Milholland moved to Boston in the spring of 1999. He worked odd jobs, including stints at a dot com startup, scientific non-profit, medical billing and medical research companies. During this time he started the "Something Positive" webcomic, in response to a criticism from his friend, voice actress Clarine Harp, that he should "do something positive" with his life. The protagonist in this comic, Davan, is loosely based on Milholland and the stories are often inspired by real life experiences. Davan's best friend Aubrey Chorde is based on Harp.