I don't know what it is about wine guys, but they're sexist as hell. (The moronic topic below about "self-respecting" men not drinking wine might have something to do with it. Wine guys care more about making sure other men think they're "real" men than they do about treating women decently.)
Vaynerchuk is probably a decent guy. He's devoted to his family (which now includes a daughter). However, like many men under 30 who are net savvy, he thinks the world is one big men's locker room. He and his commenters frequently compare wine to women and vice versa, and make jokes about cosmetic mutilation (i.e. implants) or rating women the way wines are rated.
What Vaynerchuk doesn't (yet) understand is that everything he says about women, he's saying about his daughter. When he describes a wine as a woman he wouldn't kick out of bed on Wednesday, but who isn't good enough to take out on Saturday, he's talking about his daughter.
Yes, Gary. Your daughter is the Wednesday night [deleted]. Remember that, when some guy a lot like you breaks her heart and convinces her she isn't "pretty" enough to treat like a human being.
The show's a study of the current crisis in masculinity. Even guys who think they're good "family men" harbor an intense, overwhelming, systemic hatred of women. Who knows when they'll start to cure themselves of it. In the meantime, I recommend any self-respecting women give these pathetic, clueless boys a miss.