What Growing Up in Chaos Actually Teaches You (Rich Kleiman)

24:42So 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 gotta be in the music business.

25:12Yeah, 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, OK, I got to do something. Like I missed the booking side of my life a little bit.

25:45You missed the money? I missed the money or just like feeling like in control of something. 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 founder, this 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 was very pioneer then. The idea was just like community commerce content, really what boardroom is.

26:22Wow. 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 at 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.

26:56And I know how I can be successful and powerful. And I got to start this journey. And that was like the music business. Like I'm going to be in that. 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 De Niro. And that was just me hustling in New York.

27:29Pretty good. 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. 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 finished and life has like been this like 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.

28:09And a mutual friend of ours, Jamie Patrickoff, 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. Cause 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.

28:47Oh yeah, that'll get you.

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30:17do you think that like 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 yeah anything or what no no no blueprint no game plan no rule book no guardrails and were you scared no no no no No, never. There was no fear of like, I could fuck this up. Nah. 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. Scared was normal. So for me, I was just like, this is fun.

30:55Like 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 way to trust your own instincts? If you just, that you didn't have a choice. So you just were like, okay, what do I feel? And you went for it. You ever, you ever see Good Will Hunting when, when Robin Williams says to Matt Damon, like, who challenges you? And he was like, what do you mean? And he was like, Shakespeare, this person, that person. It wasn't like that for me, but my mentors were who I watched.

31:30Like 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, and when I took that role 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.

32:07And because my relationships with 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 to Radical Media and Jay had had this incredible footage from Madison Square Garden.

32:43And next thing I knew, I found myself a producer on a film of one 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 could 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 looked like and understand what struggle looked like and being like a real fan of the things that I surrounded myself around.

33:35Let me respect these people in a different way. And I never really asked for shit. Like that's not how I approach relationships. Like I just, you know, there was periods in 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.

34:15I understand that so much. I wonder like when you were 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 will be all right.

34:56Like 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, you know, and 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 can do whatever they want.

35:42One million percent, because it is the basis and the foundation for this 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 you, 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.

36:32Yeah. And almost like feeling, you know, it's like 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 or look at what you're 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.

37:08And 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 a hundred percent 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, you know, it was just so much. It's just so much. Do you mind me asking what, what's the relationship with your mother now? Like where did you get to with her and did she recover?

37:50No. So 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.

38:35Then she went into ICU and then into hospice. And I will tell you though, that by the time she was in hospice, she had lost her mind completely and 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? Hmm. I'm just getting in now. What happened was, is they called me from the nursing home.

39:14They 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.

39:47Like 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 this story, I'd 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 the side, you did your best. And like, you didn't want this. And I do know you love me. I said to her, I was like, I do know you love me. Like, damn, you never showed it. Like, but I do know you love me.

40:20And then I thought to myself, damn, this is the first time she's ever not interrupted 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, 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 it's a lot isn't it my god yeah oh 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 to be like yes i fully got closer it's all fine and onto the music business um 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.

41:34It 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. 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, where are you at? What kind of parent and what kind of decisions are you making based on how you were raised?

42:16Absolute love and support at any cost, no matter what. And I'm not perfect. And there's certain things that I do where I find myself almost projecting on my kids, getting on them about certain things that I'm really still getting on myself about. But they know how deeply I love them. Everyone says that, but I absolutely adore my daughters, 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.

43:10So 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.

43:49You 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, 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. That was like 75 of them. So you're like, so you don't want one from my next place.

44:28You don't want to keep one. And then all of a sudden 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 like 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 in my own family.

45:03And 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 just for their business and work and professional lives. It's like how 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.

45:44Well, I'll tell you, the good thing was, is I've been able to really establish that with my father the last few decades of my life, especially when my kids were born. And sadly, my father was a victim of my household too, in a lot of ways. And 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, everyone's equipped to do what they can do. And I knew he loved me always. So knowing that is really like sometimes with your father, all you really need. But our relationship is so strong right now. He's one of those rare people that has this understanding of taste and curation and style.

46:31You know, you don't meet like many 80 some odd year old men that have had that their like whole life like that. And that's really rubbed off on me from like a professional standpoint, too. I think it's unbelievable when you realize what you got from your parents. Like it or loathe it, you know. Yeah. I think about it all the time.

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49:25All 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 hoi polloi, 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.

50:00So 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 of 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 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. Wale, J. Cole, all these people were coming through and it became this creative vibe in the city.

50:35I also managed DJs. So I was in the clubs every night, Samantha Ronson, Mark Ronson, Q-Tip, Be 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 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.

51:12We just were kind of seen as this like creative hotbed down in Soho. We had a studio at 19 Mercer and it was amazing. That 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 Roc Nation, I was able to get a bit of a structure for myself and my life for the first time. And also just to be around people that I was so enamored by. 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.

51:47But it really was the glory days, right? Like I remember Roc Nation wasn't just like, you know, another label. It was Roc Nation, Jay-Z, Jay Brown, Tatey. 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 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 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.

52:28There 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. What do you mean you were too emotional? I just took shit the wrong way, you know, and I overthought 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 100 people if that's how they saw me. 99 % of them would have been like, no, he ain't soft.

53:06That dude is killing it. He's doing great. But I knew, I knew that I wasn't even a fraction 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 escaping it.

53:51Your mom's your mom. Literally and figuratively no escape, 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 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 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.

54:30And 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, Jay-Z, unicorn, Michael Rubin, a unicorn, Kevin Durant, 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 you can't replicate that. You just can't. So for me, it was like I knew what I wanted to be, but I had no understanding of anything.

55:14I 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 about 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?

55:57Because 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. It's 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?

56:36So 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 tan. 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. That's not always going to be what everyone can do. But for me, financially, for my children, experiences.

57:13But 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 sage 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.

57:51And 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 had asked me all these things seven years ago, it would have been different. And the story keeps changing because it's your reality and your truth. And my thing 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 into thinking this is something it's not.

58:24I 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 people need to sit with and listen. like 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, and, and, and viewing your life in the same way that you would a 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.

59:06And 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 thirties. 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 like fully in sports and this relationship with KD.

59:50Yeah. 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, like I really went out of my way to like make sure Kevin and I connected and that we had like the ability to maintain a relationship, even though we weren't working together. And around 2012, I just felt like I was, 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?

1:00:34Like, what am I doing? And I'm not even fulfilled. I'm not having fun. And I was managing talented people at the time. I was managing Solange, who was just glorious, who 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 J. Cole with Wale. I still had business with Mark, even though he was like Mark Ronson now. Um, and I was working for Jay-Z for God's sakes, right? Like that pretty tip of the top. It all felt great, right? But it wasn't giving me that feeling. It wasn't necessarily to use my vacation, um, analogy is like, I wasn't having a great vacation.

1:01:15I just wasn't loving it like that. And I thought to myself, what has always brought me joy? Like, and that's sports and being around it. And, you know, Jay was always amazing. Cause 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. 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.

1:01:53This 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 in a different level. Ceiling broke. I felt like, okay, cool. Ceiling is no longer there for me. I can keep going. And I felt comfortable from day one. Um, 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, it fits.

1:02:39Kevin 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, is there, 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, a 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.

1:03:23And I know for a fact that 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. Maybe let go of other agents. they may have said yeah i understand why are you hanging with you but you can do better yeah that can't be your guy he didn't care from day one and because of that And I always feel responsible for him in every way, shape or form. Now, he gave me this like wind at my sails that I don't think I'd ever had.

1:04:08And I realized now looking back on, I needed that, right? 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 in his career with where I was at was like, nah, I want you to be my guy.

1:04:44I just was like, man, I'm gonna 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.

1:05:27And 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? Are 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.

1:06:00Let'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.

1:06:41And this piece is like, boom, boom, boom. 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. It's like, we've got the good stuff. The core of it is down. Yeah. And we got reps like as a, as partners, You got to earn that trust over and over again. You got to get reps. You got to figure out how you both dance.

1:07:11Like, 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 flow is crazy because everyone wants them and everything. But how do you guys decide what's going into 35V and what's not? Because I'm sure you have so many opportunities. Yeah. I mean, it's just evolved over time.

1:07:48When 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, we had to pay to play. And I believe in that model at an angel seed level.

1:08:26I 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.

1:09:00And 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's 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, 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.

1:09:42And 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 like solve it for you, you can operate with like a little bit of like 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, see what I can do.

1:10:17Tell me a little bit more about what you're building together with boardroom 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 on 35 Ventures. Like 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.

1:11:04But the strength of those brands and like the premium value of those brands always stuck with me. I thought it was such an incredible connection, like that the way people wanted to read these books and these magazines. 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. 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 perfection 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 uh Sabrina Ionescu and to an outsider they're like how how does all that make sense well 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.

1:12:07And 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 really tracking because I have to say, I knew about boardroom 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. Like 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?

1:12:37But it took me a while before I was like, oh, that's my reach. I had no idea really because I saw you in a different world. So, I mean, congratulations to you. Thank you. It's something pretty amazing.

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1:14:56Visit emagreed.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.

1:15:42So 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. Um, that was a bloody long way. Don't be an arsehole. 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 with say, man, I don't want to hear about that shit.

1:16:28Like 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 and where I've gotten better, um, 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 of life, to be able to make really harsh, cold decisions, to let go of people, to decide to say no to something.

1:17:19It 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. Fair. 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.

1:18:03When you think about your organization and you look at the men and the women, and let me tell you, there'll 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? Like, 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?

1:18:47I mean 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 gonna 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. That's obviously more of a sad reflection of our society. Isn't it just? Yeah, but it's also... But the facts are the facts and the numbers are the numbers.

1:19:23And I think that, listen, I'm the first person to take responsibility for behaviors 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 or vast. 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?

1:20:05It 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, what 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.

1:20:52And 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.

1:21:32And 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, God damn, back of your mind. I can't believe they paid me that. And then all of a sudden you start to realize like, you're worth more than that. I mean, I took a walk, I took a walk over the summer with Ruben and he said to me, um, you got to start asking for three times more for every deal. And it was like so simple, but it was like, sounds like Ruben. Yeah. And I was like, you're damn right.

1:22:02Like 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, you'll be happy. I'll be happy. I tell you what, that's just such good advice from Ruben. 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'd you charge? I was like 10%. He was like, charge double. And no one ever blinked.

1:22:31No one was ever like, you're taking 20%. I was like, I take 20%. I do these sponsorships. I take 20%. And it was like, I'm making double. Like what? Sometimes you just don't know what you can do and what you can ask. Yeah. 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 the 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.

1:23:07Yeah. I call him. Yeah. He's generous with the information as well. He is. He is. And also like, um, people like him refine their own skills in giving advice to people too. So as you're giving someone feedback and advice, cause I feel it too, when people come to me for advice, cause 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. 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.

1:23:56And 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 I, 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 invested myself. I did whatever the fuck I had to do to be there.

1:24:31I used to think to myself, you know what, But 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 risks all the time. That was always my thing. 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? A hundred percent. 100 % to myself, to my family, to my peers.

1:25:11I feel that way all the time. Yeah. I feel that 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.

1:26:08You 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 is 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.

1:26:48I don't want to feel that feeling that I used to have as a kid, that fear and anxiety that I masked 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, 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 I just can 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 quieting 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.

1:27:51Yeah, that's the point. It'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 35B, 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, 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 in continuing to build for him and making sure that his legacy and his business is running for generations.

1:28:42That's my job as a manager. That's the manager hat. On the boardroom side, I really want that feeling that 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?

1:29:28I think there's nothing cooler than being able to point in 20 years, 25 years and say to my grandkids, I built that magazine, 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 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.

1:30:09So don't worry, they're not quick. All right, what is the most underrated business skill? Most underrated business skill, patience. That's a good aim. Three things that you can't live without. Diet Coke. Sadly, my phone, my fam. Give me a Diet Coke, my phone and my phone. It's a Friday night. What's your favorite pizza spot in New York City? Either Lucali or Don Antonio. Two good answers. Is there a book that changed your life? The War of Art, which... 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.

1:30:57Yeah, you should read it, actually. Well, clearly I need to now because I was about to mess 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.

1:31:45And 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 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 like their best friends, I feel like that's like what life is about.

1:32:39And 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.

1:33:04If 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. A Spy with Emma Greed is presented by Odyssey. I'm your host, Emma Greed.

1:33:44Delgado. Social media by Olivia Homan, Catherine Bale. Special thanks to Brittany Smith, Sydney Ford, my teams at The Lead Company and WME. Maura Curran, Josefina Francis, Hilary Schuff, Eric Donnelly, Kate Hutchinson-Rose, Tim Meekle, Sean Cherry, and Lauren Vieira. If you have questions for me, you can DM me at Aspire with Emma Greed. Greed is spelled G-R-E-D-E. That's Aspire, A-S-P-I-R-E with Emma Greed. Or you can submit a question to me on my website, emmagreed.me.

1:34:43So put that fork down. Try the new wraps today in app or at order.sweetgreen.com. Available at participating locations only.