Jollett was born in Santa Monica in the experimental commune society called Synanon. Until he was five, he and his older brother were raised apart from their parents in Synanon schools. Jollett's father had been incarcerated in Chino State Prison from 1963-1966 prior to joining Synanon where he overcame a heroin addiction. Jollett's mother was a social worker with a master's degree from the University of California, Berkeley, who met Jollett's father in Synanon. When the commune became violent, his mother took him and his brother to live in Oakland and then in Oregon.
Jollett eventually moved to live with his father and step mother in Los Angeles, where he attended Westchester High School, graduating with a 4.3 GPA. During high school, Jollett participated in California YMCA Youth & Government's Model Legislature & Court program and served as the Speaker of the Assembly in 1992. He later attended Stanford University, graduating with honors in 1996. While at Stanford, Jollett was a member of Claude Steele's lab group in which he conducted research on the concept of stereotype threat. Jollett's work focused on how negative racial stereotypes negatively affected the identity and test performance of high school students.
In the summer of 2008, McSweeney's issue 27 published Jollett's short story, "The Crack", which appeared between short stories by Liz Mandrell and Stephen King. He was a frequent contributor to All Things Considered on NPR, the Los Angeles Times, an editor at large for Men's Health and the managing editor of Filter magazine. Jollett was accepted to Yaddo Writer's Colony in 2005 to complete his novel based on "The Crack", but did not attend, choosing to pursue music instead.

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