Bob Wingo was born in Columbus, Ohio, to Robert Charles and Louise Elizabeth Wingo. Wingo’s father was a World War II veteran and career officer in the United States Army. He was stationed in South Dakota and Okinawa, Japan, before the family settled in El Paso, Texas, at Fort Bliss. Wingo himself was drafted into the Army in 1968 and served in the Vietnam War. He was wounded twice and was later awarded a Purple Heart. After an honorable discharge, Wingo enrolled at the University of Texas at El Paso (UTEP) and graduated in 1973 with a bachelor's degree in marketing.