Naive John was born Ian Wylie in Poole, Dorset, his family moving to Glasgow when he was two years of age. He attended Cumbernauld High School, Glasgow 1973–79. During the period 1979–83 he took part in a youth training scheme, where amongst other things he played cards. In 1983 he was accepted without academic qualifications as an exceptional student at Greys School of Art, Aberdeen, but was later expelled. Within two years he had sold a painting "Yellow Envy" to Edwin Morgan, Scotland's Poet Laureate and won an award for his short experimental animation film Phobia. In 1998 he fled to Liverpool after a homophobic knife attack. Intensive psychotherapy followed during 1998 in an attempt to come to terms with his past traumatic experiences. He has since been diagnosed as suffering from dysthymia. Throughout his periods of illness he continued to produce drawings and paintings albeit in limited numbers. Ex-Vaselines front woman Frances McKee commissioned the artist to create several CD covers for her band Suckle.