Gary Vaynerchuk recalls how he first fell in love with wine, and explains how he turned his successful career as a wine retailer into an even more successful career as a video webcast host. He also clues Big Think in on his upcoming ten-book series.

Question: Do you have a story of when you first fell in love with wine?

Gary Vaynerchuk: Yeah. You know what funny is that my Dad had a liquor store. We were Shopper’s Discount Liquors. That was the store I grew up in.

Wine was not at play in my household. My Dad drank Vodka and Cognac because he’s a good Russian boy. That’s what we do.

I first fell in love with wine when I realized people collected it. And so my reading began at 17, 16 because I wanted to know a lot about it because people collected it. That was my hook. I was a collector. The actual loving of wine started really happening at like 22, 23, when it started going from being a commodity to being, oh, man I really like this stuff. This is interesting. Look at these crazy flavors, like how the heck did that just taste like a racquet ball? Like, those kinds of things.

So, there was one specific Amarone that I had at a tasting when I was 22, when I could really taste the chocolate. So much so that I walked outside and called my Mom. Remember when cell phones were like this big, like that. I called my Mom and I was like, “Mom, it’s going to happen. I can taste these things. I can’t believe this, but I just tasted chocolate in this wine.” And that was probably when I was, like oh, this is really getting good. I was just enjoying it.

Question: Did dissatisfaction with your retail job lead you to Wine Library TV?

Gary Vaynerchuk: I think, I turned 30 on November 14, 2005 and there is a one percent of unhappiness. Like, okay. I want to buy the New York Jets and so that's going to cost a couple billion dollars. Am I going to really make a couple billion dollars selling just wine? And the realization was I could have big, big things happen. I launched Wine Library in 1997, but the laws in this country—people watching this video right now in Boston can't buy wine from me.

So I want to do something else and at the same token, as I was feeling this itch in November, I went to a tasting in December and realized people did not have wine self-esteem. They wanted to drink the same 'ole stuff, they wanted to be jerk-offs to each other because they felt they knew something because they read it in the latest Spectator.

I just felt the wine culture had a lot of opportunity to be much cooler and there is so many places around the world that I've traveled to where there isn't this uptight aspect to the wine industry. It's much more a part of culture and daily life and I felt like I was the kind of character, I knew my personality, and my DNA, and my hustle could create this platform that, not only would be successful then by virtue of that success, would create a different kind of culture.

It wasn't so much that I was dissatisfied as if it was just I wanted to change the game again. There was an amazing feeling for me when I launched WineLibrary.com in 1997. It was one of the first wine shops to do so—less than a handful—and it changed the game. It blew up my family business from a couple million dollars a year to a 50, 60 million dollar year business. I wanted to do that again. I want to be a pioneer. It's what I want to do.

So that's what I did with Wine Library TV.

Question: What mistakes did you make when you were starting Wine Library TV?

Gary Vaynerchuk: You know, if anything maybe I was little bit too aggressive. I just e-mailed everybody and was like, "Hey. Let's do this. Check out my show, what can I do for you." And the same token—I don't think of that as a mistake. I feel as though I was a little bit more raw. I think six months later I was a little more polished, but I wasn't more selective. Everyone was like, "Why don't you get selective? Don't hit up everybody. Hit up the top tier. You can't blanket e-mail everybody." When people talk about marketing, I think that's crazy.

I feel like Wine Library TV was itsy bitsy tiny in 2006 but if somebody hit me up they'd be really happy to have the relationship today.

So, what? Just hit up the top 500 Twitter people today? That's insanity, that is elitism. I pride myself in having a lot of hustle and that's what I did. If a top wine blogger was upset that I was hitting up everybody, that might have been a mistake in some people's eyes but not in mine.

So I am sure, a million mistakes. I built a big business around me, it's not the most scalable thing in a lot of people's opinions, but, to me, I understand kind of the vision that I see going forward and I try to stay away from mistakes. The mistakes I make are the opportunities I haven't taken, like big platform television and things like that.

I am sure there are mistakes in my no's, but there is very few—let's get really obnoxious—there is zero mistakes in my yes's because normally my threshold for a yes is first learning—not necessarily the results. I need to know this. I've thought about bc'ing companies just because I've never been bc'ed even though it's a stupid thing to do financially, for the learning process.

Question: Was there a big publicity moment that launched the show to the next level?

Gary Vaynerchuk: There was one big moment—that was the day I was on Conan O'Brien show, and Slate.com wrote a huge profile on the same day. This was in August 2007, so Twitter was still a baby and that whole community we all knew each other kinda sorta. So it became the only thing people talked about on Twitter—watch Gary on Conan—which was really cool. I was really starting to foray into the tech world, the Web 2.0 world, the social media world, whatever the heck you want to call it. It was one of the first people to kind of make it, right. Oh, my God. He's in his office talking about wine, he's not on the Conan O'Brien show. It went really well on top of that.

So it was a big moment. It was the first time wine was getting late night exposure. On multiple levels, it was an interesting and important moment, both in the wine business and in the tech space. I would say that is the one moment that really I can pinpoint. Other than that, I am not very big on analytics and metrics and paying attention to traffic and did we go 23% and this and that. I know what I am doing is right. There is no ounce of me that has any doubt and I work for myself, so there is no justifying it to the dinosaurs that sign my check. So it puts me in a very substantially good position in a lot ways, plus I've done it before.

I was making lots and lots of money; thousands of dollars a weekend selling baseball cards. I've built up a family business. In the first year, I ran it from three to ten million in sales. I know what I am doing. When it comes to making money and building brand, it's just something I was born with. I'm not going to pat myself on the back, this is just DNA.

Question: How did you capitalize on that exposure?

Gary Vaynerchuk: I'm a marathon runner. Capitalizing on something like that just doesn't work. I signed with CAA. I got more exposure. Nightline did a piece, Ellen did a piece. I got lots more Twitter followers. People cared more.

There's a lot of things that happened, but at the end of the day, what I think is important is that people have to understand it's a marathon. Building a business doesn't happen in six weeks. There are no shortcuts. Getting a Twitter account isn't a magic potion. People roll up on me, especially in 2008, "I got a Twitter account." I was like, "Great. What do you want? A cookie?" It's not going to change your business, but at the same token, the people that think this stuff is silly and it's not important are just trying to draw lines in the sand because they don't want to be a part of it. That's a huge mistake because unless you're retiring in the next six to 12 months you better understand what this is all about inside and out.

Question: What is your vision for your upcoming ten-book series?

Gary Vaynerchuk: My vision is that I sell so many copies of Crush It!, that Harper Collins gets off my back and I can wing these next nine for the rest of my career. Is that a good answer?

Question: Can we tell HarperCollins that?

Gary Vaynerchuk: Oh, you can tell them. They know exact – you know the funny part is this. What I loved about it was I signed with Harper Studios. It’s a totally different model. I got offered almost as much for one book as these guys gave me for ten, but the rev share on the back end was substantially more. So, they’ve changed the model quite a bit, and I’m betting on myself, right? So, obviously I want to participate and win on the back end. So, I am very hungry to see what I can do with this book and I’m going to work really hard at it and I’m very confident.

Recorded on: September 15, 2009.