When it comes to hip-hop history, Talib Kweli and Jasmin Leigh have been holding it down in a major way with their People’s Party podcast. In the latest episode, the pair recently connected with DJ Clark Kent (who produced three tracks on Jay-Z’s Reasonable Doubt), who shared a few key insights about his early days working with Biggs, Dame Dash, and a still-hustling Jay-Z.

DJ Clark Kent

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When asked about the process of convincing a young Jay-Z to give up hustling in favor of pursuing a rap career, Clark Kent has a chuckle. “Everybody who was a part of Roc-a-Fella in the very-very-very beginning overlapped,” he reflects, alluding to the two worlds of hip-hop and hustling. “Biggs overlapped, Dame overlapped. Jay overlapped. It’s just I’m out there going No. Make this rap shit. You have to understand, I had a job at a rap company very young. I was like no. We gotta do this instead.”

“I got there, and two days later I’m trying to find [Jaz-O] and Jay-Z,” he continues. “Like no, we gotta do this. Because they’re the first rappers I thought should have a record deal. I went looking for them, and it took a while to find them, but it was we need to be doing this. I just didn’t want to die, I didn’t want to go to jail. I wanted things to be going better. And I didn’t want them to go to jail.”

DJ Clark Kent Jay-Z

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“They had actual true talent,” praises Clark. “I been around some people who rap, and I’m like yeah, I’m cool. I been around some people who sing, I’m like yeah, I’m cool. When I heard Jay and Jaz the first time, when we was all teenagers, I was like — that’s some other shit.” When Jasmin Leigh inquires about when the decision was made to stop hustling, Kent draws up a frame of reference. “I think right about the time Reasonable Doubt dropped. It was like oh shit, it’s working. The thing was, [Jay] was going to retire. I was the only one who knew he wasn’t retiring. He’s way too talented and it’s not going to be enough.”

“He was doing way too well before rap,” he continues. “This rap thing was going to do fine, but it’s not going to do as well in the beginning. But it’s just way too easy for him. They all believed that it would just be one album, and we’d laugh at everyone. I’m the only one telling people around me ‘it’s not going to be one album.'”

For more from DJ Clark Kent, including a bit of history about the creation of Jay and Big’s “Brooklyn’s Finest,” be sure to catch the full episode of Talib Kweli‘s People’s Party below.