Then would you also agree that a dollar wasted is a dollar wasted whether you have ten, or ten million?

No, I think money is different from time this way. For example, it's possible to have more money than you know what to do with, but having more time than you know what to do with is a rarer problem. My marginal utility for money is really high for my first few thousand dollars and then drops off. My marginal utility for time is shaped much differently... I would value 20 extra years of youthful happy life about twice as much as 10 extra years of youthful happy life. People are (rationally) risk-averse when they have small amounts of capital because their utility function for money is such that they would really like to have at least a small amount. I don't see any corresponding effect for time (indeed, people say things like "it's better to burn out than fade away").

Bankruptcy is the loss of 100% of your assets.

Personal bankruptcy, yes. So young people starting businesses would run a higher risk of personal bankruptcy and the drop in credit rating that implies.