Derrick’s family was close-knit, musically gifted and devoted to God. Because of this, church services would play an integral major role in his musical development. His first public performance would be in the church choir where he was exposed to the complex choral arrangements and harmonies of Gospel music. In addition, his family performed concerts, acting as a choir on its own. However, it would be at the age of seven when he would have his first performance televised on the local news show. By the 2nd and 3rd grade, he was already developing as a writer and songwriter, writing lyrics, essays and writing contests. In 1983 Derrick joined the Navy. As he was “sailing the seven seas” he began to perform R&B while stationed in Italy. He loved being on stage and feeling the energy of the crowds. While he enjoyed the melodies and arrangements of the genre, he felt R&B was simply too risqué. His musical experiences in Italy, however, would be vital in developing his stage presence and songwriting skills. He left the Navy in 1987, but continued down the path of music. In 1999, he began performing with Gospel group Forgiven. He joined SetApart in 2001, and he continued to perform with them until 2009. Derrick has had the opportunity to perform twice at the National Gospel Music Workshop of America. His performances in New Orleans and Kansas City attracted attention from Light Records. This interest was profound for him, as it was the same label The Winans were signed to.