What would you say is Donald's biggest business failure of all?

[tinrobot]

19. His biggest failure was not looking at himself in the mirror.

The man is obviously miserable and has been for decades. He has no ability to self-reflect and change himself for the better.

So, he looks outside himself for his fix - to money, power, sex, etc. He tries to push people down in a pathetic attempt to lift himself up. None of these work for long, and he goes to bed most nights hating himself. That's probably why he doesn't sleep.