gary vaynerchuk

Gary Vaynerchuk is a best-selling author, entrepreneur, startup investor, and media personality. The New Jersey-born, diehard Jets fan has been hustling since he was 14.

His hustle mentality helped his family’s wine business grow from a few million dollars in annual revenue to upwards of $60 million. It also landed him a dinner with Facebook founder Mark Zuckerberg, who invited him to invest before its 2008 IPO.

Vaynerchuk has amassed a huge following on social media, with more than 1.4 million Twitter followers, 1.7 million Instagram followers, and 2 million Facebook fans. He’s turning his knack for marketing into a media empire, VaynerMedia, which he says will generate more than $125 million in revenue this year.

We spoke with Vaynerchuk about how he got started and how he’s building his Vayner empire, in an episode of “Success! How I Did It,” a Business Insider podcast that explores the career paths of today’s most accomplished people.

In the podcast, we cover:

  • How Gary grew his family’s wine business from $3 million to $60 million in annual revenue
  • What he did in his 20s to set himself up for success in his 30s
  • Why Zuckerberg invited him to dinner, and what it’s like to eat with the Facebook CEO
  • How he found and invested early in Facebook, Snapchat, Tumblr, and Twitter
  • What you need to know to build a big brand and a social-media following
  • How to know if you’re a “fake” entrepreneur
  • Why you should dump your “loser” friends (and maybe even your parents?!)
  • Why he doesn’t eat breakfast or lunch
  • When he will buy the New York Jets — his ultimate goal — and who will be his future GM

Listen to the podcast or read the transcript below:

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The following transcript has been edited for clarity and length.

Alyson Shontell: Gary Vaynerchuk is with us today. He’s a social-media guru and a marketing master. He’s actually one of the first-ever YouTube stars. He turned a wine company that his family started into a business that was making tens of millions of dollars a year. He’s a best-selling author who runs VaynerMedia, which reportedly does more than $100 million in annual revenue.

I want to go back to your childhood. A lot of people might think you were born into success, but your beginnings were pretty humble.

Gary Vaynerchuk: You know, it’s funny, I actually think my kids are going to have a harder time being successful than I was. I think being born in Belarus, coming here with nothing, my parents working every minute — that instilled a huge competitive advantage, a chip on my shoulder, a work ethic. Immigrants win a lot and they win a lot because of a couple core things.

I didn’t start with a lot. I have friends who started with a lot who have now built on top of it, and I’m impressed because I used to think that was a disadvantage. I think there are a million ways to do it.

I like my dad’s narrative the best. He was 22 when he came to America, had nothing, so that’s a really amazing story. I’ll take mine. Baseball cards, lemonade.

Shontell: You were doing all those things that kids try to do when they’re entrepreneurial-minded. You had a series of lemonade stands, right? A franchise almost.

Vaynerchuk: I didn’t know it was a franchise when I was 6. I’ve always had a knack for branding, so even with the lemonade stands, it was “Gary’s Lemonade Stand.” I worked on the signs all day, more so than on the lemonade itself.

Then I learned you had to make good lemonade to build an actual business, so that taught me about lifetime value and quality. I learned a lot as a kid. I was a very poor student, which was really unusual for immigrants, but I didn’t see education as my way out. It originally started as, I’m a good salesman, and then it was, I’m a good businessman, and then it was, I’m a good operator. Now the current term is I’m a good entrepreneur. It’s a DNA thing with me.

Shontell: Like you said, your dad came here when he was 22 and he built up a wine-and-liquor shop. From what I read, you all shared a studio in Queens. There were eight of you in a studio. Packed house.

Growing a family wine business to tens of millions in revenue

gary vaynerchuk

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 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

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

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

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.

We’re a funny match in the 10 or 15 times we’ve interacted because I only want to talk and he only wants to listen. That’s why he’ll probably end up with a hell of a lot more money and be successful, but he’s extremely bright. I like him a lot. I think he’s kind, but most of all he just understands people. That’s weird because people look at him as introverted and quirky and all that but I don’t see it and I never saw it. Obviously, he’s more media trained and grown into himself. I can’t speak to how he rolls now because I haven’t spent time with him but I can definitely tell you there was no confusion from those initial meetings for me, an