How a 'brash Jersey boy' grew 2 businesses to tens of millions in revenue and became a social media super star

gary vaynerchuk Vaynerchuk at the Big Omaha 2010 conference. Silicon Prairie Nes/bit.ly

Growing a family wine business to tens of millions in revenue

gary vaynerchuk Silicon Prairie News/Flickr

Vaynerchuk: Packed house. My dad first was a stock boy and then was a manager. An amazing piece of advice for a lot of kids, 50-year-olds, whoever is listening right now: Saving money is a good strategy. I didn't have stuff, but it was because my parents were saving. They were saving. We didn't get toys. They told us to go outside and paint a rock.

It was very, very smart because after seven or eight years, he was able to buy a liquor store of his own in Springfield, New Jersey — Shoppers Discount Liquors. He built up a great business. A $3 million- to $4 million-a-year business. He made it, right? Literally made it. Middle class, upper-middle class, and made it. We didn't ever need anything. They didn't spend a lot. They're big savers but we made it and then I got dragged into it at 14. I’m the oldest son; I'm one of three.

Shontell: At 14 can you even be in a liquor store?

Vaynerchuk: Yeah, because nobody was really checking. At 16 you can get a permit but I was in there at 14. That's probably why they put me in the basement bagging ice and stocking shelves. Somewhere around 16 or 17, I realized people collected wine, and that caught my attention because I was deep into baseball cards and comic books.

I really enjoyed learning the wine world and really became fascinated by it. That all manifested a couple years later to me launching, in 1996, a site called WineLibrary.com. We rebranded the store to Wine Library and that started my first chapter. We grew the business from $3 million to $4 million a year initially, to $45 million then $60 million a year in a very short period of time.

Having a website 21 years ago for a single-store wine shop, liquor shop, in New Jersey was like having a VR studio in a flower shop right now Iowa.

Shontell: How did you know to do that?

Vaynerchuk: I went on the internet in '94 and in four seconds landed on a AOL bulletin board where people sold baseball cards, and I just knew. The same way that I knew that Twitter would be big and that's why I invested. Or Tumblr or Facebook or Uber. I've done Snapchat. I've done really well on one core principle which is, I think I have an intuitive ability to understand consumer behavior more than the average bear, and I'm not scared to bet the farm on that gut feeling. Even online dating. I met my wife on JDate in 2003.

I just remember thinking in 10 years, every single person — I didn't think they'd be swiping to the right — but I'm like every person's going to do this because this is practical. People are romantic. People are like, “I'll never buy a tomato on the internet.” This is what I heard in 1996.

I'm like, "Yeah you will. Because time is valuable, because other things matter more." I knew because I thought people would buy stuff on the internet long before a lot of people thought that.

Shontell: That's still 10 years before you really became known for your YouTube videos.

Vaynerchuk: Yes, that's right.

young Gary Sasha Vaynerchuk dad son Wine Library liquor store Gary Vaynerchuk's father, Sasha, with Gary in a storage room for rare wines at their liquor store, Wine Library, in Springfield, New Jersey, 2003. AP Photo/Mike Derer

Shontell: That's where I think a lot people assume that your career started but you were working behind the scenes for 10 years building up this internet business.

Vaynerchuk: The thing I'm most proud of is that when people try to take a razz at me as a self-promoter — and I'm very empathetic to that, because I do so much around my personal brand — but if they even spend four seconds digging, they’ll realize I didn't say a word until I was in my mid-30s and had already built an enormously large business. Not by tech standards, but I had no cash infusion. A 10% gross-profit liquor store in the mid-90s — to grow to that scale was very hard.

VaynerMedia's been fun for me. I would tell you secretly, and I haven't said this a lot — I'm trying to give you a nugget for your podcast. I needed to build VaynerMedia up for myself because I was starting to become Gary V, to your point. The wine videos put me on the map. I wrote a book in 2009 called "Crush It," which gets me into the "You're a motivational speaker" or "You're a pundit." It started becoming about my personality and me on Twitter, more than my business accomplishments, so I needed Vayner.

I need to build an agency against the biggest firms on Madison Avenue, and I needed this big success even to just remind myself that I'm an entrepreneur, an operator, an actual businessman first. I'm not what I think there's a lot of right now, which is a lot of people running around and saying they're an entrepreneur on Instagram.

I'm proud of that. I look at something that is upsetting to me. When I see Yik Yak sell for $4 million, I feel bad for the guys.

Shontell: It used to be worth $400 million.

Vaynerchuk: Correct. But I don't feel bad, because that's entrepreneurship. That's business. I think a lot of people are getting confused right now about what success actually looks like. Only a very few will break through and actually sell their business, actually go public, actually make it.

What to do in your 20s to set yourself up for success in your 30s

Gary Vaynerchuk Amy Harris/Invision/AP

Shontell: What did you do in your 20s to set you up for success to really strike in your 30s?

Vaynerchuk: I worked my face off and I learned my craft.

Shontell: How many hours?

Vaynerchuk: All of them.

Shontell: 24? No sleep?

Vaynerchuk: I slept. I'll give you a good example. There are not a lot of 20-year-olds who can say they worked every single Saturday of their entire 20s. Period. I did.

I worked 50 to 52 Saturdays a year, from 22 to 29, until I met my wife and started having to build some level of work-life balance. That's hard work.

Shontell: What did you do on those Saturdays?

Vaynerchuk: I got to Wine Library at 7:30 in the morning and I left at 7, 8, or 9. I just worked. I just built a management staff, I tasted wine, I built up the website. Learned how to do Google AdWords. I just worked. When I tell you worked, I am and was a workaholic and I didn't say a word. I didn't do podcasts. There wasn't social media, but there was. I didn't start a MySpace page to say look at me, look what I'm doing. I had the outlets. I built my craft.

I ran a business. I was a merchant and I was training up my people and training someone to be able to replace me if I got hit by a bus. I was watching trends and that's what led me to YouTube.

I was like this is going to be big, but wait a minute. I can't buy ads on this like I can on AdRoll or on Google. What do I do with this? Should I get a camera and just talk about wine? That sounds like not a bad idea. Content's important. I didn't even call it content, right? This world didn't exist that we all live in now. I thought about Emeril Lagasse when I did it. I thought about that.

I started reviewing wine. That did take off, as you mentioned.

Getting a big break from Conan O'Brien

Shontell: Was it quickly that you got a following?

Vaynerchuk: No. I started on February 20, 2006. In July of 2007, a year and a half later, the break happened. It was still quite small, but I got invited to be on the Conan O'Brien show.

Everybody, and I mean everybody, wrote about me being on Conan because it was like, “A YouTube person on Conan?” Then the clip was awesome. I got him to eat dirt and grass. It went viral on YouTube and that took me from being a top 500 followed person on Twitter to a top 50 person followed on Twitter. Then, Kevin Rose asked me to be on Digg Nation. I was on the "Today" show and Ellen and then it started rolling.

Shontell: Wow. What was it that Conan saw in you that made him invite you on his show? A wine guy, a YouTuber.

Vaynerchuk: He had no idea who I was. A producer of that show's cousin was watching me, thought I was funny. They have these pitch meetings where they're like, “What should we do? Well, there's this weird guy on the internet who's like talking about wine in a very different way.” They called me. I had always thought what would happen if that happened so I had the idea of —

Shontell: You thought about what would happen if Conan called you?

Vaynerchuk: Yeah, of course. I already think about what I'm going to be doing on Alexa voice and what am I going to be doing on VR and how am I going to use message bots and what's going to happen when my kids are 18 and when I buy the Jets — who's going to be my GM?

Shontell: Is it going to be [Group Nine CEO] Ben Lerer?

Vaynerchuk: It's definitely not going to be Ben Lerer. I'm not even going to let him in the stadium. By the way, I referenced Ben earlier. Ben's dad was very successful, and to watch how hard Ben has built Thrillist and the Group Nine Network. It's just very inspiring and makes me hope that my children will have that fire. It's not like he's a trillionaire but he had stuff. Way more than I did.

Shontell: Kenny Lerer, his dad, was the cofounder of The Huffington Post. [Lerer also sat on Business Insider's board.]

Vaynerchuk: Right. Ben matters to me a lot. Ironic that you brought him up because he shows me very closely, because he's a friend of mine — hey, you can have stuff but still be on fire and do it. That's been fun for me.

Anyway. Then YouTube sells.

Shontell: To Google for about $1 billion, and it was a massive deal at the time.

Vaynerchuk: Oh my God. It was $1.7 billion and, just for everybody at home, if Musically sells tomorrow to Viacom for $250 billion, that's what it felt like ... I said, Holy crap. I was right about e-commerce, I was right about Google AdWords, I was right about email, I was right about retargeting banner ads. I'm right about blogging. Now, I'm right about YouTube. I've got something better than, “I can sell wine.” The next time I feel it, I'm going to invest. And that happened a couple of months later, at South by Southwest.

What it's like to grab dinner with Mark Zuckerberg

mark zuckerberg phone Mark Zuckerberg. Getty/Justin Sullivan

Shontell: That's when you became a startup investor? What was your first investment?

Vaynerchuk: Twitter.

Shontell: You go from investing in nothing to Twitter. That's a pretty good track record.

Vaynerchuk: It gets better. The next thing I invested in was Tumblr and Facebook.

Shontell: How did you find Facebook early? In what year?

Vaynerchuk: It was 2008. I had made a video, one of my first business videos that was titled "Facebook should be worried about Twitter." It was like, "Why am I starting to use Twitter more?" It wasn't this big grand statement. It was one person's point of view.

That goes viral inside of Facebook. [Startup investor and founder] Dave Morin sends me an email — he was the head of platform at the time. He goes, "Hey, a lot of people are debating this video. Would you ever come out to Palo Alto and give a talk about it?"

I'm like, "I'm going to Palo Alto next week" — which I wasn't.

I gave a talk about consumer behavior. I didn't even know but Mark was in the audience. He came down. He was like, "You want to have dinner tonight?"

I'm like, "Yep." I had a flight that night. I clearly canceled that.

We hit it off and in 2008, a lot of times when he came into New York, he would hit me up and we got to know each other. Somewhere in that year, Mark and [his sister] Randi emailed me and they're like, "Our parents are selling a bunch of Facebook stock. Do you want to buy in?"

I said "Yep." That was life-changing.

Shontell: What is dinner like with Zuckerberg?

Vaynerchuk: This was 2008, 2009. I'm built on emotional intelligence. I'm not the smartest. I just know what people are going to do. He's a tech kid and an engineer and a Harvard kid. I go in thinking he's that. I leave that dinner and I'm like, "F---, this kid absolutely gets human behaviors." That's when I knew that he was going to win, because I'm like, "Wow, he's got both." He knows how to build it. I can't build stuff. I'm not an engineer. That's not what I'm in to, but I'm like, "He understands what I understand." That was it. I was just bought into him from day one. He's super smart.

Building a new-age ad agency that generates $125 million in revenue

ryan harwood and gary vanyerchuk Gary Vaynerchuk

Shontell: Let's talk about creating VaynerMedia. It’s a huge thing that you're in now, and you and your brother did this in 2009. Does it really generate over $100 million in annual revenue?

Vaynerchuk: We'll do over $125 million this year.

Shontell: Where does that all come from?

Vaynerchuk: That comes from clients like Chase and Budweiser and GE and Toyota and Quaker Oats and Amazon Prime in the UK paying us for either spending their media and given us a commission, making video productions to distribute on the social and digital web or managing their social and digital properties and producing non-video content or consulting for them on their strategies.

Shontell: You're a social-media agency of sorts?

Vaynerchuk: We're a modern-day ad agency. The only difference is we do everything and most don't because I'm building it for myself. I don't want to sell it to a holding company. We've started working with small businesses. I come from that world. Small business, it costs $25,000 a month, so you have to be doing millions in revenue, but we're just building a client service business. It's nothing sexy. It's not like I invented anything. The only difference is I'm really good at marketing.

Shontell: Sum up what VaynerMedia is because there are a ton of moving parts. And then how did you start it?

Vaynerchuk: In 2009, ESPN sent me an email and said, "Can you come to our office and talk to us about Twitter? Why do you, Gary V, have more followers than all of the Disney properties combined?"

Shontell: How many followers do you have these days?

Vaynerchuk: These days I have 1.4 million on Twitter, 1.7 million on Instagram, 2 million on Facebook. At the time I had about 700,000.

The email was sitting in my inbox because I was busy. By the time I came back to it that night, they had already emailed a second time. They're like we'll pay you $5,000.

It was really cool and I was really excited. We had this conversation and I get out of the office and my brother calls me. My brother is now a senior at Boston University. It's February and he's graduating in May. We're under the gun because we've promised ourselves we're going to start a business together. We're thinking fantasy sports, because we think it's going to be big. We're trying to figure it out and I call him and I go, "You know how I talk about maybe one day buying businesses? Instead of doing that cold, maybe we should start a consulting firm," is what I said. Learn about corporate America, make some money, and then decide what to do. That's what we decided to do.

I got another email from Gillette, the razor company, to do some sort of idea session. We just started. We didn't know what we were doing. We hired four or five of AJ's friends from college and high school and we literally started reaching out to people. I started using my network.

The first two years, what happened, a couple months later, “Crush It,” came out and that's when Gary V. was born.

Shontell: That's your first book?

Vaynerchuk: That's my first book. It went really viral.

Shontell: You did a 10-book deal, right?

Vaynerchuk: I did. What was not reported in there was if my first book sold enough copies to pay for the entire 10-book advance, I would become a free agent, which is what happened.

I wrote that book. It went very viral and then I started getting offered $25,000 to give a speech and that was so hard to say no to at the time in my life.

Shontell: Why did you say no?

Vaynerchuk: I didn't, which means I wasn't involved in Vayner that much the first two years. I got us the clients, I would check in, but it was really AJ and our band of 20 young characters in the beginning and the first two years show that. I think we were doing $2 million in revenue.

In August 2011, I decided to take over full time because I was stunned that two years later, nobody was doing what I wanted to do two years earlier and I realized that corporate America's slow. I attacked. I saw and opening and I attacked. I got serious. From August 2011, which really means 2012 because I was cleaning up and hiring ... In the last five years, we've gone from 25 to 750 employees. From $3 million to $125 million in revenue, and now we're a real player as an agency.

What you need to know to build a great brand

Gary Vaynerchuk happy Jets fan celebrate A.J. and Gary Vaynerchuk. Jeff Haynes/AP Images for Panini

Shontell: When you're building a brand, what are the most important things that you need to know?

Vaynerchuk: First of all, you have to know who you are, what you are, and what you stand for. That's clichéd marketing-bullshit jargon, but it does matter. It helps. You have to know who you're targeting. I think too many people fight the market. There are certain people who are never going to want your stuff no matter what you do. There are certain people are never going to love me because I curse and I have bravado and I'm a Jersey boy and I'm brash and they won't take the time to see the humility and the patience and the truth. They shouldn't.

Who am I to actually make them have to take that time?

Brands have to be honest with themselves and know who's going to buy their stuff and who's not. Most importantly, they need to market in the year they actually live in. We have brands spending ungodly amounts of money on print, television, outdoor radio, programmatic banner ads, website takeovers. Garbage.

When I say garbage, they work-ish. They're just so overpriced. I don't know what else to say. I do not believe that it is worth the hundreds of thousands of dollars in distribution and hundreds of thousands of dollars in cost to make one 30-second video to tell a 29-year-old woman that your soap is great, in a world where she is not going to consume that commercial.

I do not think it's great to spend millions of dollars on banner ads across the desktop internet on the right side below the fold of tons of websites. Nobody's ever going to pay attention to that banner ad because the CPM cost is low.

Shontell: One thing that you’re doing at Vayner that's interesting is your merging content and brands. In the journalism world, people start screaming. There was news that BuzzFeed is launching a team of people who are going to start sending you things that you should want to buy. There were people in the journalism who were like, "Oh my God, good thing they work for a forward-thinking publisher, because The New York Times would never do something like that."

Vaynerchuk: New York Times does it. New York Times has a wine club in their newspaper in the “Dining In” section. All that is is romance and highbrow snobbery … The New York Times sells wine. The New York Times is a competitor of my family's wine business. I don't know what else to say. I have a lot of friends who work at The Times because I'm a fan. It was so fun to make fun of them.

I was like, “You've been doing it.”

They're like "Oh."

I'm like, “Where are you?!”

But yes, I have. I've started something called the Gallery. VaynerMedia is what I've been running. I've created a holding company called Vayner X. VaynerMedia sits on the left. On the right side is something called the Gallery. Our first purchase was a company called Pure Wow. It's in that Pop Sugar, Refinery29, female space.

I had become increasingly aware that Vice and BuzzFeed and Vox were building creative shops and felt like they were true competitors because they had better digital DNA than, let's say, the agencies on Madison Avenue. I thought, "Look, I can sit here and watch that happen or I can do the reverse." In my great dream of building the greatest communications and marketing machine, publishing will be part of it. I never worried about the conflicts and things of that nature because everybody's doing it. New York Times is doing it. It’s just that an agency hadn't bought a publisher, because most of them couldn’t afford it and most of them don't have the — to be very frank — the ambition I have.

When you want to buy the New York Jets, you have to do big things.

The goal is to buy the New York Jets

Shontell: How close are you to buying the Jets?

Vaynerchuk: Far. The Jets are probably $2.7 or $2.8 billion. I'm nowhere close to that. The good news is I don't want to buy the Jets tomorrow. I love the journey of being an entrepreneur more than I like of the idea of buying the Jets.

The good news is, Woody Johnson's healthy and young and not looking to sell. We'll see how it plays out and if the booby prize is the Dallas Mavericks ... Well, no, actually Cuban's too young ... If the booby prize is the Milwaukee Brewers, we'll see and maybe it'll be something altogether different. All I can focus on is trying to build the business around giving me those kinds of opportunities in the future.

Why you should dump your 'loser' friends and family members

Shontell: I have a couple of wrap-up questions because you produce these advice videos on big topics that everybody thinks about when they run a business. First one: dropping a "loser" friend. You've done a video on this.

Vaynerchuk: Wow, I can't believe you went there. This is a tough one.

Shontell: How do you get rid of friends who are useless to you?

Vaynerchuk: This has been the one that I've been very hot on talking about in the world but I've been scared of because even when you just said that, I'm like, “Ugh. This guy's terrible.”

Shontell: It's a good, provocative headline.

Vaynerchuk: It is. I think that people are keeping very negative people around them and if they aspire to change their situation, it's imperative to audit the seven to 10 people who are around you.

That’s the reason I go after a friend, or a parent. In the details of that headline, I said "Hey, you may have to audit your mom. Not that I want you to never talk to your mom again, but you may want to take a step back." I've done this for friends and acquaintances. It's a very painful, eye-opening experience to realize, “Wait a minute, my dad actually doesn't want me to be successful because he's not happy.” Whether you call it misery loves company, it's not like parents are bad people. It's a human trait. It's just a thing.

Maybe if you got rid of one friend or spent a lot less time with one friend who's a real drag and a negative force and added a positive person in your office ... If you switched it from 80 days hanging out with your negative friend and one day with your office acquaintance who's super positive, to four days with your negative friend and 12 with this new person. I've physically watched I mentor in my organizations have a totally different life on that thesis.

It's lonely at the top — if you don't like that, then you don't start a company

GettyImages 457687288 Stephen Lovekin/Getty Images for Pencils Of Promise

Shontell: All right. That makes sense. It's basically the company you keep and if it's positive company, you think you'll be more successful. Another topic you talk about is, “It’s lonely at the top.” How do you solve for that?

Vaynerchuk: You don't solve for it because it's the truth. When you're the CEO, it's on you. It's Sally's fault. It's Rick's fault. Everything that's wrong at Vayner is my fault.

Here's what I would say. 80% of you who are listening are actually not entrepreneurs. You think you are. You're doing it because it's hot and what you really are is a great number three [third employee at a startup], or a great number seven. You're not actually built for eating shit and being in fire all day long. You're going to be more depressed. It's even harder and I think it's time we talk about entrepreneurship in a real way, because there's a lot more underlying suicide and depression in our tech startup entrepreneurial world …

I think we're in a vortex of fake entrepreneurship that's going to lead to a lot of pain so I want to talk about the loneliness because it is hard. I've had a shit week, Alyson. Honestly. There's been a lot going on. Clients, internal stuff. It's not fun but it's my calling. I don't even know anything else.

Shontell: How do you deal with it? Do you meditate?

Vaynerchuk: I put in perspective and honestly. I love it but I love shit. I love the pain. I love the process. I'm just watching kids I invested in, and really struggle and go to Coachella and skiing every weekend to deal with it. Which then means they're not putting in real work to the business.

They would have killed it as number nine at Instagram. They would have made a fortune. They would have crushed it as number 11 at Purple Mattress or Casper. They would have dominated as number 29 at Business Insider. But everybody thinks they're a goddamn founder now.

Shontell: The last one that I would ask you is you're clearly a confident person, you don't mind speaking your mind, you're assertive. How much of success, do you think, requires that?

Vaynerchuk: I think it's the one we see. I think the opposite version of me is the one we don't see, which is there are tens of thousands of outrageously successful businesses of very quiet, very calculated, calm executors who are confident.

You can't be successful without being confident. They believe in themselves. They have their own version of assertiveness … I think confidence matters and I think other things matter, like I would tell you empathy is probably why I'm more successful than confidence. I'm empathic to the customer, to my business partners, to my employees.

Vaynerchuk: You've got me in a very thoughtful zone. This is a very weird version of me.

How to focus when you're doing a million things at once

Gary Vaynerchuk Roy Rochlin/Getty Images for 2016 Advertising Week New York

Why eating is a waste of time

Shontell: You don't eat?

Vaynerchuk: Nope. I eat at night.

Shontell: Don't you get hungry? I could never do that.

Vaynerchuk: Nope. This is the part where AJ jumps in and says, “Gary's actually a robot. That's why this is all happening.”

Shontell: Do you sleep? Are you one of those four-hour sleepers?

Vaynerchuk: Nope. I'm all in on Arianna Huffington’s [you-need-sleep theory]. Give me six or seven hours. Give me 12:00 a.m. to 6:00 a.m. every day, then I work out and then I work. I also take seven weeks of vacation with my family. It’s extremism on my work-life balance. But I'm getting a lot done.

Shontell: Well, that's something to aspire to.

Vaynerchuk: It's something to aspire to if it makes you happy. It's not to aspire to to make money. I can tell you that right now. You can make ungodly amounts of money working 9 to 5, or 8 to 2 on Wall Street. It's not about the money. The thing to aspire to that I think I'm a blueprint of is, forget about people knowing who I am or how much or little I make in my life. I'm happy every day.