to help people out. I don’t let it get to me. I don’t let it push me away from [people in] Chicago because I know how they are. I still try to share as much information as possible because it’s impossible to know how much money is to be made. But everybody have egos and they should put that to the side. Anybody that’s willing to give you some free information, you should listen, especially if they been doing it for a while.

In the seven years you have been in hip-hop, what have you learned about the industry?

I have been a student. Most artists get in and just want to rap and let other people handle
the business. I want to know everything. I think that affected my career a little bit because I want to play every role.

Does that come from being burned by situations you were in or just your interest overall in every aspect of the industry?

I just got big trust issues. I want to know how everything works. I don’t really trust people when money is involved. Anything that has a lot of money involved, there are a lot of snakes. I think I’m one of the weirder people.

Why do you think you are weird?

I really don’t care about a lot of stuff. Like, everybody wants the craziest cars, the craziest houses. I don’t really like all of that. I don’t know what to do with all of the money. Sometimes people get really weird when they get some money; their ego gets crazy. I just like watching people.

Are you successful in your mind? How do you look at yourself in your personal achievements?

I’m doing OK. I feel like I’m successful and I have a goal. I’ve been successful. A lot of people don’t know, I didn’t have to rap a long time ago. I never put out an album. I went broke before.

Humbling experience?

Yes, it was very humbling. So, I took time off and learned what to do with money. I figured it out. You have to make money while you sleep.

Do you have a better grasp now of what to do so you don’t go back in that position?

Of course. I really like real estate. I know about stocks. I like passive income. I own a lot of real estate. I make more money than I spend every month in my sleep and I don’t have to work anymore. I got places all over [Illinois].

What made you get into real estate?

It’s a win-win situation. You are putting your money into a property that will eventually go up in value and you are making money every month. I always thought I needed to own something that people need. It’s only three or four things that people need in life—water, food, somewhere to live and clothes. People are not going to stop making babies—everybody is going to need somewhere to live, so I might as well own land. They are not making more land.

There’s a sense of empowerment in ownership. Do you get the same ownership feeling with your label and your artists like you do with real estate?

I do. I’m young, I got a great ear and eye for talent. I don’t need these old people telling me what to do and how to do it because I’m on the ground and I’m with the people. I know what the people like. I don’t want to bash anybody because there are a lot of good executives who have great ears, too. But I like ownership.

Are you going to end up in L.A. and be courtside at the Lakers game? That’s a record executive thing to do.

Not at all. I know a lot of Lakers players. I know a lot of Clippers players. You can’t drag me to those games. I fall asleep at those games. I like watching them on TV.

So, you are totally antisocial.

I am. I don’t know how to have fun. The only time I had fun was on jet skis in Miami.

You have to move to Miami.

I’m thinking of getting a spot out there.

What puts a smile on your face? What makes you happy?

I think I found it. I like to make people a lot of money. I like seeing people come from nothing to something.

You are into being a part of somebody else’s success. That’s a high for you?

Yeah, it is.

You figured out a way to succeed and make money with the people you are working with. Is that the successful part for you or would you feel just as good if you didn’t make any money with the people you are working with?

I would feel just as good. There are some situations that I don’t make any money off of and I give free information. I’ll tell them the whole rundown. It only takes maybe a couple of hours out of my day. If you want to know all about the industry, how to get paid, how to do this...if you are going to listen, I tell you. It’s not going to hurt me.

If you want me to do it for you, I have to charge you. If you want to do it yourself, I tell you all the info. It’s super hard and it takes a certain type of person to do it.

What are you looking forward to?

I’m trying to get Juice to the next level. He’s big right now. Huge album, huge song, but I want to make him a household name. I know the kids love him. We just did [a concert with] over 24,000 people in Connecticut. The whole tour sold out, but I want him to get bigger.

We gotta ask you about Juice Wrld and Freshman this year. First you guys agreed to have him be a part of the class and then you changed your minds on us. What actually happened?

I don’t know if I can put this blame on anybody. I don’t know. We all talked about it. But then it’s like, it’s my company, my partners, Interscope. We talked about it and it didn’t end up happening. We were really considering it and I know Juice would probably rap for a whole hour on the freestyle.

I get tired of Juice freestyling. He does that every day, I swear to God. Every day he’s on the bus freestyling. I be like, “I’m so tired of this shit.” But I look at it, like, [there are] people that can’t do that shit. I can’t do that shit. He knows how to freestyle all day and make sense. I have never seen anybody do nothing like that. That’s a freak-of-nature talent.

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