Puff: A Billionaire's Story

August 11, 2023 is the 50th anniversary of hip-hop. What started out mostly as a spoken word artform has become a worldwide juggernaut. Thanks to the moguls who pushed the genre forward, hip-hop went from 0 to 100.

In this episode, we rank the 50 greatest moguls in hip-hop’s history. We reached out to industry experts — from artists to execs to media personalities — to help us compile the list. Friend of the pod, Zack O’Malley Greenburg, joins me to count them down from No. 50 to No. 1

0:39 How do we define “mogul”

7:06 Honorable mentions

09:10 The “Don’t overlook their influence” group (ranks 50-41)

16:19 The “Playing chess not checkers” group (ranks 40-31)

23:38 The “Our impact runs deep” group (ranks 30-21)

33:47 No. 20

35:37 No. 19

37:56 No. 18

41:32 No. 17

44:27 No. 16

47:21 No. 15

51:22 No. 14 

55:55 No. 13

59:09 No. 12

1:00:46 No. 11

1:02:16 No. 10

1:04:39 No. 9

1:06:44 No. 8

1:10:20 No. 7

1:14:06 No. 6

1:15:37 No. 5

1:17:11 No. 4

1:20:53 No. 3

1:29:06 No. 2

1:30:34 No. 1

1:33:22 Who got snubbed?

1:35:42 What trends stick out from the list?

1:41:21 Who would you pick to run your empire?

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Host: Dan Runcie, @RuncieDan, trapital.co

Guests: Zack O’Malley Greenburg, @zogblog

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TRANSCRIPT

[00:00:00] Zack Greenburg: ownership. Was just such an important thing for Nipsey. Such an important thing for Berner. And, you know, interviewing the two of them, I would say, their mindset around ownership was the closest I've ever seen to Jay Z.

[00:00:13] Dan Runcie Intro Audio: Hey, welcome to the Trapital Podcast. I'm your host and the founder of Trapital, Dan Runcie. This podcast is your place to gain insights from the executives in music, media, entertainment, and more who are taking hip hop culture to the next level.

[00:00:39] Dan Runcie Guest Intro: This episode is a celebration to hip hop's 50th anniversary. This is a countdown on the 50 greatest moguls ever in hip hop. I'm joined by Zack O'Malley Greenburg, friend of the pod, and we both reached out to. A bunch of label heads, executives, people in hip hop that would know best. And we put it together in an aggregate list.

And we're here to break down that list today. We talk about what does it mean to be a mogul? What are some of the considerations we made when we were looking into this list ourselves, how the results looked, what surprised us? What were the snubs? What were the misses? And what can we learn from this overall?

And if Zack and I were putting together our dream teams, what would that look like? This is a lot of fun. Really happy with how it turned out. So let's dive in.

[00:01:25] Dan Runcie: All right, hip hop's 50th anniversary is right around the corner and we decided to celebrate it in the only way that we know best countdown hip hop's greatest moguls and I'm joined by Zack O'malley Greenburg, who reached out to me about this. I was really excited about it and we spent some time over the past couple of weeks, reaching out to people we know, making sure that we have the best insights looking through and making sure that we had all of the. Breakdowns to share. So Zack, I'm ready for this. How are you feeling?

[00:01:55] Zack Greenburg: I am stoked. Yeah, I mean, you know, 50th anniversary of hip hop. We reached out to 50 different judges. amongst, you know, the sort of, the most respected folks from, you know, label heads to artists to entrepreneurs, you know, I think we've got half of them, roughly half of them replied since in their votes, we're going to keep their individual votes anonymous, but, you know, Dan could tell you about some of the judges.

Yeah, and it was just really fun to kind of mix it up, you know, I think the thing about this list, a lot of these characters are just kind of an apples to oranges comparison as you'll see once we dive into it, but that's the beauty of it, right? I mean, how do you, you know, compare like a pioneering executive to like a modern day artist mogul? And we really kind of left it in the hands of the judges. And we just said, basically the only guidance was, this is a business focused list, but you know, you can rank artists, executives, people who are both. It just, whatever your definition of mogul is, that's how, you know, that's how you should rank them. And people submitted lists and obviously the higher they rank somebody, the more points we gave them and, you know, the lower they got, but, you know, so there's some people on there who are like accumulators. They ended up on everybody's list, but not so high, but, you know, as a result, they ended up on the top 50.

And then there are some who were just like, not ranked at all by most people, but had a couple of really high ranks so that they made the list. So I think it's a pretty cool mix.

[00:03:10] Dan Runcie: Right? It's kind of like how we look at artists. There's some artists that have just been consistent, steady through and through each year. You'll always get some reliable output from them, but then there are other artists too. They were the best for a certain amount of time. Maybe they cooled off for a bit.

Maybe they came back and that's kind of the way music is too. One of the things that. I was asked whenever I was reaching out to people about this was the same thing that you posed earlier. People wanted to know, how are we defining mogul and we left it up to their interpretation. It is a term that means different things to different people, but maybe for the sake of this conversation, let's kick it off here.

Zack, how do you define mogul? And how did you define it when creating your list?

[00:03:51] Zack Greenburg: Yeah, I mean, to me a hip hop mogul, more general is just, you know, somebody who not only is a business person, but has some degree of ownership, in whatever it is that they're doing. that's not the only definition of it for me, but like, you know, when I was putting together my rankings, I thought, you know, who are the owners?

the same time, you know, people who are executives who are in a decision making place. you know, that counts for something. And I think also, you know, if you're an artist, and you simply have some control over your own work, you maintain your copyrights, whatever, like that counts as being a mogul.

 So, you know, specifically when it comes to hip hop, you know, I'd say people who are, you know, definitely getting in charge of your own work, but also creating new lines of business, you know, influencing the culture. but you know, a way that they've got some skin in the game from a business perspective, you know, that, kind of thing.

That's kind of how I looked at it. but you could see from the votes that, you know, everybody had a slightly different definition too.

[00:04:47] Dan Runcie: Yeah, there was definitely a lot of correlation with the artists who tend to be the ones that are the wealthiest. They end up at the highest rankings in on some of those lists, too, but it wasn't exactly correlated because there's a difference. And these are some of the things I kept in mind, too, with the mogul definition, thinking specifically about

influence and impact, were you having, or did you create opportunities for others around you? Were you able to be a bit of a kingmaker or queenmaker in your respective right? Was there a impact in terms of other generations that either looked and modeled how they're doing what they're doing and looking at you as some form of inspiration with that?

So there's the indirect impact and influence, but also the, Indirect piece of it too. So there's the money piece as well, but then what do you do with that money? And then that's how I had went about it. And similarly, everyone had their own unique spin to it.

[00:05:42] Zack Greenburg: Yeah, for sure. And, you know, and I think the definition changed over time, of what a mogul really is, but when I was putting my rankings together, I think the idea of starting something new, you know, that's also paramount, amongst all the criteria as well.

[00:05:55] Dan Runcie: Right? So, of course, Zack and I had our list, but we reached out to a number of people and several other label heads, executives, and people that are in the game.

So thank you all to your contributions. We couldn't have done this without you. And if anything, it helped add a variety beyond just you and I, getting and putting our list out there. It added a more full scope and like anything. Oh, this is how you look at it. Interesting and being able to pull unique insights there.

[00:06:21] Zack Greenburg: Yeah, for sure. you know, one thing I think we probably ought to point out, on the list, you know, the list is, heavily male. but it's about only 20% women on the list. you know, we did everything we could obviously to make it more equitable, but, you know, the votes are the votes.

And, you know, I think there is a bit of a reflection of sort of the state of affairs over the past half century, you know, unfortunately, like many parts of music business, hip hop has been, you know, heavily overindexing for males. So, you know, here's hoping that when 50 years to do a hundred years of hip hop, you know, we'll have even things out a bit or completely, let's say maybe even, you know, made up for lost time, but I think some of the spots on the list, you know, the rankings do kind of reflect an industry reality that we've seen, unfortunately for 50 years.

[00:07:06] Dan Runcie: Right? And hopefully this gets better. We do feel and you'll see when we talk about some of the people here, glad about some of the names that got mentioned. Of course, there's always room to be able to have more and hopefully for hip hop's 100th anniversary. If when and people are breaking that down, there's hopefully even more representation there.

So, with that, I think it's probably good for us to get started right before the list, but talk about some of the honorable mentions. So, there were people that didn't quite make the cut of 50, but we still wanted to highlight them and the work that they. Did here. So a few of those names here to give a shout out to.

So we have Cindy Campbell, Jermaine Dupree, Audrey Harrell, Jay Cole, Damon John. What comes or what do you think about when you hear those names?

[00:07:55] Zack Greenburg: Yeah, you know, I mean, Cindy Campbell, I think in many ways you could look at her as the first promoter in hip hop history, right? I mean, you know, we're talking about 50 years of hip hop. That's 50 years from that first party that. She and DJ Kool Herc through, you know, in the rec room on Cedric Avenue.

And, I think the idea was that they were going to raise a little bit of cash so she could go get herself a new back to school wardrobe. Now, if that's not, you know, entrepreneurship and hip hop, you know, from the very beginning, I don't know what it is. And so I think Cindy deserves a ton of credit, for being there at the very beginning, you know, but I think on the honorable mentions to a lot of the folks that are on here, you know, or maybe like a little bit, you know, not exactly falling on the same radar, you know, for the list. So like, you know, Damon John, obviously he did with, you know, creating FUBU and, you know, everything he's done as an entrepreneur, it's incredible, but it, I think it's sort of like more of a national brand that is, you know, apart from hip hop and so is his personality, right? Like you see him on shark tank or, you know, whatever, like he sort of moved past, I wouldn't necessarily categorize him, as just hip hop, although he's had a tremendous impact on hip hop.

So I think probably that's why, he wasn't on more lists. It's not to sort of ding him his impact, which is considerable.

[00:09:10] Dan Runcie: Right, and I do think that of course, music is one element of hip hop. You do have fashion, you do have others. So music definitely got weighted heavily in this list, but Dave and John and his influence in fashion, and there's other people in fashion and we'll get into them in this list too, but we can't overlook everything he did there and some of the more unique and clever marketing tactics that came from food booth that other people did who will mention in this list as well. 1 person that I do want to highlight here from that list 2 people. So, Jermaine Dupri want to give him a shout out as well. Just everything he was able to do with.

So, so Def records. He was part of that movement in the 90s, where you saw LaFace and then all these other groups in the South be able to come up, do their own. There was a so so deaf sound, a so so Def vibe and his ability to do it both in rap, but also have a bit of the soul there. Some of the epic production that he's been involved with, even outside of hip hop, thinking about albums like Mariah Carey's Emancipation of Mimi and others, even though he didn't always do everything in hip hop. I think that some of his influence can't go overstated there. And then the second person who's similar in that regard, I would say is Andre Harrell. We talked about him in past episodes, especially the bad boy one, but everything that he did from Uptown Records and then moving on to Motown Records and gave in many ways helped give Puff the blueprint for what he was able to do years later.

[00:10:37] Zack Greenburg: Yeah, absolutely. And, you know, I think Andre had a lot of successes, also had a lot of failures, not necessarily, you know, through his own doing, the time, but definitely somebody who deserves, you know, a hat tip at the very least. And, you know, I'm sure Puff would agree about that too.

[00:10:52] Dan Runcie: Agreed. Agreed. All right. We ready ready to get into it.

[00:10:57] Zack Greenburg: Let's do it.

[00:10:58] Dan Runcie: All right. So in the initial group here, which we're calling the don't overlook their influence group. This is people who are ranked 50 through 41. so in order we have Ethiopia have to Marion at 50. She was the former CEO of Motown. We have Top Dog, co founder and CEO of Top Dog Entertainment. We have Mona Scott Young from her work at Violators and more recently Love Hip Hop. And what she also has done with Hip Hop Homicides and some other multimedia projects. We have T.I. with everything he's done with Grand Hustle and Multimedia. We have Eazy E with Priority Records. Many ways pioneering so much of the stuff we saw.

We have Todd Moskowitz, L. A. Reed, Craig Kalman, former CEO from Atlantic. We have Sylvia Roan and then tied for 40. We have Desiree Perez and Steve Stout. What are your thoughts on that group list?

[00:11:55] Zack Greenburg: Oh, man, I don't know. Maybe we should just pick out a few here and there that we thought were particularly interesting. I mean, you know, I think Ethiopia is a good example of somebody who would be higher up if she were identified, you know, solely as a, you know, as a hip hop mogul, but she's had kind of like a pretty wide reach, you know, especially in R and B, and pop. I mean, some of the stuff she's done with Erykah Badu, NeYo, Stevie Wonder, you know, like over the years, you know, wouldn't be classified as hip hop, but it's worth it nonetheless. just think that, you know, being kind of like in between, in between genres, you know, resulted in her being down a little bit further on the list.

But, you know, somebody who had a tremendous impact. you know, I would also, I would highlight TI here, you know, the self proclaimed King of the South, but, you know, in terms of, I remember the years when, you know, we were putting together the Forbes list and, you know, kind of looking at, you know, kind of regionally who is most important to me.

Yeah, he was sort of like. The Jay Z of the South. And he was really, especially when he was having that moment, you know, getting a lot of songs on, you know, national radio and, kind of being in the public eye, I mean, had a tremendous business focus, you know, he was always interested in sort of like, what's the next thing that I can create?

and you know, that kind of entrepreneurial energy, you know, I think, especially within the context of the South, like taking the blueprint, from guys like Jay Z, you know, I think he certainly deserves a mention. I kind of thought he'd end up higher here, but I guess he's been, not as, especially in the music front lately.

and then I would definitely highlight, Desiree, you know, she's somebody who's been behind the scenes for a really long time, with Jay Z and rock nation, but like. she runs rock nation. And although Jay Z obviously has the final say in things, you know, a lot of things that you see, come out of that camp are, you know, her doing and have her fingerprints all over them.

And I know some of y'all might have seen the Book of Hove exhibit at the Brooklyn Museum or the Brooklyn Public Library that was a Desiree Perez production and, you know, she said that it was like her emptying her 80, 000 square foot storage unit into the library, but, you know, but to have, you know, that kind of, impact at a place like Roc Nation and to help, you know, Jay Z do what he's done, you know, I think those are all worthy, of notation and, you know, I think she deserves her spot there for sure.

[00:14:09] Dan Runcie: Yeah, Desiree is someone that has been working with Jay Z for a while now, and I feel like she deserved a shout out on Jay's verse in Pound Cake, the Drake song. You know where he's like, Dave made millions, Lyor made millions. I feel like Desiree should have gotten a shout out there too, but yeah.

I'm glad that she got mentioned here. Two other names I'll run through quickly. Steve Stout, someone who I thought would have ended up higher, and I know that, you know, it was interesting to see how the results played out, but I do think that one of the best marketers that we've seen come through hip hop.

He was ahead of the curve in a number of ways, dating back to the 90s with seeing the men in black sunglasses and everything that he's done there from his time working with Nas, everything that they've done, whether it was the firm or, him being a record executive himself and then showing as well, how he's able to do it in advertising and bringing a lot of these companies and brands that didn't necessarily align or think about being related with, you know, hip hop culture and those elements to be able to do it.

You look at a company like State Farm and how we now look at what that company has done. And a lot of that is through his work and obviously with what he's done at United Masters. So shout out there and I also do want to give a shout out to Mona Scott Young mentioned her earlier, but she was a right hand to someone who will mention on the list as well coming up soon with everything she did in Violator, this is back when, you know, Q Tip and Busta Rhymes and that whole crew were doing their thing. And then later, I know people have a lot of polarizing opinions about love and hip hop, but if you look at the career opportunities that were created for people that have came through, and the longevity that she's granted, a lot of people that the record industry forgot about that she was able to continue to give opportunities for think about the trick daddies, Trina's and folks like that. I know people hate to see them arguing on camera, but would we have Cardi B where she is today? If it weren't for the platform of love and hip hop, and she's continued to do things with other vocals on the list that we'll get into. So I do want to give a shout out to her

[00:16:08] Zack Greenburg: Yeah, definitely a worthy shout out. And we could probably go on and on about even just like the tent in this bracket here, but I suppose we ought to, we ought to move on to the next room before, before we run

[00:16:19] Dan Runcie: indeed. Yep. So the next group is playing chest, not checkers. So at 39, we have Dave Mays, founder of the source 38. We have Irv Gotti, founder of Murder, Inc. 37, Cardi B 36, Lil Wayne 35, Nipsey Hussle, 34. Steve Rifkin, from Loud Records 33, Missy Elliot. 32 Birder from Cookies, 31 Kevin Lyles and 30 Chris Lighty.

[00:16:47] Zack Greenburg: Oh man, this is a pretty stacked bracket, I must say. I think that, you know, there are a couple of names that stick out to me here. I'm going to go with Nipsey and Berner, because in a funny way, I think, they have like a sort of a similar, a sort of similar strategy, which is like, you have a very clear idea of what it is that you're going to do.

You own it, and then you, you know, you continue to own it like ownership. Was just such an important thing for Nipsey. Such an important thing for Berner. And, you know, interviewing the two of them, I would say, their mindset around ownership was the closest I've ever seen to Jay Z. and they really understood from the beginning that they had to own all their music.

Own all of their branding own, you know, the companies that create on the side and then they can monetize it later. And, you know, with Nipsey rest in peace. I mean, he was just on the cusp of, of kind of like becoming a mainstream superstar, you know, when, his life ended all too soon. So, I think what Berner is doing with cookies is really fascinating like Berner is, you know, you want to talk, lists. I mean, he's in the top five, probably the top four or three at this point, in terms of net worth for actual, hip hop artists. And that's because of the success of cookies and, you know, there's been, a lot of ups and downs in the cannabis business lately, but like the amount of ownership that he has, you know, I think it amounts to about one third still of cookies, which is, you know, a billion dollar brand. When we gets legalized, you know, like he's going to see the fruits of his labor and, that focus on ownership I think is really going to pay off on the longterm.

So I would highlight those two guys, in this tier as the ones that, I think were the most impressive to me. That's not to shade anybody else, but,

[00:18:25] Dan Runcie: Yeah, those two guys are also two of the few people who I see people still wearing their merchandise on a regular basis. Granted, I live in San Francisco. There's a cookie store here. So, I mean, I know there is a local connection for sure, but same with Nipsey Hussle. I mean, sadly, it's now been over 4 years since he passed away, and you still see Crenshaw shirts.

He understood, Nipsey especially, understood exactly where everything's going. And it's just so sad that, you know, it was gone so soon. Two names, I'm going to shout out here. I'm going to shout. I'm going to shout out Cardi B and I want to shout out Chris Lighty. So Cardi B talked about her a little with the Mona Scott young piece, but she's entered and ran her rap career more uniquely than other artists that we've seen at her level have. And I think that speaks a lot to just where the game is now. It's been over six years since Bodak Yellow came out. And it's been over five years now since her debut album. This is someone who hasn't put out a studio album in over five years.

And hasn't gone on tour in a traditional way, but it's still doing her thing. And I think this is one of the things that's unique. She finds interesting ways to monetize herself and to put herself on. She's like, Hey, I can do these private shows and they're going to pay me, you know, 1. 5 million or 3 million just to do a half an hour set.

I'm going to do my thing. I'm going to be there at Super Bowl weekend. I may not be performing at the Super Bowl, but I'm going to go do these private shows for Bob craft or the fanatics event or all these things and collect the checks. it's very interesting to see younger artists to do that Lionel Richie playbook, but she is like, Hey, I don't necessarily have to do that. And even though people always do try to, you know, loop her into the Nicki Minaj versus Cardi B beef, she still has lended her hand and extended it to other young artists, especially women in the game, whether it's Ice Spice and others, whether she's doing it through her talents and others. So she's someone that I hope as she continues on, you know, into her thirties and into her forties can continue to rise up this list.

And then Chris Lighty talked about a little bit with Mona Sky Young, co founder of Violator and everything they're able to do there. Sad that he was taken away so soon, but if you have not heard this yet and if you haven't listened to the podcast, I highly recommend the Mogul podcast series that was done several years ago on it.

It was done by Reggie Yose, who is Combat Jack, who has since passed away as well, but I highly recommend that if you want a full breakdown on everything Chris Leite did. Violator and after that was truly one of the early ones looking at product partnerships and a lot of the things that we see now that are common in hip hop.

[00:21:07] Zack Greenburg: And, you know, if we didn't have Chris Lighty, I don't think we would have had 50 Cent. I mean, at least not to the extent that we have him. you know, I mean, I remember writing my first story about 50 and like for Forbes, maybe 2008 and sitting down with Chris and just kind of like hearing him lay out the plan.

And again, it's the emphasis on ownership, right? you know, Chris Leidy, I think was the one who really pushed, 50 to take the equity in vitamin water and his parent company, rather than just do an endorsement. And, you know, obviously that became a huge, deal and really like a model for so much, not only of hip hop, but like other parts of the entertainment industry, you know, I think Chris definitely deserves a spot, maybe even should be a little higher. and you know, probably also, there's, you know, again, all these folks deserve a shout out, but Kevin Lyles, I think is, got one of the most inspirational stories. you know, it's another person, I think we've both interviewed a bunch of times, but, you know, just his journey from intern to president of Def Jam and I think seven years. And he just did it by working harder than everybody else like he wasn't an artist that got put there because he had some hit, it wasn't some kind of like nepotism deal, you know, he just outworked everybody and, you know, he had the talent and, you know, the horsepower to just like get it done. And to make that journey within seven years. So I think it's, for people who are listening and, you know, want to do something like that with their own career, you know, study Kevin Miles because he was able to make it, without being, you know, some kind of like preternatural, singing talent or something like that he just did it on smarts and work ethic.

[00:22:39] Dan Runcie: And one of the few people that co founded a record label and sold it a decade later for hundreds of millions of dollars, which is what he did 300 as well. Right? So of course, not 300 now underwater, but everything he did with Lyor and Todd, there, is impressive. There's not that many black founders in general. In tech, any sector that have built and exited companies for several hundred, a million dollars, the way that he was able to be a part of that. So, hats off

him.

[00:23:09] Zack Greenburg: yeah, I think it takes a special kind of guts to be able to, you know, I mean, he was a well paid executive with a cushy music job, you know, to leave that world, start your own thing. I mean, I know they had, you know, big backers and everything, but like to take a risk once you've already experienced that level of success and to go out and start something, you know, as opposed to starting something from scratch when you have nothing anyway.

I mean, it, takes a lot of gumption to do that. So, you know, again, yes, a pretty cool second act for Kevin miles.

[00:23:38] Dan Runcie: Indeed, the next group here, our impact runs deep. It is Nicki Will Smith at 28, Swiss beats 27, LL Cool J, 26, Coach K and P, 25, Julie Greenwald, 24. The E40 23, Pharrell 22, and Rick Ross, 21.

[00:24:01] Zack Greenburg: Yeah. I think, that's a pretty strong, deck there. And I think also, you know, here, you find some people who, you could argue should be higher or lower based on, you know, how much of their career was done in the hip hop music world, right? Like Queen Latifah, LL Cool J, Will Smith.

Obviously those are huge crossover acts. but I think they all got a lot of points from some of the voters because, you know, that is in one way, the measure of a mogul, like you're diversifying your portfolio and whether that's by owning different things or, you know, by getting into, different types of performance, you know, on the silver screen, I think that's a viable path too.

but just from like a purely musical entrepreneurial perspective, I would highlight, Swiss Beats and Pharrell, who I think, you know, the two of them are more influential than anybody in terms of like, I'd say Swizz in terms of art and Pharrell in terms of fashion. and you know, some of the things they've done around those two areas and, you know, Pharrell certainly, now with LVMH, but also before with Ice Cream, Billionaire Boys Club, you know, he was very active in starting his own things on the fashion side.

And, you know, kind of inspiring artists to do that. you know, would we have had a Yeezy if we hadn't had Pharrell, you know, doing what he was doing and, you know, and even doing what he did with Adidas? you know, I don't know about that. And, Swiss beads certainly, you know, not only from the art side of things, but you know, it's a really impressive art collection.

I did a story on him a few years ago and, you know, he's got like, Jeff Kuhn sculptures and Basquiat's and Warhol's and his, you know, like in his foyer. I mean, it's, pretty impressive stuff. but the way that he moves behind the scenes, as sort of like a corporate brand whisperer, at places, you know, like Bacardi, Lotus, you know, this goes on, you know, I think he, he's sort of like more quietly

influential than, some folks realize. And, you know, certainly has been earning, on par with, you know, with all the, you know, most of the names, if not higher than most of the names we've mentioned so far. and you know, what he's done on the, both of them, what they've done on the production side, also hard to top.

So that must count for something as well. I kind of went more than one shout out there, didn't I? So

[00:26:06] Dan Runcie: Yeah. No, that was good. That was good.

I'm glad you mentioned the two of them though, because if you didn't, I probably would've called the other one out. The thing about Swiss as well, everything that he's done with versus specifically also embodies this idea and definition of a mogul because he was able to be.

A kingmaker in the sense of creating opportunities for others. He did that through the equity that he was able to give all of those early participants in versus in trailer itself. And then additionally, with the careers that we're able to have a boost because of. everything that happened, with the matchups from versus specifically, you look at someone like Ashanti, who is now doing tours and pop it up every now and then she wasn't doing that before her versus and her battle versus Keisha Cole was one of the not, if not the most watched one that we've had.

You look at Jadakiss and everything that he's been able to do since his epic showdown against, with Lox versus Dipset with that versus you look at Jeezy versus Gucci Mane. I know that versus definitely had its peak popularity during the pandemic, but that kind of stuff that he was able to do with Timbaland, I think also speaks so much to everything that he's been able to do there.

And another person I want to mention to that was in this group as well that I think is similar is LL Cool J because I think similar to the way that. Swiss beets is Ella is also with someone that's been involved with multimedia with everything from the jump. He was the 1st artist to truly breakthrough from Def Jam and did it as a teenager.

So, of course, he gets plenty of shout out for that, but he's also always been trying to find ways to look out for that next generation of artists. And he's been doing some of that more recently with rock the bells, and that's its own. Company and entity now where they have a festival coming up as well to celebrate things that are happening with hip hops anniversary.

So it's been cool to see him do things as well. And I'll give a very brief shout out here to, coach K and P because they, similar to how I mentioned, Kevin Liles were able to build and grow a company and then sell it for, I believe, forget the exact sale price for, quality control. But they were able to do that thanks in part to a lot of the work that Ethiopia had done, helping to give quality control, the platform that it did, and especially in an era where I think it's harder for a record label to have a true brand, they were able to help give it a boost.

[00:28:36] Zack Greenburg: That's true. And on that note of labels, I think Julie Greenwald, there's a mention, you know, she and Craig Kalman, who's mentioned, in an earlier grouping, you know, run Atlantic together. And there's a lot of, of music that we wouldn't have seen if it had been for the two of them, you know, running the show over there.

So, shout out to Julie. I mean, the only one actually we haven't discussed here with E40 and Rick Ross. And I don't know, you know, probably get moving, but, do you think Rick Ross deserves to be number 21 on this entire list? Like ahead of Pharrell, ahead of, you know, some of the other names on here. I was surprised that he was ranked this high.

[00:29:09] Dan Runcie: I love the spicy questions. Cause this is what people wanted to hear the podcast about, right? They wanted to hear one of us, you know, poke the bear a little bit.

If Rick Ross was able to nail that dive in the pool, do you think you would have ranked him higher?

[00:29:21] Zack Greenburg: Ha ha ha ha ha ha. No, no, I wouldn't. I mean, I still know. I mean, you know, like I get it, you know, he's called the boss that he must be a mogul, You know, and, some of the things he's done in terms of, you know, Bel Air and Maybach music and all that. Sure. But like, you know, when you put them up against like some of the other ones, did he really do something new or was he more just like following a, blueprint that had worked for others before and, you know, executing it to a degree success, but like, again, not, you know, not to the level of, let's say Pharrell.

I think maybe I just, I'm salty that he ended up ahead of Pharrell. I think Pharrell is just way more influential and Mowgli, but, I don't know. What do you think?

[00:29:59] Dan Runcie: So, I've read 2 of Ross's books and I interviewed him once on Trapital. I think that, to your point, he did follow the blueprint that we saw from others. I think he is smart about the types of partnerships he does, but it does feel like a ditty light. Type of playbook that he's been able to do and build.

And I do think a lot of it makes sense. He may not necessarily have the large media entities the way that he does. Although I do think he's overdue for some type of comedy show or some type of reality show just following him around because I think he's hilarious. And anytime that he gets that, it could just generate something unique.

And I'm sure he's been hit up about it. I do think that he's done well for himself. Just thinking about. Now, how his career is growing, I think it's been what, 16, 17 years since hustling 1st came out. I think in this range, there is some flexibility there in terms of like, where people are in certain ways.

I get why he may not necessarily be as high. I'm sure if you looked at the net worth or the earnings, that some of the people that are lower than him may actually be higher. I think 1 of the knocks potentially is although Maybach music was cool. I wrote about this in Trapit as well. I think there was a missed opportunity.

And part of that comes from, huh, did Ross do all the things that he probably could have done from a leadership perspective to especially like, when Meek Mill and Wally were beefing and stuff. And I think Ross had a bit more of a laissez faire approach to things, which in some ways is kind of the opposite of King making as we're talking about this, right?

Can we really bring folks together and make something larger than it is. I think it was a bit tough in general for people to try to do everything themselves, try to be the boss of this label, which is signed to a different label because Rick Ross was signed to a different label than MNG was himself. And I think anytime you have that type of dynamic, it's just splitting the leadership interests. So I hear you.

[00:32:00] Zack Greenburg: Yeah. So then how much of a mogul are you, if your label is really, you know, so I guess everybody's labels on somebody else's label and have you distributed by something, but you know, it's like when they're like multiple labels kind of, you know, intertwined with your label, it kind of causes the question.

are you really the boss? If you have several bosses that you're answering to, but you know, I think actually though. in Rick Ross's defense, what he's done with Wingstop, I mean, that is pretty unique and, I don't know that anybody else on this list has something comparable in that space.

So, you know, maybe that's why, I think, you know, by virtue of that, you could put them pretty high up. And maybe that's what some of the judges were thinking, you know, but he also ended up on a lot of lists, you know, so some of the judges just kind of like, maybe we're getting to some of the judges sent rank lists, and they're like, you know, this person is the top and they should get the most points and other people were like, here are my people.

And you can just rank them evenly. and I think Rick Ross ended up on a lot of those lists. So, you know. I think again, maybe like I was alluding to earlier, he's a bit of a compiler, nothing wrong with that, you know, you can get into the hall of fame by compiling 3000 hits, but, it's interesting to see how, how the opinions differ. That's the whole fun of it.

[00:33:06] Dan Runcie: He runs his business is almost like how a small business owner would in a number of ways where he has a bunch of car washes and, you know, his is 1 of the family members does that he has his wing stops, right? He has that. And it is a bit of this, like, mogul dumbness from that perspective in terms of like, okay, I have my hands in these things and I've hired people to have, you know, different roles within that that doesn't necessarily have things in aggregate. It's a bit more of the strip mall mentality as opposed to the, you know, building a skyscraper that could then build other skyscrapers, but it's something worth mentioning, but I hope we keep that up with a few of the other rankings we have coming up as we dig into the top 20, here.

So, yeah, let's start with 20. So, 20, Queen Latifah, I think that she and, Ice Cube, who we'll get into in a minute, were one of the first that noticed, hey, I may not be able to do this rap thing forever, what are areas that I can expand this multimedia empire and everything I'm building.

She was able to do this with Living Single, the show that was Friends before Friends was, and even the way that she was able to show young black people that were having, you know, highly sought after roles, but they still had their interpersonal dynamics. It was cool. It was refreshing. It was aspirational, which I do think that a lot of the black sitcoms were in the 90s.

And she was able to do that, continue finding ways to put other people on as well through the work that she did. She was also willing to take risks. Like I remember when she was in set it off, people had a bunch of questions about, Oh, you're going to play a lesbian in this heist movie. What is this going to do for your career?

And she was willing to do that. And I think she is always, you know, be willing to take risks. So, you know, shout out to her and I'm glad that several people have mentioned her

[00:34:56] Zack Greenburg: Yeah. And I think she gets credit for, like you say, diversifying her portfolio. you know, into the acting world. it's worth noting, you know, she was barely ahead of Rick Ross. but you know, there is a big difference between 21 and 20. It's the top 20. So, again, I think, you know, she was a bit of a compiler, but there were a couple of people who ranked her in the top 10.

and, you know, I think just like in terms of the breadth of her career, you know, the longevity, the diversity of the things that she's gotten into. you know, even if it's not as much ownership as somebody, even like a Rick Ross, it's just like, having your hands in a lot of pies and like that really counts for something as a mogul.

So, I think it makes sense to see you there.

[00:35:36] Dan Runcie: Agreed 19 is Eminem. So let's talk about it. How do we feel about Eminem in 19?

[00:35:43] Zack Greenburg: You know, I think it's a weird one, honestly. you know, there's no doubting, his lyrical prowess and where, you know, where he kind of stacks up as part of like the pantheon of lyricists, like fine. But is he really a mogul? I mean, he's somebody who has been, you know, very reclusive at times.

 Who has, you know, kind of gotten in his own way at other times. I mean, I could see ranking him up here though, just by virtue of ownership of the music and sort of like the quality and quantity of his catalog. you know, what he did with D12, you know, he did have shady records and, you know, and all that.

So again, you know, there, there is kind of a layer cake of a label situation, like some of the folks who mentioned earlier across, but, you know, that was at least important to him to set up, you know, as his continued ownership of, You know, his work and, you know, certainly when it comes to like raw commercial prowess, you know, Eminem, is one of the best selling hip hop artists of all time.

If not the best, depending on how you look at it. And just, you know, simply by virtue of the amount of revenue he generated, you know, throughout the late 90s and early aughts at the peak of the sort of CD age there. you know, that deserves, some kind of something, even if he wasn't running around starting his own, you know, side businesses as much as some of these other folks

[00:37:02] Dan Runcie: Best selling artist of the 2000s by a pretty strong amount, I believe, and has the most of any genre, right? And the most streamed song of the 2000s as well, at least on Spotify with Lose Yourself, and I'm pretty sure Till I Collapse and maybe a couple of others aren't too far. Behind as Will Page as Spotify's former chief economist said, anytime Eminem farts or burps or releases anything on a streaming service, it provides a huge bump to everything in this back catalog.

So, I still laugh about that, but I do think that speaks to it there and. If, correct me if I'm wrong, but I think he was one of the first hip hop artists to have a Sirius XM channel himself.

So that's something that's unique and obviously Sirius is still doing its thing. So, shout out to him there. A bit higher than I probably would have ranked him, but that's why it's interesting to get the group results here. Ah, this one's gonna be spicy. Number 18. Your boy, Suge Knight.

[00:38:02] Zack Greenburg: Yeah, you know, I mean, I think this is one of the tougher ones on the entire list. You know, this is not like a list of, Ms. Congeniality or Mr. Congeniality, as you'll see, you know, some of the other names on here. Obviously, you know, Suge is in jail. he's been involved in the death of, you know, human beings that like that is, you know, not sort of like what you're after in a mogul here, but, enough people, you know, I guess felt that the business, if you just, you know, looking at it from a pure business perspective, was enough to put them up here. And, you know, there is no arguing that death row at its peak was one of the most influential record labels, you know, not just in hip hop, but of anything. I mean, any genre, when death row was at its hottest, I don't know any, kind of moment where any other, you know, you'd have to stack that up against peak Motown or, you know, Atlantic or something like that, but, you know, that was really like a, peak moment. So, you know, I think this is one of the things we run into on this list like if somebody exhibits, a level of, you know, sort of business ingenuity, you know, that counts for something and, you know, the other things that you do in your life and your career, you know, we'll detract from that, but, you know, what you did at your peak, I think will get you pretty far in a list like this when people kind of count, you know, we kind of count sort of like the ceiling as opposed to the average, in some cases. So, I don't know. What do you think?

[00:39:27] Dan Runcie: These are the two most impressive business moves that Suge Knight has done. Number two is shaking down Vanilla Ice to get his points for everything that he did on the album that had Ice Ice Baby there. Because he was able to use that money to then start and co found Death Row with Dr. Dre. That's number two.

Number one is at the 1995 Source Awards where he publicly makes his Call to attract Tupac to say, Hey, I know you're in jail, but we're riding with you. Tupac wasn't signed there at the time, but he knew that this was an opportunity. Tupac likely needed somewhere to call a home and he called his shot. He was able to make it happen.

I know everyone talks about the diddy shot about, you know, being all in the video death row. And that, of course, is infamous in its own right. But I think the number one thing that should night did is that that said. those 2 things speak to what should night is, 1, it is that muscle and the prowess of being able to overpower a situation and then take advantage.

And I think those were things that he was good at. That said, I don't think he was necessarily strong as a. Business leader, the company imploded in large part. And I don't think it imploded because of Dr. Dre, it imploded because of all of the things, all the shenanigans. And I think for what he was building, some of that just got a little too close to the sun, unfortunately. And, that's Chuck Knight

[00:40:49] Zack Greenburg: And, I think that, you know, in some of the reporting I've done over the years, One of the things people say is that Shug and a lot of the guys around him, you know, it wasn't that they were necessarily like that. It's just they kind of had been watching too many bad gangster movies and the music business, didn't know what to do with somebody like Suge Knight.

And so the more he kind of like played this role, the more he grew into it to where, to the point where he was actually living sort of a bad gangster movie. and sort of like created, turned himself into a monster. Yeah, so I think like the evolution. or the evolution, of somebody like Suge Knight is sort of fascinating in terms of like what you can, what sort of playing a role can do to you, over the course of time.

[00:41:32] Dan Runcie: Agreed. And well said number 17 here is America's most wanted ice cube. I'll start here to kick things off. I think that Ice Cube, like Queen Latifah mentioned earlier, was one of the early ones who had said that he knew that living and doing everything off a raft wasn't gonna last forever. And I think a lot of it was because he experienced some of the brunt and ugliness of it.

I mean, we've all seen the Straight Outta Compton movie. He goes into Jerry Heller's office. He starts smashing shit. He releases no Vaseline. There was definitely a no fucks given that carried through even after he was done with NWA, but he saw what this industry is like as well and then that's when he starts writing screenplays.

And then that's how Friday because the thing becomes a thing. And then. His career just continues to take off after that he still dabbled in rap and did his thing, but he definitely became known early on for one of the people that took a risk with cube entertainment and everything that he was able to do there.

And with any of the movies that he had, whether it was the movies with Mike Epps and plenty others, I do believe that most of these movies were pretty profitable. And he was able to. Do it work within the confines that he had and just continue to build everything he did from a career. We've seen him expand as well into everything that he's done with the big 3 specifically giving a home for basketball players that can still play, but maybe they can't make, you know, a 13 person NBA roster anymore.

I do think that some of his more recent news highlights that are a bit more politically driven or him walking around with Tucker Carlson and probably take it away from some of the more prominent memories of Hugh Ice Cube is, but yeah, that's why I had had him or that's why he, I think deserves to be, you know, where he is, on the list.

[00:43:27] Zack Greenburg: Yeah. And I think it's interesting, you know, you see, Eminem, Suge Knight, Ice Cube, all together, you know, they're all, inextricably connected to Dr. Dre. one way or the other. Right. and you know, would there, would Dre have been Dre without the three of them? you know, at different phases of his career, you know, I don't know, I mean, I think certainly what, Ice Cube did as part of NWA, you know, I wouldn't say that, that NWA was like.

like a business first organization. But like that wasn't the point of NWA and if it hadn't been for NWA, I don't think you would have been able to have business first organizations come out of hip hop in the way that you did. and certainly, you know, somebody like Dr. Dre, so. I think he gets extra points for that.

and, you know, this is probably why, you know, he was again, I don't know, was he compiler? He was, you know, he had like a lot of kind of middling, a lot of lists, a couple of top 10 votes, you know? So, you know, I think again, everybody has their favorite and he's up there for a lot of folks.

[00:44:27] Dan Runcie: Agreed. Number 16 is Drake. Should we poke the bear again?

[00:44:33] Zack Greenburg: Yeah. Does Drake deserve to be at number 16 on this list?

[00:44:37] Dan Runcie: This one surprised me, I was very surprised at the number of people that had him on the list, because you can make a case for the opposite, right? It's similar to the M and M thing, but almost to the extreme because M and M, yes, most commercially successful artists, XYZ. There's other artists that are less commercially successful at M and M that did more in that mogul definition but for Drake, it's even bigger of a Delta between these two, because here you have the most streamed artists of all time. So clearly commercially successful on its own, but people believe that OVO. Records or OVO sound itself actually could hurt an artist's career. And when you think about that, you think about some of the other multimedia things that he's done.

I know he's been active as an investor and I know that people like Nicki Minaj and others have said, Oh, you know, Drake's a low key billionaire. He just doesn't want you to know it personally. Again, he may be, I mean, I'm not sure what he may not disclose, but it isn't always just about wealth. It's like, what opportunities were you able to create for each other?

I do think it's good. That drink has been able to have different people that have been working alongside that. I think did get a bit of that drink stimulus package. And I think that's something that is quite debated, but I do think that. I feel like 21 Savage has definitely benefited from it. I mean, he was already commercially successful, but for him and Drake to do a joint album together was huge.

I think it was the same way that it was huge for Future and the same way that the Migos going on tour with Drake in 2018 was huge for them and anything else that Drake continues to do from that perspective. So I think it is, you know, debatable, but I mean, people do definitely add some weight to the artists themselves.

[00:46:18] Zack Greenburg: Yeah. And, you know, I think he should be around Eminem and whether they're both too high is an open question, but, you know, there's no doubting the commercial viability of what he's done. He did start more side businesses in Eminem, right? With OVO, whether it's the label, the festival, the clothing line, you know, he started a whiskey brand called Virginia black, which I tried once.

It tasted okay. but I don't think it's selling, you know, I don't know if he's even still doing it. yeah, he is definitely involved as a startup investor, so maybe, you know, we'll see some exits and we start to think of him differently at that point. But, yeah, you know, again, I think it's, some voters just kind of overweighted, you know, musical prowess and pop culture influence.

And if you're talking about that, I, I don't know anybody who's been as influential in the past 15 years. I mean, he's, you know, he's the most streamed artist of all time and that's got to count for something.

[00:47:08] Dan Runcie: Right. I know his cannabis line failed, but there's a lot of people, even people that we'll get to in this list that have also had failed or struggling cannabis

businesses. And, there's a lot that we could discuss there, but moving on number 15 is Sylvia Robinson, the originator.

[00:47:26] Zack Greenburg: I think she deserves to be in the top five, personally. because if there were no Sylvia Robinson, yeah, I mean, I don't know that we have hip hop and, you know, it's, you know, for those who don't know the story, she was running sugar hill records with her husband, Joe sylvia was actually a child star singer herself.

And, you know, they kind of had this like middling existence with their label. And then all of a sudden she's at this birthday party that she didn't even want to go to in Harlem and she sees Lovebug Starsky up on the microphone. A hip hop hippie to the hippie to the hip hip hop. You know, this is early, early seventies.

She's never heard anything like it. All the kids, you know, hands in the air, like you just don't care. And the whole thing. she tries to get Lovebug to sign. There's some kind of dispute, like with his management, never happens. And so she just goes to the pizzeria in New Jersey, finds three kids, get him, gets them to talk real fast over this record is how she described it.

and that's, you know, that's Rapper's Delight. That's the first hip hop song on Wax. That's the first hit. you know, that sort of spawns the whole genre. So, you could certainly argue, that, you know, she, borrowed or she hired, hired people who borrowed or whatever to do this, you know, like the idea that, that the first hip hop, track on wax was like, you know, originated in a pizza shop in New Jersey is really unfortunate cause it started at the Bronx, but like, you know, Sylvia came from Harlem.

She, you know, she, she knew that world. Like, you know, she was part of the music business and, for better or worse, she took hip hop from being, you know, just basically like spoken word in person kind of thing to being, you know, national events. Would it have happened eventually?

Yeah, I think so. But you know, who knows? I mean, it could have taken years longer and if it took years longer, you know, are we going to have the eighties with like run DMC and Def Jam and all that? Like, you know, I don't know. I mean, it, could have taken a lot longer to get off the ground if she hadn't done what she'd done.

And, you know, I don't think we, I don't think we should really be dinging Sylvia Robinson for her Machiavellian tactics, given some of the other people on this list, you know, we're talking like Suge Knight and whoever else, you know, there's quite nefarious characters, you know, as we get higher up too in this list.

So, you know, I don't think anything she did was. remotely as bad as, as like a lot of the dudes on this list. and, you know, so, you know, let's, I think we give her her due and yeah, I would definitely put her higher, but, you know, I think that's part of the deal when, when you have somebody who's that early on.

You know, people are going to say, Oh, well, you know, the total gross is not quite as much as so and so or whatever the case may be. And she wasn't as famous as some of the artists. So, but you know, she's up there, I mean, ahead of some pretty big names, Drake, Eminem, what have you. So, I think she's getting some flowers here

[00:50:00] Dan Runcie: The total gross knock is always one that makes me roll my eyes a bit because even if you take out the inflation aspect and the amount of money that's now in the industry, this is something that happens with pioneers in any type of industry. They are the ones that take the early hits to make it possible.

She and her work is what made it possible for rappers to like, she and her workers have made it possible for the message and anything else that we then see after that. Yes. Sugar Hill. records did have its struggles, afterward, like many other labels. But what do you think about broader context of the eighties being a very tough time in general for black music?

And there were only a certain number of decision makers in power that could make that happen. Yeah. You have to take that into account. And then additionally, she did stuff outside of even just this record label itself. As you mentioned, she was a recording artist herself. She also owned a nightclub. So there were other mogul type things that she had her hands.

And so shout out to Sylvia, who knows where this would be without her.

[00:51:00] Zack Greenburg: And probably worth caveating also that, you know, she did have some, Disputes over paying artists, as the years went on. So did like really a lot of people on this list is we could do like a whole separate, you know, like has some kind of dispute on how they pay artists. So, you know, that, that's probably worth noting too, but yeah, I mean, so does everybody else.

And, you know, I think she deserves her flowers.

[00:51:22] Dan Runcie: Number 14, Dame Dash,

[00:51:25] Zack Greenburg: Another, another hot one coming in. I mean, I think a lot of people would disagree with this, but you know, some people would put them even higher. I mean, I think he might be the most polarizing name on this entire list. Like some people had on top five, you know, some people didn't list them at all.

you know, I think it kind of comes in. We've had this conversation before. Would there be a Jay Z without a Damon Dash? you know, I mean, I think so, but it's that part of the, you know, we've talked about him in the context of startups and do you, you know, you need a different kind of founder for your like pre seed days than you do for your series B.

you know, if you're like a mafia, family, you need like a wartime Don, you know, versus like a peacetime Don or whatever it's called. But like, you know, I think, Dame Dash is a wartime Don. He's a seed stage startup founder. and he does it fair as well. You know, when it comes to like the growth stage and the corporate boardrooms and stuff, but, you know, there's no denying his brilliance.

you know, I think what he did, you know, certainly with rock aware, you know, expanding, the Roc-A-Fella empire beyond music. you know, maybe he realized that Jay was eventually going to leave and that they just, it wasn't going to be forever. And so he wanted to get his hands into, you know, as many different areas as he could, but, you know, there's like a lot of pro and a fair bit of con, but, you know, I think again, he's one who, you know, the pro outweighed the con, he didn't kill anybody, you know, so there's some people on here who did.

yeah, the con is only like so much con in my opinion.

[00:52:56] Dan Runcie: This conversation makes me think about, that backstage documentary that. Roc-A-Fella had put out after the hard knock life tour. And there's that infamous scene of Dave dash yelling and swearing at Kevin Lyles, who was at Def Jam at the time about the jackets and where what logo was supposed to be, or something other than that.

And thinking about that in context now of like, you know, how we talked about Kevin Lyles and everything he was able to do from that run and still can continue to do. And with where Dame Dash is, is in his career, Dame Dash doing his thing. I think he very much lived through and practice and preach the ownership standards that worked for him, where he has Dame Dash Studios, Dame Dash this, and he's been able to.

Create exactly what he wanted to. We heard him on that infamous 2015 breakfast club interview where he's yelling at DJ Envy and Charlemagne about, Oh, well, if your son wants a job, can you get him a job here at power 105 or whatever? No. Well, I can do him at where I'm at. And as comic as the delivery was, there is some aspect of mogul dumb.

That is a bit of that King making aspect of, okay, can you create opportunities for others around you? What those opportunities look like definitely vary. And I think that is a factor. So I do highlight that is something that Dame is able to do. And Dave is also similar to he's similar to a polarizing basketball player in the sense that the media may look and be like, why do you all fuck with this guy?

Like, what's going on? But if you ask the people that are actually in it, a lot of that would be like, oh, well, you got to look at Dame dash, Dame dash is the guy. And when I have. Interviewed. I'm sure you've interviewed and talked to many of young artists, too, or young label executives, too. A lot of them will reference Dave Dash.

A lot of them will look at what he was able to do alongside Roc-A-Fella, almost in the same way that, you know, players will swear by Kyrie or swear by James Harden or some other type of athlete that may be polarizing in their own right. And the media is like, Oh, why do you all like this guy? And it's like, Oh, well, no, you don't understand.

So there's something about. The people, and obviously I say that being self aware is us as people more so on the media side, as opposed to being in it themselves. But there's something about these young artists and moguls as well that have always looked up and respected what Dame has built. And even though it may not resonate, like, personally, I acknowledge that.

[00:55:23] Zack Greenburg: I would say, if you're going to make a basketball reference, Maybe not personality, but like basketball style, I'd almost liken him to Carmelo Anthony, you know, like he's an isolationist. He's a scorer, like, you know, he may not be very good at distributing the basketball, but like, you know, you throw him the ball in the corner and he's going to find a way to get it in.

And, You know, like a lot of people wouldn't think that he belongs in the Hall of Fame at all, you know, but some people would, be insistent on it. So, you know, yeah, I think that sort of like singular focus, you know, you could definitely give him credit for that,

[00:55:55] Dan Runcie: Agreed. Number 13, we are Cohen.

[00:55:58] Zack Greenburg: man, another like bulldozer of a human being, but, you know, certainly somebody who, you know, maybe he has also got the finger roll, you know, like he, he can have a light touch when needed. you know, I think just like in terms of longevity, we talk about longevity with some of the names on this list, you know, Leroy was there in the very beginning of hip hop, you know, managing rappers, and it gives the road manager run DMC, taking the leadership role, running Def Jam and Warner, starting 300.

Now, you know, YouTube's head of music, you know, the number of careers that he's touched over the years. From, you know, whatever hip hop pioneers you want to mention. I mean, you know, talking about LL Cool J, Run D. M. C., Beastie Boys. you know, to like later on with, you know, Jay, and then, you know, more recently, like whose career doesn't he touch, at YouTube? you know, I think he's a hard one to argue with. I mean, you know, I think though that, I like this basketball analogy though. You're like, he might be more of a Scottie Pippen because he's always been like, you know, there's almost always somebody else, Who he's working with, who is like higher up on this list than he is, you know, and we can get to some of those names in a bit, but, I guess now that he's at YouTube, he really is running the show.

 but he can score, he can make the assists. you know, get these rebounds, get the triple double. I think Lyor is a, definitely deserves a spot up here.

[00:57:18] Dan Runcie: Yeah, the do it for what? 4 plus decades. Now, if we're looking back to us, well, almost 4 decades, if we're looking at it in total, but impressive each step of the way. And there is something admirable. I think about the no fucks given mentality and perspective of just how he's been able to do things. And I do think that a lot of hip hop executives over time have been criticized for not thinking about efficiency and things like that enough.

And I do think that we, or was 1 of them who probably lead a bit more into that. And regardless of who it was, willing to call someone out about it. I think back to, there was this interview that he had done with Young Thug a couple years ago. And, this is back when Lyor was at 300 and Thug, they were talking about the process.

And he says to Thug, he's like, why don't you spend more time on your music? You have these like little songs that you just like, leave like little orphans. Like, why don't you like actually grow and nurture them? And it's back and forth where Thug's trying to be like, Oh, he doesn't understand it. You know, you got to just drop frequently the audience.

That's what they want to hear. So it was very much an interesting dichotomy of just seeing where things are of the streaming era, but I think that highlighted that even when thug was peak, like, everyone was like, oh, yeah, thug is the next 1 up. He was still like, hey, no, like, you need to do better. So there was something interesting about that.

And that. Even I think his mission as well with YouTube, like I think before he got there with YouTube, YouTube was often seen as such the enemy of the music industry in some ways, the same way that any other type of distributor is. And he's took it upon his badge to be like, no, I don't only want to be a friend to YouTube.

I want to be the number one. Source of revenue for the music industry. So really working to just change the narrative, both from a positioning perspective, but also everything there, I think has been a cool additional chapter in his career. Because I think a lot of the people that we have maybe named on this list that were big in the 80s or 90s, but are kind of on the list for legacy reasons like, we are still doing it.

[00:59:09] Zack Greenburg: Yeah. Yeah, absolutely. all right. Who do we got next? I think,

[00:59:12] Dan Runcie: 12, we got Jimmy Iovine.

[00:59:15] Zack Greenburg: That's interesting. I thought he would be higher. I think we both had him higher but you know, maybe I think sometimes, yeah, again, he's another one where when you have like such a broad portfolio of work and some of it is not in hip hop, then, you know, people don't necessarily consider you for a list like this.

So. you know, I mean, here's a guy who had experience with U2 and, you know, all these great rockers and, you know, he ended up at Apple. so I think maybe he got dinged a little bit for that, but you know, there's no doubting his impact, from Interscope to Beats, you know, certainly there's no Dre on the commercial side, without Jimmy.

And, you know, I think his ability to see, you know, there's this, famous. He and Dre have been walking down the beach in Malibu or wherever. and Dre's like, you know, I've got this new deal. somebody wants me to make sneakers. And Jimmy's like, F sneakers. Let's make speakers. you know, that was the birth of, Beats, or at least that's how I was told, but you could kind of see him saying that, right.

he always had that vision for not just creating. a new product, but an entirely new category. And that's what they did with beats. And I think that alone, you know, I mean, that's like, I think the single biggest hip hop business deal, 3 billion, selling to Apple. I think that should probably get him a little higher.

you know, maybe not top five, but I think we both put them higher than 12.

[01:00:38] Dan Runcie: Yeah, agreed. Yeah, nothing else to add there. I thought he would have been on the top 10, but yeah, it's always interesting to see how these things play out. Number 11, Jay Prince, Rap A Lot Records, another interesting one to see where he ended up on this list.

[01:00:54] Zack Greenburg: Yeah. I mean, he's sort of a sleeper pick, like hip hop heads, would know Jay Prince, but I don't know, you know, And certainly like most of the people we've mentioned are more well known from the pop culture standpoint. But I guess if you look at our judges, it's very hip hop industry specific. So, you know, specifics of, you know, I think Jay Prince is like, he's sort of like, you know, you talk about the rapper's rapper, he's like the hip hop moguls, hip hop mogul.

And I think, and again, it's reflected in the judges, like, you know, some people didn't have him on his list, but he got a ton of top 10 votes, you know, across the board. So, yeah, I think that, that propelled him is like, if you know, you know, you know, his significance to the genre.

[01:01:33] Dan Runcie: And even the artists rising now, you always hear that there's some connection to J Prince, which gives you an idea of the tentacles that he has right? When Drake is like, Oh, I decided not to come back and push a tee after what he said, because J Prince said I shouldn't. And you're like, okay, J Prince really is in this.

You hear about Meg the Stallion and just her coming up as a Houston rapper mentioning J Prince the way that she does. He's stayed in it. And for someone that hasn't touched a mic, he definitely is one of the highest people on this list that hasn't touched a mic.

[01:02:06] Zack Greenburg: I think he is the second highest sort of, well, we can

[01:02:13] Dan Runcie: Yeah, we could get into that. Yeah. so now we're into the top 10, number 10, SNOP Snoop Dogg.

[01:02:22] Zack Greenburg: I think this is a great place for Snoop. I mean, you know, he's certainly, You know, if you ask people like Snoop Dogg, artist or businessman, people would probably say artist first, but, he really does have a tremendous business sense. And, you know, in terms of like the raw, total of endorsement deals done, startup investments made, you know, like he is out there, with his brand.

And, you know, I think more than just about anybody else on this list and, you know, not in stupid ways, like he's very thoughtful about it. You know, and I think this whole like Martha Stewart, you know, bromance, whatever you want to call it, has been like hilarious and wonderful for his brand, but you know, you see him endorsing everything like Skechers and you know, he's in, in all these spots.

And, I think what he's doing Casa Verde, you know, that's just his vehicle to invest in cannabis is like very on point. He understands his brand. and you know, he understands ownership, but he also understands how to make money. And he's doing a little bit of both. So I think above all with Snoop, what is the most impressive is how he's transitioned from, you know, who he was at the beginning of his career to who he is now.

I mean, this is a guy who was, you know. On trial for murder. Like, you know, like this is quite a ways to go from there to being piling around with Martha Stewart. you know, I think she ultimately was the one who did the time, but like, you know, you know, just to have like. That kind of 180 for your personal brand, speaks to his brilliance in marketing.

and I think, you know, like he might be more emblematic than anybody in hip hop of how hip hop was able to transition from where it was in the 90s and the east coast, west coast thing to today and, tying up with corporate America. and you know, it's a pretty remarkable feat. So yeah, I think, he definitely deserves a spot in the top

[01:04:13] Dan Runcie: The man literally went from being the reason why Time Warner wanted nothing to do with its Interscope investment and being on the cover of a Newsweek in this like borderline mugshot photo of being like, Oh, this is what's wrong with hip hop to now being the emblematic brand whisperer. And yeah. On the covers with someone who actually did serve jail time, Martha Stewart, incredible.

Yeah. Incredible. Number 9, this one's interesting. So number 9 is Nas. He made it to the top 10 and I'm glad that Nas is on this list. Of course, legendary MC, very influential with everything he's done from an investing perspective and what he's been able to do as well with other types of partnerships, helping to revive the mass appeal brand as well.

I don't know if I've necessarily seen as much of the king making or as much of the, oh, I was able to put X and Y other person on in that same type of way, but I do respect that a lot of people had him on here and they likely do, you know, see him as inspiration in that way. But yeah, what are your thoughts?

[01:05:19] Zack Greenburg: I think with Nas, it all comes down to the startup investing and, you know, of anybody on this list, I think he is the most influential when it comes to hip hop and Silicon Valley and the relationship that he had with Ben Horowitz or it has, you know, basically they connected over a shared love of barbecue and hip hop.

I think Steve Stapp put them together. You know, it turned him from somebody who would never be considered for a list like this as recently as, you know, probably 10, 15 years ago, probably even 10 years ago, we wouldn't have had him on this list, to being top 10. And, you know, Nas was always the guy who he was the rapper's rapper, you know, he cared about the music, not the money.

And, you know, but I think, you know, thanks to Anthony Sala, who he worked with, you know, continues to work with, sort of a startup whisper for him. he was able to accumulate stakes in some of, you know, most influential startups out there. I mean, I think he was in early in Lyft, Coinbase, a whole bunch of others.

So, you know, Nas, to me, like, you could probably argue at this point, Jay Z may have a bigger portfolio. Jay Z may have overtaken everybody as sort of like the primary Silicon Valley a force among hip hop's royalty, but, you know, Nas was the one who really kind of showed the way. and the amount that he's done in a relatively short period of time, I think, you know, it's super impressive.

And, you know, when you talk about who did something different on this list, he did, that's something very different. so props to NOS for that.

[01:06:43] Dan Runcie: Agreed. Number 8 here is another interesting 1 to talk about is Kanye West. Kanye West famously rose up a lot of these net worth and, Highest earner list because of the success he had in fashion specifically with Adidas and his partnership with his brand Yeezy and arguably having the next most successful brand next to Jordan in terms of a single person being able to whether it's an athlete or entertainer being able to have.

A shoe and will look like a shoe franchise that was going to live on. Unfortunately, we've clearly seen that implode and the implosion a bit. Unfortunately, I do think is maybe part of the reason why someone like yay may not be even higher on this list is because being a mogul. Is something about, like, we've talked about before the ability to have the influence to be able to put the pieces in particular areas.

And for someone like yay to then go and make anti Semitic remarks, condone hate speech, promote hate speech. And you see all that crumbling down. One, of course, you mentioned that there's many people on this list that have done disgraceful things. But of course, we're hiding that calling that out here. But two, you just see how much that impact and it really destroyed so much of what has been able to build that shows some weakness in the quote unquote mogul foundation aspect of things.

And I know that he was able to create opportunities for others through good music. I think most famously, we look at Pusha T and everything Pusha T was able to do in his career after the, my beautiful Dark Twisted Fantasy album, and then becoming president of good music, I think. He's able to do that.

Some of the early co signs with Travis Scott and others, I think, you know, work to, Yeezy's advantage as well. I think we've still yet to see that infamous Donda org chart with all of the various things that Yeezy wants to build come to life. If he is able to build that at some point, then would happily rank him higher on a list like this.

But that's where I'm at with Ye on the mogul list.

[01:08:47] Zack Greenburg: Yeah. And I think like with, you know, a lot of other names on this list, it's sort of like, what was your ceiling? and you've got a lot of points for that. But then you get points taken off for, you know, for, sort of bad things you did or, or maybe not the things you, bad things you did from a personal level.

Cause a lot of people are still high up anyway, but at least from a business perspective, I mean. You know, yeah, he was, at one point the wealthiest hip hop artist in history. I think also the wealthiest musician of any genre, maybe the wealthiest entertainer, depending on how you count that.

but he also destroyed, like overnight the largest fortune in, hip hop history, at least to that point, with what he was doing. And, you know, you can talk about mental illness and that's, you know, very real, situation for him, unfortunately. But like, at the end of the day, you know, there's no condoning, the kind of stuff that he was saying and promoting and, you know, really having an effect.

And you could see in some of the statistics out there, you know, hate crimes, especially against Jews have been up, you know, over the past year or so. And there's a lot of other factors going into that, but like, you can't be contributing to that kind of thing. so, yeah, I think you know, if that hadn't happened, you know, I think he would have made it into the top five for sure.

and it's worth noting that, you know, he got, like, probably like a half dozen top five votes anyway. A lot of people left him off, you know, I don't know, I was bouncing all over where I would put him, but, I think you have to kind of consider not just what he created, but what he tore down.

And so, yeah, he should be on this list, you know, he created probably with maybe the exception of beats, the most valuable brand to come out of hip hop and Yeezy. But then he also tore it down. So, you know, that's what this list is about. you get to have these debates.

[01:10:20] Dan Runcie: Agreed. Agreed. Number seven, someone I'm excited to talk about 50 cent . 50, I mean, where do you even start? I think there's a few things 1, of course, you could talk about the rap career and how he was able to use shock value to his advantage with songs like how to rob and how that continue to be a through line with this career, starting all the beef with the murdering camp and everyone else there.

But I think that same mentality work to his advantage as a businessman to we have both talked to broken down the deal that he did with vitamin water and for hip hop, that was 1 of the 1st of its kind that we saw. That was really dope to see. He continued to do plenty of other business ventures, be involved with things, but I think what's kept him in the mix, especially the past decade or so is what he's been able to do on the multimedia side.

He has been single handedly. In many ways, carrying one of the legacy streaming platforms out there with stars. I was listening to a podcast that talked about how power and all of the various power books and chapters are responsible for 25% of the demand on that platform. And that, of course, that number came through parody analytics, so it doesn't exactly reflect on viewership, but when you look at how he was able to just continue that in an era where I think it's hard to create shows like that, that last, we obviously saw shows like Empire come and go and others, but he's still at it and it's been impressive to see how he's continued to that.

And especially with the type of people that acted in power, that's a bit of that. Yeah. Making aspect where you're creating opportunities for other artists, whether it's, you know, having Mary J Blige in there or having different folks like that. So, I do think as much as he still is the same 50 will still cloud will still do jokes.

We saw him courtside, the NBA playoffs of the Sacramento playoff, or the Sacramento Kings game because his alcohol company has a partnership with the Sacramento Kings. And I believe he also has one with the Houston Rockets too. So it's good to see that even 16 years after one of the most influential exits in hip hop, 50 is still doing his thing.

[01:12:25] Zack Greenburg: Yeah, for sure. And I think, it also goes back to ownership like so many of these cases, right when he got that deal, you know, his first record deal, he always says he went out and he took, you know, his first million dollars and went and, you know, registered all the trademarks for G unit and all these different things that he was going to do with it. and you know, he built a brand that was bigger than just 50 cent, right? He built a lot of brands that are bigger than just 50 cent. And I think what he did with vitamin water, I know we talked about it in the context of Chris Lighty, that set the blueprint, you know, not just for hip hop, but, you know, for the entertainment business on the whole, I remember I was doing a cover story on Ashton Kutcher for Forbes, you know, five, 10 years ago about his startup, sort of investing career. And, you know, he's Ashton Kutcher is probably like the most, successful entertainer investing in startups in terms of like successes and breadth and depth and all that. And I asked him why he started and he said, you know, I saw 50 cents deal. I, you know, I saw the vitamin water thing come through and I had just done like a Kodak film thing and, you know, for cash.

And I was like, man, what am I doing? I got to get in on these startups. So, you know, 50 really inspired Ashton Kutcher to go do the startup thing, which then I think led to the whole entertainment industry getting involved in the startup thing. and, you know, came back around to Nas and eventually Jay.

So, I think that, you know, what he did all the way back in when it was like two, 2006, 2007, that kind of set the mark, for others to follow and was, you know, new and interesting. I mean, Nas did it differently, right? Nas was more about being an actual VC at 50 cents on one deal that he thought was pretty cool and he was into the equity side of it, but yeah, I think that's, you know, that is definitely a trailblazing maneuver.

And even if he doesn't do anything else ever again, I think, you know. he's a rightful claim to the spot.

[01:14:09] Dan Runcie: Agreed . Number 6 on the list is Master P. he's another 1 that has continued to live on from a legacy perspective in terms of the young record label executives, the young artists, who are they modeling themselves after? Who do they want to do? And so many of them reference that late 90s, no limit run the ownership and how Master P.

As many other record label executives worth the time, which we'll get into, but how he was able to navigate things and just the feeling of branding marketing and all of the different areas that he's been able to have his hand into and multimedia in product sales. He gets his product app distribution and Walmart and other stores like that.

So it's been interesting and I think good to see him in the mix with things. He's always one of those names that comes up with, oh, there's this big brand for sale, whether it's Reebok or this sports team or this multimedia thing. He's always been in the mix with those, areas as well. So it's good to see him get representation on the list too.

[01:15:08] Zack Greenburg: Yeah. And I think just in terms of taking, you know, what had been sort of a regional label, in making it national and, sort of getting the kind of deal that he got. I think that's at the bar for a lot of deals to come and, you know, and that, that counts for a ton and, you know, getting involved into all kinds of different things that, you know, you may not even know until you like really take a close look at it, diversifying your portfolio, you know, as a businessman.

I mean, I think he's as good at, example of that as anybody.

[01:15:37] Dan Runcie: Agreed now we're in the top 5. This is where things get interesting. this 1st, 1, got a big exhale before this 1, co founder of death jam himself. Russell Simmons, where do we start?

[01:15:51] Zack Greenburg: Well, you know, I think it's instructive to look through. the different votes here. I mean, well, a lot of people left him out, but you know, a lot of people even emailed caveats to me, like, look, I hate to put him on here, you know, but his impact is undeniable. And he got a bunch of first place votes actually, but I think enough people left him off entirely that, you know, it averaged out to him being, and he was, it's pretty clear that he's in fifth on this list. It's not particularly close in either direction. but yeah, again, you talk about blueprints, right?

 Creating Def Jam, like sort of the iconic hip hop record label. And, you know, before all these artists that came along starting their own labels, you know, took a cue from Russell. all the artists that saw him create Fat Farm took a cue in creating clothing lines. And, you know, as time went on and he started getting into all these other different parts of the entertainment world, you know, I think that was something that other artists thought as well, but it's hard to name an artist whose career he's not touched, you know, of the legends that have been around for a couple of decades, you know, especially some of the names that we're going to get to in a minute. So, you know, obviously, can't discount, everything he's done, on the negative side, you know, certainly we've all seen the headlines, but, you know, his impact on the business remains, so significant that a lot of these people, the other voters put them on top and, you know, it's hard to argue his business influence.

[01:17:11] Dan Runcie: You can't tell the story of hip hop without including him. You also can't mention him in good practice without acknowledging everything, the good and the bad. One other thing I'll say on the good side was leaning into reality TV shows and things like that early with whether it was, you know, having his family involved with different things on TV, and things like that. I think we were able to see him continue to put himself on with their right. It's like, of course, obviously, as anyone knows, you know, his brothers in run DMC, see the whole family. And then you obviously have even wasn't it like Angela Simmons now, you know, is been able to build her own career as a business woman herself in large part.

Thanks to the platform that Russell Simmons was able to build there. So, yeah, I'm glad that he was on the list. I'm also glad we're able to have a full conversation about it. Yeah. Number four, top four is this is where we get into the famous Mount Rushmore, everyone always asks the question. Number four is a combination, but it's for good reason. It's Birdman and Slim, the co founders and leaders of Cash Money Records.

[01:18:17] Zack Greenburg: Yeah. I mean, I think, you know, we didn't really specify, whether or not you could put people together or not, but so many voters ranked them together. and they're really inextricable. I mean, they are of course, brothers and co founders of cash money. So, it only seemed appropriate to do that.

we only did that in one other case, but, you know, but here it made sense, you know, Birdman and Slim, you know, fire and ice, I mean, thunder and lightning, you know, that that's kind of their MO in cash money and, you know, you and I have talked about their dynamic a lot over the years, but, you know, I think similar to master P and taking what had been a regional label in cash money and, you know, extracting this incredible distribution deal from universal getting this huge advance, you know, in the 90s getting, it was $30 million, you know, even in, those days, you know, with inflation would have been, you know, probably at least double that at this point. Plus the ability to own everything going forward and then just their continued ability to stay, you know, you would talk about ownership throughout this list, I mean, those guys have managed maintain control of their catalog and, you know, through some, let's say there have been some disputes as to whether or not they held onto too much of it without distributing it fairly to their artists. But,

[01:19:30] Dan Runcie: generous way to put it.

[01:19:32] Zack Greenburg: You know, yeah, yeah, we could say, but, I think just the endurance cash money, you know, from the early days and hot boys and little Wayne, you know, coming through to like Drake, Nikki, Wayne, and you know, even if they never put out another hit, they're going to have that catalog to sit back on throwing off like double digit millions every year.

So, you know, it's interesting. I mean, I wonder what would have happened if they had sold their label at the peak of the catalog boom a couple of years ago when interest rates were so low. I mean, I think they could have gotten, I mean, I don't know, hundreds of millions of dollars for sure, maybe half a billion.

I mean, when you look at some of the numbers being thrown around. Yeah, I don't know about these days, now that things have cooled off a little bit on that front, but there's no denying their influence on the music and the ownership of the music. And you know, they certainly diversified. I think didn't Birdman own like gas stations or oil rigs or something for a hot minute there, but you know, I think it comes down to like, what's a mogul, you know, like a music mogul, a hip hop mogul, you know, for them to have launched and continue to own one of the most successful labels of all time, you know, and to have given so many other people on this list, the platform to start what they did, you know, and then they were pretty clearly ahead of Russell, which is interesting to me. and I think that's probably an effect of some people leaving Russell off, but there's no denying what Birdman and Slim did for the genre. And so, there they are, although some artists might, not be so happy and, you know, understandably.

[01:20:53] Dan Runcie: Yeah, I think part of the reason why they may be ahead of Russell in that way is because there's that ownership piece that goes back to it, right? I think we talked about it when we talked about, whether it was Def Jam or one of the other pods that we did, where the fact that Def Jam isn't necessarily owned by its co founders in the same way, but Cash Money is I think made a big of a difference there.

And I think With Birdman and slim as well, even if, let's say, there wasn't a whole 2nd chapter of the cash money story like, even if we didn't see the young money to then Drake and Nikki side of it, it's like those, even if you separated those would be 2 ownership stories. In themselves that would have had placement in this list of maybe high up.

You clearly saw Master P on this list where a lot of the recognition for Master P was things that he did in that early phase that Cash Money was able to as well. And then you have this whole run from 2007 up until 2018 because that was the last Drake album that came out under Cash Money. So the two hall of fame careers in themselves, it's almost similar to how Tom Brady, it's like, even if you look at everything that he did, you know, the 1st, 3rd of his career, then like the 2nd, 3rd, and like the 3rd, like they're all hall of fame careers in their own, right?

[01:22:14] Zack Greenburg: Yeah. I mean, and it's interesting too, when you look at sort of the totals of the votes, I mean, some of them, you know, there may be a couple of places in between artists, but there's only, you know, a few votes here, they're separating them. But the voters like really made it clear like there's a obvious top 10 and even within that, you know, the, top six are pretty clear. And then we're about to get into another really clear, the tippy top tier, the top three. So, you know, the voters made their voices known, in a unified sort of way.

[01:22:41] Dan Runcie: Agreed. So, yeah, let's get into it. The top 3 was pretty clear. People are probably know the names are probably just wondering what order. So, number 3 is Puff, Did

[01:22:50] Zack Greenburg: Can't argue with that. Although he might argue with it. I think, you know, between, Number two and three, it was actually extremely close in vote totals. And, you know, Puff is interesting case like he's on almost every list. but fascinating to me, nobody put him number one, like a lot of people put him number two, like four or five people, but a number two, nobody put him number one.

but you know, we've talked about how so many times on this list and on the, you know, podcast, shouldn't be surprised to listeners. That he's up there, but you know, to run through the accomplishments, I mean, to start off, you know, as an intern at Uptown, get fired and, you know, start from scratch basically in your early twenties and to build bad boy.

And then off of bad boy, you know, Sean, John and, Ciroc and all the other side brands he's built. I mean, he's a billionaire. I think one of only two current billionaires on this list, although there was a near billionaire and a previous billionaire. But, the longevity, you know, just, just like the sort of like single handedly not single handedly, but really like in some cases, it seemed like he was pulling hip hop up with him into the mainstream, throughout the late 90s and in a time when, you know, the sort of after the Bad Boy, death row feud. you know, we talked about Snoop Dogg and how he was able to get what he did. I mean, it's just as compelling. I think a story, what Puffy did at being so intimately involved in that and so quickly becoming, you know, in the late 90s, arguably the biggest star in the world, and then becoming this incredible, you know, executive first executive, you know, not so much of an artist, but really a businessman first and foremost, over the past, you know, a couple of decades.

 It just speaks to him. I like to say Puff is sort of like, he is Richard Branson, if Richard Branson just like happened to rap a little bit, you know, he's a businessman through and through, who happens to have some, you know, artistic ability and you could argue, you know, I would say more on the production side than on the lyrical side, but like, there's no denying data as a mogul if you look him up, you know, yeah, he's gotta be on the Rushmore, Mount Rushmore of any, hip hop mogul list.

[01:24:47] Dan Runcie: He has a track record. He has the businesses. The whole thing from the beginning, selling a lifestyle. He learned that as an intern, did it with music, did it in fashion, did it in spirits and he's continued to find ways. And like anyone has had businesses that have succeeded businesses that haven't, but that guy's never going to give up and it's really cool to see people like him and others on this list. Most of the people that made it this far on the list are at least 50 years old or higher. And I don't think that's a coincidence. There's something to be said for the longevity, but I also expect these people, if they're still alive to still be making moves in their seventies, the same way that you see granted hip hop itself is only 50 years old.

So you just don't see as much of the longevity there yet, but the same way that. We still see Charlie Munger and Warren Buffett in their 90s still being active players. If these hip hop moguls live as long as they do, hopefully we'll be able to see that too. And I think he's one of them that whatever the circumstances are, we'll always have some hand in the mix.

And that's something that's always admirable about Puff.

Number two, Dr. I mean, where do you start? You could start with the co founding of Death Row. He clearly learned a lot of the good things that came from Death Row because he was able to then start Aftermath and then create the platform to find Eminem, to then find 50 Cent, two of the most commercially successful artists that we've ever seen in hip hop.

And then all that's before Beats by Dre, as we've discussed. On separate conversations, and even in this 1, the most successful hip hop or the largest hip hop business, deal that we've seen and everything that he's just continued to do throughout. I feel is so special. This is a mogul related, but it was so special just to see the Super Bowl performance that it sounds like he had a big hand and just making sure everything was able to work the way that it did.

And he got help in many ways with some of that. We're going to get into at the top of the list, but it was really cool to just see everything. And in many ways, it felt like a culmination of everything dre has built in his career.

[01:26:55] Zack Greenburg: Yeah. And I think with Dre, it's always quality, not quantity, right? Whether it's bringing up artists, you know, that he's not going to co sign too many of them. But when he does, it's going to be Kendrick or 50 or Eminem. you know, he's not going to create too many products, but when he does, it's going to be beats, right? and you know, he's not going to perform that much, but when he does, it'll be like the halftime show, it'll be the Tupac hologram situation. you know, he is like the mad scientist sort of ethos going on that he sometimes alludes to. you know, he just goes and works and works and works and works and works and gets it perfect and then puts it out in the world and it might take decades. I mean, how many albums, three studio albums, really like three solo albums in his entire career. So like that's Dre. And I think it's interesting, you know, Diddy, is more trial and error. I think, he's out there, like he's willing to let the world see him fail, you know, and see him succeed. And I think Diddy certainly has more successes than Dre, but he has more failures, at least publicly. And, you know, just the idea, I mean, I guess it kind of comes down to beats versus Ciroc. I mean, beats, being, I think more influential at the end of the day in, in creating a category, you know, than just a product.

I think Ciroc, it wasn't a category. He did something different with spirits. He kind of like turned vodka into champagne. It's not even really vodka, which is a whole other story, but, whatever it is, he turned it into champagne. And like this could be the art of celebration and all of that, you know, it'll be interesting to see what did he does now, you know, given the state of affairs of Ciroc, but anyway, I mean, back to Dre, you know, again, just like the breadth, the longevity from where he was to where he is, you know, and I think also, looking at Nas, right?

Nas did most of what he did in the past 10 years, Dre, you know, from the beginning of Beats about 15 years ago to where he is today. If you take that out, like, yeah, like you said, he's probably still on here, but probably down around. So it's Beats or Pharrell or something like that. just to be able to have vaulted from there number two in 15 years.

 And you know, the impact that Beats has even to this day, I think. Yeah, you know, so it's very close. Diddy and Dre. I mean, I don't know, how did you rank? I think I had, Diddy as number two and Dre at three, but that's, you know, I don't know. I was really agonizing over that one.

[01:29:06] Dan Runcie: Yeah, I did it too. I had Dre at 6. So, yeah, it was, pretty close there, but yeah, agree with everything you said. And with that, we got to get into the number 1. The business man, not the business man. And you wrote a book about him actually too. If you count three Kings, number one, no surprise Jay Z.

[01:29:25] Zack Greenburg: Yeah, that's right. Jay-Z was the clear winner here, know, no surprises. he got the most first place votes out of anybody. He got 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, you know, like almost half of the people here put him number one and then there's like a ton of two and three votes. So, you know, yeah, I mean. you could certainly argue, that Puff and Dre, you know, their biggest successes were bigger than Jay Z's biggest success. So rockin and beats, would probably be bigger than any single, deal that Jay Z put together, but just like. The amount of different deals, you know, from the early days and Roc-A-Fella records and rock aware to, you know, to transitioning into being this sort of like mass market power player, the light nation deal, you know, launching do say, and I'm on to Brynjolf and all of that, you know, to have o wnership and to get paid and to continue to be, you know, musically relevant at the same time throughout it all. I mean, yeah, I think, that it's, pretty clear why Jay Z is number one. And, you know, I don't think anybody would really argue with that except for maybe Diddy.

[01:30:33] Dan Runcie: Yeah, he does the most. I think that you've seen him. You've seen him succeed with ownership. You've seen him succeed with partnerships at the highest levels. We've seen him navigate difficult business relationships. We've seen him make mistakes as well with things that he may be oversaw, but was able to still think through and come out somewhat ahead.

Speaking specifically about title and some of the things there, even in the failures, you could still see the through line about why he thought this was the best way to go about things. I think that. Not a surprise. And I think he definitely deserves to be at the top of the list for sure. A hundred percent.

[01:31:12] Zack Greenburg: And, you know, as far as looking at everybody's career and who you can kind of learn the most from everybody on here, you can learn something from and, you can learn from their successes, but I think it's also worth looking at what didn't work and how did they respond? You know, and, Jay Z likes to say a loss and a loss, it's a lesson.

And, you know, he's out there taking chances and, it doesn't always work. And I think earlier in his career, he only wanted to show you the parts that did work, and now he's kind of willing to, you know, show you the whole package. But, you know, itt certainly helps, when you're married to the biggest star in the world, arguably.

but look, I think both of them have been very smart about that relationship and how they leverage it to get into things like they have this big Tiffany's campaign, you know, certainly their real estate portfolio has improved together with, you know, the addition of this, like, I think they just got a 200 million house in Malibu and stuff like that.

So, I think with Jay, the way he handles every relationship, every release, it all builds toward the next thing. And, yeah, he's a chess player. He's thinking 10 steps ahead and, you know, it, kind of makes you wonder like, what is his next big step? I know he's, gotten a lot of big paychecks recently selling half of, Armand de Brignac and doing a joint venture there with LVMH, he's got a, huge check, I think around 700 million, for his stake in D'Ussé Cognac. So I'm particularly interested in, you know, what it is that he's kind of building up his war chest, to get next. And, I've heard rumors that it might be in, soccer, or in American football.

so we'll see. I mean, it could be any one of those things, but you know, don't be surprised when we check in 50 years, if he's like, you know, Jeff Bezos territory,

maybe sooner.

[01:32:47] Dan Runcie: and again, the fact that he's been able to help the people around him and make them successful too. He had that line that, song boss with Beyonce on that, album they put out together where he's like, here, we say you're broke if everybody, or here, you're not successful. We say everybody's broke except for you.

I know I butchered the line. I forget exactly what it is, but it's something like that. It's It's very similar to the pound cake line that he had had as well. So, at the end of the day, that speaks to his ability to do that. so yeah, this was really fun and it was really interesting to go through the list.

And now that we're done with at least that part of the list, now, were there any snubs on your end? I know we talked about a lot of the placement of particular people, but was there anyone, ah, that wasn't on the list that we didn't talk about at all today, that you were like, man, like wish that person had gotten in?

[01:33:35] Zack Greenburg: Yeah. I thought it was kind of surprising that DJ Khaled wasn't on here. I voted for him. I ranked him fairly highly, you know, I don't see why he would be off, but somebody like TI or even Rick Ross would be on, you know, having this hand in a lot of different things. I think also on a social media perspective, he's been really front of the pack.

So, yeah, I would put Khaled up there. I think RZA belongs up here too. some of the things he's done. You know, just like being the mastermind of the Wu Tang Clan period is, you know, kind of mogul, mogul move to kind of like come up with that idea. And, you know, unite all these guys from Staten Island under the banner of Kung Fu and hip hop.

It's like, what? They talk about something new and different, you know, and his hand in. And, you know, the secret album, once upon a time in Shaolin and, you know, all the things that that led to, and, you know, hip hop is already collectibles. It's just kind of like debates in the industry. so I think, RZA deserves a look. but, would be the two that kind of stick out to me as, you know, I think probably deserve a spot on here, but, but not quite enough people shared my views here.

[01:34:38] Dan Runcie: Yeah, I think that's a good one. I think to discuss someone that hasn't necessarily came in, I'll talk about 2 people. They're more recent people in the game, but I do think that a lot of people have been inspired by what they've done. 1 is Ghazi and what he's been able to do at empire specifically from a record label perspective.

But, you know, we started that at a point where a lot of people didn't even think it was viable to have a business where you were more than a just typical distributor, but you were still offering artists to at least maintain whether it's their masters or have just flexible record contracts where it's like, okay, let's partner on this project.

Let's partner on this and we see how fragmented music is now. And I think they were clearly ahead in some ways with that. And I think that works to their advantage too. And similarly, J Cole was someone who got on this list, but I think I'd actually give a shout out to his business partner. And CEO of DreamVille, Eib Hamad and what they've been able to do.

They're really trying to bring a platform. And I think in many ways, one of the things that DreamVille is, and other labels have navigated, how do you work to build a platform beyond the breakout star that you have? So that was another name that, that came to mind.

[01:35:50] Zack Greenburg: for sure. no, those, all make sense to me as well.

[01:35:52] Dan Runcie: Yeah, and then on this note, I think it was interesting because now that we're reflecting on the list, there's a few trends that I wanted to call out to get your thought on 1 was the placement of producers. And this is a 2 part question because 1, I do think that producers, especially the super producers in hip hop did quite well.

If we're looking at this list, just to kind of name through the names. Dr. Dre number 2. Kanye West number 8. Where's Swiss Beats here? We have Pharrell, of course, at 22 and we have Swiss Beats at 27 and I'm probably forgetting a couple of people there. Do you think there's something specific about producers as a job?

That makes them either more likely, or that has or any commonality with those folks and why that may line up with their placement on a list like this.

[01:36:45] Zack Greenburg: Yeah, I think a lot of the people who are producers are, you know, some of the time are there because, you know, they didn't quite take off as lyricists the same way. Although some people disagree with this, look at Dre, okay, fine. But like Dre was always a better producer than he was a lyricist. Puff was always a better producer than he was a lyricist.

Swizz was always a better producer than he was a lyricist. I mean. You know, you could, hot take, but like, you could argue that with Kanye too, I mean, that's less of a slight to Kanye's lyricism and more of like, just a praise for his production. But think that, you know, when let's say, being a lyricist, isn't your calling card, whether it's production or something else, you have to make yourself viable in other ways.

And I think that, especially as a producer, you're often involved, you know, more in the business side and, you know, what are the splits going to look like, who's got the publishing, all of that, you kind of necessarily end up. More in local territory, whereas it's easier maybe to just be a recording artist and to take checks from your label.

it's sort of like, you know, kind of comes to the territory more when you're involved in the production side of things.

[01:37:47] Dan Runcie: I think that last piece is key because you are more cognizant of the splits. You are a bit of the maestro of making sure everything works out the same way that it does to be able to do that there, which maybe speaks to some of the reason why, you know, you mentioned Cal it as someone that. Probably would have expected to see a little bit higher, although his work as a producer is a little bit different than some of the folks that we mentioned here, but people that are on the younger side that I do think have a lot in common with the folks you mentioned here to be interested to see where will someone like Zaytoven, Metro Boomin, Mike Wilmated, some of the super producers or close to it of the streaming era that we've seen, will we see them be able to make Those moves in the future of the people that I mentioned, I think Metro Boomin is probably the closest there.

Of course, he recently sold his catalog. I think that he's someone that seems to move a little bit different. He's releasing his own albums that do have his own beat production there in a way where Mike Will and Zaytoven strike me a little bit more as being purely entrusted in the musical aspect of things.

[01:38:56] Zack Greenburg: Yeah, that makes sense. I mean, and I think if we're talking about, you know, younger individuals, who, you know, you might see on this list in 10 years, or maybe even you could have seen them now, but, I think, you know, Travis Scott, and Tyler, the creator are two names that I would point to, Travis Scott, I think probably got dinged for, you know, what happened, you know, at, at his festival.

And, you know, that's like kind of a big, you know, impediment for people to throw on the list. But, you know, those kinds of concerns didn't. It stopped them from listing other folks who had some pretty serious, you know, kind of like moral, asterisks around, around their names.

So I think what Travis has done with Cactus Jack, You know, he was really on the, sort of on the Kanye path from a commercial perspective and, you know, let's see how it goes with this new utopia rollout. But yeah, I think people have kind of a short memory and are willing to move on.

And, you know, he could be back in the conversation again soon. And I think Tyler, the creator too. I mean, I think he's another one, you know, whether it's music festivals or, clothing, you know, he's definitely got a hand in. a bunch of really interesting different businesses and, you know, maybe part of it, maybe he ends up more like in the Pharrell kind of position where it's not necessarily quite as mainstream, but it's, widely respected and, you know, lucrative and popular. So I could see the two of them moving up here in years to come.

[01:40:13] Dan Runcie: And Tyler too is unique because he spoke to an audience of fans and people that weren't being spoken to in that same type of way, right? Everyone else is trying to speak to the aspirational cool person. Tyler said himself, he was reaching the outcasts. He was reaching the people that would go on late night runs to Taco Bell and stuff like that.

And that was an audience that hip hop mainstream hip hop was reaching. So I think that speaks a lot to his success there. So, final question here, which I think is a good one and you posted right before we started recording this mogul list is very representative in a lot of ways of who the greatest artists are that happened to be successful in business.

And the question was up to interpretation in many ways. But if you were picking a team or a few people, whether it's people we've mentioned or people we haven't mentioned to run your mogul empire. Who would make your list? Let's say if there's 3 to 4 names that come to mind of who would make your list, who would it be?

[01:41:13] Zack Greenburg: Yeah, I think the boring answer is Jay Z, and that's probably, you know, most people's answer because that's why, you know, he got so many first place votes, but, you know, looking through the top 20, I mean, there are a lot of people who would not want running my mogul empire, but, you know, if I had to pick three, let's say out of the top 20, or maybe even the whole list, I think, I'd probably go like Jay, Lyor, and Sylvia Robinson, because they all just get shit done one way or the other.

They're all individually brilliant, creative, Machiavellian, you know, like, they all kind of like pushed the line on a lot of things, but they didn't cross it fully, in my opinion, at least compared to some of the other people, on the list, you know, at least in a, like, something is illegal kind of way, you know, or I guess anywhere you look there's always these debates, but I think that all three exhibit a certain level of, you know, in different degrees, like you need something done.

They're going to get it done. You're not worried that they're going to let their ego get in the way, you know, they could be the star or it could be the Jordan or the Pippin. and they have the talent to get it done, you know, no matter what it is that you need done. So I probably go with those three as my top.

What about you?

[01:42:23] Dan Runcie: I feel like we have a similar minded list. So I would have Sylvia Robinson as the board chair. I want someone that can control those stakeholders, make sure that we're good and also just keep a good eye and keep the company in check as well. I would want Jay to be president of the company because I think as president, it's good to have someone that.

Can be a bit of the public salesperson can get the right amount of support for buy in can be included in particular sales pitches for an actual CEO. I'll take Lyor again. I think the shrewdness, the no fucks given in a lot of ways. But still having a calling card to be able to get people aligned with is important.

And I'll take, Steve Stout is my CMO and I'll have Jay Prince as a special advisor to help address any of

the issues or anything like that. that's the

dream team.

[01:43:11] Zack Greenburg: I like that. I like that one. Yeah.

[01:43:14] Dan Runcie: All right. Well, Zack, anything else, that we should mention before we close things out on the hip hops, 50 greatest mogul list.

[01:43:22] Zack Greenburg: Yeah, you know, I think it's interesting to reflect in the context of hip hop's 50th anniversary. And, you know, when you look at sort of some of the pioneers, who started it all, you know, really there aren't any other than Sylvia who were there at the very beginning. And even then you could argue, you know, she came kind of five years late.

So, you know, I hope that over the, you know, over the rest of the year, some of these folks do start to get their flowers in the mainstream in a way that they haven't before. You know, whether it's Herc or Flash or, you know, some of the other people, Kaz, who are sort of around Grand Wizard Theodore, you know, some people like that who haven't gotten maybe quite their due.

So, you know, I would look for that, through the year. And that's kind of a hope of mine. And, you know, I mean, yeah, none of them really got to be. Let's say, they didn't get to partake in the spoils in the way that some of the people who came in a later did. So that, that would be my one, final thought as we head into this rest of the summer of celebration of the 50th anniversary.

[01:44:16] Dan Runcie: Yeah, I'm excited. I think it was great to be able to use as an opportunity to reflect, to be able to highlight and think more broadly about it. There's been so many different types of 50, this 50, that list, and I'm sure we'll see more of them as well. I think that this 1 is a bit unique because of all the factors that we brought into and how varied the list was and how we brought more people into this process, as opposed to just having, of course, there's a form of this. That was just you and I talking it out and making sure that where we thought things made sense, but it was really good to be able to include some of the pioneers and some of the leaders themselves in this.

So with that salute to hip hop and everything that is created, and obviously you and I being able to have work in this industry as well. So shout out, know, it's a privilege and honor to be able to contribute and offer something like this.

[01:45:07] Zack Greenburg: Yeah. Privilege and honor indeed. So, yeah, it's a lot of fun and good to get, you know, good to be able to look back a little bit.

[01:45:13] Dan Runcie: Agreed. Thanks, man. Appreciate it.

[01:45:15] Zack Greenburg: All right, Dan, have a good one.

[01:45:16] Dan Runcie: You too.

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