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

So today I am so excited for you to meet one of my old friends and colleagues.

I've known Rich Kliman 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 gonna do today, but the reason I wanna 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.

I cannot wait for you to watch this one.

And don't forget, before we get into this, to like and subscribe.

Do you see big differences in the way that men move through their careers and the way that women do?

I don't think men work as hard.

Rich Kleiman built one of the most powerful careers at the intersection of sport, music, and business.

But the skills that got him there didn't come from a playbook.

My house was volatile.

It was so bad the way they fought, my parents.

I know I'm the right person to navigate through chaos.

Sometimes the things you learn just by trying to survive early in life become the skills that give you an edge later on.

You always imagine that your childhood trauma will only have negative effects on you, and everything that you described is actually a superpower.

No blueprint, no game plan, no rule book, no guardrails.

And next thing I knew, I found myself producer on a film of one of the most iconic individuals of our lifetime.

Most opportunities don't come with instructions.

The real skill is recognizing the moment and stepping into it.

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 used to tell myself certain stories about myself, and that's how I felt better.

Now I tell myself the truth.

The hardest story to change is the one you tell yourself.

Is there any part of you that still feels like you have something

to prove?

Rich Klyman, welcome to Aspire.

Oh my God, I am so honoured 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 with anyone that might be watching this because I've known you for 20 years.

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.

Media Rich.

I love this.

But we've actually never spoken about young Rich.

Which is where I really wanna 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 and 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 holdco for Kevin Durant 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 Boardroom 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 and 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 7 years old, I launched this business called Loya Kid.

And 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, like, 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, 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 could 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 Roc Nation.

Yeah.

No, no, it was actually before that.

Did I meet you before that?

Yeah, because 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 Marc Seliger photograph.

Oh, wow.

And it was Marc for GQ or for Gucci something.

Something.

Yeah.

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 got it.

Down, everybody knows him.

And I literally forget Mark Ronson, as lovely as he is, but I was like, I'm gonna 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 do you want?

And I was like, everything.

Yes.

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, um, you know, managers, agents, publicists, they 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 'cause 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 runt of the, like the broker.

Like nobody cares about the broker.

It's like you've either got something to bring and if you don't, somebody else will.

And it says a lot about the type of person that 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.

Let's start at the beginning.

I wanna 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 KD.

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, like, background.

Yeah.

I grew up in New York City on the Upper West Side.

And 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 slummin' 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 parents were like 10, they sat us down and told us they were getting divorced, and I flipped out.

And then like 2 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 4 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 I stayed with my mom because back then that's what you did.

You stay with your mom.

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 like addicted to drugs.

She

was completely like 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 obviously very emotionally insecure.

Were you financially insecure too?

No, it wasn't like— we were good.

We didn't— 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.

'Cause when I was home, this shit 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.

Oh, shit.

She 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 a Burger King on Broadway.

And we just chilled, and it allowed me the ability at times to be around people that also had 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.

I applied to 8 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.

I phoned in every single thing I did.

I hustled my way through.

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 like 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, no learning problems.

If anything,

I, 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?

Because I— 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 7 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, um, you know, no matter what's going on, like, my heart doesn't ever race like that.

My 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.

I'm like, 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 gonna 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 in business and everything you do in life has gotta be a battle, that ain't for me.

I don't have the eye, 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.

But 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 mum, you Being empathetic and then finding that in situations and being able to say, in this negotiation,

what's happening on the other side of the table?

Like, 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 the businesses that you do now.

It's pretty extraordinary, really.

Well, 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 this 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.

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 wilding 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

It, in my opinion, 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.

Like, 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— I loved making the money.

I love dealing with people.

Do you remember how much money you were making then?

I made good money.

My— after my— I had— when I left—

so I ended up living in Boston for a year and a half after I got kicked out because I got 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'd you get kicked out for?

I just didn't go to school.

I literally didn't go to school.

Like, as soon as I— 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 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— I don't wanna 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, it becomes this idea that like you've replaced 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.

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 2 days, or I knew something was up.

I always knew when she was high, always knew when she was on drugs.

It all of a sudden hit me like 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, 1996, '95, but no one was using that language.

But 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 gonna die, honestly, straight up.

And I was like, 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 gonna 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, 'cause 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, it's just awesome.

And then I remember at the end of my sophomore year, I was booking.

I was dating this girl.

I was out every night.

I was having anxiety attacks like it was like a cold.

Like, wasn't even thinking about it.

How did they manifest for you?

Like, what's it look like?

Like, my heart would race.

My left arm would go numb.

Just weird shit physically.

Do you still suffer from it?

Do you have anxiety now?

Mm, yes and no.

Like, they don't happen in the form of an anxiety attack anymore, no.

And 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 gonna 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 calmed or I had time to think about something, your mind can kind of bug you out.

I remember I was sitting in my apartment and I called my brother and I'm like, I gotta 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.

I'm interested just— but 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 Yeah.

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 like 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." Um, it was like— Knowing how much was bet on one side and figuring out if I had to lay off my bets.

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.

And it was like the first thing I felt real pride in that I had like 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 loved that movie and loved 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 with anxiety.

So you decide, you're like, I've gotta 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 gotta 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, you know?

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 5 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, like, I gotta do, like, I gotta do something.

Like, I miss the booking side of my life a little bit.

You missed the money?

I missed the money.

Or just like feeling like I'm 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 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, 2 years in.

But at that point— You lost all your P&L discipline.

P&L discipline was gone.

Out 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 and I know how I— like, how I can, like, be successful and powerful.

And I gotta start this journey.

And was that— that was, like, the music business?

Like, I'm gonna 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 De Niro.

Just me hustling in New York.

Pretty good.

And I'm 19 or 20.

Sounds like something.

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.

OK.

For being in a room and being comfortable talking to anybody.

And I knew I had a taste, and I knew I understood, like, how to get people to talk about something.

Like, how to get people to— to react to something.

I understood that.

And as soon as that finished— and life has, like, been this, like, constant, like, 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 Patricoff, called me and he said he wanted 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, like, 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.

Oh yeah, that, that'll get you.

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Do you think that, like, perhaps not having much guidance in your life made you fearless?

'Cause that's a pretty, like, crazy role to step into with a friend without you knowing anything or what to do.

No blueprint, no game plan, no rule book, no guardrails, and— Were you scared?

No.

No?

No.

No, never.

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 just to hang out the window waiting for my mom when she wasn't home.

I was scared about that shit all the time.

Yeah, it was normal.

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, like, more of a runway 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 see Good Will 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 did that, 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 2 or 3 people that I knew had started in the music business.

And 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.

And next thing I knew, like, I found myself 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 seen 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.

'Cause it feels like you've done that over and over and over again.

Yeah, it was— 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— 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 let me respect these people in a different way.

Totally.

And I never really asked for shit.

Like, that's not how I approach relationships.

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.

I mean, you can't be that guy, you know?

So it was really just about forming these relationships and finding my little niches of ways to fit in, you know?

And my little pockets where I could

create value.

But the thing was, is I always knew I was gonna be so much bigger than what I was doing.

But I was okay with, like, sitting in that role at that time.

I understand that so much.

I wonder, like, when you were in these rooms, in these very powerful rooms, like, if any of your sort of insecurities, like, would bubble up.

Like, I just like 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 gonna 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, I mean, it's incredibly— 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

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.

1 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.

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

like I, 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 would 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 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 realize now was that like, not sure

if that wasn't just I think that's 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.

You know, it was just so much.

It's just so much.

Do you mind me asking what's the relationship with your mother now?

Like, where did you get to with her?

And did she recover?

Yeah.

So it's really— it's really sad because, you know, my mom went like this.

So 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.

Wasn't always there mentally.

And the last, like, 8, 9 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 aide for her.

Her mind kept going.

And then about 5, 6 months ago, or maybe a little longer, I ended up finding her in her apartment.

And then 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 it was the most docile that I had ever seen her ever in my life.

She was sweet.

She was like a child.

And the conversations weren't that real, but there was one or two songs we used to listen to together and 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?

Mm.

I'm just getting it now.

What happened was, is I— They called me from the nursing home.

They told me that, you know, she had stopped reacting to the stimuli or whatever, stimulation.

So that meant she was gonna pass soon.

So I said, "Can I come tonight?" You know?

And they were like, "Yeah, you'll be fine." And 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.

And 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 talked 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 inside, 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 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 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,

I didn't need to get that deep.

No, it's just, it's one of those things I think that, um,

first of all, I was not expecting you to say that at all.

Sorry, I was expecting to be like, yes, I fully got closure, 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,

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 gonna look back in years to come and be so happy that you had that moment.

Yeah, I feel that way.

No doubt.

I feel that way.

No doubt.

And I really— I actually—

I'm gonna call you in a couple of months and figure out what you did with those ashes.

Yeah, for sure.

What do you think, because you have two kids— Yeah.

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?

Um,

absolute love and support at, um, any cost and no matter what.

Um, 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 dealing with.

I'm 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 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 It's like, there's

your kid 12 years ago in one second.

You die.

And I remember I have such an 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, goddamn.

That was

like 75 of them.

So you're like, so you don't want one from my next place?

You 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 and every phase.

No, and here's the thing.

It's like you eclipsed 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.

And so I really believe that what you've done, not just becoming successful, but having this incredibly successful family when you had had absolutely no basis, no example of that.

Like, 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 that— how you move through the world when that's your starting point is something I, I will always be mad jealous of.

So good for you for being an amazing, amazing father.

I tell you the good was is I've been able to really establish that with my father the last, like, few decades of my life, especially when my kids were born.

And, you know, 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 'cause 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— I knew he loved me always, so like, And knowing that is really like sometimes with your father all you really need.

But our relationship is so strong right now.

And, you know, he's one of those rare people that,

you know, has this like understanding of taste and curation and style.

You 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 realise what you got from your parents.

Yeah.

Like it or loathe it, you know?

Yeah.

I think about it all the time.

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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 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 wanna 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 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, 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.

I 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 gonna build something insane.

But you know, Marc needed to build Marc 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.

Like 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 Roc 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.

And, 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 the glory days, right?

Like, I remember Roc Nation wasn't just like, you know, another label.

It was— It was like Roc Nation, Jay-Z, J.

Brown, Tay Tay.

Like, it was such a thing.

Just to be around and in those guys' orbit was a big deal.

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 was challenged, and I thought I knew what hard work was.

And I thought I understood, you know,

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.

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.

That 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 that had, like, 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.

Your 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— 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, I functioned.

I got married young.

I was operating at a very high level in some in regard.

But I had such big dreams for myself.