Wilson grew up in Winter Park, Colorado, where his father was a ski patroller and ski instructor and his mom was also a ski instructor. He started skiing at the age of three, jumping at five and cross county skiing at the age of eight. Wilson won many Junior Olympic Championships, the last Colorado State High School Championship for jumping in 1982 and the Colorado State High School Championship in cross-country skiing in 1983. He was named to the World Championship Teams in 1985 and 1987, and the winter Olympic teams in 1988 and 1992. Wilson moved to Steamboat to attend Colrorado Mountain College and to train with the Steamboat Springs Winter Sports Club when he was about 21. Although Wilson had many strong North American performances, he was never able to get into the top 20 in the World Cup Nordic competition.
Wilson returned to Steamboat after competition and started coaching for the Steamboat Springs Winter Sports Club in 1992 and in 1994 became their Nordic Combined Head Coach. He was promoted to Nordic Director in 2000. Wilson has coached many athletes including Todd Lodwick, Johnny Spillane, Alan Alborn and more, who went on to national and Olympic teams. In 2003 he was a finalist for the U.S. Olympic Committee's Development Coach of the Year Award.
In May of 2002, Wilson married his wife Stephanie, who works for Vista Verde Guest Ranch in Clark, and their daughter Maggie was born in February of 2005.