Interview by Christian Alexander

John Monopoly is a living legend and the absolute definition of success. He’s guided the careers of a number of Chicago artists including Carl Thomas, Kanye West, and King Louie. I recently sat down with this elusive icon to discuss the culture of Chicago and the future of its artists.

“Nobody had swag, man, we the Rat Pack, Virgil Pyrex, Don C snapback, IBN, Diamond, Chi-town shining, Monop’ in this bitch again, changed the climate.” -Kanye West, “I am a God”

My first memories of you are always hearing, “John Monopoly! John Monopoly!”—I was like, “Who is John Monopoly?” and then I see the swag, I see the All Pro Fam, Hustle, I see the events, I know you’re not a nightlife person, but more events and products. You were one of the first out there to really do it. There were a few other people but in that era of the early ’90s in Chicago, I remember you always had a certain character, a certain swag. So what does that have to do with All Pro Fam for people that don’t know about it? How did that all come about?

All Pro Fam was a collective of young promoters and young marketing guys that were likeminded and wanted to bring something fresh and progressive to Chicago and the hip-hop space. In the mid-late ’90s, I want to say All Pro Fam was like a ’97 type of thing. In ’98 we started the Hustle brand. It was me, Happy, Don C., Lume, and Coodie—it was like a little crew of us. We were all from the city and doing our own things and involved in different things. Before Coodie was directing music videos he had Channel Zero, which was a legendary Chicago hip-hop culture show, Lume was a marketing guy working with different brands, and Happy being an OG record promoter now reinvented himself as a DJ.

One time Happy picked me up. I know it was late, after midnight, after a radio session at Columbia College. I had an artist in town and their car had a flat, and I called Happy and he came through and scooped me and took the artist to a show. There are so many good stories about that network. Seeing Coodie roll up at MTV and show that “Through the Wire” video, late night before it even had images in the polaroids. We always stayed connected and looked after each other. I think that’s a reflection of that, it’s all professional but it’s a family I guess.

Yeah absolutely, and we still do. I still do stuff with Coodie to this day. We just shot this video out in LA with this new artist like two months ago. Happy and I still work together—Happy is in LA right now staying at my crib. We still do stuff all the time, and Don is my cousin—that’s family—so we’re together all the time.

Don has the store now as well, RSVP Gallery.

Yeah, it’s doing extremely well. RSVP and Just Don are luxury products. He’s really taking off.

So tell me what artists are you working with now? We can get into your history with Kanye—people think it starts there, but I want people to know where it began.

I’m working with this artist named King Louie, he’s signed with Epic. He was featured on Kanye’s album on the song “Send It Up.” He’s just a really dope MC from the drill scene.

Where is he from, Chicago?

Yeah, he’s from Chicago, from Drill City. He’s dope. I started working with this female artist Dreezy, she’s also from Chicago, she’s tryna get up and out of there. She’s got this new record with Katie and Sasha called “Zero.” There’s another kid KD, an ill writer/artist, and we’re working on his process. There’s this other artist signed to BMG named J. Hill, he just produced that new Migos and Sean Kingston record that dropped a couple of weeks ago.

So would you say these are people you manage?

Yeah, these are people I manage, it just depends. Then I have a consulting business where we consult independent labels. I’m hoping to launch a couple of artist’s careers through their own situation, so we just give them infrastructure.

Back to Kanye—how did you guys connect and how did you help with his career and so forth?

I met him in 91 through Jean and Lucian, they were in a group altogether with Ye called State Of Mind. He heard my beats and I liked his beats and we started a production company called the Numbskulls in ’92. We kinda managed him with my crew off and on till 2008, we did the first three albums together: College Dropout, Late Registration, and Graduation.

You’ve worked in so many different aspects of this business. Where do you see a form that you haven’t tapped into yet, that you’re working towards?

Honestly, I’m really interested in technology at this point in the game. I moved to LA about a year and a half ago to take a position at a social media company where I was an urban managing director and a small partner in the company as well. It was just interesting to work in that space and move around those people and see the kinds of revenue that can be generated from the right tech. It’s just a different thing, different kinds of people, different opportunities. Without spilling the beans, I’m definitely interested in digital media and technology

What was it like for you as a kid? What drove you towards this creative form of business?

I grew up in Chicago, South Side. I come from a business family. My family started Johnson products. My dad, who was one of the heads of Johnson products with his brother, actually founded the company, and they went on to launch Soul Train. They were very historic figures in the city. I think I was just inspired by that lineage at a young age and was really into hip-hop music and culture growing up and always wanted to be in business. So the two collided when I was maybe 12 or 13 years old and saw Krush Groove and decided that I wanted to be Russell Simmons. My first hip-hop concert when I was 15 was actually The Beatnuts. I just got into the promotion and music game and wanted to produce, promote, and hustle around at a young age, wanting to be in business from my dad and wanting to be in hip-hop from my surroundings.