#67, Gary Vaynerchuk, Serial Entrepreneur and Chairman of VaynerX — The importance of kind candor, how to get over your insecurity, and why you need to embrace social media

Welcome back. This is from Startup to Grown Up. My name is Alyssa Cohn and today I'm talking to the one and only Gary Vaynerchuk. Gary is a serial entrepreneur, the chairman of Vaynerx, and a five time New York Times bestselling author. I think all you need to know about Gary is that when he was 6, he didn't open a lemonade stand. He got the kids in the neighborhood together and he opened a lemonade franchise. Entrepreneurial out of the womb is how Gary describes himself. And we talk about the contrast of his experiences between school and his experiences in business. Gary and I discuss how he gained his keen and delicate understanding of the here and now, especially when consumer trends and marketing channels move so quickly. In his new book, Day Trading Attention, Gary gets into the weeds about how you can understand your business and get attention for it. And Gary and I talk about why getting attention these days is so challenging and what to do about it. We talk about storytelling and the keys to telling great stories, why he's so polarizing and why Gary actually prefers to lose than to win. Gary shares how he keeps his energy up and the keys to not burning out. You're going to love this punchy discussion, so please enjoy my great conversation with Gary Vaynerchuk. Gary, it's so great to have you. I'm so excited to talk to you about your life as an entrepreneur in your new book. And Gary, I want to start with your youth. You didn't have a lemonade stand. You, the lemonade franchise. Tell us about that at six years old, a little franchise on your little big wheel.

You know, I think ambition is a, is a natural trait to some and clearly that happened for me. I mean, I don't even really know why it felt natural to ask Marissa Byrd and Eric Godfrey and my sister Liz and Robbie Turnick to divide and conquer the neighborhood and have more than one lemonade stand. But it was, yeah, it was just incredibly entrepreneurial, really out the, out the womb as they say. I as soon as I basically learned how to speak English because obviously I was born in the USSR and when I moved to Edison, New Jersey when I was six, it just kind of, it was the beginning. And you know, growing up in that, you know, quintessential 80s neighborhood, you know, just I was so fortunate. I lived in a cul de sac. Like just there was kids my age that naturally lived by me. I really got very fortunate and it was a tremendous upbringing.

Yeah, well, that's really fantastic. And obviously, as you said, entrepreneurial out of the womb. Also, I would just say you've been a very successful entrepreneur for decades and constantly reinventing yourself and what you're up to. I think people call you a futurist, and I think what you've said and I think I've observed that you really have a keen sense of present. And how did you learn that skill?

I think I learned it through the two core things I did in my youth, which were trading baseball cards and selling wine. And so from the age of 11 to 17, my great passion was trading cards. And in the 80s and early 90s, the way that world worked was there was a monthly price guide called the Beckett Price Guide. And it would come in, out every month, and it would show you what goes up and what went down. And then it was also sports. So new kids were getting drafted every year, Players were getting injured, players were emerging, superstardom. And so I got very comfortable with, like, paying attention to the now. You know, like, who's playing good baseball now? Who you know, right now, Larry Bird and Magic Johnson are the most popular, and Isaiah Thomas, but this Michael Jordan guy feels like he's coming. And then in the wine business, I started working my dad's store when I was 14. I started reading the Wine Spectator when I was 15, and by the time I was 17 or 18, that became my new obsession. And I would wait for the monthly Wine Spectator to come out, and the Wine Spectator would rate wines. And so a wine would get 90 points or 91 points or 95 points, and there would be a direct correlation to its score and how well it sold or how much people would ask for it. And so what happened there was I was like, really, again, had to pay attention to the now and, you know, was like, okay, Napa Valley wines are getting more popular, and French wines have always been popular, but wait a minute, Rhone wines, not just Bordeaux, are getting popular. So basically my entire training as an entrepreneur was in these markets that moved very fast, that people's consumer trends changed. People would want or not want something anymore based on actually a third party, arbitrary reviewer. And it just got me very focused. And then if you go Back to the Levan 8 stand, the baseball cards, and the liquor store, everything was about signs for me. And so attention became another thing that I paid a lot of attention to. So the reason I had a lemonade franchise was I was the one making the signs and walking around town looking to where to put the signs at baseball card shows. I would be watching people's eyes and see, even back to, like, how I think about book covers, what makes people stop, what's recognizable, how do I get them to pay attention. And you know, I really, really, really got those two things down. Speed of market changes and attention. And that helped me launch a website in 1996. Seven for wine library. And it's how I made signs in the liquor store and how I changed displays and how I got into ui, UX and ultimately kind of what I became most known for. It really helped me investing in early stage startups like right above my head here. This is Facebook, Twitter and Tumblr. Stocks that I bought before people knew what it was. Yeah, you know, this, this fashion brand, Siegelman Stables. Even more recently, like I could just tell it was starting to happen because I pay attention. It's funny, I'm such a talker and it's always disguised what I think is my biggest asset, which is, man, do I listen.

Yes, that's fascinating. And I love also the through line between lemonade and baseball cards and wine. And what advice do you have for people right now? Because people are sort of just trying to figure out what's going on in this fast paced world of change right now. What advice do you have for people to get more tuned into the present and be a better listener? Like you just said, like you just said.

There's a lot to it. I think, you know, first of all, I think all of this for every entrepreneur listening, it's about self awareness. You know, if when people ask me like, what's the starting point? You know, the starting point is self awareness. Like, do you know yourself? I think too many people are obsessed with wishing they were something versus focusing on what they are. And that doesn't mean don't push yourself and try new things. It just means delusion is a bad business strategy. And so, you know, not everyone's cut out to be a salesman or an artist or a project manager or a product designer. Like, you've got to have a sense of who you are. So my biggest advice to everyone is what are you passionate about? Because I think if you don't have passion, it's very hard to sustain the amount of work that is required to actually build an entrepreneurial success. I think that's disproportionately the biggest issue at hand. I don't think people understand what they're signing up for. With entrepreneurship, it is a constant game of losing with occasional wins. That is so well said, you know, and I don't think people understand. It's, it's kind of like boxing. Like you're constantly getting punched, you're trying to punch back, but you're definitely constantly getting punched, constantly trying to dodge punches. And occasionally you get knocked down and hopefully you get up and occasionally you knock something out. And so, you know, I don't think people have the intestinal fortitude or stomach for it. And I think the only way you can actually do it is to enjoy it. Like when I look at my schedule, when I think about my days, when I think about how hard it is, it makes me think about people that can go to the gym for two hours and really go hard at it. That doesn't come natural to me. I don't like that. I do it because I want to be healthy and I want to live longer and all those things, but it is not enjoyable to me. It does not come natural. On the flip side, doing a 12 hour straight entrepreneurial day with 65 meetings, 30% of which are headaches, 50% of them which are mundane, and I've got to get through it. That takes a level of enjoyment of the grind. And I think that the reason people burn out is not because they're putting in too many hours, it's because they don't enjoy it and they're anxious.

So true. And that stress is getting to them. Yeah. So you gotta kind of enjoy the journey.

By the way, I burnt out in school by fourth grade. I quit because I didn't enjoy it and I was anxious. I didn't enjoy the negative feedback. I didn't like the process, I didn't believe in it and I struggled with it. And you know, I lived my entire childhood grinning and bearing with Monday through Friday. And I feel very empathetic and sympathetic for people that hate their jobs or their entrepreneurial ventures because I couldn't imagine living for the weekends like I used to.

I think it's so significant what you're saying. The idea of self awareness and also just really being honest with yourself about what's going on with you and recognizing what the sweet spot is. Honestly, the way we can all work hard is to love the journey. If you love what you do, you can put more time and energy into it. One thing that want to just double click, go ahead.

I can feel people on the other side kind of glossing over what the way you just recap that. My friends, please listen. If you do not like it, it will not work. Like if you're doing a business for the money. One of the biggest reasons that people fail is they chase the current hot thing. They're into crypto Then they're into cannabis, then they're into real estate, then they're into AI and they're chasing money and chasing the short term money is the number one strategy that makes people fail. And so before we move on, I just want you to, it's not a hokey thing to say. You have to enjoy the journey. It's the only sustainable thing.

So one thing that you're really talking about now is of course this attention which we already talked about is the roots of it at age 6. And your new book is called Day Trading Attention. What? Tell us about this book. Yeah, there you go. I love it. Day Trading Attention. Everyone should go get it. What do you mean by Day Trading attention? What is the title about and what's the book about?

The book is probably my most significant textbook that I've ever written, meaning it is incredibly detailed by comparison to many of my books. I wrote a book 10 years ago called Jab jab jab right hook that was very successful and it really broke down individual pieces of social media to help people learn how to be better at social media. I would call this the 301 course to that 101 course. So, you know, I don't know if you had a chance to skim it or.

Oh yeah, I read it.

So you read it.

So I read it. Very extremely practical, everybody. Very practical, tactical in the best way, like uncomfortably like.

And so textbook that when I read the audiobook, did the recording for the audiobook, full transparency. There was times where I was born bored because I'm not that kind of learner. Plus I obviously already knew the subject matter, but this is like Nerd City usa. There's, there's charts, there's, it's a, you know, actually let's flip this on its head. You, you do this for a living?

Yeah.

You're around the business and marketing and world. What most stood out for you in.

The book, what most stood out for me was that there's different strategies for different things and you have to really think what's to be relevant for your audience and what's going to work for you. And then the other piece that really stood out was you are not allowed to opt out of the ways to get attention. If you're an entrepreneur, if you want to be successful, you need to get attention and you'd be like, oh, that's not good for me or I don't like that. I'm not like that. You have to kind of get over your discomfort and try new things.

This goes back to the gym. I don't want to go to the gym and I don't want to eat clean. But if I don't, I won't live as long or as healthy.

100%.

I get that people may not want to do social media. People have political points of view on social media. People have emotional points of view on social media. But let me make this very clear to everyone who's listening or reading. If you do not build awareness and relevance on social media, your business is in trouble. And you can snicker and scoff because your business is doing well right now and you're not doing social. But that's because you're looking at yesterday and not tomorrow. Every day that goes by, there are people out flanking you on gathering attention, which is the only asset that leads to action. Nothing can happen. You can't vote for someone. You can't marry someone. You can't choose to go to a restaurant. You can't buy a sneaker. You can't decide to like a sports team. There's nothing that happens on earth that doesn't start with the attention. You have attention. Your grandfather can't instill wisdom in you if you're not listening to him. Nothing starts without attention. And attention now sits on these 7 to 10 social networks at such a high propensity. And because we're living through the TikTok ification of social media, everyone listening or reading has the potential to start the process of gaining meaningful attention that can lead to them selling something, building something, or it doesn't have to be capitalistic or selfish. It can be incredibly selfless and altruistic. You can raise money for your nonprofit. You can help or be the person running for local mayor. You can raise money for the pta. You can bring awareness to a family in need. So attention is everything. And the reason I say day trading is the way attention used to work was slower. You would plan months of a television ad. You would sit in boardrooms forever on your strategy. It would be more like investing long term in a mutual fund. You'd meet with your financial advisor for a long time and make a decision and buy it and go to sleep. Now it's like day trading. If you don't know what's happening on these algorithms on these social media platforms, what's happening in pop culture, you're finished. And. And that's what's happening. And I look, I wish it wasn't happening either. I had figured out direct mail. I knew how to run newspaper ads in the Star Ledger. I knew how to run local television commercials on Comcast. I had figured out search. I figured out email marketing. I'd figured out the first version of social media with YouTube and Facebook and Instagram. I mean, in Twitter. Excuse me. I don't want it to move either. It's hard when it moves, but tough luck. This is business.

Yeah, 100%. And you have to make peace with reality. And I think also what you're also talking about is that the upside of that is that the barriers are much lower for anyone to start a brand and to create relevance. And one thing you talk about a lot in your work and in this book is the power of storytelling. Can you talk about storytelling? Why that's so powerful? And also, again, advice to people who would say, oh, I'm not great at storytelling. What. What do you thought? What are your thoughts about that?

You know, I think storytelling is just about authenticity in a lot of ways. Like, obviously, some people have a gift of gab, right? And so I'm, you know, I'm aware that it comes more natural to me, and I'm. I can get people more excited because the way I put together words and think about it works. I get that. However, it's. First of all, it's not an energy thing. Like, I may be hyper and excitable, but they're incredible storytellers who are incredibly, you know, straight, mundane, calming. Everybody has a different way of. Like, many people don't like my content because it. It makes them anxious. It's too much. I understand that some people like the sound of the ocean. I want to sleep in New York City. Everybody gets that. But I think it's that people are not authentic. And what I mean by that is some people look at me and they're like, oh, that's what I want to be. They themselves are not high energy, and they try to force it, and the audience can feel it. About authentic is. I don't think people talk about the things they know or they love enough. One of the reasons everything works for me is when I'm on stage, when I do an interview like this, when I make content, I'm speaking from passion and my heart and my knowledge. Why do I mainly talk about business or wine or the jets or the Knicks or garage sailing sports? You know, it's pop culture. It's because what I. It's what I know. And I think too many people aren't talking about things they're knowledgeable about or things they're passionate about. And I think that makes them very vulnerable to be Bad storytellers. They're trying to talk about things that they don't care about or know about. And I think.

Yeah, I think that's true. I think people also don't know what a good story is. You know, they sort of think like something happened to them and it's not going to make a good story. And I think people won't sort of just take the risk to express themselves and put themselves out there. Do you find that?

Yeah, I mean, I think, I think that's what I, you know, look, I think this goes back to how we started the show. Like self awareness, like self love, like eliminating insecurity. People value other people. Most people are good storytellers because they're scared that people will judge their story.

Right.

I'm right. Think about some of the things I've said in this interview. I understand why someone might not like my content. I am self aware and realize that I have a certain style and a very distinct style which obviously works quite well for me with certain people. But when, I mean, there's people, people are very funny. I'll be in an airport and for every 99 people that come up to me and ask for a selfie or say something nice, which is like just the most humbling experience that I could go through one of 300 times, some people literally come up to me and say, I don't like your stuff. I'm like, I'm sorry, you know, and, and it's funny. It's, you know, I, I really don't struggle with that. And I really, I actually just reenacted what normally happens. I'm very quick to apologize. I'm like, you know, I get it. Like, you know, I don't, you know, if I'm in a funny mood, I'm like, well, I don't like your sweater. And like, you do, you know, like, if I'm in a more serious mood, I'm like, look, I get it. Like, maybe it's too jersey. The cursing, the cursing. You know, I curse maybe that. You know, I also poke very hard at things I don't believe in. If you are. For example, this happened three months ago. Somebody that works in selling television ads came up to me. It was kind of nasty and I diffused it. And very quickly we got to the punchline. Like, I get that if you believe television commercials are the best in the world, I could be a really tough adversary. I am constantly publicly crapping on anyone who buys a television ad for the cost that's associated with it. And so I Understand that. Just like when I see someone wearing a Patriots hat, as a die hard jets fan, I don't like them either.

But it's. I'm from Boston originally.

This interview is over.

Bad things have happened.

I mean, look, at least we're doing. Hopefully our Knicks and Celtics make it to the Eastern Conference finals and then the bad blood will really start.

Exactly. And then we can duke it out. Gary, how have you changed personally as you've grown as an entrepreneur, as a leader?

A lot? I think I, I really was able to finally face my vulnerability and my shortcoming, which was, believe it or not, this is wild. As a public figure, my biggest strength is candor. As a private business owner, my inability to be candorous to my employees because I liked them too much and I was scared I was going to scare them by giving them critical feedback was disproportionately my shortcoming. As a leader. All, all that I was doing was creating resentment, passive aggressive behavior on my end, resentment towards people, which was hurting me, passive aggressiveness with little zings which was hurting them, and very sloppy firings which hurts me and them. And so it was, it was a very tough 20 year journey for me from 22 to 42 in having. That was my, that was my kryptonite, where I was gifted with so many talents. That was my kryptonite. So I would say by far the biggest thing that has grown is my ability to now give candor. I call it kind candor. I want to deliberate with compassion and sympathy and empathy, but it's a real thing. And you know, so that, that was real. You know, the gray hairs give you experience. So yes, I was a natural talent. But you know, when I look at LeBron James 20 years later in his career, he, he's still a physical specimen. There's things he can't do that he did in his youth, but boy, oh boy, oh boy, does he understand the game of basketball much more than he did at 18. And you know, I was very gifted as an entrepreneur, but I'm a dramatically more experienced operator and executive and decision maker. So, you know, wisdom of, you know, pattern recognition, right. The reps, you know, and, and the ability. I've always had the ability. Humility was a really powerful thing that my parents instilled in me, which is incredibly tough thing to balance with extreme confidence. But man, when I tell you, my confidence was always through the roof, but my humility was my equal match. Meaning, one of my favorite things about entrepreneurship is when I lose because I think it Allows me to not get, as the amazing poet once said, never get high on your own supply. And. And I, I feel like I'm very good at that. Like, I'm aware that I've had a lot of success. I'm aware that I get a lot of admiration. But, for example, this book. I'm aware that I've written five, six New York Times bestselling books, but it doesn't mean this one's going to be. And I think that level of humility and tenacity allowed me to potentially write my best book.

Well, you talk about confidence and humility, and so that brings me to imposter syndrome. A lot of entrepreneurs and successful people experience imposter imposter syndrome or severe self doubt. Have you ever experienced imposter syndrome or severe self doubt?

Not in a business environment. I think, you know, imposter syndrome is slang for insecurity. You know, I felt insecurity in swimming, in riding a bike. I was always fearful of, like, drowning or hurting my knee. So as a child, I had insecurities around common things. I was also, like, insecure or scared of, like, my first kiss. You know, like, like adolescent stuff I can really associate with insecurity. Right. As a business person, I was getting, you have to understand how my life worked out. I was getting D's and F's in school. So grown ups were giving me negative reinforcement. And this was the 80s and in New Jersey and blue collar New Jersey. So, you know, they all were well intended, but my teachers were not politically correct. I had teachers say that I was dumb, I was, you know, a loser, that I would grow up being a garbage man. And I was very fortunate because I was unable to listen to them. I did not absorb that. There was only two reasons. One, my mother was such a positive force of reinforcement at home that I thought I was the best. But she wasn't a modern parent where it was delusional. You're the best and no consequences. It was, you're the best, but if you do anything that's out of line, you're gonna really feel the wrath. And number two, the market. The market. When I was six, I sold the most lemonade. When I was 10, I sold the most baseball cards. When I was 15, 15, I was selling the most wine. And so the market was always telling me I was good. So I could never really have imposter syndrome in business, AKA insecurity, because it's always been a positive reinforcement. Plus, I love sports. So with a sports overlay, I knew that you don't win every time. One of the biggest issues in our society right now is eighth place trophies. You know, we, we demonize losing to children, thus rendering them to be scared of it. You know, and I think we've created losing as a boogeyman and now are scared to lose. I, I, I'm going to go very dark. I weirdly prefer to lose. Yeah, I like it. I like that feeling of my chemicals saying, okay, now let's figure it out and win next time.

Great. That's how you respond to it.

I love adversity. I love my back against the wall. I love being don't put baby in the corner. You know, like, I want to be doubted. I prefer to be booed. I would have been a great athlete on the road. I would have been a super villain. I would have adored everyone booing at me.

I love that. I love everyone should just right now take a little piece of wisdom around. I love being the underdog. I love being under adversity. And we can all really benefit from that. Gary, one last question. What do you wish you had known earlier on your journey?

You know, look, I really, I love my relationships and to know that there are people around Earth that worked directly with me. I basically judge my life based on how do the people closest to me view me. You know, especially now that I've lived a life where I have a public Persona and a public life, you know, I've had to really get comfortable with being judged without being known. And, you know, 85% of the time, it's wonderful. People put me on a pedestal. I don't think I even deserve. And then 15% of the time, it's challenging because no one wants to be hated or disliked. But for me, I love knowing that the people that know me best like me the most. There's only one very small group that that doesn't apply to that was the individuals that I was unable to be candorous with and then sloppily fired. So they don't view that I was upfront with them or that I was full of shit. And that bothers me tremendously. And so I wish I knew that candor was the vulnerability. I know we spoke on it earlier, but that's the truth. That's the answer to the question.

Gary, thank you for your time today and thanks for the contribution you made such a contribution to entrepreneurship over the decades. Thanks for listening to From Startup to Grown Up. If you like what you heard, give it a review on Apple podcast so other people can find it and if you know of a founder or someone else who is meant to be on this podcast, drop me me a line through my website alyssacone.com.