Sterling grew up in the suburbs of Minneapolis. As a kid he loved skateboarding but mostly did street riding. He injured his ankle badly when he dropped into his first half pipe. His skateboarding slowed down after that, but he still loved the sport. While in his 20's he needed to make a change, so he did some world traveling with a motivational speaking group. Through it all, he visited 46 states and 3 continents and eventually lived in Mississippi. In 2005, Hurricane Katrina tore through the state. He jumped into the fray, helping mobilize support for the evacuees of New Orleans & The Gulf Coast. During the aftermath he helped run a shelter and drove food & medical supplies to affected areas by truck. Currently he lives in Minneapolis, runs his snowboard shop, and shreds Vail Whenever he can.