Bob Flaherty was born and raised in Boston and its surrounding towns and now lives in Western Massacusetts with his wife Annemarie, with whom he operates a birthday party business. They have 3 sons. Bob has, at various times, been an actor, a director, a cartoonist, a sportscaster, a talk show host, a tour guide, a storyteller, a disabled bus driver, a master of ceremonies, a hanger of gutters, a singer of national anthems and a baseball coach.