Sickamore on Working With Lifelong Mentor Kyambo “Hip Hop” Joshua and Mentoring Rap Artist Oke Junior

Business of HYPE returns as a Limited Series with new host Awake NY founder Angelo Baque and Inaugural Guests Kim Shui and Vashtie.

In the latest episode, Angelo Baque speaks with the founder of IIIXL Studios and A&R executive Sickamore (Randall Jesse Medford), and rising rap artist Oke Junior (Matthew Osivwemu) to discuss their experiences being a part of Bulleit Frontier Whiskey’s Pioneer Project. In partnership with the record label and music distribution platform UnitedMasters, the program has dedicated over 100 hours of mentorship to emerging artists, helping them navigate branding, producing, licensing and more.

Trinidadian-born music maverick Sickamore got his start in the music industry in his early twenties, landing an internship with DJ-Producer Just Blaze and a full-time position at Atlantic Records as a Director of A&R. He’s launched artists like Travis Scott and YG, and has most recently founded IIIXL Studios, in partnership with Soundcloud. Inspired by his professional experiences while traversing Brooklyn and Manhattan’s hip-hop cohorts, IIIXL Studios champions rising artists home to New York looking to hone their craft alongside industry legends. Speaking with Baque, Sickamore opens up about mentors who’ve provided him with guidance and grace throughout his professional development. 

“Mentors have been a vital part of my career. I think the most important mentor I’ve had is a guy named Kyambo “Hip Hop” Joshua. He took me under his wing when I was nineteen years old, and I would follow him around, asking him questions. He showed me the role of an A&R, and he had a really illustrious career. He found Kanye West and started a company called Hip Hop [Since] 1978.”

Paired with Oke Junior as a mentor during Bulleit’s Pioneer Project, Sickamore has aided the artist in refining his upcoming album, The Revamp, his first release since 2020, but he’s also provided insight into some of the pitfalls that all artists are responsible for steering early-on in the game.

“It’s tough. It’s tougher than ever to be an artist because everything gets so scrutinized. You feel like every post —everything — is like walking a tightrope. The bigger you get, the tightrope gets a little higher. You go from one floor to the Empire State Building. So every post, every tweet, everything has to be part of your mission and has to become authentic. And sometimes kind of pulling back from that and just focusing on the music [helps].” Referencing Oke’s mentorship, Sickamore offers a few words of advice in terms of managing celebrity alongside his art. “You know why you’re here, the mission and the story of what you are. That end of the day when you’re an artist, you have something to say, and [just] making sure you kind of stay focused on that and not all the trappings of ‘Oh, I gotta do these TikToks, and I gotta post this and I gotta do that.’”

Born and raised in Oakland, California, Oke Junior is a lyrical force with a keen ear for nostalgic production reminiscent of Mac Dre and Too Short — Bay Area artists who continually serve as inspiration in his music. You can hear these references on albums like I Don’t Follow I Lead (2020) and Outside Looking In (2019), along with artists such as Kanye West, Snoop Dogg, 50 Cent and Lil Wayne. 

“I’m from the Bay Area — Oakland, it’s a small area. We don’t get a lot of light and attention, especially being the type of artist that I am. I’m more of a lyrical artist. And that type of sound isn’t the sound of the Bay Area. It’s just a different type of vibe out there. So just learning how to just stay authentic to myself and not get too caught up in what everyone else is doing. And just find ways to maneuver in the industry while being independent.”

Propelling his work forward while remaining unsigned is a feat all on its own, but Oke Junior has never viewed that as a deterrent — only motivation to stay true to his voice. 

“I see myself being a household name, traveling the world, and building my brand.” He’s set his sights on evolving and growing alongside music pioneers like Sickamore, who’ve worked in music long enough to know when there’s gold on the horizon. 

As always, thank you for tuning into Business of HYPE. Dive into the full episode featuring Kim Shui and Vashtie on Apple Podcasts and Spotify, and read more about UnitedMasters’ artists spotlighted in Bulleit Frontier Whiskey’s Pioneer Project.