The original manager of Stillwater, Dick Roswell has been a part of the Stillwater family from early on. He's a little rough around the edges, but he's fiercely protective of the band. We learn that Dick was brought in by Russell to manage the band because of their friendship. Unlike Hope, it's clear that Dick really cares about the band and everyone in it.
That doesn't mean he can't be a little scummy at times. He is the one who initiates the sale of Penny and the other Band Aids to Humble Pie—for $50 and a case of beer. Later, aboard the airplane, Dick divulges a secret to the band. "I just want you to know," he confesses, "if I took an extra dollar or two here and there… it's because I knew I'd earned it!" But Russell, Jeff, and Larry all share that they had been sleeping with Dick's former lover, anyway, so maybe it evens out?