Guess was raised in the Preston Taylor Homes public housing project in Nashville.
[1] He served in the United States Army in the field of military intelligence, and was in the 1st Infantry Division during the Vietnam War.
[1][2] Following the war, Guess enrolled at Tennessee State University, where he earned a bachelor's degree in political science.
[1] He also received a master's of business administration (MBA) from the Owen Graduate School of Management at Vanderbilt University.
[1] Guess also completed Harvard University's Senior Executives in State and Local Government program.