Earn Your Leisure Podcast Summary Episode Title: How 85 South Built a Comedy Empire with No Script & No Filter
Release Date: July 24, 2025
Hosts: Rashad Bilal and Troy Millings
Guests: Karlous Miller & Chico Bean

1. Introduction to 85 South’s Journey

In this engaging episode, Rashad Bilal and Troy Millings delve deep into the entrepreneurial journey of 85 South, a formidable name in the comedy industry. Joined by guest Chico Bean, the hosts explore how 85 South cultivated a comedy empire without relying on traditional scripts or filters, blending authentic humor with savvy business acumen.

2. From Strippers to Real Estate: Chico Bean’s Transformation

Chico Bean shares his personal story of transitioning from the entertainment industry to real estate, highlighting the adaptability and entrepreneurial spirit prevalent within the 85 South community.

Chico Bean [04:43]: "A lot of the strippers who were around when I was around, I see them in the city now, and they’re doing great things. They’re selling houses, real estate."

3. Overcoming Personal Struggles Through Travel

Chico opens up about his emotional journey, particularly his trips to Ghana to cope with personal loss, emphasizing the therapeutic role of travel and self-discovery.

Chico Bean [08:52]: "One of the best times, most peace I ever had, man. And I went back the next year, and the first year I went was when Chance the Rapper did that concert out there."

4. Building an Independent Media Platform

Rashad discusses 85 South’s strategic shift from platforms like YouTube to their own independent media channel, Channel 85. This move was driven by a desire for greater control over their content and revenue streams.

DC Young Fly [27:44]: "Once institutional money comes in, like you said, it's tough to stop."

5. The Dynamics of Touring and Audience Engagement

The hosts and Chico delve into the complexities of organizing tours, from negotiating with venues to managing a growing team. They highlight the importance of genuine fan interactions and the unique bond they share with their audience.

DC Young Fly [39:57]: "It's a lot... being responsible for 35, 40 grown people having too much fun. That's the hard part."

6. Navigating Legal Challenges and Business Relationships

DC Young Fly recounts a legal tussle with a business partner, shedding light on the challenges of maintaining professional relationships and the importance of clear communication in business.

DC Young Fly [25:07]: "He sent the paperwork and made it look like they were still together. So when I signed to do the shows with his partner, I was like, nobody told me."

7. Impact on Fans and Community Empowerment

The conversation shifts to the profound impact 85 South has on their listeners, with fans sharing how the podcast has influenced their financial literacy and personal growth.

Chico Bean [64:31]: "I just watched it every day, and it just took my mind off of whatever it was that was going on."

8. Addressing Financial Responsibility and Support

Chico and DC discuss the ethical dilemmas of responding to fans seeking financial help, emphasizing responsible advice and the importance of financial independence.

Chico Bean [71:16]: "I choose me. I choose me."

9. Fostering Positive Relationships in the Comedy Industry

The hosts explore the often-contentious relationships between comedians, advocating for mutual support and collaboration over rivalry.

DC Young Fly [87:15]: "A lot of these niggas are just... they got some disagreements that they can't work out."

10. Future Endeavors and Expanding Influence

Chico and DC touch upon their collaborations with industry giants like Kevin Hart and discuss future projects, including innovative content platforms and expanding their comedic reach.

Chico Bean [93:58]: "Shout out to Kevin Hart, man. He produced the stand-up special that I got on Hulu."

11. Conclusion: The Essence of 85 South’s Success

Rashad wraps up the episode by commending 85 South for their relentless drive, authentic connections, and innovative approach to comedy and business, highlighting them as exemplary entrepreneurs in the entertainment industry.

Notable Quotes

• Chico Bean [04:43]: "A lot of the strippers who were around when I was around, I see them in the city now, and they’re doing great things. They’re selling houses, real estate."
• Chico Bean [08:52]: "One of the best times, most peace I ever had, man. And I went back the next year, and the first year I went was when Chance the Rapper did that concert out there."
• DC Young Fly [25:07]: "He sent the paperwork and made it look like they were still together. So when I signed to do the shows with his partner, I was like, nobody told me."
• Chico Bean [64:31]: "I just watched it every day, and it just took my mind off of whatever it was that was going on."
• Chico Bean [71:16]: "I choose me. I choose me."
• DC Young Fly [87:15]: "A lot of these niggas are just... they got some disagreements that they can't work out."
• Chico Bean [93:58]: "Shout out to Kevin Hart, man. He produced the stand-up special that I got on Hulu."

Key Takeaways

• Entrepreneurial Spirit: 85 South exemplifies how passion combined with strategic business moves can build a successful independent media empire.

• Authenticity: Their unfiltered and unscripted approach resonates deeply with audiences, fostering genuine connections.

• Community Impact: Beyond entertainment, 85 South plays a pivotal role in educating and empowering their community on financial literacy and personal growth.

• Resilience: Navigating legal challenges and industry dynamics showcases their ability to adapt and overcome obstacles.

• Future Growth: Collaborations with industry leaders and innovations in content delivery position 85 South for sustained success and influence.

For those interested in entrepreneurship, comedy, and the intersection of entertainment with financial literacy, this episode of Earn Your Leisure provides invaluable insights into building and sustaining a media empire with authenticity and purpose.