This is the breakdown on Roc-A-Fella Records. Founded in 1995 by the trio of Shawn “Jay Z” Carter (the talent), Damon “Dame” Dash (the promoter), and Kareem “Biggs” Burke (the silent partner), it became one of hip-hop’s most iconic labels.

The label took time to develop. Jay’s debut album, Reasonable Doubt, is now seen as a certified classic, but took time to get that recognition. It wasn’t until 1997 when Def Jam acquired a 50 percent stake in the label and The Roc went to that next level.

Roc-A-Fella then created Rocawear, Roc Films, and went on an unprecedented arena tour across the country — rare for rappers at the time. Other artists like Cam’Ron, Kanye West, Beanie Sigel, and Freeway joined the squad.. 

Despite the success, the founders grew apart, which led to its infamous split. To break it all down, I was joined by my friend and Jay Z biographer, Zack O’Malley Greenburg. Here’s what we covered:

1:20 Roc-A-Fella origin story

7:21 Reasonable Doubt

09:43 Friendly rivalry with Bad Boy Records

12:43 50-50 deal with Def Jam

15:59 How Roc-A-Fella’s deal compared to others

18:59 The Hard Knock Life Tour’s impact 

28:32 Expanding the brand beyond Jay Z 

30:32 Why Dame and Jay’s split was inevitable

38:59 Artists taking sides

44:21 Best Roc-a-Fella signing?

45:22 Best business move?

48:27 Dark Horse move?

53:02 Missed opportunity? 

59:07 Will Dame and Jay ever make up?

1:00:45 Who won the most from Roc-a-Fella? 

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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: 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 Trapital Podcast. I'm your host and the founder of Trapital, Dan Runcie. 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