Earn Your Leisure

iHeartPodcasts
  • 4.9 (206)
  • INVESTING
  • UPDATED WEEKLY

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

  1. 21 HRS AGO

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

    TIMESTAMPS: 00:00 Kris Kross Discovery01:10 Welcome Jermaine Dupri02:53 Longevity Staying Relevant06:08 Publishing Money Explained11:14 Pressure After Hits14:58 Finding Kris Kross16:33 Backwards Clothes Moment21:14 Atlanta Stigma and Press25:56 Masters Deals and Mentors29:20 Usher Without Signing30:25 Building Usher My Way30:52 Label Loyalty vs Crew Culture32:45 Signing Jagged Edge33:31 Becoming the Artist34:09 Kris Kross Writing Bootcamp36:34 Throwaways to Life 147237:37 Why So So Def Overlooked39:54 Youth Movement Legacy46:34 Making It With Jay Z49:19 Discovering Bow Wow55:56 Bow Wow Sparks 106 Park58:11 Writing for Bow Wow’s Identity59:51 Best Songwriter Year Debate01:01:16 Confessions Hit Streak01:01:36 My Boo Left Off01:01:55 Writing Confessions Story01:04:28 Concept Album Misread01:06:54 Singles And Video Choices01:08:20 Selling Music Catalogs01:10:56 Rights Reversion Explained01:12:36 Why Catalogs Cost More01:16:59 New Publishing From Samples01:18:51 Why Verzuz Fell Through01:20:44 Verzuz Strategy And Freestyles01:26:15 AI In Music Production01:29:10 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, 2026Grab 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.

    1h 30m

  2. 2D AGO

    Gary Vee on Why You *Must* Embrace AI (or Get Left Behind)

    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, 2026Grab early bird tickets now: https://www.investfest.com See omnystudio.com/listener for privacy information.

    8 min

  3. 3D AGO

    ChakaBars EXPOSES South Africa’s Xenophobia Wave — Debunking the Diaspora Wars

    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, 2026Grab early bird tickets now: https://www.investfest.com See omnystudio.com/listener for privacy information.

    8 min

  4. 4D AGO

    Forget Jobs — This Is How You Actually Get Rich in the AI Era

    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, 2026Grab early bird tickets now: https://www.investfest.com See omnystudio.com/listener for privacy information.

    8 min

  5. 5D AGO

    This ONE Rule Separates Profitable Traders From the 90% Who Lose.

    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, 2026Grab early bird tickets now: https://www.investfest.com See omnystudio.com/listener for privacy information.

    8 min

  6. 5D AGO

    A Crash Could Be Coming But Not for the Reason You Think!

    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, 2026Grab early bird tickets now: https://www.investfest.com See omnystudio.com/listener for privacy information.

    10 min

  7. APR 30

    Are Charter Schools Saving Kids… or Destroying Public Education? What Parents Need to Know 🎓

    TIMESTAMPS: 00:00 Job Loss Wake Up01:09 Welcome To The Show02:36 From Buffalo To DC04:55 Chocolate City Inspiration07:09 Bet On Yourself08:53 Engineering To Education11:07 Launching A Charter School11:32 Building Equity Now12:44 Money And Marriage14:19 Sponsor Break15:07 Literacy Vs Wellness17:47 Teaching Kids Investing20:57 Training Teachers Too24:58 Starting A School Process26:14 Raising 30 Million29:23 Deal Structure Lessons29:52 Charter Enrollment Reality31:12 Lottery Not Cherry Picking32:44 Award And Financial Curriculum33:54 Community Stewardship Model35:15 Autonomy And Charter Debate39:13 DEI Backlash Funding Fight41:41 School Day Phones And AI46:24 Charter Vs Private School50:56 Scaling Plans And Early Learning55:49 Invest Fest And Workshop59:35 Legacy Family And Closing     In 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  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, 2026Grab early bird tickets now: https://www.investfest.com See omnystudio.com/listener for privacy information.

    1h 3m

  8. APR 29

    The Winning Traits Every Successful Founder Has 💼

    What REALLY makes a startup founder successful? We reveal the specific, borderline-crazy characteristics that venture capitalists look for before handing over millions of dollars. Learn why "founder market fit" is crucial, how to maintain a 5-year vision through the ups and downs, and discover the UNSEXY, traditional industries (like accounting and regional banking) that are ripe for massive technological disruption right now. 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 See omnystudio.com/listener for privacy information.

    5 min
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Hosts & Guests

4.9
out of 5
206 Ratings

About

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

Information

  • Creator
    iHeartPodcasts
  • Years Active
    2019 - 2026
  • Episodes
    1.5K
  • Rating
    Explicit
  • Copyright
    2026 iHeartMedia, Inc. © Any use of this intellectual property for text and data mining or computational analysis including as training material for artificial intelligence systems is strictly prohibited without express written consent from iHeartMedia
  • Show Website
    Earn Your Leisure

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