Earn Your Leisure

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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. 1 HR AGO

    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.

    1hr 3min

  2. 1 DAY AGO

    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

  3. 2 DAYS AGO

    Robert Herjavec on Mindset Shifts That Turn Entrepreneurs Into Millionaires

    Shark Tank legend Robert Herjavec reveals the critical MINDSET SHIFT that separates struggling entrepreneurs from massive success stories. Sharing his powerful journey as an immigrant and an eye-opening conversation with Mark Cuban, Robert explains why operating purely out of fear and survival mode will eventually stall your business. Find out why discovering your true PURPOSE is the ultimate key to scaling past your first million. 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.

    9 min

  4. 3 DAYS AGO

    How to Buy Stocks (For Beginners)

    Ready to start investing but don't know where to begin? We break down the EXACT step-by-step process to buy your first stock. From picking the right brokerage account (like Vanguard or Fidelity) to linking your bank and safely funding your account, this is the ULTIMATE beginner's guide. Stop leaving your money on the sidelines and learn how to actually execute a trade to start building wealth today! 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.

    7 min

  5. 4 DAYS AGO

    AI Agents Will Replace You Sooner Than You Think

    19 Keys breaks down the terrifying and exciting reality of AI agents. Discover how to build a "Second Brain" using tools like Obsidian to automate your entire business workflow. AI isn't necessarily replacing humans—it's replacing SYSTEMS. Learn how to feed your data into autonomous agents so they can act as your personal 24/7 workforce. Are you prepared for the robotic economy? 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.

    7 min

  6. 5 DAYS AGO

    What Happens to Apple After Tim Cook Steps Down?

    Tim Cook has officially stepped down as Apple's CEO, marking the end of a legendary era in tech. We break down his massive impact taking Apple to a multi-trillion dollar valuation, address the criticisms surrounding a lack of recent innovation, and discuss the ONE question on everyone's mind: who will lead Apple next? Watch to find out what this monumental shift means for the market and your investments! 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 See omnystudio.com/listener for privacy information.

    4 min

  7. 23 APR

    Jayda Cheaves on $50K Real Estate Loss, Building a 7-Figure Brand, Motherhood & Cutting Her Circle

    00:00 No Blueprint Needed01:10 Reunion And Catch Up02:34 Growth And Systems04:23 Real Estate Hard Lessons07:36 Renovation Wins And Costs15:55 Scaling With 3PL19:20 AI For Data Decisions27:28 Shopify Pro And Support28:14 Team Changes And Loyalty29:23 Clipping Your Circle31:15 Leveling Up Credibility32:07 Persona Versus Boardroom34:11 Selling Your Company35:24 Monetizing Without Ads38:25 Documenting Growth On YouTube40:11 CEO Lessons Ignore Noise42:02 Pop Ups And Retail Plans44:22 New Ventures Feminine Care45:56 Podcast Reality Check47:37 Investing And Money Habits50:06 Atlanta Origin Story52:20 Raising Kids With Wealth01:01:50 Wrap Up And Where To Follow In this episode, Jayda Cheaves joins Earn Your Leisure to break down the real journey behind building the Waydamin brand—from costly mistakes to major wins. She shares how losing over $50,000 in earnest money became a hard real estate lesson, while Rashad opens up about his own $400K loss. The conversation highlights the hidden costs of homeownership and why it’s still worth it despite the setbacks.   They also dive into business, branding, and AI. Jayda explains how she saved over six figures using AI, why her perspective on it changed, and how tools like Shopify have helped her scale. From staying authentic to building a respected personal brand, she gives real insight into what it takes to grow and sustain a successful business.   The episode wraps with gems on mindset, environment, and legacy—covering everything from the impact of your circle to teaching entrepreneurship early and creating multiple streams of income. This is a must-watch for anyone serious about leveling up.   #JaydaCheaves #EarnYourLeisure #Entrepreneurship #RealEstate #AI #BusinessTips #WealthBuilding #FinancialLiteracy #Investing #PersonalFinance #BrandBuilding 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.

    1hr 2min

  8. 22 APR

    Understanding Taxes: Tips and Strategies for Minimization

    Ms. Business break down the "Augusta Rule" for modern business owners. You are legally allowed to rent your primary home to your own company for 14 days completely tax-free. 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.

    9 min
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Hosts & Guests

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
    Clean
  • 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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