I like it, but I just don't feel it too well when I think of the guild. Maybe after you finish with the back story completely, it will, but for now it just doesn't feel like a representation of Space Cowboys. I love the design though.
Well, I borrowed the design from the Rebel Alliance Privateers. You'll definitely get a better feel for it once the guild backstory is finally done.
"Rebel privateers were privateers hired by the Rebel Alliance to harass Imperial shippings during the Galactic Civil War. They were typically not formally members of the Rebellion, but nevertheless pro-Alliance."