I wonder if the winning game becomes your own boss and tiny companies.

I want to do the jump, but lack of courage, good ideas, sales skills and a very good salary still holding me back (open for suggestions).
But if the very good salary would go away, the scales tip instantly.

That was always the "winning game". Only problem is that's a lot of work. The more things change, the more they stay the same; if you want more money, work harder. People who don't want to work harder complain that other people make more money because they either don't understand or are in denial about the amount of work the people they envy put in.

Yes there are exceptions. No pointing out exceptions won't help you, though it might make you temporarily feel better about yourself.