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This chapter means a lot to me because I think the topic of self-awareness doesn’t get enough attention. And yet, if there’s one thing that’s helped me win over the course of my career . . . well, I’ve said that about hustle and gratitude and all kinds of other traits discussed in this book, haven’t I? Whatever. This is another characteristic that has really worked for me. If I could sell a formula made up of gratitude, empathy, and self-awareness, it would be my billion-dollar coconut water idea.

My self-awareness is one of the reasons why I can comfortably say outlandish things and make hyperbolic statements. I know what people think of me, and I know that the same things that draw people to me turn others off and keep them away. I’m okay with that, because I think I can help more people and get my point across better when I’m my unfiltered self.

Knowing how you come across to others can often give you an advantage as an entrepreneur. Take sales, for example. You can set the tone in a scenario, anticipate how other people might react, and thus be prepared to address their concerns and questions even before they’ve been able to articulate them. It’s a really valuable tool to have in your communication tool belt, and it’s something I look for and admire in others.

Self-awareness is underestimated now, but I know someday when I’m in my fifties, sixties, or seventies, it will be the subject matter of the day. If there is a chapter in this book that you would read twice, I’d ask that this be it.

imageWhat are some easy ways to become more self-aware?

There’s one hack, and it’s asking people straight up to tell you your strengths and weaknesses. These people have to be the five to twelve people who know you the best or work with you the most. You have to create a safe zone within which they can do this, of course. No one is going to be honest with you if they think you’ll make them pay for it later or if they love you too much. You also have to be prepared for them to tell you things you may not want to hear or that you disagree with. That’s why you have to gather a diversity of opinion. If you hear enough people say the same thing, whether it’s that you’re too kind or too aggressive, you’ll eventually have to accept that it could be true. In fact, embrace the people who tell you you’re full of crap. Double down on those relationships, because they’re the ones that will help you improve the most.

Get yourself a thick skin. I hate reading bad stuff about me, but I can handle it. I respect it, accept it, understand it, and I try to learn from it. If you’re aggressive about getting the feedback, and man or woman enough to “eat it,” you can make changes in your interactions with people and your approach to business that can pay off in big ways.

imageWhat’s the most common mistake founders make when building a consumer-focused business?

There are so many goddamn mistakes, but the biggest is when they delude themselves into thinking they are significantly more talented and special than they really are.

No one wakes up and says “I’m going to be an NBA player today,” but everyone today—the young and hungry, and the old and hungry—is deciding on a whim that they’re going to be a consumer product innovator, start-up founder, or cofounder of a consumer product company. The audacity is ludicrous and stunning to me. People underestimate how hard it is to build a consumer app and create something sticky that people care about. It takes a special talent, yet career students, corporate people, and bright-eyed hustlers think somehow they’re going to understand consumer behavior and scratch that itch for a consumer product better than anyone else. So the mistake? Not having the self-awareness to know they’re not good enough to do it.

That said, if you can afford the risk, I say go ahead and try, just as I would tell anyone to try out for the Los Angeles Lakers if they allowed it.

imageIt’s good to understand our talents and weaknesses, but I fear we’ll get trapped into a mind-set of telling ourselves that there are things we can and can’t do. Poet Robert Browning said, “A man’s reach should exceed his grasp.” I want people to try lots and lots of things. I don’t want people to tell our children what they are and aren’t good at. How can you incorporate that idea into your discussion about self-awareness?

The person who asked this question, speaker and social media strategist Ted Rubin, was absolutely correct: People should reach high. But nothing I see in the market today indicates to me that people have a problem holding themselves back from trying whatever idea pops into their heads. Ideally, of course, people would blend a healthy sense of confidence with self-awareness. But I think we live in a culture that encourages us to believe we can be good at everything we set out to do, especially in the U.S. market.

Modern parents are telling little Stevie, “You can do anything you want!” Except Stevie sucks at basketball. They do the same for kids who want to be singers or engineers—or entrepreneurs. You’re just not always going to be able to do everything you want. I think it’s a good thing to remind people to evaluate their strengths and their weaknesses because not enough people are acknowledging they may have the latter.

Since not many people are willing to have that conversation, I think it’s okay for me to push that message out a little harder than I might otherwise, and not hedge with Ted’s valid point. I do the same thing when I bash TV advertising. It’s not that I don’t believe it has a purpose or value, but I don’t need to advocate for it because 99 percent of the market already does, and it is grossly overpriced. TV doesn’t need me. Self-awareness does.

What people don’t realize is that the process of forcing yourself to be self-aware requires drinking a sh@tload of humble Kool-Aid. It’s insane how much humility has been instilled into me by the market and has balanced my ego and self-esteem. I get why people think I’m full of myself, but what they’re seeing is the postgame of a long period during which I learned to stay away from what I’m not good at so that I only talk about the things that I know I’m better at than most people. Everything should be in balance, so when the market is leaning so strongly in the direction of “Everything Is Awesome!” I think there is an opportunity to talk about how some people need to understand they suck.

Now, here’s the thing. If you do suck but you love the thing you suck at, do it! If you love singing more than breathing, go for that singing career. I would just like it if you could go for it with the full realization that you’re most likely going to wait tables for your entire life. You can’t be disappointed if you go in with your eyes wide open. I’m not immune to FOMO, but I knew that to do what I do I’d have to leave a lot of fun and leisure on the table. You always pay a price for doing what you love. That’s just life.

imageDo you have any tips for presenting your consulting services to a potential client? PowerPoint? Video?

How should I know? Are you good at making a PowerPoint? Can you make a better video than anyone else? Or are you the kind of person who can just walk in and close the deal? Ask your business partners or employees, if you’re not self-aware enough to figure out for yourself what you’re good at.

This question is one I could never answer without knowing you well. What works for me doesn’t necessarily work for you. Look inside yourself (or get others to tell you what they see): The answer is predicated on your God-given ability or on the skill you’ve worked hardest to master. Many of you do so many things better than me it makes me want to vomit. There are sooooooooo many ways to present. Go with the one that lets you shine.

imageHow does humor play a role in business, if at all?

It does, and it plays the same role it plays in all of life—by easing tensions, greasing wheels, making people feel good. Wouldn’t you rather do business with someone who makes you laugh than with a stick in the mud? A gift for humor happens to be one of the most attractive personal traits, and maybe one of the rarest. Remember the outpouring of grief over Robin Williams’s death? People who can use humor to show us the world in a way we’d never have noticed on our own are special. I use humor inspired by stand-up comedy in my keynotes because I think it helps people remember (and enjoy) my talks more. I also use it to drive difficult HR conversations, and leverage it when I’m selling to clients.

As attractive as a sense of humor is, though, it’s no more important than the other ones people are attracted to: caring, empathy, self-awareness, kindness, and beauty, among others. But if you know you’ve got it, use it.

imageWhat was the biggest decision in your life that made you successful today?

It was the day I made the choice to suck at school.

Fourth grade. Mr. Mulnar’s science class. I got an F on a science test. To make sh@t worse, I had to get it signed by my mom. To avoid being punished, I hid it under my bed, where it sat for two days until my conscience got the better of me and I showed it to my mother.

Until that moment, though, I was in hell. I distinctly remember sitting in my small bedroom, crying and trying to make sense of why I was having such an intense reaction to this test. And then it hit me, the thought that changed everything:

“Screw school. I’m a businessman.”

I made the conscious decision to eat the pain four times a year when report cards came, to eat the pain of failing pretty much daily. Who cared if everyone thought I was a “loser,” a kid without a shot? I knew better. I saw something different. Even at that young age, I was self-aware enough to realize what I was born to do.

It’s not that I didn’t care. I went to every class. I was respectful to my teachers. I just decided that I would be better off honing my skills and concentrating on what made me happy and what fulfilled me. I learned about selling baseball cards, which then became wine, which became WineLibrary.com and VaynerMedia and everything that makes me so immensely proud.

That moment marked the first time that I decided to fight what society expected of me and deliver on what made me happy.

And you should, too. Bottom line: Stop doing things that make you unhappy. I’ve been preaching this since my first book came out, and long before that. Sure, it sucked to get those report cards every quarter, but sometimes you have to take a thousand punches before anything good happens. Not everyone will understand what you’re doing, and the more you work, the more chances you have to be disappointed. Or even to be the disappointment. But don’t let those moments fool you. An instance of failure could be a huge opportunity.

Pay attention. Learn to be self-aware. One F on a test got me started. Countless bad report cards got me going. And if I could go back, I would fail every single test all over again.

imageWhat was the toughest thing you’ve ever had to do for your career?

Historically, my answer has always been that it was leaving the Wine Library and starting my venture in VaynerMedia, but that’s not the whole story.

Truthfully, the toughest thing I’ve ever had to do professionally was decide that I was okay putting myself out there.

Many people have forgotten that the first ten to fifteen headlines ever written about me in the media were essentially all “Wine Wiz Kid Builds Business.” All of a sudden, all these entities I’d always had huge respect for, like the New York Times and the Wall Street Journal, were respecting me. It felt great.

But not long after that, I realized that there was a certain path I would need to take if I was going to get a bigger reach and gain a larger audience. And I was pretty sure there would be consequences. Sure enough, as soon as I started really letting people into my mind-set into business, not wine reviews, and communicated it in the way I do, people stopped talking about me as a great business operator—someone who made huge profits by realizing trends and executing on them—and instead described me as a “self-promoter,” a “social media guru,” and an “author.” In the eyes of those entities and people I’d always admired, I’d taken a step back (or two or three). There was a lot of eye rolling from “the establishment” that looked down on me for my self-promotion, as though it somehow undermined the success I had created until that point. It wasn’t easy to know that my choices would cause some people to dismiss me and everything I’d accomplished. In fact, it continues to be something I struggle with, because I really enjoy being respected, as does everyone, especially when you work so hard. On the other hand, in a weird way I like the fact that people’s prejudices against me cause them to underestimate me. In entrepreneurship, the truth is undefeated. Ultimately, if I execute multiple hundred-million-dollar businesses and make smart investments, it’s all “net-net.” You might not like that I don’t dress up, or that I curse onstage, or that I self-promote, but if I execute, you just have to “take it.” Once I was able to accept the fact that I was going to enhance my accomplishments and live at ease by being me, at the expense of the establishment’s respect, I was able to carry on and create everything I have today.

imageHow do I keep low self-confidence from keeping me from succeeding?

Self-esteem is the ultimate drug of our society. When you have it you give yourself the audacity to dream big, and when you do that, the little things stop mattering and anxiety cannot cripple you. I’m probably the least anxious person I know, even though you might think I should be, with all the responsibilities I carry on my shoulders. It’s just that I have such strong self-esteem. (Thank you, Mom, you are truly amazing.) I’m absolutely sure that I can handle whatever comes my way.

I wish I could give people who struggle with this issue a rah-rah “you can do it!” answer, because without self-esteem, I’m not sure they can. That said, if you are self-aware enough to know that you lack confidence, you could definitely execute to get more. You need to do research and think hard about what you can afford to do. A lot of people would probably benefit from seeing a therapist who could help them work through whatever is keeping their confidence down. At the very least, start working to surround yourself with confident, positive people. Be as determined to get that self-esteem as an addict jonesing for a hit.

imageA lot of small businesses fail because they refuse to accept when they’re not good at something and insist instead on doing it themselves. How would you suggest telling someone they need to stop?

It’s easy to know you need to outsource when you need A-level work and you’re an F. It’s a lot harder to see when you’re a B. Here’s the clue: If you try, try, and try but don’t get any better, hire someone who’s an A. There’s no point in wasting energy on that struggle when it could be better used to enhance things you’re already good at.

Now, let’s say you know someone who thinks he’s an A, or at least who thinks with enough practice he can become an A, but after a while it becomes clear that he clearly isn’t and won’t. Do you just let him flounder? I don’t think so. I say call him on it. I do this all the time. I’ll see a tweet and respond to tell the account holder how he or she could have done it better. I’m very polite and try to provide value.

imageDo you think it is necessary to have an outgoing personality to be a successful entrepreneur?

It’s never been less important.

Don’t believe me? Think about all the successful entrepreneurs whom people talk about every day. Zuckerberg. Evan Williams. Kevin Systrom. David Karp. If those names aren’t familiar to you, maybe you’ll recognize these: Facebook. Twitter. Tumblr. Pinterest. Instagram. Ringing some bells now? While I don’t know for sure they each identify as introverts, I do know they’re absolutely not the kind of people who outwardly self-promote by today’s Internet standards.

In the past, most of our connections were made through things like networking events or conferences. That setup made it absolutely necessary for young entrepreneurs to be outgoing and put themselves out there. And if they couldn’t, they often found it necessary to bring someone on board who could. But technology has changed the game, and now your first impression doesn’t have to be made face-to-face. You can shape your persona through your online interactions and presence. Meeting people in person is still important, but there are many other ways to build a company, talk to people, and make connections in the business world, all without leaving your desk. We are in the glory days of the introverted entrepreneur.

There is still plenty of room for the extroverted entrepreneur like myself, of course. And thank goodness for it, because I could never try to fake being someone I’m not. I’m very good at representing myself authentically online, but I know my strengths, and I know that I can get ten times more when I can meet people and bring my energy to the table face-to-face.

So introverted entrepreneurs, don’t fake it. Bet on your strengths. If you prefer to sit all day at your desk and focus, do that if it’s working for you. Never make the mistake of thinking that you need to be louder or more outgoing, or fake a bigger personality. This is a tremendous time for you to build a company. The ball is in your court, and social media and technology have put the whole game in your favor.

imageHow do I overcome my people-pleasing nature?

Why would you want to?

Society has long taught us that wanting to please people is a flaw and that it makes us weak. But it’s not a weakness; it’s a strength. I should know, I’ve built my entire world on it.

What is wrong with wanting to give? Being positive? Making sure everyone around you is happy? It blows my mind that people would want to label these as weaknesses, especially when I have seen firsthand how much ROI these actions offer when you use them to build a business. The only time people pleasing is a weakness is when you don’t know how to ask for something in return or you only do it to ask for something in return.

You can give, give, give all you want, but if you never step up and ask for something back, you’re not going to win. When you give someone something they need, when you make someone’s dream a reality, in a sense they owe you. Their gratitude will make them very open to doing something for you when the time comes. But you have to ask. Nothing will ever happen if you don’t just step up and ask for what you want, whether it’s a sale, a connection, or a reference.

It’s a tremendous personality trait to want to make others happy. Just don’t forget to look out for yourself.

imageYou get very personal when building your brand with the public. How personal is too personal? Where do you draw the line?

You draw the line where you feel you should. I like getting personal because I think it helps people feel closer to me, which helps me build my brand but also allows me to get to know my fans better. Getting personal is one of the reasons I love doing The #AskGaryVee Show so much. But I’ve got limits. I’m willing to put out a picture of me on the toilet, but I don’t share pictures or really any information about my children. Some people go nude; some won’t show their belly button. You’ve got to go with your gut. Also, remember that you’ve always got the right to change your mind. What might be too much last week might not be tomorrow, and vice versa.

imageWhat do you think is more important in business, IQ or EQ?

They’re both important, of course. I know my IQ is kind of average but that my EQ is off the charts, so that’s where I go all in. It’s been the foundation of my success and allows me to give back to my community, which gives me leverage. It allows me to form instant relationships, which is quite the advantage in my line of work.

I hear that a lot of people try to emulate me because my way looks fun and sizzly, but my way won’t work for you as well if you’re putting it on like a costume. You have to do you. There are plenty of people who love data, math, and tech and have happily made tons of money on their IQ. (I wish my math skills were as strong as AJ’s! They aren’t even close.) Whether you’re all EQ, all IQ, or like the majority of people a nice mix of both, the important thing is to be aware enough of your composition to capitalize on your natural gifts.

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