Aspire with Emma Grede - What Growing Up in Chaos Actually Teaches You (Rich Kleiman)

Episode Date: March 17, 2026

Emma has known Rich Kleiman for 20 years. In all that time, they've never talked about where he actually came from, until now. What came next was one of the most honest conversations we've had on the podcast.  The hardest story to change is the one you tell yourself. For Rich, it wasn't a lesson,  it was survival. He grew up navigating a volatile home on the Upper West Side. With a mother battling addiction and no one to watch him, Rich was left to figure life out on his own.  Today he manages Kevin Durant's business empire, has built Boardroom from scratch, and is one of the most respected operators at the intersection of sports, music, and culture.  In this conversation, he and Emma get into how chaos became his competitive advantage, what it really takes to build a partnership that lasts, and why legacy means more to him now than money ever did. Rich shares:  How growing up around instability shaped his instincts in business. How his ability to navigate chaos made him a better leader. Why notoriety and success aren't the same thing  Why the stories you tell yourself matter – and how truth outways comfort.  Why making peace with your past changes how you move through the world.  What's the story you keep telling yourself? Drop it in the comments — we'd love to hear from you. And don't forget to subscribe so you never miss an episode of Aspire with Emma Grede. To learn more about listener data and our privacy practices visit: https://www.audacyinc.com/privacy-policy Learn more about your ad choices. Visit https://podcastchoices.com/adchoices

I am so excited to share my debut book with you or Start With Yourself, which is available now. You might have seen the headlines, you might have seen the social, but this book is exactly what I intended, a conversation that will make you think, and it's a blueprint for anyone who wants success without the toxic positivity. Start with yourself is about self-leadership, because wherever I go, women ask me how I got to where I am. But what you really want to know is how you can get there. So I'm doing what I do best, sharing and navigate keeping what's works for me in the hope that you can borrow from a philosophy that has served me so well. The truth is I'm not an expert. I've just lived it. I've made the mistakes.

I've had the failures and I've learned what actually works. It takes a lot. It takes the most. And this book is for anyone who's tired of feeling like a passenger in their own life. It's about taking responsibility for your thinking, managing your emotions and getting clear on your ideas and then knowing your next step. It's about picking yourself up after failure, being accountable, but also forgiving yourself, pushing for wins and never, ever apologising for your ambition. It's also about challenging the rules that you've been told. There is no perfect time. Balance isn't the goal. Alignment is and there's nothing wrong with you wanting more. I'm precisely sure that the reason I've been so successful is so I can share it

with you. Start with yourself. My debut book is available now. Visit emigre.com to purchase the book, also available on Amazon, your favorite audio platforms and all good bookshops. So today I am so excited for you to meet one of my old friends and colleagues. I've known Rich Climmon for over 20 years, and I cannot tell you how excited I am to share this deeply moving conversation. Completely not what I thought we were going to do today. But the reason I want to share this with you is because I think whenever we think about trauma, especially that that come from our childhood, it's always with a negative connotation.

And what is so incredible about this conversation is how Rich has completely dispelled those myths and brought it into his life in a way that has actually helped make and shape his success. And don't forget, before we get into this, to like and subscribe. This episode is sponsored by Macy's. Now, one of the easiest ways to refresh your wardrobe is by starting with a great pair of jeans, because when the denim fits well, the rest of the outfit will always come together completely effortlessly. And that's why Good American is a great option when you're thinking about a seasonal upgrade. From day one, we focused on creating jeans that actually cater to women's bodies,

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Shop now at Macy's.com or in store. The start with yourself tour kicks off on April 15th in New York City. Tickets are on sale now at emigree.com. Rich Climann, welcome to aspire. Oh my God. I am so honored to be here. I am. I cannot tell you how happy I am.

that you're here. I think the first thing that I have to do is level of anyone that might be watching this because I've known you for 20 years. 20 years, which is extraordinary. I've known sport rich. I've known music rich. I have known the new media mobile rich. I love this. We've actually never spoken about young rich, which is where I really want to go today because we all need to understand what has made you, the person that you are today. But ahead of that, for anybody that is watching this episode that needs to know more about you and to contextualize you in the way that you are on what you're doing today. Can you just give the audience just like a little flavor so that we understand exactly where you are now? Where I am right now. Yeah. Well, right now I am very

lucky to be sitting across from you. That's where I am right now. But I am the founder of both boardroom, a media brand that we've built from scratch that is just my pride and joy and 35 ventures, which is the family office of sorts, the hold co for Kevin Duran and I, and I've been managing Kevin for almost 13 years. So I still operate as his agent, but that all sits within our family office. And that has our investments in real estate and sports

and private equity and venture, his Nike business, which is 19 years and running now, and our foundation, which is like a big part and rooted in kind of all the work we do on that side. But Bordroom is where I flex my entrepreneurial gene. And boardroom for anyone who is just asleep.

Just let's talk about that business for a little while because it has amazed me, but it's so true to you. Because as the person that was music rich and sport rich, like, I mean, you've really kind of put these things together. But explain it for anybody that isn't following right now. Really should be. Yeah. I mean, you know, growing up in New York, I think I had the benefit of being around this like explosion in culture around both hip hop, basketball culture, downtown New York culture, club culture. All of it was happening in my like formative years.

And I liked all of it. I liked all of it. And I always wanted to be in the room. The oxygen that I got was from being around people, always, all different types of people. And I always realized that I couldn't put my finger on exactly what it was that I loved. I just wanted to be regarded in those rooms. I wanted to build something. When I was seven years old, I launched.

this business called Lawyer Kid. The idea was that all my friends would bitch about their parents. So I was like, let me rep you. Like, let me deal with it. But really, it was just so I could like make a business card and walk around and say I own something. And I did that all the time as a kid. And as I started to get into my work world, I ended up in the music business even though I obsessed over sports. And within the music business, I would wear different hats. I was a music supervisor. or I managed DJs, I consulted for clubs. I hustled. That's all I did with no real structure.

I hustled. And when I finally got to the place that I wanted to be around the sports world, I realized that if young me had ever had the opportunity to consume a brand that, like, lived at that intersection, that talked to people that were interested in all those things. And I was fortunate that as we started to build it, that world became the center of influence. And there's certain rooms where you can. be in private equity, sports, art, music. And if you're in that room, it all makes sense to everyone else. And that's what the brand really embodies. I mean, you've done such an incredible job of it.

I mean, it has to be said, so I met you in the, I guess, I don't even know if it was music or sport days because you were a music guy to me in running a sports division in a music company. Right. I met you when you were at Rock Nation. Yeah. No, no, it's actually before that. Did I mean you before that? Yeah, because, you know, the first, like, real, person to believe in me or see me in a way that felt powerful was Mark Ronson. Oh, wow. Yeah, of course. No, I met you through Mark Ronson.

Yeah. So you were doing a shoot for Mark. I was trying to do a lot of things back then. It was a Mark Seliger photograph. Oh, wow. And it was Mark for GQ or for Gucci, something. Yeah. And you walked on set, and I was like, oh, I need to know her.

Oh, and I was the same. I was like, this guy, like, he's going. got it down, everybody knows him. And I literally forget Mark Ronson, as lovely as he is, but I was like, I'm going to be friends with Rich, like this guy. And you were so nice and so kind to me. And you said to me, what do you need? What are you want?

And I was like, everything. I need to know who you are. I need to like be in these rooms. I need to do this. And the one thing I will say about you, Rich, that still prevails to this day, you were so unbelievably kind. And I think so many, you know, managers, agents, publicists, they say. say shit to you while you're on set, and then they never pick up the phone again unless you've

got something else to bring them. And what was so interesting is that you did pick up the phone over and over again. And you actually gave me like a huge leg up because you were like, do you know what, you're really good at this stuff? Why don't you work for my boy? Mark, and I was just like, who me? Really? You were like, yeah, absolutely. Like, why don't you do what you do? And I was like delivering commercial opportunities. But at that point in my career, it meant an enormous amount to be seen by someone that was in your position because you were flying high with this artist that was flying high and I was like the run of the like the broker like nobody cares about the broker

it's like you've even got something to bring and if you don't somebody else will and it says a lot about the type of person you are and how you do business and how you move and the fact that we're still friends all of these years later that's right well I appreciate you saying that no it's the truth so let's start at the beginning I want to understand a little bit more about the environment that you grew up in because the way that I always saw you is that you were with the coolest people. You're over here with Jay-Z and you're over there with Mark Ronson. You're over there with Katie.

But this is not at all your start and your upbringing. So tell me like, where were you born? How did it all start? Like, give me the background. Yeah. I grew up in New York City on the Upper West Side at a time where there was like a real middle class in New York where you could go to private school, but you maybe didn't go away on vacation, right? Really slum in it.

Priorities. And I was always surrounded by people. Everyone was always at my house. I always had like a big group of friends. But my house was volatile. Like it was really volatile as a kid. And I thought it was normal. But there was so much fighting and screaming and yelling.

And, you know, my brother and I hated it. It was so bad the way they fought. And the thing was is that my mom was the vicious one. You know, my mom was the really, really vicious one and also erratic and emotional. But I loved her and I was close to her because I almost was worried for her and scared for her. But when she was okay, she was so electric, you know, and she was charismatic, but it was very, very rare. And I remember when my brother and I, for like 10, they sat us down and told us they were getting divorced. person, I flipped out. And then like two minutes later, they each lit a cigarette. I'm like,

and you smoke? Like, what the fuck? This is the worst day of my life. But then over those next four years, it was a really odd thing because they didn't actually separate. No one left the house. Oh, so they remained together. But they weren't together. They hardly spoke to each other. And I used to wait up at night at the like doorstep of my room just to make sure they were sleeping before I went to sleep because I didn't want them to fight. And I lived in just complete fear of them just unraveling. And then when my father finally left, you know, I stayed with my mom because back then that's what you did. You know, so you stay with your mom. You see your father on a weekend or something. And my mom really just like fell apart from that point on.

She was addicted to drugs. She was completely just off. And she was mean. She was just mean. And it was around that time where, like, you're 13, 14, the stakes at school become higher. And you have to lock in. And no one was watching me. No one was paying any attention to what I was doing.

You were a receipt very emotionally insecure. Were you financially insecure, too? We were good. My mom complained about money all the time, yelled about like my father was not giving her, but we were fine. But emotionally, it was just chaotic. You know, and I would live two lives because when I was home, it was chaotic. But when I went out the house, I was able to park that and be at the center of the party. And I really wanted people around me. So it was around you. Whatever was going down with your mom was visible. This wasn't something that. was happening behind closed doors so much? No, I would walk in her room and, you know, she'd be out for 36 hours on the bed. She's doing drugs in our house. And the thing was, is like, I just wanted to get out.

So the only people hanging out during the school week were not the kids that I was going to school with. So I just went out and went to the corner. I mean, I had a crew of like 40 of us that hung out outside of Burger King on Broadway. And we just chilled and it allowed me the ability at times to be around people that also has shit going on in their life, where we really could relate to each other. So when I ended up going to college at 18, I got into one school, applied to like eight schools. I knew I wouldn't get in.

I applied blindly because I damn near got Cs and Ds. Like I really, when I tell you, I did not go to school. I went to school every day because I love being around people. But the education wasn't the focus. I didn't even think about it. Me either. I phoned in every single thing I did. I hustled my way through high school.

But there wasn't like a learning difficulty. This was really just about you having, there was nowhere for you to focus. There was no one at home telling you like, do your best. It was like everyone was for themselves. Your mom is kind of tapped out and you're going to school every day, dialing it in and really focused on what happens after school. Yeah, no learning problems. If anything, I got stuff quick enough to just get by.

Right. I mean, that's crazy. I wonder for you, like, what insecurities from your childhood have actually stayed with you. And I want to kind of get into your college years because I feel like they were so formative in your life. But there's stuff that just happens when you're really young, like between the age of seven and 14 that is so formative. How does that show up in your life now? I think, like, my ability still to this day to navigate through chaos, no matter what's going on, like my heart doesn't ever race like that. That heart doesn't skip a beat.

My brain doesn't start spinning from chaos anymore. If anything, I know I'm the right person to navigate through chaos, whether that's in business or for a friend of mine or family. I'm hyper aware. If you're an anxious kid, which I was because of everything being so chaotic, I'm always aware and paying attention and nothing's going to get by me. And I can read rooms really well and I can read people really well. But I think most of all was, you know, I felt for my mom.

And it took me a long time to realize that because I really did not like her because of how she treated us. But I felt for her because when I got older and I started to think about like, you didn't want this. Like nobody is born wanting this. So there's a level of empathy that I live with still to this day that allows me to manage situations because if you don't, you'll go crazy. Like if you really think everyone's out to get you. or if every negotiation and business and everything you do in life has got to be a battle, that ain't for me.

I don't have the, I don't even have the energy physically or mentally to do that. So I like to think about what the person on the other side of the table is going through or thinking about. This is kind of amazing to me because I think for people that are sitting home listening to this, you know, you always imagine that your childhood trauma will only have like negative effects on you.

And everything that you described is actually a superpower. Things that you learned, coping mechanisms that you learned as a kid that actually allow you to be the best at what you do now, right? It allows you to be able to be in a crazy, chaotic situation with very high stakes and yet remain calm. It allows you to be the good friend. It allows you to see what's happening in a room and in a situation. And the other side of this coin where despite what you went through with your mom, you being empathetic and then finding that in situations and being able to say, in this negotiation, and what's happening on the other side of the table.

These things are superpowers. Like they really are. And I think it's so important to remember that regardless of where we've come from, what we went through, you can do two things with all of this stuff, right? It can really kill you, but it can also be the making of you. And I look at you and I look at your success and go, these things, while horrendous and unfortunate and not making for the best childhood, they've made you who you are.

And they've given you the ability to be the person and run. run the businesses that you do now. It's pretty extraordinary, really. I appreciate it. I mean, I think, you know, I did the work. I did. You know, I really did do the work. Say more about that. Well, listen, when I left my house when I was like 18, again, I went, I got into one school and it was just like general studies program at Boston. And I went up to Boston. I wasn't ready to go, but I knew I was ready to get out of my house. Uh-huh. You got to escape. And, you know, as soon as I got there, like true to form, I was out and I partied and I had a big group of friends and I was whiling out a little bit. And I ended up finding what my hustle was. Like, I always need something to be

hustling with. And hustling has a bad connotation in some cases. But for me, it doesn't because in my opinion, it is like defined as like when you don't really know yet what you want to do. But that thing is going on in your brain. You just got to keep it moving. So I ended up becoming a bookie. You did? I was a bookie in college. And it was eye-opening for me because it was like it was intoxicating, man. I loved it. I loved making the money. I loved dealing with people. Do you remember how much money you were making then? When I left, so I ended up living in Boston for a year and a half after I got kicked out because I kicked out after the first semester. And I lived off this money too, but I probably left with like,

close to $275,000 cash. Oh, you were, you were really out in the streets. You were doing things. I was crushing it. Hundreds of thousands of dollars. What did you get kicked out for? I just didn't go to school. I literally didn't go to school.

Like as soon as I was busy, the first morning I woke up for class, I looked at myself. I was like, nobody's going to say shit. Like, I need to sleep. I was so emotionally drained from life. Like literally at 18, drained. And I had time. I'm, and prioritized being out and being in the mix. Well, also, you were probably in a bit of fight or flight.

And I think when you've lived in a household like that, you don't know what to do when there isn't any drama. And so it does crazy things to your body. I remember leaving my own home and kind of feeling like, no, I don't want to say bored, but I was like, I kind of looked for drama. And I made shitty things happen and bad choices and strange boyfriends because I was used to there being constant drama.

And that's what I lived in and that's what I thrived off of. And that's all I knew. And so when you don't have that, there becomes this idea that, like, you replace it with something else, like either equally bad or equally damaging. Without question. Without question, to be honest,

that's exactly what I ran into, was there was this year and a half of, like, living in La La Land in Boston, like being a bookie, going out at night, and not focused on school whatsoever. But in reality, like, I had zero responsibility and I wasn't home. I mean, I would still call home and hear the way she sounded

or she wouldn't answer the phone for two days or I knew something was up. I always knew when she was high. I always knew when she was on drugs. But it all of a sudden hit me physically and I had the most insane anxiety attack that led me to the hospital. And it's interesting because at that time,

you weren't going to hear anyone say that out loud. You definitely weren't going to hear a man say that shit. No, what is this? 30 years ago. I mean, it's a long time. 96, 95. No one was using that language. I'll tell you the one thing that I never had a problem with is being dead up about what I was going through.

Where do you think that came from? I don't, you know, the thing was like, I know who I am and I'm confident, but I'm also like somebody that is okay with having fun at my own expense. And, you know, it felt to me like at that time, like if I hid that, that I was going to die. honestly, straight up. And I was like, this is not, this whole thing that's going on in my body right now and in my mind, like if I keep this to me, it's not going to work for me.

So I just kept it 100 with everybody around me with a smile and I laughed about it. And when I was like having anxiety attack or something or freaking out, sometimes it got the best of me and I ended up going to the hospital so many times when I was in Boston because I was out of control.

I didn't even know how to manage what was happening to me. But I talked about it. I laughed about it with everybody. And I ended up finding a doctor for myself in Boston. This dude was just prescribing me pills and shit. Oh, disaster. And then I remember at the end of my sophomore year, I was bookying. I was dating this girl.

I was out every night. I was having anxiety tax like it was like a cold. Wasn't even thinking about it. How did they manifest for you? Was it look like? My heart would race. My left arm would go numb. Just weird shit physically.

Do you still suffer from anxiety now? Yes and no, like they don't happen in the form of an anxiety attack anymore, no. Really, I've been able to harness it over the last few decades. If anything, I think I'm more of like a guide for other people that are finally dealing with that in their life now. Or if my daughter is feeling something, I remember my daughter said to me, I feel like I can't breathe. And I was like, I know exactly how you feel.

Like, and I talked her through it and understood that feeling because that shit is a weird thing to say out loud, right? And when you start figuring your body out, you start going like, how the fuck is all this happening? And right? And if you feel disconnected from your body, that's when you're going to really start to bug yourself out. And when I was growing up, my body was so scared of what was going on in my life. So my mind had to almost separate itself. So it was like two different things. So my mind had to take care of my body. So when things had come or I had time to think about something, your mind can kind of bug you out. And I remember I was sitting in my apartment.

And I called my brother and I'm like, I got to get the hell out of Boston. Like, this is crazy. Like, this isn't healthy. And I just took my safe with my cash and I went back to New York. Before you leave Boston altogether, I'm interested in that time when you were a bookie. Like, what did it teach you about navigating people and money? Like, what are the things you learned in that moment that perhaps like creep up now? It was like the basic skill set of running a business, like managing a P&L, right?

even though it was in a composition notebook and I was writing that shit in pencil, it was like managing a P&L. It was understanding the people that were betting with me and profiling them and going, you know what, this guy wants to put $5,000 in on a game, he don't have that money. I could tell he doesn't have that money. Your limit is this. It was knowing how much was bet on one side and figuring out if I had to lay off my best. So like if everyone was betting one side, I would bet with another bookie on the other side,

so I didn't lose too much. And then collecting, you know what I'm saying, and dealing with people, and then getting people to help me collect. And just feeling like some ownership of it and some pride in it. It was like the first thing I felt real pride in that I had built for myself in that way.

And also like there was a little bit of like that young, just delusional, like maybe I'm Ace Rothstein from casino. You know, like maybe I really am, this gangster. And it was like, I love that movie and love that character. So I was also like playing a role while I was being a bookie too. But not something for someone who's like really suffering of anxiety. So you decide you're like, I've got to get out of Boston and you leave and go to New York. Yeah.

Okay. What happens there? Because I just need to understand this transition from, you know, guy that leaves home is at college, is a bookie. And then you find yourself in the music business because I feel like one of the first projects and listen, I could have it completely wrong. But one of the things that I knew about you is that you'd done this Jay Z. documentary. So I need to understand this leap that like happens that you even get the opportunity to do that because you've got to be in the music business. Yeah. So I went back to New York and the only people that were around really were all my friends that really didn't go to college. So I started

hanging out with everybody again and we were going out in clubs. And at that point in my life, I really was like thinking I wanted to be in the restaurant business. I ended up moving to South Florida like randomly for five months just to get away with a friend of mine. We didn't do shit in South Florida, like truly didn't do anything. But by the time I left there, I thought to myself, okay, I got to do something. Like, I missed the booking side of my life a little bit. You missed the money? I missed the money. Or just like feeling like in control of something. I thought you had something going on. Yeah. And what happened was by the time I moved back to New York, a lot of kids I knew from the other side of my life were graduating college. And one of my friends, who's also today, a very successful

founders, guy Noah Kerner, founded acorns and built a few other businesses, really successful founder. He called me and said that him and another friend wanted to start a hip hop website. This is in 1999. And it was very pioneer then. The idea was just like community commerce content, really what boardroom is. Wow. And they said, we need somebody that's in the mix. We need somebody that knows artists and knows athletes.

And I did a little bit. I was out in the clubs. but I understood the world that they needed to tap into. So we raised some money. I threw a monster launch party in the Hamptons with Q-Tip and Mark Ronson DJing. And we ran out of the money like a year and a half, two years in. But at that point... You lost all your P&L discipline.

P&L discipline was gone. Out of the window. But that point I said, oh, I know what I'm going to do in this life. Like, I get it. I know what excites me. And I know how I can be successful and powerful. I got to start this journey. And that was that the music business.

Like I'm going to be in that business. Yeah, I mean, it was just like being around talent and like creating a brand for what this website was. It was called OneLevel.com. And it was just creating a brand and connecting the dots and bringing talent into our office and going out and networking and trying to raise money. And back then it was really big to have like a board of advisors. So like our board of advisors were Steve Stout, Q-Tip, Heavy D, and Robert DeNiro. And that was just being hustling in New York. And I'm 19-20.

Yeah. That's crazy. Did you understand at that point, like I have a skill for putting things together or were you just like, I just love doing this? I knew I had a skill for speaking to people from all different walks of life. Okay. And being in a room and being comfortable talking to anybody. And I knew I had a taste and I knew I understood how to get people to talk about something.

Like how to get people to react to something. I understood that. And as soon as that finish and life has like been. this constant journey of weaving these moments in my life. And I think that the reason those moments kept happening to me is because I just kept moving forward. And I kept putting myself in the right place. And a mutual friend of ours, Jamie Patrickov called me. And he said, you want me to come to radical media with him, a production company in New York, to kind of pitch or be a part of the pitch on this show, the life, which was on ESPN. And it was a sports show. So I think Jamie knew like,

here's somebody that has institutional knowledge and understanding of sports. Because I was that kid. I was like an encyclopedia. So we ended up selling the show to ESPN. There was no role for me as a producer, but they needed a music supervisor and I knew nothing about it. But I raised my hand to do it. And the thing that got me was that there was a budget and whatever I didn't spend I could keep. Oh yeah, that'll get you. Today we helped a latte for Sam coffee shop get an insurance quote simply and easily and made sure a floral delivery van was able to make someone's day. We're the Hartford, with decades of experience ensuring millions of unique small businesses. When it comes to your small business insurance,

thank you. One size, absolutely does not fit all. Get a quote or find an agent today at thehartford.com slash small business. The start with yourself tour kicks off on April 15th in New York City. Tickets are on sale now at emigre.com. Do you think that perhaps not having much guidance in your life made you fearless? because that's a pretty like crazy role to step into with a friend without you knowing anything or what to do. No, no blueprint, no game plan, no rule book, no guardrails. Were you scared? No.

No. There was no fear of like I could fuck this up. No. The way I looked at it was like I was scared my whole, I always was scared as a kid. I was so scared to hang out the window waiting for my mom when she wasn't home. I was scared about that shit. all the time. So for me, I was just like, this is fun.

Like straight up, this is fun. That's crazy. Did you have a mentor or someone around you at that time that was helping to guide you? No. I wonder if you think that the absence of a mentor actually gave you more of a runway to trust your own instincts. If you just, you didn't have a choice. So you just were like, okay, what do I feel? And you went for it?

You ever see Goodwill Hunting when Robin Williams says to Matt Damon, like, who challenges you? And he was like, what you mean? He was like Shakespeare, this person, that person. It wasn't like that for me, but my mentors were who I watched. Like, I observed them. They didn't give me any game. No one put their arm around me, but I observed them. And I watched them, and I was aware.

I was always aware. And I was curious. And the curiosity didn't always manifest in, like, me getting time with someone to ask questions. It was just like seeking it myself and seeking information and watching people. and pushing myself to go into rooms where one would be uncomfortable. And, you know, I think that was exciting. And when I took that roll on, I learned a new skill, which was that I knew nothing about the music business.

But I had two or three people that I knew had started in the music business. And because my relationships where people were strong always, I went and sought out, like, the basics. And when I sought out the basics from them, I knew enough to start to figure it out on the job. and I started building out this database of unsigned artists and producers. And the music really became like recognized as like a big part of what this show was. And I then found myself in the music business. And the reason I did fade to black was because through all that,

I ended up in a room where I met Jay's manager at the time. We went through radical media. And Jay had had this incredible footage from Madison Square Garden. And next thing I knew, like I found myself a producer on a film of one of the, of the most iconic individuals of our lifetime. I mean, it's so crazy to me because throughout your career, you've kind of had these kind of relationships that have become currency for you. And I wonder at what point you really realized that your proximity had so much power

and can get you in the rooms and you could then leverage that, because it feels like you've done that over and over and over again. Listen, I think growing up in New York is like a real blessing in that regard. No doubt. And I think that the diversity of the group of people around me, my whole life and the ability to understand different cultures and be in different rooms and understand what wealth look like and understand what struggle look like and being like a real fan of the things that I surrounded myself around. Let me respect these people in a different way.

And I never really asked for shit. Like that's not how I approach relationships. I got just, you know, there was periods of my life. where I would be that guy pitching you at the club or pitching you when I ran into you. But I quickly realized like, damn, nobody wants to hear that. You can't be that guy. So it was really just about forming these relationships

and finding my little ways to fit in, and my little pockets where I could create value. But the thing was is I always knew I was going to be so much bigger than what I was doing, but I was okay with sitting in that role at that time. I understand that so much. I wonder like when you were in,

in these rooms, in these very powerful rooms, if any of your sort of insecurities would bubble up. Thinking about insecurities from your past, did that ever happen to you? All the time. All the time, because when you don't have guidance as a young person and you have that type of chaos around you, you've lost all that validation that you need as a kid,

somebody to tell you like, you're the shit or you're going to be okay, and to mean it. which is huge, right? As a parent, you know that. Like, giving your kids this idea that whatever you do, like, it'll be all right. Like, there is a place and a space and, like, we've got you here. And when you don't have that,

it's incredibly difficult for people to understand who come from a background where you just have, like, regular supportive parents. Like, when your mom and dad have got you, like, you go home and there'll be food in the fridge and the lights are on and shit's just fine. And if you don't have that, it leaves you just without knowing.

And that is such a difficult place to be. Without question. Honestly, we've talked about this offline before. Like I can see a very clear kind of pattern with people that I know that no matter how much money they had or didn't have. If they had love and support and calm growing up, they didn't do whatever they want. One million percent. Because it is the basis and the foundation for this, I. idea of safety, like I will be all right. Somebody loves me. Somebody's got me. And I think that,

you know, again, we hear all of these stories of incredible founders and incredible entrepreneurs, but there is no mistaking the level of insecurity of when you don't have that, when your parents didn't provide that for you. And your baseline is just in an entirely different place. And I think that there has to be so much credit given for people that have to work their way up to just like the zero. Yeah. And the way it manifested in me was that how I presented myself on the outside, you may not have realized that. How I felt on the inside was like looking for that validation in so many different ways. And almost like feeling, you know, it's like if you if you produce something or do something and people like it, but you go home and you're like, God, that was like 50% as good as it really could have been. But everyone's telling you, man, I love that show you worked on. I love that new line you created. And you're like, that ain't it, though.

That's how I felt all the time. People will come up to me and say to me like, man, you're killing it, Rich. Like, look at these rooms you're in. Look at what you working on. Look who you're managing. And I would think to myself like, man, I'm not even half of the value that I could be right now. And how do I get myself confident enough to start to impose that more? What I realized now was that like not sure if that wasn't just the journey, right?

Like if I was 100% of who I thought I wanted to be at that time, like where would I be now? Right. And if I had told myself I was and acted that way, what would that have done? Right. And I think that was just the process. It's just what was happening internal was so much. It was just so much. It's just so much.

Yeah. Do you mind me asking what was, a relationship with your mother now? Like, where did you get to with her and how? Did she recover? No. So it's really, it's really sad because, you know, she ran out of all her money and I supported her at a young age.

And when I say supported her, it meant however I needed to get money. Like, it wasn't like I had her on payroll. It was just however I needed to get money. She never really got off drugs. She wasn't always there mentally. And the last. like eight, nine years, it was just too much to have her or have her around my children. But I still provided for her financially. I got her a place. I had an aid for her. Her mind kept going. And then

about five, six months ago, or maybe a little longer, I ended up finding her in her apartment. Then she went into ICU and then into hospice. And I will tell you, though, that by the time she was in hospice, she lost, she had lost her mind completely. And it was the most docile that I had ever seen her ever in my life. She was sweet. She was like a child. The conversations weren't that real, but there was one or two songs we used to listen to together

in some of our good times. And I played them and she started singing them. And I was kind of like, man, I needed this a little bit. You needed closure? Yeah, a little bit. Did you get it in that moment? I'm just getting it now. What happened was, is they called me from the nursing home.

They told me that, you know, she had stopped reacting to the stimuli or whatever, the stimulation. So that meant she was going to pass soon. So I said, can I come tonight, you know? And they were like, yeah, you'll be fine. And then they called me and they told me she passed. So I, like, ran up there, drove up there. And this is weird. I hope, like, your viewers don't think this is weird.

But when I went there, it was really cold. Like, the world is cold sometimes. Like I said to them, you know, where's my mom? They said, she's in her room, right? she had passed, they had cleaned that motherfucker out except for her on the bed. Like, everything was already gone. I was just like, this is crazy. So I went in there, and I didn't think I could be this person.

Like, if I heard myself or someone tell me the story, be like, what do you mean you talk to your mother after she passed? But like, something came over me, and I sat there and talked to her for like half hour. And I remember I said to her, like, I know you somewhere deep down aside, you did your best. And like, you didn't want this. and I do know you loved me. I said to her, I was like, I do know you loved me. Like, damn, you never showed it.

Like, but I do know you love me. And then I thought to myself, damn, this is the first time she's ever not interrupting me when I was talking. I was like, I've never remembered talking to my mom so honestly without her yelling at me or saying something. And I said goodbye. She wanted to be cremated. And I haven't done anything with the ashes yet because I can't fully recall something positive yet. So I'm trying to remember something positive. So what's happening now is my mind is clearing more and I'm no longer mad.

I have started having these like moments or memories of some good things. So I think I know what I want to do with it. But I'm at peace with it now, like for sure. It's heartbreaking. Yeah. That's a lot, isn't it? My God. Yeah.

Oh. I didn't need to get that to eat. No, it's just it's one of those things I think that, first of all, I was not expecting. you to say that at all. Sorry. I was expecting you to be like, yes, I've fully got closer. It's all fine. And onto the music business.

I know, but I think that your story will really resonate with people. And, you know, it's so interesting because when these things are real and, you know, when you have these really tough relationships, they don't just repair. It doesn't all just fall into place. I think it's kind of pretty amazing that you decided to have that conversation in the room. Like that, I'm sure you're going to look back in years to come and be so happy that you had that moment. Yeah, I feel that way. No doubt.

I'm going to call you in a couple of months and figure out what you did with those ashes. Yeah. Sure. What do you think, because you have two kids, in terms of the type of father that you have and how that relationship with your mom really informs that, like, where are you at? like what kind of parent and what kind of decisions are you making based on how you were raised? Absolute love and support at any cost no matter what. And it's not, I'm not perfect.

And there's certain things that I do where I find myself almost projecting on my kids, you know, getting on them about certain things that I'm really still getting on myself about. But they know how deeply I love them. They like, you know, everyone says that. but I absolutely adore my daughters, like truly. And I will forever do anything in the world for them. And there's nothing they can tell me that's too crazy. There's no feeling or emotion.

And pouring love into them and seeing them grow up and telling them that I'm doing the best I can, you know, and not necessarily being perfect and owning things that I do very quickly after. and talking to them like a real person. You know, like I don't have a guide, so all I can do is I'm a good person and I talk to them like a real person and I listen to them. And I know how important it is to just have that.

Yeah. Like, just have that. You ask somebody, you know I'm with you, period. I got you. You will figure life out. I got you, though, 100%. That's kind of all I need in life. So like to be able to know that they know that and to be able to know that I can do this forever.

You know, like I had a hard time when they went from being like babies to like, because the iPhone will fuck you up because you just scroll through that phone and there's like, there's your kid 12 years ago in one second. You die. And I remember I have such a insane. Like my memory is so clear all the way through my life that it's almost like a gift and a curse because it would make me feel so sad about them getting older. It would be like, God, I used to have breakfast with my older daughter every day. We used to call it like breakfast with Bella. And then all of a sudden, like, that's over. I collected snow globes every city I went to for her, no matter where I was in the world.

And then one day she was like, I'm trying to get rid of these snow globes. And I'm like, God damn. I was like 75 of them. So you're like, so you don't want one from my next race? You don't want to keep one? And then all of a sudden, I was. I was like, you know what, so what? Like, they're not going anywhere.

I'm not going anywhere. So let's just like enjoy every moment. No, and here's the thing. It's like you eclipse the curse, right? It's like for so many people, they aren't able to move on from what is that classic childhood trauma. It stops people in their tracks. You can either transform that and you can create an entirely different legacy with your own family or it stays with you and it destroys you.

And I've seen it on both sides. I grew up in a place that was full of that. my own family. And so I really believe that what you've done, not just becoming successful, but having this incredibly successful family when you had absolutely no basis, no example of that. That's the most successful thing that could possibly happen, that you're raising two brilliantly secure women that are going to go out into this world knowing it doesn't matter what, I am loved. I'm loved by my dad. Forget what that does like just for their business and work and professional lives.

It's like how you move through the world when that's your starting point is something I will always be mad jealous of. So good for you for being an amazing, amazing father. Well, I tell you the good thing was is I've been able to really establish that with my father the last few decades in my life, especially when my kids were born.

And sadly, you know, my father was a victim of my household too in a lot of ways. And, you know, I had no sympathy for him at first because it was like, damn, you're really leaving me here with her. But as I got older, like, you know, everyone's equipped to do what they can do. And he, he all, I knew he loved me always. So, like, knowing that is really, like, sometimes with your father all you really need. But our relationship is so strong right now. You know, he's one of those rare people that, you know, has this, like, understanding of taste and care.

and style. You know, you don't meet like many 80-some-year-old men that have had their whole life like that. And that's really rubbed off of me from like a professional standpoint, too. I think it's unbelievable when you realize what you got from your parents, like it or love that, you know? Yeah.

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While supplies last, ends June 30th, terms at AKA.m.m.m.m.m. Ambition comes in all shapes and sizes. At First Citizens Bank, we roll with your goals because we're built for what you're building. fit for your ambition for citizens back. All right, I want to switch gears a little bit and talk about you and work, because at this point, you're out there hobnobbing, mingling with the Hoypelois, as we would say in England, but it was Jay-Z, so we'll call it what it is. And you have this amazing success with this film, right? And I just want to talk a little bit about, because your career and your business

has been about these kind of transitions that you've made away from just being, and I say just, but away from being just a partner to talent from a kind of manager agent point of view. It's been about actually creation of businesses. So can you talk me through how that's happened and what that looked like in the early days for you?

Yeah. It was all really like every year is like a very clear phase in my career. So it was like I went to do music supervision on these shows. I started doing a handful of shows, all unsigned artists and producers. I started managing some of the people. producers. Then Mark asked me to partner with him on his label. I started working with him. We had a

studio down in Soho. Amy Winehouse recorded in that studio, Waleigh, J. Cole, all these people were coming through and it became this, like, creative vibe in the city. I also managed DJs. So I was in the clubs every night, Samantha Ronson, Mark Ronson, Q-Tip, D-Nice, had all these DJs that I was managing. And then I started managing artists. So it was like everything was like continuing to evolve. Mark at that point was building this incredible career for himself. And he had a separate manager now at this point. And we had the label. And I think in my mind, I was like,

damn, we're going to build something insane. But, you know, Mark needed to build Mark at that point. And the label was cool. And we had a great reputation. But it wasn't rapidly growing at the pace that I wanted. We just were kind of seen as this, like, creative hotbed down in Soho. We had a studio at 19 Mercer. And it was amazing.

It was my first, like, this is my office. But after I did fade to black, I got really close with all those guys. And when they started Rock Nation, I was able to get a bit of a structure for myself in my life for the first time. And also just to be around people that I was so enamored by. Totally. You know, and when you want validation, and that's what you're craving, and, like, that was another way for me to feel really validated.

You know what I'm saying? So I went over there, and at that point, I was just like a music manager. But it really was a glorious. days, right? Like, I remember Rock Nation wasn't just like, you know, another label. It was like, Rock Nation, Jay Z, Jay Brown, Tate it. Like, it was such a thing just to be around and in those guys' orbit was a big deal. Yeah. They were doing things. Yeah, without question. I mean, it was a, it was a complete gift. Like, I am not where I am today if I didn't have that moment in my life. I learned so much from watching, you know, and being around and being in an environment and, and also being

challenged, you know, like I had, I was challenged and I thought I knew what hard work was and I thought I understood how to be a professional. There was another gear. But I didn't have that skill set. And also, I was emotional. I was too emotional back then. Oh, say more, please. Would you mean you were too emotional?

I just took shit the wrong way, you know, and I, I, I over. thought things. And, you know, I took things personally, to be honest. And you didn't realize how that was negatively affecting you in business? Yeah, I was like, I was softer, honestly. And like, I don't feel that way anymore, so I can say that candidly. Like, again, you could have asked a hundred people if that's how they saw me. 99% of it would have been like, now, he ain't soft. That dude is killing it. He's doing great. But I knew, I knew that I wasn't even a fraction of. of who I wanted to be and what I was. But I still had residue.

Like I was still in it. It was still chaotic with my mom. It was chaotic with her till when I found her in her apartment. It never, ever, ever, ever stopped. Daily, messages, chaos, police at her house, the craziest shit. It never stopped, ever. So it always was in my head and it was just a lot.

And I had overcome the anxiety attacks, but like, I was like, you know, it was inside. And there's a heaviness. Like, it's your mom. Like, there's no escape in it. No, you're saying in East London. No escaping it. But you managed to have some distance in your own family because at some point, it's like you were working, you were making moves.

Like you'd figured out a way to like transition away from that chaos and build. Yeah, I started building something. I was like, you know, I don't want to make it's like I functioned. I got married young. I was operating at a very high level in some regard. But I had such big dreams for myself. I wanted so much. I wanted, it wasn't money.

It was regard. It was just feeling like I'm accomplishing some shit that my peers were respecting. And that motivated me, you know, like that might not be for everybody, but that motivated me. And I didn't have the skills yet. I didn't, you know, the thing is, is like, you can meet young. entrepreneurs and hustlers and all these like business minds and some of them are just unicorns right mark Zuckerberg unicorn j z unicorn michael reuben a unicorn kevin duran a unicorn they have to figure out life and emotions too but they're unicorns in that like they have the perfect combination and it works

and they're you can't replicate that you just can't so for me it was like i knew what i wanted to be be, but I had no understanding of anything. I had no understanding of how the world worked, really. It was all a blur. All I had was a high EQ, a good sense of humor, a good hustle, and a lot of friends. And I carried myself through life like that for a long time. But ultimately, some of those moments where I felt like, damn, why am I not moving any further? Why is this not happening for me? you know, I could have went one or two ways. I could have rested on my laurels around making good money, man, do some other shit.

That wasn't going to be it. Or I could say, like, how am I going to get better? Like, how am I going to get better? Do you think that's the secret to your success that you have looked at ways? Because, again, I feel like when you operate in circles where seemingly like everyone is making it, like, sometimes I can just, like, put you in your place. You're like, okay, well, I'm not one of them. so I'm going to stay in this comfortable place.

What inside you has just kept you moving and learning and keep going and going? Purpose. I have an understanding of what this all is. Like, we're unfortunately all here for a period of time, period. And if you think about every experience you have in life and like you think about you go on a vacation and you're like, how am I going to make this experience the most valuable for myself?

So maybe I want to get a massage or I want to bring some friends with me. I hope the sun is out so I can get a 10. I want to try some good restaurants. All you're doing is trying to do the best you can for that 10 days you're on vacation and make that the best experience you can have. Life is that. This is one long experience and moment. And my job in this is to make sure that my children can enjoy theirs for as long as they can and give them everything I can emotionally, financially, if it works for you. It's not always going to be. be what everyone can do. But for me, financially, for my children, experiences. But for me, I'm like, I'm here. Like, I'm not going to put this plan in place where, like, I'm going to work

till I'm this age and I want to then get a house there. I'm not scripting it. That's not how I'm going to live my life. I'm going to try to experience as much and enjoy as much and go as far as I can, meet as many people as I can, and create as much that I'm recognized for as I can. So that feeling is constant. I wake up with it every single day. I think about it every single day. What more can I do for myself, for my business, for my family, and I can only do it at my pace. And what I used to do is try to keep up with other people. And now I'm like, I'm not even paying attention to anybody else. And we all tell ourselves a story. We all paint a picture. You tell yourself a story of what your childhood is. And if you'd ask me all these things seven years ago, would have been different.

And the story keeps changing because it's your reality and your truth. And my thing is, is I used to tell myself certain stories about myself, and that's how I felt better. Now I tell myself the truth. And when I tell myself the truth, I know exactly what more I have to do and what I have to strive for and what I'm not. Like, I will not make myself delusioned in the thinking this is something it's not. I don't tell somebody that my business is bigger than it is. I don't tell somebody that I'm different than who I am. I'm really confident with where my feet are, but it makes me want to just keep going all the time. I feel like you just said so many things there that are, that that people need to sit with and listen.

This is the moment where you have to like rewind the podcast for exactly about 90 seconds and go through that again because you've said so many golden things there. But like what stands out to me, like when you talk about thinking about your life and viewing your life in the same way that you would have vacation, like really like thinking I'm going to do the best that I can, but then this being on your timeline, like that is golden.

And that's what I wish I knew. when I was 22 years old because I was always on somebody else's timeline. You were in this kind of like comparison game constantly and it just doesn't work. And I feel like the moment you wake up and usually it happens like too late, but you know, for me it was like mid-30s,

it's a game changer. You're like it's just me be me. Like nothing else. Nothing else matters. I'm going to just do everything that I can to be exactly where I want to be. And I'm not in a comparison game. It's so unbelievably freeing.

It's crazy. Talk to me a little bit about this kind of transition that you made in your career because I want to understand a little bit more about how you end up fully in sports and this relationship with KD. Yeah, so I had met Kevin while I was a music manager, Wale, who was an artist I was representing. And being such a big sports fan, I really went out of my way to make sure Kevin and I connected and that we had the ability to maintain a relationship even though we weren't working together. And around 2012, I just felt like I was operating with a bit of a ceiling. You know, if someone told you there was a ceiling, you would lose your mind. There can be no ceiling to where you go and what you want to do.

And I don't know if anybody put that in front of me. It wasn't like the ceiling was created by someone else, but I felt like what am I doing? Like, what am I doing? And I'm not even, I'm not even like fulfilled. I'm not having fun. And I was managing talented people at the time. I was managing salons, who was just glorious. So I still love to this day and talk to Meek Mill,

who's this young star at the time I was managing him. I was working Jay Cole with Waleigh. I still had business with Mark, even though he was like Mark Ronson now. And I was working for Jay-Z for God's sakes, right? It's that pretty tip of the top. It all felt great, right? You were good, right? But it wasn't giving me that feeling.

It wasn't necessarily to use my vacation analogy as like, I wasn't having a great vacation. I just wasn't loving it like that. And I thought to myself, what has always brought me joy? And that's sports and being around it. And, you know, Jay was always amazing. Because when I asked if I could get, you know, into sports a little bit, he said, you know, I think we're going to build something. And they gave me the ability to go do that.

And as soon as I jumped into that, I was like, oh, this whole outfit fits. Yes. This is me. This is what I'm supposed to do. And also, not only am I supposed to do it, I'm joining this world at a time where the model that the music industry had worked with and the model in which hip hop had worked with. This, like, creator economy really came from hip hop, in my opinion, where you had this star at the center and the entire ecosystem around you. And I get it. I speak that language and put me in room with any athlete ever,

and you'll think I was an agent for 30 years. So finally, I felt like, damn, I'm equipped for this on a different level. Sealing broke. I felt like, okay, cool, ceiling is no longer there for me. I can keep going. And I felt comfortable from day one. And every relationship, whether it's in business or personal, you can't explain it.

But when you meet that person, whatever it is, whoever the way to the world was supposed to work, it's like it just fits. Kevin and I just fit right away. Which is so amazing to me because you look at you and Kevin, you clearly have this amazing and beautiful partnership and an incredible business portfolio that you've built together. I wonder if, and I could be totally off track,

did you ever feel any sense of responsibility to him, like in a way of like, I'm going to be something to him that I didn't have in my own life, whether it be a mentor or partner. Like, what happened between you two that it just was so right? The thing is, is like, I know the way the sports world works, and I understand when you're an athlete of that caliber, what people tell you and what people tell you the right thing for you to do is. And I know for a fact that the majority of people around him were probably not telling him,

you should lock in with Rich. He's a music manager who's just moving over to being an agent. You should make him your guy. Yeah. That's not really the top of your game move. No. There's no way that someone would have told him. You let go of other agents.

They may have said, yeah, I understand why are you hanging with you. Yeah. He's a lovely man. Love it, but you can do better. Yeah. That can't be your guy. He didn't care from day one. And because of that,

I always feel responsible for him in every way, shape or form. Now, he gave me this like wind at my sales that I don't think I'd ever had. And I realized now, looking back on, I needed that. I needed somebody that I admired in such a level that believed in me and saw me in that way. And Mark did that earlier in my career too, because Mark saw me in the clubs and used to be like, I like the way you move in the rooms. I want you to run my label with me. So that was the first time I was like, oh, shit. Even Jamie Patrickoff. saying to me, hey, I want you to sit in this meeting for this show, or Jay, letting me produce this film. All of that was like that. But when Kevin Durant, at this point of his career

with where I was at was like, nah, I want you to be my guy. I just was like, man, I'm going to do everything I can to make sure this works. I wonder what made you so confident that you could run a business with someone like him, because you haven't just stuck to a traditional representation model. you also have an investment vehicle. Like what even gave you the idea that, A, you could do that, but that you could do it together with him? The thing was, is like when I started working with him

and we decided to work together like exclusively, at that point, I really wasn't necessarily motivated to sign other talent. I was really motivated to keep going deeper into what was possible for Kevin and I. And sometimes I feel like when you want to figure out a real move, a power move, and you want to figure out what it is that you're going to do, you have to simplify everything in your mind and streamline everything.

So the first part of our business was about making it as small as humanly possible. So we were like, all right, is your money right? Do we have good attorneys around you? What are we doing philanthropically in the community? Are your parents good? Or your family good? All right, cool. Let's deal with your basketball.

Like situation, contract. let's get sure that's right. Your Nike business, your anchor, let's make sure that's right. Okay, cool. All this is operating, you make a ton of money. Everything we do now from this point forward, I hope you want to do it because nothing else in your life do you have to do. But this is an exceptional piece of advice because people really overcomplicate things.

And what you said there was so beautiful because you said, when you are trying to do something, like simplifying things is the first thing. And I think that that is amazing. because that can apply to an entrepreneur, to a startup, to somebody taking on a leadership role in a company, like simplifying it down to the fundamentals and saying the Nike relationship is in check and my family's in check and this piece is like, boom, bomb, bomb. And that is, that can apply to anything. It's an amazing approach because that stops you from being overwhelmed and it allows you, once the, once the kind of fundamentals are good, then you can figure out all of this other stuff.

and it kind of doesn't really matter if it doesn't work that well either because you've still got the baseline. Without question. We've got the good stuff. The core of it is down. Yeah. And we got reps. Like as partners,

you've got to earn that trust over and over again. You've got to get reps. You've got to figure out how you both dance. Like, how does this work? Like, how do you receive when I communicate? How do I hear what you're saying to me that you want or don't want? And how do we make strategic decisions on things that you are motivated, by that you want to do, you know, a lot of times talent finds themselves on this hamster wheel

of like, ah, so many things that I do. Yeah, well, they're inundated. Their deal flows crazy because everyone wants them and everything. But how do you guys decide what's going into 35B, like, and what's not? Because I'm sure you have so many opportunities. Yeah, I mean, it's just evolved over time. When Kevin played for the Warriors and I lived out in the Bay half my time, our proximity to Silicon Valley and these just like incredible founders and incredible VCs afforded us great deal flow.

Did you do some good deals? We did. Did you catch some good stuff from the tech bros? Yeah, we caught some good unicorns from the tech bros and we missed on a lot. But we learned a lot and I wasn't outside my pocket. We stayed really early stage. We made a lot of bets. There was a lot of learnings.

I felt like in a lot of ways, the pay to play. And I believe in that model at an angel seed level. I got founders that became part of my network. I learned about different companies and different approaches to business. It was probably my best education to that point in my life, just being able to go deep with some of these founders and understand the mechanism in which their business was built and to learn from these different VCs.

And that whole experience just opened my eyes to everything. You know, it's like our whole foundation and our whole philanthropic footprint was kind of built from dinner with Lorene Jobs and Ron Conway and just like me having no fear asking how we should approach things. And it was just an incredible time in my life. And I almost feel like that was my college, those three years there. No doubt. Which of your business decisions almost like is the best reflection

of how far you've come as a kid with no blueprint? That's a really, really good question. I would say navigating Kevin. free agency in 2016, just because of the magnitude of it, that it was really on me, that there wasn't somebody else. You know, there's a lot of times when you're younger, it's really easy to just assume, you know, it's like when people say like, oh, that'll never happen. Or, you know, my mom said that's not true.

And that's like really all you need to know, right? So as long as you know if there's someone else that will figure it out or someone else that might solve it for you. You can operate with like a little bit of comfort. But that really made me realize like, all right, I'm going to operate this free agency. And I'm going to have the owners of all these teams and star players and legends come to meet with Kevin and I.

And I'm going to talk on his behalf. And I'm going to represent him and this next step in his career. And when we got through that, it was kind of like, okay, I see where we can go together now. And I can see what I can do. Tell me a little bit more about what you're building together with Bordroom and how that differentiates from the competition. Yeah. So the way we did this was as 35 Ventures was being built, that, like I said, became the home for our investments and Kevin's brand business and some sports investing and fun things we experiment on, like a restaurant or a hospitality venture, all fall in 35 ventures.

boardroom to me was meant to, you know, when you think about the publishing world, you think about Vogue and GQ and Vanity Fair and Forbes, right? So the narrative around that business for a long time has been like that that model's broken. And the way it was doesn't work like exactly the way today. But the strength of those brands and like the premium value of those brands always stuck with me. I thought it was such an incredible. incredible connection, like the way people wanted to read these books and these magazines. And digital media is not like that.

No, you're totally right because Forbes is still Forbes and Vogue is still Vogue. And it means something. Yeah. So for me, it was like, I want to build a brand today. The model will be different. How we generate revenue and how we create our audience will be different. But I want to build a brand that can sustain that embodies this culture today, this intersection, this world of sport and technology and entertainment,

this world where you know David Blitzer and David Blitzer knows 21 Savage and 21 Savage knows David Solomon and David Solomon knows Sabrina Ionescu. And to an outsider, they're like, how? How does all that make sense? We know how that makes sense. And that world is so powerful. And I want to be the brand and the voice and the storyteller in that world. And we're building it block by block.

and I've been methodical and patient and intentional and it's working. And that's what's exciting for me. It's really working, isn't it? It's that really tracking because I have to say I knew about Bordering before I knew that it was you. And that's what to me, it's like not me supporting my friend. This was just like a thing that I was like, well, this is just part of my media mix now. This is just something that I have to read and understand and be part of. And I think I was on some list somewhere that I was very happy about.

But you know what I mean? But it took me a wire. before I was like, oh, oh, that's my rich. Like, I had no idea, really, because I saw you in a different world. So, I mean, congratulations to you. It's something pretty amazing. Kayak gets my flight, hotel, and rental car right. So I can tune out travel advice that's just plain wrong.

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Anywhere. What about fancy places like the canopy in Paris? Yeah, Hilton Honors, baby. Or relaxing sanctuaries like the Conrad in Tulum? Hilton Honors Baby. What about the five-star Waldorf Astoria in the Maldives? Are you going to do this for all 9,000 properties? When you want points that can take you anywhere anytime, it matters where you stay.

Hilton, for the stay. Book your spring break now. So before we wrap, a quick reminder that start with yourself is available for pre-order and tickets for the live shows are available now. Starting April 15th, we're coming to New York, Los Angeles, San Francisco, Chicago, D.C., Boston, Atlanta and London. Visit emigree.com for tickets and full tour details. I cannot wait. I want to ask you a bit about leadership

because you don't get to where you are in life without being a good leader and having people that are willing to follow you. Is there some type of mantra or something that you have that informs the type of leader that you are now? It's always evolving. I will say, and not to gas you,

but a lot of things that you have said on your show, I and some of my colleagues at my office have shared with each other because you have an incredible perspective and a kind of practical point of view on things that have been helpful for me, even how I look at people that work for me and how I have to communicate with them. So I appreciate that. You really do say some incredible things that have helped me as a CEO and a leader.

I think the reason I've gotten better now, I think over the last few years, is I'm always going to be kind. That's just the way I am, right? Kind of a bloody long way. Don't be an arselle. It's a great leadership lesson for everyone. I'm always going to be kind, and I'm always going to respect the other part of your life, right?

You work for me, but you have a whole other part of your life, your family, your insecurities, your responsibilities. I'm always going to respect those. A lot of people, when I was coming up would say, man, I don't want to hear about that shit. Like, everybody got shit. You got to work. I believe you can do both, but I respect that.

I respect it and I use that for me to, again, like I said earlier, start to look at the people that I'm leading and say, wow, you know, let me make sure that I understand the full scope of what they're going through, right? Well, you have empathy that comes from experience. Yeah. But where I've changed or where I've gotten better, and it took me a while was when your whole career, is built on being liked and being connected and being welcome and having this robust network of

people from all walks to life to be able to make really harsh, cold decisions to let go of people to decide to say no to something. It was a little bit of a challenge for me because my instinct was always to make sure everybody was good with me all the time. And it's changing because I realize that what I'm building is what I wanted to build. It's something that I feel really proud of and that I think could be special. And what I know now is that, sadly, to get to where I want to go, I'm going to have to allow myself to make decisions that people won't always like me. Yeah, fair enough.

I mean, can't be a people pleaser and a leader. I mean, I say this all the time. I wonder if just your experience, because you seem to be someone who has a pretty good grasp of what's going on in the wider culture. When you think about your organization and you look at the men and the women, and let me tell there will be a lot of women that are listening to this show, do you see big differences in the way that men move their way through their careers, your companies and the way that women do in like leadership perspective, in the style?

I just wonder as a man in leadership and running a company, what you see. To be honest, this is going to be maybe controversial. I don't think men work as hard. That's not what I was expecting you to say. Tell me why. Say more. Keep going. I don't know.

From my experience, you don't think men work as hard? For the business or like in the way they come into the office? You think women work harder? Yeah, I really do. I ain't going to disagree with that. Listen, obviously it's not a universal thing. No, absolutely.

This is all about just our experience and our own observations. Yeah. For sure. Yeah. I really do. Which is kind of insane considering that, you know, if you were to look at it, statistically, women move up a lot slower. So maybe something for our other male counterparts to think about.

Isn't it just? Yeah, but the facts are the facts and the numbers are the numbers. And I think that, listen, I'm the first person to take responsibility. for behaviours that affect the way that women are treated in business because I think that it's my responsibility to bring that to our consciousness and our attention. But it would not be an unfair reflection to say that women work unbelievably hard compared to the opposite sex. And yet, the ways that they get promoted are not nearly as fast.

Without question. Without question. We're going to move on, just saying people. I want to talk a little bit about money, because you know I love to talk about money. your relationship to money as a child, what did that look like? And how does it impact the way that you think about money now? It was such a source of conflict in my house. It was such a fight over money. My family talked about it. They talked about what they didn't have, but they did have who didn't give them something, what wasn't fair. It always made me really uncomfortable, but I always wanted to

make money. And I started as I got older realizing that like I want to make a lot of money. I like making money. I really do. But being stressed about money and having the fear that you can't pay your credit card or you can't even like withdraw money from your ATM, that's the worst feeling in the world. It's an absolute deflating feeling. And I have been there. And, My first goal was to not have to feel that way. That was my first goal. And because I don't feel that way anymore, my relationship with money is secondary to my relationship with my career and my profession.

Fair. I want to work hard enough so my kids never have to feel that ever and their kids. That'd be great. I don't want it to be a part of a conversation in my household and it never is. I think that's a really unhealthy environment to create. And I think you should get rewarded and valued for your work. And I feel like I deserve to be rewarded and valued for my work. And I will advocate for like getting what I think I deserve.

And that has taken time too because, you know, when you're coming up, you don't know if you see yourself exactly that way, right? Every first check you make, you're like, goddamn, back of your mind. I can't believe they paid me that. And then all of a sudden you start to realize like, nah, you're worth more than that. I mean, I took a walk over the summer with Rubin, and he said to me, you got to start asking for three times more for every deal. And it was like so simple, but it was like a... Sounds like Rubin.

Yeah. And I was like, you're damn right. Like, it's how you value yourself. So I think for me, it's like, as long as I don't have to ever stress money and my family doesn't have ever to stress money, I'll be happy. I'll be happy. I tell you what, that's just such good advice from Rubin. I got very, very similar advice when I was a kid from the only person I knew who made money and he was a football agent, soccer agent in England. And I was like, I just don't make enough money from my deals. And I worked so hard and I put so much in. And he's like, what did you charge? I was like 10%. He was like, charge double. And it worked. No one ever blinked. No one was ever like, you're taking 20%.

I was like, I take 20%. I take 20%. And it was like, I'm making double. Like what? Sometimes sometimes you just don't know what you can do and what you can ask. And we all need a Ruben telling every now and again. It was so, but you know, the most simple and practical responses that you usually get from super successful people are really just always ring true. Totally. Totally. Is Ruben someone you would consider a person you call, a person you chat and talk to about

business things? Yeah, a lot. I feel like he's out for so many people. Yeah. I call him. Yeah. He's generous with the information as well. He is.

He is. And also, like, people like him. refine their own skills in giving advice to people too. So as you're giving someone feedback and advice, because I feel it too, when people come to me for advice, because I serve that purpose for so many people, I'm learning as I speak to people

because I'm giving them advice and I'm like taking an inventory while I'm giving them that advice. Fair enough. Am I doing that? Yeah. Am I actually listening to my own advice? What's the most expensive lesson

that you've ever learned about money? I think when I was younger and I went from being a bookie and I stopped booking and I had a lot of cash and I really thought I was Ace Rothstein from casino for a while and I started flying to the Bahamas and gambling and just living recklessly with my money and then one day I opened up that safe and there was nothing in there and I was like did I just spend all that fucking money? And it was pretty helpless feeling because I had never had it and then it was gone. And I think I started to kind of value it a bit more at that point. Yeah, I think that's right. That'll be about right. Do you think that you took more financial risks early in your career, or do you take more now? Earlier, I think I vested myself.

I did whatever the fuck I had to do to be there. I used to think to myself, you know what? If I, like, whatever it takes. If I got to be in that room and it costs that, I'm going. However, I got to do it. Yeah. I'll figure it out next week. Yeah, exactly.

I took risk all the time. I'll figure it out next week. Yeah. I want to just talk to you a little bit about the future and legacy. And I hate to kind of put it in that way. But, you know, you can think about it as like growth or reflection. Is there any part of you that still feels like you have something to prove? 100%.

100%. To myself, to my family, to my peers. I feel that way all the time, yeah. I fell out way all the time. Why? How so? Because I don't think I even understand how broken I was. And I feel so proud of myself that I climbed out of it. Like, I really do.

It really should have and could have ended really bad. It was fucked up. And trying to get out of it and trying to prove myself to myself and the people around me became such a motivating and powerful feeling. So I can't ever let go of that ever again. I can't ever not feel that way. I can't ever feel like I don't have to prove myself to myself. And also, like, putting business aside,

I would like to keep evolving as a human being and keep refining who I am and keep getting better. You know, I really want to keep getting better and keep figuring out how to communicate better, keep figuring out how to learn more, how to meet new people, take care of myself more. How much as that is for yourself versus for other people?

When you talk about keep getting better, keep learning how to communicate, is that for you? Or is it for the people around you? It's for me. Because, listen, I think my kids will always benefit from me as a father, continuing to get better as a person.

But I think that, again, similar thing to what I was saying about like how I don't ever want to feel like there's no money in the account. I don't want to feel that feeling that I used to have as a kid, that fear and anxiety that I massed and went out into the world. I don't like feeling like that. I don't want my head spinning in chaos anymore. And I know life will, things are going to happen in life. But I really feel calm amidst all that now. And I think for me, it's like if I can keep evolving and getting better and understanding myself and understanding the world and learning how to talk better to people, and then all

us is going to feel better. Like, why are we here if we're not going to figure it out and keep evolving and understand? I couldn't agree with you more. I think that, like, the point of life is for you to continuously be in learning mode and for you to continuously be getting better. And also, you know, in my old age, like getting closer to yourself and understanding more about you and kind of quiet in that noise and understanding that this is how I do things. This is who I am. And these are the places that I need to work.

That is the point. Yeah, that's the entire point. What's the ultimate goal for you in business when you think about 35B and boardroom? Like, what are you trying to do now? So it's very clear goals I would say on both. You know, I think for 35V, Kevin worked his ass off his entire life to be who he is and to play at the level that he plays at. And he's taken care of a provided for so many people. And, you know, I think I always feel motivated to build opportunity for him, to build legacy

for him. We're doing a ton of development in real estate in his hometown. And there's certain things I knew he always wanted to be a part of, whether it was investing in sports teams, that I feel a lot of pride and continue to build for him and making sure that his legacy and his business is running for generations. That's my job as a manager. That's that manager had. On the boardroom side, I really want that feeling that like they used to say that contractors had or construction people when they would drive into the big city with their kids and go, Daddy built that building. I want a company that lasts and sustains. And because of that,

I'm being very strategic with what I want the outcome to be. So there's certain companies that I'm eyeing that I would like to at some point partner, acquire, and help supercharge my business. And the way I'm thinking about it is not about how much money they will give me. It's about will I be able to sustain and operate and grow within a bigger ecosystem.

I think there's nothing cooler than being able to point in 20 years, 25 years, and say to my grandkids, like, I built that magazine, that whatever form that comes in, or whatever your glasses are displaying to you. I built that, or that brand that embodies this world and this, and this, like, space that I love. I've loved it my whole life. I want something that lasts.

And maybe I'm naive, right? And maybe it's just what it is, but that's what motivates me. Maybe you'll have exactly that. Yeah. I have no doubt. All right, we're going to move to some rapid fire questions. All right, I'm terrible at rapid fire because I don't do anything rapidly, so don't worry if they're not quick. All right, what is the most underrated business skill?

Most underrated business skill of patience. That's a good thing. Three things that you can't live without. Diet Coke. Sadly, my phone, my fam. Give me a Diet Coke, my phone and my fam. It's a Friday night. What's your favorite pizza spot in New York City?

Either Luke Cali or Don Antonio. Two good answers. Is there a book that changed your life? The War of Art of Art, which is... Art of War? No, the War of Art. The War of Art? Yeah.

What is the War of Art? It's the opposite of the Art of War. Is it really? Yeah, and it's a small handbook. Yeah, you should read it, actually. Well, clearly I need to now because I was about to up your whole answer, the war of art? Yeah.

Okay, it's going on the list for sure. All right, what is something that you used to aspire to that you no longer aspire to? I don't know, because honestly, I've always aspired this. Like, I wanted to be around this world since I was young. I mean, I guess if there was one thing, maybe it was that, like, I thought that, like, not fame, but I thought that there was a certain level of like notoriety that you should have and then success will come. And I think what's changed is like it's not as important to me and it is clear that it comes

with success, right? It's like everyone knows who you are now and this is a result of your success. So I think I had that backwards for a little bit. That's a great answer. All right. last question for you, what is it that you most aspire to now? To be honest with you, I am really focused on, like, trying to figure out how to be best friends with my daughters.

They're at a point in their life right now where we are super close and I adore them and I believe they adore me. But it's tough when you have teenage girls to like connect on. every level. And I think for me, it's like, when I see friends of mine whose kids are their best friends, I feel like that's like what life is about. And I think I'm headed in that direction. But I really want to make sure I like create an environment that allows that. Because I don't think I'll need anything else in life if later on in my life like my girls are my best friends. Beautiful. Best answer ever. You're amazing.

Thank you, my darling. I loved it. If you're loving this podcast, be sure to click follow on your favorite listening platform. While you're there, give us a review and a five-star rating and share an episode you loved with a friend. You'll be so grateful. Aspire with Emagreed is presented by Audacy. I'm your host, Emma Greed. Executive producer Ashley McShan, Derek Brown and me. Our executive producers from Odyssey, Leah Reese Dennis, Asha Saluja, Lauren Lagrosso.

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