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Earn Your Leisure

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Earn Your Leisure
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  • Earn Your Leisure

    KevOnStage Gets Honest About Money, Marriage & Losing His Brother

    2026/09/09 | 1h 3 mins.
    KevOnStage wanted to compete with Netflix. Then he had to shut down his own streaming platform. He joins Earn Your Leisure to explain what went wrong, what he learned, and how that experience helped open the door to his Tubi partnership.
    Rashad Bilal and Troy Millings sit down with KevOnStage for an honest conversation about the business behind the comedy. From posting three to four videos a day to building an audience that actually buys tickets, Kev breaks down how he turns attention into income and why owning his content matters.
    In this episode, we discuss:
    • Why his $5.99 streaming subscription was harder to sustain than he expected
    • How Safe Space and his audience helped him build his relationship with Tubi
    • The difference between having followers and having paying fans
    • How content ownership and licensing create opportunities to earn beyond the first release
    • How his wife helped him change the marketing for Successful Failure
    • His thoughts on Druski’s church comedy and the backlash
    • Why protecting his marriage helps him protect his focus and energy
    Kev also opens up about losing his brother and creating Grief Sucks, sharing how he uses comedy to honor his brother and connect with people navigating loss.
    What’s a business setback that taught you something success couldn’t? Share your experience in the comments.
    Chapters:
    00:00 Mystique vs Money
    00:07 Content Speed Strategy
    00:31 Equity and Ownership
    00:48 Monogamy and Focus
    01:25 Earn Your Leisure Intro
    01:48 New York Bodega Talk
    02:21 Awards and Invest Fest
    03:19 Relatable Comedy Style
    04:05 Arbys Cheesesteak Review
    05:06 Daily Content Workflow
    12:36 How Much to Share
    14:54 Building a Creator Ecosystem
    16:53 From Plays to Internet Fame
    18:45 Funnel and Singles Approach
    20:46 Why Mystique Doesnt Work
    25:00 Book Launch Pivot
    28:23 Authenticity as Currency
    29:51 Tubi Partnership Tease
    29:56 Netflix Dreams Reality Check
    30:43 Pricing Cuts and Platform Fees
    31:36 Why the Platform Wasn’t Scalable
    32:10 Content Crunch and Free Trial Abuse
    33:51 Churchy Opens Doors at Tubi
    35:11 Building the Tubi Creator Partnership
    37:02 Drewski and Church Comedy Backlash
    40:03 Ownership IP and Long Term Wealth
    45:07 Grief Sucks Origin Story
    50:22 Tour Life and Healing Through Laughs
    53:24 Cracker Barrel Modernization Roast
    56:08 Monogamy as a Success Strategy
    01:02:01 Tour Dates and Final Sendoff
    Subscribe to Earn Your Leisure for more conversations about business, money, ownership, and building on your own terms.
    #EarnYourLeisure #KevOnStage #Entrepreneurship
    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.
  • Earn Your Leisure

    Buying the Dip Is a TRAP — The Truth About Surviving the Next Crash

    2026/09/09 | 8 mins.
    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.
  • Earn Your Leisure

    Inside the $300 Billion Wine Industry_ How Donae Burston Launched a Black-Owned Wine Company-MP3

    2026/09/08 | 55 mins.
    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.
  • Earn Your Leisure

    Magic Johnson Reveals Billion-Dollar Secrets & Lessons from Failure

    2026/09/07 | 10 mins.
    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.
  • Earn Your Leisure

    The #1 Portfolio Mistake Keeping You Broke (And How to Fix It)

    2026/09/06 | 12 mins.
    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.
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About Earn Your Leisure
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
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