He comes from old Peoria money, so likely inherited money from his grandparents. I think he was a savvy investor early on, so probably still has funds from that. He probably lives with his credit cards nearly maxed out, and maybe he does do a bit of very discreet escorting. All this in addition to whatever he's making from his "legit" hotel job. That's my hypothesis.
(It's fun to imagine him as a global ho-for-hire, earning most of his money that way, but I'm trying to give a real response.)
(It's fun to imagine him as a global ho-for-hire, earning most of his money that way, but I'm trying to give a real response.)