Gary is a New York Times and Wall Street Journal Best-Selling author who is also a self-trained wine and social media expert. From a young age, it was clear that Gary was a businessman. At 8-years-old he was operating seven lemonade stands in his neighborhood and by 10 he had moved onto selling baseball cards at local malls.
Click to tweet: Fire Nation, Gary shares his incredible journey on EntrepreneurOnFire today!
- “Legacy trumps currency.” – Gary Vaynerchuk click to tweet!
- Gary takes us through his mentality of what it means to be an Entrepreneur. Very enlightening, to say the least.
Entrepreneurial AHA Moment
- Before people even thought the Internet would effect family-run stores, Gary was out there at 21 pressuring his dad to take a leap of faith. His dad did, and the rewards they reaped are legendary.
- VaynerMedia is on the cutting edge on so many levels. You simply have to hear Gary’s vision for the future… it’s like looking into a crystal ball.
Lightning Round Resource
- Rebel Mouse: Your social front page
- Gary’s facebook
- Crush It!: Why NOW Is the Time to Cash In on Your Passion by Gary Vaynerchuk
- The Thank You Economy by Gary Vaynerchuk
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John Lee Dumas: Okay. Let’s get started. I am simply thrilled to introduce my guest today, Gary Vaynerchuk. Gary, are you prepared to ignite?
Gary Vaynerchuk: Born to ignite, my friend!
John Lee Dumas: I love it! Gary is The New York Times and Wall Street Journal bestselling author who is also a self-trained wine and social media expert. From a young age, it was clear that Gary was a businessman. At 8 years old, he was operating 7 lemonade stands in his neighborhood, and by 10 he had moved on to selling baseball cards at local malls.
I’ve given Fire Nation a little overview, Gary, but why don’t you take a minute. Tell us about you personally, and then tell us a little bit about your business. The ones you have going on right now.
Gary Vaynerchuk: Sure. Thanks, John. First of all, I just want to thank anybody who’s listening to this. It’s funny, I grew up an entrepreneur. I remember that word when I was a kid – I’m 37 now and believe that being an entrepreneur was the best thing – but back when I was a kid, and even up until like let’s say 5 to 7 years ago, being an entrepreneur was almost like a loser. It kind of meant that you had 7 things going on, but not really and you lived on the beach. It’s amazing to see an entrepreneur become this new thing that is something that I’ve always associated with. So again, thank you for supporting John who I think is creating a platform for entrepreneur stories. Storytelling is the game, and so I’m flattered to be on, John. Yes. I mean lemonade stands, baseball cards, making thousands of dollars a week when I was I was 12, failing my classes because I didn’t give a [Expletive]. Oh, but John, am I allowed to curse on this podcast?
John Lee Dumas: Well, try to stay away from it as much as possible. I’ll bleep that out, but we’re cool.
Gary Vaynerchuk: Cool! So I definitely was very focused on selling stuff. I got dragged into my dad’s liquor store when I was 14 and fell in love with wine when I was 16 and decided I wanted to build the biggest wine shop in the world and 100 of them, 500 of them. Later, the Internet is something that came across my life and I realized I didn’t have to open up 600 stores. I launched WineLibrary.com in 1996, so I was 21. I built WineLibrary.com and Wine Library the store from a $3 million to a $60 million business in a six year period, and then started Wine Library TV in 2006, which was a daily wine video blog that created a lot of notoriety and Internet fame for me. I used Facebook and Twitter and YouTube and things of that nature to build up that fame. That led me to writing books about business, which led to brands asking me about this stuff in ’07, ’08, and in ’09 I officially launched VaynerMedia, a social media agency that I now run with my brother and a 200 person firm and building a big business.
John Lee Dumas: And one day you’re going to own the New York Jets.
Gary Vaynerchuk: Yes. So thank you, John.
John Lee Dumas: [Laughs]
Gary Vaynerchuk: My big goal is to buy the New York Jets. I’ve done some angel investing and other investing in the last several years and I’ve done quite well with like Facebook, Twitter and Tumblr, so I feel ambitious and opportunistic, and so I’m excited about it all.
John Lee Dumas: Awesome, Gary. Well I’ve excited to continue delving into your journey, but before we do, I love starting off EntrepreneurOnFire with a success quote because it really gets that motivational ball rolling and gets Fire Nation pumped up for the rest of the content that you have for us. So what’s your mantra, what’s your success quote that you have for us today?
Gary Vaynerchuk: For me, John, I think there’s one video I made – and I made 1,100 wine videos and probably 300, 400 business videos and all my keynotes and interviews are on YouTube. The one that sticks to me, the one that if you said that nothing could be on the Internet but one thing, would definitely be the video I made called “Legacy Is Greater Than Currency.” I make all my business decisions based on will I be looked back at as somebody who was smart and good and really a winner, and not how much money I’m going to make. I think everybody’s playing the short game and I’m playing the long game. And so while everybody’s going to business with putters, I’m going with the driver. So to me this is long term. This is marathon thinking and not sprinting. I’m training for marathon. It’s endurance, it’s relationship. It’s not about the quick score or the quick close.
John Lee Dumas: That’s great stuff, Gary, and I also love the fact that you are just all about the journey and you’re all about the story. You’ve already alluded to that before. That’s why I created EntrepreneurOnFire, because I wanted to give entrepreneurs like you a medium, a platform to share your amazing journey. So let’s go back to a point in your journey where you actually failed or you came against an obstacle or a challenge that you just had to really dig deep and overcome, and then take us through how you did overcome that obstacle.
Gary Vaynerchuk: You know what’s funny, John? I don’t think in very local terms. Again, back to the sprinting-marathon metaphor. I don’t really know. I think my biggest hurdle that was very obvious to me was being an F student in high school where being 14, 15, 16, even though I had a lot of bravado and confidence and ego, it wasn’t mature enough to be my complete foundation, and I struggled when parents or teachers thought I was a loser or just not going to be successful. It weighed on me. It’s a chapter when I think I cared what people thought. Society teaches you that your school grades have an impact. I was just so confident that it wouldn’t for me, but it was still hard. It was a challenge when my friends were getting into good colleges and I wasn’t and things of that nature. So my youth was a little bit of a challenge. I would say my challenge of I grew a family business and I my dad and I barely agreed on anything. So the challenge of the arguments and all those things was difficult at times. It was a day-to-day battle, both of us highly emotional and highly competitive and highly into it.
And then ultimately, probably my biggest goal, which was I don’t let things come easy to me. Meaning, I put a lot of my own shoulders. I don’t expect enough from the people around me or create a situation where they can help. Not that I micromanaged because I haven’t, but at the highest level, I think I’ve micromanaged and put a lot on my shoulders, and that’s creating a lack of upside. I don’t think of building the platform. I think about executing within the platform. I think that’s small thinking and I need to challenge myself, and that continues to be a battle I think about so much as on me and I need to figure out how to make it less about me. That’s one of the biggest reasons I’m building VaynerMedia. I feel like I’m building a company that is executing the kind of things that I believe in, and then I have it as an asset to build bigger things for me in the future.
John Lee Dumas: Those are just powerful insights, Gary. One thing as entrepreneurs, when we start out, we at some point hit a wall. We either need to find out how to climb over that wall to continue or to pivot and to get around that wall in some other manner. Have you ever hit a wall at some point in VaynerMedia or even a venture before that when most people would’ve given up and people actually maybe were telling you to give up, and you didn’t and you kept striving forward? Take us through that.
Gary Vaynerchuk: On a local level, I think we all hit walls on a daily, weekly, monthly level. I’ve never hit a wall on a global level, except maybe one really difficult argument with my dad where I was like I don’t know if I want to still do this, and then the love for my father trumped those feelings. But other than that – listen, I only started operating VaynerMedia 15 months ago, September of 2011. Prior to that, it was AJ’s show through and through. I mean I did the selling and got us clients, but AJ was really executing, and miraculously, given his youth and greenness. So a lot of times I thought about selling Vayner and things of that nature, but never really wavered as can I do this from a talent standpoint or like putting money in the bank ever at Wine Library or VaynerMedia. It’s been more emotional family dynamic. So do I really want to do this? When it comes to like I’ve thought about do I want to play that game in life. But once I play that game, I win.
John Lee Dumas: Absolutely. Gary, having read your book “Crush It!” and I just followed you for quite some time now, you were just that kind of person that has aha moments so often. You’re having these little inspirations that are just inspiring you, that are moving you forward, that are just making you pivot your business and change directions. Can you take us back to some point when you really just had this massive light bulb that just went off and it just clicked and you said, “Wow! This needs to happen,” and then take us through how you turned that light bulb moment into success.
Gary Vaynerchuk: That’s a great question. I think you’re right. That’s happened to me quite a bit. I remember working with the developers of my website in 1998 when we were starting to see like people were actually buying things on the web, and I had an aha moment thinking, I have to hire these guys. Now remember, this is 1998, 1999. It’s a little bit closer to 2000. Let’s call it 2000. This was 12 years ago. John, how old are you?
John Lee Dumas: I’m 33, Gary.
Gary Vaynerchuk: Right. So think about it. You’re 21. One thing about your 21st birthday, right? It’s not that long ago, but it’s long ago, right? It’s 12 years ago and I have to convince my dad – this is a family liquor store business in New Jersey pre-cell phones, pre-mobile devices, of cell phones that have Internet.
John Lee Dumas: Right.
Gary Vaynerchuk: Pre most people believing that they wanted to put a credit card into a computer, pre Amazon dominating, pre-tablets, pre-Facebook, pre-YouTube, pre-Twitter, pre Google AdWords being a real force. This was a long time ago, in essence, and I’m convincing my dad that we have to hire a fulltime computer developer for our local liquor store.
John Lee Dumas: Yes.
Gary Vaynerchuk: So that was a big aha. Like we were going to be a computer company and I don’t think people understood it. Just the same way I feel everybody’s a content company now and they don’t really understand it. And so that aha moment was big and I really battled my dad. I said things like “Take my salary, but I need this.” And so that was a battle. VaynerMedia, 12 months ago when I realized, wait a minute, this is about the micro content, this is about the actual content in these social networks, and then pivoting from a community management company to becoming a content company. It’s been painful and it’s been aggressive and it’s been fast and it’s been intense, but it’s really paying off dividends.
John Lee Dumas: So Gary, throughout your journey, have you had an I’ve made it moment?
Gary Vaynerchuk: Oh yes, a couple. I would say a couple. I would say that in the liquor business, there’s a magazine internal called Market Watch which has a Retailer of the Year thing, and I always wanted to be on it for Wine Library and I made it as the youngest person ever when I was 27. That was a big I made it moment that me and my dad were being recognized as the best retailers in the country. That really mattered. I would say that in that same year or maybe a year later when I was on the front page of the Wall Street Journal and they had a sketch, that was a little vain aha, I made it moment that was fun. But the truth is, John, I think I’ve made it a long time ago because of how I got parented and what my DNA is. The only thing I really professionally want to accomplish is buying the New York Jets. And so I guess I never really have the big aha, like I made it moment, until that happens. On the flipside, to give you a little bit of a scoop, John, which I don’t talk a lot about.
John Lee Dumas: Awesome!
Gary Vaynerchuk: And so I’ll give you a little something that I haven’t given other places. Truth be told, I really don’t give a crap if I buy the Jets, right? It’s the climb. There’s a dirty secret that’s starting to go around my family and friends, which is that I don’t want the Jets to win the Super Bowl. I’ve been thinking about it lately because I think it’s true and it’s because of who I am. I love the journey much more than the actual event. And so I’m actually worried that the day after buying the New York Jets will be the worst day of my life because I’d be like, “Really?” Like “Now what?” I guess it’s going to be winning Super Bowls, but the psyche of me is I’m wired for the long term, the legacy and the journey. Not the actual thing.
John Lee Dumas: Have you ever been able to have a conversation with Mark Cuban about his experience buying the Dallas Mavericks, taking them to a championship and winning the championship? So he’s gone through all of those things.
Gary Vaynerchuk: Yes. I haven’t, and I’ve never really sought him out. We’ve interacted a couple of times in South by Southwest. I don’t know him super well. I have friends who do and are always like, “You should have dinner with Mark.” I’m kind of funny, Mark Cuban in a way, one, I don’t look up to Mark. I mean he’s done what I want to do but – and by the way, I love his bravado. It’s not that I don’t look up to him because I don’t think he’s successful or I don’t like his style. I actually love his brashness. I’ll probably end up being very similar on that stage. I just don’t. And so I don’t have any real passion to meet him, and I’m competitive with him, right? In a weird way.
John Lee Dumas: Right.
Gary Vaynerchuk: Yes. I mean I’m not the kind of guy that gets any juices going from somebody saying, “You can do it and this is how I did it.” It’d be fun to do business with him if it’s a business objective, but I’m not inspired externally, John.
John Lee Dumas: No, I get it. I just think it’d be really interesting to know that Mark Cuban who’s a very Type A personality who’s had success and he has had…
Gary Vaynerchuk: He’s done it.
John Lee Dumas: He’s had I made it moments on so many levels and he’s already gone through kind of what you’re looking to potentially go through. I’d be curious to see.
Gary Vaynerchuk: Yes. You know what’s so funny? My lack of wanting to meet him probably speaks to how little I really do care about buying the sports franchise.
John Lee Dumas: Right. That’s interesting.
Gary Vaynerchuk: As a matter of fact, I probably look down on him and the fact that he accomplished it so fast. The journey is the game. I’m so into the [Expletive] goddamned journey, John.
John Lee Dumas: I love that, Gary. That’s exactly why I ask this question about the I’ve made it moment, because I always get different answers from every single entrepreneur. Some entrepreneurs say, “John, I have an I’ve made it moment every single day.” Other entrepreneurs say, “John, I will never have an I’ve made it moment because that will denote the end of my journey.”
Gary Vaynerchuk: Yes.
John Lee Dumas: For me, it’s somewhere in the middle. It’s like you need to appreciate and celebrate these milestones.
Gary Vaynerchuk: You know what, John? I think I’m a contradiction. I’ve been thinking about long term like what am I going to call my autobiography because that’s kind of the character that I am.
John Lee Dumas: Yes. Right, right.
Gary Vaynerchuk: I think about calling it like “The Bridge” because I think I’m very different and very polar opposite, but evenly within myself. Meaning on a basketball court, John – and this is true – if I’m playing basketball and you told me before we got there and we became good friends after this and like became good friends and knew each for 10 years and played basketball and you told me, “Oh, Gary, last week I really hurt my knee. So I got to be careful” and I’m like, “Cool.” I literally would use that against you on the basketball court. In a real way, that would probably be appalling to most people listening.
John Lee Dumas: [Laughs]
Gary Vaynerchuk: At the same token, if you meet me only today and said, “I need $3,000 because I have a real bad issue with my car” and we barely know each other, I might give it to you. Not always, because I get asked a lot. That’s just the world. So like I’m a funny dude. Like I want to kill everybody and I want to love everybody, right? I want to beat you, but I want to be your best friend. I care so much what people think of me and you’ll never meet anybody who cares less of what people think of me. And so I’m a contradiction.
John Lee Dumas: You’re a walking contradiction, Gary, and that’s part of what people love about you and that’s part of why they love your books and your content, because you are just a contradiction of sorts and people never know what they’re going to get and people love the surprise, the unopened gift.
Gary Vaynerchuk: I genuinely care about people, but I know that business is business. I will try so hard to over-engage, but I respect that I can’t with everybody. I genuinely love people, which, if you ask me, is probably dramatically more why people like me, because deep down, at the end of the day, when push comes to shove, there’s a lot of people that find me too much and will think I’m a wanker, but when they get to know me, will like me. As long as I’m winning it in a place where people really know who I am and they like me, I’m going to win that game long term. Like I try to fix my mistakes. There’s a couple of people who used to work at VaynerMedia who are unhappy with me or their experience of Vayner, I’m grossly trying to reach out to them. Like it’s just how I roll.
John Lee Dumas: I love your straightforwardness and I love your vision. So on that note, Gary, let’s talk about your current business right now. You have so many things going on. What are a couple of things that are just really exciting you right now?
Gary Vaynerchuk: Well, it’s funny. VaynerMedia never spoke to me because it was client services and I don’t like the business model of client services, right? You don’t get a big return on your sale if you ever want to sell the company. It’s very human-based, which is tough to manage. It’s just a very difficult business. But what’s exciting to me is we’re finding our groove and I think we’re teaching Corporate America and Fortune 100s and 500s that there’s a lot of opportunity just to retail in a different way. I love when the world’s changing and I love to try to be first in executing the proper way to win in that changing world. I think VaynerMedia and producing content [made of] to Facebook, Pinterest, Instagram, Twitter, is doing an amazing job at that and that’s exciting me tremendously. So my work at VaynerMedia is exciting me.
I’m starting to work on a new book called “Jab, Jab, Jab, Jab, Jab, Right Hook.” I’m very excited about that. That’s the thesis of the work we’re doing here. Other than that, I’ve been shockingly focused on Vayner. I continue to explore TV opportunities because I think it’s an important platform. I continue to invest. I made an investment in a company called “RebelMouse” that I’m obsessed with, that I think is incredible. And so that’s kind of some of the top line thinking.
John Lee Dumas: That’s great stuff. Have you settled on a cover for Jab, Jab, Jab, Jab, Jab, Right Hook?
Gary Vaynerchuk: No. Not even remotely close.
John Lee Dumas: When you were saying that, I don’t know why. We’re both in our 30s so this might resonate with you and this might not, but I was just picturing Mike Tyson’s punch out and Little Mikey there.
Gary Vaynerchuk: Yes, that little guy.
John Lee Dumas: [Laughs]
Gary Vaynerchuk: Yes. I’m not sure if I want to pay for the licensing rights for that but…
John Lee Dumas: Oh, that’s true!
Gary Vaynerchuk: It’s definitely something I’m excited about.
John Lee Dumas: Just that counterpunch when you hit the star button. Oh, I love that!
Gary Vaynerchuk: It’s the best.
John Lee Dumas: [Laughs] So Gary, what is your vision for the future? What is one thing that you’re just really excited about over the horizon?
Gary Vaynerchuk: Mobile payment excites me. The fact that credit cards are going to be gone and we’ll all be paying with our mobile device. I’m very into that. I think that’s super interesting and it has a big impact.
John Lee Dumas: Oh, it’s wonderful.
Gary Vaynerchuk: I think things like Google Glasses, the semantic web where there’s technology layered on all our products and not just our phone and our television, but like when our refrigerator is a smart refrigerator or when our jeans – I mean, could you imagine a world, John, where your jeans are telling you to lose weight because they feel more friction against them?
John Lee Dumas: [Laughs] I love that!
Gary Vaynerchuk: I think that world is coming. So I’m into that. I’m into mobile retail. I’ve been thinking a lot about launching a wine app that sells on mobile devices only and is very native to mobile and is very customer-friendly. So mobile selling. Mobile, mobile, mobile, smart world and just the heavy influence of digital natives in society that when the people right now that are 19 to 30 become 28 to 50 and become the market, that impact on the economy is going to be incredible, and society.
John Lee Dumas: Man, I would just love to pick your brain about the future for the next hour, but I promised that I would keep this interview 25 minutes for you, so we’re going to move in to the final topic, the final round, which is called the Lightning Round.
Gary Vaynerchuk: Okay.
John Lee Dumas: This is where I get to ask you a series of questions, Gary, and you come back at us, Fire Nation, with amazing and mind-blowing answers. Does that sound like a plan?
Gary Vaynerchuk: Let’s do it, my man.
John Lee Dumas: Alright. What was holding you back from becoming an entrepreneur?
Gary Vaynerchuk: Absolutely nothing. I mean enormous props to my mom for being a Russian immigrant where all her other contemporary friends were pounding their kids on education as the way to make money in America and the way out, and her supporting me being an entrepreneur.
John Lee Dumas: Love it. What is the best business advice you ever received?
Gary Vaynerchuk: From my dad, hands down. He said, “If you buy it, you buy it. Word is bond.”
John Lee Dumas: Yes. What is something that’s working for you or your business right now?
Gary Vaynerchuk: Communication. Forcing my employees to email less and go and see each other and talk face-to-face more often and meet speaking to people throughout the organization, top to bottom.
John Lee Dumas: Awesome stuff, Gary. You’ve already mentioned a number of cool things like Google Glasses and the such, but do you have an Internet resource like an Evernote, like a Google Glasses that you’re just in love with that you can share with Fire Nation?
Gary Vaynerchuk: No. I’m actually really bad at utility and using those things as an advantage. There’s an app called “Clear” that I thought was going to be great for me to take random notes, but I haven’t used it. I’m actually quite bad at making tools better for me. So the answer is no.
John Lee Dumas: Do you want to get a couple of seconds? You said there was a company that you’re really passionate about that you just had invested in?
Gary Vaynerchuk: RebelMouse?
John Lee Dumas: Yes.
Gary Vaynerchuk: Yes. RebelMouse is interesting. So I believe in micro content. I believe that the pictures you put out on Instagram, the animated GIFs you make on Tumblr, the 140 character words you put on Twitter, anything you want basically on Facebook that you put out, that all these pieces of content are really valuable and really matter, and that the way to story tell in the future is not through articles or TV shows or billboards or radio spots, but they’re going to be through things like these, through the mobile device. I really think that RebelMouse is becoming a place where this all gets curated to, and then you can on top of that, look at the analytics and also change the titles and really act like a publisher or editor, has the chance to become the default homepage for most people in the world or something like it. That’s why I’m so passionate about it.
John Lee Dumas: Wow! Well, Gary, your books are going to be linked up on the show notes page of this episode. If you could recommend another book to Fire Nation, what would it be?
Gary Vaynerchuk: This is going to make me seem like such a [Expletive].
John Lee Dumas: [Laughs]
Gary Vaynerchuk: I really don’t read. I’ve read 11 books in my life. So what I would tell Fire Nation to do is to read AdAge.com and Techmeme.com every day because they’ll give you an insight to how big business works and an insight to like what’s happening in emerging tech, and I think that whether you’re an entrepreneur, a small business or a big business, understanding how big business thinks and understanding what’s going on with emerging tech, the big and the small, is a good counterintuitive bridge contradiction that builds strength.
John Lee Dumas: So Gary, this is the last question, but it’s kind of tricky and it’s my favorite. So take your time, digest it, and then come back at Fire Nation with an answer. Imagine you woke up tomorrow morning in a brand new world, identical to earth, but you knew no one. You still have all the experience and knowledge you currently have. Your food and shelter is taken care of. But all you have is a laptop and $500. What do you do in the next seven days?
Gary Vaynerchuk: I would make a YouTube video saying that I’m a man who was just dropped from another world…
John Lee Dumas: [Laughs] I love it!
Gary Vaynerchuk: And I’m now in your world. I’m from this other world that I come from. It’s all the same stuff. So I fully expect this video on YouTube to go ridiculously viral because I may be the first ever alien. “And please don’t kill me. Let’s all become friends and let me tell you about my experiences.” I would fully expect that video to have 4 million views by the end of the day.
John Lee Dumas: Oh, absolutely, and what’s so funny is you are the 115th interview on EntrepreneurOnFire that I have personally done. Every time I’ve asked this question, you’re the first person that’s tried to leverage that newness [Laughs]. And it’s just so obvious. I mean, that would be so viral, it would be ridiculous.
Gary Vaynerchuk: Oh my God! Could you imagine, John, if we hung up right now and like later today, there’s like, ah, there’s an alien video on YouTube. I mean you think a lot of people saw Gangnam Style. That thing would have 500 million views by the end of the day.
John Lee Dumas: [Laughs] Oh, it’s so true, Gary. Listen, that is awesome, actionable advice, and you’ve given us some incredible actionable advice this entire interview and we are all better for it. Give Fire Nation one parting piece of guidance, then give yourself a plug, and then we’ll say goodbye.
Gary Vaynerchuk: You know, guys, I don’t know what to say, but when you’re 85, you’re not going to care how much cash you made. You’re going to care about how you made that cash. So please think about legacy.
John Lee Dumas: I love the legacy. Where can we find you, Gary?
Gary Vaynerchuk: Yes. I would say everybody here, like please hit me up on Facebook.com/gary, and on Twitter, garyvee.
John Lee Dumas: Love it, Gary. Thank you for being so generous with your time, your expertise and your knowledge. Fire Nation salutes you, and we’ll catch you on the flipside.