The Rise and Fall of Roc-a-Fella Records

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music as a platform

In 1997, Roc-a-Fella left Priority Records and brought the label to Def Jam. Roc sold 50% of the company to Def Jam for $1.5 million. It wasn’t a huge deal, like Cash Money or No Limit’s lucrative distribution deals. But at the time, Roc-a-Fella was just Jay Z (and a one-off R&B album from Christión). It was still a few years away from becoming a collective with multiple commercially successful acts.

A few years later, its $10 million sale to Island Def Jam for the remaining 50% wasn’t a huge deal either. But these deals were a platform. Music was the launch pad for everything else.

At its height, Rocawear cleared nine figures in annual revenue (and was eventually sold for nine figures). Roc Films released Streets Is Watching, Paid In Full, State Property, documentaries, and more. That was their platform.

They executed the same framework in last year’s Culture Report. Artists become millionaires selling music, but they become billionaires selling products.

This concept wasn’t new in hip-hop. Jay Z, Dame Dash, and Biggs executed this over 20 years ago. Jay Z didn’t sell as much as other superstar rappers. Roc-a-Fella Records didn’t have as much ownership or royalty points as others, but they got equity in other areas. That mentality set the stage for the deals Jay Z continued to pursue.

the turning point

Jay’s third album, Vol. 2… Hard Knock Life is often called the turning point for himself and Roc-a-Fella. It’s true, but there were two other important factors: frequency and touring.

Let’s start with frequency. Jay Z released an album every year from 1996 to 2003. Some were classics, a few were forgettable, but he was always in the conversation. That was the Def Jam formula.

By January 1999, Jay Z and DMX had released three albums in the prior eight months that grossed over $82 million in sales. Def Jam’s leaders, Lyor Cohen and Kevin Liles, had their foot on the gas.

“There was a huge demand and very little supply,” Lyor said in an interview with The Fader. He offered DMX a $1 million bonus if he could release a second album in 1998, which led to Flesh of My Flesh, Blood of My Blood. In 1999, Def Jam was ready to sell the remaining half of its business to Polygram. Lyor wanted to squeeze as much revenue as possible into the calendar year to command top-dollar for the company.

On the touring side, The Hard Knock Life Tour is Roc-a-Fella’s dark horse, underappreciated business move. In the late 90s, a nationwide arena rap tour was rare. Promoters thought rap concerts were too violent. They wanted R&B collaborations like Smokin’ Grooves or Puff Daddy & The Family. Despite the unfair and biased profiling, Dame’s hustler mentality shined through.

His main goal was to control the narrative. Dame assured the media there would be no issues. In several cities, he paid for additional security at the shows from the Fruit of Islam. He stocked the tour bus with movies like As Good As It Gets and Good Will Hunting to prove that they’re not just watching gangster movies. They supported the Colorado community after the Columbine shooting. The list goes on.

The Hard Knock Life Tour grossed $18 million. It’s not much compared to hip-hop doors today, but this tour paved the way for those to happen. After Hard Knock Life, we soon saw The Up In Smoke Tour, Ruff Ryders / Cash Money, and several other rap arena tours in the 2000s.

the infamous split

The Jay Z and Dame Dash split always felt inevitable, but the timing was rough. Here are the releases leading up to break up, from March 2003 to February 2004:

Freeway’s Philadelphia Freeway, The Diplomat’s Diplomatic Immunity, Juelz Santana’s From Me to U, Jay Z’s The Black Album, Memphis Bleek’s M.A.D.E., Kanye West’s The College Dropout, and Young Gunz’ Tough Luv

That’s the most prolific year Roc-a-Fella had. Imagine if the Marvel Cinematic Universe ended after 2016’s Captain America – Civil War. We would have missed some great cinema (sorry, Martin Scorsese). That’s how rough the timing of the Jay Z and Dame Dash split was.

Sure, Dame and Jay had issues leading up to the release of The Black Album or the “promotion” of Cam’Ron, but the underlying tension came from their conflicting leadership styles.

Jay wanted to be rich. Dame wanted to be king. Jay moved like a private equity investor making M&A deals. Dame wanted to call the shots and maintain control. As mentioned in Trapital’s essay on Jay and Dame’s split, the two go hand in hand.

Dame is built for early-stage companies. He had the hustle to push Hot 97 for early radio play and the determination to get his record label off the ground. But like any company, the seed stage leaders might not be the best for the Series B or C stage. It’s often time for a leadership shake-up to reach a different level.

I always think about Kanye West’s 2013 interview on The Breakfast Club, where he explains why he decided to partner with Jay instead of Dame:

“The problem was with Dame his truth was more accurate and more closer to what mine was, but his technique was harsh for me as a young kid and stuff. I felt like a little bit more pressure. And Jay Z was a nice guy. And also I felt like I had that truth that Dame has in him. We the same. Me and [Cam’Ron’], me and Dame, we the same. But I wanted to learn this technique that Jay got of actually being likable. Jay Z know how to move in a room full of vultures.”

The quote says a lot about Ye, especially over the last decade, as well as the people he mentioned.

who lost the most?

The media often pits Dame as the one who took an L. But I’ve met Dame, been to his house, and seen how he lives. He’s doing just fine. No one “lost” but Zack and I agreed that the person who was likely held back the most from reaching their full potential as an artist was Cam’Ron.

In 2002 and 2003, KIla Cam was on top. That stretch led to Come Home With Me and Diplomatic Immunity. **He **starred in Paid In Full, brought the whole Dipset crew with him, and made pink fashionable. Plus, he and Dame Dash blessed us with the “U Mad” line in an unforgettable appearance on The O’Reilly Factor.

Unfortunately, that was his commercial peak. His next album Purple Haze had great songs like “Down and Out” but also had the infamous line, “I got computers putin’.”

While Juelz Santana and Jim Jones still had big hits to come in the post-Roc split days, Cam never quite got there again.

I could write another essay’s worth on takeaways from our episode. Here are a few more topics we discussed:

–  the days before Roc-a-Fella started

–  how Jay Z’s touring strategy has evolved

–  Ye’s tenure on Roc-a-Fella Records

Subscribe to the podcast here to get it when it’s out.


0:25 Roc-A-Fella origin story

3:57 Reasonable Doubt

10:30 Friendly rivalry with Bad Boy Records

14:00 50-50 deal with Def Jam

17:13 How Roc-A-Fella’s deal compared to others

20:50 The Hard Knock Life Tour’s impact 

30:46 Expanding the brand beyond Jay Z 

33:23 Why Dame and Jay’s split was inevitable

43:50 Artists taking sides48:30 Best Roc-a-Fella signing?

49:50 Best business move?

53:05 Darkhorse move?

58:41 Missed opportunity? 

1:03:50 Will Dame and Jay ever make up?

1:09:09 Who won the most from Roc-a-Fella? 


[00:00:00] Zack Greenburg: I think it was really good for hip hop, and I don’t think it was ever going to turn violent, but I think again, there was just this kind of like national paranoia around hip hop and, there is, you know, in waves.

I think it was just a, good reminder that you can have like a spirited dispute and, it’s okay and it’s entertainment, you know? and it’s, nothing that anybody needs to be afraid of. So, you know, of course like credit to Jay and Nas for resolving it amicably, yeah, I mean just, to have that end, you know, like very amicably I think was just so good for everybody involved. And then, you know, I think it’s really fun to watch, Jay and Nas as their relationship has evolved And, you know, Nas was sort of always like the one who was sort of behind, when it came to the business of things.

[00:00:46] Dan Runcie Intro: Hey, welcome to the Capital Podcast. I’m your host and the founder of Capital, Dan Runy. This podcast is your place to gain insights from executives in music, media, entertainment, and more who are taking hip hop culture to the next level.

[00:01:13] Dan Runcie Guest Intro: This episode is a rewind. We’re going back in the clock to the late nineties, early two thousands, and we are revisiting one of. The most iconic record labels at the time, the one and only Roc-A-Fella Records. Roc-A-Fella Records, is the record label started by Jay-Z Dame Dash, Big Burke, and went on to be one of the most iconic hip hop record labels and hip hop brands, and that’s a key thing from this conversation.

I was joined by my friend Zach O’Malley Greenberg. He wrote Empire State of Mind, a biography on Jay-Z, and he also wrote Three Kings that broke down Jay-Z, Dr. Dre, and Diddy’s Business Moves. So he was a perfect person to have this conversation with. We talked about the highs of this record label, the lows, some of the best business moves where Jay-Z and Dame didn’t see eye to eye, some of the dark horse business moves that they made.

What was the best signing from Roc-A-Fella Records? Missed opportunities and more. If you enjoy the episodes we did on Cash Money and Interscope, this one will be right up your alley and we already know what it is when we’re talking about Jay, Dave, and Big. So let’s dive into it. Hope you enjoy it.

[00:02:17] Dan Runcie: All right. We are back to do another breakdown on one of the most iconic record labels, the one and only Roc-A-Fella records, and I’m joined by someone who wrote the book on one of the most influential people behind this record label. Zack O’Malley Greenberg, welcome back, man. 

[00:02:33] Zack Greenburg: Thanks for having me on, Dan, as always.

[00:02:36] Dan Runcie: Yeah, and with this one, I think it’s good to start even before Roc-A-Fella records because this label was a long time coming and there were a number of things that Jay Dame and Biggs, the founders of this record label were involved before this. So set the stage. Where were we pre Roc-A-Fella launch.

[00:02:55] Zack Greenburg: Yeah, so, you know, I think a lot of people forget, although Jay-Z is a billionaire now, a couple times over, back in the early nineties, he wasn’t even sure that he could make it as a rapper full-time. So, you know, he’d appeared on a couple tracks with his mentor jazz. Oh, this great Golden Age rapper. He had popped up kind of here and there, but, you know, really he was finding that it was much more lucrative to be a hustler.

And so he was increasingly making more and more trips outta town to New Jersey and Maryland and so forth doing his thing. And, you know, I think he really kind of saw music as a hobby at that point. so he, he did have, you know, a couple supporters, namely DJ Clark Kent, you know, one of these influential producers, at the time.

And, you know, Clark Kent really believed in Jay when a lot of people did it. And so he kind of kept trying to convince him to give another shot, like he could do this as an actual profession, and finally convince him to sort of take this meeting with Damon Dash. So he thought that Jay-Z was this just like once in a generation talent, from the musical side, and that Dame was sort of this promotional mastermind.

And then if the two forces kind of united, they could create something really special. So in my book, empire State of Mind, Clark Kent tells the story of how he convinced Jay and Dame to sort of meet up. And so Dame, of course is from Harlem, Jay’s from Brooklyn. There’s sort of like this New York City snobbery thing going on, you know, Manhattan folks kind of maybe look down sometimes on people from Brooklyn and so they get together and, Dame rolls in.

He sees Jay’s wearing a pair of Air Force 1s and he is like, okay, this guy’s cool, you know, he has good taste in sneakers, so I, can do business with him. and that was kind of like, you know, the initial hurdle was, you know, overcome and off it went. And so they struck up this really productive partnership together where, you know, Dame would kind of, help Jay Z sell, you know, they would go around selling CDs outta the trunks of cars and stuff like that.

they were trying to get a proper record deal. and they just didn’t have, like, nobody was kinda like really into the whole jay thing at the time. And you know, if you think about the music that he was making, unreasonable Doubt, it’s like very nuanced. you know, like a lot of words packed into not very many bars, you know, like the space and the rapidity of the, the flow was like kind of not what was happening at the time in the, you know, by this time like, getting toward the mid nineties.

So, basically they decided to go and start their own, and they brought in green Bigs Burke, who was kind of a silent partner, you know, another formidable hustler in his own right. And, you know, so there was the, talent, the silent partner and, you know, the promotion guy.

And you know, when their powers combined, they were Captain Planet or whatever they were Roc-A-Fella records. 

[00:05:42] Dan Runcie: And I think part of the thing with Jay-Z that made this unique was his age at this point as well, because by the time they start Roc-A-Fella, he’s already in his mid twenties, which doesn’t sound anything unusual now, but back then, the rappers that were blowing up were always teenagers.

There were always early twenties. You think about Dr. Dre, everyone from NWA, you think about Nas when he dropped I Maddock or you look at LL Cool J. Everyone is a young cat. So for Jay to then drop his debut album when he is 26, Is an ancient man, a grandfather trying to get into this game? 

[00:06:19] Zack Greenburg: Yeah, I mean, it’s like a 26 year old rookie in, you know, the NBA or in baseball or something.

It’s just like, you don’t see it. I mean, al almost ever. And when it does happen, it’s sort of like a journeyman, you know, like role player type but jay, you know, had just packed a lifetime worth of lyrics into this one album cuz he kind of viewed it as, you know, this was like a one and done, like a novelty thing.

And, you know, he really fully anticipated, you know, kind of coming up from the underworld, dropping this gem of an album and then kind of like disappearing off into the ether, like Kaiser Souzai at the individual suspects. And that, I mean, that was actually his plan. you know, according to a lot of people who I talked to around the time.

So, yeah, it was definitely not sort of the normal path, for creating an album. I mean, I think they thought that. You know, they could put out this album, it would do well and then, you know, maybe they would bring along other artists and he wouldn’t have to be sort of at the forefront.

Like he might just keep doing his thing on the hustling side or whatever. but obviously things turned out a little bit differently. 

[00:07:22] Dan Runcie: This album was also a bit of a slow burn from a success perspective. I know that many people now when they’re debating the best Jay-Z albums, the best Roc-A-Fella albums.

This one’s always mentioned as well as a few others that we’ll get into. But if you look at the commercial performance for this album, in the beginning, it was not that high. The same week that it came out, the Nutty Professor soundtrack sold more records than Reasonable Doubt. And around the same time, that summer, I’m pretty sure that Shaquille O’Neill’s album, cuz he was putting out albums at the time, also sold more than Reasonable Doubt did.

So extremely slow burn. And you mentioned something earlier about the hustle that I wanna tap into because this is one of the big value ads that Dame Dash had with this. He was relentless and we’ve all heard the stories. Many people that have met him have also seen what it’s like upfront. A lot of it speaks to his success.

But he was someone who was in many ways, notorious for going to the New York radio stations and giving them gifts, understanding, yes, this essentially is payola, but this is what everyone else is doing. This is what the people with the real money in the industry are doing. So he’s leading into that as well.

And you mentioned Kaiser Associates also makes me think about, there’s one of the music videos that Jay had from in my Lifetime, volume one where, I forget which song it was, but the song essentially, you know, the music video essentially was a spoof, odd usual Suspects where he’s impersonating the the Kevin Spacey, Kaiser Souzai character on it.

Sorry for anyone that hasn’t seen Usual Suspects for the spoilers I just dropped there. But there’s so many things that I think tie in with that and just stay consistent with who he is at the time. 

[00:09:08] Zack Greenburg: Yeah, absolutely. And I mean, I think that whole album, you know, the aesthetic was very like, maybe not Kaiser Soze, but, you know, sort of like gangster movie sort of thing and, you know, all the album artwork, you know, it’s him and like a fedora and black and white and all that kind of thing.

and so, you know, I think that, he’s been obsessed with mafia movies for like, his entire life and you don’t hear it quite as much, you know, as more recent albums. But he was kind of like living this underworld life at the time. And so I think it really resonated with him and maybe in a way that, that it, it doesn’t quite resonate now.

[00:09:44] Dan Runcie: And I think too that was in a lot of ways the theme that we saw he did in the nineties. You definitely saw Big Do It, especially in the whole life after death era, right before he passed. And I think there were a few moments that gave him the initial bump. Even after having Reasonable Doubt drop.

Jay himself was featured on the Nutty Professor soundtrack because he had the song with, Foxy Brown that was also on his album. And then he’s on Fox’s album, album a little bit later. Her debut, he’s also on, what’s the song that Jay oh, David Brooklyn’s finest, on Jay’s album. 

[00:10:18] Zack Greenburg: Going back to Callie was on there. Oh my God, what an album. Yeah. But yeah, that was not, I would say Jay-Z got the better end of the collabs. with, the Brooklyn’s Finest. I mean, that is a classic. Clark Kent produce that one also. And, you know, that was kind of like, that was another funny story from the book, like, you know, that there was also a bit of a friendly rival, mean, like they were, there were buds and all like, Jay and, and Big, but there was like a little bit of a friendly rivalry between, Jay and Dame and Puff and Big, because I think, you know, like, so the Whole Bad Boy thing was more established, by the time that Roc-A-Fella Records came about, and so I think Puff was kind of like Dame Dash, like another dude from Harlem, are you trying to be me? Kind of thing, you know, and so in order to make that song happen, I think before Jay and Big were friends, Clark kept kind of tricked them into recording the song together. So he was in the session with Big, and then he accidentally played a tape of a track that he had that was just an amazing track and Big was like, that’s great.

I wanna get on that. and he was like, no, I’m saving it for somebody else. And things like, well, who the hell else are you saving it for? And he is like, my man, Jay, you know, he’s amazing. He’s a beast. and big’s like, I don’t who, what Jay who. and so finally like Clark Kent sort of like goded him into, unbeknownst to big, Clark Kent had arranged for like Jay and Dame to be in a car downstairs.

And he was like, oh, I think he’s actually just coming in. And so he went down and he brought him up and so like Jay went in and recorded his verses, I think right then and there. And he left spaces for Big to put his verses in. and when Big went in and he listened to it, he was like, oh my God, this guy’s so good.

I have to like, go home and really think about this, about what I’m gonna put in there in the spaces that he left for me. and I think after that they were really good friends. but you know, it’s, that kind of like, good nature trickery, shall we say. that, you know, I think some of these circumstances happen when you got some egos in the building and, you wanna make some magic.

And, you know, as I recall, you know, for the chorus, Jay and Big had like become fast friends and, so like, they’re leaving the studio and Clark’s like, you know, on the final day that Biggie came and recorded or whatever, and Clark’s like, what should I do for the chorus? And they’re like, just scratch something.

And that, that was how it happened. 

[00:12:44] Dan Runcie: Classic. And that’s such a New York story, and it’s also such a 90s hip hop story in terms of how the industry worked. Having someone like, oh, so-and-so’s just downstairs, they’re gonna come up right now because you have ’em, man, how people worked. Things classic. And it speaks to where Jay was at the time too, because as we mentioned, reasonable doubt, slow bird took a while for it to get.

The respect that it deserves. But then you go to 1997, he has, in my lifetime, and that album also Slow Burn and wasn’t necessarily as highly regarded as Reasonable Doubt, but still had some songs. And you could tell that Jay was trying to navigate a few things, whether it was he had the flashy suit ever himself when he had the song Always Be My Sunshine.

He’s feeling that out. I mentioned he had the Kaiser Souzai spoof music video, but it really isn’t until 1998 where things start to change. So a few things happen here. The album Volume Two, Hard Knock Life comes out. That song, Hard Knock Life changes everything for the trajectory of that label, and that’s when they start the partnership with Def Jam.

So let’s talk about the Def Jam piece first. Can you talk a little bit about that one and break it down? 

[00:13:57] Zack Greenburg: Yeah. So. As I recall, you know, in early Roc-A-Fella they had struck this, distribution deal. I think it was with priority. and you know, reasonable doubt was they had already been selling it on their own, sort of informally out of the trunks of cars.

And then priority, you know, was distributing it. But it was kind of a disaster. They weren’t paying Jay on time and, or maybe at all, at some point. And so he just kind of went back to ’em and was like, you know, if you’re not gonna be paying me, or paying me everything, you’re not paying me on time or whatever.

Just like give my master’s back and get me out of it. and somehow that’s what happened. So that freed him up to be able to take this deal with Def Jam, where Def Jam bought a piece of Roc-A-Fella records. but again, you know, because they were buying a piece of it and not signing him to a deal. you know, he continued to own, you know, considerably higher portion of his own copyrights and, you know, possess more of the cash that came in than he would’ve otherwise. but you know, he already had the success. They already had this apparatus set up, so he had like, you know, he had leverage in a negotiation and I think, you know, even though his second album I think was kind of a dud and he would always, like, he has said in interviews that that’s his worst album and the one that he’d like to have back.

you know, he had some, heat, you know, with reasonable doubt. And then kind of like coming off the heels of Biggie’s death and, being sort of like the heir parent. it was tight with Puffy who produced the second album, you know, for better or worse. But, you know, I think that really gave them sort of the ability to get what they wanted at a Def Jam, which was like, I think part of the reason that first album didn’t do so well, and I think it was until fairly recently, his worst selling album, until sort of the back catalog began to catch up. But, what they needed was distribution those days was really important. Like you, you needed, you know, you could have Damon Dash, like Haranging, people at rec, you know, at radio stations all you want.

But in order to really have the kind of, you know, national scale, that you need to be a superstar, at least in those days, really wanted to do with the label. So that’s what they did, 

[00:15:59] Dan Runcie: Right, you needed someone that could get 500,000 units to 7,000 distribution points, and there were barriers to entry in order to do that.

And yeah, to your point, I don’t care how many bottles of champagne you try to give to Hot 97, that’s not gonna make that happen without it, right? The thing that I always think about with this ever though, is the terms of this deal, because at least what we’ve seen publicly was that Def Jam had taken a 50% stake.

In Roc-A-Fella records, and it was for one and a half million dollars. And that number always stuck out to me a bit because if you look at some of the other deals that had happened in that era, you had masterpieces distribution deal that he had done with the same priority records that Roc-A-Fella had their deal with.

But Master P obviously had a much more favorable distribution deal with splits in his favor. And then similarly, that same year, 1998 Cash money, does their distribution deal with Republic Records? Of course, Def Jam is a different unit and Roc-A-Fella was in a very different place. And we know that Jay-Z had always talked about ownership and it was important to him.

But it’s a interesting reflection of just where things looked at in the landscape because it’s easy to look back in Jay’s career in hindsight and think that, oh yeah, his first album was a classic and then Hard Knock Life comes and everything is just up and up. But there was still. hierarchy and there were other artists that were getting more favorable deals, more ownership for their music, for their record labels.

And Roc-A-Fella still got something that was somewhat favorable, but still not at the same level of some of those other people in the mid to late 90s. 

[00:17:40] Zack Greenburg: Yeah, I mean, that’s a really interesting point, right? I mean, Jay obviously is this brilliant businessman and, you know, Damon and bigs aren’t too shabby either.

And yet it was a good deal, but it wasn’t, anything like, a cash money or no limit in terms of the splits, and what they were doing. So, yeah, I mean, I think to your point, you know, those other acts, had kind of like a more established operation, you know, Jay was one guy with one album that didn’t sell very well, that was kind of critically acclaimed, you know, so it was like A bit more of a risk perhaps, on Def Jams parts, they weren’t really risking that much capital on them. So, you know, I mean, and I guess I wonder if that initial deal had been more favorable for Roc-A-Fella, if they had managed, to have, you know, the kind of splits that Cash Money and No Limit had might they have stayed in business together longer? You know, in a way it’s like if the pie that you have or like if the one big pie, and, you know, if you’re a slice of the pie that you’re sharing with your two business partners is that much smaller than it is, than, you know, let’s say the Williams brothers were sharing a cash money, you know, maybe you feel, a lot more restless and, inclined to go elsewhere, but we can get to that later.

[00:18:59] Dan Runcie: that’s a good point too, because if Cash Money is still in business. And we know cuz we recorded that episode not too long ago, but Birdman and Slim are still getting tens of millions of dollars per year. It’s essentially a cash cow asset that they have. Def Jam is still collecting for Roc-A-Fella, as is universal. And I know that Jay and Damon Bigs do have their splits, but it’s not the same because they eventually did sell the other half of the record label to the parent company Def Jam. I think it was Island Def Jam at the time that that deal happened. But it changes the dynamics a lot. But with the story though, we are getting to the point where Roc-A-Fella is clearly on the way up.

And I think there were a few things coming that did set things up for them. But one thing that I think was a big difference maker for them around 1999 was them wanting to go on tour and. Have their name out there. So 1999 they have the Hard Knock Life tour and at this time it was pretty rare for, all Hip Hop Act to have a nationwide arena tour that happened because at the time they had past shows or whether it was at Run DMC shows or other things in the late 80s, early 90s, and cause of violence and because of things like that, all these promoters and all these venue operators were so scared of hip hop.

So you had Smoking Grooves and other festivals like that in the mid nineties where they always had to pair you with the R&B actor. They had to have two folks together. I know that Bad Boy had its, arena tours as well, but they always had the R&B acts that were there, so they needed to, they were really trying to do something different.

But I think this is where Dame’s Magic came to life because he was able to really control the narrative and be out in front with how they were making sure that violence wouldn’t happen, whether they had their own security on top of whoever was there. They had the fruit of Islam that was at each of these shows standing there to have the, bodyguards there as present.

When the reporters came into the trailers to see what they were doing on tour, there’s this iconic video of Tie Tie and he has videos up and this VHS tapes up of, oh, you think we’re just watching gangster flicks? No, here we got Goodwill Hunting right here. We got Brave Part, we got as good as it gets.

Like we’re here watching videos like anyone else. And with that and even, I think they did something that was either, either donating money or something as well cause in Colorado, because they had a show right around the same time that the Columbine shooting had happened there. So there were a few things they’d done there.

And I think that tour in a lot of ways helped. Not just the Roc-A-Fella crew, but all the other folks that were associated with them that came along like Red and meth and Ja Rule and others. But then after that, we then saw the Up and Smoke tour. We saw Rough Riders and Cash Money go on tour. And I think that tour in a lot of ways helped propel them into that next level to continue to have a lot of that success.

[00:22:06] Zack Greenburg: Totally. And you know, and I think it wasn’t necessarily reflected in the bottom line. I mean, I don’t remember what the gross was, but, you know, 18 million I think. Yeah. Like Taylor Swift probably grossed that in one show at, 

[00:22:20] Dan Runcie: I think he made that in two of the three nights at, 

[00:22:23] Zack Greenburg: Yeah, definitely, definitely over a weekend in the Meadowlands, but yeah, she probably had definitely, let’s say, definitely crushed it in her like little weekend did in the Meadowlands. But you know, and so obviously if you’re grossing $18 million. You’re probably only taking home, you know, 10 of that after cost, maybe like, probably more like, you know, I don’t know, seven or eight. and then you’re dividing that up amongst however many people. There were a lot of people on that tour for like a fair amount of tour days, so it did not work out to a lot of sort of take home pay per show, but it really kind of opened the door. I think in the aftermath of the death of Tupac, Biggie and like all of this, you know, sort of, like moral panic around hip hop and violence and all of the, you know, whatever Tipper Gore stuff, you know, that this was sort of like a reminder that like, yes, hip hop Acts can go on tour and it’s gonna be fine.

And like that, you know, that had been done in the past and, run DMC and what have you. But, you know, NWA had gone on tour and, you know, had a big national tour. So there were other examples before, but I think people were like, kind of freaked out about hip hop in the national zeitgeist at the time, and this kind of really helped to kind of reset things. And, you know, opened the door for other rappers, but, you know, for Jay-Z himself down the line, you know, I mean, he’s been a really prolific touring act and I think he’s always been really clever, about it because, he’s like, even now, like he can sell out arenas, but, you know, he’s not like, I don’t know, he sort of can’t necessarily do, he can’t sell out stadiums by himself, that’s for sure. And there was a time when he couldn’t sell out arenas by himself. and there’s probably a time when he couldn’t sell Amphitheaters by himself, but he always goes around, he brings somebody with him and he’s got a really good kind of, level of self-evaluation and he’s like, you know, he doesn’t let his hubris get in the way of like, I can sell out whatever, whatever.

unless he knows he can, you know, he, he’s very accurate in that assessment. And if he can’t make it, then he just brings somebody with him. He brings Eminem with them. you know, he goes out with Beyonce for the stadium tour. So, you know, Justin Timberlake with him. Yeah, yeah, exactly. Exactly. So in a way, I think that tour was kind of the beginning of that.

And, you know, how he could, see some synergies by mixing and matching with other artists 

[00:24:35] Dan Runcie: And that tour too Hard Knock Life tour. He showed signs of that awareness there. There’s this iconic clip when Jay-Z was on the shop a couple years ago and he’s talking about the show. This was shortly after DMX had passed away and Jay-Z was going on tour in each of these nights after X and X’s shows, you know, he’s taken off his shirt, he’s doing prayers at the end.

So you have people that are laughing, you have people that are crying, then people that are screaming and then they come out and they’re like, oh, now you go like pointed to Jay-Z. And I mean, one Jay’s storytelling of that is good. When we post this episode, we’ll definitely share this clip in there, but two, it showed this awareness that people have spoke about of, and it’s also what you’re saying, even if he may not have always been the central act and another running thing that people have said over the years, what year was Jay-Z, the top guy in hip hop?

And I think that is a very debatable thing, but it’s the longevity and that’s the thing that speaks to it. And how he’s been able to stay through that over the years. And because he was always that core piece, like we said, price is probably one of the reasons that they didn’t get a no limit or a cash money type deal.

It really was just him. I think there was that one R&B album that Rocefella hadn’t released in 1997, but didn’t really go anywhere with that artist. So things didn’t really pick up until late nineties, early two thousands. And you start to see more of the artists on Roc La Familia, and they’re really able to spread their wings in that way.

[00:26:10] Zack Greenburg: Yeah, I mean, another thing to remember, at the time, you know, especially, I think it was 98, 99, that was when, you know, Def Jam. So I think Def Jam had already taken a pretty significant, institutional investor, but, they were selling the company or like maybe the remainder of the company or most of the remainder of the company.

There’s this really, really big deal happening. and I forget which sort of, European entertainment conglomerate was it Bertlesman or It was like, was, something that’s since been reconstituted or, or whatever. But the, the deal was gonna happen and you know, the deal was gonna be for whatever multiple of revenue, that Roc-A-Fella had or not Roc-A-Fella, that Def Jam had produced in the prior year.

And so for the, I think it was the calendar year of 1999. And so, Lyor and Russell just like leaned really hard on Jay and DMX and they were like, we need you to put out like two albums in 12 months because we’re just gonna get a multiple of that. And I don’t remember the exact advances that, that were given, but you know, I’m sure it was considerable.

And so, you know, they were able to put out like each of them two really killer albums in the span of like about 12 months each. which is like kind of unheard of these days, right? I mean, Jay-Z goes, is like five years between albums now and, I think that was, volume two and volume three for Jay-Z.

And I think for DMX, it’s dark and. 

[00:27:38] Dan Runcie: Dark as hell and hot and then flesh and my flesh blood. And then, and those were like, like, and then there was X was the third. Oh, then there was X. 

[00:27:45] Zack Greenburg: That’s right, that’s right. So those were like, like two, like for each of them to 

[00:27:49] Dan Runcie: a year and a half spare albums.

[00:27:51] Zack Greenburg: I mean, yeah, back to back, you know, man, like to have that much, sort of creative energy to do it so quickly, and to have it sell so well, I mean, it is quite a feat and you know, and they, personally enriched Russell and Lyor and Rick Rubin, like, I would say quite substantially cuz it just drove up that multiple.

And, yeah, I think a lot of people kind of forget, how critical they were, you know, to that process. But it probably also caught thinking like, Why am I working so hard to make somebody else, you know, I’m getting rich, but they’re getting wealthy and, I think the gears are continuing to turn for him at that point and he’s like, Hmm, how do I kind of get to be more in their position, right?

[00:28:32] Dan Runcie: Cuz I think at this time, this is when you start seeing more of the Roc-A-Fella expansions in a few ways. First Dame is already thinking about ways to extend this brand. You see Roc films, Streets is watching comes out in the late nineties and then they put out a whole documentary about the Hard Knock life tour as well.

And they start selling that as the DVD Rocawear comes out. And we’re gonna do a whole episode about Rocawear eventually, but, you know, Rocawear itself. And then you also just start to see more and more product coming from Roc-A-Fella that isn’t necessarily from Jay himself. And I was looking back from a timeline.

And this is one of the unfortunate things about Roc-A-Fella, we’re gonna get to this, but right around the time they split, you could argue that they were just continuing to go up and up and up with the releases every year. Like this is the 12 month stretch that they had where I think they had the highest products.

Starting in February 20th, 2003, you had freeway drops, Philadelphia Freeway, Dipset Drops, diplomatic immunity. Joels has his debut album. Jay-Z drops the Black album, Memphis Bleak drops his, and then top of 2004 Ye drops College Dropout, Young Guns drops their debut. And that’s all in a 12 month span.

That’s some no limit cash, money level of dropping albums. And so there’s so many hits and so many memorable songs that they had during that stretch. 

[00:29:59] Zack Greenburg: Yeah, absolutely. And you know, I think that if, you know, we were talking earlier about the splits and so forth, but it’s like, can you imagine. If they had the kind of splits to catch money it had, when you have all those albums coming out and, you know, yeah, I think it really would’ve changed things.

Not only that, but you know, to own the masters of all those artists, which you probably would’ve in those days. you know, to have like a hundred percent or something close to it on all those artists with all those classics. you know, it would’ve been very hard to walk away from, you know, as they eventually ended up doing.

[00:30:33] Dan Runcie: And I think what you mentioned earlier, probably alludes to this, right? Because if there’s enough of the pie to these split between the three founders and everyone else, and they’re the one accruing the assets from what they have, then maybe Jay and Dame are more likely to figure out their differences in a way to make things cook because it’s working for everyone.

But when you’re still paying Def Jam in on top of that, or you’re still paying island def jam in on top of that universal even more money, it’s tough to justify that. And I think this is a good time to talk about the split. The infamous split between Jay-Z and Damon Dash. You could start to see that the two of them were going in different areas where Jay-Z was wanting to be really focused in on what he was doing from a music perspective, wanting to expand there and wanting to just do different creative things.

But Dame had his own approach, and we talked a little bit about that with, the films and the sports and other things too. But he also wanted to do things his way. He was starting to get a little bit more spotlight. And then there’s that infamous clip of them at Summer Jam 2001, where Dame Dash is in his full element.

And Jay-Z’s just like expressionless. And that clip is often looked at as like you knew from this moment. That these two just were necessarily gonna be at the same page because this is 2001, Jay-Z’s are drop about to drop the blueprint, his masterpiece. And granted, you know, he could have just been in the zone or whatever, but it’s definitely an unfortunate thing because granted, Jay-Z was able to reach further heights, but you never know what could have happened.

You just look at how much Rocawear ended up selling for you. Look at the continued success, the momentum, and I think what it boils down to is to. People that had different philosophies where it makes it tough. Jay-Z was a bit more focused on wanting to be rich. He was willing to do partnerships with others if everyone could eat and have a piece of the pie. Granted, he still wanted ownership, but as you’ve written about before, he has his perceptions on underdog brands and how he could move like a private equity executive and make the right investments. And even the m and a deals he’s continued to do today, his live nation deal is the element of this.

But Dame was a bit more wanting to be king. He wanted to have his stamp on things. And I think you see that even now today with Dame Dash Studios, Dame Dash, this, like, it’s very important for him to be able to have his kids and his other folks around him be able to work with him and be the boss, not necessarily wanting anyone to tell you what you can and can’t do.

And that infamous Breakfast Club interview that they had, I think it was 2015 when he’s yelling at DJ Envy and Charlemagne about, well, they gotta report to whoever at Power 105 and that’s their manager, that they’re not a real boss, is an element of that whole dynamic. So it’s frustrating that it happened, but it’s also not surprising.

[00:33:26] Zack Greenburg: Yeah, I mean, I think, you know, Jay has kind of adjusted his views on ownership and he said recently, I mean, he’s sold some of his big brands, or sold half of it into, a JV with like LVMH or you know, or whatever. And he’s very much of the mind of like, well, I, you know, 50% of like a billion is a lot more than a hundred percent of, you know, a couple hundred million, and I think Dave, that’s 

[00:33:51] Dan Runcie: that you did with Kevin Hart, right? 

[00:33:53] Zack Greenburg: Yeah, yeah, yeah, exactly right. So, and I don’t remember the exact quote, but maybe you could, maybe you guys can pull it up, but I don’t think Dame really ever got that. He was always like, well, I want a hundred percent, you know, and so, you know, he ended up with a hundred percent of like, whatever, you know, seven or eight figure amount that he ended up with.

But he could have had, you know, 50% or 30% or something of like billions of many billions probably. But you know, just to kind of like, I think there was a precipitating moment that sort of like was the end of, Roc-A-Fella a s it was, a partnership between the three of them.

But it really could have been anything. it was headed that way for a couple of years. And, you know, I think what it comes down to, is that, I don’t know. I mean, I think that Jay also recognized that Dame was very, very valuable. The skillset was especially valuable in the come up.

And, you know, like when you are not well known, you need somebody to go in and yell at somebody at the radio station. you know, but then when you get there, you need somebody to like not yell at certain people, you know? And, when you get to that next level, and sort of Dame, you know, didn’t adjust, To that.

And, Damon was sort of Damon or wherever he was. And it was great in one situation, not great in another situation. So I think the precipitating incident was basically when, you know, after this sale, which ironically Roc-A-Fella helped, boost, you know, the Def Jam sale. There was a reshuffling of executives, which is like so complicated.

I’d have to go back to that chapter of my book to, to look at it. But the gist of it was the role of president at Def Jam, opened up and, it was offered to Jay-Z. And so, you know, Jay-Z, this is something that he had sort of, it’s this like great prestige job. something that he’d always been wanting.

And I don’t think he wanted it, like, this is my dream job that I’ve always wanted. As much as it was like, if I can do this, be a CEO, this opens the door to so many other things. And it will really sort of entrench me as not being pigeonholed as an artist. And, it was a no-brainer and of course there was no way to do this without, stepping on Dame’s toes.

So, you know, there’s this whole great drama, and I think, you know, the wheels started turning when Jay-Z was, you know, on, on a yacht in the south of France with like Beyonce and Jimmy Iovine and Bono or something and, kicking it. And, you know, there’s some executives there. Some conversations were had, I think at the same time back home, Dame, like elevated camera on to VP level at Roc-A-Fella without consulting Jay.

And it was this kind of like big scandal and when Jay-Z came home, he was like, no. And he kind of demoted him. So there was some awkwardness there. but you know, I think then that Jay kinda like accelerated his, push toward this CEO role, and when he got it, it’s like, all right, you know, sorry Dave, I’m your boss now.

I mean, because of course Def Jam was, but Roc-A-Fella, there was really. There was no way for it not to be structured like that. so, you know, when that went down, of course, like Dame immediately, you know, quit or left or whatever, and, there was a hot minute where he started the Damon Dash Music group within Universal, but, you know, then he kind of like kept doing the same thing and kind of yelling at the wrong people.

And, and so that didn’t really go anywhere. And, you know, the thing kind of fizzled out and Jay offered to, I think he wanted to give, at the time, he wanted to give, Biggs and Dame, like all of his preexisting masters in exchange for exclusive ownership of Reasonable Doubt. they said no. but of course, you know, I don’t know that the Black album had gotten as big, is it?

You know, I hadn’t like really fully blossomed into what it, what it ultimately was at that time. And there’s like all this other, so anyway, I mean, there’s a lot of like trades being offered and you know, people sort of like, you know, it’s like the guy in your family in football league, your fantasy baseball league.

You kinda like overvalue his own players. Think I’ve made this analogy before, but, dude, come on. Like, you know, you’re running back, just got injured and offering you my extra running back for this wide receiver who you’re not even music anyway. it didn’t really work out.

Everybody got all pissed on each other, you know, at the end there’s bad blood. so th there’s this great moment that Dame talks about how, shortly after all this went down and they’re like in the elevator at, I guess the Universal Museum, that Def Jam was housed in. and Roc-A-Fella had been housed in or something.

And they’re like bumping each other in the elevator and Dame is wearing a state property shirt and Jay C’s like in the suit. And Dame’s like, man, you know, things are really different now. Like, dude, you changed, you know? so, you know, I don’t know if Jay changed so much as like Dame didn’t change, you know?

you could argue the problem was that Jay changed, but you could also argue that problem is that, that Dame didn’t. And, you know, I mean, to some extent like power to him, you know, be you. but Jay, you know, in the way that I think you know, he’s constantly changing. He’s restless, he’s always, everything is a chessboard.

He’s always evolving, you know, I think ultimately there was no way to stay locked into a partnership with someone who wasn’t kind of willing to change with them. 

[00:38:59] Dan Runcie: One thing you mentioned there made me think about how they think about things and where they are from a strategic perspective, Dame is very much your early stage startup guy.

He’s great for the pre-seed era. He’s great for when you’re even in the seed stage, maybe even series A, but once you get to that series B, C, you’re starting to get some higher level executives. You’re getting more talent, you’re gone to bigger things. You can’t operate the same way and no different. How those organizations often need to rotate and think about leadership.

That’s essentially what in many ways was the opportunity there at Roc-A-Fella. And there’s nothing wrong with being very successful at that pre precede seed stage. I don’t think Roc-A-Fella would’ve got to that point if it weren’t for Dame hustling in many absolutely ways, whether it was on tour radio, and I think a lot of his success traits have been carried through and things we’ve seen celebrated and leaders in tech and people that do things that don’t scale that very much is Dame Dash. That next level, though, is where things did get a little bit tough because the label’s clearly getting ready to go to that next level, and they just had their tensions there.

The thing that was unique though, about their tensions is that the artists themselves that were on Roc-A-Fellas started picking sides in terms of who they wanted to be with, who they were gonna side with, Jay versus Dame, and as you mentioned, Dame was the one that had elevated Cameron, who was the leader of Dipset at the time, to that VP level.

That then brings everyone from dipset under his umbrella, but Ye, who had just dropped the college dropout and he was the one that was always trying to make it. He then signs with Jay, he also has a very memorable interview on the Breakfast Club where they asked him about this, and Ye was the one that was like, me and Dame we’re the same. We think the same. This is how we act and go about things but I could learn more from Jay. He knows how to talk to people and he uses Jay’s iconic lines. He’s like, Jay knows how to move in a room full of vultures. That’s just how he is and sometimes I be talking and saying the wrong things, which is a very ironic thing.

I don’t know if Kanye himself would admit that now, cuz that very much is a self-serving prophecy. I do think that there’s a lot of truth in that, and just how things ended up shaking out for both of them. You saw the moves that everyone continued to make, and even though ye has definitely been quite polarizing in the public spotlight, a lot of the moves that he continued to make, whether it was with Yeezy or with the partnerships he’s had, I do think stemmed from how he looked up to his own big brother in Jay.

[00:41:42] Zack Greenburg: Yeah. And he could have easily gone with Dame, right? I mean, you know, Jay wasn’t so great to him early. Jay didn’t believe in him as a rapper, he kind of wanted to keep him as a producer and Dame was, I think, the one who really advocated for Kanye as a rapper. but you know, I think Kanye, in his, you know, like more self-aware moments can say things like, oh, I think I could learn more from Jay.

He brings something to table that I don’t have, for Dame, I think the difference between Dame and Kanye is that they’re very similar, in a lot of ways. But Dame isn’t an artist. like, let’s say a generationally talented artist. And so people will not put up with you if you’re an executive. And you bring along those headaches in the way that they would put along, put up with you if you’re a generational artist and you bring those headaches. And I think that was sort of like also, something that did Damon. And you know, in a way I think Damon Puff had a lot in common like they can just go in and kind of bulldoze their way into something.

but Puff has that, that like other level where he can sort of like turn it up and down and, you know, to fit the situation. and is like more of a chameleon than Dame is. And Dame’s just kind of dame all the time. so, you know, those are sort of the, personalized to play. But you know, like one person who gets lost in the shuffle here is Cameron.

And because that was sort of the prime of his career that got like, entangled in this sort of higher level beef. but you know, you think about that album, come home with me and Hey man, like, I mean, Cam was really on fire, going into this whole situation. And then he got kind of like, I don’t say like exactly lost in the shuffle, but almost lost in the shuffle.

You know? and you just kind of wonder how his career would’ve gone, you know, let’s say if, sort of he hadn’t been like Dame’s guy, you know, if what if he had gone to Def Jam? You know, what would that have looked like? could he have been on the level of somebody who signed? You know, like, I don’t know.

I mean, around that time, I think, Rick Ross signed a Def Jam, was it? 

[00:43:41] Dan Runcie: Ross, Jeezy, yeah. 

[00:43:43] Zack Greenburg: Yeah, like, you know, I think certainly has, you know, comparable ability, Tyler and those guys and, you know, I think both of them went on to have, You know, sort of like more longevity. but like, you know, I think, some of the Dipset classics and some of the solo stuff too, I mean, it’s pretty unbeatable.

So, you know, I just wonder, he’s had a really good career, either way. But like, you know, I don’t know that he ever like, broke through that next level, consistently, you know, to the point where he could just kind of stay there indefinitely. And, I wonder if he might have, if things had kind of gone differently in the Jay-Dame scenario, 

[00:44:21] Dan Runcie: The man had men wearing pink. He started his own fashion. Yeah. Unbelievable. Yeah, that’s true. Unbelievable. With that, I think it’s a good chance to hit through some of these categories, cuz I think you’re jogging my memory the few things here. what do you think is the best signing that happened under Roc-A-Fella? 

[00:44:39] Zack Greenburg: Well, I guess you can’t count Jay if he, you know, co-founded Right Label.

But, you know, I’d say probably Kanye. it’s hard to top that. And when, you know, when you think about those first few albums, you know, I mean, he brought an element into hip hop, into the mainstream that just wasn’t there. and, you know, I don’t think, you know, if you hadn’t had Kanye, in the pink polo, and you know, talking about his feelings, like, I don’t know if you get Drake right.

I think that he kind of changed the discourse. he brought hiphop to the mainstream and then he also like brought a different sort of voice to hiphop, And it was fantastically lucrative, obviously, for everybody involved. So, yeah, I agree with Kanye, for sure. 

[00:45:22] Dan Runcie: Yeah, agreed. And then just given the longevity there, even into the early 2010s, still putting out records under the Roc-A-Fella Records umbrella that still went back to them.

And longevity that lasted longer than most of the people that were assigned to that label. So I think it has to be him. Best Business Move made, I know we talked about a few of them, but what do you think is the best business move that to come from the Roc-A-Fella era? 

[00:45:47] Zack Greenburg: Hmm. I mean, it’s funny now that we look at it, I mean, in a way, know, the deal itself that set up Roc-A-Fella was not, you know, it wasn’t a bad deal, but it was not the best, move.

It wasn’t the best kind of financial arrangement. you know, I mean, Rocawear is kind of an offshoot. Maybe that’s cheating, but I’m gonna go with Rocawear because I think in some ways they’re like, well, we can’t get a hundred percent of the money on this thing, so we’re gonna create an adjacent brand that’s like very clearly associated with it that we can really monetize fully.

And you know, I mean they got paid, I mean that, that company was doing hundreds of millions in revenue and they sold it for hundreds of millions. So, you know, I think they made more off of Roca wear, than they ever made off of Roc-A-Fella. So I’ll go with Rocawear, we can talk more about it when we do the full Roca too.

[00:46:36] Dan Runcie: I know. Yeah. I’d Rocawear as well. I won’t go into the company itself cuz Yeah. We’ll get into that in the next one. But I do think the good thing about that was it was a precursor to how artists now are thinking about their own revenue, their own business models, right? How they’re using streaming, how they’re using anything else that gives them a platform.

Use that to grow your audience, use that to grow the awareness while generating money for that, establish the base. So some of those other business units were likely more influential, thinking about them doing the deals with Def Jam and then them having the hard knock life tour. But I do think Rocawear was the best business thing to come through there for sure.

[00:47:18] Zack Greenburg: And just a s like a subset of that. I think the philosophy that was embodied by Roca wear, you know, the idea of like, they wanted to go Roca wear started because they wanted to go. there, there was this Italian, knitwear brand. iceberg. And they like went to the iceberg offices and said, Hey, can you give us some free t-shirts or something for wrapping about your thing?

And they’re like, or no, I think they wanted an endorsement deal. They wanted some cash for an endorsement. and then the executives were like, we’ll give you some free t-shirts. And, Dave was like, this is stupid. Let’s go start our own thing. So, but I think that was really the beginning of, you know, like, I’m not gonna give, free publicity to other brands.

I’m just gonna go start my own thing and rap about it. Like other rappers have done it. But, it became so pervasive for Jay-Z’s mindset. It wasn’t just like, I’m gonna do my own clothing line and I’m sorry, I’m gonna do my own champagne. I’m gonna do my own cognac. I’m gonna try to do my own car.

I’m gonna try to do like a freaking video game, you know, he was involved in so many things that kind of sprung from that. so I think the implications were much broader than just, the clothing aspect. 

[00:48:28] Dan Runcie: Agreed. Next one here is the dark horse business move. So one that we actually haven’t talked about, but I do think is one that Roc-A-Fella definitely lead into was the Jay-Z and Nas beef.

The controversy that this was able to stem and start, I briefly mentioned Summer Jam 2001, but everything from then and just the drama from there, the two of them back and forth, Jay drop in takeover that, NAS drop in Ether, that whole back and forth was able to then create so much interest. They had all those beef DVDs that were g blowing up in the two thousands, I think largely came up cause of how they were able to reignite beef from essentially the biggest beef that hip hop had seen since Biggie and Tupac several years earlier.

Yeah, it was huge and the level of. Bars that I think we’re able to get the songs they’re able to get back and forth. Just the impressiveness of Nas essentially taking on this whole entire unit by himself. People can debate whether or not who won and lost, whether you’re looking specifically from a battle perspective versus who won in the long term.

But we eventually see them come together on American gangster and they continue this f familiar relationship ever since. But I do think that this was the height of the time to really sell controversy. Obviously we saw 50 cent and others continue to do that too, you know, their own, putting their own flavor on as well.

But I do think that Jay-Z and Nas Beef still was one of the little crown jewels that they had with this. 

[00:50:05] Zack Greenburg: Absolutely. And, you could tell that it was like there was real enmity there. but also, you know, the fact that it, it never turned violent, I think was just. I think it was really good for hip hop, and I don’t think it was ever going to turn violent, but I think again, there was just this kind of like national paranoia around hip hop and, there is, you know, in waves.

I think it was just a, good reminder that you can have like a spirited dispute and, it’s okay and it’s entertainment, you know? and it’s, nothing that anybody needs to be afraid of. So, you know, of course like credit to Jay and Nas for resolving it amicably, but man, you know, like just being in New York and that time and like the Barbs going back and forth and man, I think that’s the only time that, like a beef has gotten so nasty that, a rapper’s mother has like, made him basically apologized for saying something mean, which, I think that was Jay-Z’s response to Ether. I think Ether was sort of like the pinnacle of it and Jay-Z’s response to it was like, not quite as good, like, how do you top ether? but I think Jay-Z’s was just like, viscerally, like, you know, won’t get too deep into it because if, Jay-Z had to like, call in to apologize for it, you know, I dunno if we can even talk about it on a podcast.

But yeah, I mean just, to have that end, you know, like very amicably I think was just so good for everybody involved. And then, you know, I think it’s really fun to watch, Jay and Nas as their relationship has evolved. And, you know, Nas was sort of always like the one who was sort of behind, when it came to the business of things.

and then, you know, like he really was music first all the time. And, you know, I think some people thought that he would never really kind of blossom as a businessman, but then, you know, he became sort of the leader, within hip hop entering the venture capital world and, you know, created this great, Queensbridge Venture partners and, you know, invested early and just about every startup you can name and has had all kinds of fantastic exits.

And, you know, I think it’s so funny that Jay-Z then started MVP, you know, Marcy. So it, it’s like definitely like a nod to Nas, you know, each of them naming their venture fund after the project where they grew up. So, I think that’s super cool. And, you know, they still like drop these little subliminal, I don’t know, like references, where you could tell they’re kind of like tweaking each other, just like.

You know, like sibling rivalry kind of thing. which is I think, really fun to watch. And, you know, I think that there’s some friendly competition around deals and so forth these days. But it’s just, it’s so fascinating to like, watch the evolution from this real knockdown, drag out, very personal beef, that occurred, you know, to now like, sort of like comparing deal flow.

And I think it speaks very positively toward like, the evolution of the business of hip hop. 

[00:53:03] Dan Runcie: Definitely. You think about things that they wrapped about in their most recent, songs that have been popular, right? Like Nas’s song where he calls himself Cryptocurrency Scarface, or Yeah, yeah.

Jay-Z. what was that line in God did with Khali where he is like, oh, we had cap tables, not that cap table, or something like that. I mean, he’s clearly leading into that stuff. What do you think is the missed opportunity if of any, from Roc-A-Fella besides the split, cause I know we’ve talked about that, but there any other missed opportunities, especially from that 96 to 03, 04 range?

[00:53:37] Zack Greenburg: I think it’s Armadale Armadale, like, and you know, that kind of came to be, I think of anybody that was more Biggs’s pet project, than Jay or Dame. Although, you know, Jay was kind of trying to make it happen. He would, he had it. If you recalled the MTV Unplugged album, which as actually might be my favorite Jay-Z album of all time. It’s kind of cheating cause it’s not a studio album, but, it’s so good. He’s backed up by the race anyway. He’s like, some point he’s like, I need to stop for some Armadale. I need an army break, you know, he was really trying to shout it out everywhere he could. But already when they started doing that, you know, they were on the outs I think.

And, I think Jay-Z wasn’t fully invested in it because why would he get fully invested in it? And then another thing that he was partners with Bigs and Damon, I don’t think anything against Bigs, obviously. And I think they’re totally cool now. And they’ve, been doing some stuff together more recently.

but like, why would he go do that when he could just wait and then do something on his own? But, you know, I mean, Armadale could have been cRoc, right? if they’d done it right, there’s no reason that it couldn’t have been. I mean, it’s the same formula. It’s like European unknown, whatever.

And then, you know, put it in videos, put it in songs, and, you make it, you know, whatever it’s gonna be. And you know, we’ve seen what Jay has done with Deuce and Armando Biac, so we know he can do it. It’s not only Puff who can do it, only a few people who can do it. Levelly can do it, but like Jay and Puff can do it and done it. And Jay could have done it with Armadale, just, you know, At the timing just didn’t quite work out. 

[00:55:03] Dan Runcie: I think Armadale had one memorable shout out from the Jay-Z song. It was, excuse me, miss, right where he is talking about Armadale popping off. but that’s also the same song. I think he gave Cristal a pretty big shout out there where he is like, it’s not Cristal, it’s Cristal, right? But then a couple years later, he is like, no like obviously we’re done with Cristal because of, you know, comments, racist comments that the founder or the CEO had said at the time, my missed opportunity is one that highlights something that I think Jay-Z did well, but it probably could have done more of.

And that’s movie soundtracks. If you ask certain Jay-Z fans, I do think that they have American gangster as one of their top Jay-Z albums, as they should. It’s a great album. I honestly think the album’s probably even better than that movie is in particular points. But Jay-Z, so that movie, that soundtrack comes out 2007.

He missed, I think an entire wave of times when movie soundtracks, in my opinion, were even, were just bigger deals than they are by even 2007 and even later on. And now I think it’s very hit or miss that you could even get a soundtrack to that level. But especially during the Roc era. And I know that he had songs that were popular on the, but really being the mc behind an entire soundtrack in that type of way, I think could have been there probably could have been more opportunities to do something like that earlier on.

[00:56:26] Zack Greenburg: Oh, I like that’s a really deep cut. 

[00:56:28] Dan Runcie: So a few more things here on Roc-A-Fella, Well, we’ve seen just continued spats back and forth. Not necessarily jabs, but just comments back and forth between Jay and Dame. It’s been nearly 20 years since this split. We’ve definitely seen more from Dame than Jay, and it’s one of those things where it does become a bit sad to see and frustrating to see at times and not be expecting to be best of friends.

We have seen Jay-Z say things that are quite complimentary. When he got inducted into the Roc and Roll Hall of Fame, he did shout out both him and Biggs and say, Hey, this wouldn’t have happened without either of you, regardless of what had happened, you know, in our past. Gotta give you guys both shouts for that.

But then we’ve also seen Dame say things during the years, and I think he’s. Alternated on whether or not he’s wanted to speak on them and stuff. But it’s one of these things that is a bit frustrating to see because I think about it when I think about NBA players and how they’ve had issues over the years.

Kobe and Shaq, of course, infamously, they continue to talk about each other for years and then eventually they came and they had that sit down chat on TBS, right? Where they’re talking back and forth. If they and Dame ever did something like that, they don’t even have to go do it on some platform. They could do it on their own thing.

It would be box office. It would be great to be able to see that and just see how, then hear them talk things out. Because even another NBA thing, Kevin Garnet and Ray Allen of course said, had their infamous dispute because Ray Allen went to go join the Miami Heat. Kevin Garnet, very intense, hated that that was their rival.

But then after Ray Allen had walked past him at the 75th anniversary thing last year, that’s when KG was like, okay, what if Ray Allen passes the same way, passes away the same way that Kobe Bryant did? I would, yeah, be very upset with myself if that ever happened. So it’s like, Hey, you guys are both in your 50s now.

You never know what can happen. We’re seeing a lot of artists and a lot of entertainers that we love that are around the same age as Jay and Dame have unfortunate health scares. If there’s a way that, not even that it needs to be public just for our consumption, but if there’s a way to see them ever rekindle things at that perspective, that would be nice to see, at least in a public way.

[00:58:44] Zack Greenburg: Yeah, I mean, I think it’d be great. I just don’t know. I just don’t know that it would happen, you know? I mean, I think that Jay has so fully moved on. I just don’t know if, he would do it. and I think just sort of like the nature of Dame, is to sort of like want the spotlight and I think James just kind of like wouldn’t want to deal with that, you know?

I think Dame would want to come into it with sort of like equal billing and it kind of goes back to a strategy that Jay has had, throughout his career, which is like, you know, I think he learned this when he had the lion. I’m about a dollar, what the fuck is 50 cent? And that was like when nobody knew 50 cent was, and it kind of catapulted him into the conversation even though within hip hop Dash is obviously.

You know, really well known and, let’s say highly respected by some, maybe infamous to others, but, you know, he’s definitely a known quantity. I think in the national conversation, Damon Dash is not known. And I think that now that Jay-Z is in this sort of international phase of his, you know, of his career, like that same philosophy might apply.

Like, I don’t want to sort of like give free publicity to somebody, you know, for no reason. So, you know, I don’t know. I mean, maybe if you were in some kind of legacy burnishing mode and like, you know, mending fences or something like that, but it might have to come down to some kind of like, somebody has a health issue situation, you know, for it to really like resolve it in that way.

And I just don’t know, like again, in terms of it being, you know, like box office, I mean, it would be great versus, you know, yeah. but I don’t know that people would tune in for like a Jay-Dame special or something like that. And I don’t know that Jay, that’s what Jay would want for his brand. I think, you know, Jay-Z wants to be like Jay and Bill Gates do a one-on-one sit down.

Like he, I don’t think he wants to like, go back to that period of his life. 

[01:00:46] Dan Runcie: I think that’s fair because I think that’s a good clarification because it would almost be like, it, maybe it would be less like the Kobe and Shaq thing would almost be more like Jordan and Pippen, where like Pippen is the one that’s saying like, wild shit about Michael Jordan. Yes. And Michael Jordan’s like, I’m in rooms right now considering selling my stake in the Charlotte Hornets for Yeah. Hundreds of millions of dollars right now, maybe even billions at this point. Yeah. So I think to your point, it likely is something that would mean a lot to people within hip hop, but not necessarily at this level where, you know, it’s not like both of these people were clearly at doing the same thing.

They were complimentary, but one was the artist. And the artist is always gonna have a bit of that poll there. So, yeah. And I guess we close things out, as we do with these case study breakdown episodes, we always break down who won the most from this record label in this era. Jay-Z’s the obvious answer, but if we were to take Jay-Z out of the equation, who do we think is the person that won most from Roc-A-Fella records?

[01:01:50] Zack Greenburg: Well, I mean, you know, I would almost argue that Dame was the big winner, over Jay, because Jay has gone on to do all these other things. And granted, like if he hadn’t gotten to start and Dame hadn’t been sort of like the early stage VC for him, You know, would he have, finally made it? I kind of think he eventually would’ve made it anyway.

and I think that, you know, the Roc-A-Fella years were the peak of Dame’s career. and, you know, he will always be, known in some circles and, you know, and revered in some circles for his role there. you know, in a way that every, you know, I’d say nothing he’s done since, has sort of done for him if that makes any sense.

[01:02:35] Dan Runcie: I get that. I followed that logic. My answer is Kanye and I think we talked about this a little bit, but I just. Because I think the core piece of the question is, where would this person have been without Roc-A-Fella records, right? I feel like Jay, or I feel like Dame probably would’ve found someone, probably even another artist in Harlem to attach his way to, I don’t think there was anything stopping him in the late nineties era for doing what he eventually did.

 He could have teamed up with Irv Gotti and done it with Murder Inc. I think he could have like, done it with a few of these other groups potentially. But would ye have been in the same situation if it weren’t for Roc-A-Fella? I think he clearly is talented, but I think he needed a little bit more of the stars aligning in the right way for him to have had the career path.


[01:03:21] Zack Greenburg: Yeah. And I think, you know, specifically what he was selling, you know, nobody was buying at the time, right? Like and it took someone with street cred. someone like Dame, someone like Jay to take a chance on him and elevate him and sort of into the national conversation that then, you know, allowed there to be sort of more demand for it, and, for people to really get invested in it.

So, yeah, I mean, I think kind of would’ve figured something out, but, you know, I really do wonder, I mean, he might’ve just gone a totally different group, you know, like he might’ve just been, like unknown in hiphop circles, but gone and done something totally different in, you know, in fashion circles and maybe become known, in hiphop circles, only in the way that somebody like Virgil Ablo became known. 

[01:04:02] Dan Runcie: Right. Or almost like a Jane d or someone like that. Mm-hmm. You have to be in it, and then you’re like, do you hear the brilliance of the music that this person produced? 

[01:04:09] Zack Greenburg: Yeah. Yeah. Yeah, yeah, yeah, yeah. That’s a really good point. So it could have been a very different path for him too. Yeah. Yeah. That’s good. It’s a good one. 

[01:04:16] Dan Runcie: Yeah. Well, I know we could talk for another hour about Roc-A-Fella itself 

[01:05:14] Zack Greenburg: All right. Very good. Thanks again, Dan. 

[01:05:16] Dan Runcie: You too, Zach. Thanks, man. 

[01:05:17] Dan Runcie Outro: If you enjoyed this podcast, go ahead and share it with a friend. Copy the link, text it to a friend. Post it in your group chat. Post it in your Slack groups. Wherever you and your people talk, spread the word. That’s how travel continues to grow and continues to reach the right people. While you’re at it, if you use Apple Podcast, Go ahead.

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Dan Runcie

Dan Runcie

Founder of Trapital

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