A versatile trumpeter and arranger, Rashawn Ross started his musical journey from humble beginnings in St. Thomas, U.S. Virgin Islands. While attending Charlotte Amalie High School, Ross began performing and traveling with some of the island's most popular calypso and dance bands. Upon graduation from high school in 1996, Rashawn attended Berklee College of Music in Boston, Massachusetts, Graduating in 2000.

Jazz was the foundation of his passion for music, a love that he inherited from his father who was a jazz enthusiast. Although jazz is a huge influence in his life, Rashawn has compiled a large résumé with artists in many different genres ranging from funk, jazz, rock, hip hop, r&b, soul, pop, latin, calypso, gospel and country.

Ross has toured with Yerba Buena, Lettuce, Soulive, DJ Quik and Usher. Rashawn began working with Dave Matthews Band in 2005 and became a permanent fixture in the band on the road and in the studio. Named highest grossing touring act of the decade, they sold more tickets to their concerts than any other act in the world between the years 2000 and 2010. Dave Matthews Band is also the only band in history to have SEVEN consecutive albums debut at #1 on the billboard charts.