In 1991, Dave Matthews asked Tinsley to play violin on the song "Tripping Billies" with his band for their demo tape. Tinsley left his existing band (the Boyd Tinsley Trio) to join Dave Matthews Band. He became a full-time band member in 1992. Matthews later said, "We had no plans of adding a violinist. We just wanted some fiddle tracked on this one song "Tripping Billies", and Boyd was a friend of Leroi. He came in and it just clicked. That completely solidified the band, gave it a lot more power."