Details: To be fair, you've made a career of calling things like you see them or taste them, right? Rather than using the effete terms that other wine connoisseurs do?
Gary Vaynerchuk: Instead of saying, yeah, the status quo is fine, or this guy or this girl is the CEO of this company so they must know more—I just don't believe that. It's not that I think that I know more. I'm pretty good at sticking to what I know. You don't see me social commentating on health-care or presidential debates. I talk about what I know because I'm petrified of being wrong. I'm really good at living it first and then talking about it. I'm not a social-media expert because I read other people's books. I did it first and built a business around it and then talked about it.

Details: So now, with Crush It!: Why NOW Is the Time to Cash In on Your Passion and VaynerMedia, you've positioned yourself—and very successfully I might add—as an online-marketing consultant. Instead of selling wine, you're selling Jalen Rosen. Is that a step up for you?
Gary Vaynerchuk: I love Jalen. You know? I don't know if it's a step up or down. It's a scratch I needed to itch. That's how I look at it. It was the only thing I could have done, because I really wanted to see if my storytelling and my marketing talents could translate to other things. That was very important to me.

Details: In this new role, you get paid to tell people what you think. You pitch your ideas to celebs and CEOs in places like the South by Southwest Festival. Sounds to me like the coolest job in the world.
Gary Vaynerchuk: I definitely don't have it bad. I definitely would not switch. It's really flattering, if nothing else. I don't feel intimidated—I definitely feel like I have the chops—but it's nothing short of flattery to have people you respect respect you back.

Details: In a way, your interest in wine was perfectly timed. It hit just as the country's interest in wine was exploding. With this new job—as an expert in social media—are you in the right place at the right time once again?
Gary Vaynerchuk: You're a good dude for asking me that question. One of the things that I'm really proud of is that I have really good timing. It's very easy for me to see what's coming up and it's no coincidence that I went headfirst into wine and then headfirst into new media—none at all.