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 Positivewebcomic, 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.
In June 2004, faced with increasing complaints about his lateness in updating the comic, Milholland challenged his readership to donate enough money to pay for a year of his salary so that he could quit his job and become a full-time cartoonist.[3][6][7] To his surprise, this amount was reached and surpassed in less than a month, making Milholland one of the successful pioneers of micropatronage. Since then, his webcomic has expanded into many realms of merchandising.[8][9]
Milholland has relocated to Texas and travels the con circuit frequently. He also sometimes performs in community theater, especially children's theater. In 2017, he moved to Georgia.[10] In 2019, he moved back to Texas following the signing of Georgia House Bill 481, a so-called "fetal heartbeat bill", into law.[11][12]
Comics
Something Positive
Something Positive started its run on December 19, 2001. As of December 21, 2023[update], it is still being actively updated.
Something Positive 1937
Starting on September 7, 2007, Milholland launched a third spin-off from Something Positive, this one also taking place in the same continuity as the original but taking place many years earlier. Something Positive 1937 follows the relationship of Fred's father Vester Macintire and his cousin Davan (Davan of S*P's namesake, first mentioned in the comic's May 8, 2007 strip.[13]) The comic is in black and white and for a time featured in a sidebar next to the original, with archives available on the same page as the original strip. Milholland said in news posts he expected the story to last for a few years, and provided it with its own website[14] on September 24, 2007. The strip stopped updating in 2008.
Midnight Macabre
Midnight Macabre is another spin-off from Something Positive. It features Gaspar Baugh, the father of Something Positive secondary character Lisa Baugh, as he attempts to resurrect a horror TV show presenting Midnight movies.
New Gold Dreams
New Gold Dreams is a strip that spoofs the conventions of the heroic fantasy genre. It also ties in with Milholland's interest in role-playing games, as the comic is portrayed as a game run by Pee-Jee, one of the main strip's cast members; some of the characters in New Gold Dreams have the same appearance and personality as regular S*P characters. The comic started on April 2, 2004 but has been entirely on hiatus since the 20th issue in August 2005.
Super Stupor
Super Stupor is a superhero comic, which mocks the conventions of the genre. Four self-published volumes of the strip are currently available from the Rhymes With Witch store.
Popeye
Popeye is a newspaper comic strip from King Features Syndicate, starring an ornery sailor and a large cast of quirky characters. In 2022, Popeye's 93rd year, Milholland took over the Sunday edition from Hy Eisman as the latter retired.[2]
Mousetrapped
In January 2024, with Mickey Mouse's original version of Steamboat Willie becoming public domain, Milholland released the webcomic Mousetrapped.[15] Set after the events of the short, the story follows Mickey struggling to make ends meet after getting fired by Pete and features a cast of other public domain cartoon characters.
^"Upcoming". Something Positive. July 3, 2019. Archived from the original on Feb 11, 2023. Immediately after that, my wife and I will be packing up our stuff, cats, and probably our baby and moving from Savannah, Georgia to San Antonio, Texas