He is doing well for himself because he is damn good at what he does.
TBH, if you are good at any profession (plumbing/carpentry/programming, etc), you should be able to make a good living out of it, regardless of what your background is. Of course, you have to be able to show "something", to demonstrate that you are good; for gaming, this is where your portfolio comes in.
Here's a question: for those of you looking to work in games (coding/design) - have you not thought about working for yourself? Somebody suggested making small IPhone games/applications. To me, this seems like a no-brainer, especially if you are genuinely good.
There are obviously a lot of people who are craving to a get a games-related "job", when they may in fact find better success/money, if they try going it alone.
I can understand if you have no experience/confidence/ability at creating a game, but if you are genuinely good, then surely you should have a go at creating a product on your own and seeing if it sells?
I'm a great believer in the entrepreneurial spirit and everybody should at least try once, in their lives, to do something they feel passionately about, on their own. If it works...it could become massive (I believe that the owner of OCUK did this). If it fails, you put it down to experience and then get a "job", working for a company.