Trask spent his childhood in the mountains of the Pacific Northwest. Learning to ski at the age of 5, he continued camping, hiking, and skiing around the Cascades growing up until he enlisted in the US Army at 19. After going through the Special Forces Qualification Course, he became a Green Beret and was assigned to a Mountain Warfare Detachment with 1st SFG(A) out of Tacoma, WA. During this time, he graduated from several military schools including the Special Operations Mountain Warfare Training Center and US Army Ranger School. He led small units across technical rock, glacier, and alpine terrain throughout the Cascades, Alaska, and Asia, as well as instructed US and allied troops in mountain warfare. After transitioning out of the military in 2025, Trask has taken these skills into guiding in the Ski, Rock, and Alpine disciplines