My boss used to drive me home from work at times, and I still remember one of the things he said. "The more money you make, the more you spend. Spending on material things is like a gas that fills every available space unless controlled."
That really illuminated things for me, and explained why he refused to spend in order to buy a better car. What you mentioned about not being afraid to fail is also what I saw over and over again.
In fact, they viewed people who hadn't failed enough, as not being as seasoned, and worth partnering with, as those who did.
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