In all honesty, I believe for Gary it's all about the ego. The sheer number of shows per week, the endless request for attention in the form of the number of people he wants to post in response to his shows, etc. is certainly indicative to his need for attention and validation.
I believe his (his father's I suppose) business is truly very successful, and WLTV has provided the son an opportunity to show Dad that he can contribute, and be successful in his own right. A psychologist would probably have a field day...
He has the power over what to sell, and how much to sell, and I truly believe there is a certain sense of freedom and objectivity in his reviews (he doesn't owe a thing to anyone is probably his perspective).
That ALL said, I love the guy, and the show. It's quite addictive and I believe very unique. I get quite a bit of enjoyment out of the whole WLTV experience.
My wife and others I've exposed to the show all agree that his approach is very entertaining and puts an anti-snob spin on our favourite subject.
Let's face it - We all take this subject way too seriously considering our lives are not dependent upon it. It's just a hobby for most of us on this board.
Gary goes out of his way to stress that you should not take his word for it (and I don't), and that the only so-called critic you should listen to are those that have an alignment with your palate. For the most part, my palate has nothing in common with James Laube, however have found my 'scores' to line up quite close to James Molesworth. Hence, I tend to pay more attention.
With regards to Parker, I tend to shave at least 3-5 points off his scores, and generally that is where I will land with my own preferences.
To conclude, I personally put my 'trust' level at an equal level when it comes to both Parker and Vaynerchuk. But that's just me.