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Duncan was born in Stowe, Vermont. His parents homeschooled him from age 11 so that he could ski more often. Duncan finished 3rd in the 2008 Dew Tour, then 4th overall in the 2009 event. In 2009 he was the youngest men's competitor – at 16 – during the Winter X Games, taking 6th in the Superpipe finals. In the 2011 X Games Duncan found his way to 4th place in Superpipe. At age 17, he was named one of Powder Magazine's "20 Best Skiers 18 and Under" and graced that issue's cover.