This, like most of his writing these days, seems to me like post hoc justification and defensiveness for his personal financial success. It's difficult to uphold a sense of worthy accomplishment when you are increasingly confronted with the inequity and unfairness of the system in which you 'won.' The "7 of the 8 richest people in America" that he is lauding are all notoriously awful people to those around them. I would hate to have to work with a self-described "fierce nerd" at any level. I wish we would do more to promote and reward kindness amongst nerds and non-nerds alike.
How do you avoid this fate? Work on ambitious projects. If you succeed, it will bring you a kind of satisfaction that neutralizes bitterness. But you don't need to have succeeded to feel this; merely working on hard projects gives most fierce nerds some feeling of satisfaction. And those it doesn't, it at least keeps busy.The bad news is that if it's not exercised, your fierceness will turn to bitterness, and you will become an intellectual playground bully: the grumpy sysadmin, the forum troll, the hater, the shooter down of new ideas.