Earn Your Leisure Podcast: Episode Summary

Title: “They Don’t Want Us to Have the Info!” Math Hoffa, Ray Daniels & Obi Omile Expose the Game
Hosts: Rashad Bilal, Troy Millings (EYL Network)
Release Date: May 22, 2025

1. Introduction of Guests

In this episode, hosts Rashad Bilal and Troy Millings welcome three influential guests: Math Hoffa, Ray Daniels, and Obi Omile. Each brings a unique perspective from the intersections of hip-hop, entrepreneurship, and content creation.

Notable Quote:
[01:39] Obi Wan: “This is going to be a fun episode.”

2. Profiles and Backgrounds

• Ray Daniels
  Originating from New York, Ray is described as a "cultural referee" with extensive experience in the music industry. He transitioned from a music executive to a content producer during the pandemic, gaining recognition as a content creator.

  Notable Quote:
  [02:11] Mav Hoffa: “Ray was actually in the music business for a long time executive and then during the pandemic actually started to produce content.”

• Obi Omile
  Obi is the co-founder of The Cut, a leading barber scheduling app with approximately 8 million users nationwide. The app streamlines the process of finding and booking barbers, enhancing convenience for users across various cities.

  Notable Quote:
  [03:38] Obi Wan: “The number one app to find a barber anywhere around the country. We have about 8 million users.”

• Math Hoffa
  Recognized as a pioneer in battle rap culture, Math Hoffa bridges the worlds of hip-hop and podcasting. His contributions have significantly shaped the landscape of freestyle battles and content creation.

  Notable Quote:
  [04:27] Ray Daniels: “Math was policing. I was like, we just having fun with rap. Nah, nah, it's not fun.”

3. The Cut: Building a Barber Scheduling Empire

Obi Omile delves into the inception and growth of The Cut. The app was conceived in 2015, inspired by the rise of service-based platforms like Uber and Lyft. Initially a prototype, it quickly garnered interest from barbers and users alike, leading to a successful launch.

Key Points:

• Funding and Growth:
  The Cut utilized equity crowdfunding, allowing barbers themselves to invest, fostering strong brand loyalty. Following participation in Techstars, the app secured its first round of venture capital in 2021 and achieved profitability in early 2025.

  Notable Quote:
  [18:47] Obi Wan: “That was like a big part of our story. And then after that, we did an accelerator. We did Techstars. And then that led to us finally raising our first bit of venture capital.”

• Business Model:
  The app operates on a subscription model for barbers ($25/month) and charges users a processing fee per booking, aiming to create a comprehensive ecosystem for barbers and clients.

  Notable Quote:
  [16:49] Obi Wan: “So it's all things like if you schedule an appointment... we're trying to complete, like, build a whole ecosystem for barbers and barbershops.”

4. Freestyle Rap Competition in Barbershops

The collaboration between the hosts and guests led to the organization of a three-city freestyle rap competition held in barbershops across New York, the DMV (DC, Maryland, Virginia), and Atlanta. This initiative not only promotes rap talent but also enhances brand awareness for The Cut.

Key Points:

• Format and Judging:
  Contestants are required to incorporate references to The Cut or the hosts in their freestyles. The judges evaluate based on creativity, preparation, and the ability to engage the audience.

  Notable Quote:
  [07:28] Sluggo: “It's another language to me. It's complicated.”

• Participation and Impact:
  Approximately 400-500 participants signed up, with notable winners emerging from each city, including female rappers, highlighting diversity and talent within the competition.

  Notable Quote:
  [08:07] Obi Wan: “Yes, sir. Currently, right now, our championship contestants are actively promoting it.”

5. Challenges in Podcasting and Content Creation

The hosts discuss various challenges faced in running a successful podcast, including co-host conflicts, monetization issues, and the complexities of navigating platforms like YouTube.

Key Points:

• Co-Host Dynamics:
  Disagreements and personality clashes among co-hosts led to departures, affecting the show's consistency and growth.

  Notable Quote:
  [23:02] Cash Flow: “I'm a man of my word, and if you give me your word, I expect that you're gonna stand on it.”

• Monetization and Platform Policies:
  Changes in YouTube's algorithm and monetization policies posed significant hurdles, leading to demonetization of popular episodes and financial instability.

  Notable Quote:
  [28:26] Cash Flow: “I didn't like that type of, like, it doesn't work.”

6. Business Lessons and Industry Insights

The conversation shifts to broader business lessons, emphasizing the importance of an abundance mindset over a scarcity mentality. The guests advocate for transparency and information sharing within the industry to empower creators and entrepreneurs.

Key Points:

• Abundance vs. Scarcity Mindset:
  Adopting an abundance mindset fosters collaboration and mutual growth, whereas a scarcity mentality leads to competition and isolation.

  Notable Quote:
  [51:17] Mav Hoffa: “Scarcity mindset looks at like when I climb up the ladder, I'm kicking the ladder down... It's a limited mindset.”

• Negotiating Deals and Transparency:
  A significant barrier in the entertainment and startup industries is the lack of transparency in deal negotiations. The guests stress the necessity for creators to educate themselves to secure fair deals.

  Notable Quote:
  [38:38] Cash Flow: “Absolutely, definitely.”

7. Hip-Hop Culture and Community

A substantial portion of the episode is dedicated to discussing hip-hop culture, the evolution of freestyle rap, and the regional dynamics between New York and Atlanta rap scenes.

Key Points:

• Freestyle vs. Prepared Rap:
  The hosts debate the authenticity of freestyles, distinguishing between true improvisational rap and rehearsed verses presented as freestyles.

  Notable Quote:
  [11:29] Obi Wan: “You could tell, were freestyling off the top, they definitely got bonus points.”

• Regional Rap Scenes:
  The dialogue highlights the distinct characteristics of New York and Atlanta rap scenes, debating influential artists and their impacts on the culture.

  Notable Quote:
  [75:17] Luong Sluggo: “That's why TI is the most important artist.”

8. Conclusion and Future Directions

The episode concludes with the hosts and guests discussing future initiatives, emphasizing the need for continued collaboration, transparent information sharing, and expanding platforms like The Cut to empower more creators and entrepreneurs.

Key Points:

• Future Projects:
  Plans to extend The Cut internationally and enhance the freestyle competition format to include more cities and diverse participants.

  Notable Quote:
  [08:34] Obi Wan: “There’s so many opportunities to really give rappers an opportunity to showcase their skill.”

• Call to Action:
  The guests encourage listeners to engage with their platforms, participate in competitions, and support black-owned businesses.

  Notable Quote:
  [80:54] Obi Wan: “You can go find all the content at The Cut app on IG TikTok all platforms.”

Final Thoughts:
This episode of Earn Your Leisure provides an insightful exploration into the convergence of hip-hop culture, entrepreneurship, and content creation. The candid discussions offer valuable lessons on business strategy, the importance of mindset, and the cultural significance of communal spaces like barbershops in fostering creativity and community.

Connect with the Guests:

• Obi Omile (Obi Wan): Follow on Instagram and TikTok as @Mr_Underscore ObiWan_WaN
• Ray Daniels: Available across all major social media platforms
• Math Hoffa: Follow on relevant social channels

For more content, visit The Cut app and stay tuned for upcoming freestyle competition highlights.