Riley grew up in Colorado, graduating in 1997 from the Lowell Whiteman School in Steamboat Springs, Colorado and training on the freestyle teams at Winter Park Resort and the Steamboat Springs Winter Sports Club, both of which have produced many United States. Ski Team athletes and winter Olympians.
He graduated with a bachelor"s degree from Harvard College and earned master"s degrees from the University of Oxford and Yale University. In his last three years on the United States Ski Team, Riley attended Harvard University, where he was a humor writer for The Harvard Lampoon.
He then completed his Master of Arts in French Literature at Yale University. According to his Yale biography, Riley has a pet polish dwarf rabbit named Thibault after a character (Tybalt) in William Shakespeare"s play Romeo and Juliet and the pet lobster of the French poet Gérard de Nerval, a pet lobster that Nerval used to walk around Paris with a blue ribbon. On March 14, 1998, he competed in his first World Cup, which was in Altenmarkt-Zauchensee, Austria, and he placed 14th.
He got his first top-5 result on the World Cup the next season, finishing 5th in Dual Moguls in Madarao, Japan, on February 21, 1999 (he placed 6th the day before in Moguls).
In 2000, he was featured in the Warren Miller film "Ride.".
After finishing his Bachelor of Arts with high honors in Literature at Harvard University in 2007, he earned an M.St. with distinction and won the Gerard Davis Prize for the best dissertation on a topic in French literary studies submitted for the M.St. in Medieval and Modern Languages from the University of Oxford in 2011 (he was in the Queen"s College). Riley earned a spot on the United States. Ski Team in 1998, when he won the overall Nor-Am Cup in Moguls. A week later, he won the silver medal at the Junior World Championships in Jyvaskyla, Finland. Riley placed 2nd in a World Cup in 2001 and won Silver and Bronze medals at the Goodwill Games in 2000. He won his second United States National Championship with one of the highest scores in the history of the sport (a 2855) in Moguls in 2001 in Waterville Valley, New Hampshire.
