Ryan began his career in skeleton in 1992 when he noticed a newspaper article on the sport. He immediately fell in love with the sport and began training. During the 1990s he won seven gold medals at the Canadian Skeleton Championships until his retirement in 1999. He also garnered two gold medals (1996 and 1997) and a bronze medal (1995) at the World Skeleton Championships. Unfortunately, skeleton was not yet recognized as an Olympic sport.