I think more accurately, it means you either have enough wealth that you don't have to work to maintain your lifestyle, or your income is high enough to support

I think more accurately, it means you either have enough wealth that you don't have to work to maintain your lifestyle, or your income is high enough to support extravagance without going deep into debt. Bezos doesn't have to work. To be honest, I don't know why he still does. Personally, if the stock options at the startup I work with end up panning out to be worth $5M or more if/when they go public in a few years, I'm taking that cash and retiring at 45. Throwing it into an S&P500 index, I could live off the interest for the rest of my life.