I don't suppose you have ever sat at a craps table in Vegas with a couple of hundred thousand dollars on the 'pass' line?
One of the weird things that happened to me when I was living in Las Vegas as a young man was that it really warped my sense of 'money'. People would roll into Vegas, lose a few hundred thousand and drive out with a 'see you next year' attitude. People would walk into a casino with a couple of hundred dollars and walk out with several thousand. Basically "money you had" was completely disassociated from "your work product" because if you won or lost was just random chance. So there was no confusion about having "worked" for this money, or "scrimped and saved" this money, it was just "Oh look, here is a bag of money where no money was before."
If you were living off a modest to low burn rate (like practically nothing) then you knew you could 'lose it all' and not a whole lot would change in your life. So betting everything you had on the next roll of the dice wasn't crazy, it was fun, either you'd keep playing or your fun was over for the night.
A number of people in the early days of the dot.com explosion were stunned at how 'easy' it was to 'make' a ton of money. There was even a cartoon about it where the CEO of some startup says "And the police never show up?" and the VC/Investor is saying "That's the beauty of it, its all totally legit!" When you're in that mode, and you've made your first few million, I could see thinking "Doesn't matter if I lose it all, I'll just make more. It's not that hard." When the music stopped if you were currently 'up' by a large margin you did a double take perhaps.
Having known people who are that agnostic to 'money', it just doesn't mean that much to them, it doesn't present like sociopathic behavior. The sociopaths I've known have always had some sort of 'score' system running as a way of evaluating whether or not they were 'winning' and money is a very attractive scoring system.