Amen to this. Gary Vaynerchuk is one of the most loathsome personalities to ever emerge from the early 2000's internet fame machine. His message is poisonous, and has been the excuse for creating dozens of worthless me-too startups that hurt communities and destroy the credibility of legitimate startups with real ideas. I like DHH more than I already do for going on record as being against this hustle nonsense.
Did you even read the first sentence of the post?
I love Gary Vaynerchuk dearly. So much of his message about patience and perseverance is completely in line with how I view the world.
I can't watch Gary V or any of that kind of stuff, and I also think some of his message has led to useless me-too efforts, but I wouldn't go so far as say "one of the most loathsome personalities".
At some point after a certain amount of money and fame, if all that is still not "enough" and you need to insist on hustling more and advocating to anyone who will listen that they should also burn the midnight oil every night indefinitely to "hustle" also, then it's no longer a business strategy, it's just escapism. It may be good for Gary and his acolytes, but from the outside it's a brittle, overly shrewd, soul-sucking way to experience life. The fact Gary is always bragging about not reading books is a pretty good indicator.
Every time I stumble upon something with Gary he is always hustling and surrounded by people, but he always seems to be so lonely.
Some people just don't mind it. I certainly would, but it's just not a priority for some I know... But maybe you're right and he's empty inside. Not for us to know.