Sterling recorded his first song with his grandfather at the age of 6. His grandfather, a musician himself, introduced him to the sounds of Sam Cooke. When he was 15, his mother moved the family of four children to Atlanta. There Sterling began to make the rounds with Dallas Austin, Jermaine Dupri and other music makers in the city.
After a period struggling, Sterling began to focus on writing, putting his artist ambitions aside. Returning to Philadelphia, Sterling reconnected with Kenny Gamble. Back in Atlanta, Sterling met up with producer Teddy Bishop, who liked the songs Sterling was working on. Bishop asked, "Who was the voice behind the songs?" At Teddy's prompting Sterling decided to pursue becoming a performer again. He sang for Lyor Cohen, Kevin Liles and a group of other influential music executives, giving them Sam Cooke's "A Long Time Coming." They were impressed with Sterling and by this time Warner Bros and Atlantic were very interested in signing him. While waiting for an offer, Sterling traveled to Miami with Bishop to the VMA’s. Bishop played Sterling’s music for industry veteran George Robinson. Robinson recognized his talent at once and convinced the partners of One Recordings to make Sterling their first release.