Born in Kingston, Ont., Simon spent most of his time as a young child playing soccer. He competed in his first triathlon at age 11 when a family friend organized a race just north of his hometown. Simon and his friend decided to enter and see who would win. Simon says he competed in "boxer shorts with cows on 'em, and a Mickey Mouse hat." Although he lost to his friend, his life as an adrenaline junkie took shape, and he became more serious in his training for triathlons. Simon immediately began honing his skills in the local Canadian Kids of Steel program.