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 EYLU Flash Sale (20 Spots, First Come): https://eyluniversity.com/ Jermaine Dupri joins Earn Your Leisure for a legendary conversation about music, business, and longevity in the entertainment industry. From discovering Kris Kross and Bow Wow, to helping create Usher’s Confessions, to building So So Def into one of 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