It's the gospel of someone who experienced, by common standards, extreme success. No more, no less. I find his essays mostly to be opinion pieces without exceptional insights or conclusions that would make them stand out if they were not attached to his persona.
I still enjoy reading some of his stuff, but over the years I've realized that most of his writing lacks any rigor or evidence for what he says. He'd be a much better writer if it weren't for the way people read his good and usually thoughtful writing and take it for truth. This happens as you say due to him being successful, which I find kind of pernicious. I've found some of his stuff in hindsight simply wrong, but he'll never go back and correct it, nor will people listen to criticism.
My only wish was he was more cognizant of this and wrote accordingly, but his writing has gotten less rigorous and more flowery over the years, not less. It's a real problem across tech. I've read some comments on HN describing tech as devoid of culture, which has some truth to it, but the bigger issue is we don't really care about evidence, and that comes from the top.
I've actually noticed that too. I remember reading his articles from the early days of HN and being enamored by their insights... mad respect. But then he tweeted something along the lines of "There's no Uber or Lyft here in Austin, Texas. How do I get anywhere?!" (Uber and Lyft had left Austin at the time) which fundamentally changed my view of the guy.
I think his, and Spolsky's, writings are fine, and actually have some insights, but often have a lot of cruft around them. It's kinda like the internet condensed ;)
