There has been a lot of research gone into what makes someone financially successful and the current line of thinking seems to be that soft-skills, like stick-to-itiveness, are the primary factors. Someone who matches the description of your acquaintance doesn't exactly remind me of someone who is has a predisposition for success. Perhaps that has been his failing in the job marketplace and not the lack of a degree at all?

Then again, I always feel like I don't know enough, though I know far more than a lot of my peers... It just depends. I tried running my own business for a while, and failed. I also worked at a director level for a while, didn't like the stress. It really depends on what you are looking for.