Born in Owatonna, Minnesota. Underland soloed in 1956. He began his aviation career as a crop sprayer, worked on aircraft maintenance and gave flying instruction. Later, he formed a close association with entrepreneur Buzz Kaplan and flew with Kaplan on many long distance flights, including those to Siberia, the Arctic Circle and Europe. Underland maintained the Kaplan airplanes and managed construction of several vintage seaplane recreations basically from drawings. Along the way, Underland’s natural engineering talents also saw many other antiques restored, both Kaplan’s as well as his own. Underland worked with and mentored many young aviators to teach them flying and to build their own aircraft.