Bob was born on March 31, 1970 in Cardiff New Jersey and attended Egg Harbor Township High School. After studying at Richard Stockton College of New Jersey Bob worked as a production assistant and technician at TV studios and in film production, which took him to Charlotte, North Carolina. After a couple of years in the film industry Bob decided to become a music theory teacher so he enrolled at Winthrop University in Rock Hill, South Carolina in 2000, studying jazz guitar.

Bob played electric bass guitar for the bands Blue Green Gauge and The Memphis Quick 50 for a couple of years before joining The Avett Brothers in March 2001. Apart from his studies at Winthrop he was performing with local bands to make ends meet before he was contacted by Seth and Scott to audition for their band. The legend goes that Bob had been playing the upright bass for only a few weeks before he was approached by the brothers to join the band. They played a handful of songs — some originals from their debut EP and some covers, including Woody Guthrie's "Worried Man Blues" — in a record store parking lot as the audition. Seth and Scott drove to San Francisco to play near Pier 39 before returning a month later to ask Bob to join the band. During their early days, Bob pushed the band to tour outside of their comfort zone of North Carolina. He was with the band as they recorded all albums from Country Was forward.