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Caleb, originally from Columbia, SC, first learned about show business when he played mandolin and bass with the Denver-born alternative country & western band Slim Cessna's Auto Club in 1994 while a student at the University of Colorado.

Drawn back to the bluegrass he grew up listening to from his father's record collection, he founded Open Road in 1999 with Bradford Folk and was recognized for his deep heartfelt classic style of mandolin playing. Open Road wasrecruited by Rounder, recorded three CDs with the label, and toured heavily for five years until retiring in 2006.  Open Road reunited for a Rockygrass performance in 2011.

Caleb began playing electric guitar and building tube amplifiers in his garage in Lyons, CO, and he played with the Billy Pilgrims from 2006-2008. He also occasionally subbed as a Clyde when Taylor was unavailable.

He joined the Clyde family on bass in August 2014.