Cargill was raised in a military family, growing up on army bases around the United States. He held several jobs prior to writing, including video store clerk and travel agent.[citation needed]
Cargill wrote his first article in 2000, when he volunteered to write a review of the movie Crouching Tiger, Hidden Dragon for a website called "Guerilla Films." His article managed to get the highest amount of traffic of over 50,000 hits, "a HUGE deal" at the time, which secured him the job to write more reviews.[citation needed]
While working for Guerilla Films, Cargill began spending time with Ain't It Cool News' Eric Vespe (AKA 'Quint' on the site), which landed him a job on Ain't It Cool's "Indie Indie Column," a previously abandoned post. He began writing for Ain't It Cool News under the name Massawyrm in May 2001. His first review for the blog was of Jon Favreau's movie, Made. During his work as a blogging critic, Cargill met various directors, which occasionally led to small roles in independent productions. In 2011, he told Jordan Gass-Pooré with Slackerwood that it was getting "tougher and tougher" to write movie reviews because of his relationships with people in the movie industry. "I've always had a strict code about writing about films made by people I'm friends with," said Cargill. "It's harder to write objectively about film without people feeling that you're being biased." Besides his work for Ain't It Cool News and his involvement with Spill.com, he also did freelance work for Film.com and Hollywood.com (the site that owned Spill.com).

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