A (very young) midlife crisis at 30 inspired Gary Vaynerchuk to start his video podcast, Wine Library TV, which is primarily about wine, but also about action figures, the New York Jets, thunder, and of course Vaynerchuk himself and his quirky onscreen persona.

That quirky persona and unpretentious wine expertise has propelled “Gary Vee” to popularity on the Internet and in the mainstream media, bagging television appearances on “Ellen” and “Late Night With Conan O’Brien” and other shows. More recently, Gary Vee has authored a book, Gary Vaynerchuk’s 101 Wines: Guaranteed to Inspire, Delight, and Bring Thunder to Your World.

Topping off this list of accomplishments, Internet television network Revision 3 today launches Wine Library Reserve, a condensed version of the weekday Wine Library TV program.

Vaynerchuk was in our hometown of Des Moines, Iowa, this weekend, for a book signing at East Village Books. Podcasting News’ Publisher, Elisabeth McLaury Lewin, sat down with Vaynerchuk beforehand for an exclusive interview.

Elisabeth McLaury Lewin: I’d like to start at the beginning. When you were just a teen, you started working in your parents’ wine business. But even before then, you already were a failry successful businessman — “business kid?” What did you do before you got in the wine business?

Gary Vaynerchuk (Gary Vee): My neighbor growing up said “no season was safe” from my moneymaking efforts. Winter – snow shoveling. Fall – raking leaves, car washing. Summer – I had multiple lemonade stands… I was very entrepreneurial. When I was 12, I got very into baseball cards, and by the time I was 14, I was doing weekend baseball card shows at malls and Legion halls. I was making a lot of money…like a thousand bucks a weekend.

Elisabeth McLaury Lewin: As a baseball card dealer, were you a big fan of the Mets, the Yankees, or the Phillies, or some faraway team?

Gary Vee: I was a big Yankees fan, but was a Jets/Yankees fan, which is an unusual combination. But since I was born in Russia, and we had no tradition of sports teams like you do in America, you just like whatever teams your friends like. I’m very happy being a Jets fan; it’s a huge part of the Thunder Show – I talk about the Jets constantly.

Inspiration: Ze Frank, Lazy Sunday & A Mid-Life Crisis

Elisabeth McLaury Lewin: In your mid-teens, your folks said you needed to quit the baseball trading, and help them out with the family business. As an adult, you stuck with the business. Talk about being in the wine business, and talk about what sparked your need to start a podcast …? That’s not what every already-successful, established businessman decides he needs to do.

Gary Vee: So, I was about 15, making lots of money selling baseball cards. My dad came to me and said that I had to start helping out. You know, first generation immigrants, the oldest son has to go and work. So, I dusted bottles and made ice – it was the worst.

But at 16 or 17, I realized that people were not just drinking wine – but collecting, too. And I LOVED collecting things – comics, baseball cards, and toys. That was the first hook I got into wine. We changed the name of the business from Shoppers’ Discount Liquors to Wine Library, started the Wine Library website, I took over the business when I finished college, after building up equity in the business over 5 years. I really built up the business. We went from $4 million/year in sales to $50 mil/year in sales in 7 years …. And then I turned 30 and freaked out, and decided I needed to launch a video podcast.

Here’s why that happened: We did so much Internet business that we had 3 or 4 full time web developers. I always pay attention to the nerds, when the nerds talk I listen – the tech scene is the future. They were watching Ze Frank and Rocketboom. I couldn’t do blogs because I wasn’t a great writer… So I waited for video – I saw that YouTube and SNL’s “Lazy Sunday” video were so crazy popular, that was the trigger for me to think I was ready to do a podcast because people were ready for Internet video.

So, in a nutshell, it’s that I turned thirty and had a midlife crisis, right at the time when video was getting big, and I was freaking out about growing the business and getting big. We were already successful, but someday I’m going to buy the New York Jets, that’s going to be multi billion dollars – you can’t do that on $50 million/year. I need to do a lot of damage! I started embarking on changing the wine world, and expandig my personal brand, and creating some fun for myself, doing a new challenge.

Elisabeth McLaury Lewin: And you’ve amassed a huge library (no pun intended) of shows, and you’ve been wildly successful. Everyone has their own theory why you’re so popular. You just exude a really hyper enthusiastic personality, and you seem so accessible to your viewers. But what do you think makes you so successful? What’s your secret?

Gary Vee: Um, that I don’t care about myself or the money.

It’s kind of tricky not caring about yourself, but it’s true – my mom is the same way. I don’t look at things or make decisions that starts with “How do I feel about that?” It’s always “How does X feel about that?” I think it’s a rare disposition, but I think that’s ultimately why I’m always going to be successful.

[my outlook is] DNA-driven. I’m realistic about what’s going on around me. I keep it very basic. All I really care about is the health and well being of my friends and my family. When you do that, you become much happier. That’s a very unique thought process. …It’s how I felt forever. … Even before I had any money, I didn’t care about the money – but I always knew I would achieve big things.

But I keep it very basic, I am very convinced of what I’m doing, I give and give until I can’t give anymore, and I WORK MY FACE OFF. And I think that a lot of people don’t like that part. But you’re gonna succeed in what you give. If you give 15 hours a day, you get 15 hour a day results. I give every day. Every second. 24/7/365. It’s how I breathe. It’s how I live. It’s how I think, and if you give like that it’s hard to not have that kind of success.

Elisabeth McLaury Lewin: Did you see the podcast itself as the means to some other end? The podcast has been something that has parlayed itself into other good things for you. How do you measure what success is?

Gary Vee: How I feel in my stomach. How much closer I am to buying the NY Jets.

See, for me it’s very simple: People need to have a goal outside their real life goal. My real-life goal is to spend as much quality time with people as I can. Starting with my family, next with the closest friends, but not ending with total strangers. Even this moment is fun for me. This moment is really good.

I did a video on Gary Vaynerchuk.com about how I want to meet every person on earth …. I know I mean it!

I measure my success by the way I feel inside my tummy. [laughs] There’s a quote!

The only thing I want besides the basic things of time and health and experiences with people I love, is to buy the New York Jets. Everything is a stepping stone, part of the foundation. For me, all I want to achieve is to reach this outrageously big goal, and everything in between is meeting as many people as possible. So, for me, I’ve won. I can’t lose.

Building Your Brand, & Meeting Everyone In the World

Elisabeth McLaury Lewin: Toward the goal of meeting every person on earth, you have this incredible huge community based around Wine Library TV…

Gary Vee: Today you’ll see it in action. Half tech and half wine.

Elisabeth McLaury Lewin: … and there’s a big buzz locally about this book tweetup that we’re going to in an hour. Talk about the different pieces about your community, about your social network, and then let’s talk about your book.

Gary Vee: There’s a video I did called “one trick pony.” I’m so baffled by why people and our society try to pigeonhole people into one dimensional creatures. I’m thrilled that I’m the wine guy and a social media maven. It’s fun, it’s just who I am, those are two things I actually do. But I’m also a big time marketing guy, and could do a lot in that world. And can talk a lot about green English peas. I mean, there’s a lot of things I’m good at, that I know a lot about. I don’t listen to the marketing rule of “be focused, be the king of a domain, do one thing well.”

I embrace me – I think more people need to do that.

You might be an unbelievable chef who’s well known locally or nationally. But if you’re an outrageous stamp collector, that needs to be a much bigger part of your personal brand. And for me, I know how to build personal brand on the Internet, and I know how to use social media products, and I want to help those people too. That’s why I have such a following on Twitter – those 10,000 plus people aren’t all wine fans, and obviously I know a boatload about wine, and I love that, too.

There’s a very good chance the next book I write will be about business and marketing and looked at more like the world is flat, or sticky or has a long tail. See, I don’t consume a lot of media, don’t read that much or watch tv or read enough blogs, but I put out. I give out to my community. And it attracts a lot of different kinds of people. My demographic is all over the place, it’s very hard to pigeonhole my demo.

Elisabeth McLaury Lewin: But within your online presence, you have forums, a library, faq’s ,applications, and widgets… and now you have a book and now, there’s a book tour that allows for a real-life face to face interaction with your community. Which is why we’re talking now in Des Moines, Iowa in June 2008.

The title of your book is Gary Vaynerchuk’s 101 Wines: Guaranteed to Inspire, Delight, and Bring Thunder to Your World.- what does thunder mean?

Gary Vee: Thunder is a term I’d use as a teenager with my friends when we were playing video games or watching sports or movies, if something good whould happen, I’d say it would “bring the thunder.” It transcended into my lingo. If I found a good wine, I’d say it brought the thunder. People gravitated toward the phrase, so I picked up on that, and made more light of it.

The book is written for 2 simple reasons: One is to reach people and change their wine world who I know would not watch a video podcast.

But the biggest reason is that I wanted my mother to be able to tell people that her son was an author. (I also thought it would be ironic for all the teachers who gave me D’s on my writing all throught school). It also gives me platform and opportunity for a book tour – even without a book, I want to do Gary V tours and talk with people around the country. It’s a book about this year’s 101 favorite wines. It’s been very rewarding.

Elisabeth McLaury Lewin: Do serious podcasters worry too much about monetization and not enough about reputation? Seems like you think money is nice, but is not your most important driving factor, by a long shot.

Gary Vee: So, you have to know your situation. If you can afford to do podcasting or blogging that you can leverage and monetize against your own product or personal brand, great. If you can do it outside your 9 – 5 job, do it. Money should never be the number one agenda. If you quit your job and you do it, money should be your number one agenda — but you never should have quit your job, and too many people make that mistake. If you’re doing this because you can afford to, for whatever reason, you have to understand that the quicker you’re going to go for the cash, the less you’re going to have of it. Period. It’s a very simple fact.

I don’t care about it, because I realize that the second I care about [the money and the podcast], things will change. I don’t make any decisions about my podcast without my community in mind. If I did it with financial rationale behind it, there would be conflicts about what would be good for the community. If you think more about the long term instead of short term, the more success you have in the short term.

It all depends on the one thing – patience. Belief. I believe and I know. And so I don’t need to do it right now. I’ve been offered a crapload of stuff, but I’m not going to take the first thing that gets offered to me.

Reputation is all you’ve got. Your personal brand is all you’ve got. It’s what you monetize against.

Oprah could have done something different a long time ago, but she didn’t, and now that’s why she monetizes on such a grand scale. Kevin Rose almost sold Digg at a $million five to Jason Calacanis, but he didn’t. Thought about it – It would have been a big mistake. So, you know, sometimes you monetize too early.

You need a steady cash flow, and then after that, only worry about the community. Yes, you need to monetize first perhaps, but you can’t become Spam City USA. You have to do everything so that it doesn’t negatively affect your community and your brand and your reputation and what yo’re trying to accomplish. If you’re going to monetize, you’re going to need to be obnoxiously transparent. No product placement, no secret deals.

On The Revision 3 Deal

Elisabeth McLaury Lewin: Speaking of monetization, and speaking of Kevin Rose and Digg — I see you’ve inked a deal with Revision 3, and Digg is their original flagship “brand.” How will that change what you’re doing, by aligning yourself with Rev3?

Gary Vee: So, nothing change with Wine Library TV day to day. When you go to Wine Library TV.com, you won’t see any mention about Revision 3, we’ll live within Revision 3, they’re doing my content but they’re doing something really awesome.

This is the first time I’m talking about this; since we’re launching on Monday. They’ll be making something called Wine Library TV Reserve, which will be a 3 minute cut down of Wine Library TV. I watched the first one – I was shocked at how much the essence of the show can be captured in three minutes, and I’ll probably lose a crapload of audience to this shorter show. They’re gonna have a home run.

It’s really really neat. They’re going to have a very unique product, that a lot of people are going to be attracted to, and I’m going to be very engaged in the Rev3 community. They’re going to monetize against it,
but those ads won’t be on the long form Wine Library TV version of the show.

I totally believe in the Revision 3 community. There’s a lot of talent there. I went out of my way to make sure my younger brother interns there this summer – good people, good family people. I choose to do business with people who are great human beings.

That starts on Monday June 23.

Elisabeth McLaury Lewin: What’s your next step in your grand plan to buy the New York Jets?

Gary Vee: I have no idea.

I only make decisions based on my heart and intuition (after I do the market research). Who would have known three years ago that I’d be doing a daily video blog? There’s no way! And so much of my life now, everything, is based on that project. There’s a lot of stuff I get offered…

On The Secret Of His Success

Elisabeth McLaury Lewin: What’s something that people don’t know about you?

Gary Vee: A lot of little tidbits that people wouldn’t otherwise know, I’ve Twittered out here and there. I’m a huge fan of boy band music, for instance, and I’ve been talking about that on Twitter. That’s kind of surprising and ridiculous.

Okay – I’ll give you something that other people don’t know…

I don’t pee that much. I think I pee at a very low ratio, in comparison to my family and friends.

There’s your scoop.

Elisabeth McLaury Lewin, (trying to regain composure): What’s a great summertime wine, or a wine for cleaning up the Great Flood of Iowa?

Gary Vee: I would send everybody this summer to get some Torrontes, a white wine from Argentina. $7 – $12.

Elisabeth McLaury Lewin: Parting words?

Gary Vee: Life is completely controlled by you. And I think that, I want more people to take control of their lives and understand that they are the ones to paint the picture of their lives. You can do anything you want. The moment the game is broken, you take control and change it.

I made a huge change on my 30th birthday. I was 99% happy. But that 1% I wasn’t happy made me change my entire life, and I am so much the better for it.