Q&A: Internet Wine Guru Gary Vaynerchuk

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Erik Kastner

Wine expert Gary Vaynerchuk, founder of Winelibrary.tv and author of Crush It! Why Now Is the Time to Cash In on Your Passion

Gary Vaynerchuk is an Internet phenomenon. Trusty New York Jets spit bucket by his side, he's helped grow his family's liquor store into a $70 million online wine retailer and made his daily wine-tasting videos — at Winelibrary.tv — a staple for thousands of viewers. Gary himself boasts more than 850,000 followers on Twitter. Now, he's sharing the secrets of his success with the masses in his new book, Crush It! Why Now Is the Time to Cash In on Your Passion. Vaynerchuk talked to TIME about the book, the growth of his online brand and his game plan for world domination — or at least eventual ownership of his beloved Jets.

Let's start with your book. You mention that all along you were never selling wine as much as you were selling yourself on the show you created.
Sure. Winelibrary.tv was about building personal brand equity. It was a business move. Now, it was totally surrounded by a passion for wine, but I very much gave a lot of thought to doing a sports-video blog instead. It was just about building personal brand equity, realizing that the platforms of getting to the consumer had changed, and wanting to be an early adopter of that opportunity.

At what point did you make that realization? Was there a moment when you said, "The Internet is going to be huge and I want to be a part of it"?
It was in 2005. I was walking by and my two lead developers were sitting in their office laughing their butts off at Ze Frank. And I was like, "What is this? Video shows on the Internet?" I was like, This is it. This is going to replace television.

You didn't do any sort of formal training in wine appreciation. Did you sort of teach yourself?
I had a big advantage. I grew up in it. The chef that grew up with the grandma who cooks tends to always beat the chef that went to the culinary institute. It's in the blood. No. 2, as people have gotten to know me and my intensity and my hustle, it's become very obvious why I was successful. Because this was the only thing I focused on. Every day, 18 hours a day.

You went on Conan O'Brien's show and you had him tasting asparagus and sweaty socks to demonstrate the different tastes of wine; you went on Ellen and you were licking rocks. Was this actually stuff you did yourself?
Yeah. When I was 17 or 18 I wanted to become a wine expert, and my parents wouldn't let me drink. So I was devastated. All I could do was read, and I read and I read. And I'd read something like, you know, "Subtle hints of cassis." And I'd be like, "What the f--- is cassis?" And so I went to Kings Super Market in Short Hills, and I was like oh, cassis. And so I started tasting those things. I'd go everywhere up to about cat pee, which is a tasting note that a lot of the sauvignon blancs have. I didn't really want to go there. But I was pretty much everywhere else.

If someone came to you and said, "How do I develop my wine palate?" Do you say, "Here's a sock?"
I'd say, go to Whole Foods and Wegmans and taste every fruit you've never had before. How are you going to pick up the nuances of pomegranate if you've never had it? The other thing is, try a different varietal of wine every day for 365 days. Never order chardonnay from California twice.

Do you think Americans are getting more diversity of tastes when it comes to wine?
Yes. I hope at some level it's a little bit of my show, but mainly I think it's the Internet itself. Wine critics like Robert Parker say, "Drink big cabernets!" But they are not the only voices. People are more comfortable learning about wine because now they can just Google, you know, Soave, and say, "Oh, O.K., cool."

Let's talk about your online popularity. You have, like, 850,000 followers on Twitter.
This always makes me laugh. When I meet real celebrities who kind of know me, they can't wrap their heads around that.

How do you get to that?
I care more than they do.

About everything? Or about Twitter?
About people. I'm sure plenty of them care too, but I just really care, which has always made me insanely good at customer service. I was that guy. In social media, there's no filter. When you say, "Hey, Newt Gingrich!" and he doesn't answer, you know that it's him not answering. I answer every e-mail. I'm probably about 2,800 behind right now, but that's not that bad considering I get over 1,000 a day.

Your book is very optimistic — you talk a lot in the book about how if you want it hard enough and if you work hard enough, the tools now exist for you to be able to build your own brand.
I don't sell you the 40-hour workweek. It's going to be a lot of work. But do what you love. So if you love the Dallas Cowboys or you love gardening or you love tae kwon do, all I'm asking you to do is allocate [the time spent] consuming that content to providing it. For $200 for a Flipcam or an iPhone, you are on television. You don't have to go to L.A. and wait tables and hope somebody from CAA discovers you.

Is your last book going to be How I Bought the New York Jets?

You're totally serious about this.
I would say I'm a solid two decades away. From a business standpoint, I'm very serious. I can do it. I've already talked to Mark Zuckerberg from Facebook to make sure he keeps a couple hundred million on the side.