Serial Entrepreneur: Gary Vaynerchuk

Growing up in New Jersey in the 1980's and 90's, Gary Vaynerchuk honed his business skills trading baseball cards and selling wine at his dad's liquor store. He discovered the potential of Youtube early on and launched Wine Library TV, an unfiltered, in-your-face wine review series that boosted the family business and branded Gary as an early social-media guru. From there, his marketing career exploded, and suddenly Gary Vee seemed to be everywhere: consulting, speaking, vlogging, tweeting, and publishing best-selling books, all while growing what is now a sprawling media company, VaynerX. His energy can be exhausting and his critics think he's full of it, but Gary shrugs them off; he credits much of his success to his immigrant upbringing and his parents' strong work ethic. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Guy Raz?

  Our presenting sponsor today is Anthropic, the team behind Claude. Every founder on this show started with a hard question. Not the marketing plan, the 2 a.m. kind. Is this idea any good? Am I the one to build it? Should I quit my job? Anthropic got built the same way. A public benefit corporation founded on one hard question. How do we make sure AI goes well for people? So they asked over 100,000 people their hopes and their fears and are publishing what they find, even the uncomfortable parts. Me? I've got my own hard question about AI. Here it is. If everyone has access to something that can help them write the business plan,

• 0:46Guy Raz?

  build the prototype, analyze the market, maybe even come up with the idea, what separates the people who actually build something from everyone else? I don't have a clean answer yet, so I've been sitting with it with Claude. There's hope in hard questions. Ask yours at claude.ai/hibt. We get support from U.S. Bank. A question I love asking founders. What's the one decision you almost didn't make? The one that changed everything? Because it's never the obvious stuff. It's never, I decided to start a company. It's the small, boring, Tuesday afternoon decision you barely remember making until you realize it's the reason everything after it either worked or didn't.

• 1:32Guy Raz?

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• 2:14Guy Raz?

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• 2:58Guy Raz?

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• 3:40Guy Raz?

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• 4:23Guy Raz?

  And it reminds me a little bit of the founders I talk to on this show, because the best ones obsess over things their customers will never see. Tiny details, invisible improvements, relentless iteration. And not because anyone's watching, but because it makes the product better. That's what the mobile brand does. It engineers fuel the same way great founders engineer their products. Mobile Supreme Plus Premium Gas helps keep engines three times cleaner, which can mean better performance and improved gas mileage. It's for people who care about what's under the hood, even if they never see it. Three times cleaner compared to mobile regular gas in port fuel-injected engines. Actual results may vary.

• 5:07Guy Raz?

  Visit mobili fuels.com for details.

• 5:13Speaker 01

  You know, I have this wine store. I have this wine show. I'm a wine guy. When I started putting out a little business content in 2009, and every comment said, "Stay in your lane, wine guy. What do you know about business?" That's when I was like, wait a minute. These people don't realize you can be a wine guy and a businessman. I couldn't wrap my head around it. I was like, why are they telling me to stay in my lane? I was a business guy before I was this wine guy they know. Of course, I can talk about business. I'm a businessman.

• 5:51Guy Raz?

  From NPR, it's How I Built This, a show about innovators, entrepreneurs, idealists, and the stories behind the movements they built.

• 6:02Guy Raz?

  I'm Guy Raz. And on the show today, how Gary Vaynerchuk started as a wine salesman, grew into a master marketer, and built a massive one-man brand that's inspired tons of people to start their own companies.

• 6:20Guy Raz?

  There are lots of people who don't take Gary Vaynerchuk seriously, who think he personifies the worst elements of hustle culture, who write snarky things about him because he violates their sense of what it means to be cool, because he's earnest, exuberant, and sometimes so over the top that it can be a little hard to take. But Gary Vaynerchuk doesn't much care about what his critics think, and he doesn't pay all that much attention to the praise he receives either. Gary is about as pure an entrepreneur as anyone who's been on this show. It's in his blood and soul in a visceral way that is almost incomparable. You can hear it,

• 7:05Guy Raz?

  you will hear it, in his voice, in his expressions, in the frenetic speed and cadence of his sentences. At age 45, he's already started more than a dozen businesses and sold a few as well. Gary is one of the pioneers of social media marketing and one of its most influential practitioners. He produces a seemingly endless amount of daily content: videos, tweets, blogs, Instagram posts, Facebook chats, a podcast. And yet, for the most part, he's not trying to sell you anything. On his website, there's no shop, no pitch to

• 7:45Guy Raz?

  take a course or sign up for a seminar, no products for sale at all, partly because Gary has already made a lot of money, from the two businesses he sold, from his bestselling books, but also from his branding and marketing studio and other ventures that fall under his company, VaynerX. What he offers is advice on marketing, on working, on branding, on entrepreneurship, even on how to deal with critics and skeptics and haters. And I should mention, he does all of this with a lot of F-bombs, which, fair warning, you will hear in this interview. Gary has had a remarkable ability to see around corners.

• 8:30Guy Raz?

  Back in the late 1990s, he convinced his dad to let him set up an e-commerce website for the family's liquor store, which Gary turned into a powerhouse, direct-to-consumer wine business. He was one of the earliest YouTube vloggers and amassed an enormous audience talking about wine. He saw the early promise of Twitter and figured out how to use it to help massive brands reach younger consumers. He co-founded one of the early online reservation sites, called Resi, that he would go on to sell to American Express. But his biggest secret? It's not a secret at all. Gary Vaynerchuk works really, really hard. Work is the fuel that allows Gary V to be Gary V.

• 9:15Guy Raz?

  And he explains the source of that work ethic in his status as an immigrant. Gary was born in the Soviet Union and was now a part of Belarus. His parents were Soviet Jews in a society that often discriminated against Jews. So in 1978, when Gary was around three years old, his parents managed to immigrate to the United States. They settled in a tiny apartment in Queens, New York. They had no money, no language skills, and no professional qualifications that were recognized in the US. But they did have a few relatives in the area.

• 9:49Speaker 01

  I remember random things like my great-grandfather. I actually remember him quite a bit. I remember a lot of one-on-one time with him. He would walk me to the park. I remember riding beat-up big wheels that we found in the trash. I remember that he occasionally would buy me vanilla ice cream, and that blew my mind because even at that young of an age, I kind of knew that we didn't spend money on most things besides food and clothes. So we were a poor-ass family.

• 10:17Guy Raz?

  Yeah. What did your dad, what did your parents do for a living in those early years? Do you remember?

• 10:24Speaker 01

  Of course. Yeah, I mean, this is the beauty of being only 20 years younger than your parents. You remember a lot of stuff.

• 10:30Guy Raz?

  Yeah.

• 10:31Speaker 01

  First, the family was very big on picking garbage. And selling it at flea markets and things of that nature, real rugged stuff. It was really hard. The US was not flourishing. We were, it was,

• 10:43Guy Raz?

  The seventies in New York.

• 10:44Speaker 01

  Yeah, it was nineteen seventy eight, New York. My parents were like, wait a minute. We heard propaganda of streets of gold. Grandma just got mugged. Like, you know, like, it was like, it was hard. And so my dad was fortunate. He had a great uncle, who was extremely well off. And so he was gonna kind of take care of us. But when we were in Italy, waiting for our visas, he died. And so we came to the US thinking we had a little bit of this kind of like, you know, genie, gonna take care of us. Now he's passed the credit of, of his children, Bob Segalman and Arlie Newman. They did do a nice job by my dad. And one of the nice things they did was they gave him a job as a stock boy in a liquor store in Clark, New Jersey.

• 11:24Guy Raz?

  And they were, they, just to be clear, they were like your sponsors?

• 11:27Speaker 01

  They were like our sponsors. That's exactly right.

• 11:28Guy Raz?

  This was a liquor store they owned?

• 11:30Speaker 01

  This was a liquor store they owned. And my dad gets a job there, which was very nice. And there was this mass exodus at one point at the liquor store. And my dad had basically got propelled to manager. Literally, my dad's first American words were things like Budweiser and Carlo Rossi and Boone's Farm, like, literally. Later in my career, when I met some of the salesmen that called on my dad when he was just a stock boy, not the owner, they would tell me stories about my dad, like, literally, literally, did not speak English. And so, you know, my dad became the manager, got paid more, and we moved to Edison, New Jersey, where really, this story of my life starts to truly form.

• 12:11Guy Raz?

  All right. So your family moves to Edison, and your dad is managing this liquor store with an eye to eventually opening his own liquor store?

• 12:20Speaker 01

  Yes, because my dad's boss was his great uncle, you know, his second cousin removed him.

• 12:26Guy Raz?

  Yeah.

• 12:27Speaker 01

  So my dad, Obviously, giving me a lot of this DNA was an entrepreneur, was a hard worker. And so this gentleman recognized that. And at some point in the mid eighties, this gentleman allowed my father to buy half the business. You know, going from zero, not having a language to four, five, six, seven years later to own a piece of a business. It's an incredible accomplishment and I admire my father so much for that. And so he became half owner of that store. And then only 10 years after he came to this country, he opened a very small store in Springfield, New Jersey, which

• 13:03Guy Raz?

  This was called Shoppers Discount Liquors?

• 13:05Speaker 01

  Thank you for doing the homework, Shoppers Discount Liquors. I'm sitting in my office in New York right now. His second store was not much bigger than my office. It was literally a tiny home, but it was his and that was huge.

• 13:17Guy Raz?

  And liquor is a pretty good business because it doesn't go bad.

• 13:21Speaker 01

  It's a good business that it doesn't go bad. It's better than food that way. It was a good business that people drink when things are good and when things are bad. It's not a good business in the part that my dad's store was called Shoppers, and let me hit it now.

• 13:33Guy Raz?

  Discount Liquors.

• 13:35Speaker 01

  Yeah. Product, everybody bought for the same price because that's the regulation of the liquor industry. He was selling everything low and running ads. That's how he maintained growth, top line, but it wasn't a lot of profit. And then we kept his expenses low because my dad surely, he didn't love the idea of paying employees too, too much. So he kept his overhead down, very good operator that way, knew how to like not lose money. But it wasn't a profitable business.

• 14:03Guy Raz?

  Gotcha.

• 14:03Speaker 01

  And, and what I realized was right. My dad ran a business where he valued the business more than the money he took out of it. He cared so much about the business. He didn't care that it wasn't profitable. He just wanted to keep being the best store in town and keep his position.

• 14:16Guy Raz?

  Yeah. What kind of kid were you? I mean, were you, first of all, at school, was school? I mean, did it come easy for you or was it harder?

• 14:25Speaker 01

  School was incredibly easy to me until third grade. I got straight A's. And then I don't think I got another A except for gym for the rest of my life. As a matter of fact, my interest level and my capacity to sit and be bored was zero.

• 14:40Guy Raz?

  Yeah, you could not focus on the teacher. You couldn't focus on the lesson plan. Your mind was wandering.

• 14:45Speaker 01

  But you know what's funny? I have incredible focus, guy. Like, I'm outrageously focused. I wasn't willing to compromise my interests to appease what seemed to be required. And that is why I am still to this day. Now, I didn't understand it at the time. I got Fs in science, but I got Bs in history because I was very interested and it was very easy to focus. I think I am a true byproduct of the vulnerability of a rigid system. Because if you would have taught me why New Coke failed in high school, I would have got an A++ because I would have been fascinated.

• 15:22Guy Raz?

  Yeah. And did your parents care that you didn't excel at school?

• 15:26Speaker 01

  My mother, my father had no idea what was going on. He spent 150% of his time on the business. And, you know, I didn't see my dad until I started working in the store at 14. My mother, God, she's so smart. She grounded me every single report card. For two weeks, no TV, no video games, no friends. It was, when I tell you the anxiety I still have to this day.

• 15:50Guy Raz?

  About bringing the report card home?

• 15:52Speaker 01

  Not bringing the report card home. You'll love this. Still to this day, like on a November 6th, the breeze of the fall/winter thing hits me. And I can feel sixth grade me saying, uh-oh, it's time for me to check the mailbox for the report card. Because if I can get it before my mom gets it, I'm gonna flush it down the toilet, which will buy me two weeks before she grounds me. Like, that was my life. It was cat and mouse between me and my report card. But my mom knew who I was. And she saw it.

• 16:20Guy Raz?

  And, I mean, clearly you were focused on... Things outside of school, like, right? Like, I think you started to work at your dad's liquor store pretty much every weekend when you were around 14, right?

• 16:33Speaker 01

  Yes. My dad's store was in Springfield, New Jersey, on the slightly, slightly wrong side of the tracks of a very affluent area, because it literally, my dad's parking lot of his liquor store was in Milburn. And Milburn was attached to Short Hills and Summit and Livingston and Money. And, and by the way, I didn't like my dad's liquor store at first. I was selling baseball cards, making a lot of money as a kid, and now I was in this liquor store making two, three bucks an hour. And I didn't like beer and liquor, but I realized that people collected wine, and that was the trigger.

• 17:07Guy Raz?

  That, that's interesting. I mean, were you, I mean, were you expected to work in a liquor store? Was that, was it an expectation?

• 17:13Speaker 01

  Yes. I remember at 12 or 13, my mom saying to me, "Well, you're not going to Harvard, so you better mentally get prepared, because you're going to be working at the store every day of your life soon." There was no conversation.

• 17:24Guy Raz?

  Yeah.

• 17:25Speaker 01

  I was the son of a merchant of a first-generation family.

• 17:27Guy Raz?

  Yeah.

• 17:28Speaker 01

  I was the only child born in the old country. I was the oldest. This was my destiny. Now, I don't think, I don't think there was, I didn't feel pressure that I had to take it over one day.

• 17:39Guy Raz?

  Yeah. What did you think about the liquor store? Did you think that it was like, I don't know, did you have an impression of what it was? Did you think it was sort of low-class?

• 17:48Speaker 01

  What I thought was, "This stinks." Like, "Why am I here? Like, I could be at the mall, or the JCC, or the fire station right now in Hillsborough, New Jersey, selling my Eric Davis rookie cards that I bought this week in school, and he's hot. He had three home runs last night, and they're up to six bucks a piece right now. I bought them for two, but I can't do anything about it, because my parents are making me be here." And by the way, there was no doubt that I was going to work every weekend and every holiday and every summer vacation in high school, and that was non-doubtable.

• 18:24Guy Raz?

  I, I wonder whether you... How, I mean, you were a baseball card collector and a lot of, I love collecting baseball cards and, you know, selling them now and again. Remember Jose Canseco? How much that rookie card was worth? It's crazy now. But it seems like your interest in baseball cards and the collecting of baseball cards, you started to kind of connect that with wine. I mean, you were working in a liquor store, but it seems to me that the baseball card collecting kind of side of you got you thinking about wine. Do you think that's fair?

• 18:55Speaker 01

  Not only do I think that's fair, that's exactly what happened. I learned a lot from the ages of nine to the ages of 15 in, in doing baseball card shows. I was a child setting up tables with grown men and doing business. And by the time I got to my dad's store, I was a little seasoned for a 15-year-old, 14-year-old. And then I got to listen. I educated myself in class, took advantage of every minute, started to really know wine, understood human behavior, understood collecting, and took everything. That would be the word I would use. Everything. From the, by the way, let me give you one. When you're setting

• 19:39Speaker 01

  up a table at a baseball card show, you start realizing by, if you're talented like I was and you had the gifts that I was given, that the way you set up your table will be a huge variable of how much money you make. Where you put cards, what signage you use, where is your table? And by the time I got to my dad's store, the first thing I did for my dad was merchandise the store. I would make signs. And I would move around cases. I would say, Dad, you want to sell this wine, right? And he was like, yeah. I was like, why is it here? I'm like, look how, and this is a 15-year-old. Dad, look how people walk in the store and they walk that way first because of the way you've set up the store. That's opposite of this thing. You've got the thing we don't want to sell there, but

• 20:23Speaker 01

  this is the profitable. And so I started merchand, I was a merchandiser first.

• 20:26Guy Raz?

  And he was listening to you?

• 20:28Speaker 01

  He was listening to me, which I, you know, this gets me emotional. My dad really gave me a lot of freedom. Now, I know for fact it was earned. I know my pops. He would be quick to shut everything down. He very quickly realized, probably, he tells me and I believe him because he doesn't bullshit. He basically knew right away, first weekend, because I was a 14-year-old supposed to be downstairs finagling myself upstairs trying to sell people stuff. It was just in me, right? And he knew that. He knew what that was.

• 20:58Guy Raz?

  And by the way, were your parents just expecting you to stay on in the business after high school? I mean, did they want you to go to college? Did you want to go to college?

• 21:09Speaker 01

  No. I planned on not going to college. My parents didn't know anything. My mom was very insular. She didn't go to my parent teacher conferences. She had no idea. My mom had no, this is a true story. My mom asks me February of my senior year of high school, "So what are we doing about college?" I laugh. I go, "What do you mean? It's over. I'm gonna go right into the business." She rolls up on me, stares me down and scares the shit out of me, points her finger directly in my face to my, and my mom's an angel, by the way, and goes, "You're going to college? Figure it out?" Turns around, turns back around and says, "And don't make it a community college."

• 21:47Guy Raz?

  Huh. And so you actually wound up going to a four-year college. It's called Mount Ida College, which is a sort of a small school in Massachusetts, right?

• 21:57Speaker 01

  Yes. In Mount Ida College, first semester, I hear the internet for the first time. And I decide, "Oh, my God, I'm not gonna launch 800 Toys R Us of wines," which is what my plan was at that time. "I'm gonna launch a website," even though I did not own a computer, even though I wasn't techie. And a year later, I launched WineLibrary.com, one of the first e-commerce wine businesses.

• 22:19Guy Raz?

  This is like 96, 97. I mean, no one's doing that. I mean, people are going on like Prodigy and AOL and, you know, you've got mail. Like, nobody's, but you're thinking, "This is the way to sell wine?" Or, "This is the way to market wine?" How are you thinking of it? So, okay.

• 22:35Speaker 01

  And I want to say this publicly. The greatest thing that was ever done for me in my life professionally was my father making an enormous bet on spending the $15,000 to build WineLibrary.com, which was like a good trillion dollars.

• 22:51Guy Raz?

  Wait, so, so the idea was to build a website and you wanted to call it WineLibrary.com?

• 22:57Speaker 01

  That's right. My dad went to Napa on a trip because now he was like getting deeper into the wine world.

• 23:02Guy Raz?

  To wine, okay, yep.

• 23:03Speaker 01

  Because the business was turning. Everybody kept calling their wine sellers their wine library. This is our library. And so my dad actually came up with the name Wine Library. I just knew he liked the name. He wanted to use it as a catalog or as like a thing. I was the one who says, this is what we'll call our .com, but that's how the name Wine Library was come up with.

• 23:26Guy Raz?

  Because the business was called Shoppers Discount Liquors.

• 23:28Speaker 01

  Correct.

• 23:29Guy Raz?

  So you, you said, let's not do Shoppers Discount Liquors.com. Let's call it, let's just call the website WineLibrary.com.

• 23:36Speaker 01

  My dad was part of a co-op. So there was 40 stores named Shoppers Discount Liquors in New Jersey.

• 23:42Guy Raz?

  Right.

• 23:42Speaker 01

  They were all independently owned, but they all wanted to run a full-page ad in the Star Ledger.

• 23:46Guy Raz?

  It was like, it was like Ace Hardware.

• 23:48Speaker 01

  Correct. I wanted to not be part of that because I wanted to build the biggest wine company in the world. So I strategically bought WineLibrary.com because I already had bet the farm that the internet was going to be the future and I knew that if I did this, because my dad was not looking to give up the shopper's name, he came up with it.

• 24:08Guy Raz?

  Yeah.

• 24:08Speaker 01

  He was, that was his baby and he was not listening. That was a place he was fighting me on. I wanted to change the store name. He was petrified of that. But I knew that if I changed the .com to that, that eventually it would tip and that's exactly what happened.

• 24:23Guy Raz?

  By the way, how did you learn wine? Okay, so you were just 21, 22 at that time.

• 24:28Speaker 01

  I learned wines through books, through books and really Robert Parker's Wine Spectator. And there was a bulletin board on Prodigy called Mark Squire's Wine Bulletin Board. And so I lived on that community board.

• 24:39Guy Raz?

  And did you have, I mean, some, some people like, like Jancis Robinson are known to have like just superpower palate, right? But did you have, were you one of those people with a natural palate?

• 24:50Speaker 01

  Yes. I knew everything on paper, but the first year of me tasting wine heavily in the store, it all just tasted like wine.

• 24:59Guy Raz?

  Yeah.

• 24:59Speaker 01

  And I was starting to worry about this imposter syndrome of, shoot. What are these people talking about? I don't taste boysenberry. The hell is lychee fruit? Like, like, I would literally after work, after working a 12-hour day, go to the King's supermarket and buy all these weird fruits and vegetables and spices and go home at 11:00 PM. This is, this is how obsessed I was. I'm a 22-year-old boy on a Friday night at 11:00 PM instead of going out, sitting and biting cinnamon sticks so that I could really capture the nuance of cinnamon to see if I would pick that up on Barolo's. Like, I, God, I was obsessed.

• 25:44Guy Raz?

  Hmm. So after you graduate college, you come back to New Jersey and you work in the shop, and you've got the WineLibrary.com site. And how are you getting people to find out about it?

• 25:55Speaker 01

  I work the floor.

• 25:56Guy Raz?

  The floor of the, of the shop?

• 25:58Speaker 01

  That's right. I am in the store 12 hours a day. So you come in the store, I see you.

• 26:02Guy Raz?

  Gotcha. Gary Vaynerchuk comes up to me and he says, "What are you looking for?"

• 26:06Speaker 01

  By the way, even the way, even the way you just said that, you nailed. The Gary Vaynerchuk you see on the internet was that boy.

• 26:13Guy Raz?

  Yeah.

• 26:13Speaker 01

  "How are you? What can I help you?" Like, just pure, pure enthusiasm. "And I will not let you leave my store. I will make you a hostage unless you give me your email address." Now, this is 1996, '07, '08, and it was really '97, right before I graduated, and then '98, full-time. A lot of people didn't even know they had an email, just got it from work. My favorite stories, because I can see them in my brain, are people say things like, "Oh yeah, I got one. It's AOL at Yahoo.com." I'm like, "No, no, no, no, no. You probably have an AOL and a Yahoo." And, and so what I did was, I built a very powerful 10,000, then 20,000, then 30,000.

• 26:54Guy Raz?

  Wait, 10,000 email addresses? No, not from people just coming into the store.

• 26:58Speaker 01

  Over the course of the first year, yeah. I would say the first year, we probably had about 13,000. We did a little direct mail. But I would argue, I mean, you know what's funny? I'm such an extreme character that I think when people hear my stories, they don't believe them. There's the level of embellishment. There he's trying to make a point and I'm like, no, no, no, I'm telling you right now. Every human being that walked into the liquor store for an entire year. I would not let them leave to the best of my ability, which is very high without giving me their email address.

• 27:28Guy Raz?

  I I don't know why somebody wouldn't believe that.

• 27:31Speaker 01

  Well, I think I think I think, you know, the store was a big enough store that we had enough customers to that 10,000. Like it was easy to get to that base. What ended up happening was that worked so well. Driving people to the website and buying on email. That it gave us our first level of profit. You know, the first year I ran the business. We went from a four million to a $10 million business.

• 27:50Guy Raz?

  So this was, I mean, this was an email list that you would send out to people. Uh, with the wine deals and they could directly click on that email and. Order wine because this is still like the late 90s, early 2000s. It was that possible to do?

• 28:04Speaker 01

  It was, but to your point, 90% of the people didn't know what the hell you were saying.

• 28:09Guy Raz?

  Right.

• 28:09Speaker 01

  Nobody trusts putting a credit card in the computer. Nobody really even knows how to buy on a website. Most people don't even know how to look at an email newsletter yet. And look how well my dad's business is going. This is it. Like wait to two, and this is where I was wrong. Wait to the year 2000 when everybody in America buys everything on the internet. In my youth, I did not understand yet because I didn't have the, you know, pattern recognition or experience. To know the things that I saw would take a decade to happen, not a year.

• 28:37Guy Raz?

  This was still before like many states now allow. You know, direct wine sales and but even there's still some challenges with some states, as you know, but at that time. Were you only selling pretty much to people in New Jersey?

• 28:50Speaker 01

  Yes, comma. In 2000, we opened it up a little more as FedEx and UPS became more progressive. So yes. 9899 was very New Jersey and then we built a big reputation. Because Wall Street, a lot of people live in the Jersey suburbs.

• 29:05Guy Raz?

  Right.

• 29:06Speaker 01

  And Wall Street was very, is very viral at that time because people now have email for the first time. So I'm, think about it. This is going to make so much sense to everybody. I'm sending an email. For Opus One at the lowest price in the country.

• 29:18Guy Raz?

  What was the price?

• 29:19Speaker 01

  At the time, Opus One was a $90 wine and I'm selling it for $62.99.

• 29:24Guy Raz?

  And that was the hottest American wine in the city, is the hottest wine.

• 29:28Speaker 01

  Super hottest wine at the time. So I send it to Wall Street. Now, think about the psyche of a Wall Street guy. Let's call it what it is.

• 29:36Guy Raz?

  You send it to who? You send it the email newsletter?

• 29:38Speaker 01

  Rick Thompson comes in from Short Hills, buys six bottles of Duckhorn Sauvignon Blanc for me. I get him on the email newsletter.

• 29:45Guy Raz?

  Yep.

• 29:45Speaker 01

  He now gets an email while he's on the floor for Opus at $62.99. He yells, guys, Opus at $62.99.

• 29:54Guy Raz?

  Oh, wow.

• 29:55Speaker 01

  Bert from Long Island's like, get the fuck out of here. I'm paying $9.5 bucks in Long Island. I'll take six. I'll take six. And they start, and then I'm getting emails saying, can you add my friend Bert to the list? Can you move? And so we are now in a viral loop and the world doesn't know it. Sherry Lehman's doesn't know it. K and L doesn't know it. Morrell's doesn't know it. Zacky's doesn't know it. Sam's in Chicago doesn't know it. Specs doesn't know it. Crossroads doesn't know it, but I do. I'm now spending six years mapping all the stores that I just mentioned to you, reading every single Wednesday, the dining section of the New York Times. And I'm memorizing the ads that all the stores are pricing, what their mix is. Are they Bordeaux heavy? Are they Napa heavy?

• 30:39Guy Raz?

  Wow.

• 30:40Speaker 01

  And I'm mapping in my little brain. And so now I can see where I want to play in between and how I can attack them on pricing and selection. And it, it just was that.

• 30:51Guy Raz?

  All right. So you're building this, this email list and you are starting to reach people, especially Wall Street people who know a deal when they see it. And you start to see revenue grow pretty quickly. By the way, is the store still, the physical store still called Shoppers Discount Liquors?

• 31:07Speaker 01

  The physical store became Wine Library in 1999.

• 31:11Guy Raz?

  Okay. So your dad agreed to change the name?

• 31:13Speaker 01

  Yep.

• 31:14Guy Raz?

  Better name, much better name.

• 31:15Speaker 01

  I think so.

• 31:16Guy Raz?

  And did it increasingly become more wine and less liquor?

• 31:19Speaker 01

  Yes. But that was not only because of how I was running the business. It was because that's what was happening in America.

• 31:25Guy Raz?

  Yeah.

• 31:25Speaker 01

  The the the average forty nine year old woman that lives in a high net worth neighborhood in nineteen seventy seven has a cocktail at night.

• 31:35Guy Raz?

  Yeah, right.

• 31:35Speaker 01

  The cliche forty nine year old woman in a high net worth neighborhood in nineteen ninety nine and two thousand two has a bottle of wine.

• 31:43Guy Raz?

  So you're seeing this happen in real time and you guys are riding this wave and and I mean, how fast because you were your dad was doing four million in revenue a year in gross revenue, his net profit was low, relatively low. What kind of change were you were you starting to see when you, you know, start to sell people via the internet?

• 32:04Speaker 01

  We went to um, we went to ten million in ninety nine and seventeen point five in two thousand and twenty eight point three, you know, I mean, it was we went from four to sixty five and sixty to sixty five in a blink, you know?

• 32:20Guy Raz?

  Wow.

• 32:20Speaker 01

  That was the first culture shock of my life because everything changes when something like that happens.

• 32:27Guy Raz?

  Yeah, and your dad was making serious money, big money.

• 32:30Speaker 01

  Yeah, but to my dad's credit, he was making big money, but you know what he decided to do? He decided to buy the Burger King next door, which just went out of business, which is unheard of, and then he decided to build a forty thousand square foot store as if he was building the Taj Mahal made out of mahogany and stone. So my dad had the opportunity to make a lot of money and take it off the table. What he chose to do was to pour it back into the business. Something that is still to this day, one of the great life lessons for me. I think the reason I have such a big business is I was born in an ecosystem that says, don't take the money out and buy a boat, put the money back in to build a bigger business.

• 33:13Guy Raz?

  Yeah. What what were you? I mean, I'm trying to if you ask me the question, what was I chasing in my twenties? I don't quite know. It may have been a combination of of recognition or or proving something. Probably there was some insecurity that I was chasing to prove that I could do these things. What what do you think you were chasing in your twenties when you were working so hard? Was it was it money? Was it a was it a number? Was it what was it?

• 33:38Speaker 01

  What I was chasing, you know, it's really funny. The numbers thing made me laugh that we just talked about earlier was definitely not a number. Numbers are just like a very quick way to tell a story.

• 33:47Guy Raz?

  Yeah.

• 33:48Speaker 01

  I could I never had a goal. I to this day, I've never had a goal of like, we're going to do this. I don't even think that way. In my twenties, I was chasing one feeling. God, you gave me the best parents in the world. You also gave me this talent. I have this incredible relationship with time. I'm patient. I am going to give everything I've got for this next decade to my parents who brought me to this country, who loved me, who gave me self-esteem, who gave me work ethic and accountability. I was so emotionally intelligently charged that I knew it. And I said, you know what I'm going to do? I'm going to give my prime youth years fully to my parents, and then I'm going to go and do my own thing.

• 34:31Guy Raz?

  So in your twenties, because in your twenties and you were really grinding away. I mean, you were totally, what, seven days a week, 12 hours a day, working at the store?

• 34:41Speaker 01

  Yes, I worked, you know, it was a retail store. Saturday was the biggest day by a country mile. So Saturday was seven to 11, because I had to get there early. Seven to 11, those are insane hours.

• 34:53Guy Raz?

  Did you have friends? Did you hang out with people or not really?

• 34:55Speaker 01

  I, my friends became my employees. And by the way, that's my life now. My friend group always circles around what I'm doing because I enjoy it too much.

• 35:06Guy Raz?

  In, in 2006, you launched a YouTube show, Wine Library TV. New York Times wrote a review of this show, like a two years in. And I just want to read what they wrote because it's so funny. It's actually a very positive review of the show. But the opening line is, "When the refined British wine writer, Jancis Robinson, joined the frenetic Gary Vaynerchuk last fall on his video blog, Wine Library TV, it was as if Helen Mirren had shown up on an episode of Dog the Bounty Hunter." I love that so much. It's such a great lead. And it's true. I mean, here you are, you're this young guy shouting about wine, and you know, Jancis Robinson, and you know, these, and she's probably the greatest wine critic on the planet.

• 35:51Guy Raz?

  But, you know, some, and initially, I have to imagine, people in the wine world just thought, who is this, who's this bozo?

• 35:59Speaker 02

  Hello everybody and welcome to Wine Library TV. I am your host Gary Vaynerchuk and this my friends is The Thunder Show aka the internet's most passionate wine program.

• 36:11Speaker 01

  I feel like I do wrestling promo videos in perpetuity, but I had the ambition to make it possible for people that were more casual to be influential voices in the wine world because I thought it would be good for the wine world.

• 36:27Speaker 02

  Very elegant, very structured, almost like a hot dog flavor in the mid palate. I know, stick with me, I'm sorry, but a little hot doggy, little gamey-ness, meatiness.

• 36:36Speaker 01

  And all the people that thought I was downgrading wine, not holding it up to the standard that it deserved, they didn't realize that I was creating wine drinkers and interest at scale. And what first initially shook the wine world was not only the fact that I was out of control and talking about wrestling and football and all the things the wine world would never want to be done, especially 15 years ago, but what was happening was I was also showing that I actually knew what I was talking about, which really confused a lot of people. And then most of all, the one that completely was the big one, I was panning wines that we sold.

• 37:10Guy Raz?

  You were panning them, you were saying they're terrible?

• 37:12Speaker 01

  I was saying things like, "How in the world does this winery believe that they can pass this wine on us for $55 when on a blind tasting it's a $13 wine and they're hosing us because they have the word Napa in their wine?"

• 37:26Guy Raz?

  Wow.

• 37:27Speaker 01

  And there was three reasons why that blew people away. A, everybody in my company, from my dad down, in the first year or two, thought I'd lost my mind.

• 37:37Guy Raz?

  Right, these are people you're buying wine from.

• 37:39Speaker 01

  Well, that's the next part. The insular industry had a real problem because my friends would call me and they're like, "What are you doing? You know, you've been buying wine for me for 15 years, we're friends, you stayed on my couch in Napa." I'm like, "John, I love you, I can't lie."

• 37:58Speaker 01

  It's over if I do. I remember that being the first two years, just a sheer, "Why are "you doing this?" And I remember thinking, "How do people not understand why I'm doing this? If I'm shilling up here, or not telling my truth, I'm one moment away from being finished." I always thought, Guy, that if somebody showed up to a dinner, or an event, gave me a glass of wine, without me knowing what was in it, tell me what I thought, and if I didn't say good or bad, you know, if I said, "Oh, this is delicious," and they're like, "Ha ha, you said it was garbage!" Like, so I was so scared of that, that I just always said what I said.

• 38:33Guy Raz?

  So, this is interesting, because as you're, I mean, this is like, you know, this is a time when, when news, the news media would, would sort of scour the internet for interesting things, and say, "Oh, there's this thing called YouTube, and, and here's this guy, and he, he does a wine show on this thing called YouTube." And so you started to get invited, onto like, the news, and you got invited to the Conan O'Brien Show, and, and I have to assume that you were sort of seen as this curiosity, "Here's this, this wine guy who's got a video show on, on the internet."

• 39:02Speaker 01

  Hundred percent. And I also was using Twitter and Facebook, and MySpace, to promote the show.

• 39:10Guy Raz?

  Yeah.

• 39:11Speaker 01

  Which started the process of me understanding this new medium.

• 39:13Guy Raz?

  What's so interesting to me is that you are building up a, a profile, a brand, around yourself, as a wine guy. So, so most people, and this is like, 2006, 7, 8, 9, 10, they're thinking, "There's Gary Vaynerchuk," if they knew who you were. "He's the wine guy. He's the guy who talks about wine."

• 39:34Speaker 01

  That is absolutely correct.

• 39:36Guy Raz?

  And normally, that is who people stay, for the rest of their careers. Did you think, at the time, "That's who I'm gonna be?"

• 39:44Speaker 01

  I thought that I am a wine guy. You know, I have this wine store, I have this wine show, I'm a wine guy. When I started putting out a little business content in 2009, and every comment said, "Stay in your lane, wine guy. What do you know about business?" That's when I was like, "Wait a minute, these people don't realize you can be a wine guy and a businessman." It was the first time I realized, oh, America is obsessed with narrow and/or not wide and both.

• 40:18Guy Raz?

  Yes.

• 40:19Speaker 01

  I couldn't wrap my head around it. I was like, why are they telling me to stay in my lane? I was a business guy before I was this wine guy they know. I was very confused. I was like, no, no, I built this business, this big business with not a lot of money. We didn't get cash infusion. We didn't raise capital for Wine Library. I exploded it from the dirt with my skills and work ethic and wait a minute, they think I'm a wine cartoon character? I, of course, I can talk about business. I'm a businessman.

• 40:49Guy Raz?

  When we come back in just a moment, how Gary throws an impromptu party for 500 people in Austin, Texas, and how that party helps him evolve from a wine guy into a marketing guy. Stay with us. I'm Guy Raz and you're listening to How I Built This.

• 41:17Guy Raz?

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• 41:59Guy Raz?

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• 42:44Guy Raz?

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• 43:29Guy Raz?

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• 44:13Guy Raz?

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• 44:54Guy Raz?

  Hey, welcome back to How I Built This. I'm Guy Raz. So it's 2006 and Gary has launched Wine Library TV on YouTube, what he calls the first ever video wine blog. And when he's not doing that, he's finding out everything he can about this new media ecosystem that he's immersed in.

• 45:14Speaker 01

  I started really getting into Silicon Valley startup Web 2.0 because I was using it to build Wine Library TV. And then YouTube sold to Google for $1.7 billion, which at the time-

• 45:28Guy Raz?

  Was crazy.

• 45:29Speaker 01

  Yeah, I mean, that would be like waking up tomorrow and hearing that TikTok sold to Amazon for $1 trillion. The kind of number that would stop you. We're in billions now. So it was one of those moments. And so I read everything that I could on the internet. And time and time again, the article said, "Angel investor Ron Conway is set to make this on this..." And I said, you know, now I'm 32 and I'm like, you know, I've always thought I was a businessman.

• 45:54Guy Raz?

  Yeah.

• 45:55Speaker 01

  But I have something. This dot com, like I was right about email. I was right about Google AdWords. I was right about YouTube. I was, maybe, maybe I should be an investor.

• 46:05Guy Raz?

  And when you, when you started to hear about people like Ron Conway, and you said, "I want to be like that." I mean, where did you go?

• 46:11Speaker 01

  I'll tell you.

• 46:12Guy Raz?

  Who did you, yeah.

• 46:12Speaker 01

  I don't go through the pattern of, "I want to be like that." I go into like, "Angel investor, enter, Google." What the hell is an angel investor? What is investing? What's 20%? Wait a minute, you borrow money from other humans? Like, you know, I was in a cocoon. I surely knew how champagne was made, but I had no idea of investing. I didn't take economics class. I didn't even pay attention to Wall Street. So I said to Eric Kastner, who was my lead developer, and no question, one of the most influential people in my career, because he was the developer that showed me Web 2.0.

• 46:46Guy Raz?

  And he was working with you on Wine Library?

• 46:48Speaker 01

  Yeah, he was my lead developer for Wine Library dot com. But our office was half the size, a third of the size of the office I'm sitting in now, which is not very big. So I sat with him and I would look at his screen and be- Like, what's that? He's the guy that made me stop searching stuff on Yahoo to go to Google. So what ends up happening is Twitter comes out and I really am intuitive to it. Like, it just really blew my mind and I got very aggressive on it. I did a very good job. I'm good with people. I figured out how to translate that to the internet. And I'm like, this is it. This is it. This is, I gotta do more of this. And now I find my first passion since wine.

• 47:27Guy Raz?

  Which is the internet?

• 47:28Speaker 01

  Which is this new internet, Web 2.0. So anyway, nonetheless, now I know I want to know Web 2.0, so I want to go to a conference. So me and Eric Kastner go to London to something called the Future of Web Apps, FOA.

• 47:42Guy Raz?

  This in 2000, this in 2007?

• 47:45Speaker 01

  Six, seven. I want to, I want to give you the right answer. But then we sit in the crowd and I'm listening and I'm blown away by these people. And they were nice and they were like hippie, techie, a tiny bit business. But I was like, this is it. And then I went to South by Southwest and I threw a wine party, I remember, at South by. Uh, cause I just sent wine down there just in case I would need it.

• 48:11Guy Raz?

  And you what? You got, and you, you had like a hotel suite and you just advertised it or something?

• 48:15Speaker 01

  I, I, I wasn't in that place in my life. So instead of throwing this wine party in the suite, I charmed the person at the front desk of the Hilton in Austin. And said, can I just use this room over here? And she was like, sure. And then I tweeted out, by the way, I had 5,514 is what I remember. Followers on Twitter at the time and everybody at South by, they thought I was the Kardashians.

• 48:40Guy Raz?

  Right.

• 48:40Speaker 01

  Like, they couldn't believe how many followers I had. This is how early it is. And so like 500 people showed up to this Hilton and like.

• 48:47Guy Raz?

  500 people came to a conference room at the Hilton to have free wine?

• 48:50Speaker 01

  It was actually like the closed restaurant, so there was enough room, thank God. It was a scene. Actually, I'm going to Google after this interview the photo, because the photo exists. And that was kind of my coming out party.

• 49:03Guy Raz?

  And it really was, I mean, in the sense that it kind of catapulted you into the tech world, right? I mean, Twitter and Facebook were pretty young at the time, and I guess after that party, you were kind of able to walk into those places and meet people.

• 49:17Speaker 01

  Yeah. A month later, I flew to San Francisco and met Chris Messina for a coffee.

• 49:25Guy Raz?

  And Chris Messina, just to be clear, he's the guy who invented the hashtag.

• 49:28Speaker 01

  That is correct. He was absolutely the guy who tweeted, "Let's all use a hashtag to give context to our tweet." He was a connected guy in the game as a developer. The hashtag's been around. He kind of commercialized it as a proxy. I'm sure that the hashtag was being used in nerd ICQs and other things, but anyway, while I was having coffee with him, he's like, "Do you want to go to the Twitter office? It's right down here." I'm like, "Of course." We go there, there are nine people there. There's Jack, there's Ev, and I get to talking to Blaine Cook, the original CTO. A year later, Blaine's at South by, 2008 now, maybe. He's leaving Twitter, he tells me.

• 50:09Speaker 01

  Not only is he leaving, but he has to sell all his shares because that's how religious he is about his passions and ideological points of view. The next thing I know, I am negotiating to buy a portion of Blaine Cook, the original CTO's founder's shares of Twitter, and now I'm in the game.

• 50:28Guy Raz?

  And this is based on the money that you, because you, I mean, in your 30s, you start to make some money because of the wine business.

• 50:36Speaker 01

  Here's the hugest part. I never made more than $80,000 a year, even though I built this huge business because it's a family business and we don't take salaries and I don't own the business and I don't have any...

• 50:45Guy Raz?

  You grew it to $60 million, you're making $80,000 a year?

• 50:48Speaker 01

  That's right.

• 50:49Guy Raz?

  Okay.

• 50:50Speaker 01

  Because my dad was too, because that's like, and again, this is where true first-generation immigrant family businesses will understand that I'm dead serious about this. Like, an immigrant business that is built by a certain type of immigrant that picks business over luxury.

• 51:05Guy Raz?

  Yeah.

• 51:06Speaker 01

  Right? My dad drove a truck that had a hole in the bottom of it.

• 51:09Guy Raz?

  Right.

• 51:10Speaker 01

  Like, he's the anti-show-off.

• 51:12Guy Raz?

  But how did you have money to buy into Twitter?

• 51:13Speaker 01

  I put $34,000 into Twitter, okay?

• 51:17Speaker 01

  The reason I had that, and then I also put money into Facebook and then put money into Tumblr. Those are my first three investments.

• 51:23Guy Raz?

  And this is simply because you went out there and you had met people?

• 51:27Speaker 01

  Yes, because you have to understand, this is 2006, 7, 8. It was early. People didn't know what Facebook and Twitter were.

• 51:34Guy Raz?

  It wasn't huge amounts. Well, these are still big, but this was in like millions of dollars you had to spend. These were in the tens of thousands of dollars.

• 51:41Speaker 01

  Correct.

• 51:42Guy Raz?

  And that's all you had?

• 51:43Speaker 01

  That's right.

• 51:43Guy Raz?

  And then I guess people started to get to know you as like a social media presence, right? Like a person with opinions about about social media. And there was a video that you posted at one point, I think on YouTube, was it? Is that right?

• 51:58Speaker 01

  Actually, it was on Vidler, V I D D L E R dot com, a platform that was competing with YouTube at the time.

• 52:04Guy Raz?

  Right.

• 52:04Speaker 01

  It was a single video I made titled "Facebook Should Worry About This Thing Called Twitter."

• 52:12Speaker 01

  And it was me laying on a couch in my house with my, remember the flip cam?

• 52:17Guy Raz?

  Oh, yeah.

• 52:17Speaker 01

  Yeah. So I take the camera to my face and say, "Facebook should be worried about this thing Twitter." I've been on Twitter, this new thing. You gotta check it out. And I gotta tell you, I know my brother and all the college kids are on this thing Facebook, but there's something here with Twitter. And a couple of weeks later, I get an email from Dave Morin, who was a top executive there.

• 52:43Guy Raz?

  Sure, at Facebook?

• 52:44Speaker 01

  At Facebook. And he says, "You don't happen to be in California on this?" I was like, "Yeah, ironically, I'm coming. Of course I was gonna come and talk to Facebook, right?" So I go and there's 200 people there, 150. I mean, the company was tiny.

• 52:59Guy Raz?

  And by the way, when you went to Facebook and they asked you to just speak, did you like write a speech or did you just kind of come with notes? Like, did you like sit down and start preparing something?

• 53:10Speaker 01

  I'm pure improv. No notes, no decks. And so after that moment, I just started making business videos in the first. Fifty business videos of random ideas I had about social media. We called it web 2.0 back then. Were met with 90% comments, stay in your lane, wine boy, stay in your lane.

• 53:27Guy Raz?

  Yeah, and you were putting this up on YouTube.

• 53:29Speaker 01

  And Viddler, because it had tagging and you could click to the part of it. And I was filming myself at the flip cam for the business stuff. Eric Castner and Chris Mott, they would just, you know, click the button on the camera. I would do my thing, no editing, no lighting, no microphone. And they would go upload it and post it.

• 53:49Guy Raz?

  And this is all happening, I guess, around like 2009. And I guess right around this time, you decided to start a digital ad agency, like a branding agency, which would become VaynerMedia.

• 54:02Speaker 01

  That's right.

• 54:02Guy Raz?

  But you were still doing the wine business at the same time. Is that, is that right?

• 54:06Speaker 01

  Yes, from 2009 to 2011, I moonlighted in both businesses because Wine Library wasn't ready for me to leave. And VaynerMedia wasn't big enough for me to be forced to. And so I was, you know, doing both.

• 54:20Guy Raz?

  And the idea with VaynerMedia was, look, I know this space. And I, like, I'm a native in this space. I can help brands figure this out.

• 54:27Speaker 01

  Yeah, the idea in 2009 was, how does Pepsi and Campbell's and the NHL still not have a Twitter and Facebook account? It's 2009.

• 54:34Guy Raz?

  Right.

• 54:34Speaker 01

  I already knew that I wanted to work with my brother, who's 11 years younger than me, AJ. Maybe I should start a company. AJ is graduating now. I don't have a great idea. You know, we might want to do this fantasy sports thing. That would have been good. We might want to do this deal of the day, Groupon, living social thing. That probably would have been good. Like, the ideas were good, but VaynerMedia was practical. Gillette paid us $60,000 for a project and we thought that was a trillion dollars.

• 55:00Guy Raz?

  Yeah, I'm sure.

• 55:01Speaker 01

  And so we got to work. And what we knew was, we wanted to be in this space. We wanted to be able to pay our rent. And we wanted to be able to learn. And that nobody loves a good halftime adjustment more than me. That whatever we were doing, helping brands do social, it didn't matter to me to overthink what 13 years from now is going to look like, because I would figure it out along the way. And that's why it was so easy to start. I think people are so rigid.

• 55:33Speaker 01

  So in need of predicting the future that it cripples them from actually doing.

• 55:38Guy Raz?

  I agree. So you and your brother start VaynerMedia and you start to get some accounts? And you basically were using the playbook that you had developed with the wine business?

• 55:48Speaker 01

  Yes, the playbook was put out content that people actually want. Don't do television mentality where you're forcing things down. Listen to the comments, engage in the comments, follow people back. Use context of culture. So, hey Pepsi, you know what would be really cool? Is if you follow Friday normal people, that would be stunning to people. And that's what they did. Victor Lee, who was at Hasbro, hey Victor, I know you're launching this new Furby, the reboot of Furby, which was big a decade earlier. Why don't we do it on a Facebook fan page instead of television? And we post a Furby comment that says spell your name backwards by writing the words, spell your name backwards in backwards? So it was that kind of work that was working.

• 56:32Speaker 01

  It was internet native. And at the time, every brand was completely dismissing social media or trying to do print, radio, or television-like content on social media.

• 56:45Guy Raz?

  Yeah, this is the time, like 2009, 10, 11, where companies started to hire quote-unquote "social media gurus." Was that who you guys were thought of? Or is that like when people said, oh, we'll go to these social media gurus?

• 57:00Speaker 01

  Yes, but what was different was even though I was the guru of the guru because of Gifted Gab, had the most Twitter followers, my book was a New York Times bestseller. I knew then that I didn't want to be Gary Vaynerchuk the guru. I wanted to build a business. So you would be hiring VaynerMedia, not Gary Vaynerchuk. Of course I would come to the meeting, of course I would put my strategies, of course I would talk to you. But I believe a lot of people in ad world thought that this was like the Gary Vee Show, when it never was and it never will be.

• 57:32Guy Raz?

  Let me go back to, you mentioned your book and I want to, I want to talk about that for a sec because, I mean, you were, you got a book contract, I think like a 10 book deal, to write books about, I guess about entrepreneurship. Your first book was called Crush It, Why Now Is The Time To Cash In On Your Passion? And, I mean, how did you start to get attention that enabled you to attract the book deal?

• 57:53Speaker 01

  There was a web 2.0 conference at the Javits Center in New York. And I give this talk, and the talk was basically Crush It, which is, does everybody understand what's happening here in 2007? Like, this is it. We can do stuff. You could do a blog about Smurfs and make $100,000. Like, that's literally what I said. I said, "Smurf it up." I said, "Do something about Alf." I was like, "I'm doing it about wine." If you read Crush It today, I basically laid out 14 years ago influencer marketing. And it landed, and by the time I got to the green room where I had my phone, because I didn't even bring it with me on stage those days, I had three emails from P engnum, Putnum, from Wiley, from like publishers saying,

• 58:34Speaker 01

  "I'm in the crowd right now. Can you turn what you just said into a book?"

• 58:39Guy Raz?

  Wow. This is around the time when Tim Ferriss also released Work Week.

• 58:44Speaker 01

  That was about a year earlier, maybe two years earlier. I'm not sure exact timing. And hence, here comes Crush It, which is, you know, the economy's crap, but you can do it. You can be on the internet. You can start a vlog or YouTube show.

• 58:58Guy Raz?

  And you were, in 2008, you were not a rich guy.

• 59:00Speaker 01

  No.

• 59:01Guy Raz?

  You were making a living, but you were making a living from, from the wine business, but it was your passion.

• 59:05Speaker 01

  Yes, but book writing was my most lucrative part of my life.

• 59:09Guy Raz?

  Lucrative, yeah.

• 59:10Speaker 01

  In 2009, 10, 11, 12, that's where I made most of my money.

• 59:14Guy Raz?

  Yeah.

• 59:15Speaker 01

  Because I was making nothing at VaynerMedia. I was still making 80. And maybe, you know, to be fair, I might have gotten to 100 by then at Wine Library just because at 30, I got a little testy with my dad of like, "Yo." I need some more money.

• 59:27Guy Raz?

  Can I get $100,000? Yeah. So you and your brother are building VaynerMedia, and it's growing. And then in 2014, you're still running VaynerMedia. You helped cofound Resy, the reservation platform. And did you guys raise money for that, by the way?

• 59:42Speaker 01

  We did through the fund that I started, VaynerRSC. And so we incubated Resy in that fund at some level.

• 59:50Guy Raz?

  So you didn't have to answer to investors who were like, well, how are you going to do that and this?

• 59:53Speaker 01

  I was the investor in that scenario.

• 59:55Guy Raz?

  Yeah. As you, I mean, as you kind of were growing VaynerMedia and building it out in different extensions, and then started other things, what about your personal life? Did you get married? Did you like?

• 1:00:09Speaker 01

  Yes, married, two kids.

• 1:00:11Guy Raz?

  How old are your kids today, by the way?

• 1:00:12Speaker 01

  11 and 8.

• 1:00:13Guy Raz?

  Yeah.

• 1:00:13Speaker 01

  And so, you know, like, people think, because I talk about work ethic as an important variable, that I'm trying to burn myself out and die at 40. Like, people are very literal. But, you know, I come from the old school, right? Like, my family life is like, that's like mine. That's important to me. I come from real family dynamics. And it's very easy for me to have that, prioritize that, value that. So, yeah, I mean, like, I live like a real life. I'm not a reality TV star.

• 1:00:50Guy Raz?

  When we come back in just a moment, Gary talks about his latest all-consuming passion, an NFT project called VFriends. Oh, and did I mention? He wants to buy the New York Jets. We'll talk a little bit about that, too. Stay with us. I'm Guy Raz, and you're listening to How I Built This.

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• 1:02:51Guy Raz?

  Hey, welcome back to How I Built This. I'm Guy Raz. So we're already up to the present day. And on the day we did this interview in early May, Gary was gearing up to launch his latest project. It's called V Friends, and it's a community for buying Gary's own brand of NFTs, non-fungible tokens, which are basically unique pieces of digital property. And to build V Friends, Gary's team created about 10,000 electronic trading cards that can be redeemed for real things in the real world, like, say, a fishing trip with Gary. And he believes that if they do it right, VFriends could be a model for how other people could get into NFTs.

• 1:03:37Speaker 01

  And I believe that it will be the project that every celebrity, influencer, author, podcaster, expert, personality, human will look at as a blueprint of how to do an NFT project properly. For me, if this thing does $30 million in Ethereum or a dollar, if it becomes the blueprint that I just said I hope it is, or doesn't, it's completely irrelevant. Since January 7th, it is the only thing I care about, to try. I have to try to launch this thing. I put in hours and hours of thinking and work, but also gleaned off of 25 years of experience, off of the back of a decade plus now of building a community and knowing how to do better for them than me. And in a world right now where everyone's

• 1:04:22Speaker 01

  putting out an NFT project as a gold rush for a quick dollar, I'm building something that's going to benefit my community. That's not anything other than deep curiosity if I can pull it off.

• 1:04:34Guy Raz?

  Right. I mean, if you can pull it off, because there are, you know, there are skeptics, right? There are people who think that the NFT concept is super risky, like maybe not a good investment of time or money.

• 1:04:46Speaker 01

  Yeah, I mean, I think 99% of the projects that are being launched right now are gold rushes, and they're going to be projects that fail. And people are going to buy tokens from celebrities, leagues, different things, and the price is going to go down. And there'll probably even be an NFT winter, call it a tipping point, next year. This, I don't know when. That I don't know. But what I know is supply and demand, and what I know is human psychology, and what I know is pattern recognition. And then, what's going to happen, guys, is internet 1999. The stocks declined because those companies were built on gold rush greed. But the technology changed our lives forever. NFT technology is going to change our lives forever. This 12 to 24 months will create incredibly bad projects that

• 1:05:30Speaker 01

  don't bring back value to the person that supported it. But I plan on making my project, for example, the Amazon and eBay of that era.

• 1:05:40Speaker 01

  Amazon and eBay were during that March, April crash of 2000 stock. And if you were smart enough to see the bigger picture and bought those stocks for dollars, very nice things happened.

• 1:05:52Guy Raz?

  Yeah.

• 1:05:53Speaker 01

  And that's what's gonna happen again.

• 1:05:55Guy Raz?

  Gary, it kind of makes my head spin hearing, hearing all of this because this NFT project is like one of many businesses you have going on right now. I mean, I think, I mean, you've launched so many companies and, and sold at least two. I mean, I think, uh, Rezzy, you sold to Amex, Empathy Wine, direct to consumer wine business, and then sold that. But you've got VaynerX and you've got digital content production studios and you've got a, a talent agency, a sports agency. And I wonder whether you have to do all of these things. That it's like stimuli, that you can't, you, you have to keep moving, creating, right? Because some people would say, how do you do all that stuff? How do you focus on all those things? It's impossible.

• 1:06:36Guy Raz?

  But I wonder whether you actually have to do it to, to feel alive.

• 1:06:41Speaker 01

  A hundred, you, you're absolutely right. To me, when people are like, how do you do all those things? I'm like, how would I ever focus on one thing? Now, I love focusing on one thing. It is a game for me. I don't mind losing. Nobody talks about Vayner Live, right? Or Vayner Experiences, that was a division.

• 1:06:59Guy Raz?

  Those failed.

• 1:07:00Speaker 01

  Vayner Sampling, I still want to do it. Hip Hop at Lunch, dead. The first version of the publishing company, dead. So I lose a lot. I just don't care.

• 1:07:12Guy Raz?

  Hmm. I remember interviewing Richard Branson a few years ago on the show and, you know, talking about Virgin Cola and some of the other virgin vodka, just, you know, failures that, but, but he tried them.

• 1:07:23Speaker 01

  Yeah.

• 1:07:23Guy Raz?

  I mean, he must be somebody, yeah.

• 1:07:25Speaker 01

  Because it's more, it's more fun.

• 1:07:27Guy Raz?

  Yeah. All right, I want to ask you about the Jets. You're a lifelong fan of the Jets. You've been very open about wanting to buy them one day.

• 1:07:33Speaker 01

  Yes.

• 1:07:34Guy Raz?

  What does the Johnson family think about this? Do, have they ever, have you talked to them about this?

• 1:07:38Speaker 01

  I've never had a conversation with Chris or Woody Johnson about this, mainly because I don't like audacity.

• 1:07:43Guy Raz?

  You don't like audacity?

• 1:07:45Speaker 01

  Stick with me here.

• 1:07:45Guy Raz?

  Wait a minute. You've been publicly on the record saying you want to buy the Jets.

• 1:07:50Speaker 01

  Me sharing my public dream feels natural to me.

• 1:07:54Guy Raz?

  Okay.

• 1:07:55Speaker 01

  Me rolling into a meeting with the Johnsons where I'm nowhere close to being able to purchase the New York Jets feels audacious. And so my greatest joy is the hunt to buy the New York Jets.

• 1:08:09Speaker 01

  Would I like it to happen? Sure. It has absolutely been a fun goal of mine. It sucks because I know I'm patient and I know how I'm going about doing it, which makes me feel that I'm gonna get it done in 25 to 27 years. The part that bothers me is like, how deep I want my parents to be there? You know, can I, can I, that's tough. Because I know I won't deviate from my process, otherwise there's no chance that I get it. But I have this ticker that I'm not in control of. And obviously, I'm not in control of a trillion things, but I'm pretty sure if I pull that off somewhere in 25 years, that 40 years of this energy yelling about it, and then

• 1:08:51Speaker 01

  it actually happening, is probably good for a Disney movie, and why not?

• 1:08:56Guy Raz?

  Here's something I'm interested in, which is, and I've talked about this before, which is, I don't engage in social media too much. I do it, and I've got, you know, I don't have masses of followers like you, but I don't, it doesn't feel good when people are cruel or mean. And, you know, you see this with some celebrities, they'll drop off Twitter after a while, because it just can't take it anymore. You get a lot of hate on social media, because you've got millions of followers across your channels. Does it ever get to you?

• 1:09:29Speaker 01

  I'm a human being, right? You know, somebody decided to take time out of their day to spit venom at me, and I would never in the world think that that was a use of time that would be interesting to me, even if I disagreed with somebody or didn't like someone. So first, I think, where is that person? And that doesn't mean I think that person sucks or should be deleted, I don't block people. It's just a very interesting curiosity, intrigue of, man, that sucks. Like, A, let me look at what I posted. Did I do something there that would so engage someone to do that? B, there's a very big part of how I handle this.

• 1:10:14Speaker 01

  I believe that a lot of my friends who aren't able to handle it, which is many, enjoy the accolades too much.

• 1:10:23Speaker 01

  I believe one of the reasons I can deal with this is I can't hear them cheering for me, which allows me to deal with the booing. If I disappear tomorrow, God forbid, I'll get nine nice hours on social media of people sharing clips if I even affected them. And then everybody will move on their daily life, except for a very small group of people. When you realize you mean nothing, but you aspire to mean as much as humanly possible, you create a very interesting perspective framework that makes a lot of things easy.

• 1:10:59Guy Raz?

  I once asked Jimmy Fallon in an interview, how does he deal with the just being on all the time when he's in public? Like, you know, because he walks to work, right? From his apartment and he's walking down the street and people are high fiving him and then he goes to a restaurant and people are kind of always around him. And I was at an event with him and he was just getting mobbed. And he loves it. He loves it all the time. It's just so natural. He loves talking to people and it's part of what makes him so approachable. But I am an introvert, so when I see that, I'm like, oh, my God, I am, I need to just go into a room for a while by myself. Do you ever want to just jump off the hamster wheel for a couple of weeks and just not be around people?

• 1:11:42Speaker 01

  My answer is the same as Fallon's. I love it. The airport, the cab, the high five, the Jets games. I love it. You know why? I can't believe it. I'm so grateful. And by the way, I'm not a comedian. I'm not a supermodel. I'm not an athlete. People like me because of things I'm saying that I'm hoping will help them or giving out information that did help them. I figure out TikTok, I'm telling my people. I figure out NFTs, I'm telling my people. Like, I'm getting it not from fame, I'm getting it from someone admiring it or being grateful. It's an incredible energy. On the flip side, I actually completely understand why people, in first glance, in

• 1:12:26Speaker 01

  an Instagram feed of a 30-second clip at my height of a feeling and conviction, will be like, fuck this guy. But I also know there are people that walk around the world that are adored, that know as people get closer to them, they hate them more. I have the reverse.

• 1:12:43Guy Raz?

  And it sounds like the people that are your detractors, your view is like, come on, come meet me, come talk to me. You're not mad at them.

• 1:12:51Speaker 01

  I'm definitely not mad at them. I understand them. I'm a lot when the lights are on. You've never seen me and you see a 30 second video on Instagram where I dropped seven F bombs in nine seconds? And you have no context for me? And to your point, like even your reaction on my audacity, like I'm not confused what audacity and conviction and even disgusting word ego and all these things that people might think. But I just know the truth. Like I think of myself as an athlete. When I am on the field, I will do what it takes to win the game in the rules. But when the game is over, Guy, I'm going right up to my competitor who I tried to rip his fucking eyeballs out and saying, hey, how's Karen?

• 1:13:37Speaker 01

  And can I give you a donation to your charity? So when I see athletes at the end of a game hugging each other after they were bashing each other and I'm pissed because I'm like, don't hug them, they just beat us. I'm fucking angry as a fan, but I understand them, brother. Because even though I know I'm competing with people day to day or this and that, I'm on the field when people see me on social media. I'm on the field.

• 1:13:58Guy Raz?

  You are obviously super passionate about the new project that you're building around NFTs. And there will be other things. And you have this reputation of somebody who never stops working, right? Never, ever stops, constantly working, constantly on the go. First of all, do you think that's true? Because it seems to be true.

• 1:14:20Speaker 01

  No, I don't think it's true. I try to communicate. Here's the problem, right? No matter how many times I make a video, I can easily say with the same conviction as I've said everything else, guys, sleep eight, nine hours a day. Yet, even though hundreds of thousands of people will hear that. Somebody will come out and be like, "He sleeps four hours a day, it's not hell." Like, people see what they're looking for.

• 1:14:42Guy Raz?

  Right.

• 1:14:42Speaker 01

  You know, I am high energy because I'm passionate and excited and optimistic and enjoy it. And that comes through. I really like work and I am very addicted, no question, to the notion of legacy. I want to leave a mark, it's nice, why not? Why not? Why not try to give the world more than it gave you?

• 1:15:06Guy Raz?

  There's a renewed or a new kind of view on, and I hesitate to use this term because I think it's a lazy term, but for shorthand purposes, I'll use it, hustle culture. There's a kind of a new or a different perspective on it now. And there's a lot of criticism about, and now we get it about our show too, even though I don't believe that's what we do. You get a lot of criticism for promoting hustle culture. This idea that anybody can succeed and make a living off their passion. I know that's oversimplifying, it's not what you say.

• 1:15:41Speaker 01

  No, no, it's not what I say, not only it's not what I say.

• 1:15:44Guy Raz?

  Right, it's not what you say, but you get...

• 1:15:46Speaker 01

  Well, I mean, everybody gets, right? I say in 2008, when Krusha came out, "The economy's crap, everyone lost their jobs."

• 1:15:56Guy Raz?

  Yeah.

• 1:15:56Speaker 01

  "You have the ability to use the internet, to build a business around things you like." That was factual in hindsight.

• 1:16:04Guy Raz?

  Yeah.

• 1:16:05Speaker 01

  It doesn't mean that, I'm not, guy, I'm not the secret. If you just work, it will, like, it's just not true. And nor have I ever said that. People are so incredibly selective. I don't even use the word hustle anymore, a word that I loved my whole life.

• 1:16:19Guy Raz?

  Yeah.

• 1:16:19Speaker 01

  Because I believed in grit and I believe in tenacity. And I believe that work ethic is one of the variables of success. But nobody read the parts of the book where I say, "Make $60,000 a year and be happy." Let there be no confusion. I'm not driven by people making money, buying BMWs, having, you know, private planes. But I think there is a certain group of people on earth that love building businesses, the way people love golfing, love being a mother, love being a doctor, love. And I'm one of those people.

• 1:16:54Guy Raz?

  Yeah. Do you, when we think about your, your journey from, you know, childhood and Queens and your dad opening that liquor store and... The work you did and where you kind of came to now, how much of that do you attribute to you, your values, your hard work? And how much?

• 1:17:17Speaker 01

  Oh, a lot.

• 1:17:18Guy Raz?

  Do you attribute to luck?

• 1:17:20Speaker 01

  Well, it's tough. I worry that people use the word luck to eliminate accountability on their own efforts. And they give up and cease mental control and don't realize how much control one has in their lives. So I play very carefully with the word luck because I think people love to use it as an excuse engine. However, I think it's incredibly powerful reality. I mean, you know, to me, the luck starts and stops with Tamara Vaynerchuk. To be the firstborn son of that woman is the greatest lucky thing that ever happened to me.

• 1:17:57Speaker 01

  The way she molded me and navigated me, nothing in the outside world had any chance of competing with that.

• 1:18:06Guy Raz?

  Yep.

• 1:18:06Speaker 01

  Yep. You know, I've never said that before that way. I was in a cocoon of love and accountability. You're punished, you got Fs, but she made me feel like I could do anything. And so if you ask me what drives you right now, and I've only realized this in the last five years, which is why I'm like, oh, that's right, that's what I was doing in my twenties. I'm so damn curious about how good I am at this.

• 1:18:32Guy Raz?

  But it's interesting because when you say that and articulate that, right? If somebody read a transcript of you saying that without hearing the tone in your voice and the cadence, they might think, God, what a, that guy's full of himself. But when you say it and you hear it, it's clear that that's not how you're trying to express it. You are, it sounds like you're almost amazed that you just, that just came to you, you just.

• 1:18:53Speaker 01

  Gratitude. The way you just articulated it, if this was read, you're a douche. But if you listen to this with all the nuances of context, it feels right. And honestly, I like that. And by the way, could you imagine a better life? Could you imagine a better life?

• 1:19:11Guy Raz?

  That's Gary Vaynerchuk, CEO of VaynerMedia, author of Crush It!, co-founder of Resy, launcher of many, many other projects too numerous to name, and one day, possibly, the proud owner of the New York Jets. By the way, I had a great conversation with Gary at our virtual How I Built This summit back in May. He had all sorts of incredible insights about marketing and time management and lots more. So be on the lookout for that. It will be in your podcast feed on Thursday, August 5. And thanks so much for listening to the show this week. This episode was produced by Liz Metzger with music composed by Ramtin Arablouei. It was edited by Neve Grant with research help from Derek Gales. Our production staff

• 1:19:56Guy Raz?

  includes Casey Herman, J.C. Howard, Rachel Faulkner, James Delahoussaye, Julia Carney, Farah Safari, and Annalise Ober. Our intern is Harrison Vijay Choy. And Jeff Rogers is our executive producer. I'm Guy Raz, and you've been listening to How I Built This. This is NPR.