Bridwell was born on April 25, 1978 and grew up in Irmo, South Carolina. He left home at age 16 and moved to Tucson, Arizona to live with his mother.
While living in Tucson, Bridwell worked with Mat Brooke and Jenn Champion, selling pizza. In 1997 the three moved to Olympia, Washington, but soon relocated to Seattle, where all three worked in a bar. Bridwell founded a record label, Brown Records, while Brooke and Champion formed the band Carissa's Wierd. Bridwell later received some basic drumming tuition from Brooke and subsequently replaced Carissa's Wierd drummer Robin Peringer, who left to play guitar on tour with Modest Mouse. Bridwell later moved on to bass guitar.
Brown Records released the first two Carissa's Wierd albums, but Bridwell eventually gave up running the label and Carissa's Wierd released their third album on Sad Robot records, before splitting up in 2003. The band reformed for a few shows in 2010 and 2011, but Bridwell took no part in that reunion.

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