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.
Since 2012, Anderson has received private instruction from several professional jazz trumpet players: Quincy Jones, Wynton Marsalis, Cecil Bridgewater, Jimmy Owens, Marcus Printup, and Charles Tolliver. Additionally, he has received two years of classical private instruction from trumpeter, Rodney Marsalis at the Curtis Institute of Music in Philadelphia. This form of learning emulates the jazz tradition of apprenticeship, which has been Anderson’s experience from his earliest days of study.