At the age of 16, Sickamore began to curate and sell instrumental hip-hop mixtapes on Canal Street in Manhattan.

Naturally, people took notice of his talent, intrigued by this hustle-minded kid boldly rubbing shoulders to make his name as a mixtape DJ. Five years later, in 2006, this venture landed him his first-ever A&R gig with Atlantic Records, at just 21 years old.