He has an unfortunate tendency to see the way that he was successful as the only way to be successful, and seems to lack the ability to benefits in other ways of doing things. We used to see this in PG's writings too: back before he started YC he appeared to be utterly convinced that it was Lisp that made his company successful. After he started YC and he saw a lot more his writing became a lot stronger IMO.
Regarding DHH, I'll just point at [1], with the comment that Facebook made $891 profit last quarter. It's also currently valued at ~$300B.
[1] https://signalvnoise.com/posts/2585-facebook-is-not-worth-33...
To be fair that blog post was written in 2010 when Facebook was still a private company and had nowhere near the level of advertising, reach, etc. that it has today. In particular they had barely scratched the surface of mobile and were only making money off Farmville and other ephemeral apps.
The trajectory was clear enough that all those investors DHH called "star struck" put money in.
To quote him: Irrational investor exuberance indeed. I think it would be more sensible to class them as "investors who had more foresight than DHH".
He berated them for being dumb. Since we can now see that they weren't dumb at all we should consider DHH's insights questionable.
They were desperately buying anything they could on the secondary markets. That isn't luck, it's seeing an opportunity.
It's like Pinterest 2 or 3 years ago (say around the time of the 27M A16Z B round). Putting as much money into that as you could isn't being lucky, it's seeing an opportunity. Their 2014 and 2015 rounds are basically just ways to print money.
That's the whole crux of why people don't respect VC.
Um. Some people don't respect some VCs. I don't agree with everything Marc Andreessen says, but I'd be pretty silly if I didn't respect his opinion on technology.