I've read this before. It's fascinating that people should be set for life and in less than a decade its all gone and they end up worse than they were before.
There was a show called how I won my millions that looked at the lives of lottery winners and what they did with the money. Watching them live It was odd how almost all of them had no sense of self worth or value, and it began to make sense why they went broke.
It's funny. I grew up lower middle class and my wife grew up solidly middle class. We live in NYC, have a pretty nice lifestyle and last year I reached what I considered an income milestone. In the 7 years we've been married, we've stuck to a pretty reasonable budget. We didn't live like paupers, we vacationed, ate out regularly, had a part-time nanny, all the typical young family in NYC stuff. But we always kept a close eye on how much was going out and how much was being saved and invested.
After I reached that certain income level, we talked about our budgeting and were like "over the course of our marriage, we've obviously been very responsible with money. There's no reason to have a set budget any longer. We'll be a little less watchful of what's going out, but we just won't deviate too much from what we've already been doing... so we'll obviously end up ahead." Just by getting out of that mindset, it was amazing how much more money we were spending. We were never in danger of going broke or anything, but there was a six month stretch where we were regularly missing our monthly targets by about $1000. It wasn't just like completely crazy spending, either. It was just stuff like "let's try the gourmet version of this product. It's only $9 more and 2 isn't really a big deal." Or "Remember that thing we couldn't find after looking for it for two minutes? Let's just get this replacement that looks slightly nicer" or "I don't really feel like going all the way to the upper east side to save $40 on a bookshelf." Little things that are mostly reasonable on occasion, but doing it every day or every other day sneaks up on you.
I know most of these ballers going broke are being much more extravagant than that, but I also think the psychology of how we'd relate to money if we had a different amount is not necessarily an apples-for-apples thing.