Randall "Sickamore" Medford may not be a household name, but if you're anywhere near the rap game you know he's been an integral part of the success of hip-hop heavyweights like YG, Travis Scott, and more.

Now a senior music exec at Interscope Records, Sickamore continues to play a key role behind-the-scenes for established and up-and-coming acts alike, and based on his track record, you'd be wise to bet on what and who he's working with. In our new episode of The Culture, Jinx chops it up with Sickamore to find out how the Brooklyn representative turned his passion for music into a career hip-hop heads could only dream of.

A major turning point in Sickamore's journey can be traced back to his days of selling bootleg mixtapes on Canal Street in Manhattan, which then led to an A&R gig with Atlantic Records at the age of 21.

The jump from hustling to corporate didn't affect Sickamore's drive, who saw the transition as an opportunity to capitalize on something he always believed. "I wanted to show people that you could really be in it. You can be on tour, you can be engaged, you can find records. You can make something," he explained. "You know how they always have that term for the culture? I understand it, but it's never been a point in my life where it's not been for the culture."

Sickamore's path hasn't always been on a positive trajectory. Two years after joining Atlantic, he left to start an artist development company and managed Nicki Minaj early in her career. His ambitions spread him thin, though, to the point that he lost Nicki as a client. That moment, while disheartening, helped Sickamore refocus his goals.

Check out the full episode above, where Sickamore talks about building a special bond with YG, how Travis Scott's "Antidote" was initially a freestyle, and also shares a hilarious encounter he had with Drake. DJ Clark Kent and Kyambo "Hip-Hop" Joshua also talk about their experiences working with Sickamore.