Los Angeles, CA

The progression from street-level promoter to music industry mogul is no more a given than the leap an artist can make from local star to international sensation. Skill, talent, and an arduous work ethic have long been documented as requirements for next-level success in the industry gauntlet but it takes a special “it” factor that clearly divides the lines between an actual career and side hustle.

John Monopoly falls underneath that tenth percentile when it comes to artist management that developed into a real-life empire. If the name rings bells, it’s probably because you were at least in the vicinity of what was happening in the world of music, namely the Chicago Hip Hop scene. Back in 1991, Monopoly, then a local event planner in the Windy City, he started managing a hungry Kanye West back when most people would read his name as “Kane” and as their relationship grew, so did their avenues of their success. Kanye would go on to become well, Kanye and Monopoly’s eye for talent scouting would get him plenty of work with Jive Records, Violator and A-list artists such as Missy Elliott and No I.D., just to name a few.

Today, Monopoly is eyeing a bigger piece of the prize by embarking on his first ever festival this August at Houston’s Toyota Center (y’know, the place where James Harden can drop 40 like it’s nothing?). The lineup reads like a dream Pandora playlist, boasting of names like Fetty Wap, T.I., Rick Ross, Young Thug, Metro Boomin and more. For many, it will serve as solidification for one’s hustle but for John Monopoly, it falls right in line with his career design.

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HipHopDX recently caught up with him to get the breakdown on the upcoming festival that will certainly be nothing short of Outta This World.

HipHopDX: This Houston show is shaping up to be like a real good look.

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John Monopoly: Yeah man it’s going to be crazy I’m excited.

DX: Is this your first major concert series on your own

John Monopoly: Well you know I’ve been doing concerts for like 25 years. This is my first festival and arena and all that kind of stuff.

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DX: How’d it come about? What made you pick Houston above all cities?

John Monopoly: We were just looking for the right place that all the talent could perform and we kind of had like a wish list of talent. And there were places that they couldn’t perform because they were already slotted to be there. And Houston everybody kind of matched up and I got some relationships down there.

DX: It would appear that a festival like this is like the holy grail for every promoter, especially ones who’ve interacted with artists who’ve actually become superstars this for throwing festivals and then maybe align to other festivals. When you finally inked everything and when they create the flyer and you feel like you really accomplished something all those years grinding.

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John Monopoly: Yeah man absolutely I always wanted to do something of this magnitude but it never really happened like partners and I didn’t have all the things lined up to execute something like this but now it’s the right time and with the UIG Entertainment working with those guys is amazing and it just makes a lot of sense so it’s a true blessing.

DX: What year was it that you actually got your first start? Who was the first artist that actually put money in your pocket and gave you that bloodthirsty taste to go out and get it?

John Monopoly: I did my first party in 1989. It was a party in Hyde Park with a couple friends of mine. I made like $10 or $20 dollars profit, I don’t remember if it was $10 dollars or $20 dollars but it was just so much fun to actually make money for doing something that I actually like at a young age. Because you know I had jobs, I was 13 at the time when I did the party but I was working a job at a computer store in my neighborhood where I went to grammar school. But I didn’t like the job that I had, you know I needed a job, but I didn’t like the job so I was trying to figure out another way to make money that I would enjoy. So I think I saw Krush Groove or I don’t remember what it was or something or somebody had given me this concept of being a promoter at a young age and that’s kind of how it all started and then from there I started managing acts I want to say I managed this group called Prime Exposure in like 1990 I think I booked a couple shows for them I done made a couple dollars then I started managing Kanye in ‘91. I think we might’ve sold a couple beats and made a couple dollars in ‘91 or ‘92 and by that time I was just completely hooked.

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DX: That’s dope. Everybody saying like playing the old Kanye footage from the early 90s days, did you see that potential that he saw in himself that he always raps about or was he just a client at the time?

John Monopoly: Nah, I always knew he was going to be big—I didn’t know he was going to be the biggest thing in the universe but I knew he was going to be big I knew he was going to be successful. I was already a huge fan of his beats and his raps and all that so we always knew.

DX: Nice. What’s your most vivid memory of hustling with him like doing shows and stuff? What was one memory that you guys could look back at today and still get a laugh at?

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John Monopoly: I remember I did Jay Z’s first show in Chicago in 97 and I had Kanye open and he had this big polo hat on. Kanye was always fly. And my cousin Don C was like the flyest dude from Chicago ever.

DX: That’s what they say! I’ve heard that plenty of times.

John Monopoly: Yeah that’s just fact you know what I mean you can quote me on that. We did this Jay Z concert; I don’t even know if Jay knows this but I did Jay’s first show in Chicago ever. And me and my man Happy brought him to Chicago and it was like him and Foxy Brown. We did them at the Clique. The Clique was that club. You probably heard of it the E2 massacre in Chicago where like 20 some people died in that club and it was national news. They changed it. It used to be called the clique. It was called E2 when the massacre went down but when we did this in ’97 it was called the clique. And I was like 21-years-old and Ye opened for Jay but I remember he had this like big Polo hat on, but looking fly though. It was just the overall night and the overall experience, which was great because we were always trying to be progressive and bring fly Hip Hop to Chicago. And that was a great experience, the show was sold out and it was just a lot of fun. And it was one of the first big looks that we had for him as far as opening up for a big act and its just ironic that 20 years later he’s with homeboy signing with Jay. We actually didn’t meet Jay that night, I didn’t even meet him that night. It’s just ironic how it came full circle like that.

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DX: What about this video clip of Kanye getting his haircut talking about the first time he met you? Is he talking about you? Did you used to do beats too?

John Monopoly: Yeah I used to make beats. That’s how we connected. I was a producer and a promoter, I started throwing parties when I was 13 and I used to make beats too. And a mutual friend of ours introduced us and we connected on some beats and we started a little production company and we were just kids. But I was always on some business stuff because I got my first job when I was 11. And I had to work because that’s how my mom didn’t play with that not working type of tip so I was always trying to be entrepreneurial because I didn’t like my job. So I kind of started on the business path kind of young so when I met him I was like 14 or 15 but I was already trying to start a production company and I was traveling to New York and I was throwing parties and concerts. I did my first concert when I was 15. I did my first party when I was 13 so I was always just hustling.

DX: Nice. And with the festival, the date still stands right now August?

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John Monopoly: Yeah, Thursday, August 18th, Houston, Toyota center, me and UIG. It’s going to be great. I’m really excited about it.

DX: Yeah definitely. And what do you want fans of today’s Hip Hop to go in expecting and what do you want them to get out of it? Because it’s pretty much got about 85 percent of today’s radio on it right there.

John Monopoly: Yeah it’s going to be a lot of fun, man. It’s going to be a lot of great performers. It’s the first time you get to see all of these people all on one stage. I just think it’s going to be a great experience you know? I’m just really excited about it, I’ve worked with a couple of the acts before in other places and they always put on a great show so I think it’s going to be great. And there’s a couple surprises too that I can’t talk about.

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DX: I mean everybody goes to Houston so you never know who might show up.

John Monopoly: Exactly!

Outta This World
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UIG Entertainment and John Monopoly Presents announce the first annual “Outta This World” concert set to take place Thursday, August 18, 2016, at the Toyota Center in Houston, TX. Boasting a stellar performance line-up, the concert is set to be one of the hottest tickets of the summer. Sharing the same stage for the first time ever, Hip-Hop heavyweights Fetty Wap, Rick Ross, T.I., Young Thug, Ty Dolla $, Bun B and Metro Boomin promise the ultimate concert experience. Expected to attract an audience of 15,000, the Outta This World concert will go on record as the largest independent Hip Hop festival to take place in the city of Houston.

For more information about the Outta This World concert and to purchase tickets please go to: ExperienceUIG.com.