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Born and raised in Philadelphia, R&B singer and songwriter Sterling Simms was heavily coached by his grandfather, a musician himself, to be a performer. He exposed Simms to classic soul artists like Sam Cooke and even helped Simms record his first song at age six. Inspired by new jack swing artists like Teddy Riley, New Edition, and Boyz II Men, Simms moved to Atlanta to pursue his singing career when he turned 14. He seized on the opportunity to work with up-and-coming producers (who were his co-workers at a car wash) when they established their own imprint and landed a deal through Sony. Due to restructuring, however, Sony eventually dropped the imprint, leaving Simms extremely frustrated. He moved back to Philadelphia, but was motivated to record again after hooking up with an old contact, ’70s Philly soul auteur and producer Kenny Gamble, who offered Simms free studio access.

Returning to Atlanta, Simms formed the songwriting company Knightwritahz with several other writers, since he was more comfortable writing for others in the background than being a full-fledged artist. Through his company, Simms wrote songs for several R&B singers, including Mario and Tyrese. However, after crossing paths with producer Teddy Bishop in 2004, he wanted to perform again, and great opportunities kept coming his way. He first signed with the indie label One Recordings, which led to his demo falling into the hands of Island Def Jam executive Antonio “L.A.” Reid. Simms was then picked up by Def Jam and even appeared on rap superstar Jay-Z’s comeback album Kingdom Come at 2006’s end. Around the same time, his single “Jump Off,” featuring rapper Sean Paul of YoungBloodZ, was enjoying regular rotation on urban radio.