meta_pixel
Tapesearch Logo
Log in
Earn Your Leisure

Jermaine Dupri On Being Part Of 400M Records Sold, Changing Hip Hop Forever & Never Getting Credit

Earn Your Leisure

iHeartPodcasts

Entrepreneurship, Education, Careers, News, Investing, Business, Business News

4.97.9K Ratings

🗓️ 7 May 2026

⏱️ 90 minutes

🧾️ Download transcript

Summary

TIMESTAMPS:

00:00 Kris Kross Discovery
01:10 Welcome Jermaine Dupri
02:53 Longevity Staying Relevant
06:08 Publishing Money Explained
11:14 Pressure After Hits
14:58 Finding Kris Kross
16:33 Backwards Clothes Moment
21:14 Atlanta Stigma and Press
25:56 Masters Deals and Mentors
29:20 Usher Without Signing
30:25 Building Usher My Way
30:52 Label Loyalty vs Crew Culture
32:45 Signing Jagged Edge
33:31 Becoming the Artist
34:09 Kris Kross Writing Bootcamp
36:34 Throwaways to Life 1472
37:37 Why So So Def Overlooked
39:54 Youth Movement Legacy
46:34 Making It With Jay Z
49:19 Discovering Bow Wow
55:56 Bow Wow Sparks 106 Park
58:11 Writing for Bow Wow’s Identity
59:51 Best Songwriter Year Debate
01:01:16 Confessions Hit Streak
01:01:36 My Boo Left Off
01:01:55 Writing Confessions Story
01:04:28 Concept Album Misread
01:06:54 Singles And Video Choices
01:08:20 Selling Music Catalogs
01:10:56 Rights Reversion Explained
01:12:36 Why Catalogs Cost More
01:16:59 New Publishing From Samples
01:18:51 Why Verzuz Fell Through
01:20:44 Verzuz Strategy And Freestyles
01:26:15 AI In Music Production
01:29:10 Wrap Up And New Projects

Jermaine Dupri joins Earn Your Leisure for a legendary conversation about music, business, and longevity in the entertainment industry.     #EarnYourLeisure #JermaineDupri #Usher #Confessions #SoSoDef #MusicBusiness #HipHop #RNB #BowWow #KrisKrossof the most iconic labels ever — JD breaks down the blueprint behind his decades of success. He also explains why songwriting became his superpower and how learning every side of the music business helped him stay ahead for over 30 years.

In this episode, Jermaine Dupri shares untold stories about getting a $1 million publishing advance, selling millions of records while still being discredited because of his age, and why he treats music catalogs like real estate. He also breaks down how producers actually get paid, the real reason the Bad Boy vs So So Def Verzuz never happened, and why AI still can’t replace true creatives.

The conversation also dives into major music debates, including whether Confessions is the greatest R&B album of all time, if there’s really such a thing as a bad deal, and why So So Def deserves to be considered a top 5 label ever. This episode is packed with timeless game for artists, entrepreneurs, and creatives alike.


Subscribe and watch more videos here: https://www.youtube.com/@EarnYourLeisure

Join the EYL community for deeper training and a more detailed approach:
https://www.eyluniversity.com

Join the number one stock club in the world:
https://www.ianinvest.com

Invest Fest | August 7-9, 2026
Grab early bird tickets now: https://www.investfest.com

#EarnYourLeisure #JermaineDupri #Usher #Confessions #SoSoDef #MusicBusiness #HipHop #RNB #BowWow #KrisKross #Podcast

See omnystudio.com/listener for privacy information.

Transcript

Click on a timestamp to play from that location

0:00.0

This is an IHeart podcast.

0:02.6

Guaranteed Human.

0:38.3

I brought youth to hip-pop. When Crish Cross came out, the entire rap game was 20 plus years old. These leagues is 11 and 12. Nobody told me about them. I found them at the mall. They weren't even rappers. If I get a song that go along with the way they look, these kids is out of here. I knew that. Do you feel pressure to continue or you didn't know that you just have this natural gift to create songwrite and mold artists? Babyface told me that that's cool, that little jump record you got, but how many times can you do that? That stuck with me forever. So all I've been trying to do is just continue to keep making Babyface. See, I could do it again. What's the craziest publishing check you ever got? Once you start selling records like that, everybody know the money is there. So you're getting that, you're getting that all the money. The talent that I had, nobody else had. I don't think people recognize the marketing genius that you are. Would you ever sell your catalog? If you buy it catalog for $500 million and you go broke, you can sell it for $500 million.

0:57.3

And it's not going to depreciate, it's just going to keep going up. There's no doubt in your mind that this is a win. You get in a fight with Ingers. You got to know who you fighting with. AI can't do what you just did. could sit there and prompt it, but it's like, ultimately, you're just telling AI to find something that somebody already did. All right, guys, welcome back. Special episode, Earnie Alicia. Yeah, yeah. Atlanta. This is our Atlanta home, so it's only right we had to tap in one of the greatest, most influential people that ever come out of the city of Atlanta. The one and only, Jerm Dupree. What's up, my brother? What's that? What I'm the word. What's the be? The greatest producer of the 21st century. That's what they say. No, that, that you are the greatest producer of the 21st century. Like, well, let's not, let's not sugarcoat this. Right. We go.

1:45.1

Nah, you know, it's great.

1:47.3

It's the first time we actually had like a sit-down conversation.

1:48.9

But we've been around each other.

1:52.3

You've done InvestFest for us before came to InvestFest.

1:55.9

So this is a conversation definitely looking forward to having as far as to, you know,

2:03.0

just hear your perspective on the music business from the artist side, from the producer side, from the label side, from the CEO side, I think you have a unique perspective.

2:06.7

You're like Bill Russell, play a coach.

2:11.1

You know, like you actually wore like both sides of the things.

2:14.0

There's not a lot of people I think that have that perspective from you're an artist, but you're a producer, but you're an executive and you're a CEO. So it's like you, you know, you played in every, every position. And I'm thinking about it now, like, how many people have we seen had a consistent run for 40 years?

2:32.3

That long, but yeah, close. Is this? I mean nights. 30, 30, 30, 30, 30. Somewhere in there. I mean, we're going to get the 40, though. I mean, we're here now. I'm thinking criss-cross early is like 90, 90, 92. Yeah. Yeah, we're getting in. Yeah. Yeah, we getting in. Yeah. So yeah, looking forward to it yeah we getting there yeah so yeah looking

2:52.6

forward to it man but uh yeah thank you for joining us once again appreciate so let's let's get

2:57.3

into it as far as longevity he started with that longevity right like what do you think

3:04.1

has separated you from other people in the space as far as being able to stay relevant for different decades and changing from working with Def Jam to being an artist, being a producer, working with Usher.

3:16.3

You know, like, how have you been able to maintain relevancy for so long?

3:20.3

I mean, I think one is because I was super young, you know, when I came here, I don't think people really realized how young I was.

3:27.8

So the first 10 years of people paying attention to me, almost five of them years, I wasn't illegal.

3:37.3

You know what I mean?

3:37.8

Like, hopefully, you know what I'm saying?

...

Please login to see the full transcript.

Disclaimer: The podcast and artwork embedded on this page are from iHeartPodcasts, and are the property of its owner and not affiliated with or endorsed by Tapesearch.

Generated transcripts are the property of iHeartPodcasts and are distributed freely under the Fair Use doctrine. Transcripts generated by Tapesearch are not guaranteed to be accurate.

Copyright © Tapesearch 2026.