I have found a few of his essays very good, indeed expressing things I haven't seen anywhere else. I think he has provided very good advice to young people at times.

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.