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.