In the ninth grade, he left school to help his father in his carpentry job. While he was helping his father, he lost the tip of his left index finger. When he was 18, he joined the Air Force which moved him from his Florida home to Alaska. During his 20 year tenure with the Air Force, Ross developed a taste for painting after attending an art class at the Anchorage U.S.O. club (Today I found out). Eventually, he became inspiration from a television show. At that point, he started his work of painting. He started to paint and show it off to his friends and family. They started telling others of his work, and he became popular. He started to make money off of his art, and started to become more popular than he thought he would (BobRoss.com).
After leaving the Air Force, he returned to Florida during the 1980’s. He sought out the man who inspired him to learn from him. Bill Alexander accepted his offer and taught him everything he needed to know. Once he learned, he started to paint even more pieces of art. After some time, Bob got a job offer from Alexander Magic Art Supplies Company as a tutor