His father was Captain (later Major General) Robert Oldys (later Olds), Olds virtually made daily contact with the small group of officers who would lead the US Army Air Forces in World War II (one neighbor was Major Carl Spaatz, destined to become the first Chief of Staff of the USAF), On November 10, 1925, his father appeared as a witness on behalf of Billy Mitchell during Mitchell's court-martial in Washington, D. He brought three-year-old Robin with him to court, dressed in an Air Service uniform, and posed with him for newspaper photographers before testifying.
His father was made commander of the pioneer B-17 Flying Fortress 2nd Bombardment Group at Langley Field on March 1, 1937, and promoted to lieutenant colonel on March 7.
Olds attended Hampton High School where he was elected president of his class three successive years, and played varsity high school football on a team that won the state championship of Virginia in 1937.
Olds was aggressive, even mean, as a player, and received offers to attend Virginia Military Institute and Dartmouth College on football scholarships.
The remainder of his career was spent in non-operational positions, as Commandant of Cadets at the United States Air Force Academy and as an official in the Air Force Inspector General's Office.
His inability to rise higher as a general officer is attributed to both his maverick views and his penchant for drinking.
After he received a conditional commitment for nomination from Pennsylvania Congressman J.
Buell Snyder, Olds moved to Uniontown, Pennsylvania, where he lived in the YMCA and supported himself working odd jobs.
As a plebe, Olds played football on a freshman squad that began the season with three losses but finished 3–4–1 while the varsity won only one game in its second consecutive losing season. At 6 foot 2 inches in height (1.88m) and weighing 205 pounds (92 kg), he played tackle on both offense and defense, lettering both seasons.
Army's record in 1941 was 5–3–1, with wins over The Citadel, VMI, Yale, Columbia, and West Virginia, a scoreless tie with Notre Dame, and losses to Harvard, Penn and Navy.
In the Army–Navy Game of 1942, which was played at Annapolis instead of Philadelphia, Olds had both upper front teeth knocked out when he received a forearm blow to the mouth while making a tackle.