The Change Agent: From Street Corner to the Corner Office (Steve Stout)

If you’ve ever felt like where you come from holds you back — or that success only happens for people with access — this conversation will change how you see yourself. Music mogul, entrepreneur and branding genius Steve Stoute joins Emma to reveal how he turned being underestimated into his advantage, using his roots, instincts, and connection to culture to build an empire that reshaped music, marketing, and business. You’ll learn how to: -Turn rejection into momentum -Use your background as your competitive edge -Build ideas that move culture — not just chase it Watch this if you’re ready to stop waiting for permission and start turning your story into your strategy.

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:10Emma Grede?

  Some people wait to be invited into the room. Well, Steve Stout has never waited for anyone. Steve is a powerhouse music executive, marketing genius, CEO and founder who has worked with everyone from Jay-Z to big global brands. But it all started with one truth: your background isn't baggage. It's the key to unlock everything you've been chasing. What I love about Steve is that he never tried to fit in. He used what he knew and where he came from to his advantage. He's helped artists sell millions of records, built culture-defining companies, changed how brands talk to culture, and now he's here to show you how to achieve breakthrough success by leaning into exactly who you are.

• 0:55Emma Grede?

  I'm so happy to have you here. Just to contextualise it a bit for the audience, I want to understand what your core skill is. When you think about all the success that you've had, what do you ultimately boil it all down to?

• 1:08Speaker 01

  I was always curious about things I didn't know and understand. I never let industries that would knew intimidate me. So the truth was that what I seen growing up as a kid in Queens, Trinidadian immigrants, was that everything that we were doing, everything that I seen happening over time would then somehow have this reverb effect and then get larger and larger and larger. And the only way to capitalise on that was to figure out how to get into those industries and get into those rooms in which you could make that big step change. But what took place was no one was able to get in those rooms.

• 1:53Speaker 01

  First, there was the first big obstacle, there were white people, white corporate CEOs, and they didn't give a shit about what you had to say. So how are you going to get in that room? So building relationships became a thing that you had to do. Because you had to figure out a way to get those people to understand your perspective. So you were forced to do things. And I'm talking about 20 years ago, not when it's in vogue today. Because there's money behind the movement. So of course, you're gonna get the cool white CEO who wants to know the cool young black person or Spanish, Latina, whatever it may be. I'm talking about when they were doing well on their own. And you had to go in there and get them to truly understand.

• 2:35Speaker 01

  I know you're doing well, but you would do even better if you did this. That was a very hard thing to do back then. So you learned relationship skills as a result of it because you had to get into that room. So I would say that understanding and confident that I knew something that others didn't. And then putting relationship skills on top of it was the key difference for me. I know a lot of people who knew that we had something different. But they didn't have the relationship skills. So they would just end up arguing all the time. Like, you don't understand. And I didn't want to ever be that person who was sitting at a bar fucked up financially, saying, you know, I had that idea first.

• 3:19Speaker 01

  I know what that looks like. That person who had the idea, but because they could never convert that idea because they didn't take the relationship part or the relatability part or trying to figure out a way to bridge the gap more serious. They got so caught up in their idea that it frustrated the shit out of them and kept them trapped. So the combination of understanding those two skill sets at a very young age, I would say, is what I did different.

• 3:50Emma Grede?

  And I guess there must have been a time when you were frustrated and you felt trapped. Like, was there ever a moment where you were frustrated by the start you had, where you come from, the fact that it wasn't a given for you? How did you get past that? Because I think so many people feel like that.

• 4:07Speaker 01

  I swear to you, Emma, I never felt trapped by that. I actually would tell you I feel more trapped now when we can talk about that. I never felt trapped back then. First of all, when you talk about... African American culture, or even, let's talk about hip hop culture, black people in America ascending, was coming up during my time. You got to think about, you know, whether it be Living Single, or The Martin Show, or Will Smith, and hip hop, everything's going at the exact same time. And it's coming from ground zero. It's moving really fast. Every time you had any sense of doubt, you didn't have to look too far to see something moving in the right direction. Yes. That, that looked like you and felt like you. And that was very important as

• 4:52Speaker 01

  a reminder that you were on the right step and in the right path. So it wasn't frustrating. Again, it could have been frustrating if I didn't open myself up to knowing, now I got to get to the relationships, now I got to be able to get to the other side. All of the guys that were successful before me, whether it be the late, great Clarence Avant, or Quincy Jones, or Benny Medina, all of those guys that were successful and understood black culture, always had a counterpart, a Jewish counterpart, for the most part, who understood them and was their partner, was almost like their segue into a larger

• 5:33Speaker 01

  financial opportunity, distribution, capitalization, those types of things that could help you do something. Mm hmm. So, all I had to do was like, what did those guys have? And there's a lot more of them. What did they have? And in my early relationships, Jimmy Iovine, Tommy Mottola, Peter Arnell, in advertising, they were guys that I found along the way that helped me go further in my career. And you could, you could look at my career and you could see the, who those people are. It's not like hard to tell. Did, did you study those guys before you knew them? No. No. Study them? No. Because I do that. I do that all the time. I find out who's the tip of the top. They had, they had good jobs. Let me, here goes the study. Yeah.

• 6:16Speaker 01

  Who's the CEO of Sony Music? Oh, that's Tommy Mottola. Oh, who's the CEO of Vintoscope? Oh, that's Jimmy Iovine. You know. You knew them? How I got to know them is a separate thing. Okay. But I didn't have to study them. The title and everything was right there. And it wasn't like a lot. It wasn't, it wasn't like fractured information like it is today, where there's a thousand different options. There was five labels. Five guys. And you got to call one of five guys. So, am I good enough to beat everybody else at getting to one of those five guys? Yes. Yes, that's easy. No, so there was nothing to study.

• 6:49Emma Grede?

  I love that there's nothing to study. The New York Times calls you the CEO that other CEOs turn to for advice. And I wonder, does that even mean anything to you when you see a headline like that?

• 6:59Speaker 01

  That's a fucking great question. Why'd you ask me that?

• 7:02Emma Grede?

  Well, you know, I asked you because I think like there's such a part of you that is there's so much self assurance in you, right? You're like, no, I didn't study the guys. I'm like, I'm studying everything. I still feel like I'm studying to this day. So I I wonder if there is anything in you that goes, yeah, I love that. I love that adulation. I love to see headlines written about me like that. Or is that just another headline?

• 7:24Speaker 01

  I was shocked that the writer got away with writing that headline. I was, I I couldn't believe that they, that was the headline, actually. Let me be honest with you. There's truth to that. Obviously, it's what I do for a living. It's what I've built a great living doing. But when I first read the headline, I was taken back by it, that the writer in the New York Times would write that as a headline. To be honest with you, that was my first take on it.

• 7:49Emma Grede?

  What were you, were you, um, do you feel embarrassed or what was the feeling? I want to understand that.

• 7:53Speaker 01

  That's a bold headline. That's a bold headline.

• 7:57Emma Grede?

  Yeah, but it is the truth. I mean, it's New York Times. It's a proper journalist. It's not some like, you know, random.

• 8:01Speaker 01

  So then, I mean, I'm trying to be humble about it. I'm just, no, I wasn't surprised.

• 8:06Emma Grede?

  Good luck. Might be the first time in this interview or the last time in this interview.

• 8:09Speaker 01

  No, I wasn't surprised. And they got the picture right, too. Um, the whole thing worked.

• 8:15Emma Grede?

  It was, first of all, it was a great article, but it was very accurate.

• 8:17Speaker 01

  I was very proud of it.

• 8:18Emma Grede?

  It was a great summary, I think, of your career. And, you know, when I think about you, I I really want to understand. I mean, I know where you came from, but I'm trying to understand like the essence of you, the early experiences that shaped your understanding of the culture. Like, can you talk to me a little bit about what has made you so successful and that understanding of culture? Like, where does that come from?

• 8:43Speaker 01

  I got a chance, growing up in Queens, then nineteen eighty six, to see. You would love this. I mean, I have vivid memories, not blurry at all, vivid of watching LL Cool J perform at block parties. I mean, watching a guy that looked just like that with the can go on, perform at a block party that you paid 25 cents to get in. I seen LL Cool J battle guys in the mall. Like, when you look at kids in the mall in a circle. How old were you at this point? I seen him at 16. Like, I seen that, okay? I seen Run D- when rap took off, and specifically in my neighborhood,

• 9:28Speaker 01

  the guys, they were big names and they had music videos, but they still lived in the neighborhood. They didn't make enough money to move. So they got the jewelry, the clothes, and the car, but still live. They're right there. Right there. So you got a chance to see it and feel it and be around it. That was very important. I mean, obviously, you wish that they made more money to ascend and go further, and they should have got what they deserved earlier. But you also got a chance to feel it and know, oh shit, this could be you. So the success of those things and watching those things ascend were very important to me in shaping my perspective on this thing could really be big. Bismarcky performing in basements at a basement party.

• 10:13Speaker 01

  These are like real, real things that I seen and witnessed. And growing up in that neighborhood, within a five mile radius of where I live, is Tribe Called Quest, Russell Simmons, Run DMC, LL Cool J. They all lived in this neighborhood. You know, I would go out to Long Island and you'd see EPMD at the mall or the Fat Boys, Salt and Pepper. These were all real things within one. Area, but I mean, honestly, within one area. So I just, it's like when people grow up in Silicon Valley and they understand tech. Obviously, they're within an area in which there's nothing but tech entrepreneurs and visionaries of that idea there.

• 10:55Emma Grede?

  Mm hmm.

• 10:57Speaker 01

  In my neighborhood, I happen to be in a place in which hip hop reigned supreme and everything around it, the breakdancing, the streetwear, obviously, the music and the production and the whole thing. It shaped me. It gave me perspective on the power of culture. Now, I'm not saying that to say that I knew it would be a business and I don't want anyone looking at this to say, oh, look how fortunate he was. He grew up there, so he knew it was going to be a business. I didn't know it was going to be a business. I'm just saying it was in my DNA. So then, when ultimately the opportunity came and I was like, oh shit, I could put these two things together. If you fast forward to like, oh shit, you can make a G unit sneaker, you can make a Jay-Z sneaker.

• 11:41Speaker 01

  When it got to that stuff later, then I started to pull from those things. I didn't know that at the time.

• 11:47Emma Grede?

  So you were really destined for a career in music. You were, I think, an extremely, no? What do you mean, no?

• 11:53Speaker 01

  I thought that I was going to play sports, football. I, I, I thought I was going to make money in real estate. I was doing well in real estate. I invested the money in real estate to get into music. But again, I didn't know that was going to be the whole thing.

• 12:07Emma Grede?

  Where'd you get the money from to invest?

• 12:08Speaker 01

  In real, in real estate. My mom let me, you know, my mother let me money. She refinanced a house.

• 12:15Emma Grede?

  Oh, my goodness.

• 12:16Speaker 01

  And, and, uh, I mean, she refinanced a house. My father was away and he definitely didn't know she refinanced the house. And I'm never going to ask her how she got his signature.

• 12:28Speaker 01

  And she refinanced the house and lent me money.

• 12:31Emma Grede?

  She must have had a lot of faith in you.

• 12:32Speaker 01

  And she took the money and I took the money and I bought a property and I ended up making money on that property shortly and that gave me, that was the seed money to get me going.

• 12:41Emma Grede?

  Do you remember how much you made?

• 12:43Speaker 01

  Yeah, I made forty five thousand dollars.

• 12:45Emma Grede?

  Oh, that's a lot of money back then.

• 12:46Speaker 01

  Yeah, I made forty five thousand dollars when I was nineteen.

• 12:49Emma Grede?

  And you paid your mom back.

• 12:50Speaker 01

  I paid my mom back and and I got going.

• 12:53Emma Grede?

  But for you, that was that was like a moment in time, right? How many years were you doing this with with homes?

• 12:59Speaker 01

  I was probably doing the mortgages for like three years, three and a three and four years. And I took the money and I started investing and I found a producer and that producer. And I started a company and we were trying to make tracks and shop our music. And the first real opportunity I had, there was a young, talented comedian, who we developed a friendship early and he was shooting a pilot and gave me the opportunity. And anyhow, long story short, it was Martin Lawrence. And the first thing that I was credited for doing was the Martin Lawrence theme song for his television show.

• 13:36Emma Grede?

  I want to talk to you about this kind of turning point in your career. So you've obviously you grew up in Queens. You play some football. I'm making a very, very short story now. You you get into real estate. And let's just fast forward because the things that people say about you, Steve, it's so crazy. I mean, I could sit here and just like blow up your head.

• 13:57Speaker 01

  Tell me.

• 13:57Emma Grede?

  People, I mean, first of all, I mean, Jay-Z describes you as the bridge. He says you're the bridge, the voice between hip hop and business. What does that mean in practice? Like, what do you actually do? How did you get that reputation?

• 14:10Speaker 01

  Well, he was talking about what I was talking about earlier, like being able to develop relationships. When I was doing what I was doing, honestly, like, yes, I watched the Benny Medina's and the Quincy Jones and the God bless the, you know, Clarence Avon's and and so many more. Build these relationships in corporate America, specifically in entertainment. I wanted to do it outside of entertainment as well. So when I went into advertising, whoa, now I'm trying to take hip hop culture and I'm trying to bring it to brands and they don't even need this shit. They don't even need this shit and they thinking it's. Guns and violence and problems.

• 14:54Speaker 01

  Trying to convince somebody to do something when they don't need it is extremely difficult. Like if you need it, then it's like, okay, fine. Like shit ain't working, so let's try this. But you gotta remember, back at that time, when we're trying to sell Jay-Z sneakers or trying to, which is probably what he was referencing, but I also had so many big ideas and have so many big ideas that the brand is thinking, we don't really need, it's not like we need to use this thing to solve a problem. So why are we even engaging in the unknown? But my idea was, let me, then I'm gonna take the time to develop a relationship with you. Let me translate this for you. So that you actually can see how this can be accretive to what your intentions are as well. This is not an alternative.

• 15:39Speaker 01

  This is actually something that works in accord with what you're currently doing. And that was hard, to learn the language, to learn the cadence, to learn what would work best. And a lot of times for me, the best way in is was if that person had a teenager at home. Cause if they had a teenager at home, if the CEO had a teenager at home, I had a shot. Because they would ask their child one thing. And if it came back right, then I'd get the return phone call.

• 16:10Emma Grede?

  Yeah. That's so true. I totally understand that so much. What was the infliction point, do you think, where culture and business really clicked for you?

• 16:21Speaker 01

  The easiest way to market would be Men in Black. And Men in Black was interesting from a standpoint that, you know, Will Smith's career as a musician had come to a, you know, head tough times. And I'd known Will for years because I worked with Kid N Play and Will Smith. And those were like the happy rappers.

• 16:45Emma Grede?

  Yeah.

• 16:45Speaker 01

  Right? So like.

• 16:46Emma Grede?

  Different vibe from where you came from, maybe?

• 16:49Speaker 01

  So Kid N Play and Will Smith were the happy rappers. They were successful.

• 16:52Emma Grede?

  And acceptable, right? To the wider culture.

• 16:54Speaker 01

  They had movies, they had television shows. They were happy rappers. And the reason why they had television shows and movies is because they were safe.

• 17:02Emma Grede?

  Were they happy being happy rappers, by the way?

• 17:05Speaker 01

  No.

• 17:06Emma Grede?

  No.

• 17:06Speaker 01

  You know what the funniest thing was? They both wanted to be the opposite. Yeah.

• 17:10Emma Grede?

  Of course.

• 17:11Speaker 01

  They all wanted to be the other shit.

• 17:12Emma Grede?

  Dark.

• 17:13Speaker 01

  All the other guys are looking at, because back then that was selling out, right? Being successful and selling out were closely assimilated. Like, oh, they're selling out. Look how successful they are. That's such a trash idea in hindsight, but it was a trash idea the entire time. So when Will Smith had hit, you know, headwinds as an artist, there's DMX and Biggie and Nas and Wu-Tang and all this set. And now he wants to come back or put out music. I knew his team. I knew him and they entrusted me. I was at Sony and we made the soundtrack for Men in Black. And Will Smith was so ice cold at that time. You think he's cold now? He was freezing back then.

• 17:55Emma Grede?

  Oh, he's cold now.

• 17:56Speaker 01

  He's cold. But he was so cold back then that on the hook for Men in Black is SWV. And they didn't even want to be in the video.

• 18:04Emma Grede?

  No, that's so crazy to think about because I feel like that was like the heyday of Will.

• 18:10Speaker 01

  They didn't want to even be in the music video.

• 18:13Emma Grede?

  Yeah, I mean.

• 18:13Speaker 01

  His happiness and their credibility, they didn't want that to mix. So they wanted the chat, but they didn't want the video.

• 18:21Emma Grede?

  So what, so what does the unhappy happy rapper do with himself?

• 18:25Speaker 01

  When he gets successful?

• 18:26Emma Grede?

  Yeah.

• 18:27Speaker 01

  Oh, well, when the song becomes successful, Will goes on a run, right? Then we make out, then he gets jiggy with it, right? Like everybody would do. When you're happy, you get jiggy with it. Wouldn't you do that? So anyhow, that's funny. The, the glasses that he wore in the movie, in the music videos took off. And when that moment took place, we at the record company was so successful because we sold 10 million Will Smith albums. And we didn't expect that to happen, obviously.

• 19:02Emma Grede?

  Fair.

• 19:04Speaker 01

  And revive his career and have massive success. And I thank him for that. But I was interested in those glasses, man. I'm like. We're not eating, eating up the glasses.

• 19:15Emma Grede?

  Hmm.

• 19:15Speaker 01

  How could be, and you know what's funny?

• 19:17Emma Grede?

  And you weren't, you weren't getting paid off the glasses?

• 19:19Speaker 01

  No.

• 19:19Emma Grede?

  No, the glasses were just in the movie, no one's getting paid.

• 19:22Speaker 01

  How about this?

• 19:22Emma Grede?

  What about Will?

• 19:23Speaker 01

  How about, Will got nothing. They were promoting, it was promotion. They paid the movie company something and the movie company.

• 19:28Emma Grede?

  Product placement, babyface, yeah. Nah.

• 19:32Speaker 01

  So what happens is, the whole thing takes off. And that honestly got me down the path of trying to figure out who did the product placement? Who was the agency? I got close to the agency and I ended up leaving the music business and going to work that agency.

• 19:49Emma Grede?

  So you then start translation, the agency.

• 19:51Speaker 01

  Yeah.

• 19:52Emma Grede?

  How do you go round to all of these artists and convince them that they need to then start thinking about themselves as a brand? Cause it's early days for that.

• 20:01Speaker 01

  It's early, you know what? And every, there's, you can't watch a podcast without Jay-Z's name coming up anymore.

• 20:08Emma Grede?

  Hmm.

• 20:09Speaker 01

  But.

• 20:09Emma Grede?

  Let's do it, come on, let's talk about Jay.

• 20:11Speaker 01

  But he, he was all in. He believed, he believed in me easily. Like, he did it, he was wearing Nikes and then left and did like his own pair of Reeboks. And Reeboks were being shitted on. I mean, Biggie, Biggie wrote a line, "You were a Reebok vando. Now you wear Chanel sandals. I made you. Why would I play you?" I mean, he wrote those a lot. I mean, they were like, considered the worst.

• 20:38Emma Grede?

  Yeah.

• 20:39Speaker 01

  And Jay said, "Nah, we gonna put S. Carter on these joints and we gonna go." And now listen.

• 20:43Emma Grede?

  Because he was getting a piece of that.

• 20:44Speaker 01

  Yeah, but, but he believed in himself. Fuck what Biggie said about the Reebok Vandals and fuck whatever, I'm gonna change your opinion on these joints.

• 20:53Emma Grede?

  And he did.

• 20:53Speaker 01

  And he did.

• 20:54Emma Grede?

  And he did, cause they were all, everyone was wearing them.

• 20:56Speaker 01

  That's the reason, that's what led to Yeezys. That's how.

• 20:59Emma Grede?

  Yeah, that was the deal that changed the game.

• 21:01Speaker 01

  That's how the, Reebok got sold to Adidas. This is why the Yeezys got made. I know the whole story. Like, Pharrell would tell you, Pharrell won the CFDA award and said, it was, "I gotta thank Steve Stout, I put Pharrell in the thing, with ice creams." That's what him and Nego did the joint. We made ice cream sneakers. This is in 2004. This is crazy shit.

• 21:23Emma Grede?

  Early, it's early.

• 21:24Speaker 01

  Come on, man.

• 21:25Emma Grede?

  Well, that's what I'm saying. That's what I mean, I literally have followed your career.

• 21:27Speaker 01

  You were the one. I'm saying that.

• 21:29Emma Grede?

  But you are credited for that. I feel like that.

• 21:30Speaker 01

  I'm not, I'm not saying it because I'm not credited for it. I'm not saying it, there's nothing I'm saying that I'm saying in this conversation for credit. I'm saying it because I want people to unpack the DNA of what an idea is. To feel comfortable breaking new ground. We have so much more to give if you can find the tension between what is culturally happening and what problem you can solve as a result of it. And there's so many more categories that could use our insight. And some of them, we feel like, oh, we can't do that because the barrier entry is too high. How are we going to get into shapewear? Or how are we going to get into like, oh, alcohol is taken. But I remember there was a time when there was no way you could get into alcohol. Alcohol, are you crazy?

• 22:15Emma Grede?

  A million percent, or soft drinks, you know.

• 22:17Speaker 01

  Alcohol, soft drinks, clothing.

• 22:20Emma Grede?

  We were like Diageo on it, Coca-Cola on it, Puerto Rico on it, we can't do that.

• 22:24Speaker 01

  So many different categories that we can actually go into and use our unique insight and bring ideas to the table. So I'm not saying this for any other reason, but I had those ideas back then. And there are young people that should have those ideas now. Or people who are looking to break through in culture have those ideas now. But the, the most important thing is, are you an entrepreneur? And, and we should talk about that at some point.

• 22:52Emma Grede?

  I want to talk about it right now. What do you, so how do people tell? Because let's be honest, right? I feel like where we are in the culture right now, everyone wants to be an entrepreneur. A lot of people think they can start businesses. I have an amazing.

• 23:04Speaker 01

  Everyone can start a business.

• 23:05Emma Grede?

  Everybody thinks they can.

• 23:07Speaker 01

  No, no, no, no, no, no, let me tell you the truth. You're wrong about that.

• 23:11Emma Grede?

  Go on, tell me.

• 23:11Speaker 01

  Everyone can start a business.

• 23:13Emma Grede?

  Well, they can start one.

• 23:14Speaker 01

  Well, that's all I'm talking about.

• 23:16Emma Grede?

  Go on, keep going.

• 23:18Speaker 01

  That's, no, that's the end of the sentence.

• 23:19Emma Grede?

  That's it. You're just, everyone can start one.

• 23:21Speaker 01

  Period.

• 23:22Emma Grede?

  So what does it take?

• 23:32Emma Grede?

  What is the difference between those that should and can start businesses, those that should and can perhaps take jobs? And how do people decipher that for themselves? Because I think that what you're talking to here is a lot of people that are ambitious. So how do you decide how to place that ambition? How do you know what type of person you are and where you should put your energies? Your ambitious energy?

• 23:56Speaker 01

  One of those things that I think is very important, I don't want one to feel like you can make a lot of money. You can do very well. Working at a company.

• 24:11Emma Grede?

  In this country? Yes.

• 24:13Speaker 01

  And not having the risk of getting fucked up, being broke. Make a good living, secure your family and do well. And there's nothing wrong with that. And that shouldn't be looked at as negative. And that shouldn't be looked at because you're not an entrepreneur. You did this thing that's less than. That's not true. Most entrepreneurs fail. Most entrepreneurs are fucked up. If you speak to Travis Kalanick, Travis Kalanick, the guy who started Uber, failed and was back at his mom's house at 33 years old. As a failed entrepreneur before he started Uber. He started Uber waiting for a taxi that didn't show up.

• 24:59Speaker 01

  That was like fuck off. They probably thought he was a failure and they didn't want to stop.

• 25:05Speaker 01

  But Travis will tell you that story. You gotta be willing to do that, to be that fucked up. And you have to have a belief in yourself that's so maniacal that people think you're crazy, people ridicule you, they think you're bugging the fuck out. You know, you're willing to put it all on the line. And I can't tell you that unless you have a dream in your head that you can't get out of your head, that it's worth it.

• 25:33Speaker 01

  Unless you have something in your head, that unless you pursue that thing, it won't get out of your head, I'm not sure it's worth it.

• 25:40Emma Grede?

  I love that framing. That's really important. Unless you've got something in your head that you otherwise can't get out of your head, it might not be worth it.

• 25:48Speaker 01

  It might not be worth it.

• 25:49Emma Grede?

  That means that you are constantly thinking about something.

• 25:52Speaker 01

  You have no choice.

• 25:53Emma Grede?

  You don't have a choice.

• 25:54Speaker 01

  You have no choice.

• 25:56Emma Grede?

  Because the rate of failure is high.

• 25:58Speaker 01

  The rate of failure, it doesn't make any sense. The math doesn't work.

• 26:03Speaker 01

  The math doesn't work about being a successful entrepreneur and getting funded and growing and having a successful exit. It doesn't work. But if you can't get it out of your head, I understand. I couldn't get it out of my head. I didn't, I didn't know. I know I couldn't go to college. I know I didn't want to do that.

• 26:21Emma Grede?

  Well, you tried and you tried and you tried.

• 26:22Speaker 01

  I tried and I tried. And I wanted to make my parents happy. I knew I wanted to do that.

• 26:25Emma Grede?

  Is that, is that what the driver was to try so many times?

• 26:28Speaker 01

  You're a West Indian parent, you're a West Indian man. You gotta like, gotta, you got, definitely gotta go to college.

• 26:33Emma Grede?

  Your parents got all the way here and you can't even make it to college.

• 26:37Speaker 01

  So I didn't want to let my parents down. So I let my parents down when I didn't go to college. But I didn't know I wanted to be an entrepreneur. That word has started to get hot in the last 10, 15 years. I didn't know, the two words that got hot in the last 15 years, well, there's three words. One is entrepreneur. The other one is mentor. Right? The fact that people run around asking people to be their mentor is insane to me.

• 27:04Emma Grede?

  Okay, just, just pause there.

• 27:06Speaker 01

  Why?

• 27:06Emma Grede?

  Wait a minute, we're coming back, we're coming back.

• 27:08Speaker 01

  We don't have a commercial break.

• 27:09Emma Grede?

  Entrepreneur, we're coming back. Entrepreneur, mentor, what's the other word?

• 27:14Speaker 01

  Culture.

• 27:15Emma Grede?

  Culture. Okay. We're coming back. Go back to the mentor bit. Why is it crazy that people run around asking for a mentor?

• 27:21Speaker 01

  Why are you skipping? Why do you want to go to that one?

• 27:23Emma Grede?

  So I just want you to get in trouble. I'm gonna ask you about work-life balance in a minute, so get ready. And tell me, why is it crazy that people run around asking, will you be my mentor?

• 27:32Speaker 01

  Because I never heard of that shit before. Somebody chose you. Somebody found something in you and decided.

• 27:40Speaker 01

  Without saying it publicly, that they were gonna take you under their wing. And then all of a sudden, there was this transition that you were being mentored by them. There was not a transaction that said, can you be my mentor?

• 27:56Emma Grede?

  Yes.

• 27:57Speaker 01

  Yes. I am your mentor.

• 28:00Emma Grede?

  You are anointed, yes.

• 28:02Speaker 01

  I don't know what the fuck anyone's talking about. And when people say it, I'm like, what part of TikTok did I miss this one?

• 28:09Emma Grede?

  But tell me, you know why people are looking for mentors? So what do you tell them? I have a pretty, like, my thing is, don't ask for a mentor. Ask for questions. Don't come and ask me. If you've got my time and I'm in front of you, ask me a fucking question.

• 28:21Speaker 01

  Can you be my mentor, please?

• 28:23Emma Grede?

  I have a good time. So what do you tell people that are looking for a mentor?

• 28:26Speaker 01

  When people ask, if somebody's looking for a mentor, I try to tell them this thing. Like, obviously, you want to be in proximity of success and people that you want to emulate. Right? I talked about this a long time ago. If you find somebody that you are, that is successful, emulate them and don't find any shame in that. There are people who are in this industry right now who emulate me. And it doesn't bother me. It bothers me if they don't give me credit for that.

• 28:54Emma Grede?

  Quite right.

• 28:54Speaker 01

  Or at least acknowledgement of such. But, but I do encourage, regardless of that feeling, that you emulate that person. It doesn't matter because whatever makes you successful, wherever you can find it, borrow from it.

• 29:07Emma Grede?

  Yes. That's why I asked you if you studied those guys, because I feel like when you, when you grow up, how I grew up.

• 29:13Speaker 01

  I studied Quincy Clarence.

• 29:15Emma Grede?

  Of course you did.

• 29:15Speaker 01

  I studied Quincy.

• 29:16Emma Grede?

  Because you wanted one generation before.

• 29:18Speaker 01

  I thought you were asking me, was I studying the guys?

• 29:20Emma Grede?

  Jimmy and, fair, fair, fair. But you did study Clarence, you did study Quincy, you did, like, you, you were there looking at those guys, looking at their behaviors, looking at their, how they moved, and, and you were like.

• 29:31Speaker 01

  Yeah, I was studying Russell Simmons, Clarence Avant, Quincy Jones. There was a guy who started, who took over Beatrice Foods, Louis, he happened to pass away, Reginald Lewis, I believe his name was. He wrote a book, Why Do White Guys Have All The Fun? You should definitely read that book. He was like the first black guy in, that was doing it gigantically on Wall Street. But I would read about these guys, these gentlemen, and I would be constantly.

• 29:58Speaker 01

  Inspired by what they were doing, and even like, like Russell Simmons back in the day, is you pull it from everywhere and, and I don't get, some of it is shallow and I don't care about that. Russell Simmons had a Cartier Panther on and he's sitting on.

• 30:11Emma Grede?

  A Panther, interesting choice.

• 30:14Speaker 01

  He's sitting, uh, he's sitting on a Rolls Royce and he takes the picture. And I'm looking at that photo and I'm like, okay, the fact that he got that watch on, that Cartier joint on and that Rolls Royce in the hood, I like that. At the same time, I like Mr. Lewis and what he's doing with Bitch's Foods on Wall Street. At the same time, I love what Clarence is doing between the business deals he's brokering for Jimmy Jam and Terry Lewis and LA and Babyface.

• 30:44Emma Grede?

  But it's like self mentoring. You're looking at these people and taking it.

• 30:48Speaker 01

  All these people, the constellation of it, I'm pulling from all these different places. And then over time, I have met people and they have mentored me. I would tell you that Jimmy Iovine has been my mentor. He's given me years and still, and still provides me advice. I've learned from other people. Jimmy Iovine has been my mentor. I didn't ask for that. I didn't know that we were doing that. I didn't realize that dance was happening until 10 years after the dance. Like shit, every time I think of something, I'm in a jam, I think about what Jimmy said. You know, that kind of thing. But this idea that you can walk up to somebody and be like, can you be my mentor?

• 31:30Speaker 01

  It's so fucking fake. Like you can't just microwave a fucking mentor, man. There's no, it's not like a popcorn button. Like these people are so crazy with this bullshit.

• 31:40Emma Grede?

  He said, you can't just microwave a mentor. I do think that's really important takeaway. Because we have become as a culture obsessed with the idea of mentorship. And you're right, you can't manufacture those relationships, they are or they ain't.

• 31:52Speaker 01

  Me like, what are you talking about, man? You need to shut up and listen to what I'm saying about.

• 31:57Emma Grede?

  Well, that's why I've got you here because you've got so many good things to say. I know you're not talking to me, Steve. I know. You've got to tell me to shut up on my own podcast later, maybe. Um, I want to talk to you just about this again. You just talk about culture a lot. Why do you think it's like, talk to me about why it's something that is a buzzword and that you're like, it feels to me like you feel like the word is like overused or misused. Is that what you're saying?

• 32:22Speaker 01

  Yeah, because what happened is it's turned into this ketchup. You could put it on anything like, not on a culture, culture, culture. And sometimes it's specifically meant to talk about black culture. I wrote a book, The Tanning of America.

• 32:40Emma Grede?

  I read it.

• 32:42Speaker 01

  You told me that.

• 32:42Emma Grede?

  New York Times bestseller. It was fabulous.

• 32:44Speaker 01

  And I wasn't speaking about, when I spoke about the tanning of America, I was talking about a global understanding of culture, something that shared values, something that had commonality, which is what culture is about, is things that lead to culture, like rituals and nomenclature and language. These things are all what shape culture. And the word is just being thrown around now with no true definition by most people. And the intent is to say it in order to say, well, you know what I mean? Like, it's important. And I'm like, that word is so very acute at understanding a group of people and what those people share.

• 33:28Speaker 01

  Don't use that word so loosely and don't use it on anything just because you can't find a better word. Work harder to find, to pick your words more carefully because that word culture has so much depth to it that sometimes when it's used frivolously, it bothers me. Go back to using authentic. Use that word. Remember when you used to play around with that word? Fuck around with that some more.

• 33:56Emma Grede?

  I feel like.

• 33:57Speaker 01

  I got you.

• 33:58Emma Grede?

  Please don't.

• 34:01Speaker 01

  I know.

• 34:03Speaker 01

  He's just in my brain.

• 34:05Emma Grede?

  He's literally in my brain. But I feel like everything that you are so known for is being somebody that intrinsically understands the culture and has been able to, I guess, like decode or code it for brands. Like, that is what you're known for. How do you continue to be that person? What is it that makes you so good at that?

• 34:25Speaker 01

  I'm gonna tell you, the first thing, what I said about my, one of my strengths is. My point of view, my personal point of view is really not important right now. As it relates to what I do professionally. I am a vehicle and a vessel between what is happening and what's needs to happen in corporate America. Okay, so whatever's happening out here, whatever's moving in emerging subculture. I need to understand it and be able to help translate that for Fortune 100 companies.

• 34:58Emma Grede?

  Yes.

• 34:58Speaker 01

  That's my job. Whether I like the dance or like the clothing style or like the word or whatever, it's really not my perspective. In fact, when you would, I built United Masters. It's a music distribution company. We distribute hundreds of thousands of songs. It's not like I like all the songs. There are songs that I really do like. But most of the songs, I can't tell you I have any affinity to. But what I do have an affinity to is helping those independent artists get their music out to the world.

• 35:29Emma Grede?

  Yes.

• 35:30Speaker 01

  Right? And like, that's how I feel about things. You can't, young people are going to shape and define culture. That's what's going to happen. It's happened with my generation. It happened to your generation. It's going to happen with the next generation. We're never going to put Jack back in the box. That's what's going to happen. So trying to fight it like our parents did, like, don't do that and no, no, no, and cut MTV off or whatever the thing was. It's not helpful. So how I remain relevant in this trade, this exchange is by removing myself.

• 36:04Emma Grede?

  Removing your opinion.

• 36:05Speaker 01

  Removing my opinion.

• 36:06Emma Grede?

  So you don't got to like it.

• 36:07Speaker 01

  Facilitate.

• 36:08Emma Grede?

  You just got to understand.

• 36:09Speaker 01

  All I got to do is understand it and facilitate and hire one. That's what I do. I stay, I stay tight to understanding what my role is. As soon as you forget your role and you start thinking it's you.

• 36:23Emma Grede?

  You're in trouble.

• 36:23Speaker 01

  You might as well just close the door, give them back the key and go home.

• 36:28Emma Grede?

  That's a re, that's a really, really precious understanding of what you do.

• 36:33Speaker 01

  For some people, not, it depends on where you are on your cycle of an entrepreneur. Some people, I just said that to me, think I'm bugging. Where you are, you're like, shit, I get what the fuck he's saying.

• 36:44Emma Grede?

  No, I fully get what you're saying.

• 36:45Speaker 01

  That's not for everybody. That's not for everybody.

• 36:54Speaker 02

  Hi, everyone. This is Kara Swisher.

• 36:56Speaker 03

  And I'm Scott Galloway.

• 36:57Speaker 02

  And we want to tell you about Pivot, our twice-weekly podcast.

• 37:00Speaker 03

  That's right, Kara. What a thrill. It's a chance for us to break down all the big things happening in tech, business, and politics.

• 37:07Speaker 02

  Yes, and I keep you in check so people can make it through each episode, whether it's digging into constant changes in the world of AI and social media, or trying to keep up with whatever the fuck Elon is doing. We're here to give you our take on all of that.

• 37:18Speaker 03

  Every Tuesday and Friday morning, we drop a new episode about some of the major stories of the moment.

• 37:24Speaker 02

  And Scott is a prediction machine, gazing into his crystal ball to tell you about where it's all heading.

• 37:29Speaker 03

  That's right.

• 37:30Speaker 02

  So if that sounds like a good time for you, especially Mr. "That's right", you can follow us on your favorite podcast app to get new episodes every week.

• 37:39Speaker 03

  Boom.

• 37:47Emma Grede?

  I really want to talk to you about leadership style, because I feel like this is something that fascinates me with people that have been successful in multiple different areas. You've said that your number-one attribute is telling the truth. And I think that that is such a sort of lost and forgotten skill now, because people want to people-please, and to be popular, and to trend, and to go viral. Like, we have to say, or people think they need to say things that people want to hear. What's the hardest truth? When you start to think about your clients and the people that you're around, A, I want to understand how you are able to do that, like, to keep telling the truth and keep getting the clients. But I wonder if there's a particularly hard truth that you've had to tell

• 38:31Emma Grede?

  that, you know, has led you to where you are today? Like, is there one big thing that you're like, "This is what I do on a regular"?

• 38:38Speaker 01

  You're good. You're really good at this.

• 38:41Emma Grede?

  Thanks, Dean.

• 38:42Speaker 01

  One of the values that I have at the company is challenge and respect. So let's talk about leadership, and then I'll get to truth. Challenge and respect is one of these things where...

• 38:53Speaker 01

  We have to be able to have a disagreement and

• 38:59Speaker 01

  get to the other side without you ever feeling disrespected in that process. And that's very hard to do.

• 39:04Emma Grede?

  Very hard to cultivate.

• 39:05Speaker 01

  It's much easier to yell and get mad or leave. In fact, it's the reason why I just went back to a four day work week. After all these years and I was fighting with it with not me fighting with it, but more with people in my company.

• 39:19Emma Grede?

  Sorry, from four, from what to four?

• 39:21Speaker 01

  From three to four.

• 39:22Emma Grede?

  From three to four, okay.

• 39:23Speaker 01

  And I went back to it because what I realized is that.

• 39:26Emma Grede?

  Don't get me started.

• 39:27Speaker 01

  People, people, people don't have confrontation on Zooms.

• 39:31Emma Grede?

  Nothing good ever happened on a Zoom.

• 39:33Speaker 01

  Well, that's not true either.

• 39:35Emma Grede?

  Oh, Steve, come on. When did a good idea come out of Zoom? When did someone go, you pointed at a box and you were like, yes, you, excellent.

• 39:42Speaker 01

  They probably came up with Zoom on a conference call.

• 39:48Emma Grede?

  That was the last good idea that came out of Zoom.

• 39:51Speaker 01

  Okay.

• 39:56Speaker 01

  If you don't deal with conflict and confrontation, people in general do not like conflict. So if you put, but businesses need conflict in order to grow. You need conflict, you need that tension. So if you don't put people in decisions that create conflict and you allow Zooms to be the, the way you communicate, I think you lose conflict resolution, which is going to help the company and help everyone. Okay, so that's challenge and respect, right? That has to be omnipresent within the way you conduct and do things. So when you talk about telling the truth, the hardest thing for me to do is find the person who's willing to hear the truth inside of a company.

• 40:39Speaker 01

  And that's usually the CEO, because they don't have a place to hide.

• 40:44Emma Grede?

  Yes.

• 40:44Speaker 01

  The chief marketing officer, a lot of times.

• 40:49Speaker 01

  Yeah, they could do that.

• 40:50Emma Grede?

  Skate star, yeah, exactly.

• 40:51Speaker 01

  The CEO, the CFO, when you start getting into that realm of the company, more fact based, they can handle the truth well.

• 41:03Speaker 01

  CMOs and performance marketing companies have to handle the truth as well. So I don't want to just, just, I don't want CMOs to get upset about this. But understanding that truth and finding someone who can hear that truth is a very important part of the process. So, cause I'm not talking to, I'm talking to the company, right? And so it's like, if it's me and you, we work at a company, we're employees and, or whatever. And we're, we're, we're arguing over what book to put here. We have to have direct conflict resolution. But when you're doing it with a company, you have to find who's the person

• 41:34Emma Grede?

  Yes.

• 41:34Speaker 01

  within the company that can hear the truth. Cause you need that person and then

• 41:38Emma Grede?

  To do something.

• 41:38Speaker 01

  to do something and distribute that fact within the organization. So finding the person is, is the, probably the biggest job in corporate America. There was a second question you asked me today.

• 41:49Emma Grede?

  Well, I want, I want to understand like,

• 41:51Speaker 01

  How do I?

• 41:51Emma Grede?

  how do you see the truth? Like, you know, because there's one thing being able to say it and tell it. How do you even see it and find it?

• 41:59Speaker 01

  When you remove yourself, a, a lot of my, my, the great relationships that I have with artists, and I've been fortunate to work with some of the greatest artists in the world, producers and creators overall, is because I would tell them the truth. The thing that I realized, Emma, I don't give a fuck. Eminem, Nas, 50 Cent, Lady Gaga, you name the artist, I don't care who it is. Beyonce, this, that. Anytime you tell the great artists the truth, they want to hear it. It is such an odd thing. It's the artists that are not that talented that want to be lied to. The best of the best want the truth.

• 42:41Emma Grede?

  Yeah, I think the best people always want the truth.

• 42:43Speaker 01

  It's the craziest thing.

• 42:44Emma Grede?

  I think the best, I mean, the best employees, the best employees want the truth. The best husbands and wives want the truth.

• 42:50Speaker 01

  I'd be saying it, it'd be leaving my mouth and I'm like, shit, I hope it's gonna be like, and they're like, yo, I really respect you. I'm like, oh shit, word? I want you around more.

• 43:01Emma Grede?

  Yes.

• 43:02Speaker 01

  If you, if you, if you can tell an artist or any creative, the unvarnished truth with a rational fact behind it, with, with a real thing behind it, not just saying the wrong shit just to be coming at it, just to have a different point of view. But like, not a hard take, but like, really like, I think you should look at it that way because da, da, da, da. And you're not running around asking for shit? So you're not incentivized to tell them the truth or not the truth or whatever? You're just giving it from a heart? You, you, you can develop long lasting friendships that way.

• 43:35Emma Grede?

  And I wonder, how do you actually even create that culture internally? How do you create a culture of challenge and respect over just agreeing?

• 43:44Speaker 01

  I, I can't tell you I'm there yet. I'm not there yet. I'm not there. Before this podcast started, I was in the back having a challenge and respect discussion. I had this room bubbling because.

• 43:56Emma Grede?

  They tell me.

• 43:58Speaker 01

  You probably got worried that Steve is bugging out.

• 43:59Emma Grede?

  They're just like, we're just gonna give Steve a minute.

• 44:01Speaker 01

  Yeah. They cut the air conditioner off.

• 44:07Emma Grede?

  Let's go this guy down.

• 44:10Speaker 01

  The. No, the challenge and respect thing, um, I'm not there yet. And, and, and I'm dealing with something that you asked me, did you feel trapped? Early in this conversation, you said, and I said, I feel more trapped now. I feel more trapped now because it's hard for me to tell somebody who is accustomed to this new day and age of how you work and.

• 44:35Emma Grede?

  Softly.

• 44:35Speaker 01

  The soft shit, work from home and Zoom and all of that type of shit to have this type of conversation with me. But I also come to the conclusion that I'm not changing either. And this company is going to live and succeed based off of how I run it. So I have to find people who can work with me. Cause I'm not changing. And that's just the way it is. These are the things that I believe in. And this may not be the place for you.

• 45:05Emma Grede?

  And that's fine because not everywhere has to be for everybody. I think I've come to a very similar conclusion and it isn't to say that one is right or one is wrong, but I think that workplace culture, especially when you're in a privately owned company is down to whoever is leading that company. And you can get on board or you can go. And I feel like it's very, very clear.

• 45:24Speaker 01

  And but again, and that should also not be disrespectful. Like this is just not for you. It's cool. It's fine. I'm not wrong because we can argue about anything. I could argue about anything. We could all argue about, should it be three days a week? Well, maybe four days a week is better, or maybe we should do this, or maybe you should talk to them that way, or maybe like. You know, bring massages in once a week for employee morale. I can make up a bunch of shit. Okay, and it could be right. It's just not right for the culture of the company that I'm building. Like you can go into people's house, you go into, you ever go into like a friend's house growing up? And they'll be arguing and shit and it looks chaotic, but yet it's peaceful in that house.

• 46:05Speaker 01

  It's like, everybody has their own version of the culture of their household.

• 46:10Emma Grede?

  Totally.

• 46:10Speaker 01

  That may not work for your household, but it works well in that household.

• 46:14Emma Grede?

  I want to ask you two questions about leadership before we move on to this. The first one is specifically as it pertains to women, right? You are extremely successful, run multiple different companies. When you start to think about women in the workplace, right? Specifically, female leaders. I want to understand if you feel like there are really big, obvious differences. And because you're somebody that gives a lot of advice, yes, I'm getting you into it. Because you're someone who gives a lot of advice and you tell the truth. How are you feeling about female leaders in your company? Do you think that you treat them differently? Do you give different advice to women over men? I'm curious to hear from someone who's going to tell the truth.

• 46:57Speaker 01

  I'm gonna talk about my company, then I'll talk about the industry.

• 46:59Emma Grede?

  Yeah.

• 46:59Speaker 01

  So.

• 47:00Emma Grede?

  Fine, I'll let you do that.

• 47:02Speaker 01

  When I speak to a woman in my company, I don't see it any different than when I speak to any man in my company. And that's actually, could be a problem. I don't round the edges. I don't see, the way I look at my business, I put the company in the middle. And we are all in service to that company, all of us. We all have a role and play of service to that company. And that's the only way I see it. So whether you're a man or a woman, my expectations doesn't change because you're white, black, you know, or gender. It just doesn't, it doesn't, I don't, I don't feel that difference. I don't state that difference. Now, the person on the other side may want to hear some difference.

• 47:42Speaker 01

  They may want a softer tone, or they may want some, some understanding as a result of something. And I can't tell you that I do that. And there's pros and cons in that, I am sure. What I've realized, when I look at the macro and I go to the, some of the great leaders, the women that I've met in the industry. Is that I haven't seen much difference from them than men. So one of my very good friends is the Sunda, the CEO of

• 48:17Emma Grede?

  The Sunda Duckett.

• 48:18Speaker 01

  The Sunda Duckett, right? Right? If you speak to the Sunda, you wouldn't know who the fuck you're talking to. Right? Like if you AI her voice and they put a man's voice behind it, you would think that you're getting fucking screamed at and broken down every five minutes because she's tough and her expectations are up here. And she don't give a fuck about nothing, but we gotta get to the top. And like, that sounds like a lot of men that I know. And it has that same kind of energy. But whether it be Kellin Kelly at AT&T or I can go through the list of solid women leaders that I've met. They do not have any chill as a result of, because they're women, as it relates to the same expectations and results

• 49:02Speaker 01

  that they want as a man. Are they softer? Nah. No.

• 49:10Emma Grede?

  All right, work-life balance. This is one that, you know, I feel like I am constantly in some kind of, you know, conflict about just my thoughts and my feelings about this. And I'm curious as somebody that employs hundreds and hundreds of people that, you know, has had businesses in this current business climate, has had businesses 20 years ago. Where do you stand on the whole work-life balance? As a point of view, as a, as an argument, as a, as something that is like a requirement from staff right now?

• 49:43Speaker 01

  I, I, I, uh, as an entrepreneur, I, I don't think that you have the luxury of coming up with that idea. I, I, I just, that's just like, you know, you, you, you are hiring people. You're an independent company. You are hiring people. People are putting their kids in daycare and college and private schools, et cetera, based off of your leadership and their belief in you. And you're running around working on work-life balance when the company is at risk of putting, you know, putting these kids in their private schools at risk of, their college tuition at risk.

• 50:24Speaker 01

  I, I, so I'm like, you have to afford work-life balance if you're the CEO of an entrepreneurial organization.

• 50:32Speaker 01

  In general, how I feel about it, let's say things are going well. Let's say things are going well. Everything's going well, right? So we're skims right now, everything's going well. You can have work-life balance. I seen you and your husband in Switzerland, having a good time, walking up mountains, taking pictures and having a good time. Beautiful skies. You should do that. Things are going well. If the company was being fucked up and I seen you posting that, your phone would be ringing. I'd be like, what the fuck is wrong with you? You bugging? I would, I would, I would do that.

• 51:03Emma Grede?

  No, you actually would.

• 51:05Speaker 01

  I would do that like.

• 51:05Emma Grede?

  You sign up, you actually would go like where you at.

• 51:08Speaker 01

  What the fuck is you doing right now?

• 51:09Emma Grede?

  And I would think that that's the right thing to do. Because you can't, again, when you are building, when you're starting out, when you're in those early days, you can't do that shit. Like, you can't. You can't go off to Europe and take a four-week vacation. You can't.

• 51:23Speaker 01

  I'm not answering my phone. No, no. How do you feel? Let me ask you a question. How do you feel about auto reply?

• 51:30Emma Grede?

  No, no. If I see an out of office, my head explodes. In fact, do you know, I've never, I haven't written an out of office since maybe I was 24 years old.

• 51:39Speaker 01

  I have no idea.

• 51:40Emma Grede?

  I'm 42.

• 51:40Speaker 01

  I don't know where to program that on the thing. I don't even, out of office? Are you kidding me?

• 51:46Emma Grede?

  But it's a mentality, right? But you know we sound older. Fuck, you sound like the people like whining about rock and roll or something.

• 51:53Speaker 01

  I'm happy that I'm happy. I'm clearly older than you and you're saying the same shit. So I actually feel younger.

• 52:01Emma Grede?

  You are. You're officially in your early forties right now. Listen, because I feel like people will be screaming at us. I understand what is the requirement of the way that we live, right? People do not want to be glued to their phones. They don't want the expectation that they have to answer, you know, emails at 10.

• 52:17Speaker 01

  They are glued to their phones. They are glued to their phones.

• 52:20Emma Grede?

  That is something else. They are glued to their phones, but maybe it's for their own enjoyment. I think that we have to be extremely specific here. If you are an employer of a company, there is one thing. But if you want to start talking about being an entrepreneur, if you want to start talking about being a founder, if you want to be somebody that is truly ambitious, the idea that you can decouple extraordinary effort and extraordinary results is farcical.

• 52:42Emma Grede?

  You're nuts. You cannot. It's you cannot have one without the other. And I think every founder I know, every entrepreneur that I know has a period of unbelievable grind, unbelievable graft, unbelievable hustle, wherever you come from, whatever you want to call it. And it doesn't come on a four day work week and it doesn't come not answering emails or the phone after a certain time. It doesn't matter. Man, woman, with kids, without, whichever industry you're in, it just, that is what it is.

• 53:12Speaker 01

  I, I, again, I, listen, I agree with everything that you're saying. And um, I hope that anybody that is watching this, who is looking for mentorship, are willing to subscribe to these values. Because if you don't subscribe to these values and read in between the lines of some of the things that we're saying and actually what we're, what we mean, right? It's, it's an attitude. It's a, it's a mindset that's required to win. That i- if you're not willing, if you're not all in on that, then you're just not gonna win. I, I don't give a fuck what it is. It, that's, if there's any wisdom I can provide, being uh, somebody who's been doing this for a while, is that I've never seen anybody win

• 53:55Speaker 01

  long-term with shortcuts. And, and finding out that you're not successful and that your, your idea didn't work really late in life is terrible. Like tricking yourself, I used to call it the Ponzi scheme, a lie to yourself. Like you can lie to yourself for a really long time. But could you imagine when that lie runs out and now you're in your mid fifties?

• 54:18Emma Grede?

  Fuck that.

• 54:19Speaker 01

  And you just found out that you were lying to yourself all these years? You're really not the person you said you were to yourself? And do you know that that's what most people do all the time? That's actually the normal course of life. Like you just keep lying. Because like, once you start, once you lie to yourself and you start getting on that pattern of lying to yourself and believing this inflated version of the truth. And you lack self-awareness. That drug and the way you can rationalize that can take you so far. And you just keep putting them off the pain. Just don't deal with it. You don't deal with it. You don't deal with it. It's that person's fault. You're the victim. It's over there. It's over there. Now you look up and now there's no place to run and you're 52.

• 55:03Speaker 01

  And I'm not saying forget about it.

• 55:05Emma Grede?

  I'm like, I could never. I could never. I could never.

• 55:14Speaker 04

  Today's episode is sponsored by NerdWallet's Smart Money Podcast. Ever Google a money question and end up 12 tabs deep with 12 different answers? This podcast is your shortcut back to clarity. NerdWallet's Smart Money Podcast breaks down financial decisions with a team of trusted journalists. They explain the why behind decisions like investing, home buying, and choosing credit cards with clear, research-backed insights. No jargon, no misinformation. Make your next financial move with confidence. Follow NerdWallet's Smart Money Podcast on your favorite podcast app.

• 55:44Speaker 05

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• 56:25Speaker 05

  Today, nine Fortune 10 companies run on Claude for the work they want to get right. And these businesses are helping Anthropic shape what comes next. Build your business with support from Claude at claude.ai/odyssey.

• 56:44Emma Grede?

  I want to ask you this question. Is there, is there a leadership lesson or a lesson more generally in business that you've learned the hard way?

• 56:53Speaker 01

  Yeah. Sell externally, not internally.

• 56:57Emma Grede?

  Please expand.

• 56:58Speaker 01

  Yeah. If you're a salesperson, you could actually sell yourself and sell the people on something that's an idea that's actually not necessarily the right way to do. You believe in it so much, you sell it to your people and you sell it to yourself. And you can, to untangle that when it doesn't work is hard because you've sold everybody on this idea. So it's fine to sell externally. Don't sell internally. The internal stuff has to be all, no frills, all truths, no, nothing inflated.

• 57:35Emma Grede?

  When have you, when have you done this? Give me an example.

• 57:38Speaker 01

  Believing in an idea longer than the actual idea was viable and I sold it to myself and I sold it to my people, yet it still wasn't an idea.

• 57:48Emma Grede?

  Yeah, fair. No, that makes total, total sense.

• 57:51Speaker 01

  You've done it?

• 57:52Emma Grede?

  I might still be doing it.

• 57:56Emma Grede?

  Who knows? That's a great, it's a great piece of advice. I wanted to ask you, like, I want to talk to you a bit about money because people find it very difficult to talk about money. And I wonder if there is some advice, like financial advice, that you wish you'd have had when you were 25 that you'd be happy to share?

• 58:13Speaker 01

  The habit of saving money is important. The idea of saving money is important. One of the things that I learned very early was, I forgot what it was. It was a, it was a life insurance account, but it was life insurance that had some bond effect connected to it. So, and it was like $200 a month. And I remember the guy saying, if you put $200 a month in 15 years, it's going to be, you know, $250,000, I'll make up a number. But the number, whatever the number was, I was 21 years old, sounded like a big number to me. And I remember thinking, really?

• 58:56Speaker 01

  But he explained to me the idea of money being compounded.

• 59:03Speaker 01

  And obviously, the beneficiary of money compounding is time. And I did it because I was trying to get to that number at the end, that $250,000 number, whatever it was. And it was like four years ago that I stopped paying it. I was still paying $200 a month.

• 59:20Emma Grede?

  No, you were not.

• 59:22Speaker 01

  Yeah.

• 59:22Emma Grede?

  No, you weren't.

• 59:23Speaker 01

  Through different, by the way, through different business managers and all kinds of shit. There was still this thing.

• 59:28Emma Grede?

  There's 200 bucks going.

• 59:30Speaker 01

  It was $200 going out every month.

• 59:32Emma Grede?

  That's amazing.

• 59:33Speaker 01

  And it was a significant sum of money. It was, you know, it was upwards of $600,000. But I remember thinking like, how serious I took that at that time. And it was a goal in my head.

• 59:45Emma Grede?

  Yeah.

• 59:47Speaker 01

  Saving money early, it doesn't make a difference if it's a lot of money. Just the habit of saving money, anything consistently is important. It's no different than somebody saying, you know, working out daily to lose weight or whatever. Saving money at a young age consistently, fuck the amount. Don't think of the amount at that moment as insignificant. What you're trying to do is create compounded effect over time. That is a very important thing. Even if you're an entrepreneur, I don't care. This idea that you're an entrepreneur, so you don't have to save money? Don't believe that. Saving some money and having it there consistently, the habit of that, that muscle of that, I think is very important.

• 1:00:32Emma Grede?

  Yeah, and I think it's very interesting because it's really about frameworks or habits, as you say. Because what that does, like when you start to think about compounding effects, they can apply to so many other things in your life. And it's teaching you that doing something with consistency and doing something repeatedly, it's actually, it's like a muscle, right? Are there other places in your life where you have habits that are just second nature at this point?

• 1:00:57Speaker 01

  Most of them are all work related. You know, like it's a weekend, you're scanning for a problem.

• 1:01:05Emma Grede?

  I completely know that feeling. I'm like, everything's fine. So what's not?

• 1:01:10Speaker 01

  Yeah, it's like you scan for a problem like, and I know where they're finding the problem. I know the right question to ask. That's one of my things that I I I do that with. I guess sleep deprivation, I've learned how to do that. Well.

• 1:01:24Emma Grede?

  I heard that you only sleep like four or five hours a night. That's psycho. Why?

• 1:01:29Speaker 01

  I'm not happy about that.

• 1:01:30Emma Grede?

  You shouldn't. That's not good for your longevity.

• 1:01:32Speaker 01

  I'm not happy about that.

• 1:01:33Emma Grede?

  I'm just saying.

• 1:01:34Speaker 01

  That doesn't, that sounds like some, I travel way too much and I don't sleep.

• 1:01:38Emma Grede?

  Are you, are you not a good sleeper? Or do you like, what is the thing? You don't, you don't need a lot of sleep? Or you've just got so much happening and so much going on in your brain, you can't sleep? Oh, no, you've got to change that. Quite frankly, you're too old for that.

• 1:01:50Speaker 01

  I don't, yeah, it's probably true. I don't think I like sleeping.

• 1:01:55Speaker 01

  I actually don't think, I actually don't think I like it.

• 1:01:58Emma Grede?

  Who doesn't like sleeping?

• 1:02:02Speaker 01

  I don't like it. I just thought about that for the first time. If I'm tired, yeah, I want to sleep, but I don't like look forward to sleeping.

• 1:02:10Emma Grede?

  Are you a good rester? Are you someone that just like sits down and watches like a good movie and can just like chill out?

• 1:02:16Speaker 01

  Hell no.

• 1:02:16Emma Grede?

  No, you're not a meditator.

• 1:02:19Speaker 01

  Shut up.

• 1:02:21Speaker 01

  That sounds, that sounds like, that sounds like a Zoom.

• 1:02:31Emma Grede?

  All right, let's talk about legacy and the next generation because there's going to be so many people here that want to understand like, why are you working? Why are you still working as hard as you're working? What do you want to be your legacy?

• 1:02:46Speaker 01

  Well, I have a, I have a 20 year old daughter, Sophia.

• 1:02:50Emma Grede?

  I met her.

• 1:02:50Speaker 01

  Yeah, and she is at Columbia University.

• 1:02:53Emma Grede?

  Are you so proud when you say that?

• 1:02:55Speaker 01

  I'm very proud of her.

• 1:02:56Emma Grede?

  You should be.

• 1:02:57Speaker 01

  She's really smart. My legacy, i- it's important to me that I have a son, Pharaoh, and a daughter, Phoenix. I, I want my children, obviously, to be something, to do something and continue to do things that they're, they're proud of. It's important to me that my contribution to hip hop. In the culture of hip hop is something that stands the test of time because I feel like I put a lot in and I got a lot out of of that relationship and and everything that hip hop music has done for me and my family and its impact on the world. And that United masses and the companies that I build are something that when people look back in books when they go like, man,

• 1:03:41Speaker 01

  something changed that I was there to to make a shift to put a dent in what was happening in the world. And the reason why that matters is because I've taken so much of time away from my family.

• 1:03:54Emma Grede?

  Yeah.

• 1:03:54Speaker 01

  At least we could say.

• 1:03:55Emma Grede?

  At least.

• 1:03:56Speaker 01

  We have that to show for it. I could have done well financially without taking that much time away from my family.

• 1:04:02Emma Grede?

  It's very lovely that you say we.

• 1:04:03Speaker 01

  To do the things that we're doing, the things that we're tackling are are are hard jobs. It's not like just trying to make some money. I could, like, I could go out and do a couple of things to make money. But to like build a company that was going against major label record, you know, industry or, you know, build an advertising company that didn't exist, that was focused on understanding where culture was going.

• 1:04:26Emma Grede?

  To change the game.

• 1:04:27Speaker 01

  To change the game. And that's, to me, that's beyond money, you know? Look, even even back in the day, like when I first went and put money behind Carol's daughter to start that brand, to help Lisa Price in that company, you know, we were the first African American beauty brand in Sephora.

• 1:04:45Emma Grede?

  Crazy.

• 1:04:46Speaker 01

  They they they weren't none.

• 1:04:47Emma Grede?

  Crazy.

• 1:04:48Speaker 01

  A black girl would go into Sephora.

• 1:04:50Emma Grede?

  Nothing.

• 1:04:50Speaker 01

  Start scratching her head looking for some fucking shampoo.

• 1:04:54Speaker 01

  I was, right?

• 1:04:57Emma Grede?

  Yeah, she was walking out with nothing.

• 1:04:58Speaker 01

  She was walking out with nothing. Or you or or or it was like, I remember thinking like, how do you go? I used to try to think like, I'm gonna go to Carnival Cruise Lines. Like, all these people go on these cruises. And like, you want to use all the shampoo that's right there. All that shit is fucking your shit up.

• 1:05:13Speaker 01

  The conditioner is fucked up.

• 1:05:14Emma Grede?

  You really thought this shit through. You really, really did.

• 1:05:17Speaker 01

  I was thinking through all my. Everywhere you go, if you're a black woman, there's nothing convenient for you, including in Sephora, you know? And like, doing those things to me are important. But again, it's like what we were talking about. What's the idea? What's the problem you're solving? And and how are you going to solve it? And is there an audience for it? All of the businesses that I've involved in, I'm proud to say that I I've gone at it with that level of thought.

• 1:05:43Speaker 01

  You know, and they've all had varying degrees of success. But that was the level of thought that was into each one of those things.

• 1:05:49Emma Grede?

  Incredibly thoughtful. They're hurrying me to rush up now, so you've got to do rapid fire quick. All right, this is a question that I missed for you, but I really wanted the answer. Who do you think is killing it right now at the intersection of business and culture?

• 1:06:02Speaker 01

  Who's killing it right now?

• 1:06:03Emma Grede?

  Yeah, who's killing it?

• 1:06:04Speaker 01

  You guys are killing it. The team at Skims is killing it.

• 1:06:10Speaker 01

  Who's killing it right now?

• 1:06:14Speaker 01

  There's about to be a whole nother new opportunity with all these streamers.

• 1:06:17Emma Grede?

  Oh, I know.

• 1:06:18Speaker 01

  Yeah.

• 1:06:19Emma Grede?

  The streamers.

• 1:06:20Speaker 01

  Who's killing it right now? Fuck. I would say, damn it, I don't want to just sound like that because you're right here.

• 1:06:27Emma Grede?

  It's okay, go ahead.

• 1:06:28Speaker 01

  Shit.

• 1:06:29Emma Grede?

  I mean, I don't know.

• 1:06:30Speaker 01

  No, you guys are crushing it.

• 1:06:31Emma Grede?

  Well, I do think the, I do think the streamers.

• 1:06:34Speaker 01

  The streamers that have a chance to kill it, all the guys in AI, that's not, I don't see that as culture.

• 1:06:41Emma Grede?

  No, I don't see it as culture, is it?

• 1:06:43Speaker 01

  No, it, it, it will get to that, but it's not there yet.

• 1:06:47Emma Grede?

  We're still all figuring it out.

• 1:06:49Speaker 01

  Yeah, we're still figuring it out.

• 1:06:50Emma Grede?

  It's too early.

• 1:06:50Speaker 01

  But I'm saying that.

• 1:06:51Emma Grede?

  There's not like, there's not an artist or someone that you look at like that and you're like, they have turned themselves into a business and a brand and.

• 1:06:58Speaker 01

  Travis, Travis Scott is killing it.

• 1:07:00Emma Grede?

  Travis, yeah, yeah.

• 1:07:02Speaker 01

  Travis Scott is killing it, Pharrell is killing it, you guys are killing it.

• 1:07:07Emma Grede?

  Just stop there, that is perfect. I'll take it. You put me next to Travis and Pharrell, that I think that will all be very happy. This is a really random question, but I actually nearly texted you. What do you make of Cracker Barrel's rebrand?

• 1:07:21Speaker 01

  I never fucked with the name. I haven't seen the rebrand. I, I.

• 1:07:25Emma Grede?

  You know this news, Steve Stout, don't pretend with me. What, what, okay, what do you think about risk and audience? Like, give me your point of view on the premise of it.

• 1:07:34Speaker 01

  Risk and audience?

• 1:07:35Emma Grede?

  Yeah.

• 1:07:35Speaker 01

  Yeah. When you have nothing to lose, I think you should go for it when you have nothing to lose like that. I think when you're in, when your back's against the wall and you have nothing to lose, then going for it is the best available option. That's my risk analysis on Cracker Barrel.

• 1:07:52Emma Grede?

  First thing you do when you wake up?

• 1:07:54Speaker 01

  Cold plunge.

• 1:07:55Emma Grede?

  Oh, you're a cold plunger?

• 1:07:57Speaker 01

  You can't tell by my skin. It's not working.

• 1:08:17Emma Grede?

  You're so silly.

• 1:08:21Emma Grede?

  That's so good. What's the last thing you do before you go to bed?

• 1:08:24Speaker 01

  Think about what I have to do the next day. I scan the day, scan the day.

• 1:08:29Emma Grede?

  Of course you do. What are you currently aspiring to?

• 1:08:32Speaker 01

  Oh, man. I really wanna see how far I can take this thing. This idea that there's this place where peace and ambition coalesce. I love that idea, like this idea that you could really be at peace and be as ambitious as ever.

• 1:08:51Emma Grede?

  Oh, we need another podcast. Now, you write at the end, you say that?

• 1:08:57Speaker 01

  You asked me that question.

• 1:08:58Emma Grede?

  Fucking annoying, this timing. What's a book that changed your life?

• 1:09:03Speaker 01

  The Greatest Salesman in the World.

• 1:09:05Emma Grede?

  What is something that you valued when you were starting out that you no longer value?

• 1:09:10Speaker 01

  Acceptance from others, the acceptance of others, like, yeah, you know, I like Steve. All that bullshit. People don't, people like whatever the fuck they, like it was going on right now in the world. People just, they just run around liking whoever's popular at the moment. Fuck them. But like, that, that thing was a thing for me in the beginning, like, you know, people really don't like you because, and that shit used to affect me, like, really? What did I do? And then as I got older, I realized, I don't fucking like them.

• 1:09:44Speaker 01

  How about that part? How about that part, actually?

• 1:09:47Emma Grede?

  Fair enough. And you end your emails with much respect, which I think is such a beautiful way to sign off an email. What does respect mean to you?

• 1:09:57Speaker 01

  I respect your time, I respect your perspective.

• 1:10:01Speaker 01

  It really comes down to this idea that I want you to expect from me this idea of you should expect from me what I expect from you. This mutual exchange of of a feeling towards the way we hold one another, the way we hold the regard we have for one another. That's a that's a very important thing to me because for years, and it's important, you'd respect people from afar or you'd respect them without any concern of if they had a respect for you. Well, I would do that because I wanted to be in their good wishes and be in their good graces and I'd be like, you know, I'd have this respect. And now I do it. I don't have that idea anymore. I want, obviously, it's not respect unless it's mutual respect.

• 1:10:46Speaker 01

  There is no respect unless it's mutual. There's no way I can respect you if you don't respect me. It doesn't work, you know? So the idea of much respect for everybody, it doesn't have to, it's it's for you, it's for you, it's for you, it's for you. It's this mutual exchange that's important to me that I I want people to know that's that's sort of where I'm at with it.

• 1:11:05Emma Grede?

  Yeah, I I think it really shows and, you know, I respected you before I met you. I respect you even more now that I actually know you.

• 1:11:12Speaker 01

  I respect the shit out of you and I'm proud of you.

• 1:11:14Emma Grede?

  Thank you so much, Steve. Love you to death.

• 1:11:17Speaker 01

  Thanks.

• 1:11:23Emma Grede?

  If you're loving this podcast, be sure to click follow on your favorite listening platform. While you're there, give us a review and a five star rating and share an episode you loved with a friend. We'll be so grateful. A Spy with Emma Grede is presented by Odyssey. I'm your host, Emma Grede. Our executive producers are Corinne Gilliard Fisher, Derek Brown, and me. Our executive producers from Odyssey are Maddie Sprung Kaiser, Leah Reese Dennis, Asha Saluja, and Jenna Weiss-Berman. Stephen Key is our senior producer. Sound design and engineering by Bill Schultz. Angela Peluso is our booker. Original music by Charles Black. Video production by Evan Cox, Kurt Courtney, Andrew Steele, Carlos Delgado, and Arnie Agassi. Social media by Olivia Homann.

• 1:12:08Emma Grede?

  Special thanks to Brittany Smith, Sidney Ford, My Teams at the Lead Company and WME. Maura Curran, Josefina Francis, Hilary Schuff, Eric Donnelly, Kate Hutchinson Rose, Tim Meeke, Shaun Cherry and Lauren Vieira. If you have questions for me, you can DM me at aspirewithemagreed. Greed is spelt G R E D E. That's aspire, A S P I R E with emagreed. Or you can submit a question to me on my website, emagreed.me.