Winston Menzies, is the son of an Air Force pilot and Squadron Commander. He graduated from Texas A&M University with a B.S. degree were he also received his pilot's license and was commissioned a 2nd Lieutenant in the United States Army.
Upon entering active duty, he graduated from the Airborne, Ranger, Pathfinder, and Jumpmaster schools. He served as a platoon leader in the 82nd Airborne Division and was later selected to be aide to the Commanding General. Subsequently he volunteered twice to command rifle companies in Vietnam. After three years, He chose to resign his commission as a Captain to begin his business career. For his service he was awarded the Silver Star, two Bronze Stars, and two Army Commendation Medals.