Reynolds encouraged Matthews' musical growth.

Matthews wanted to join Reynolds' band TR3, but Reynolds told him to form his own band.

Reynolds has occasionally joined the band in the studio, as on the albums Under the Table and Dreaming, Crash, Before These Crowded Streets, Big Whiskey and the GrooGrux King, Away from the World, Come Tomorrow and as a touring member of DMB.

By 1993, as a side project, Matthews and Reynolds performed several acoustic set shows, first on April 22, 1993.

[1] From this point onward, they always played acoustic, and they always played every year together (with the exception of the following years: 2000, 2001 and 2002), whether as Dave and Tim, Matthews guesting with TR3, Reynolds guesting with Dave Matthews Band, or Matthews and Reynolds playing in the band Dave Matthews and Friends.