For aspiring musicians, success is a road rarely traveled alone. Behind every blockbuster act is an A&R, an agent, a manager, a videographer and more, shaping the trajectory of an artist’s career. For independent creators, these connections are anything but free. Bulleit Frontier Whiskey’s Pioneer Project, in partnership with the record label and music distribution platform UnitedMasters, has provided over 100 hours of mentorship to emerging creators, among them multidisciplinary artist SIRA (Marissa Lewis) and rap artist Oke Junior (Matthew Osivwemu).
The program aids artists in refining their artistic disciplines, propelling their work forward by exploring the idiosyncrasies of collaboration, music production, branding, finances and more. In partnership with Hypebeast, multidisciplinary artist SIRA and rap artist Oke Junior were paired with respective mentors, Artist Manager Ebonie Ward and A&R Executive Sickamore (Randall Jesse Medford) — two industry legends in their own right — who’ve molded the contemporary landscape of rap and hip-hop genres. The campaign culminated in a panel, “The 100 Hour Rule: Lessons on Navigating the Music Industry,” held at Hypebeast’s 41 Division location, where the creators discussed the benefits of mentorship and collaboration.
Replete with an open bar serving signature Bulleit cocktails, the event saw music and fashion lovers across diverse creative industries join together to celebrate the accomplishments of UnitedMasters artists SIRA, the NYC-bred songstress and multidisciplinary artist behind The Stars Between My Teeth and rap artist Oke Junior, a lyricist and poet hailing from Oakland, California, and the lethal wordsmith behind I Don’t Follow I Lead and Outside Looking In.
“I think one thing that Ebonie has constantly reaffirmed and that has shifted things for me is to let people in on the process more. Most of the time, I think of the final product, right? I only want people to see this finalized version, the perfected version, but she has flagged the beauty and the steps that lead you there and showcasing that letting people in [those] contexts is just as important,” said SIRA.
As a multidisciplinary artist, SIRA has built robust communities in fine art, fashion, lifestyle, music and film, applying a DIY mindset to her works-in-progress. “It feels like endless support in the ways that they can overlap and connect. Overall, I think artists of our generation are yearning to express themselves in a multitude of ways,” said SIRA. Her cross-disciplinary leanings have earned her an artist residency at the EFA Project Space. Exploring her sound through moving images, a self-funded short film, currently in post-production, accompanies her latest EP.
As for Oke Junior, the rapper notes that working alongside Sickamore was equally surreal. Settling into his mentorship, he realized the A&R juggernaut was, indeed, just a phone call away. Working with UnitedMasters, he mentions how impactful the process was to his work and life. “I’ve been able to get different sync deals, from ESPN to [the] NFL. I wrote and recorded a song for AT&T and Wingstop. It’s been helpful as far as putting my stuff back into the world. I’m also a teacher and work with different schools in the Bay Area and Sacramento. It’s crazy [being] a mentor in that sense because a lot of the game I get from [Sickamore], I put back into that.” The artist is currently in the throes of a new project, entitled The Revamp, following a four-year hiatus from music.
Representing themselves as industry leaders and embodying the role of mentors, Ward and Sickamore have played an instrumental part in their journeys with UnitedMasters. Neither of them were handed their careers on a silver platter. Ward, in particular, has sourced visionary talent to man her woman-led management company 11th & Co., working closely with CFO Alexandria Kindle, Chief Marketing Officer Jenna Magee-Tyson and Chief Legal Advisor Zita Brack, among others, behind the scenes to uplift Black artistry. “I was very intentional in the inception of my company and my brand coming into the business. I was one of the very few Black women who entered this space. I started as an assistant. I worked my way up from an assistant to a brand manager to a day-to-day manager to an owner of a company. I didn’t skip any steps,” commented Ward.
The music industry has a language of its own. Ward helps artists understand it and discern how to leverage creative opportunities. “We are so intelligent, we’re so powerful. I just wanted to create a space in the community where Black people and Black women could encourage and empower each other — somewhere we can thrive and build something beautiful. As Black women, we’re extremely nurturing. I think that’s what attracts a lot of talent to my company and my brand. As nurturers — we’re protectors, we’re safeguards. Everybody in this business wants to be protected, be seen and heard. That’s what my company represents. We’re eleven beautiful, talented, educated women empowering each other and safeguarding and protecting our client’s dreams and visions,” Ebonie said.
Sickamore paved new ground in the music industry with similar verve, landing coveted internships with Just Blaze to esteemed A&R roles with Interscope Records and Atlantic Records early-on in his career. He is credited with launching the careers of YG and Travis Scott, even developing Scott’s record label, Cactus Jack Records. In terms of solidifying his legacy in culture, Sickamore most recently founded IIIXL Studios, in partnership with SoundCloud, dedicated to platforming emerging artists based in NYC.
“I came up with the idea for IIIXL back in 2009. I recently resigned from a job, trying to hustle and manage, and nothing was shaking up for me.” The music maverick recounted journaling a letter to himself, where he envisioned his future life and career. “I wrote out my life. I kept that piece of paper in my pocket for five years. My whole career, up to this point, every job I got, every album, every opportunity has [gotten] me to this point. And now, launching this company, I have staff. I have people I can build with. I don’t look at it just as a business. I look at it as my purpose. I look back at that kid who was just in Chinatown writing dreams out.”
With IIIXL Studios, Sickamore is passing down his expertise in artist development and cultivating an environment that empowers artists to kickstart their careers in music. “I think in this new generation, there’s more money in the game than ever. I like to see when artists boss up because each artist is their own startup. They’re the founder, and they have to get people on. You see it in sports, people like LeBron James, they call it the ‘player empowerment’ movement. I think it’s happening. The artists are showing up to the meetings and they’re holding court. I think a lot of the artists that I work with are pioneering.”
During the panel, each creator highlighted how collaboration has influenced their careers, encouraging them to tap into a well of inspiration and join an ever-expanding cultural tapestry. Sharing their stories inspires the next generation to chart firsts in the music industry and weather shortcomings through authentic outreach. It’s not always a fun road to travel alone. Fortunately, SIRA and Oke Junior are in good hands.
Learn more about Bulleit Frontier Whiskey’s Pioneer Project by visiting the brand’s website. Stay tuned on Business of Hype to see more from UnitedMasters’ featured artists.
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