Transcript: Conversation with John Monopoly

Date: 2025-04-26 Time: ~4:00 AM Participants: Gary Sheng (GS), John Monopoly (JM) Context: Informal interview/conversation discussing John Monopoly's background, career, philosophy, and alignment with Gary Sheng's education revolution initiative following "The First Supper" event.

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JM: from from '91 up until now, I also am credited with discovering Virgil Ablo in 2006, in Chicago at mine, and helping to put on my cousin Don C, who I've been working with a 30 plus years as well. I also worked at a management company called Violator, where I was under the tutelage of Chris Lighty. I went on toaticbuster Rhymes for a little while, who I met at Violator, I managed Miss. Elliott, while she was at Violator, and I managed to prove that Bob Deep before prodig she passed away. A couple about a year after they left Viator. I also ran good music, which was Kanye's first record label. I was the president of that for a couple of years. Amazing. I ran nightclubs. I owned a nightclub. I was the general manager, of a club that I was also a partner in called Biology Bar, where Don C was the assistant manager. I read another club called Dragon Room. I owned a club called Boutique. These are all in Chicago. And yeah, so I' been, you know, I've been in the business for most of my life.

GS: Amazing. You know I'm realizing, I'm gonna impromptu interview unless you're busy, unless you need to do something else.

JM: Nah, you what do you need me to do?

GS: Great. Well, you remember I was saying that I want to help you with your personal website?

JM: Yeah.

GS: Well, I think we can just I think number one is just like being able to ask who targeted questions from the flow. Great. This is awesome. How did you get into hip hop? What inspired you to do anything in hip hop?

JM: When I was very young, I wanted to be like, I was kind of going back and forth, but you wanting to be a doctor and a lawyer. And then I saw a movie called Crush Grules, which was the story of Death Jam and Russell Simmons. At that and that changed my life completely. I saw that movie in the next day. I decided that I wanted to do that. I wanted to be in the music business. I wanted to have a record label, I wanted to have a management company, I wanted to promote concerts.

GS: Wait, wait. Wait, Wait, wait, tell me about the documentary.

JM: It's not a documentary. It's a It's a film. It's not a documentary. It's called Crush Grs.

GS: Okay.

JM: It's like a, you know, it's like a fiction. It's like a, I mean, no, it's not fiction. It's real. It's based on a true story, but it's not a documentary.

GS: Okay. And what inspired you about that?

JM: Man, I don't know, bro. Like, I was so young, I can't really tell you. It was just something about what they were doing, just seemed just like the coolest thing in the world. And it's been a lot of ups and a lot of downs for me, but it has, you know, for the most part, been like a really great ride.

GS: Love it. So what was the first thing that you did once you got inspired?

JM: Um The first thing I did when I got inspired was I started a company called Offer One. In 1989, when I was 13 years old, with my cousin and my best friend, and we did I planned a party, eighth grade, graduation party at hip hop party. I went to this this church, and I told them that, you know, it was eighth grade project, that I was trying to accomplish by getting them to let me to rent out the church for an eighth grade graduation party, with an actuality, it was all alive. I was just a kid conning of church out of a space and a party. And that's the first thing I did, I dorew a hip hop party, made a couple bucks, got addicted, and went on from there. And the second thing I did was I got a internship at Def Jam Records two years later. When I was 15 years old, there was a program called Yes to Jobs for Inner city kids of inner city kids that wanted to get involved in the music industry. And I went to California, interviewed with Def Jam, and they accepted me and I got the internship, and I started internning for Jeff.

GS: What do you think it was about you that made people at Def Jam want to be wanted to give you a chance.

JM: And I was just so driven, bro. Like. I always thought I was grown. You know, I got my first job when I was 11. You know? I started my first company when I was 13. I got my first internship, when I was 15. I always thought that I was just grown. You know what I mean? I don't know. I can explain it. Like, I didn't I just I just was very direct. I was very focused. And I was just kind of hard to say no to. 'cause I was just, you know,W, I was just I was always hard working. I was always serious. I was always good, and I was always good at what I did. It was kind of hard to turn me down.

GS: So even from like early age, like you had like almost nothing on your belt, but, like, they were like, you know, this guy seems like he would do anything to make something happen.

JM: Absolutely. Because that's not how it seemed, that's how it was, Garrett. I would do anything to make it happen.

GS: And how would they know that without, I mean, what did you do during that interview?

JM: You would pick up all energy. I remember meeting Chris Ley in the late 90s and he came to one of my clubs in Chicago. And I just made it a point to take him around Chicago, take him to my clubs, you know, make sure that he understood how I had positioned myself in the marketplace and that I was really good at what I did. I was good at not only, you know, hustling and creating good products, but I was good at, you know, demonstrating to my elders that I was capable, you know? And if you could show somebody that you actually are capable, that's when opportunities open up for you.

GS: And so, who did who taught you, I mean, was it almost like an accident? Do you, like, who taught you to.. like, be like a to have that energy even in the first place. Like, or Or could you not even help it?

JM: Nobody taught me. I wouldn't say that I was taught or how to. Yeah, I mean, I. Nah, nobody taught me, bro. It was just instinctive. My dad, who I lost, you know, my dad died when I was very young, but he was a very big marketing guy at the first black company to go public. He handled all the marketing and sales for that company and was, where I'm from, in Chicago, the Johnsons are very famous and very, you know, well respected, because they literally, you know, my uncle and my dad built the first black company to bet trade it on this New York Sock Exchange. Right. But he died when I was five, so I can't say that he taught me necessarily. You know, I have my mom and my cousins and stuff would always say, oh, man, you're just like your dad. It's in your blood, blah, blah, blah. So maybe it's, you know, just like in me. Maybe. But I can't say that anybody really taught me. I saw that movie Crrush Groove, and the next day, I was just trying to figure it out. That's what happened.

GS: You know that the line? Yeezy taught me. That's. That's what came up. So obviously, you know, you built somewhat of a reputation of, I would guess, I would guess the reputation is that you would get stuff out and, you know, how do you develop a reputation? And what is the importance of a reputation?

JM: It's everything. I mean, you develop it by hard work and consistency, and the importance of it, it's literally, there's nothing more important.

GS: just say more. I just want to hear more about this.

JM: Oh, I'm sorry.. Yeah, I mean, what can I say? There's nothing more important than, you know, what your reputation and what you build, and you get your reputation from the work that you put in, you know, by working hard, by being consistent, by putting points on the board, all the time. And yeah, that's really what it's all about.

GS: And so what you know, for me, one of the most important things is, you know, when you say you're going to do something, you do it, like, would you agree? And if so, what.

JM: Without question. Without question. You got to keep your word. Your word is your bond.

GS: And it would feel like the importance of a manager for an artist is that you manage expectations with people that you do you help the artists do business with, right? The artist changes their mind a lot more than the businessman.

JM: Mm hmm.

GS: So you almost have to predict that even if the artist is excited about something right now, you know, given their track record, is it safe to say, hmm, let's commit to this business partnership? If you know that they may change their mind in like a week. Right. Have you learned a lot of lessons about that?

JM: Oh, for sure. For sure. I mean, artists changed their mind, like, the weather. So you just got to be able to be fluid, and, you know, go with it. You know what I mean? And learn how to adapt.

GS: I have to imagine that... with being in the industry, and having a reputation, often a good reputation, you still are massively misunderstood. Do you think that comes with the territory?

JM: Definitely comes with the territory. You know, and I've had a great success record, but, you know, I still get people questioning me from time to time and it's fine. I'm always up for the challenge.

GS: How do you discover great talent?

JM: That's a great question. There's no particular way or method. I think it's always about being at the right place, at the right time, and having the skill set to identify what's special. When I met Kanye, I met him through my boy, Lucian, Lucian Wasen. And they were in a group together called State of Mind, which was Kanye's first group. There was three guys in a group, Lucian Gene. Lucian Gene and Kanye. And I listened to all of them, and I just got cool with all of them. But it was just something just special, specifically about Ye. It was his production and his wraps. I was like, man, this guy can really make beats and he can really rap. And that's why I do these tours. Now, mind you, I was closer friends and still am. Closer friends to Lucian. And I'm cool with Gene. But Ye was who I locked in with, to try to develop and work with and propel.. How I met Virgil was completely different. My mor, one of my mentors, one of my main mentors, I got in Jay Boogie from Chicago, who I actually gave me my first paid position at a record label. Up until this point, up until the point where I worked for him in 1995, all my positions that Recolle was were unpaid. They were all internships. But he gave me a salary. And we became friends. And I started working for him in 95, running his label. I' each other in there. And 10 years later, he had a design studio in the South Luke and Virgil was an intern for him at this design studio. And at the time, I was running a good music for Kanye. I was running his freco label. And I was looking for a new designer, a new graphic designer.

GS: Oh, wow.

JM: I was looking for a graphic designer for a group called Sarah, which is a group from LA that we signed a good music. And Boogie insisted that I meet Virgil and that I give him a chance. And I had already kind of seen some of his work laying around, the office. And I was like, wow, these guys is really, you know, whatever this, whoever did this is really talented. So I met Virgil through basically through Jay Boogie and through his own kind of like intent of him leaving his design worker around, and then he kind of interns for me. He came to my house every day for about four months where he kind of interned for me. I had him working on different design projects, and then when I felt like he was ready, I introduced him to Kanye and the rest is his history. Now, if you notice, those are two completely different discovery methods. You know what I mean? Kanye I met through Lucian, which is just a friend that was just going to a show, and I was just like, damn, this guy's dope. And then.. Virgil, I met through my big brother, Jay Boogie, right? And he was Boogie's intern and then started to be my intern. And after the time was right, I presented him, but still the same goal, you know what I mean? Still the same bottom line. And I don't I can't say that one method is better than the other or more tried and true or whatever. I think, you know, just is what it is. I think it happens. Discovery happens all different kind of ways. So, yeah.

GS: A beautiful. What did you do What is your Well, I guess maybe instead of sitting asking the general question, Kanye is such a unique soul, right? How did you bring the best out of him?

JM: Um.. I think just by being supportive, just in general, like love, I would always just try to just be there for him and just support. Like, you can't make a guy like him make better beats. You can't make a guy like that make right better raps. I think you can make sure you put your arms around him and his circle and his situation and just be supportive. And that's what I think, you know, I've always tried to do, and that's why I threw the ups and downs. I think we still find our ways back to each other to work with one another. because the support has always been genuine and real.

GS: I mean, just, you know, maybe an unquestionable, loving commitment to each other, right?

JM: Without question.

GS: Hmm. And the same is for Virgil.

JM: Absolutely. Absolutely, yeah.

GS: So when Yes having a good day and let's say he's being. He's reminiscing on the past, thoughtfully. What would he say about, you know, you in general, but maybe even specifically the importance of the first few years of your support?

JM: Ah, man, it's hard to put words in his mouth, but I know that it would be positive you know what I'm saying? Like, it was always, I felt like I had an impact, you know, I felt like that, you know, since the early years of starting working with, you know, when I started working with him in like 91, 92, and then me bringing in Don C three years, three or four years later, we were always there pushing him forward. And, you know, just trying to make them successful and make him to achieve his goals, whether it was his first global tour to developing his globing lines, because he had multiple different globing lines. To working on, you know, the very ambitious film projects that he's worked on throughout the years. You know, we've always been there, so yeah.

GS: So with a lot of these projects, it wasn't just the first time your artist is something. It was also the first time you did something. I mean, that requires a level of fearlessness or even if you had fear, you know, pushing it through, right? So how do you have that, what's up with that mentality?

JM: ask the question.

GS: So with, like, fashion lines, with ambitious film projects, you know, inevitably, you end up with something that you haven't encountered before, right? How did you. You know, how do you how do you do something you've never done before? And how do you support an artist to do something they've never done before?

JM: You just close your eyes and leap. Jump in the pool.

GS: What was that I was just looking at on your phone? Hmm? Oh, no, I'm talking to somebody else. Well, I guess I like that answer. Also, I'm wondering, you have such a great network. Do you if someone in your network has done something at all similar, you know, you give them a call, you're like, hey, this thing's we're trying to do this.

JM: Yeah. Yeah, I'm asking. That's your network is for to like reach out and see who can add value and benefit from a situation or scenario. Absolutely. We got a great rolodex and Yeah, absolutely.

GS: So, everyone has only so much time in the day. How do you decide, you know, what calls you pick up?

JM: I just prioritize him by importance, you know what I mean? Like, I can't answer every call, but if there's, you know, you know, real business and an opportunity and, you know, something that re value. It doesn't have to be about just business, because if it's a family car, I'm going to answer it regardless. It't have to be about a dollar, you know, because it's a family, you know, more important. But I do I do prioritize, I don't answer all my calls.

GS: Makes sense. How do you how do you deal with like relatives and old friends at expect things from you? Like, probably unreasonably, so.

JM: Um. How you try to be polite? I just try to be polite.

GS: Do you try to be straightforward with them and explain you know, why you can't help them, for example?

JM: Yeah. That's good. That's like a teach a man how to fish type thing.. Like that..

GS: Yeah, sec. I was the right now for like 40 minutes. So, I really love that you. You quickly appeared to me as someone very serious about an education revolution.

JM: Yeah.

GS: Just, you know, even briefly, can you talk to me about why it's exciting to you, about the prop?

JM: Because it's necessary. It's absolutely necessary. We need our little boys and girls, especially black and brown boys and girls. We need better education, better real training for them, so that they can have a shot. Right now, we're last. We're in last place, bro. And the only way that we can change our scenario is through education.

GS: Yes. And the concept of AI, assist, Montessori.

JM: You got to remember, bro, I went to Montessori school. I know how dope it is. I love that style of education. I would not have been able to survive in a traditional education system, not me. So when you said it's an AIisted monessori school concept that we're going to take around the world, come me in.

GS: Yes. I love it.

JM: What are you talking about? My cousin Don C, his daughter, his oldest daughter, Gia, who just graduated from high school, went to Montessori school.

GS: Well, look..

JM: She went there kindergarten through 12, bro.

GS: Well That's my sweet That's, like, my little niece.

JM: Like that we're all about myessori. So you didn't even know it, but like, when you said Montessori school to me, you had already was like, I like, you're speaking? You're speaking to me.

GS: Well, look, I'm always, like, surprised when people are not, actually do things that make sense. And like, that may seem like a funny thing to say, right? But you get it, right? Like, people people do things that don't make sense. They waste their time on issues that don't make sense. Approaches that don't make sense. And like, you know, at some point, you just lower your expectations for people in general so much that when people do things that make sense, you're surprised. Right.. I guess I have been pleasantly surprised by your logic. And it's not about you. It's just like in general, like, I'm so used to people doing things backwards and prioritizing useless things that whenever someone gets what makes sense, I'm surprised..?

JM: Yeah. Hello?

GS: Yep.

JM: Yeah, I'm sorry, though you were kind of breaking number.

GS: No worries. Do you feel like your network is full of people that. would be able to get what we're trying to do. I mean, I think to you and me, it's pretty obvious. The AI assisted Monaster. AI supercharged Monessori, right? Like you feel like you feel like people, for example, hip- hop legends would understand the value of of revolution.

JM: They might not understand at the gate, but we can make them understand.

GS: And how do we do that?

JM: Talking slow.

GS: Can you elaborate what that means?

JM: Just explaining, taking your time, going point by point, and making sure they get it.

GS: Okay. And that's what you've seen in general when trying to build, let's say build movements, right? Where it's a whole paradigm shift. You, I guess your advice to me me and us is to not feel above explaining things that may seem obvious to us.

JM: Right.

GS: And then that's really just being Christ-like, right? Like being humble and patient.

JM: That's right.

GS: And loving, right?.

JM: That's it.

GS: Do you. Did you see value in the event that I put on on Wednesday?

JM: Yeah, I was super cool. Great group of people, man. I met a lot of people.

GS: What do you I've changed a bunch of phone numbers. 100%. What How would you describe that event? A room full of. Well, an open space full of, right?

JM: Yeah, an open space full of people that want to shift culture and make change. and have real. It felt like it wasn't driven by commerce, that it was that their intentions were driven by change. So that was like refreshing. I didn't feel like I was in a space full of people that were trying to come up.

GS: Oh, interesting.

JM: Like I felt like I was in a space full of people that were trying to make change.

GS: What was, and I want to get more to how you thought about the MM, but what what's another example of a space you've been in that felt like really about change?..

JM: Whenever I used to go to the mosque, with the nation of Islam, as a kid, I always looked at them as brothers in the city, on the south side and west side, on the front lines that are for our people. I look at them, and I just felt just positivity from them and whatever. I used to go to the m. I just feel that same kind of energy in the road. Like it wasn't about, they weren't there looking for a dollar. They were looking to support our people and support change within our community.

GS: Well, it's funny because, Hey, a gentleman, I brought him up briefly yesterday by Danny, J. Bakewell, Sr. He.. He was one of the leaders of the Nation of Islam. And he asc very quickly, I think because he believed that it could be a force for real change. In a lot of ways, it has been and it is. And he was. I was I'm like looking, I'm just looking at his bio. He helped legitimize moving that turned gang members into Peacekeepers who helped tamp down violent crime in like Compton, etc. And he eventually became the largest black commercial real estate owner west of the Mississippi. And so he wants me to do his biography whenever I have time. And I think it's. I think it's. You know what I think it is? I think people can tell that I want to just take what they built and run with it in the best way. Like, I really, I know I would be nothing without the Giants, right? In every every space, right? Whether that's you're a created music that's better than any coffee, I could drink, right? Whether that's you illuminated how you can organize people without spending too much money, because resources are often very sparse. When you're actually a revolutionary. And you know, I find it so interesting that you brought up the Nation of Islam because when I was praying and meditating earlier literally yesterday morning. I was thinking about... Who do I aspire to be a combination of? And what I said I shared with you yesterday was Malcolm X Bruce Lee and Clarence Avant. And I just feel. You know, I almost want to I'm tearing up almost, thinking about Malcolm because.. Can you hear me?

JM: Don't you down, turn down the interest in. Hold on

GS: When I think about Malcolm because, you know, well, he paid the ultimate price, right, for his community and the world, really. And I's, I don't want to be I don't want to be a martyr, but I will be happy to be. I think that's. I don't know. I almost feel like that's what that's just what you need to do as a man that stands up for something. You have to be willing to die for something. That's my view. I'm curious what you think about that.

JM: Yeah, you got to stand for something or die for anything.

GS: You know, what speaking of Clarence Avon, you remind me a lot of him, just from, not that I knew him, but I watched the Black Godfather. And that really, really moved me because, you know, in a different way, he was he was also a by any means necessary guy for his for the black community. And I'm curious how much you've thought about that parallel between you and Clarence. And, you know, what I suspect is that, like, there's just no way that you're gonna be able that anyone that even seeks to do anything similar to Clarence can do it without a deep humility, and keeping the mission above their ego. So I'm curious, just anything I said, like, what your reaction is that.

JM: Yeah, I' male. Clarence was for his people, and I'm for my people. He's definitely had more of an impact than I have on the community know what I'm saying? I could have only wish that I could do a tentively he's done. But yeah, I'm for my people to absolutely. So that's the parallel I sleep..

GS: Right. And you have many, many years ahead of yourself, which is great. So we can get creative about how people you know, 50 years from now are like, you're the next job Monopoly, and then they're not even talking about music management.

JM: Right, right..

GS: So what is What is the value of events for movement building? Like the right kind of event that brings together good energy and diverse people for mission. What's the value of a good event for movement building?

JM: The energy, the movement, gettingting the right people in the room to have diogue around, how to make change is important, you know? That's how change is made by putting the right people together to discuss it, strategize around it and put together plans, plans of action, allow how to move things, and how to make change.

GS: Right. And so it creates like this energetic field of this frequency of urgency and really optimism, but also like a recognition that action is what this is about. not, you know, getting on a stage to bviate, to just say a pre canned sort of thing that you say everywhere. It's like, you know, you're either gonna step up or you're not, right? And if you're here, if it's the right event, it was already curated from the start about who shows up. Who was invited to show up, but then who actually shows up is also another indicator of who's serious and what at least what I've found as someone that has such limited time. And literally, John, I'm not, you know this is true. I had zero seconds of free time yesterday.

JM: It was No, I know.

GS: Zero seconds, and that's a great sign to me. that whatever Big Bang happened on Wednesday that was continued on Thursday and will continue forever, if you just stay, obedient. that worked, right? It just, you know, if you get the right people in the room that you know, will then be not just representatives, evangelists and activators in their own unique way.. Just got to stay in the spirit and be, you know, both mission focused and opportunistic about capitalizing on that momentum and building more and more of it. And so what we talked about John was working together on creating the next events, following this First Supper, right? So what about that feels useful to the movement? And what are the kinds of people that you want to bring to the table when we do an event in Chicago? Let's just say, let's start with these two. Chicago and Compton. What how do you hope to leverage your tremendous, you know, credibility, etcera, to like, well, there's a bunch of questions, right? Would you agree that you want to work with me on putting together follow-up events?

JM: Absolutely.

GS: Okay, and then, what do you, why is that relevant to the movement? And I ask these questions not because.

JM: We got to keep these events going so that we can create an army. We need to change army

GS: And I mean and it's what's always been the case, right? You need to create activating events that fill the room with the Holy Spirit, honestly, right?

JM: You said what? It's always been the case, as well that in order to build a movement, you have to fill the room with a spirit of urgency and, you know, really, like a divine urgency.. And, um, so John, what what is the importance of an invite coming from John Monopoly versus, you know, a random, text from someone, oh, I found you on LinkedIn or whatever. What is the value of, let's say, his name's Harry O. His nickname's Harry O, right?

JM: Yeah. So what is the value of Harry O getting an invite from John Monopoly versus some random person that called emails Harry O?

JM: Well, if you saw when he peeped me on the camera, he smiled and said, "John, you would prefer that the person reaching out to your invited guest has a relationship with them, and it has respect from them. You know, is respected by them. You don't want a call call, especially not for something that're gonna eventually need real work to support, and maybe some type of monetary support as well. You really want to be as personal as possible.

GS: 100%. And I guess it's almost it's just obvious to us, right? You know, someone that is credible and interesting and well known, even in a particular, you know, industry, they're getting hit up all the time, right? Is that correct?

JM: Yeah.

GS: And so an invitation, a call to action coming from someone they've known, let's say for decades, matters.

JM: It' totally and not just known, maybe you've done business with them for decades, too, on and off, right? And you are happy to do business with them or activate with them, right? Like reputation and past experience matters with that person, right?.

GS: And so, it's a safe to say, if John Monopoly is helping build a movement where black people are helping lead the way, but also, you, your network's not just black people, but, you know, it's the same to say that you could be a really big asset for that movement.

JM: A huge asset. But let's do this. I'm exhausted. I got to go to sleep. I'm gonna call you when I wake up and we'll continue this, okay?

GS: Okay, sounds good.

JM: All right, bye.

GS: All right, see you.