Ben Saylor got his start in traditional dance music in 2006 when he began playing bass with the band Jubilee for contra dances and camps in and around Anchorage, Alaska. This exposure to Irish traditional music inspired him to pick up the mandolin, tenor banjo, and Irish flute, his main instrument ever since. He performed with Irish group Crooked Road before moving to the Bay Area in 2014, where he has frequented sessions and played with the Golden Gate Ceili band.