Ryan is a fifth-generation violinist who has been playing since he could walk. He played with a group of children assembled by his father, called the Pee Wee Pickers. He played with bands throughout high school and college. He began forming bands, but hated it when musicians dropped out. He formed the RubberBand with the idea of drawing from a pool of musicians who could wander in and out. However, certain members seemed to stick, and the band soon became a cohesive unit. Most of the members had known each other from the area circuit before they joined Shupe in the RubberBand.