Breaking the Code: Ray Daniels, Obi Omile, and Math Hoffa on the Future of Music, Media, and Black Ownership

In a conversation rich with insights on music, culture, entrepreneurship, and the shifting dynamics of content creation, Troy and Rashad from Earn Your Leisure linked up with Ray Daniels, battle rap icon Math Hoffa, and tech entrepreneur Obi Omile. This wasn’t just a conversation—it was a cultural summit built around a grassroots initiative: a freestyle rap competition powered by The Cut, a barber scheduling app co-founded by Omile that has reshaped how people connect with barbers across the country.

The competition, which crisscrossed New York, Atlanta, and the DMV, took place inside local barbershops, bringing lyricism back to its communal roots. But this was more than a battle—it was a showcase of strategy, technology, and passion. Artists competed for a $10,000 prize, with the added incentive of national exposure and the co-sign of three judges whose voices carry weight across music and media.

Barbershop Roots and Cultural Resonance

The concept of using barbershops as the central stage was rooted in legacy. For generations, Black barbershops have been more than just grooming spaces—they’ve been cultural forums, places where music is debated, mixtapes get played, and artists get crowned by word of mouth. It’s a space of authenticity and community, and that’s precisely why the tour worked.

Obi Omile’s journey began with something relatable: struggling to find a barber after relocating. That pain point became the basis for The Cut, which now has over 8 million users and is on track to hit 100 million appointments booked. The competition added a new layer to the app's impact. It wasn’t just about convenience—it was about cultural relevance.

"The shop is where you hear who’s next. You walk in, someone’s bumping something new, and that’s how the streets start talking," said Math Hoffa, who’s long recognized the synergy between barbershops and hip-hop. His own podcast, My Expert Opinion, famously launched from a barbershop setting, echoing those grassroots vibes.

Each emcee in the competition was required to creatively work in a reference to The Cut. While some came with sharp, written verses, others leaned on improvisation. The judging panel brought a spectrum of expectations: Daniels sought out narrative and emotional impact, Hoffa zeroed in on technical skill and presence, and Omile wanted cleverness, especially in how rappers connected the product with their bars.

Women Leading the Way

Of the three city champions crowned, two were women—an achievement that didn’t go unnoticed. Their victories weren’t tokens; they were earned. It also spoke to the growing presence of women in a space that too often leans hyper-masculine. These lyricists not only impressed the judges, but left audiences in awe, reinforcing that hip-hop is anybody’s game when the mic is live.

The entire competition was independently funded—a move that gave the creators full creative and strategic control. While that also meant more responsibility, it paid off in credibility. Talks with sponsors are already happening, and the next leg of the tour may expand into Texas, the Midwest, and the West Coast.

Building a Platform: The Origin of The Cut

Omile recounted the early days of The Cut—an idea born out of necessity, executed through hustle. After struggling to find a barber in a new city, he realized the gap in the market. By leaning on his network and tapping into angel investor circles from his alma mater, James Madison University, Omile bootstrapped the early version of the app.

Then came a game-changing move: equity crowdfunding. By inviting barbers to invest in the very app they’d use, Omile built loyalty from the ground up. Hundreds of barbers became shareholders, evangelists, and advisors. That grassroots trust transformed The Cut from a convenience tool into a cultural staple.

Now profitable and scaling, the platform continues to grow, and Omile has his sights set on global expansion. “The vision is to be the default interface between clients and barbers around the world,” he said.

Lessons from the Podfather: Math Hoffa’s Content Journey

Hoffa’s journey into content wasn’t traditional. A battle rap legend known for his on-stage intensity, he pivoted into podcasting as a way to preserve legacy and spark conversations that matter. During the pandemic, he went live nightly, slowly building a loyal following. Once the world reopened, those virtual roots gave rise to My Expert Opinion, a show that became a viral phenomenon.

But growth came with growing pains. Co-host departures, disagreements over money, and creative differences created public turbulence. Hoffa explained the core issue: a lack of understanding about the business side of content. He managed bookings, production, and finances, while others focused on performance. That imbalance, without legal structure or communication, caused fractures.

“It’s not just about having a viral moment,” he said. “It’s about sustainability. And that takes discipline, contracts, and mutual respect.”

Ray Daniels on Industry Gatekeeping and Empowerment

Ray Daniels brought his experience as a music executive to the table. Still active in shaping global hits, Daniels is also one of the few voices in the industry pulling back the curtain on how deals are really made. He spoke candidly about buy-sell clauses, legal fees, and the importance of transparency.

One story stood out: Daniels convinced a fellow Black lawyer to demand the full 5% legal fee in a contract negotiation—standard for white attorneys, but often denied to Black ones. That small act of advocacy unlocked deeper trust and helped close a major deal. “That’s what changes the game—information. And the willingness to share it,” he said.

Daniels emphasized that Black executives and artists need to stop treating success like a zero-sum game. The scarcity mindset is a holdover from gatekeeping systems. “The more of us who succeed, the stronger we all get,” he noted.

Scarcity vs. Abundance: Rewriting the Playbook

This cultural divide—scarcity versus abundance—was a recurring topic. Scarcity leads to secrecy, ego, and undermining collaborators. Abundance, on the other hand, fosters partnership, mentorship, and mutual elevation.

Daniels, Hoffa, and Omile agreed that too often, creatives are left to fend for themselves because no one taught them otherwise. Deals get passed over, opportunities are missed, and resentment festers. “Imagine if every time I signed a deal, I shared the playbook,” Daniels said. “We’d all be in better rooms.”

Leadership, Loneliness, and the Weight of Vision

Leadership isn’t always applause and accolades. Often, it’s lonely, especially for Black creatives and entrepreneurs navigating spaces where they’re the first or the only. Hoffa shared that he often felt like a solo soldier, managing the logistics while peers chased clout.

“You think you're building a team, but they think they're building a brand,” he said. The lesson? Clarity upfront—define roles, draft contracts, and set boundaries. Hoffa has since tightened his circle, even instituting non-compete clauses to protect his creative investments.

Vertical Integration: Lessons from Hip-Hop’s Billionaires

Everyone on the panel drew inspiration from moguls like Jay-Z, Diddy, and Kevin Hart—figures who understood that content is only the beginning. The real power lies in what that content promotes: liquor brands, festivals, clothing lines, or platforms.

“This ain’t just about getting views,” Daniels said. “It’s about turning those views into value.” Whether it’s The Cut or My Expert Opinion, the content should serve as a gateway to something more permanent, more lucrative.

Mentorship and the Circle of Trust

Another powerful takeaway was the importance of mentorship. Omile credited much of his progress to founders and investors willing to pick up the phone and share knowledge. Hoffa, by contrast, had to carve his own path, often rebuffed by peers who saw him as competition.

“We need to normalize sharing our wins—and our lessons,” Omile said. “If one of us learns something, all of us should know it.”

Empowerment Through Authenticity

The thread running through the conversation was clear: authenticity wins. Whether it’s rapping in a barbershop, pitching investors, or building an audience online, success comes to those who stay true to their vision and build with integrity.

From freestyles to funding rounds, this story was about more than music or tech—it was about creating lanes and passing the blueprint along. The freestyle tour was proof that barbershops are still ground zero for cultural impact. And that when the right people come together, real change happens.

Stay Ready, Stay Real

As the conversation wrapped, there was a renewed call to action. Share the knowledge. Build the network. And never forget that culture, when stewarded correctly, is an ecosystem of opportunity.

So if The Cut tour rolls into your city, show up. Rap, learn, connect. Because whether you’re behind the mic, behind the app, or behind the lens, the work of building legacy starts now.