Duke began his career at a DMC World Championships after show party, where the winner of the MC battle competition got on stage and boasted that he would beat any rapper who challenged him. Duke climbed on stage to take the challenge, and emerged victorious. The battle was witnessed by Derek Bowland, who was acting as an A&R man for Music of Life records. He quickly arranged a meeting between Duke and Simon Harris, the head of the record label, where instead of bringing a demo tape, Duke rapped live in Harris' office. Harris agreed to sign him.