If you risk your capital and jump into a business, there is 80% chance you will not succeed. When Trump went bankrupt, he did not go sit in a corner whimpering and go on welfare. He figured out other money making venture and today his net worth is $2250 Millions. That is what I call a can do person. He is not a quitter.
Again, once or twice, those are bad breaks.
4 times tells me that there is fundamentally something wrong with his “decision making process”, and I don’t make excuses for repeated failures when I observe many other executives who manage their organizations and fortunes without having to use the so called “last resort”, particularly several times.