I've spent a fair amount of time in Midland and had companies from there on each side of my descriptions in mind. One of them might be the sneakiest big private company I've come across in my years of being an insurance puke. We started talking about their assets and insurance budget and I was gobsmaked as I looked around at an office that could have easily come out of the 1980's USSR. They owned and operated all kinds of highly profitable (but def not shiny) assets/companies, pretty sure it was worth well over $1bn. Just the nicest folks ever and probably worth god knows how many millions.
I guess I should clarify that the companies with the opulent office space I had in mind were all doing it with someone else's money. I don't know if the bourbon bar boys are splashing around their own money or PE money, but it seems like it's usually not their own when they do that and end up shitting the bed. When your E&P company's Inuit art collection is worth more than your E&P assets at liquidation, you've royally fucked up.
And I love Crested Butte. My boss has a place there and it's one of my favorite places on earth.