I don't really think this is a new theme for pg's essays [edit: I mean, I don't think pg's style or content has changed that much], although I've also noticed this change [in responses here].
Usually, HN is the space where his essays are most heavily defended.
I am not sure where the bitterness comes, and to be honest, I would like to know. We are reading the same essays.
More and more I am starting to think that people who are decrying pg's writing should come clean and say whether or not they've started a business, and if so, what was the outcome. The outcome isn't as relevant, but I bet there are very few people out there who have reached, lets call it "Fuck You" money through running their own business who would read this essay and go "Hah he's so out of touch he doesn't even see it anymore" and toss some link about Dunning-Kruger or whatever.
For people who are in the business of making money through getting shit built, I think what he's saying will resonate just fine. But then again it's one of those things where the people who need it the most are the least likely ones to take it, and vice versa. It's akin to the "It's a good problem to have" crowd when you say how you're sick of dealing with clients on the phone even though you have a 200-person company, and they look at you sideways because they have no idea why you are complaining.
He's talking about billionaires and interviews in this one, and he starts off saying how the two threads are connected. But what he's really talking about is building-a-business-by-convincing-people-you're-not-full-of-hot-air.
And unfortunately, when I see people tearing his essays apart, their ramblings strike me as nothing but hot air.
I think it's HN who is out of touch more than pg is, because I don't think the vast majority are here to build businesses whatsoever.
"He's talking about billionaires but he's REALLY talking about something else that people in the right audience will get, and just filter out the noise" sounds fairly out of touch, if he can't see that the framing he's using is needlessly complicating the issue. Or if he wants to connect to a larger political discussion about global economic systems but only has substance to discuss related to a narrower "building a business" question.
Would be easier to just talk about what he's actually talking about, then.
To be fair this is another article/essay in a very, very long string of his that can be filed under some kind of a "Fundamentals of Business" type category. If you talk to owners, they will inevitably say the same things he's saying, sometimes verbatim. But these owners wouldn't speak in direct words either, because "speaking to customers/users" is too context dependent to get into in an HN comment. There's too much nuance to bash the person over the head with it when writing this sort of an essay.
That's mostly what tipped me off to not take his words at face value but to interpret them through his lens as a VC and someone who is trying to communicate business ideas (ideals?) to people who, I would at least hope, aspire to create a business of their own. Whether it's a million or a billion, it doesn't matter. Nearly everything he talks about applies to "lifestyle businesses," which is I think partly why YC offers some small bit of money to get the ball rolling rather than go gung-ho and throw massive amounts of money at people. I don't know if this has changed, I don't think it has. Obviously it doesn't hurt to get a leg-up from the counsellors and whatnot that YC provides through their alumni program.
I am not sure if he's spoken about it but I wouldn't doubt that one of his philosophies is that a diverse number of businesses can grow to a reasonable revenue (where the founders are happy and working away at it) with a bit of money to start with, and that way YC doesn't have to spend a fortune early on and everyone walks away happy even if YC doesn't turn a sizable profit. Some kind of a threshold where YC feels anything above that means they're pissing money in the wind and their ROI isn't any better, but at the same time they're helping the founders as best as they can.
So you have to take the times he talks about being Ramen Profitable and talks about building a Billion Dollar Business and find the underlying threads tying it all together.
pg can't tell you exactly what, how, when, where, why you should be doing the thing you need to be doing to build a business. His words sound like platitudes most of the time to me personally, which is why I take the side of "the people who need this the most won't take it, and vice versa", because the person who started a business and is profitable didn't have anyone like pg telling them this sort of stuff. Would someone read his words before starting anything and be inspired to? Perhaps, but it's a long journey and counting on such flimsy motivation to keep you going is to me silly.
For some, certain things might be common sense. For others, not so much. Plenty of founders, even those with serious business experience, still have it ingrained in them that "if you build it, they will come", and they neglect every other aspect of business. Yes, I'm talking primarily about engineering types. This essay is to remind you to focus on the users, and the rest will follow.
Aside: I'm grateful for the Startup School library. I think it's a great resource. It's got a nice mix of obvious and non-obvious advice in there. When people disparage pg's writing, they should take a moment and see what his company has built for people who wish to create a business before declaring him out of touch.
I've started a business, we were recently acquired for a nine figure sum, and I think PG is increasingly out of touch. My best guess is that he's been rich too long, but I feel the bitterness and have been quite successful in my tech career starting companies.
Usually, HN is the space where his essays are most heavily defended.