Loudon's sister (and Rufus's aunt) is one fine songwriter herself. She runs her own label, Derby Disc Music, and recently hired an assistant. She has previous business experience, which helps with making day-to-day decisions.
"I'm an entrepreneur," Wainwright says. "I once owned a restaurant, The Baker's Cafe, which was great business training. Being in charge, paradoxically, means I also rely on experts. I don't know everything. So, I get help from people regarding itineraries, contracts. My assistant? He does my office and social media stuff. I make the decisions about recording and gigging. But a good boss should be willing to collaborate with someone who knows more."
Wainwright also knows when to outsource.
"I recently signed with a PR firm, who'll help with the re-release of a record. I make decisions about how to spend money. Most importantly, you have to remember this is a job. Work on it every day. You'll definitely see results."
NEXT: Marshall Crenshaw