When Josue Robles was three years old, his family moved to Ohio from his birthplace in Puerto Rico. In 1965, Robles was drafted, which started a 28-year career in the United States Army, during which he served in Korea, Vietnam, Germany, and Spain. Robles received multiple awards during his service, and finally retired from the Army in 1994. He decided to leave, partly because he had a son with autism who had a difficult time adjusting to the frequent moves.
Robles was on the board of the military financial services company USAA from 1990 to 1994, while he was still on active duty. He took over as CEO in 2007.