[gitfan86]

The scenarios where that can happen:

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"