Celebrating the latest visionaries breaking new ground across art, sustainability, food and technology, Bulleit Frontier Whiskey’s Pioneer Project spotlights changemakers shaping the frontier of culture. The Pioneer Project, in partnership with the record label and music distribution platform UnitedMasters, has provided over 100 hours of mentorship to emerging creators, this year spotlighting recording artist Oke Junior (Matthew Osivwemu). In Bulleit Frontier Whiskey’s latest campaign, A&R executive Sickamore (aka Randall Jesse Medford) and UnitedMasters rap artist Oke Junior unpack their beginnings in the music industry and the learnings that informed their success. In the interview below, the mentor and mentee duo open up about parallel experiences that have defined their outlooks on music, collaboration and branding, allowing them to turn ideas into movements.

A legend in his own right, Sickamore is behind some of rap’s most groundbreaking artists and platinum albums of the 21st century. The former Senior Vice President of A&R and Creative Director at Interscope Records and now the founder and CEO of IIIXL Studio, Sickamore embodies the makings of a mentor and music historian, studying hip-hop’s evolution alongside the leading voices shaping its trajectory in culture. Working closely with blockbuster acts like YG and Travis Scott, the Trinidadian-born music maverick laid the building blocks of his career early on as DJ, nurturing his love of hip-hop through mixtapes he sold across Brooklyn and Manhattan.

“You learn a lot about people, business, sales — it was the best kind of introduction to the game that I could possibly have. From there, being able to take those skills, I was able to leverage independent A&R jobs,” says Sickamore. By eighteen, he had mastered the art of the mixtape in the era of Napster and battle rap studio sessions. Internships with producer Just Blaze and a Director of A&R position at Atlantic Records solidified his precocious presence in music.

“The best times I’ve had working with an artist is when we lock in on a concept, an idea, an ethos, something that we both can agree on and then we’re able to follow it. The smartest artists don’t look at themselves as the artist — they almost navigate the world through an avatar,” comments Sickamore. In this sense, Sickamore notes how part of his expertise is mapping out the product of an artist’s labor and discerning the salable parts of that concept that remain evergreen in execution. “They’re able to kind of step out of it and look at it objectively. And when you [can] do that, you [can] have harsher conversations or you [can] talk from a place that’s not personal.”

For unsigned artists, deciphering who’s in your corner and who’s your Achilles heel is precarious business to maneuver. Born and raised in Oakland, California, rap artist Oke Junior eventually moved to Napa at ten, where he began exploring his love of beats and lyricism with his brother — someone he attributes to supporting his craft. Together, they mixed CDs on GarageBand, performed talent shows and created a hometown rap group. With the passing of his father, Oke Junior dedicated his artist name to his memory, committing himself to his music and brand.

“There [were] a lot of trials and tribulations — dealing with promoters, trying to book your own shows, music videos — the whole funding process. It was real difficult for me, but I’ve been doing this since I was 10 years old. Compared to a lot of my peers, they don’t understand the steps that come with this. It’s a lot of groundwork — it’s not an overnight thing.”

This level of determination rings true in Oke Junior’s music, where dodging “janky” promoters comes with the territory of having something to say. On his 2018 album, Outside Looking In, tracks like “Golden Child” see the artist weathering setbacks and pitfalls many independent artists face in their careers with maturity and tenacity.



“I haven’t dropped a full-length project in four years,” counters Oke. “I put a lot into [I Don’t Follow I Lead]. I did it independently, from the music videos to getting it on the radio to hosting the album release party and everything.”

Oke Junior admits he’s finally ready to build off the momentum of his 2020 album, I Don’t Follow I Lead. Returning to Napa, he found himself at a crossroads with music, pivoting to teaching and community-led projects that could help redefine his place in the industry. In 2022, an appearance on Sway in the Morning, hosted by Sway Calloway, revamped his confidence. At the moment, a new project is in the works, a rebirth that, for Oke, feels honest to his journey as a lyricist. Most recently, the rapper has sync placements with ESPN, the NFL and Wingstop — yet another accomplishment showcasing his hunger to platform his music to larger audiences, amassing 2 million streams across Spotify, YouTube and Apple Music combined.



Describing how artists are up against gatekeeping and the bureaucracy of major record labels, Sickamore jokes that A&R in 2024 stands for “Artists and Research,” noting that social media, streaming services and algorithms are virtual roadblocks all recording artists will, at one point or another, face head on. “I want people to see that putting back time in the community [and] working with artists isn’t played out. I hopefully lead by example to create a generation of community leaders,” closes Sickamore.

“I was showing Sickamore some of my new album, and he told me straight up, ‘Add this, you can move this, move this around,’” says Oke Junior. “As artists, we gotta be willing to be more receptive to this feedback and know it’s coming from a genuine place, that the team is right.”

Fostering this sense of mentorship starts at the ground level, where trailblazers like Sickamore lead innovative talent to the front of the pack. Sickamore’s and Oke Junior’s appreciation for tapping into their immediate communities and sifting gold from everyday experiences inevitably builds the stepping stones for future artists. Visit Bulleit’s website to learn more about the Bulleit Pioneer Project.

DISCLAIMER: We discourage irresponsible and/or underage drinking. Drink responsibly and legally.