"Staying foolish" is about having the courage to do things that look stupid to everybody else, because you have the belief to know you can make it work out.
Foolishness is the ability to ignore the "logic" that tells you things will be difficult, impossible, don't make sense in this market. It's not foolish as in complete stupidity, but it's that quality that gives you the determination to do what you want to do and ignore whatever stands in your way.
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