For many of the things he writes about, we can take his clout and background as evidence that his insight is 'real'.
But that's at most very weak evidence that his insight is real. Much of success is luck and networking, for example, and successful people are notoriously bad at disentangling various causes of their success properly, in favor of giving themselves more of the credit than warranted.
successful people are notoriously bad at disentangling various causes of their success properly, in favor of giving themselves more of the credit than warranted.
That's not clear to me. It is common to hear successful people saying things along the lines of "I wouldn't be here if it weren't for X, Y, and Z". In particular, I'm thinking of Linus Torvalds, whom I remember denying most of the credit for creating Linux. I'm sure there are many other examples. Overall, it's hard to tell weather successful people in general overestimate or underestimate how much credit they deserve.
This isn't really a full post, but merely a note of potential interest. Paul Graham (who runs Hacker News) has several very interesting and thought-provoking essays located on his personal website. To me they fit very well with the style of thinking employed and advocated by many people on LW and I'd advise that nearly anyone interested in LW check out his work.
I especially recommend Keep Your Identity Small, What You Can't Say, and What You'll Wish You'd Known, but nearly every essay up there is interesting to me in some way. Many of them are directly relevant to issues of rationality, while others are only indirectly related, but either way I found them worth my time.