Part of why I'm sure is that I was prone to thinking like this as a teen. I was a smart kid from a family that valued smartness trying to get by in a world that generally didn't, and certainly didn't value the kid of weirdness that in retrospect made me well suited for what turned out to be hot career.
I made it to an environment better suited to me (SF, tech industry) and eventually got the fuck over myself. I used my newfound material and emotional safety to do the necessary work of self-examination that let me get a better handle on my self-justifying bullshit. To spot and manage my desire to be right, to be smart, to be without intellectual flaw. To write bombastic essay like this.
So yes, I think you have part of it. It is hypocritical. It doesn't model what it's talking about. But for me it's worse than that. One, it presenting an at-best-incomplete approach as the final word from on high, it's going to create a sad sort of blinded conformism of its own. Doing a tech startup has long become a cargo cult of its own, and this won't help.
Second, in his amateur psychologizing, I think he makes some elementary mistakes. E.g., valorizing the performative anti-caring about what people think. To me that's a sign of insecurity and/or a trauma reaction to some past person who was overbearing. For me, true independent thinking comes from listening to others without judgment and choosing for myself. Positive attachment and negative attachment are both attachment.
Third, this reads to me like it's a part of the political kick he's been on in recent years, where he's shitting on the US left. E.g., the footnote about how politics is boring because it's subject to intellectual fashion. He complains here about people who "think themselves nonconformists, but actually they're niche conformists". When honestly his opinions, which I once found fresh and interesting, seem to be the tiresome conventional wisdom in his niche, and easily predicted by his financial interests and social position.
I get that he's gone through a hard change. He used to be an underdog and would still like to see himself that way. But in reality, he's rich and powerful, a kingmaker in what has been the hottest segment of American industry for a generation. One that in my opinion has been vastly overfunded for the last decade or so. That is a challenge to anybody's self image. You can't be a genius underdog and at the top of the status quo. But given his money and his smarts, he's not doing a good job at all of meeting that challenge.