DeVaughn took a job at Tower Records, where he put price tags on CDs. During that time he also began working the D.C. music circuit—performing with various groups, the most prominent of which being Urbanave31, and at venues such as the State of the Union and Bar Nun on U Street NW, all while having CDs of his songs ready at hand. Locally in the DC Metro area he attained relatively quick success, winning local awards and successfully releasing some independent work over the next few years. He won $2,000 from the Washington DC nightclub Bar Nun talent show. CEO Cliff Jones (Soul World Entertainment) and partner Jerry Vines, now the singer's longtime manager, met DeVaughn while managing the Baltimore-based quartet Dru Hill, and asked him to write a song for the group. DeVaughn ultimately gained the attention of record producers DJ Jazzy Jeff (as Rahiem) and Kenny Burns (known as former A&R for Roc-A-Fella Records) and with the help of Jones and Vines they signed a recording contract with Jive Records in 2002.