Remoak's list of highly successful people...
Donald Trump ""decided to declare himself bankrupt as it was financially advantageous to him"". I think he might've messed up a bit (too much money spent on toupes maybe?) and i'm not sure how many people lost money as a result...
And Disney was an Anti-Semite like you wouldn't believe.
I agree with your sentiments about taking risks and success being a function of educated guessing and risk management but the examples are a bit off-colour!!