Due to his parents' divorce, at age 4, Sheff spent much of his childhood bouncing back and forth between the San Francisco Bay Area and Los Angeles. He began using alcohol and drugs early on, even before his teen years. By high school he was a regular user of ecstasy and cocaine. Living on the street much of the time, Sheff became involved in various destructive behaviors such as selling drugs and working as a prostitute in order to support his addiction. Eventually, faced with the choice of jail or rehab, Sheff dropped out of college to seek treatment, at which time he was also diagnosed with bipolar disorder.