Bailey began playing bass guitar at age 12 and started playing fretless bass after he ran over his fretted Stuart Spector with his car. He started playing double bass after hearing Stanley Clarke playing with Return to Forever. He is Chair of the Bass Department at the Berklee College of Music. He has been a faculty member at Coastal Carolina University and the University of North Carolina Wilmington. He was also a faculty member at Hollywood's BIT for 10 years. He is a contributor to Victor Wooten's Bass/Nature Camp, which helps to teach bassists of all ranges. He is an avid tennis player and surfer.