Gaining wisdom by way of being paid massive amounts of money is an odd definition of "hard-won". Many people find out that their career is largely unsatisfying without stockpiling a safety net that could last a lifetime in the process.
It's one rung up the ladder from the guys who make their money in ethically grey ways, find religion, preach their conversion, but keep the money. (But it's still a rung up, mind you, and that's a good thing.)
Good for him that he earned so much, and that he seems to have found meaning in things besides money, but the story is pretty clichéd.
And I'm not sure "irresolvable emptiness" and an "unfillable hole" is quite so universal as you seem to indicate, nor do I think all attempts at filling voids are of equal value. (I'm not saying you do, either, just trying to be clear.)