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.