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None of his achievements as an entrepreneur give him insights into philosophy, political economy or anything else he writes on.You don't get insights into these by getting a degree from some university on the subject. You get insights into those things by studying them, practical experience, and more importantly thinking.
If anything, the most clueless people in those areas I know are tenured professors.
And REAL thinkers, the kind that leave a mark in history, from Socrates to Sartre and from Kierkegaard to Popper and Wittgenstein to leave it to philosophy, are full of scorn for academia in general and professors in particular, and even if they sometimes happen to be working as such themselves, they are greatly atypical to their "churn papers" colleagues.
Not that pg is on that level, but critisizing him because "none of his achievements as an entrepreneur give him insights into philosophy, political economy or anything else he writes on" is bullshit.
Your a priori abstract attack that he lacks insights has no meat at all behind it. You could just as well have said that "he has tons of insight into what he writes" -- and it would be exactly the same.
If you want to provide something worthwhile, do a SPECIFIC critique of what he wrote somewhere, and tell us what is wrong with it by providing counter-arguments and rebuttals.