Classically trained in violin and viola, Freiberg began his career moonlighting as a coffeehouse singer-songwriter (playing acoustic guitar) during the American folk music revival while working for a railroad. For a while, he shared a house in Venice, California with David Crosby and Paul Kantner before being briefly jailed for marijuana possession. Prior to being incarcerated, he also became acquainted with Dino Valenti, then Crosby\'s nominal roommate on a houseboat in Sausalito, California. During his time as a coffee house folk singer, he was part of the duo David Michaela. David & Michaela made a demo at CBS studios, and "Elektra producer Paul Rothchild proposed fitting them into a bigger folk group. But the onset of the Beatles spelled the end of David & Michaela, and incentive for Freiberg to switch to rock and electric instruments."\n', '

Following his release, Freiberg co-founded Quicksilver Messenger Service with guitarists John Cipollina, Jim Murray and Gary Duncan and drummer Greg Elmore. The founding took place shortly after Valenti, who had recently hired the musicians for his backing band following the folk rock explosion, was imprisoned for drugs in 1965. Due to the surfeit of guitarists in the group, Freiberg (who was only tangentially acquainted with his bandmates through their mutual friendship with Valenti, with Cippolina remarking that they had been instructed to "take care" of him) was assigned the bass.\n', '

Founding the band in 1965, he became the "most folk-rooted member" of Quicksilver. He played guitar and keyboards, and reworked a number of songs for the band. He also shared lead vocals with guitarist Gary Duncan and played bass. \n', '

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