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.