There's a Ask HN thread, maybe a few, of people who hit it rich and later lost it. The common theme is it's easier to make lots of money than it is to keep it, which is a little unintuitive.
Is it really unintuitive? Most Americans only save about 7% of their income IIRC, wouldn't it make sense that they would mismanage most windfalls by default? In recessions, this number jumps up dramatically, proving that it's mismanagement that contributes.
I don't believe anyone gets a windfall by saving 7% of every paycheck either. Those who ran a startup make it a habit of burning through millions a month too. What's really unintuitive for me was seeing that CFAs are terrible at personal money management.
1. Bad budgeting or lack of diversification. "95% of my money was in Enron"
2. Confirmation Bias. "I build a successful company once, I can do it again, but this time with my own money"
3. Hedonic Treadmill. "Flying commercial is so annoying, I'm going to fly private, and figure out how to pay for it later"