- 7 minutes 19 secondsMastering Relationship Capital: John Hope Bryant on How to Build Powerful Institutional Connections
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12 May 2026, 1:00 pm - 11 minutes 16 secondsIf I Could Only Buy 4 AI Stocks, These Would Be Them
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11 May 2026, 1:00 pm - 13 minutes 40 secondsHow to Use Roommate & Rental Income to Qualify for a Mortgage
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10 May 2026, 7:14 pm - 7 minutes 57 secondsWhy Wealthy Investors Refuse to Sell Their Tech Stocks
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9 May 2026, 6:03 pm - 1 hour 29 minutesJermaine Dupri On Being Part Of 400M Records Sold, Changing Hip Hop Forever & Never Getting Credit
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 ProjectsJermaine 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.
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7 May 2026, 4:16 pm - 8 minutes 7 secondsGary Vee on Why You *Must* Embrace AI (or Get Left Behind)
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6 May 2026, 1:00 pm - 8 minutes 9 secondsChakaBars EXPOSES South Africa’s Xenophobia Wave — Debunking the Diaspora Wars
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5 May 2026, 1:00 pm - 7 minutes 35 secondsForget Jobs — This Is How You Actually Get Rich in the AI Era
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4 May 2026, 1:00 pm - 8 minutes 29 secondsThis ONE Rule Separates Profitable Traders From the 90% Who Lose.
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3 May 2026, 1:00 pm - 10 minutes 21 secondsA Crash Could Be Coming But Not for the Reason You Think!
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2 May 2026, 5:19 pm - 1 hour 2 minutesAre Charter Schools Saving Kids… or Destroying Public Education? What Parents Need to Know 🎓
TIMESTAMPS:
00:00 Job Loss Wake Up
01:09 Welcome To The Show
02:36 From Buffalo To DC
04:55 Chocolate City Inspiration
07:09 Bet On Yourself
08:53 Engineering To Education
11:07 Launching A Charter School
11:32 Building Equity Now
12:44 Money And Marriage
14:19 Sponsor Break
15:07 Literacy Vs Wellness
17:47 Teaching Kids Investing
20:57 Training Teachers Too
24:58 Starting A School Process
26:14 Raising 30 Million
29:23 Deal Structure Lessons
29:52 Charter Enrollment Reality
31:12 Lottery Not Cherry Picking
32:44 Award And Financial Curriculum
33:54 Community Stewardship Model
35:15 Autonomy And Charter Debate
39:13 DEI Backlash Funding Fight
41:41 School Day Phones And AI
46:24 Charter Vs Private School
50:56 Scaling Plans And Early Learning
55:49 Invest Fest And Workshop
59:35 Legacy Family And ClosingIn this episode of Earn Your Leisure, we sit down with Shomari James to break down his journey from leaving his hometown to building a $30 million charter school and redefining what education can look like. From witnessing Black excellence in DC to making bold moves without fear, Shomari shares the mindset, strategy, and vision it takes to create real impact. He also opens up about building a nonprofit for protection, empowering his family financially, and why telling your spouse they can quit their job is one of the ultimate goals of success.
We dive deep into the education system—charter schools vs public schools, whether charter schools are helping or hurting education, and what truly makes a school successful. Shomari explains how his school was built with 40% Black male educators, why financial literacy must start early, and how initiatives like custodial accounts and scholarships can change the trajectory of children’s lives. From teaching 5-year-olds about money to discussing uniforms, technology in classrooms, and the impact of losing DEI funding, this conversation is packed with game-changing insights for parents, educators, and entrepreneurs alike.
#EarnYourLeisure #EYL #CharterSchools #FinancialLiteracy #EducationReform #BlackExcellence #Entrepreneurship #WealthBuilding #Investing #Nonprofit #PublicSchools #PrivateSchools #FinancialEducation #DEI #Business #Mindset #SuccessSubscribe
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