EXCLUSIVE: Gary Vaynerchuk on Business, Life and Building Human Empires

(Photo: GaryVaynerchuk.com) (Photo: GaryVaynerchuk.com)

Gary Vaynerchuk’s road from Wine Library to VaynerMedia has been well-chronicled—not least because he’s the one doing the chronicling, with an intensity and speed that has come to define him as one of the social media world’s stars. Best known for turning his family’s modest wine business into a powerhouse through the tools of digital marketing, he’s now doing the same for brands, with VaynerMedia booking clients as big as Pepsico and General Electric. He’s also, in the midst of all that, an author. We caught up with Gary on the occasion of the launch of his fourth book, #AskGaryVee: One Entrepreneur’s Take on Leadership, Social Media & Self-Awareness, to talk about the clouds, the dirt, and everything in between:

You’re one of the more prominent people in digital who also has decided to do long-form work, but four is a fair number of books, a lot for any author. People struggle to get even the first one done. Why a fourth book?

I wanted to make a 360 blueprint for the modern entrepreneur. I think I’ve hacked books in an interesting way: My view is that books are not that expensive; in fact, they’re actually quite cheap. I am not scared of writing a book that only lasts for two to three years, because I think for $20, that’s a good deal in the world for what you’re paying more. I’ve written more books because I write books like hyper blog posts. It’s current. It’s like an article. It’s like a keynote. The reason I’ve been able to produce quite a few is because I’m often talking about the state of the union of entrepreneurial journeys through the lens of the digital revolution.

I came off a textbook, Jab Jab Jab, Right Hook, which was so black and white, I didn’t even do an audiobook. And then The Thank You Economy in 2011 which was very philosophical. So it’s been a while since I wrote about the current state of entrepreneurship in a digital age, outside of, say, the content that I put out all the time. I talk about the moment of digital and entrepreneurship crossover and every two to three years there is so much going on that it’s worthy to reexamine.

The book opens with the analogy about how you operate in the clouds and in the dirt. Can you talk a little bit about that?

I think I win on extremities. I don’t play in the middle. And most people play in the middle. I have audacious, egotistical all-time legacy goals in my professional career and this is how I act on stage. I got this shtick, this ambition. I am on my second very large company that I’ve built in a short period of time. I’ve got bravado, and yet I will work today from 7 a.m. until 11:30 p.m. I want the dirt. I built my success by putting in the hard work. I think that too many people play some version of it in the middle. I want to aspire and have the ambition for the moon but also be a practitioner and put in the work. I don’t think I can coast on my reputation, personality or success and riches that I have gained. The most tangible way to be successful is to aim high and be willing to put in the work. I take a lot of pride that I am a better practitioner at social media than most people. I am not a headline reader. I don’t get my ideas from AdAge—I do it. I also do think I am philosophically in-tuned to human behavior; I see around corners. I can pontificate and be in the clouds and have intellectual conversations, but I don’t try to get caught in the middle of the mundane. I try to go tactical and philosophical and be as extreme in both ends as can be.

Let’s say you could have a quick conversation with your younger self, the one that is about to launch his first video on YouTube back in 2006. You have a chance to give that person advice–but none of the advice can relate to digital media. What would you tell them?

I would tell them: Hey, you’re about to do this video in an hour. You think you’ll create QVC but you’ll realize when the red light comes on that you need to be the Food Network because you’ll never be able to hide from this video. This is one of the best things that can happen to you and never let go of it. And that’s what happened and no question my ambition the second before that video was to sell stuff. I was a retailer! And I don’t know what the fuck happened but the second that red light went on, something in my mind said, this video will live forever. And if you have the wrong ambition and the wrong intent you will make some money in the short term but lose in the long term. It was the beginning of the process of me caring about my legacy and understanding that I will be far more successful as a human and as a professional if I worried about my legacy.

The book explores fatherhood and your family. Are there specific ways you are teaching your kids about entrepreneurship and how to think about themselves as entrepreneurs?

I haven’t started talking yet—they’re 6 and 3. Right now, I am listening. Right now, I am watching their behavior. What they are naturally gravitating to. My daughter is older and is further along because she is older and has the showmanship. Sitting in front of the mirror, doing her own YouTube show which has a lot more to do with the YouTube shows she is watching than knowing about what I do. I am good few years away from both her and my little guy from really starting those early conversations whether you are or aren’t an entrepreneur. The conversation will go like, “Look, daddy did what daddy did, you can use that as a North Star and you don’t have to climb that mountain and you’re more than welcome to climb above that mountain.” It’s very important for me to love my children and not to impose my needs and wants on them.

I think that it could be confusing with the way that I roll that people may think I want everybody to be like me. I don’t want anybody to be like me. But I want people to be able to use me as a proxy. They can know who I am and how I roll. Than they can navigate the similarities and the differences. My self-esteem is not going to be wrapped up in my children’s success as entrepreneurs. It will be in their success as human beings.

Can you talk about the lessons your father taught you in business and life?

It’s an interesting question. I am very insular. I like Star Wars, and I always think I am a purebred Jedi. It’s stunning to me how when I think about when my dad taught me—I wasn’t teachable, I was too stubborn, I was too egotistical. I wanted my natural state to be my way. But no question my dad made me a more honorable man. He taught me very early on if you made a commitment, you stick to it. He has zero tolerance for embellishment, let alone lying.

As a storyteller and marketer, you are full of shit at some level. People struggle consuming me at first, whether I am full of shit, as I am being my hyperbolized self. I think that my dad saved me. I do believe naturally I am less noble that I’ve become and I think that comes in the form of my dad giving me very, very, very little room to be full of crap. He had such a zero tolerance, absolute zero, for even exaggeration that it pushed against any capability for me to be full of crap. And I think I went from being full crap at 14 to being a good embellisher but with nobler ends. It’s really stunning.  

There’s a section in the book in which you write about how money and fame doesn’t change people, it just exposes them. A number of people have said some version of that, but can you say a bit more about what it means to you?

In the last year my brand has done really well (strong growth on YouTube, Snapchat, Instagram, etc.) so I am feeling it a lot more. It’s inevitable now that every time I am in New York a few people stop me on the streets and say hi and want to take a selfie, etc. I am flabbergasted how much credit they give me for being nice when they do that. I saw Ice Cube at a Knicks game the other day and he shook every hand and took selfies and was pumped. I do not believe fame or money changes somebody. I truly believe this. It just accentuates who they actually were. It’s just what it is. It’s not like you get all this money and you decide to be a bad person. It just that you have options, you become full of yourself, etc. To me, the reason I talk about that a lot because I am surprised by how surprised people are that I am kind and courteous. Just civil, normal human behavior.

What I am trying to do in the book and hope it leads people—and I do not think I have the answer for people how to find it—I want people to grow three things: gratitude, self-awareness, empathy. I want to quietly trick people into becoming more curious about it and which would lead them on a journey to spend more time around the subject matter. It’s surprising how little is talked about self-awareness in our society.

I am using business and entrepreneurship and social media as an acceptable disguise to create practicality around heavy subject matters. And it’s really weird. I completely believe that I am playing one big game of “I got you.” I love the cat and mouse game of my brand. To be very honest with you, I actually use my contradiction and juxtaposition as a way to filter people and opportunities. I know that I can judge people based on how they judge me.

What keeps you up at night?

Honestly, the health and wellbeing of my family. That’s the truth. In business, I am completely confident because I am in control. In health, I am scared shitless since I am completely out of control. I also I don’t have the audacity of a lot of my contemporaries and friends who think they can mold the world as much as they think they can. There’s a level of humility that I roll with which is very hidden; I am aware, that allows me to not be that scared. People lack practicality, kind of the dirt part of all this,  that I think I am very grounded at.

You are at an interesting inflection point, especially with this book. What do you think comes next for you?

I want to show people that you can build a massively successful empire, a billion dollar infrastructure, on good. On really fun lightweight EQ things like self-awareness, honey over vinegar, patience, humility, being the bigger man. I want to build a human empire.

Jimmy Soni is the co-author of Rome’s Last Citizen: The Life and Legacy of Cato and the author of forthcoming biography of Claude Shannon. He is an editor at the Observer and lives in Los Angeles.