I've commented many times before how I've become a bit disillusioned with pg's writing over the past decade or so, because it always seemed to lack anything beyond a surface level of introspection. He always seemed to be pushing the idea that qualities that make a person great at startups are the most important thing in the world - not surprising given his industry, but to me many of his essays just felt more and more self-serving, while never commenting on (or, in my opinion, really even understanding) the real societal negatives that I think have been a consequence (admittedly unexpected) of the startup boom.
But, in pg's defense, when it comes to his writing style and the quality of his prose, I think he's generally top notch, and even though I may disagree with him more often now, I appreciate the structure and clarity of his writing. Given how influential his essays have been, I think he's qualified to write about how his communication style makes an impact.