In a dynamic episode of Earn Your Leisure, hosts Rashad Bilal and Troy Millings are joined by Math Hoffa, Ray Daniels, and Obi Omile for a layered conversation exploring the fusion of hip-hop culture, entrepreneurship, and innovation.
From the underground cyphers to boardroom strategy, the episode dives into the creative and business synergy that led to the launch of Off The Top, a new freestyle competition championed by Hoffa, Daniels, and Omile. The trio breaks down how mixtape culture laid the foundation for today’s lyrical showcases and why freestyle still matters in the digital era.
Omile takes the conversation deeper, reflecting on his journey building theCut, a barber booking app that’s reshaping how the Black community connects with one of its oldest institutions — the barbershop. His story sheds light on the cultural, social, and economic significance of grooming spaces, and why tech built by and for the community matters.
The episode also takes a sharp turn into the realities of business-building. From funding startups to navigating collaboration in creative industries, the trio gets candid about the discipline required to grow sustainably. They don’t sugarcoat the challenges either — especially when it comes to podcast monetization and turning passion projects into profit.
Ray Daniels adds a layer of music industry insight, offering his personal “Mount Rushmore” of Atlanta rap legends and weighing in on whether today’s scene is still producing global superstars. The conversation unpacks whether artists can still cut through in a saturated market — and what it really takes to stand out.
Packed with cultural commentary, entrepreneurial gems, and music industry real talk, this episode is a must-listen for creatives, tech builders, and hip-hop heads alike.
