Today we have a very special episode. We sit down with Gary Vaynerchuk. Gary Vee is one of these natural born entrepreneurs. He was hustling around at the age of five setting up lemonade stands and selling baseball cards making thousands of dollars a week. He then took his family’s wine business from three million dollars in annual revenue to sixty million dollars in just five years. Now, he runs VaynerMedia, which is one of the world’s hottest digital and social media marketing agencies.

He is also a prolific angel investor investing in companies like Facebook, Twitter, Tumblr, and Uber. He is a New York Time’s best-selling author of four books, popular podcaster, inspirational public speaker, and all-around entrepreneurial giant.

I’m a huge fan of Gary’s. If you know him or follow any of the content that he pumps out on a daily basis, you will know that he’s a very busy guy. We’re extremely lucky to have him on the show. He talks about the most important aspect of being an entrepreneur. It’s not something that you would probably think of right off the bat. He also talks about where he thinks attention will be in 2017.

You know what, if you know him at all, you know he’s very big on attention. I think you’re going to love the episode. Let’s jump right in. Get ready to hear some gold

Jay: Gary.

Gary: How are you?

Jay: Hey, awesome, much better, much better.

Gary: Good.

Jay: Okay, great. Let’s get right into it because I know we’re limited on time.

Gary: Yep, let’s do it.

Jay: Okay. So Gary V, you are obviously a world renowned entrepreneur. Unfortunately for my audience here out in Asia, and I apologize for this, many people probably don’t know who you are.

Gary: That’s much more my fault than theirs. Honestly, it’s actually one of the things sitting in my life that I’m most excited about, which is my future plans of expansion of the content and travels of the speaking, and the offices. It’s almost like a whole new frontier opportunity. Right?

Jay: Right.

Gary: By the way, the way the world is fragmented, even in the United States within social media where it’s probably my biggest crossover of ability of being known, I’m always aware of where I actually sit in lexicon, so I’m excited and I appreciate you having me on and I’m excited to be … I’m excited for so many people hearing me for the first time.

Jay: No, no, absolutely. I think herein lies the opportunity and this is why … You know, me and Alex first connected, so I think you’re going to have a huge, huge opportunity coming forward, and we’re going to get into your views on Asia and China later on. So you’re an entrepreneur. You ware like a born and bread real, real entrepreneur, sort of in your blood. I want to ask you, so why don’t you just run us real quick through your story.

Gary: Yeah.

Jay: Also, about specifically, your parents and how superb they were. The thing is, within Asian culture, it might be similar to your culture.

Gary: It is.

Jay: It’s not supportive. My father, for example, was first generation immigrant from Korea to the U.S. He struggled himself to pay the bills and what not, and so he would be very against … He’d probably disown me if I said “Oh, I’m going to go be an entrepreneur.” He’s like, “no, get a stable job, right?”

Gary: Education was the way out. Right?

Jay: Exactly.

Gary: I was born in the Soviet Union, so obviously a different version of communism especially in the seventies. Obviously, I think for people that have parents or grandparents that grew up in communist Asia, they can relate much more to the mighty American contemporaries. We got out there luckily in the late seventies when I was a kid. We came to America. We were super poor. My parents are very much my heroes. They built their American dream. My dad used drive from Queens to New Jersey to get paid two bucks an hour to be a stock boy in a liquor store. It was very much that kind of a thing. I was entrepreneur from the get … you know lemonade stands, baseball cards, that kind of stuff. When I was 10, 11, 12, I was making hundreds of dollars if not thousands of dollars a weekend selling baseball cards in the malls in New Jersey. So I kind of knew I had it from a very, very, very young age.

Probably if you look at the graph, as soon as I knew I had, fourth grade was right around the time my grades started to slip. I was just very self aware. I talk a lot about self awareness. I just knew who I was. You know I don’t talk about this a lot. I genuinely believed that my schooling career was going to be my last great vacation. I took advantage of it that way. I thought I could get a real headstart and be educated. I’m scared to think what I would have looked like if the internet was around. Forget about graduating college, or even high school, I’m not sure I would have graduated grammar school.

My dad dragged me to the liquor store when I was 14 that he now owned. I fell in love with wine collecting and the culture of wine. I thought I could build a big business in 1996. At 21 years old I launched one of the first eCommerce wine businesses in America. From 1998 to 2003, in that five year window I grew my dad’s business from a three to a sixty million dollar business using modern digital tactics, email marketing, eCommerce itself at the time, Good AdWords, blogger outreach. The YouTube came along and I started a wine show. That was right around the time Twitter and Facebook were doing their thing as well. I used those platforms to build my brand, and became an investor in Facebook, Twitter, and Tumble blew up on the social media scene, the Web 2.0 as it was originally called. I was one of the 25 most followed people on Twitter in the early days. My career took a big turn so I …

Jay: Right, so …

Gary: Go ahead.

Jay: So when you were 14 though your dad dragged you into the wine business. That must have been kind of like, “Dad, I’m trying to hustle. I’m trying to be an entrepreneur here. Why are you doing this to me?”

Gary: Yeah. You know what? When you’re 14, and I think a lot of people know this, like I’m sure that crossed my mind but there was just no debating or negotiating with immigrant parents. Right?

Jay: That’s true, that’s true, very true.

Gary: For a lot of people that was get good grades, and there was no where to go. My parents punished, my mom punished me for bad grades but she quietly created an interesting framework of what I would call light lines in the sand, moveable lines in the sand. She didn’t want me to be disrespectful or completely pumped in and become a degenerate. She absolutely gave me the freedom to do my thing. It’s funny, I just dug up my report card. In my entire high school career, I got four A’s, all in gym. I was far from a scholar. I think that it was tough. I went from being my own boss making $800.00 a weekend, $1400.00 a weekend to making $30.00 a weekend, bagging ice for 15 hours a day in a liquor store. At the same token, I just kind of wanted to support my family’s thing, and was willing to pay my dues, and was thankful for my parents for coming to this country. Even at that age knew what they did was special and wanted to support our thing.

Jay: Right. It was kind of like, “Okay, fine. You dragged me in the family business. I’m still an entrepreneur, watch this. Watch what I’m going to do with the family business, and then I’m going to go and take off.”

Gary: Yes. When I realized that I didn’t want to sell beer and liquor, but when I realized there was a culture around wine and wine collecting, I saw the storytelling, I saw the creativity. I saw the marketing and I really ran with that.

Jay: Yeah. That’s awesome. Here’s a funny story Gary, I actually found you back in ’08, ’09 on Youtube. My girlfriend, who’s my wife now, girlfriend at the time, her mom is a big wine person. I was kind of surfing around and I was like …

Gary: Trying to impress?

Jay: Exactly, trying to express and I stumbled upon your Youtube channel. I was like, “Wow, this guy’s interesting because he’s actually …” I saw the one where you in like a half an hour you do like a how to expand your pallet.

Gary: Yes.

Jay: Awesome episode. I was like, “This guy’s actually …”

Gary: By the way, the episode that put me on the map, and I don’t remember, I think it’s episode 174 or something like that. Talk about patience, nobody was watching the show. That episode where I taste all those different flavors at the supermarket, and Twizzlers, and dirt, and flowers as you saw.

Jay: Yes, that’s the one.

Gary: That episode made the front page of Digg, which as you know there was no bigger get in 2008 on the web that getting on the front page of Digg. That made a lot of people aware of me. That started Kevin Rose becoming aware of me, which helped me get on Diggnation, his blog, which helped me spike aggressively in the Twitter following count, so a very, very important episode creatively for me.

Jay: That was amazing. So you went from that and then I actually lost track of you.

Gary: It makes sense.

Jay: Yes. Then boom, five years later you are everywhere, so an unbelievable assent.

Gary: Thank you.

Jay: I read Crush It, maybe a couple years after that, which by the way changed my life as well. I’m sure you hear that all the time, awesome book.

Gary: You know it’s funny, I’m putting the pieces together to write a book called Crushed It. So, if it didn’t change your life, I’d love for you to send me an email in detail. I’m going to write an updated version of it, how to build personal brand in this new environment and why the opportunity’s greater than ever. I also want to feature 30, 40, 50, 70 people who actually read the book and have tangible results happen.

Jay: Yep. I will absolutely do that.

Gary: Please, please.

Jay: Yeah, awesome. So you go from there and now you’re an investor. Are you running a multi, multi million dollar digital marketing agency. You have obviously, you still have your wine business running. How do you manage? You obviously have a huge team now as well. How do you manage to stay current and have your hands basically in everything?

Gary: By realizing there’s no option. Right? I’ve made my bed now I have to sleep in it. I positioned myself as the guy who’s going to know what Marco Polo is, or [Bozze-ically 00:08:48], or Snapchat is. So kind of suffocating myself, calling my bluff. I just have to give something else up to stay current. Having a venture firm, you know I’m about to close my next one called Vayner Capital. I’m seeing stuff that helps. The Intermedia is almost an 800 person firm in five offices, a hundred million revenue business. There’s a lot of innovation and thought and staying current happening through there, including that we’re now doing a significant amount of work with the platforms. We understand where Snapchat, and Instagram, and Facebook are going sometimes before the media or the rest of the market as a partner, so that doesn’t hurt.

You know what’s funny? You know what the real answer is? Because I want to. How do I stay current? Because I want to. Like when you want to do anything, you figure it out. You’re giving up something else because I’m not watching this, or playing that, or meeting this, or doing that. So I do what I want to. I want to watch the New York Jets every weekend, and so I do that. That takes out of family time. It takes out of business time but that’s my escapism. That’s my release point. I want to see my family more and so now starting this fall, I’ve cut out Friday nights, which used to be very, very effective for me. It was a place where I’d get four to six hours of meetings that I couldn’t fit in the rest of the week gone. That will mean less business results because I want to see Meisha, Zander, and Lizzy more. It’s choices, right? How am I current and how am I at the forefront? Because I want to be.

Jay: Right. So let’s talk about entrepreneurship and entrepreneurs. You are a born entrepreneur. That’s just in your blood, in your DNA. Some people are like that. Can entrepreneurs …

Gary: Can you pull up a little bit?

Jay: … be made so to speak?

Gary: I’m sorry, I lost you there for a second. You said, “I’m a born entrepreneur.”

Jay: You’re a born entrepreneur.

Gary: Yeah.

Jay: Not all entrepreneurs are born like you.

Gary: Right. By the way, not all basketball players are born LeBron, and Carmelo and Durant. Right? I definitely believe that I was gifted more on entrepreneurial upside than most people, no question. I mean, I just don’t know what else to say. I mean I know it. It’s always been there. It’s not ego, it’s 35 years of history. I sold more lemonade than everybody. I made more money on baseball cards than everybody. I built a bigger liquor store than everybody. I built a personal brand bigger than most. I’ve in four minutes built one of the biggest social digital agencies and in the most competitive space. I’ve done it, so yeah I’ve got it. By the way, that doesn’t mean that for example than I’m in much better shape than I as 24 months ago. I’m nowhere close to highly ranked in the physical specimens of the world. I am dramatically better than I was 30 months ago, and that’s how I think about it. Right?

Jay: Right.

Gary: Everybody’s got a cap. I think my cap’s multi billions. I think other people’s caps are several hundreds of thousands. If that’s better than having a job and not being as happy making 87 or let me through you for a real loop, for people that are listening, people making a 187,000.00 a year as an executive and not being that happy, or making a buck twenty-seven as an entrepreneur and being super happy. That’s an interesting debate. It’s super easy when you make more money. What’s the happiness line versus the money line? I think all of us have different lines. I leave lots of money on the table for happiness every day, and other people do as well. So yes, I do not think that all entrepreneurs are built equal.

I do think that I was gifted with talent, but that’s the truth in everything. Fashion designers, cooks, Beyonce was born with more singing talent than me. Can I be a better singer than I am today? I sure can after three years of singing lessons. I think I’ll be borderline below average, but that’s a hell of a lot better than atrocious.

Jay: Right. So I love when you talk about your fitness because I watched some of your transformation in the last two years. I’m kind of into fitness industry myself. I do some coaching on the side.

Gary: Yes.

Jay: I always joke because I think that you have a mini fitness accelerator going on when you probably don’t even know it. I see these guys, Roman, and Mike [Mcanty 00:13:08], everyone that basically trains you, ends up going through and being successful, so it’s awesome to see that.

Gary: Well it’s true. I’m doing it with Jordan now. Listen, when you’re very close to being a filter, you know how they roll. They’re full time, they’re with me all the time. You can’t help but help pick up on habits. Like all the sudden Jordan is really killing it on Facebook video, which is helping his business. By the way, their successes are a reminder to me that I’m on the right path. Right?

Jay: Right.

Gary: I’m looking at them black and white. I’m watching their growth and it’s completely predicated on the tactics. It’s the religion and the tactics. It’s the strategy and the tactics. It’s the clouds and the dirt of hanging out with me. It’s philosophical.

Jay: I want to talk about real quick the state of entrepreneurship right now. I see … You’ve talked about this in the past, too. There’s a lot of weird stuff going on in the online space. The current state of affairs, online businesses. What are you most afraid of right now when you see these guys on Instagram flashing dollars and actually making money off of it? Will there be a day of reckoning, or is this something that we just have to deal with and that’s part of … Are they quote on quote entrepreneurs, as well?

Gary: Yeah. That’s been part of society. Selling get rich quick schemes and all the way down to versions of it that don’t seem as bad but in essence are still selling the same core philosophy have been around from the moment of time. I’m sure there was a guy who was like, “Hey, Caveman Rick. There’s a bunch of rocks over that hill. Give me four bucks, or excuse me, give me fir, and I’ll take you there.” I mean, unfortunately, there’s a lot of different DNA traits in the world.

There’s people that are posting tons of pictures of watches and airplanes and their description is, “I can help you make a thousand dollars a day. Click here.” That’s going to happen forever, right? That’s going to happen forever. Very honestly, that crew is really not happy with me right now. I’ve been noticing more negative comments about me from millionaire, billionaire, shmillionaire handles on Insta, and that means I’m having impact. I’m actually happy about that.

Jay: Right. You always talk about being real, and I feel like there has to be some sort of day of reckoning. I mean, maybe not-

Gary: Let me tell you where the day of reckoning is. The day of reckoning is when the person that’s making that money lives their lives, and their conscious or their grandkids calling them out and saying you weren’t authentic in the way you made your money, or a million different things that happened or them getting screwed by somebody in a bigger game. They didn’t understand they made a million on being kind of [inaudible 00:02:20] on Instagram, but then a financial advisor posed them out of their money. Do you know what I mean?

Jay: Right, right, right.

Gary: By the way, there’s people that live, scam it out, get all the way to the finish line, die happy. Money, power. I don’t know, man. I could never … How you make your money is more important than how much you make and more importantly, here’s what I know. The day of reckoning for them in happening every day. It’s the way that people view them in the world, and whether it’s talked about or not, they want to be on that pedestal. They may have the money of that pedestal, but nobody’s going to respect somebody who made a million dollars in a skeezy, kind of low-ball way, the same way they’re going to respect somebody who made a million dollars the right way.

By the way, a lot of people say, “I don’t care.” The truth is, that’s right. You don’t care when you’re climbing your way to make that money. You do care when you get there. I’ve met all of them, and they start worrying about why they aren’t on the cover of magazines. Why are they not respected? Why don’t they know Zucks? Why doesn’t the A-list hang with them? Why do people whisper behind their backs? Why are people not really inviting them to the cool shit? Why do they have to keep finding the next sucker? It gets exhausting. You become the 48 year old dude going to the bar trying to get 20 year old chicks.

Jay: Yeah. Totally. Okay. Garry, you are very good at observing people and seeing trends form, and some even call you a predictor of sorts. Youtube, Twitter, Tumblr, Facebook, what have you. In the last year or so, I know you’ve made a huge push. Snapchat, Facebook Live. You always talk about intention. Where is the intention going to be? Why don’t you tell us where you think the intention will be in 2017?

Gary: I think much of the same because remember, I don’t predict. I don’t know. I think Snapchat will continue to do well. I think Instagram will continue to do well. I think Facebook will continue to do well. I think Twitter will continue to struggle. I think that musically we’ll continue to grow. Obviously in Asia, it’s different with the We Chat or things of that nature, but I think that in the US market, We Chat got such scale and obviously had different dynamics than a full pledge, Silicon Valley capitalistic system that allowed it to scale and have that kind of monopoly.

In the US, you don’t have that scenario. Tomorrow something may pop up and take the attention. Tumblr and Pinterest aren’t as good as they were three years ago. They used to be top of my tongue. They no longer are. Now Snapchat kind of takes that role. Going way back, Uscream used to have that. Youtube still has it. Then you just never know. Marco Polo is an app that caught my attention, but Yik Yak was important to me for 45 minutes. I mean, the truth is, to me it’s of that day. I don’t know, but I do … People always say to me, “Gary, you always talk.” Sometimes people want to consume my content. They’re like, “Gary, you don’t talk about stuff, like I want the details. Rah, rah me, but I want full details.” I’m like, “Gosh, I’m the easiest to get details from.” Just watch what I’m doing. Out of everybody, I think I’m the easiest to get value from because my actions. Watch.

Jay: You also … Just your books alone and your Youtube channel. I mean, you go really deep under the hood with those. Aspect Gary V and Jab Jab Jab Right Hook.

Gary: What happens is somebody will follow my Instagram channel where my strategy is a little bit more quick, creative, rah, rah, and I’m like, “My God, nobody does anything like ask Gary V with that detail.” More importantly, I’ll never trump watching me ever. I don’t mean daily V, which we curate and create into something that’s entertainment and context. No, no. I mean me. Watch me reply to people. Watch what I post. Watch how I post. How often do I post? Why am I linking my Musically on my Instagram? Why do I mainly reply on Twitter but not post content? Why do I repeat my content on Twitter eight times a day or three times a day? I know that people aren’t seeing it. Watch me. Why do I email once a week? Why do I have a Youtube show? Why am I 90% Facebook video? Watch me. I just love that they’re like, “Well, give me details.” I’m like, “Details? Watch me. It’s the most free thing of all time.” Wait, you’re going to pay for an 800 dollar e-book that claims details, you idiot?

Jay: All right. Gary, have you ever been to Hong Kong before?

Gary: I haven’t. I’ve spend no time in Asia, and I think it’s … Like I said, it’s been building this kind of crescendo in my own mind of going big and going … I’ve got an Apple TV show that’s coming later in April next year that I know will maybe be the right building block to launch my … If I go, I’m going to go hard. I’m going to go to Asia. I’m going to go for two weeks. I’m going to do 9,700 things. I’m really excited about it. I’ve started converting some of my content into Mandarin. It’s very, very top of mind, but I haven’t done it yet. That’s why … You know what’s funny about me? I don’t talk about it. The reason you don’t hear me talk about it a lot is I don’t want to talk that I’m going to do it. When I do it, then I’ll talk about it.

Jay: Yeah. I think you’ve taken a right approach because a lot of companies come into Asia and China and they think that they can just steam roll their way in.

Gary: Impossible.

Jay: You know what? They’re out of business [crosstalk 00:08:00].

Gary: Impossible. Impossible. I was born in Russia. I know how business is done in Russia. I know how business is done in different cultures. I know how business is done in Tennessee versus New York. The [inaudible 00:08:12] for the culture and the context and the angles and the relationships is … There’s so much audacity, especially American business people, and I just will not take that approach. I’ll be very calculated, very patient, very empathetic, very respectful, and most of all, I’m going to repeat it again. Outrageously patient.

Jay: Yeah. Love that. Okay. We’re going to look to wrap up. I know we’re a little short on time, but listen, I want to ask you. You talk about a lot of things. Self awareness, hustle, gratitude. You hate negativity. You’re really popular guide talks about passion. You’ve gone on the record saying that you hate complaining.

Gary: Yes.

Jay: What is the single most important, if this is even possible to answer, the single most important trait to become a successful entrepreneur?

Gary: Self awareness.

Jay: Above all else?

Gary: Above all else. Yep. Once you know who you are, if you accept it, which I guess is in itself a definition of self awareness, you can roll. I mean, I wish I was a lot of things. I wish, but I’m not. Because I’m self aware, that’s the seed that makes everything else … I don’t complain a lot because I’m happy because things are going well because I was self aware and I don’t put myself in a position to not succeed. I mean, I’m self aware about the things that I do. Trying to bite off more than I can chew, extending myself, but I’m willing to pay the casualties or the toll for those inefficiencies and those shortcomings. Above all else, self awareness. Above all else, man.

Jay: Got it.

Gary: You’re allowed to the maximize your natural abilities and talents. Man, above all else.

Jay: Awesome.

Gary: Awesome.

Jay: All right.

Gary: Thank you.

Jay: Awesome. Thanks, man. You are everywhere. I mean, literally every social media channel your [inaudible 00:10:08] is on. Tell my listeners where the best place is to find you, and if there’s any specific place that you want their attention to be when they see this.

Gary: At the end of the day, it comes down to wherever they consume the most of wherever is most convenient for them. Obviously for people that are deeply entrenched in, let’s say, a China social ecosystem, I’m not there yet in a meaningful way, but outside of that, I’m pretty much everywhere. Whatever works for them. If they’re on Facebook, Twitter, Instagram, Snapchat, Youtube, you can find me.

Jay: Awesome. We’ll get that all linked up.

Gary: All right, brother.

Jay: Listen, Gary. Thanks so much for being on, man.

Gary: Thanks so much. Stay well. Bye bye.

Jay: Yep.