Isles played football and participated in track and field at Jackson High School in Ohio, where he holds school records in the long jump, 100-meter, 200-meter and 400-meter events. He was an All-American in the 60 meter dash at Ashland University, running a personal best of 6.68 seconds. Isles was also an All-GLIAC selection on the Ashland University football team and still holds school records for most kickoff return yardage in a game and longest kickoff return for a touchdown. Though his 100 meter time of 10.13 seconds would have been good enough for the semi-finals at the London 2012 Summer Olympic Games, Isles did not attend the Games. He began his rugby career shortly thereafter with the Gentlemen of Aspen Rugby Football Club and earned a Residency contract with the Men’s Eagles Sevens. Isles was one of the leading try-scorers on the Eagles during the 2012-13 IRB Sevens World Series.