A native of Richmond, Virginia, Drew began playing the trumpet at the tender age of 6. In 2008 his father, a jazz pianist founded the Richmond Youth Jazz Guild which catapulted Drew's improvisational skills and love for jazz. At 12, Drew was riffing alongside Trombone Shorty and learning from the late Frank Foster. By age 14, Drew had an audience of jazz giants like Quincy Jones and Wynton Marsalis. His apprenticeship in jazz continued as he earned coveted scholarships to attend Berklee College of Music in Boston for three consecutive summers. While attending these summer intensives, Drew further developed under jazz musicians like Terri Lyne Carrington, Phil Wilson, and Tiger Okokshi.

Drew's journey in jazz continued after graduating from high school in 2015. That year, he was selected to participate in the Jazz at Lincoln Center inaugural Summer Jazz Academy. This prestigious program assembled 43 of the nations top high school jazz musicians to learn under Wynton Marsalis and the musicians from the JALC Orchestra. Currently, Drew resides in New York City and attends The New School for Jazz and Contemporary Music. He is expected to graduate in May 2019.