Also, these days if you are a smart ambitious person looking to make an impact with technology you're not terribly edgy and you certainly aren't defying any major social norms. And that's a good thing.
In 9th grade insists "I don't see the point of these classes I'm going to be a programmer," takes AP comp sci as sophmore finds it insultingly easy [gets in trouble for going ahead of teacher], resents homework vocally and refuses to do it on principle but still gets great scores on tests, places in the school math competition but initially gets kicked out of the award ceremony for refusing for the "National Honor Society" performance, 12-grade gets official permission to work half-time coding and only take half classes.
That's what I was, and I don't think anybody else has ever given me a word for it. I knew pedantic nerds, and intense nerds, and condescending nerds, but few with real conviction.
Could the terminology just be in flux, and therefore create confusion? With woke et al., we've got pleeeeeenty of examples of smart folks who miss the social norm du jour, attempt to say something true but rather say something unacceptable. And then they get ostracized or fired.
Maybe these folks are some examples of what used to be called nerds. Do we have a name for them?
That's the case for all PG essays, isn't it?
The vast majority I would say that he is trying to retcon his huge success and the success of some businesses he has been associated with into a coherent worldview. I believe that in 'Hackers and Painters' he actually goes through some back-of-envelope calculations that show that the money he made when Yahoo bought Viaweb corresponded closely to the real value he had created, in some sense.
It is baffling to me why he isn't able to say "I got lucky - I worked hard and created something very valuable, but I was also in the right place at the right time." Clearly there were special factors at play selling an e-commerce platform to Yahoo in 1998. He's also done intelligent and pro-social things with both his money and his time since then it appears. I don't know what the shame is in saying "I won a lottery - but I have tried to do the right thing with my good fortune."
I think if you asked Jamie Zawinski, who I think was no less technically skilled, nor less purposeful about working on interesting and important things (nor, tbh, any worse at writing thoughtful essays), he would readily admit to having been extremely lucky. I don't know what the difference is between these two personalities. I think I'd rather be jwz in similar circumstances.