Dempsey has attended the University of Kentucky and transferred to graduate with a bachelor’s in Communication from ETSU. He started his professional career with WAXU-AM-FM radio in Georgetown, Ky., and worked as an account executive for WKYT-TV in Lexington, Ky., and WOWK-TV in Huntington, W.Va., before moving to the Tri-Cities in 1985. In August of 1985 he joined WJHL-TV as general sales manager. Dempsey then became president and general manager of WJHL-TV in May 1989. He is actively involved with numerous organizations in the Tri-Cities, such as the Rotary Club of Johnson City, Barter Theater Board of Directors, United Way of Greater Kingsport Board of Directors, the Johnson City and Bristol Chamber of Commerce.