During his 20-year Air Force career, Ross developed an interest in painting after attending an art class at the Anchorage U.S.O. club. He found himself frequently at odds with many of his painting instructors, who were more interested in abstract painting. Ross said, "They'd tell you what makes a tree, but they wouldn't tell you how to paint a tree."[10]

Ross was working as a part-time bartender when he discovered a TV show called The Magic of Oil Painting, hosted by German painter Bill Alexander.[7]: 17–18  Alexander used a 16th-century painting style called alla prima (Italian for 'first attempt'), widely known as "wet-on-wet", that allowed him to create a painting within thirty minutes. Ross studied and mastered the technique, began painting and then successfully selling Alaskan landscapes that he would paint on novelty gold-mining pans.[5][9] Eventually, Ross's income from sales surpassed his military salary. He retired from the Air Force in 1981 as a master sergeant.[5][11][8][12]