My personal epiphany came about 10 years ago. I was in an incubator in SF, and some investor came to give a talk about fundraising. They heavily emphasized that many startups do a friends-and-family round to bridge them to a proper seed round-- nothing major, just get 20k from 5 family members and you should be good until you have something to show angel investors. My two co-founders and I (all from the Midwest) realized that we couldn't even come up with five people to ask for 20k because all of us came from pretty modest families.
These are the types of privileges that get glossed over in success stories. To be successful you, more likely than not, need to either have money or have connections to money. Everyone likes a good underdog story, but those founders are more like lottery winners than anything else.
So, coming from that lens, it's hard to take advice seriously from "successful" entrepreneurs. It's sort of our industry's equivalent of "just stop eating avocado toast and you'll become a millionaire."
I wasn't arguing anything about any particular person, but rather commenting that a lot of the entrepreneurs and investors that get fetishized around here found their "success" from family wealth or by doing some sociopath-level things. There are obviously exceptions, and maybe Naval is one of them, but I've read enough Silicon Valley biographies to become pretty skeptical of this entire genre of business/self-help/productivity hack books/blogs/tweets.
That's a "privilege" he earned.