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Kelsey comes from a rowing family, and has been around the sport of rowing for his whole life at all levels. Following his father's lead (former stroke seat for UBC/Canada in '68-'70) he took up the sport at 14 while attending Shawnigan Lake School under. While at SLS, Kelsey competed a number of times at the National High School Regatta, earning a number of medals.
Following high school, he attended the University of Washington under John Parker and Bob Ernst, where he lead his crews to top three finishes in the American Collegiate Championships (IRA regatta) each year. During this time he also trained with the Canadian National Team, and trained with and against many Canadian and American Olympic and World medalists. As well, his younger brother is currently a member of the Cambridge Blue boat, (following a very successful rowing career at Harvard,) and is also the stroke seat for the Canadian National Men's 8+.