Guru Gary Vaynerchuk Solves the Internet

The [social-media maestro]("/culture-trends/career-and-money/201001/internet-gurus-gary-vaynerchuk-dan-schawbel-laura-day-lewis-howes-seth-godin") on a Twitter war with Shaq, the iPad, and the perfect bottle of wine for under 20 bucks

Four years ago, Gary Vaynerchuk was a virtual unknown—that kid from Belarus who moved to Queens in 1978 and emphatically embraced capitalism, nimbly shifting from lemonade stands to a lucrative baseball card business to his dad's discount liquor store in Springfield, New Jersey. All that changed on February 21, 2006 when the energetic pitchman launched a video podcast called Wine Library TV. With his whimsically frank reviews—he's been known to compare certain vintages to Starburst candies and Big League chewing gum—Vaynerchuk quickly became a new media star, fielding interview offers from Late Night with Conan O'Brien, Ellen Degeneres, and Nightline. Today, at the age of 34, he's making yet another bold career move. As author of the best-selling Crush It!: Why Now Is the Time to Cash in on Your Passion, Vaynerchuk hopes to do for social media what he once did for Rioja. CEOs are lining up to hear what he has to say—shouldn't you?

Details: How does a kid from Belarus come to America and build a $60 million-a-year business selling wine?

Gary Vaynerchuk: Well, it has a lot to do with my parents. Sasha and Tamara Vaynerchuk—two classic Russian names—deserve a lot of credit. They not only instilled great DNA but also raised me in a great environment. More importantly, my dad started the business. So I walked into a business that was doing 3 million to 4 million dollars a year. It's not like I started from scratch.

Details: You seem to take a great deal of pride in the fact that you made your fortune in a family business as opposed to, say, a Proctor & Gamble or a General Motors. Why is that distinction so important?

Gary Vaynerchuk: You know, family is the single most important thing to me. I don't think that anyone loves corporations more than they love their family.

Details: But do you think it's made you more savvy in a way?

Gary Vaynerchuk: Yeah, I think that entrepreneurial spirit is always going to beat a PowerPoint presentation. You know that great saying: "He's got it" or "She's got it." That's not taught at Stanford. People who build family businesses are not classically trained. They have to deal with an enormous amount of politics. You think corporate politics are tough? Go work for your dad or your mom. The training you get in that type of environment is a good blueprint for success. I think a lot of corporations—now that we're moving more toward customer service—are going to have to implement more family-business tactics.

Details: Most guys think that the appeal of being the boss it that you get to call the shots. But you're all about the hustle. "What can I do for you?" Why is that?

Gary Vaynerchuk: Because I want to win bigger. Really. I'd love to say I'm Mother Teresa, but the fact of the matter is that I want to buy a billion-dollar sports franchise and the only way to do that is to make it about the employees and the customer. The second you turn on "It's about me" is the second you stop growing.

Details: In 2008, on the Late Show with Conan O'Brien, you compared a Pinot Noir to "the smell of a sheep's butt." I'm guessing you still have a few thousand cases of that wine stacked in the Wine Library storeroom.

Gary Vaynerchuk: Yeah, that might not have been the greatest call in my career. The thing that's most shocking to me is that America does not want to smell sheep's butt. I think it's a mistake, but, you know, there's only so much you can do.

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.

Details: What do you attribute that to?

Gary Vaynerchuk: I'm lucky, I guess. I don't know. It's weird, right? I mean I don't know. I don't know why I looked at people's computer habits in 2004 and said, "Well, this is different than their habits in 2003." But that's what I did. I said, "Holy crap, like, wait a minute." In my head, I had a mini-Nostradamus moment. I sit here now and I think about smart TVs and the iPad and I'm like, "My God, things are changing fast." I really chess play culture shifts. I'm really good at understanding what worldwide cell-phone use means. That's what I do. I try to picture it three to four to five steps ahead.

Details: So do you think the iPad is going to be a game changer?

Gary Vaynerchuk: I haven't wrapped my head totally around it. I'd like to touch it. I like touching things. It could be. I think people watching TV on it could be interesting. I want to see it, I want to see how big the screen is, how it looks, but I definitely think that it's got the potential to do some damage. I can picture people watching a Wine Library TV app in bed or at the table while tasting wine. It's definitely going to be a culture shift. But it really depends on how much usage it gets. CDs and phones were interesting because I knew everybody would have one. I don't know if everyone is going to have one of these.

Details: By your own admission, you were not exactly an A-plus student in school. So how did it feel to be invited to give the keynote at Harvard's Gravity Summit?

Gary Vaynerchuk: I loved calling my mom to say, "Mom, I'm going to Harvard." She got so excited. She's like, "My dream's come true." It's a very fun inside joke in my family. I respect education, I really do, but not in certain forms. It's not the brand that's been sold to our society. But I would be a liar and I hypocrite if I didn't say I was superexcited. It's always flattering to be associated with a brand of that magnitude.

Details: Do you think that the classroom setting is too rigid? Does it need to be reimagined?

Gary Vaynerchuk: I just think that kids like me could have been even better if we had an option to take business law and taxes and the history of commercials and advertising 101 when we were in fifth grade instead of being forced to follow what someone else thinks the curriculum should be.

Details: M.C. Hammer was also a featured speaker at Harvard. Does he now follow you on Twitter?

Gary Vaynerchuk: Oh yeah, M.C. and I text each other. He's very much an entrepreneur. I wouldn't say he's my best friend in the world, but we definitely communicate.

Details: Who would win in a Twitter showdown, you or Shaq?

Gary Vaynerchuk: What's the showdown?

Details: Who can drive the most traffic?

Gary Vaynerchuk: Shaq. Shaq's got more real fans than I do. That's just the way it is. He's had far more exposure and platform support than I have. On top of that, Shaq's got charisma. If he didn't have that, I'd be in much better shape.

Details: You say that your ultimate goal is to own the New York Jets. Are you sure you don't mean the Colts?

Gary Vaynerchuk: I'm very sure that I don't mean the Colts. I've got something for the Colts when I take over the Jets.

Details: Oh, really?

Gary Vaynerchuk: Yeah, losses!

Details: So that's still your ultimate goal—to own a sports franchise?

Gary Vaynerchuk: Not a sports franchise—the New York Jets franchise.

Details: Is it difficult to be a longsuffering fan?

Gary Vaynerchuk: Very! No question. I haven't missed a play since '82. Not a play. I was in Cincinnati, I was in San Diego, and Indianapolis. I'm all in.

Details: Last question. I've got $20 in my pocket. Which wine do I bring home tonight?

Gary Vaynerchuk: I would probably go with a Riesling from Austria. I think it's one of the single most underrated regions in the world and, for 20 bones, you can get serious Austrian Riesling from 2008.

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