All his stuff are fluff pieces, it's like listening to a pitch coach. I have no idea why people see him as an authoritative figure in this space, when all he had was 1 failed start up.
What I do know is that listening stories directly from the founders is much more authoritative, informative and educational than listening to it from the investor's standpoint. Founders go through the stuff. Of course, investor's have their own stories which can be informative if they talk about specifics, not abstract things.
I just wish there was a way for people to share about their failed startups. Now, THAT would be truly educational. Majority of failed startups disappear without founders sharing their learnings and that knowledge is forever lost.
I think it's rather that the 'low hanging fruit' are all gone. The whole mood has changed. It's become harder. Notice for example that YC places a lot of importance on growth when evaluating applicants, I think in early stages you could've had practically zero users of your product and they would have considered you -- now, not so much.
Secondly, there hasn't been enough time to see what his track record really is, we'll need a few years to really see.
Now they do... YC is just an average investor now with more scale. The next gutsy call or intuition is simply not there with the current team.
HN is a news site and I enjoy it for that, but the community has been moved to a private network and the current YC team is more focused on looking good than doing anything innovative.
Also Flexport's good. Think they're under Altman?
What I mean by gutsy is having a view that is at least slightly contrarian and then executing on that view. There is nothing contrarian about making power law investments. That is standard for any large seed/angel/A series investor. The ones that don't do that don't make any money.