Rich Kleiman from bookie to power player in sports & media partnering with Kevin Durant| The Pivot

At some point in your life, you was thinking the craziest things. You just happen to achieve it. But you have to think that way. You start telling yourself a story of what you experienced. It's your truth. It's real. But it's a story. There's a big difference between emotional sensitive. Like I'm just trying to cope. So I'm trying to tell myself what is happening. That was my way of escaping it. But it gave me no discipline. It gave me no direction. Casino was my favorite movie. Like Ace Roststein was my favorite character. So I was like, I'm really about to live this. Like I'm going to do this [ __ ] in meeting Jay. How was that relationship built? >> His music was a blueprint for people, but just watching him and watching the way he spoke and how practical he was about certain decisions. >> Everybody always talks about their home runs though. But Aaron Judge strikes out, too. >> I was that guy. I talked about that [ __ ] all the time with everybody. I probably won't be remembered in a 100 years for anything unique in terms of what I brought into the world. And that's a thing to think about. that Katie meeting would turn into a lifelong friendship and business relationship. >> But I had never had anybody that good at anything that important in this world ever. Family, friend, coworker, nobody that believed in me the way he believed in me. It's a long road. So like the pivot was not the sharpest cut. >> It got my people got me up on a mission. Got me up blowing me I got the key on this vision I can trust trust limitless take me it here to witness it my people feeling >> oh that boy salter in too >> y already see the >> up dog he clean today >> mama I made it >> well Mike Jay's got Kobe outnumbered today RC >> it's all good man Jordan should always have Kobe outnumber >> I'm wearing the old and all white lows. No, >> but they go with everything though. Rich, >> of course, man. Everything. >> They go with everything. Welcome to the show, Rich Klein. This is Fred Taylor, Channing Crowder. I'm Ryan Clark. Pivot fam. Thank you for pivoting with us, man. Your story, bro. Just when I got an opportunity to dive into it. Just always an entrepreneurial spirit. Along with that spirit though, always a genuine, authentic person. It's why I was drawn to you. It's why Kevin Durant says he was drawn to you. It's why you've started businesses with him. But I got a more important question. I need to know the story of Tom Kilman. >> Wow. >> So tell me >> how Tom Kilman ended your basketball career. >> Wow. >> That's crazy. That is so crazy. You know that, man. So I wanted to play basketball as a kid, but I knew in the back of my mind, right? Like you have to have a bit of delusion to do anything in your life. I'm sure for you guys at some point in your life like you was thinking the craziest things. You just happened to achieve it. But you have to think that way. So I knew though I wasn't good enough to play. You know what I'm saying? But like I wanted to be in the action. So anytime I went to play anywhere, like even when I played well, I remember I shot the lights out at this AU tryyout at Riverside and I didn't make the team. I'm like what the like I I was like seven for seven from three, but I was like [ __ ] this isn't it. But I got invited to this camp and I got there and everything was written down on on on pencil, right? Like so the team they would list the night before and it was NBA, NCAA, and NIT. And I'm like, if I don't make NBA, it's a wrap. Like I can't be at this camp and playing. I had two of my friends with me that were clearly like D1 players. So I go up to the board, I'm like, man, I didn't make NBA. So I'm like, let me look. I'm on NCAA. I didn't make NCAA. I look at NIT. I'm like, what? Yo, did I not make a single team at this camp? Like, what the? So, I went to the guy. I'm like, yo, I I don't think I see my name on there. He's like, uh, looked at my number. He's like, "No, you're on there. You're on there." I went on there. I'm looking through. Every name's checked off. I'm like, "Tom Kilman. Wonder if these guys think my name is Tom Kil. What the? I can't be Tom Kilman senior." I'm like, I'm Rich Kleman's sophomore. They got me down as Tom Kilman senior. So, that night, I tell everyone at the camp like, "Yo, they [ __ ] my name up. The whole shit's crazy. The next day, our team starts scrimmaging. Dudes are like, "Tom, Tom, Tom, Tom, Tom, Tom, Tom, give me the rock, Tom." I started correcting people. No one cared cuz I wasn't nice enough to care. So, the rest of I spent four days at this camp as Tom Kilman senior. And that was it. I knew I was not going to get recruited. I didn't even exist. And that was it, bro. And I went I went home and I the one thing I realized when I got home though was I didn't want to be away from basketball. So, like I kept playing, but I knew right away I wasn't going anywhere. >> Yeah, man. I just thought that was so funny when I saw that. I want to, you know, I hate to like make people tell their story chronologically, but I think this is important for your story. I feel like New Yorkers have this state of mind and this entrepreneurial hustle spirit that's different than anywhere else in the country. And being here more often, I get to see it. Bro, you used to sell action figures, get programs signed and sell them. Where did that hustler brew from? Or where was that breed in you that it was so ingrained? >> Well, first of all, I think you're right. A lot of it is like unless you want to live in a bubble in New York City, right? Unless you want to be narrow-minded, it's hard to ignore the different walks of life and like the perspective. Like if you walk with your eyes open, you'll gain perspective on any street. Like in New York City, you could be on Central Park West on 83rd Street and then you could walk two blocks down and there's projects on 83rd Amsterdam. That's just the way New York City is, right? And you could be walking in the best neighborhood in the city and somebody's on the corner of the street like with boxes over them. And my uncle was homeless and he lived in California. And it never made sense to me cuz my dad like, you know, my dad worked. he was moving around a little bit and I figured like well how would this meant like how would my uncle be homeless, right? So like that coupled with looking at these people in the city always made me realize like I'm not about to have no money in my life. Like whatever it is, I'm not about to have no money. I do not want to talk about the stress of money, the the the arguing that went on in my house about money. It was so ingrained in my head that like money was nothing but stress. and then look what happens if you have none, right? And that for me always just put this fire in me to make sure that there was a way that I could figure out to make money. And I remember even when I would go to the hot dog stand or the news stand, when I saw them take that knot singles out to give me change, I was just mesmerized and I felt like that was his [ __ ] Like that news stand was his [ __ ] So I first was like, how do I create my version of that? It was just like looking around my room and it's like if it wasn't some >> late '8s, early '9s Nick [ __ ] I was selling it like whatever it was. So if someone bought me something, I went right downstairs, set up a little thing in front of my building and I would just like I would figure out how to make any money and and it wasn't even about like negotiating. I'd be like this $10 like I'll give you two. I'm like deal. I'll take it. I just want any money for anything that I have out here. >> Yeah. that that just and it also gave me like a sense of validation my home life and I've been talking about this more at this point in my life because you know when you grow up I don't know if you guys feel this way like you start telling yourself a story of what you experienced it's your truth it's real but it's a story so like how you talk about other people is the story and then you sometimes lose track of like man what what was really going on like I'm just trying to cope so I'm trying to tell myself what is happening right Right. >> Then you get older and you're like, damn, the story is a little different in my mind now. So like the more I've thought about it, like it was just so chaotic for me at home that looking for some validation and looking for some purpose and meaning was like something I desperately needed. And sports gave me it. And being around people like being popular, being like known, you know, being known was a thing in New York, right? Like being able to walk wherever I wanted. That really made me feel good. And just having something that I could like sell or be a part of all that gave me some validation. >> What was that chaos though? Cuz And how did you get out the streets? Because a lot of people that same story chaos at home and now you had to find something to do and a lot of times you go left with it. >> Yeah. Well, the thing is is like I you know it's interesting. I I was a middle class kid in New York City. Like I was I was privileged in in some regards, right? And there was people with more and there people with less. And in that day and age there was a real middle class. Like my dad worked in construction. He had an interior design business and like my dad always had beautiful suits on and was wearing a ascot and was like a G. Like I thought my dad was always cool. >> That doesn't mean you're making a lot of money. You just he could work. He could have a living. And and in the 80s and 90s in New York City, what you could do with that type of living was like I could get my kids to private school and you know I could take my kids down to Florida for a vacation and you know I could live in a good in New York City. I could live in a in a good neighborhood. And there was there was kids that were really really wealthy that I like didn't really understand at that point what the difference was. And then I had a ton of friends that were living in boxes. And I never really saw any of it about money though. I saw it about like where were they happy because in my house I wasn't really happy. Like I was happy when my friends were around me. I was happy when I was out. But my parents fought like out of the like out of the movie like out of the show Cops like straight up like in each other's face throwing [ __ ] across the house throwing [ __ ] at everybody. My mom was erratic. >> My mom would sleep all day. She was wild. And when my dad left, my brother left at that point. And at that point I was like, I can't be in this house. Like you know she was always unwell mentally, substance abuse, always unwell. Like and all I wanted was her to be well. Like all you want is your mom to be well, right? And I just tried to >> push her to see that like, yo, it can't be that bad. Like just come on. Like go outside. It's the sun is shining. But she never could get her life together ever. So it was like stay in the house or go out. And the only people that were out during the week, the school week, were people that could chill. So I just went out and made a whole other like breath of friends and a community for myself. And you know, that was my way of escaping it. But it it gave me no discipline. It gave me no direction. So like that for me was really my oxygen and my currency was I felt like the more people I have around me, the more people I know, the more different neighborhoods I can go into, the more parties I get into, that will give me what I need right now at this point in my life. You know, >> Rich, I want to take a quick second. RC always cut the room in half when he talking championship. I think he did it with KD >> on cuz neither one of y'all have one. >> Right. So for BBM month, I want to cut the room in half for with me and you. Beautiful ball men month. >> I didn't know what that meant. >> Beautiful men month. >> Beautiful ball men month. >> What month is that? >> That's this month, man. That's not a month. >> This month. >> You just made it up. >> It must be honorary for our show. >> It's really every month for us. >> Every month, right? No, >> you wear a hat all the time, Rich. You You rock yours proudly. >> That's all I got. >> No, the real question is one semester. That's all you can give us? Boston University. >> I I got up to school and I remember laying down on my dorm bed thinking like, I can't do this. Like, I'm not going to I can't do [ __ ] Like, I can't go to class. I can't do this. I got into one school. It was this like general studies program. And I remember when I got there though, I thought to myself like, well, hold up. There's like a whole new crop of people I can get to meet here. Like what what value is not not in a transactional way like those relationships? I wasn't thinking about people around me at that age of like what are you going to do for me? It was just like I just want to experience like life and and and and get out of chaos and anxiety and just like be happy and be and be inspired by people around me. And I loved music. I loved sports. I loved partying. I loved being out, right? I did. I just liked being in the mix. And when I got up to school, I was just like, I can't do it. Like honestly, I don't even know how I graduated high school. From 8th grade when my father left and I was home alone with my mother. I did not do [ __ ] Like I I went to school every day because who wouldn't want to go to school? I wouldn't want to be home. I wanted to be around everyone and I wanted to play I wanted to play basketball. You have to go to school at least to be able to practice playing in the game. But I just got by. I just got by like Right. So by the time I got to school, it was like I can't do this [ __ ] >> You think you would have been better if he wasn't running numbers in back of the room. >> If you wouldn't being a bookie. >> Nah, I think I would have been worse, man. >> But what's that mindset though? Like was it were you just at a point where you just thought to yourself, you know what, I can't do this, so let me find something that I can do while I'm here. >> Yeah. Well, the thing was is like I went to this to this sports bar with a kid from the city who had already been up in Boston. He had a bunch of friends with them and it was the Yankees Mariners in 95 and it was all New Yorkers and everyone was trying to put a bet in on the um Yankee game and everyone was like, "You got a bookie, you got a bookie." And I was like, "Yo, I I got a bookie." I'm like, "My brother who was living in Atlanta at the time, I knew he was gambling." So I called him and I was like, "Yo, I'm going to put all these bets in with your guy." He's like, "Ah, my guy cut me off." I'm like, "Motherfuck, I just stole all these dudes. I'll take their shit." And he was like, "Take them." And I was like, "What you mean?" He's like, "Take them." He's like, "I don't even think the Yankees can win tonight anyway. We're me fans." So I was like, "You know what? [ __ ] it." Like the way I thought about it is like, you know, that's what gamblers do. I'll figure it out tomorrow. Mhm. >> So I took everybody's bets and the Mariners won and I was like that was like maybe on a Friday or Saturday and that like Monday everyone paid me, right? So I really didn't think I was going to keep this going. Come Sunday, phone was ringing and I was like, "Holy [ __ ] these guys really trying to put bets in with me." I went downstairs to this like supermarket. I got a composition notebook >> and like Casino was my favorite movie. Like Ace Roststein was my favorite character. So I was like, I'm really about to live this. It's like I'm going to do this [ __ ] And to be honest, the principles of having some discipline to like this sounds crazy, but like to get up Sunday morning to take the bets, to organize everything, to know when I have to lay off a bet, >> you know, to figure out if I had too much action on one side, to make sure I could collect all week long, keep my book straight. It started to give me a bit of an identity of like, all right, I'm doing some [ __ ] here. And like I knew in my mind that that's not why I was there. But like now I'm out of my house. I'm living in Boston. I'm running this book. I'm making money. I'm hanging out. Like this felt like college. Like I was like, "This is incredible." But then things started clicking like, "Well, how can I how far can I take this?" So like, you know, I started setting up other colleges that would send me bets and I would take, you know, a piece. So people would run for me at University of Miami or run for me at Wisconsin. And I had so many people gambling with me that I had to go get like the security guards at the clubs to collect for me. I had a kid pull up with a te with one of those old projector televisions cuz he couldn't pay anymore. And a lot of these kids would just keep doubling. They'd be like, "Yo, let me double. You mind if I double on Sunday night?" So, I just kept it going. And I remember at the end of that first year, my father was like, "You you I'm not about to pay for you to be in college. Like, you dropped out of school in a semester. Like, it's a lot of money to send you to school." And I was like, "How's this? I don't need a dollar. I'm good money. I'm gonna stay up here in Boston. And I stayed up in Boston. And the second year there, I I just full-on ran my book. >> What did that decision to drop out? What did that teach you about betting on yourself? >> Well, I don't think at the time that I dropped out cuz I was betting on myself. I think at the time I dropped out because internally I was spiraling a bit because in my opinion, I I had to, you know, fight or flight, right? Like with all due respect to my brother, when [ __ ] was ugly in my house, he used to just leave. >> I stayed right in the middle. Bop. My mom's sitting here coming at him. My father's screaming at her. They're throwing [ __ ] I'm just like, "Hands up on either side. I'm trying to make sure that like I could put this to bed. I'm going to navigate this." >> And then even after my father left and my mom was a mess, like I tried, like I really tried like to explain to her like life could be better. Like you don't have to do this. But, you know, addicts will deny it. So, they're just telling their kid like, "You're yo, you're bugging, like telling me like what I'm seeing isn't real." So, like, what I saw was real. And I I I watched it firsthand. But it was so messed up that when I got to school, it was like a release in terms of I can do what I want, but I couldn't necessarily like turn off the the what was inside and and what I was experiencing. So, like I dropped out of college cuz I just couldn't do it. In hindsight, it clearly gave me this understanding that yes, I should always bet on myself and yes, I'm always going to be okay. But it's funny because when I speak at places sometimes, like I was on a panel at Duke once and the person that spoke before me went to Harvard and and Wharton, I think, and he starts telling all these kids in the audience that I don't even look at college degrees. I don't think the best candidates for jobs are kids that went to SC to college. I want these people that have hybrid minds and these entrepreneurs and I'm thinking like you sound like a dick. Like you you went to college, you're successful. That's not what you're supposed to say. I was on at the next panel and I'm like I dropped out after a semester and one of my biggest regrets is I ain't finished college. How's that? Not because I feel like I missed out on anything in life, but because like the idea of finishing something, having enough discipline to start something, being regimented, those skills for me took so long to develop >> that I'm like, damn, if I had really developed these things earlier, like God knows what I could have done at a different pace. I wouldn't want to do it again. But I I think, you know, if anything, I feel like I hate that I didn't finish school, to be honest. >> Yeah. So, what is your because you're a very successful man, >> but you're a college dropout. >> Yeah. Say uneducated. You don't have, you know, you're one semester. What's your superpower? How are you so successful? >> It's funny when you say that. I'm always going to be wired to feel like um maybe I'm not right. Like I feel like I know that I have continued to accomplish more year over year. And that's kind of like the way that I set my goals for myself. Like as long as that arrow is pointing up and as long as like I feel like what I'm doing is quality and that my relationships are intact, I'll compromise money for for, you know, good energy. I'm not about to be around bad energy. And I'm not really just going to [ __ ] somebody over to make more money. So, you know, I have to stay at my pace in everything I do. And I know that I have a a certain taste and a certain ability to like envision things and then try to put them in motion. So I think that I had an understanding of people at a really young age and I could relate to anybody in any walk of life and I could talk to anybody and I could navigate any situation. you know, later on in life when you start thinking about business deals and you start thinking about like, you know, having the gall to do something, a lot of it is how you position and how you communicate it and, you know, and and how you surround yourself with the right people. And I think that those type of those type of things were things that I did have a real education in, >> you know, and also, you know, if you think about the world that we are all living in now in this like sports and entertainment convergence, you know, everyone wants in now. Everybody. So like there's a lot of people that I've watched that have made so much money, right? They come up this way and then they come in over the top of it. So now it's like, yeah, I want to be in sports. Like I'm a billionaire. I want to be in sports. or you know I'm a billionaire and I want to be in the entertainment world and that's cool that's great and and they they may be able to understand it but in my opinion I'm native to it like I grew up and that's what I loved and what I studied and you know my knowledge of sports as a young person made it so seamless for me to be able to dive into the sports world you know the music business was more complicated for me in terms of like I love music but I wasn't about to like want I didn't want to sit in the studio for 14 hours making albums [ __ ] I want to get on to the next deal and stuff, but if you put me in a gym or you put me at games or travel for anything sports related, I knew that I would do that like every day of the week. So, I think that it's that EQ a bit. And as I've gotten older, I'm more patient. And I think like adding all those things up with like my journey, like you know, I always say to people, I felt like I was a 10th man on a roster. I was an eighth man on a roster. I feel like I was a sixth man of the year. I feel like I was named a starter. I feel like I made an all-star game. I feel like maybe I made a third team allNBA and like I'm still trying to win MVP. Like that's how I look at it. And I definitely didn't I wasn't the first pick out of the draft on the draft. >> I love that. Now that I love that because that talks about continual and steady progress and I think so many times people want to be overnight successes and with the way that your face is seen now you know 35 ventures and boardroom all of these things it's like man he just popped up on the scene and he's a star and people forget it takes years to become quote unquote a overnight success but a lot of things in life too rich is relationships right there are so many people who can go to Wharton or can go to Harvard who can't have a conversation, who can't make people feel comfortable, who don't understand how to blend in to every room. You know, you're you're in music and you get a part you get a chance to be a part of Fade to Black and that parlays you into Rock Nation. In meeting Jay and having conversations, how was that relationship built to where you got to be a part of Fade to Black, but then also move into working at Rock Nation? Yeah, I look at like my career now and it's funny. This kid I spoke to last week was asking me, you know, he wanted some direction, right? Like it's just a odd thing to ask somebody, right? Like give me direction. And I know what he means by it, but like for me it was like um what's happening now is you know there's so many stories of these unconventional paths that people take or so you think they're unconventional that people think that if they're on some type of path that feels somewhat traditional in some sense that like they're wasting time. And I said to this kid, I'm like, you know, you been out of school four years, you've had two job. First of all, you went to school for four years. You've had two jobs. the second job is better than the first job. Like you just got to start stacking wins, right? >> When I look at my career, it was like I weaved this web and I I did have it in the back of my mind. Like every play I saw the next play, but I might not have seen two plays ahead, right? So, I ended up in the music business managing DJs and and producers because I was working on that show, The Life, on ESPN. And I was the music supervisor for it because I wanted to work on it as a producer, but they didn't have a role as a producer. So, I had to do the music on the show. And there was a budget for the music and I didn't want to spend all the money. I wanted to keep some of it. So, I built up this library of unsigned artists. ended up putting this theme song together with Styles P and Farrell Munch and I was like, "Oh, I'm getting my feet wet in the music business, which led me to managing, you know, even more producers and more DJs." And then I started a label. And as I started this label, I'm like, "Oh, look at Jay-Z. Like, look at this world in music. Like, holy [ __ ] like that's where I need to go. That's what I want to do." So now I'm managing this kid, Mark Ronson, who was like the biggest DJ in the city, became one of the biggest DJs in the world. And we're like flying to Tom Cruz's wedding and Calvin Klein fashion shows. I'm just like going into this whole new world now. And I'm starting to see it, right? Every room I'm in, I'm like, "All right, this is how I got to go. I've got to move this way now." So, we go and do two record deals. We have all this talent in our studio down in Soho and Amy Winehouse comes to record Back to Black with Mark there. And I'm just watching everything and watching everything >> and I ended up meeting Jay-Z's manager, John Manily, at the time. and him and I spoke and brought him to this company, Radical Media, where I have been doing music supervision. So, it's like anyone I worked with, they stayed in my portfolio. There was always like this is part of who I am. This will play a part in something in the future. Let me keep all of these relationships like together and figure out where the value goes. And you know, that company ended up producing Fade to Black. I was able to act as a producer on the film because I had brought it together and I quickly started to learn that world. Like I'm sure you guys feel the same thing. I mean like you probably think there's nothing you can't do. Like really, right? Like anything that you're about to try and I know that sounds cliche but like a lot of people can say it and it sounds like [ __ ] Like I really think that I can figure out more or less outside of maybe have you know being a surgeon that I'll figure it out. Like I will figure out how to do this. So being around that film, there was this thing that was like, do this halo around this man and this like greatness even though I'm entrepreneurial and I want to do my own thing. Like hold up, like this throughine is is taking me here and like I'm just going to be around this for as long as I can. And you know, I always say that like I never really had in my opinion like a traditional mentor. you know, I didn't have like a coach maybe like on the staff that put their arm around me. And the mentors for me was like who I could observe and who I could watch. And if someone gave me enough access to let me watch them, then it was on me to take the game and like take what was available to me. And his music was a blueprint for people. But just watching him and watching the way he spoke and how practical he was about certain decisions and and how um calm he he remained and and how important like every detail was tastewise and you don't just make a flyer for a party, right? Like everything has to be thought out. Like I just was able to gain so much from that experience and you know that shaped me in in such a way that like you know I couldn't do what I'm doing now without that experience. But that whole era, you know, if you think about like how I've tried to build boardroom, you know, I look at those '9s rap labels, they were so powerful, right? Rockefeller, Bad Boy, No Limit, Death Row, because it was like it was like a sports team. You wanted to be down with the entire thing. >> Wear their clothes, drink their alcohol, go to their parties, listen to the music, watch the films they made. And that power of that brand like there was the talent at the center of it but it was like the brand became the way you feel about like your team >> and to me that's like the stickiest businesses that that can connect like with a community that way. So it was that whole era and that whole time in in New York and in the music business and then obviously being so close to those guys that really like helped shape me. >> While I introduced you to Katie >> Yeah. Did you think that that meeting would turn into a lifelong uh friendship and business relationship? >> No. >> So, how did it all? >> Nah. Nah. But, you know, cuz Wall was like, "Yo, you got you got to meet KD." Uh, he's in the city getting his like rookie of the year trophy and he wants to go see the Jay-Z show, right? And I'm like, "Of course I'm meet K. I mean, it's KD, right?" Like, he was already KD. KD soon as he touched on that court to Texas, like we all knew who he was. But I do think that like any business partnership or any relationship, it's like I'm sure there's a time where the three of you all met for the first time. And like if you could like go back then and go imagine the two of us were like, "Guess what guys, we're going to host one of the biggest shows in the country. Three of us." You'd be like, "What?" Like it would sound crazy, but when you really dissect it, you'd be like, "Man, we did really always [ __ ] with each other. like we did always really understand one another >> and you know I don't think it's any different with a marriage or a business relationship like what that is is maybe hard to put your finger on but I knew when Kevin and I first met it was like yeah like I really [ __ ] with this guy like I get him we we're different I'm loud and and you know I have I walk in any room and just talk and KD's a little more introverted at times but we just kind of like we're comfortable with one another as friends and then on top of it I I've always gravitated uh as most people do, but I to greatness, you know, and and to somebody that has honed a craft in in such a way that like is rare in to to those people, you know, to to you guys too, like to get to the top of that and and and to to know what goes into all that. So, you know, our relationship in the beginning was really connected around just like I loved basketball and that's what he wanted to talk about, right? So, you know, so we could talk about that and stay in touch and and while was somebody that was really important in my life, still is. And you know, I think for Kevin, that was at least like, all right, cool. Like, I [ __ ] with this guy. W really [ __ ] with this guy. He works with Jay-Z. Like, these are three great boxes to check. Like, you know, so we stayed in touch for years even before we worked together. And >> everybody always talks about their home runs, though. But Aaron Judge strikes out, too. >> Yeah. But they say, but they say you went or you learned. What are some of the what are some of the misses? What are some of the bad entrepreneurial angles you went through that you learned from? >> You know, I always say I don't I don't think I'm sensitive at all. I think I'm emotional, right? I think there's a big difference between emotional and sensitive. And and the way I I grew up, you know, I had to be loud to get my point across at certain times. and and um you know the verbal kind of like sparring that went on constantly you know made me reactive in some ways and I think that it wasn't necessarily like a mistake that I made. It was more about how I showed up in my own mind earlier in my career and in my life where I'm like I didn't really have to handle that situation like that or react in that way or take it the way I took it, you know. when when you get older and you start to realize like damn if I really just impose my will and advocate for myself you know a you can sleep well at night whether it works out or not but b you know if you're good most of the time it will and if you're clear and I think that a lot of times like my my intent was really good but the way in which I approached it at times you know really impacted the final result or impacted relationships you know and one thing that I was able to do really early in my life was get in rooms that some people would be like, "God damn, how are you around some of these people?" I sought that out. Like I did like I I was so motivated, inspired by by these people that were so successful that I was like, I'm going to get around these people no matter what. But, you know, how I showed up and how I allowed myself to be, you know, and maybe I'm harder on myself than I should be because when you're young, you not as mature. But like I look at some of those times and I'm like damn like I wish I had really taken advantage of some of the things that I had done. You know I have an interesting person early in my career that like I got close with. One of the first like like artists or talent was heavy D randomly and I remember he said to me we were out >> at the Whiskey Blue in the city and I was working on this internet company in 1999. I tried to convince him to like become a board of advisor and he was like, "Yo, do me a favor. I'm going to do it. Just chill." >> It was like, "Just chill, man. Like, he's so hype right now. Like, just stop. Like, let's just chill. You stop talking about it, man." And like, I wish I had taken that kind of advice more times than not. Cuz I'm How many times you've been out, right, where somebody's talking to you about business and they're in your ear and they're talking to you and you're like, "Damn, bro." Like I would like I can't what I can't talk about this [ __ ] right now. I was that guy. Like I talked about that [ __ ] all the time with everybody. So >> self awareness now. >> What's up? >> Is it self-awareness now? >> And I'm like damn man what how did I run up on these dudes like talking about this [ __ ] But you know you learn it. So I think if anything it's just like you know I I have learned how to show up better. >> That is my that's that's my question though. I am like even in rooms now, you know, I remember the party at the Fanatics, we were there, you know, and I knew KD at the time and I've spoken to him. I've seen him, you know, he was having a conversation. I was going around speaking to people and I looked at him talking and I was like, "Yeah, I probably shouldn't go say hello, right?" And when I did, he was fine and all that, but I get uncomfortable in those settings when I see people who have, you know, attained a certain level of success in their walks of life. What gave you that confidence? Or even more so, like how were you able to overcome whether it's being shy, being embarrassed when being in these certain rooms with people who were on levels you were working to get to? >> I'd always talked myself through things. I'd always been able to mediate whether it was fights amongst groups of my friends, whether it was problems with family members older or younger, I always was like that per everyone's resource. And I think that some of the things that I I dealt with earlier in my life, you know, you know, like I I don't I'm not even I don't want to say this in like I'm like like trying to have like a like a Oprah moment, but like no one's supposed to take their mom to the emergency room 15 times before like 11th grade because they would took too many pills or did too many drugs. You know what I'm saying? So, it was almost like, what's the big deal? >> What were some of the worst times? And how did that affect you being that young? >> It was all like, honestly, like I'm not even I'm not even like exaggerating like as I've gotten older and she just passed last summer, all of it. Yo, honestly, it was just so chaotic. I'm sure there were moments where like she was charismatic and I did I did really want her to be happy and and try to enjoy life, but she was just she was just a mess. like she was always a mess. So then >> she never got it fixed. >> Never. >> Wow. >> Never ever ever got her life together. It was just it, you know, it was funny. When she passed away, I wasn't necessarily there was like a wild feeling of like >> this is over like if if that makes sense. Like yeah like this is over like I don't have to deal I was dealing with it till the last day of her life. But the then it the sadness was like nobody doesn't want to get their life together. Like somewhere deep down inside nobody doesn't want to get their life together, you know, and she she was kind of like, you know, in some ways she was doomed. You know, she was doomed from the start. Her brother, as I told you, was sick and he was homeless and [ __ ] up. Her mom was not well. So, I felt bad for her. But it was just so much, bro. Drugs are so bad. Like, addiction is so [ __ ] up. And like that [ __ ] would tear at me cuz I'd be like, >> I see what I see. You can't tell me I'm crazy. Like don't tell me I'm crazy. But you know, just as I got a little older and she couldn't really hide it anymore. It was just seeing it. Like you just don't want to see. You don't like wake up at late afternoon and dry blood in her nose and like I just it [ __ ] was just awful. So you know for me like I always thought like what's the big deal? I'm going to go up and talk to [ __ ] Q-Tip. You know what I'm saying? Like I love Q-tip. Like that's not going to that's not I can't be thrown off from that. I can't be thrown off from that. >> And Channing asked this question of people many times. >> Was it hard with all the success, all the people, you know, the the amount of money you've been able to create for yourself and others that none of that could fix your mother? >> Yeah. It's funny. Yes. Because what happened was when I had kids, I really tried to integrate her back into my life. I was supporting her completely financially and and um I knew she was always going to be like at that point a little bit off, but like it was okay. Be the crazy grandma. Like, you know, no matter what, I was like, I got to have them have some connection. And she still wasn't happy and she was still mean and like just like erratic and and [ __ ] was just always [ __ ] up. But like honestly this you you can't even make this up. Like all I ever wanted was her to find someone like because think about it right if you just found somebody like here like please yours. >> No. >> Like please. >> And she started dating this man who um was like I guess sober himself or something. And um they were got engaged and there was this like little period of time where I was like you got to be kidding me. This man walking out of a a meeting, car hits him dead. >> It was like, you got to be [ __ ] kidding me. >> I was like, this [ __ ] I can't. So, like, >> well, that's a movie, >> bro. It was crazy. So, like I used to say to her like, "Yo, I told you I was going to make money." Like, I used to always say, "I told you. I told you I was." I said, "Told you not to worry about money. I will figure it out." Cuz when I supported her in the beginning, it was bookie money, gambling, DJ management. I just gave what I could help out. I'm like, I'm really doing it. Like, yo, it's over. Like, we don't have to like we don't have to do this [ __ ] no more. But she just couldn't figure that [ __ ] out. So, it's a shame that she couldn't figure her life out. It's [ __ ] up, >> bro. You're bringing up some names, bro. Heavy D Q-Tip. You then you try to put them two on a board with Robert Dairo. >> Yeah. Who in the hell was picking your board members, bro? >> I had a wild, wild network, man. I started this I started this internet company. When I dropped out of college, I moved down to Florida for like 6 months. Just living at like 20 years old in Bokeh, going down to Miami and just like chilling. I don't know what we were doing there. I was really thought I was Ace Rosteen during that six months. I really did. Then when I came back, two kids that I knew that graduated Cornell, um, both who I speak to today and both who went on to be incredibly successful, but like that was my life. Like I bridged all these worlds. So like I had these two kids that just graduated Cornell and they wanted to start this um, hiphop website in 1999 and like sounds pioneer in 1999, man. And it's funny because the company was like sports, business, entertainment. It's like basically what Boardroom is in some ways. But they said to me like, "Look, we want to get in the sports and music world. We don't know anybody." Like, you know, I'm the finance guy. I'm the tech guy. And we built this company. We raised a few million dollars at like 21 years old. I threw a crazy launch party in the Hamptons. Probably spent half what we raised. I had Mark Ronson and Q-Tip DJ the party. And you know, back then it was no social media. So like the way you would get press would be like announcing this board of advisors. It was like it was basically like these are our investors, but like it was before there was like strategic investors. So it was basically just like here's people we're putting on our board of adviserss. They're advising us and we're going to use their name. We're going to put it in the press. So I was able to get Q-Tip. I had met Heavy D. And then one of my best friends in the world was Robert Dairo's son. >> So we were able to get Robert Dairo and Steve Stout was a board of adviser too. >> Bro, that's crazy. It's funny. Think of you talk about spending half the half the investment on the party. >> How far do you push your flips? So the bookie money you had to move that to this, then you move that to this, then you move that to this. Do you have a percentage that you're set or I'm going to try this with that? >> The bookie money, the bookie [ __ ] got ended abruptly cuz I tried to run it in New York and it got tricky. >> It got a little trickier in New York. I wasn't welcome running my book here as much as it was in uh Boston in my college network. It was a little different. So that just became my way of living. So I was living off of it and then I was then like >> then I was gambling with my bookie money and I was living. Listen, >> I don't suggest this for most people, but at that point in my life, this is how I looked at everything. I said, "This is what I'm that you're talking about betting on yourself." That's when I realized it. I was like, "You know what? Whatever I got, I'm I'm putting it into like I'm putting into me." >> You know, if someone said everyone's going to be in Vegas, I was going to Vegas. Someone said, "Yo, they're doing this comp retreat, music retreat in Bahamas." I'm going to Bahamas. And I didn't get business from it all the time, but I kept building and building and building and building my network across the industry. Then the first like real job job was when I started working on that show, the life. I remember I got a paycheck from that show. I was just like, I don't know what the [ __ ] to do. I went to the check cashing place. >> You didn't have a bank account. >> I did. I pro I had a checking account, but like that's that like I just wanted the money. I just wanted the cash. You know what I'm saying? >> And the fees were crazy, but it didn't matter. >> Yeah. >> Yeah. >> Talk about building. You've worked with athletes, uh, artists, billionaires. What separates those people who build wealth versus those who just earn? >> That's a good question. I think that like if your motivation is to just make money, um, and all you're thinking about is making money, especially like for entrepreneurial people and and for talent and creators, then you're going to earn. If your goal is to build enterprise and and and is built with a vision in your mind and the vision can keep evolving, but if there's a if there's a story that you want to tell, if there's something that you want to impact, if there's a purpose you have around all of it, then I think you have the opportunity to build wealth. Because if you're trying to do nothing but transact, which is why I couldn't be a talent manager anymore. I wasn't going to be a good town manager because I would remember I would go try to sign people in music and in sports and if we didn't get them I was like I still want to [ __ ] with this guy. Like I don't but that's not how it was wired. Like it was like nah [ __ ] it. He not coming with us. And I was like but I there's so much [ __ ] we could do. That's why when people say to me you know you only work with Kevin right? I'm like no. I'm like I only represent Kevin. I work with everybody though. Like that's the point. Like I wanted to be in this position where I could be agnostic, where agents can call me, athletes can call me, owners of companies can call me and I can have a brand and a platform and something that can add value or amplify or storytell. And you know, it took a while because in order for that to mean something, I have to mean something >> and the brand has to mean something. >> But this is what I this is what I'm most comfortable doing because like I don't want that. I don't want that. Like I remember when I was a basketball agent before I like quickly just started working with Kevin. I was like why do these guys not talk to each other? This is the craziest thing. I went to an agent meeting and everyone was like in different corners and I had known Rich Paul for like 20 years already. So I said Rich is what like this is what they do like they don't talk like no it's like how the environment was and that didn't really make sense to me. The music business wasn't like that. Like if Jay-Z signed someone that Jimmy Ivy was going to get two of them were still breaking bread together. I think it's changed now. I don't feel that same energy, but also I sit in a different, you know, position now. >> You and Kevin and all of your ventures. >> What is at the foundation and what is at the principles of what you are trying to build not only within YouTube but as you continue to make branches of that tree. >> I think we enjoy working together. Um, so it makes work fun. You know, I know it sounds like simple, but like who doesn't want work to be fun? Yeah. Right. So, >> I think we really enjoy it and um we enjoy talking about it. And I think that like, you know, we've evolved individually so much over the last like 13 14 years that there's been different iterations of what that looked like, you know, and there was times where we focused more on certain aspects of what we wanted to do. And now I think there's this like bigger holistic view that we both have on everything we're doing. You know, I think that people seem like will say things to me like, you know, how involved does Kevin get? And I'm like super involved. Like I would never be I wouldn't run around and say this is my business partner and and do the things we do if if if Kevin didn't want to do it, right? If Kevin wasn't totally aligned, he's challenged things that I've wanted to do. He he challenged me in building boardroom. I almost was like, I don't want you to do everything for this platform because I don't want this to be Kevin Durant's media platform. I'm going be keep it 100 with you. No disrespect. If we're going to build something special, this thing has to operate completely separate. And then when you want to be on, it's like gasoline, right? You come on and you do what you do and you find your space in it. and as it's grown and we've talked like seeing his belief and his ideas that we've like decided to implement has been special. And then on the 35 ventures side, you know, that's been an evolution cuz when we were in Silicon Valley, it was about investing in venture and we had access to such incredible companies and there was such like great world changing leaders out there. Like really no [ __ ] like people were really changing the world and we had access to it and and it was exciting. And then as you know, we moved out of there and started thinking more about like you said, like building wealth, like now we're doing real estate development all throughout Maryland where Kevin grew up, like all through PG County. Like that's purpose, right? That's legacy. And for me, >> you know, I didn't grow up there, but I I find the same reward and joy because that's like really my brother. And you know, and building that legacy for him is important. And the thing that I think has been special about our relationship is that I am his manager, right? Like, so I don't phone that job in. That job is not too big or small for me. Like if Kevin wants me to cash app him some money and I'm out, I'm cash apping him money. I don't need to call an assistant or like I whatever he needs. And that like respect after 14 years of me going, "Bro, you gave me an incredible opportunity because I was hustling. Listen, I was going to work it out regardless. Like, I was going to figure it out and I was going to make money. But I had never had anybody that [ __ ] good at anything that like important in this world ever. Family, friend, coworker, nobody that believed in me the way he believed in me that just said, "Nah, I want him. I want him, bro. I'm going give him I'm going to give him the win at his sale to go do him." You know what I'm saying? And he always did. I remember one of the first times I went to an OKC game as his agent. I wore some nasty ass suit cuz I was like, "Everybody's wearing suits." And I just like quickly got a suit. He was like after the game, he was like, "Bro, you that ain't you. Stop wearing [ __ ] suits to the game." >> I was like, "This this is my guy. Like he gets me." You know what I'm saying? And I think that like when someone gives you that belief, when you don't have somebody that gave you guidance or you don't have like a real direction and listen, I was honored to be around Mark Ronson. And it was an honor, my god, to be around Jay-Z, even to know him. Like that was incredible. I learned so much. But nobody in my life had ever been like, "Bro, you the guy. I want you to be the guy. I want you to build my business with me, and we're going to get through all this [ __ ] together." And his whole family did, man. And his mom his mom has given me in my life like tfold what my mom never could give me. And that's his mother, man. You know what I'm saying? >> You said you said it a lot. You're going to figure it out. I'mma figure it out. I'mma figure it out. Mom, I'm figure out you. I'm going to do it all. And your empire is you. Your relationship. You like your cell phone. You can call anybody. >> You said the word legacy. What is the legacy in a hundred years for you? Because if you're not around, a lot of this stuff's not going to work anymore. >> Yeah. I I won't be around in 100 years. >> None of us. But but what what are you what are they talking about with you? >> I think that like it's kind of like a mind [ __ ] when you get older a little bit. You realize that like what does that mean in that I probably won't be remembered in a 100 years for anything like unique in terms of what I brought into the world. And that's a [ __ ] up thing to think about. Right. And I >> Right. It's just like it's a it's somewhat of a sad reality, but it's also fine because, you know, that's life. That's reserved for Michael Jordan's and Steve Jobs and Kevin Durant, right? And Jay-Z. It'd be cool if I built a business. And the reason why I didn't want to really like go after it and raise money or try to quickly develop Boardroom was cuz like, you know, maybe this is a bit of a pipe dream, but I I would I would love it if it was seen as like what Forbes is now, right? Forbes is hundred years old. So that would be cool if like someone was like, "Oh, you know who built that?" But really, I guess if I can take that like community that I built around me, which is big, and and have maybe generations of those people, you know what I'm saying? The way like cuz I don't have a big family. I just don't have a big family. You know, like my father had a a sister who never had kids. Sadly, she died of addiction. My mom's brother, I met him one time. He had kids. I've never met them. I have no idea. Grandparents not here. My mom passed away. I'm super close with my dad now. My dad is a straight G. Dresses every day. Same way. Suit ass. He's incredible, you know, and I and I'm super close with my brother. And I've been married for 20 years. I've had the most incredible wife that has taken this journey with me through this whole [ __ ] Like, it's that was a blessing. And to be honest, I don't even want to downplay it. I didn't get through any of any of that if I hadn't met somebody young because I was broken, >> but she saw it. Right. So when I say nobody believed in me like Kevin, I say two people really. >> Yeah. >> Because she stuck it out with me the whole way through. There were times she's like, "You really going back on the road and you still giving me [ __ ] about this credit card? Like what are we doing? Like what are we building?" >> Wow. >> Trust me. Like trust me. So, you know, I think like if I can have a community of people, you know, that that have talked about me, if I can honor what Kevin did postc career and continue to build, I always say to Kevin, I want you to be the Rockefeller of uh Prince George's County, Maryland. You know what I'm saying? And I want generations to be like, he built this, he built this, he built this, he gave back that, he gave back that, >> you know, and I'll, you know, I'll figure out like maybe they'll uh make a movie like Casino loosely based on me. >> You're working uh you're curating something for the National Museum of History. >> Yeah. >> Coming up here in the spring. How did all that come about? And what does it mean to you that you've been called on to do something like that? >> So cool. So cool. because I didn't see that coming like right like 20 years ago. But, you know, I think that that to me felt like a a nice validation of like how I'm trying to position myself because like the word curating um you know was like an important word for me and it's an important word for my business and and how I think about the rooms that we put together. You know, I think curation and being able to understand exactly how all bunch of pieces can work well together has always been like a bit of the ethos of what we're trying to build. So, you know, I think to be able to do that felt like an acknowledgement of maybe like, okay, yeah, he would have like a level of understanding to help it, you know, and the woman Vicki who brought me on to do it, you know, she she had that quality too, like which which is why it made sense when I met her, like she had that as well. So, you know, and I grew up in the city and you know, it's a cool thing. And also like I I am really big on like especially in today's day where like digital media is so broken and fragmented and nobody can remember [ __ ] and nothing means anything that like you have to be constantly like weaving this web of things and moments always throughout and it all paints a picture and I'm like this is painting a beautiful picture of everything else that I'm trying to do. like I'm going to curate this exhibit around sports at the Museum of Natural History. That makes sense from the guy who also is building this media business who's sitting at the intersection of sports and entertainment and business and who represents one of the best athletes. Like I see all these parts and I'm like starting to paint this picture and tell this story. And then it was just like an honor, you know, to to be a part of it. Man, who who would have ever thought Tom Kilman would have been able to >> Tom Damn Kilman >> do all of this? >> Kilman, >> you know. Uh, with that though, uh, we ask all of our guests, Rich, uh, their biggest pivot in life. That's that one moment you can look back on and say because this happened to me or for me, I am who I am today. >> Yeah. I guess the big biggest pivot for me was probably um when I moved back from Florida as a kid. You know, I was, like I said, I was booking and gambling and just running around and, you know, I was like, "Oh, I'm gonna open a club. I'm gonna open a restaurant." Which really was like code word for I'm not going to do [ __ ] Uh, as soon as I got like a tiny bit of taste of like the real world with that show, the life when my friend asked me to help out and um and I got a little bit of a chance to see like, oh, this the way the world works, I realized like now I'm going to I'm I'm jumping on this train now and I'm making this like I'm going to make this pivot into like really trying to do something for myself. And um it's a long road. So, like the pivot was not the sharpest cut. You know what I'm saying? But that's when I realized like I could have really easily just like kept [ __ ] around. And I know a lot of kids from the city that just kept [ __ ] around and they're still [ __ ] around, you know. >> No, man. I appreciate you, bro. Just growing a relationship with you, getting to know you. You are true. You are authentic. And I think if you continue to work and people get to see that show up each and every day, you do get the opportunities that you've gotten. And then it's about taking advantage of them. You know, which you have done on many occasions, which you are doing now. And I think for our show, those are some of the conversations and some of the journeys we need to highlight as well. It's always like this athlete who was drafted in the first round, made a lot of money, was as good as people thought he was, so he made more money. Conversations about people who failed, who weren't always thought of as the greatest or the best, and found their ways. That's more real life than anything, bro. So, we appreciate you. >> I appreciate you, man. >> My dog. Yes, sir. >> Dude, that was good. >> That was awesome, bro. >> No, when I read that when I read that Tom Kilman joke, I was weak, dog. But bro, I was weak, dog. >> I can't believe it. >> But that's also like such a white man's basketball story, bro. >> You know, you know what I'm saying, dog? >> I was sick and they didn't hold up it. I f to witness it. Got my people feeling way up on a mission. Got me up. I got the key on this vision. Trust trust limit pinning it. I found the here to witness it. Got my people feeling militant way up.