The main point of this discussion seems to be the old "don't concern yourself with material things"-spiel. And I agree with the general idea. I also agree that to succeed, you can't just follow rules of thumb blindly, you need to understand your field of work.

I don't really take issue with the content, but there's not much of it and he's not very efficient at communicating it.

Examples: When trying to say "don't let the means become an end" he uses the 5-dollar word "intermediary", which typically means a person, instead of the simple "means". He says "my speech is fraught with peril" instead of "If you don't listen carefully you might misunderstand". He says "the solution isn't the solution, the problem is the solution" instead of "There is no arbitrary solution that's applicable to all problems".

He's really just paraphrasing common aphorisms with bigger words or wrapping them in koan-like phrasing. I think that's why he sounds appealing. He's telling us what we already know, but in grandiose terms.