While working as a carpenter with his father, he lost part of his left index finger , which did not affect his ability to later hold a palette while painting. In , year-old Ross enlisted in the United States Air Force and was put into service as a medical records technician. He developed his quick painting technique during brief daily work breaks. During his year Air Force career, Ross developed an interest in painting after attending an art class at the Anchorage U. 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. Ross studied and mastered the technique, began painting and then successfully selling Alaskan landscapes that he painted on novelty gold-mining pans. He retired from the Air Force in as a master sergeant. He returned to Florida, studied painting with Alexander, joined his "Alexander Magic Art Supplies Company" and became a traveling salesman and tutor.
Annette Kowalski, who had attended one of his sessions in Clearwater, Florida, [ 10 ] convinced Ross he could succeed on his own. Ross, his wife, Kowalski and Walt, her husband, pooled their savings to create his company. The business struggled at first; his trademark permed hairstyle came about as a cost-cutting measure when his regular crewcut haircuts were becoming too expensive. Ross later confessed that he disliked the hairstyle, but did not feel he could change it because it was depicted in the company logo.
In , a station in Falls Church, Virginia , aired a taping of his art class as a pilot, and 60 PBS stations signed up for the show in the first year. He moved home to Florida in but continued to travel to Muncie every three months to tape the show.
Ross said he did the show for free and made his income from how-to books, videotapes and art supplies. The show ran from January 11, , to May 17, , but reruns still [update] continue to appear in many broadcast areas and countries, including the non-commercial digital subchannel network Create and the streaming service Hulu. During each half-hour segment, Ross instructed viewers in the quick, wet-on-wet oil painting technique, painting a scene without sketching it first, but creating the image directly from his imagination, in real time.
