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Invest Fest | August 7-9, 2026
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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

Welcome to The Earn Your Leisure Podcast. Rashad Bilal and Troy Millings will be your host. Earn Your Leisure will be giving you behind the scenes financial views into the entertainment and sports industries as well as highlighting back stories of entrepreneurs. We will also be breaking down business models and examining the latest trends in finance. Earn Your Leisure is a college business class mixed with pop culture. We blend the two together for a unique and exciting look into the world of business. Let’s go!! #earnyourleisurepodcast

Earn Your Leisure

If I Could Only Buy 4 AI Stocks, These Would Be Them

https://api.omny.fm/orgs/e73c998e-6e60-432f-8610-ae210140c5b1/clips/397bc7f6-48de-4494-af16-b446013d3bae/transcript

How to Use Roommate & Rental Income to Qualify for a Mortgage

https://api.omny.fm/orgs/e73c998e-6e60-432f-8610-ae210140c5b1/clips/f74c3676-8d2d-4ae1-9823-b446013ca0af/transcript

Why Wealthy Investors Refuse to Sell Their Tech Stocks

https://api.omny.fm/orgs/e73c998e-6e60-432f-8610-ae210140c5b1/clips/4c6014f7-5cbc-44da-b72e-b4450129555c/transcript

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

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&rsquo;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. &nbsp; &nbsp; #EarnYourLeisure #JermaineDupri #Usher #Confessions #SoSoDef #MusicBusiness #HipHop #RNB #BowWow #KrisKrossof the most iconic labels ever &mdash; 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&rsquo;t replace true creatives.
The conversation also dives into major music debates, including whether Confessions is the greatest R&amp;B album of all time, if there&rsquo;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

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

https://api.omny.fm/orgs/e73c998e-6e60-432f-8610-ae210140c5b1/clips/458c0453-bc16-4e10-87cb-b44301096e99/transcript

If I Could Only Buy 4 AI Stocks, These Would Be Them

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