I feel GaryV is slowly going the route of Tony Robbins.
I see what you're saying. I think he likes the attention gained by giving the motivational talks, but I don't think he's necessarily attempting to turn into Tony Robbins.
I feel that instead, what he is doing is simply a tactic to grow his marketing business. As I said earlier, he's probably using it to sell his clothes, shoes, merch, seminars, etc. in addition to getting a lot of qualified applicants to his openings. But this is also small potatoes. I don't think he even cares about this stuff all that much either.
Instead, I feel like the final
goal of his is simply growing his social media to get more contracts for his VaynerMedia business. The entire GaryVee persona for all we know may be fake. I remember hearing a random throwaway comment years ago from an Andy Frisella podcast talking about GV and he said something to the extent of "Gary is way smarter than any of you listening to this podcast and you don't get what he's doing" and that is when I realized that his whole reasoning for his push on social media was to be able to point to his social media profiles when pitching clients to show he can get results.
He doesn't give a damn about how much money he makes from his K-Swiss sneaker deal. It's nothing to him in the grand scheme of things.
But if he's pitching a client and going against a titan of industry like BBDO, BBDO will say "We are the best ad agency/marketing firm ever. Look at the clients we have!" GaryVee will then say, "I literally had to send one tweet and now millions of people think K-Swiss is cool again."
Since Gary doesn't have size on his side when pitching clients, he can only go on results. Since he knew social media was untapped at the time he decided to grow his social media so that he could easily prove to clients he was legitimate. Now he not only has a large follower count across social networks, but his followers are extremely loyal and highly interactive when it comes to commenting/liking/retweeting/etc.
This is obviously all speculation coming from my own thinking, but I think he's simply using his following on social to have legitimacy when giving presentations and making deals.