He Built the Room They Wouldn’t Let Him Into with Steve Stoute

Summary

Aspire with Emma Grede

Episode: He Built the Room They Wouldn’t Let Him Into
Guest: Steve Stoute
Date: November 11, 2025
Host: Emma Grede

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Episode Overview

This episode of Aspire with Emma Grede features marketing powerhouse, music executive, and entrepreneur Steve Stoute. Renowned for bridging the worlds of hip hop, corporate America, and culture-defining brands, Stoute discusses leveraging his upbringing, the power of authentic relationships, the DNA of breakthrough ideas, and the realities—and myths—of entrepreneurship. Throughout, Emma and Steve dig into making ambition count, building inclusive rooms, decoding “culture” for business, and how truth-telling underpins all forms of leadership and legacy.

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Key Discussion Points & Insights

1. Building the Room When You Aren't Invited

• Background isn't baggage—it's a key to access:
  Stoute’s Queens upbringing and Trinidadian immigrant roots taught him perspective and resilience.

  "Your background isn't baggage. It's the key to unlock everything you've been chasing." — Emma (00:26)

• Relationship skills as a business superpower:
  Navigating exclusion in corporate America forced him to develop “relationship skills” as essential tools—not just creative vision.

  "It was 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." — Steve (03:37)

2. Learning from the Originals

• Mentorship wasn't transactional:
  Instead of requesting mentorship, Stoute sought proximity and modeled successful figures informally, absorbing from legends like Quincy Jones, Clarence Avant, and Jimmy Iovine.

  "Somebody chose you... without saying it publicly that they were going to take you under their wing." — Steve (30:03)

• Studying success up close:
  Growing up alongside hip hop’s ascendants (LL Cool J, Run DMC, Russell Simmons) gave him firsthand, tangible proof that big dreams were attainable—even as the economics lagged.

3. Hip Hop, Culture, and Business: The "Bridge"

• Translating hip hop for corporate America:
  Stoute became the cultural “bridge,” educating hesitant brands on the true value and commercial potential of Black culture, long before multicultural marketing was mainstream.

  "Trying to convince somebody to do something when they don't need it is extremely difficult." — Steve (16:01)

• Jay Z, Pharrell, and shifting perceptions:
  He recounts pivotal projects like Will Smith’s Men in Black soundtrack and Jay Z’s Reebok deal, sparking new chapters for artist entrepreneurship and product collaboration.

4. What Makes an Entrepreneur?

• Everyone can start a business—but few can build one:

  "Everyone can start one. Well, that's all I'm talking about." — Steve (24:07)

• Maniacal drive:
  The real entrepreneurs are “obsessed”—driven by ideas they cannot shake, weathering repeated failure (see: Travis Kalanick) because they have no choice.

  "Unless you have a dream in your head that you can't get out, it's not worth it." — Steve (27:10)

5. On Mentorship and Emulation

• Mentors choose protégés:
  Seeking a mentor is “insane”—instead, ask questions and emulate those you admire.

  "You can't just microwave a mentor, man." — Steve (33:58)

6. Decoding "Culture" in Business

• The word 'culture' is overused:
  Stoute critiques how “culture” has become a token catchall, instead of a deeply contextual understanding of collective rituals, language, and shared meaning.

  "It's turned into ketchup—you can put it on anything." — Steve (34:52)

7. Staying Relevant: Remove Your Opinion

• Act as a vessel, not a tastemaker:
  True cultural translators leave their personal taste aside, focusing on facilitating (not dictating) the exchange between emerging subcultures and brands.

  "My personal point of view is really not important... I'm a vehicle and a vessel." — Steve (36:58)
  "You don't got to like it, you just got to understand it." — Emma (38:37)

8. Truth-Telling & Leadership

• Challenge and respect:
  Stoute’s leadership values disagreement with respect; believes growth only happens through candid, sometimes uncomfortable, conflict.
• Artists and employees want honesty:
  The best talent craves direct feedback—mediocre employees (and artists) prefer comforting lies.

  "Anytime you tell the great artist the truth, they want to hear it... the best of the best want the truth." — Steve (47:22)

9. Workplace Culture, Gender, and Work/Life Balance

• One set of standards, regardless of gender:

  "When I speak to a woman in my company, I don't see it any different than when I speak to any man... my expectations don’t change." — Steve (52:03)

• You must earn work/life balance:
  No shortcuts for entrepreneurs—extraordinary effort is required, especially in the early stages.

  "To decouple extraordinary effort and extraordinary results is farcical. You're nuts. You cannot have one without the other." — Emma (57:53)

10. Money Mindset, Habits & Compounding

• Start small, be consistent:
  Building a habit of saving—even a little—compounds into security and freedom.

  "It's no different than working out daily... Saving money at a young age, consistently—fuck the amount." — Steve (65:16)

• Apply compounding to life:
  Consistency in any useful habit creates lasting, exponential results.

11. Legacy, Sacrifice, and the Next Generation

• Contributing to more than ‘making money’:
  Steve measures legacy by positive, indelible contribution to culture—not just financial gain.

  "I want my contribution to hip hop and the culture... to be something that stands the test of time." — Steve (68:39)

• Family sacrifice:
  He acknowledges the cost to family time and wants that trade-off to be meaningful.

12. Rapid-Fire Wisdom

• Entrepreneurs should “sell externally, not internally”—don’t convince yourself of your own hype. (63:40)
• Big lesson: Let go of the need for outside acceptance as you age; focus on mutual respect.

  “There is no respect unless it's mutual.” — Steve (76:35)

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Notable Quotes & Memorable Moments

• On the myth of “selling out”:

  "Being successful and selling out were closely assimilated... That's such a trash idea in hindsight." — Steve (18:04)

• On conflict and growth:

  "Businesses need conflict in order to grow, you need conflict, you need that tension." — Steve (45:02)

• On self-awareness:

  "Tricking yourself... can take you so far. And you just keep putting off the pain... Now you look up and there's no place to run and you're 52." — Steve (59:20)

• On truth and artistry:

  "It's the artists that are not that talented that want to be lied to. The best of the best want the truth." — Steve (47:40)

• On legacy and sacrifice:

  "I've taken so much of time away from my family. At least we could say, at least we have that to show for it." — Steve (69:36)

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Timestamps for Important Segments

• 02:00 – Steve on relationship-building as survival skill
• 04:58 – The power of seeing yourself reflected in culture
• 13:07 – His mother’s leap of faith in refinancing their house
• 15:01 – Being the bridge between hip hop and corporate America
• 17:12 – Inflection point: Will Smith, "Men in Black," and product placement
• 21:02 – Jay Z, Reebok, and changing perceptions
• 27:10 – The maniacal drive required for entrepreneurship
• 30:03 – Real mentorship isn’t transactional
• 34:52 – Critique of how “culture” is trivialized in business
• 36:58 – Removing personal taste: the key to cultural translation
• 43:43 – Challenge and respect: foundational leadership values
• 47:22 – The highest performers want honest feedback
• 54:47 – The myth and reality of work/life balance for entrepreneurs
• 65:16 – The compounding effect of saving and small habits
• 68:39 – On building a legacy and the cost of ambition
• 74:15 – Aspiring to balance peace and ambition
• 75:39 – Respect as a mutual expectation

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Final Takeaways

• Use your uniqueness as leverage, not a liability.
• Relationships and cultural translation are as important as raw talent or vision.
• Don’t chase validation or manufactured mentorship; emulate, observe, and ask questions in proximity to greatness.
• Truth—often uncomfortable—is essential for lasting leadership and creative partnership.
• Entrepreneurship is not for everyone: it demands obsession and tolerance for failure, and shortcuts seldom pay off in the long run.
• Legacy is built on service, sacrifice, and meaningful change, not simply profit.

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Much respect.

Transcript

[A]

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. This podcast is brought to you by Kleenex Lotion Tissues. For whatever happens next, grab Kleenex. Introducing the new Eggo protein waffles. The same great Eggo taste people know and love. Now with 20% of your daily protein in every serving, protein never tasted this good. These waffles deliver an excellent source of complete protein with 10 grams per serving and are made with wholesome ingredients fresh from the griddle. Perfect as part of a complete breakfast. Eggo Protein Waffles pair easily with fresh fruit, almond butter, or whatever is already in the kitchen. They offer a delicious way to start the day with irresistible taste families are looking for. When something tastes this good and delivers this much protein, no one can say no. Head to your local grocery store to fuel your morning with Eggo protein waffles and pancakes available at retailers nationwide. I'm so happy to have you here. Just to contextualize 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?

[B]

I was always curious about things I didn't know and understand. I never let industries that were new 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 capitalize 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 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 going to get the cool white CEO who wants to know, the cool young black person or Spanish, Latino, 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. 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. 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.

[A]

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? I think so many people feel like that.

[B]

I swear to you, Emma, I never felt trapped by that. I actually would tell you I feel more trapped now, and we could 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 gotta think about, whether it be Living Single or the Martin show or Will Smith and. 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 that looked like you and felt like you. And that was very important as 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 financial opportunity. Distribution, capitalization, those types of things that can help you do something. 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 look at my career and you could see who those people are. It's not like, hard to tell.

[A]

Did you study those guys before you knew him?

[B]

No. No. Study them?

[A]

No, because I do that. I do that all the time. I find out he has the tip at the top.

[B]

Here goes the study. Who's the CEO of Sony Music? Oh, that's Tommy Mottola. Oh. Who's the CEO of Interscope? Oh, that's Jimmy Iovine.

[A]

You knew them.

[B]

How I got to know them is a separate thing, 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 fractured information like it is today, where there's a thousand different options. It was five, 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.

[A]

I love that you say 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?

[B]

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

[A]

Well, you know, I asked you because I feel 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 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?

[B]

I was shocked that the writer got away with writing that headline. I couldn't believe that 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.

[A]

What were you. Were you. Do you feel embarrassed or what's the feeling? I want to understand.

[B]

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

[A]

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.

[B]

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

[A]

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

[B]

I wasn't surprised. And they got the picture right, too. The whole thing worked.

[A]

First of all, it was a great article, but it was very accurate, and it was.

[B]

I was very proud of it.

[A]

It was a great summary, I think, of your career. And, you know, when I think about you, 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?

[B]

I got a chance growing up in Queens in 1986 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 kango 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 a ball in a circle, I've seen LL Cool J. I seen it 16. Like, I seen that. Okay? I seen Rundy when rap took off. And specifically in my neighborhood, 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 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 Bismarckie performing in basements at a basement party. 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. 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 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 that 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. When it got to that stuff later, then I started to pull from those things. I didn't know that at the time.

[A]

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

[B]

I thought that I was gonna play sports, football. I thought I was gonna 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 gonna be the whole thing.

[A]

Where'd you get the money from to.

[B]

Invest in real estate? My mom let me. You know, my mother lent me money. She refinanced the house.

[A]

Oh, my God.

[B]

And I mean, she refinanced a house. My father was away, and he definitely didn't know. She refinanced the house. And I'm never gonna ask her how she got his signature. She refinanced the house and lent me money.

[A]

She must have had a lot of faith in you.

[B]

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.

[A]

Do you remember how much you made?

[B]

Yeah, I made $45,000.

[A]

That's a lot of money back then.

[B]

Yeah, I made $45,000 when I was 19.

[A]

And you paid your mom back?

[B]

I paid my mom back, and I got going.

[A]

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

[B]

I was probably doing the mortgages for, like, three years. Three and a half. Three, Three to 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.

[A]

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

[B]

Well, he was talking about what I had spoken about earlier, like being able to develop relationships when I was doing what I was doing. Honestly, Yes. I watched the Benny Medinas and the Quincy Jones and the God Bless the Clarence Avants 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. 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, then I'm going to 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. This is actually something that works in accord with what you are 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. Because 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.

[A]

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?

[B]

The easiest way to market would be Men in Black. And Men in Black was interesting from a standpoint that Will Smith's career as a musician had come to a hit. 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.

[A]

Yeah, right. So like, different vibe from where you came from.

[B]

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

[A]

Right. To the wider culture.

[B]

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

[A]

Were they happy being happy rappers, by the way?

[B]

No.

[A]

No.

[B]

You know what the funniest thing was? They both wanted to be the opposite. Yeah, course, they all wanted to be the other shit.

[A]

Die.

[B]

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 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 Four Men in Black. And Will Smith was so ice cold at that time. You think he's cold now? He was freezing back then.

[A]

Oh, he's cold now.

[B]

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 wanna be in the video.

[A]

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

[B]

They didn't wanna even be in the music video. His happiness and their credibility, they didn't want that to mix. So they wanted to check, but they didn't want the video.

[A]

So what does the unhappy, happy rapper do with himself when he gets successful? Yeah.

[B]

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 glasses that he wore in the movie, in the music videos took off. And when that moment took place, we at the record company were so successful. Cause we sold 10 million Will Smith albums. And we didn't expect that to happen. Obviously.

[A]

Fair.

[B]

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 not eating up the glasses. How could we? And you know what's funny is.

[A]

And you weren't getting paid off the glasses. No, the glasses were just in the movie. No one's getting paid.

[B]

How about this one?

[A]

What about Will?

[B]

Will got nothing. They were promoting. It was promotion. They paid the movie company something. And the movie company product placement, Baby Faces. 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 at that agency.

[A]

So you then start translation. The Agency. 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.

[B]

It's early. You know what? And every. There's. You can't watch a podcast without Jay Z's name coming up anymore.

[A]

But let's do it. Come on. Let's talk about Jay.

[B]

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 wrote a line. You wore a Reebok Vando. Now you wear Chanel sandals I made you. Why would I play you? I mean, he wrote those lines. I mean, they were, like, considered the worst. And Jay said, nah, we're gonna put escarner on these joints and we gonna go. And now listen.

[A]

Because he was getting a piece of that.

[B]

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

[A]

And he did.

[B]

And he did.

[A]

And he did.

[B]

Because they were all.

[A]

Everyone was wearing them.

[B]

That's the reason. That's what led to Yeezys.

[A]

That was the deal that changed again.

[B]

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

[A]

Early. It's early. That's what I'm saying. That's what I mean. I literally.

[B]

I'm saying that.

[A]

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

[B]

I'm not saying it because I'm up for. 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's taken. But I remember there was a time when there was no way you could get into alcohol.

[A]

Alcohol.

[B]

Are you crazy?

[A]

A million percent. Or soft drinks.

[B]

You know that Alcohol, soft drinks, clothing.

[A]

We were like, diageo, own it. Coca Cola, own it. Puerto Ricardo, own it.

[B]

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 most important thing is, are you an entrepreneur? And we should talk about that at some point. I want to talk about that.

[A]

Are you an entrepreneur? 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.

[B]

Everyone can start a business.

[A]

Everybody thinks they can.

[B]

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

[A]

Go on, tell me.

[B]

Everyone can't start a business. Well, they can start one well, that's all I'm talking about.

[A]

Go on, keep going.

[B]

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

[A]

That's it. You're just. Everyone can start one.

[B]

Period.

[A]

So what does it take? There's nothing I love more than hearing about people's side hustles. You can host your home on Airbnb while you're gone. And it's such a practical way to earn a little extra money without it feeling like a full time job. Just a few nights of hosting can help you cover travel costs or maybe even a nice meal on your next trip. It's simple, easy, and doesn't require constant attention. You just open up your space while you're away and let others enjoy it. So if you've got a trip coming up, whether it's for work or just to get away, hosting really does feel like a smart, practical choice. Seriously, your home might be worth more than you think. Find out how [e-mail] host you've probably heard. It isn't what you say, it's how you say it. And I've realized that that's true not just in life, but how you move through it. You need to set an example, take the lead, and adapt to whatever comes your way. That's why I love the Range Rover Sport. It's a car that matches that mindset, blending power, poise and performance. With its distinctly British design and exquisite interiors, it's immediately clear that this isn't just a car, it's a statement. Inside, you'll find innovations like the cabin air purification system and active noise cancellation, creating a level of comfort and control that feels effortless. And with seven terrain modes and a choice of powerful engines, including a plug in hybrid with an estimated range of 53 miles, the range Rover Sport balances raw power with refinement. It's dynamic, agile and truly instinctive, reflecting the way I like to drive and live. Build your Range Rover Sport@range Rover.com US Sport what is the difference between those that should, 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 doing 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?

[B]

One of 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]

A company in this country. Yes.

[B]

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 that was like, fuck off. They probably thought he was a failure and they didn't want to stop. But Travis will tell you that story. You got to 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'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. 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.

[A]

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.

[B]

It might not be worth it.

[A]

That means that you are constantly thinking about something.

[B]

You have no choice.

[A]

And you don't have a choice.

[B]

You have no choice because the rate.

[A]

Of failure is high.

[B]

The rate of failure. It doesn't make any sense. The math doesn't work. 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 know. I knew I couldn't go to college. I knew I didn't want to do that.

[A]

Well, you tried and you tried and you tried.

[B]

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

[A]

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

[B]

You're a West Indian parent. You're a West Indian man. You got to, like. Got it. You got. Definitely got to go to college.

[A]

Your parents got all the way here.

[B]

And you can't even make that. 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.

[A]

Okay, just pause there. Wait a minute. We're coming.

[B]

We are coming back.

[A]

We're coming back. Wait a minute.

[B]

We don't have a commercial.

[A]

Entrepreneur. We're coming back. Entrepreneur. Mentor. What's the other word?

[B]

Culture.

[A]

Culture. Okay, we're coming back. Go back to the mental bit. Why is it crazy that people run around for a mental.

[B]

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

[A]

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

[B]

Because I've never heard of that shit before somebody chose you, somebody found something in you and decided without saying it publicly that they were going to 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?

[A]

Yes.

[B]

Yes, I am your mentor.

[A]

You are anointed. Yes.

[B]

I don't even 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.

[A]

But tell me, you know why people are looking for mentors. So what do you tell them? I have a pretty, like, my thing. 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.

[B]

Ask me a fucking question, can you be my mentor? Please?

[A]

Have a. Till the time. So what do you tell people that are looking for a mentor?

[B]

When people. 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 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 or at least the acknowledgment of such. 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.

[A]

Yes. That's why I asked you if you studied these guys. Because I feel like when you. When you.

[B]

I studied Quincy, Clarence.

[A]

Of course you did.

[B]

I studied Clincy.

[A]

Because you wanted one generation.

[B]

I thought you were asking me, was I studying the guys. I was, yeah.

[A]

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, yeah, I was.

[B]

Studying Russell Simmons, Clarence Avon, Quincy, Quincy Jones. There was a guy who started. Who took over Beatrice Foods, Lewis guy, he happened to pass away. Reginald Lewis, I believe his name was. He had wrote a book, why Do White Guys have All the Fun? Should definitely read that book. He was like the first black guy that was doing it gigantically on Wall Street. But I would read about these guys, these gentlemen, and I would be constantly inspired by what they were doing and Even like Russell Simmons back in the day, you pull it from everywhere. 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 a panther on.

[A]

A Rolls Royce choice.

[B]

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 Bitches 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.

[A]

But it's like self mentoring. You're looking at these people, and I'm.

[B]

Taking 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 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 could walk up to somebody and be like, can you be my mentor? Is so fucking fake. Like, you can't just microwave a fucking mentor, man. There's no. It's not like a popcorn button. Like, people are crazy with this bullshit.

[A]

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. With the idea of mentorship. And you're right. You can't manufacture, like, why you're not mentoring me.

[B]

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

[A]

Well, that's why I've got you here, because you've got so many things to say. I know you're not talking to me, Steve. I know you got time to shut up on my own podcast later, maybe. 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?

[B]

Yeah, because what happened is it's turned into this ketchup. You could put it on anything, like culture, culture, culture. And sometimes it's specifically meant to talk about black culture. I wrote a book, the Tanning of America.

[A]

I read it. You told me that New York Times bestseller was fabulous.

[B]

Thank you. 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? It's important. And I'm like, that word is so very acute at understanding a group of people and what those people share. 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 that when you used to play around with that word. Fuck around with that some more. I feel like I got you. I'm in your hands.

[A]

Complete dumb.

[B]

I'm on. You're like, he's just in my brain.

[A]

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?

[B]

I'm gonna tell you the first thing what I said about. 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 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. Yes, that's my job. Whether I like the dance or like the clothing style or like the word or whatever is really not my perspective. In fact, 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. Yes, right. And that's how I feel about things. Young people are gonna shape and define culture. That's what's gonna happen. It's happened with my generation. It happened to your generation. It's gonna happen with the next generation. We're never gonna put Jack back in the box. That's what's gonna 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.

[A]

Removing your opinion.

[B]

Removing my opinion.

[A]

So you don't got to like it, you just got to understand it.

[B]

All I got to do is understand it and facilitate and hire. Well, 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, you're in trouble. You might as well just close the door, give him back the key, and go home.

[A]

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

[B]

For some people, it depends on where you are, on your cycle of an entrepreneur. Some people I just said that to may think I'm bugging where you are. You're like, shit, I get what the fuck he's saying.

[A]

No, I fully get what you're saying.

[B]

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

[A]

You know those weeks where everyone in the house catches something? One kid brings home the sniffles from school, and before you know it, the whole family's down for the count. As a working mom, that's my cold and flu season. Reality juggling deadlines, school drop offs, and a mountain of tissues. And I'll be honest, those days can get mess. There's the constant chorus of, mom, I need a tissue, or worse. Catching my youngest just, like, wiping her nose on her sleeve. I'm like, darling, please, no. That's what Kleenex lotion tissues are for. And that's when I realized how something so small can make such a big difference. Because Kleenex lotion tissues don't just get the job done, they get the job done. While being so gentle. When everyone's noses are red and raw from constant wiping, these tissues actually help soothe and protect with ingredients like coconut oil and aloe. They're like a little moment of care, soft, moisturizing and so much better than grabbing a paper towel or whatever napkins nearby. And honestly, Kleenex has become a staple around our house. Not just for the sniffles. We use them for wiping little tears after a scraped knee, or even happy tears when we're all laughing at something ridiculous together. That's what I love. Kleenex lotion tissues are kind of like that quiet little helper in the background. They make those messy tender moments a little softer. Literally, so it doesn't matter if you're catching a cold or if you just need something that's kind to your skin. Kleenex lotion tissues have you covered. They're made with skin loving ingredients coconut oil and aloe for three in one benefits that help protect, soothe and moisturize. Because let's face it, life as a parent doesn't always go as planned. But when you have Kleenex, you're ready to face whatever comes next, from sniffles to surprises. You can't predict sick days, but with Kleenex lotion tissues, you can be prepared for them for whatever happens next. Grab Kleenex. Today's segment is brought to you by Bumble, the Go to Dating app for finding love. You all know that I'm a big believer in building things that last in business, in family, but especially in relationships. And the truth is, dating can feel totally overwhelming. That's why I've noticed so many of my friends and people in my circle turning to Bumble. They've been listening to their community and making changes that actually build trust. Bumble is now photo and phone verified, so you know you're actually talking to someone real. And with optional ID verification, you've got the added reassurance that their photos and their age are real turns too. So no catfish here. I keep hearing the same perspective. Bumble just feels more intentional now. Profiles highlight the things that you have in common right away, so it's easier to see if someone aligns with what actually matters to you. And I love that they've added the Dating Advice hub in the app. It's like having a dating expert in your pocket. It's a reminder that dating doesn't have to feel overwhelming. You can take your time. You can laugh at yourself and focus on what feels right for you. So if you've been thinking about the idea of finding love Maybe, just maybe, this is your sign. Bumble's making dating safer, more intentional, and honestly, so much more fun. And isn't that the whole point? Start your love story on Bumble. I really want to talk to you about leadership style because I feel like this is something that kind of 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, like, 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 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.

[B]

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

[A]

Thanks, dear.

[B]

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 the truth. Challenge and respect is one of these things where we have to be able to have a disagreement and get to the other side without you ever feeling disrespected in that process. And that's very hard to do, very hard to cultivate. 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.

[A]

Sorry, from what to four?

[B]

From three to four.

[A]

From three to four.

[B]

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

[A]

Don't get me started.

[B]

People don't have confrontation on Zooms.

[A]

Nothing good ever happened on a Zoom.

[B]

Well, that's not true either.

[A]

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.

[B]

They probably came up with Zoom on a conference call.

[A]

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

[B]

Okay, fair. But if you don't deal with conflict and confrontation, people in general do not like conflict.

[A]

Yeah.

[B]

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 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 and that's usually the CEO. Because they don't have a place to hide.

[A]

Yes.

[B]

The chief marketing officer. A lot of times they could do that.

[A]

Exactly.

[B]

The CEO, the cfo. When you start getting into that realm of the company more fact based, they can handle the truth. Well, CMOs and performance marketing companies have to handle the truth as well. So I don't want to 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. Because I'm not talking to, I'm talking to the company. Right. So it's like if it's me and you, we work at a company, we're employees or whatever, and 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 within the company that can hear the truth because you need that person to do something and distribute that fact within the organization. So finding the person is probably the biggest job in corporate America. There was a second question you asked me today.

[A]

Well, I want to understand, like, how do I. 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.

[B]

Find it when you remove yourself? A lot of 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 artist 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.

[A]

You know, I think the best people always want.

[B]

It's the craziest thing I think I.

[A]

Learned that employees, the best employees want the truth. The best husbands and wives want the truth.

[B]

I just saying it, it'd be leaving my mouth. And I'm like, shit, I hope it's going to be like. And they're like, yo, I really respect you. I'm like, oh, shit. Word. I want you around more.

[A]

Yes.

[B]

If you can tell an artist or any creative the unvarnished truth with a rational fact behind it, 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 not a hard take. But really, 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 just giving it from the heart. You can develop long lasting friendships that way.

[A]

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?

[B]

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 that had this room bubbling because.

[A]

They tell me you probably got word.

[B]

That Steve is bubbling out.

[A]

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

[B]

Yeah, they cut the air conditioner.

[A]

Let's go this guy down.

[B]

The challenge and respect thing, I'm not there yet. And I'm dealing with something that you asked me. Did you feel trapped earlier 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 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 because 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.

[A]

For you, 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. You can get on board or you can go. And I feel like it's very, very clear.

[B]

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 the company that I'm building. Like, you can go into people's house. 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. It's like everybody has their own version of the culture of their household. That may not work for your household, but it works well in that household.

[A]

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.

[B]

I'm going to talk about my company and then I'll talk about the industry.

[A]

Yeah. So, fine, I'll let you do that.

[B]

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 in 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, or gender. 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. They may want to softer tone or they may want 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 of women that I've met in the industry is that I haven't seen much different from them than men. So one of my very good friends is Thasunda, that's the CEO of Thasunda docket. Thasunda Duckett. Right, Right. If you speak to Tasunda, 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 got to get to the top. And that sounds like a lot of men that I know and it has that same kind of energy. But whether it be kellen 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 that they want. As a man, are they softer?

[A]

Nah.

[B]

No.

[A]

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 someone right now.

[B]

As an entrepreneur, I don't think that you have the luxury of coming up with that idea. That's just like 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, their college tuition at risk. So I'm like, you have to afford work life balance. If you're the CEO of an entrepreneurial organization 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've 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 do that.

[A]

No, you actually would.

[B]

I would do that.

[A]

Like you would psycho. You actually would do. What are you doing? What are you doing?

[B]

What the fuck is you doing right now?

[A]

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.

[B]

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

[A]

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

[B]

I have no idea.

[A]

I'm 42.

[B]

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

[A]

But it's a mentality.

[B]

You know how we sound. But you know how we sound.

[A]

We sound old as fuck. You sound like the people like whining about rock and roll or something terrible.

[B]

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

[A]

Well, you are. You're officially in your early 40s 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.

[B]

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

[A]

Well, that is, 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. 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, whatever, 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.

[B]

Again, listen, I agree with everything that you're saying and 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 mean, right? It's an attitude, it's a mindset that's required to win, that if you're not all in on that, then you're just not going to win. I don't give a fuck what it is. If there's any wisdom I could provide, being somebody who's been doing this for a while is that I've never seen anybody win long term with shortcuts. And finding out that you're not successful and that your idea didn't work really late in life is terrible. Like tricking yourself. I used to call it the Ponzi scheme of lying to yourself. 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-50s?

[A]

Fuck that.

[B]

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 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. And I'm not saying forget about it.

[A]

I'm like, I could never.

[B]

You could never.

[A]

I could never. Yeah, I could never. You know, one thing that's never changed in business is the need to stay close to your customers. Today that means being everywhere they are on Instagram, TikTok or wherever the conversation is happening. With Shopify, I can do exactly that. Their integrations make it easy to connect with audiences in real time, creating loyalty and trust that lasts. I love that you don't need a full tech team to make it happen. Shopify brings everything, everything together. Online sales, pop ups, social channels so that I can manage it all in one place. And whether it's an emerging brand or a household name like Skims or Good American, Shopify powers it all, making it simple to scale while staying authentic. Plus their AI tools like Shopify Magic feel like having a team in your back pocket, helping write product descriptions, plan content, track trends, all without the chaos. If you want to meet your customers exactly where they are and grow your brand with ease, Shopify makes it seamless. Ready to build your own empire? Head to shopify.com aspire and get started today. I've always been inspired by women entrepreneurs, especially those who aren't just building businesses but are changing the game. That's why I love saie. It's a woman owned clean makeup brand that's all about high performance formulas that actually improve your skin over time. For me, the glowy super gel is a must have. It's lightweight, it doesn't clog your pores, and it gives me that effortless lip from within. Glow. My go to step for a no makeup makeup look. On days I want a little bit more coverage. I reach for the Slip Tint tinted moisturizer with SPF 35. It's sheer, dewy and packed with hydrating, nourishing ingredients so my skin looks radiant while being protected. And the Dew blush? It blends like a dream, giving a beautiful buildable wash of color that's never streaky or patchy. SA makes beauty feel easy, chic and intentional. A brand that truly reflects the vision and drive of the woman behind it. Find [e-mail] and every Sephora store across the United States and Canada [e-mail] I want to ask you this question. Is there a Is there a leadership lesson or A lesson more generally in business that you've learned the hard way.

[B]

Yeah. Sell externally, not internally.

[A]

Don't, please expand.

[B]

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 it. 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, nothing inflated.

[A]

When have you done this? Give me an example.

[B]

Believing in an idea longer.

[A]

Yeah.

[B]

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. Yeah.

[A]

Fair. No. That makes total, total sense.

[B]

You've done it.

[A]

I might still be doing it. 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.

[B]

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

[A]

No, you were not.

[B]

Yeah. By the way. Through different business managers and all kinds of shit, there was still this thing.

[A]

There's 200 bucks going.

[B]

It was $200 going out every month.

[A]

That's amazing.

[B]

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, 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.

[A]

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?

[B]

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

[A]

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

[B]

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

[A]

Well, I heard that you only sleep like four or five hours.

[B]

Yeah, that's psycho. I'm not happy about that.

[A]

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

[B]

I'm not happy about that. I'm just saying that sounds like some. I travel way too much and I don't sleep enough.

[A]

Are you not a good sleeper or what is the thing? You don't need a lot of sleep or you've just got so much happening and so much going on, I don't even know anyone. Oh no, you gotta change that quite. You're too old for that.

[B]

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

[A]

I actually don't think that's surprising.

[B]

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

[A]

Who doesn't like sleeping?

[B]

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

[A]

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?

[B]

Hell no.

[A]

No. You're not a meditate.

[B]

Shut up. That sounds like, sounds like, that sounds like a zoom.

[A]

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?

[B]

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

[A]

I met her.

[B]

Yeah. And she is at Columbia University.

[A]

Are you so proud when you say that?

[B]

I'm very proud of her.

[A]

You should be.

[B]

She's really smart. My legacy, it's important to me that have a son Pharaoh, and a daughter, Phoenix. I want my children obviously to be something, to do something and continue to do things that they're proud of. It's important to me that my contribution to hip hop and 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 that relationship. 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 one day and go like, man, something changed that I was there 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.

[A]

Yeah.

[B]

At least we could say, at least we have that to show for it. I could have done well financially without taking that much time away from my family.

[A]

It's very lovely that you say we.

[B]

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

[A]

Going to change the game, to change the game.

[B]

And 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.

[A]

Crazy.

[B]

There were none. Crazy like a black girl would go in a Sephora nothing and start scratching her head looking for some fucking shampoo, right? Yeah.

[A]

She was walking out with nothing.

[B]

She was walking out with nothing.

[A]

All the wrong products.

[B]

It was like. I remember thinking, like, how do you go. I 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. The condition is fucked up.

[A]

You really got this shit through. You really, really did. You wait till Carnival Cruiser.

[B]

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 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've gone at it with that level of thought, and they've all had varying degrees of success, but that was the level of thought that was into each one of those things.

[A]

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? Who.

[B]

Who's killing it right now? It is killing it. You guys are killing it.

[A]

Thank you.

[B]

The team at skims is killing it. Who's killing it right now? There's about to be a whole nother new opportunity with all these streamers.

[A]

Oh, I know.

[B]

Yeah, the streamers. But who's killing it right now? Fuck. I would say. Damn it. I don't want it to sound like that because you right here.

[A]

It's okay. Go ahead.

[B]

Shit.

[A]

I mean, I don't know.

[B]

You guys are.

[A]

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

[B]

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

[A]

No, I don't see it as culture. Is it?

[B]

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

[A]

We're still all figuring it out.

[B]

Yeah, we're still figuring it out.

[A]

It's too early, but I'M saying, but 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 Travis.

[B]

Travis Scott is killing it.

[A]

Travis. Yeah, yeah.

[B]

Travis Scott is killing it. Pharrell is killing it. You guys are killing it.

[A]

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

[B]

I never fuck with the name. I haven't seen the rebrand.

[A]

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

[B]

Risk and audience.

[A]

Yeah, yeah.

[B]

When you have nothing to lose, I think you should go for it. When you have nothing to lose like that, I think 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.

[A]

First thing you do when you wake up cold plunge. Oh, you're a cold plunger.

[B]

You can't tell by my skin. It's not working. What are you talking about?

[A]

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

[B]

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

[A]

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

[B]

Oh, man. I really want to 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.

[A]

Oof. We need another podcast now. Right at the end, you say that.

[B]

You asked me that question.

[A]

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

[B]

The Greatest salesman in the world.

[A]

What is something that you valued when you were starting out that you no.

[B]

Longer value acceptance from others, the acceptance of others. Like, hey, you know, I like Steve. All that bullshit. People, like, whatever the fuck they look at what's going on right now in the world, they just run around liking whoever's popular at the moment. Fuck them. But, like, 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. How about that part? How about that part? Actually?

[A]

Yeah, fair enough. You end your emails with much respect, which I think is such a beautiful way to sign up an email. What does respect mean to you?

[B]

I respect your time. I respect your perspective. 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 feeling towards the way we hold one another, the regard we have for one another. 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 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. There is no respect unless it's mutual respect. There's no way I can respect you if you don't respect me. That doesn't work, you know, so the idea of much respect for everybody, it doesn't have to. 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 want people to know. That's sort of where I'm at with it.

[A]

Yeah, 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.

[B]

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

[A]

Thank you so much, Steve. Love you today.

[B]

Thanks.

[A]

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 who'd be so grateful. Aspire with Emma Greed is presented by Audacy. I'm your host, Emma Greed. Our executive producers are Corrine Gifts, Gilliatt Fisher, Derek Brown and me. Our executive producers from Audacy are Maddy Sprung Keyser, Leah Reese, Dennis, Asha Salouja 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, Kirk Courtney, Andrew Steele, Carlos Delgado and Ani August. Social media by Olivia Homan. Special thanks to Brittany Smith, Sydney Ford. My teams at the lead company and WME Maura Curran, Josephina Francis, Hilary Schuff, Eric Donnelly, Kate Hutchinson, Rose, Tim Meekol, Sean Cherry, and Lauren Vieira. If you have questions for me, you can DM me at Aspire with Emma Greed Greed is spelled G R E D e. That's Aspire A S P I R e with Emma Greed. Or you can submit a question to me on my website emagreed me. Look, we get it. You can hardly go anywhere or do anything these days without hearing AI this or AI that. And if you're like most people when it comes to AI, you're impressed but have a few concerns. But what if AI was used not as a tool to replace people, but as a way to help understand people better? AI from SurveyMonkey is designed to do just that. From crafting the perfect survey, which is harder than you might think to analysis that digs deep, finds patterns and surfaces trends quickly. SurveyMonkey's powerful suite of AI capabilities makes it faster and easier than ever before to get insight from real people, helping you make confident decisions for your business. Try it [e-mail] Emma.