Gary Vee: USSR to CEO, the Immigrant Mentality, and Building Legacy | E133
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- You guys are gonna be blown away by this. We would sit there and watch people surf the web. Like, watch them. Like I stood there for two fucking hours before I got to get on the keyboard watching Pete from Maine and others get on the computer and do different things. And even then what was super interesting was everyone was scared to leave AOL. You just stayed in AOL. Like there was this browser, I remember it would just be like the World Wide Web and we're like, "We're not gonna click that. "That's too crazy."

I got finally on the computer at like 12, 1 o'clock in the morning. You know, I typed the two things that I knew, baseball cards and wine, out of a fucking movie. I literally remember seeing the reflection of my own face in the monitor saying, this is it. I just knew. Welcome to In Search of Excellence, where we meet entrepreneurs, CEOs, entertainers, athletes, motivational speakers, and trailblazers of excellence with incredible stories from all walks of life.

My name is Randall Kaplan. I'm a serial entrepreneur, venture capitalist, and a host of In Search of Excellence, which has started to motivate and inspire us to achieve excellence in all areas of our lives. My guest today is Gary Vaynerchuk, who is known to most as Gary Vee. Gary is a serial entrepreneur, angel investor, venture capitalist, public speaker, six times New York Times bestselling author, and one of the world's leading experts on the topics of marketing and social media.

He is the CEO of VaynerMedia, a full-service advertising agency that represents Fortune 1000 companies and which has more than 2,000 employees and 13 offices around the world.

He's also the co-founder of many other companies, including Gallery Media Group, the Sasha Group, VaynerSpeakers, VaynerCommerce, and VaynerSports. Gary, thanks for being here. Welcome to In Search of Excellence. It's so nice to be here. Let's start at the beginning, and I want to start with your dad. We'll talk about your mom separately. He moved. He was born in Bobrisk, USSR. He moved to the United States when you were three years old, didn't speak English, had no money. Talk to us about Arlene Newman and Bob Siegelman and the

big breaks that people can have when they move to the United States and how they influence this future? I, right off the bat, adore you because I've been very fortunate over the last decade. I've been interviewed a lot, a lot, a lot. The fact that you get to go to Bob Siegelman and Arlene means real homework has been done for that. That means a lot to me. And it's really nice to actually have a platform to give them some love because they're

My father was very inspired in 1971, four years before I was born, when Jack Siegelman, their parents, the father of Arlene and Bob, came back to America. Jack left the Soviet Union. Jack left the Soviet Union in the 20s, I believe, when he could still kind of get out right after the revolution. And Jack was my dad's grandmother's brother. And he was the only one that went to America.

And he had the brains of the family in a lot of ways. He saw it. He saw what was coming. He came, Jack is a much older man, came back to Russia in 71. And my dad was really taken aback by a statement when he just looked at my dad, who was 16 or so at the time, 18 at the time, and just said, you need to get to America. And it stuck for my father. There was an incident that happened in the Soviet Union that became world-famous.

focused on Walter Cronkite, big thing. And there was this deal made between Israel, Spain, and America with the Soviet Union to get some Jews out of the Soviet Union. Only a couple hundred thousand were able to leave in the late 70s. I was lucky enough to be a part of that. The way you would do that is there was an organization called HIAS that deserves a lot of credit. And you'd go to Austria, then Italy, then you would go anywhere. Many went to America, some went to Australia, some went to Germany.

While we were in Italy, we got a letter in the mail that Jack passed away. This was the person that was going to kind of look out for us when we came to America with nothing. When we get to America, it would have been very easy for Jack's kids, who were in their 50s at this time, very well off. Because Jack did very well for himself coming to America and did the American dream in the 20s, 30s, 40s, and 50s, 60s. Construction business? Construction business, predominantly. Okay.

It would have been very easy for them to look the other way, of their lost, lost relatives from the Soviet Union.

But Arlene especially was incredibly gracious to my father, got him his first car. And one of the things that Jack owned in his real estate empire was a small liquor store in Clark. So the organization that got us to America kind of put us up as refugees in a studio apartment in Queens. And my dad did a bunch of side jobs the first six months, but the break of...

him being a stock boy in that liquor store that Jack once sold that now Bob was really running. He was the older son, so he was kind of like the main guy, but Arlene was a very feisty, prominent sister, and so they really co-owned that empire or whatever they inherited from Jack, and they were doing their own separate things

And that is where my father's American dream was hatched from two bucks an hour being a stock boy to eventually being the manager of that store to eventually saving up money and buying a piece of that store from Bob. All in five years. Which is remarkable if you think about it. And so...

I mean, I think a lot of times people are like, "Gary, you would have never been here "if it wasn't for your dad." I'm like, "True, but my dad would have never, "if that's true, then my dad would have never been here "if it wasn't for Arlene and Bob. "And if that was true, then Arlene and Bob "would have never been in that position without Jack. "And if that was true," and so I think we all as human beings, self-made is a very funny thing because it's unbelievably true,

But it's also very contextual. It's like lucky. Lucky is very weaponized by those who do not want to do. But even though luck is very much timing, serendipity is very much part of anyone's story that builds something, it is clearly just one small ingredient of the outcome. And so,

Bob and Arlene were incredibly important to my parents and helped in many different ways. My name is Gnazzi. That's my actual name. Arlene literally named me by telling my parents, name him Gary. And so, you know, I think very prominent. Bob, unfortunately, passed away many years ago when I was just starting my career at my dad's liquor store in my 20s. And Arlene is still kicking. And I hope her family shares this clip with her.

So let's talk about your mom, Tamara, who also came from the Soviet Union, came here in no money, didn't speak English, had a tough life in the Soviet Union. Dad died at five years old? Mom died at five. And then dad went to prison for 10 years for being Jewish and went to the Gulag in Siberia. So talk to her about the influence that your mom had on you. You know, I would argue that my mom, you know, my parents are very influential in my life, like for many, but very for me.

And I would say my mom is probably the person that probably is the one who gives me the most fuel to tell everybody on the other side of these podcasts that you can do it. Please don't complain about silly things. Choose optimism. Because when I think about my mom's life, it's remarkable to think about the energy that she brings to the world. Much like I, in a lot of ways, am the emotional person

Rock of so many people around me my mom was that for everyone when I think about how little that rock was Watered, you know, it just it was in her it was her DNA She is the strongest person I know She's just incredibly strong and she made me very strong and you know, obviously just even already hearing how this interview is gonna go and

I'm sure you've seen how much I speak about her and how I revere her. And I admire her to the depths of my soul. And she was a perfect mother. She did plenty of things wrong, but everything that I hold near and dear, everything that I know is a core ingredient to why I'm successful. It's very easy for me to point to both of my parents, but

My mother had the luxury because my father, you know, something I admire about my father, we had so little, but my father was hell bent on allowing my mother to stay home and mother. And so through his 15, 18 hours a day of work ethic and with her talents in our household, you know, when I talk about anytime I'm brought up, even that intro, when I hear six time this or great this or whatever,

The accolades run right through me and it points towards them. And that makes me happy. Did they ever say the four words that I think are the most important four words in English language? I believe in you. A hundred percent. They said those words out loud. My mother, who was much more of a communicator in my life, not only did she say that, it was a constant currency in my life.

Like I would, I would, I would speculate if I can recall properly, there was probably not a day in my life between five and 15 where my mother didn't give me some sort of version of that. And not like checking the box. Like it was her natural communication and point of view on, you know, early on in my life. I remember just how often she said I had a golden heart. So anything I did that was nice for another person, um,

or for a relative or from my sister, it was always reinforced with your golden heart, you're special, you're a star. There was never a day where I didn't feel I was capable. And let's talk about in the second grade, you grew up without money and then she stayed up till midnight one night. Yeah. I mean, this is a very emotional story for me. It's why it's pinned as my main Instagram post on my account.

So, you know, I moved to Edison, New Jersey, which is amazing because it was an incredible place to grow up in the 80s. And, you know, how old are you? 55. So this is perfect. We grew up. One of my best friends is from there. From New Jersey or from Edison? Yeah. Edison. No way. Yeah. Peter Warman. Shout out to Peter. Peter.

We need to hang. So, you know, Peter will confirm this. Where did you grow up? Detroit. Right. And so did you play outside a lot? Played outside a lot. So we like, you know, this and I'm sure you think of this as a parent. I sure do. As much as my mom and dad raised me, Edison, New Jersey raised me. I mean, I've been saying it a lot lately because I just can't get out of my mind.

For the kids that are listening, there used to be a commercial at 10:00 PM when we were growing up that would air on network television that would say, "It's 10:00 PM, do you know where your kids are?" 'Cause our parents literally didn't know. We were outside all the time. You might forget to know if they even came home for dinner.

So I was raised by Edison Jersey and by my friends around me. And my friends loved football. Literally before we started this show, we were talking about football because I ran into Eric Godfrey and Robbie Turnick and Bobby Duffy and these kids that were playing football. And I became a huge Jets fan. And my friend Eric Godfrey had a number 24 green t-shirt. And again, this was a lower income family.

town in New Jersey. So it wasn't like a authentic custom made jersey. It was just a t-shirt with the number 24 on it. Didn't even have Freeman McNeil's name on the back, but it was just a t-shirt with the number 24 and another kid. I don't remember his name. He had an 85 and that was Wesley Walker. And so now we're playing football time. And I wanted, I wanted a Jets t-shirt too, a jersey.

We couldn't afford that. And my mom made it very clear. She's like, we're not buying one. $30 at the time. Right. And probably 10 with inflation. You know, you could probably get one at Kmart for 10 bucks or Bradley's. But we just did not. Like the only clothes we had as kids was the liquor t-shirts my dad would get as promotions from the store. Like literally the majority. I did not buy a t-shirt at

Until I was in college because every t-shirt we had was a liquor promo t-shirt There were eight of you in the studio apartment. Yes, my core family was - it was those those cousins my grandma they lived elsewhere we eventually moved at us it was just me my mom my brother my my sister and my brother came later in 87 but like the bottom line was the only money the only thing that money was used for was

until I was 12 was food and shelter. The occasional toy was a monster thing if me and my sister were to get a toy, a toy. I remember my brother was gonna be born in January of 87. I wish, I'm laughing right now because I know my sister's about to hear this line and she's just laughing. Hanukkah 86, Hanukkah 86.

was monstrous. My mom was overcompensating for the fact that we were about to have another child. And I got three wrestling figures and the wrestling ring. And I thought it was like,

You would have thought I got a Rolls Royce and caviar for life. Like it was just absurd. So back then, money was just for food and shelter and savings. It was all about saving money, which is talk about something that no one talks about anymore. Saving money was the currency back then, as you know, probably as a child. It was in the ether. Now it's not. Anyway, there was no thought of getting a jersey. And I was disappointed, as any seven-year-old would be.

And my mom would stay up to midnight for a week or two, or I don't know how long it took her, but she knitted me a Jets jersey and put my favorite number, at that time was five, still is, and I still have that jersey. It's got a number five, it's got my name Gary on the back, and it is my prized possession. And the reason why

When I take photos now, I put up the number five. It's just a little head nod to my mom, who is my hero. Did not having money motivate you to be successful? And what's your advice to kids who grow up with a lot of money who may not be as motivated? Because I've seen it both ways. Our summer intern program.

There's 32 kids, about half have money, half don't have money. And I've noticed throughout my career, a lot of the kids that have money, they'll say, oh, I don't need to work this hard or I'm unhappy in my job. I'm just going to leave and I'll find something else. It's a very complicated question, as you know. I'm sure based on your background and mine, we've given this a lot of thought, especially when you have children. And have done well. And your kids are raised in a different environment than we were. And you can't fake environment.

And to your point earlier, it's hard to be hungry when you're constantly fed. And money gives you optionality to be able to choose. I don't want to grind through this. And the ability to deal with adversity and to be comfortable in uncomfortable situations is probably the most important skill set one can learn if they want to enjoy life, period. Peace of mind and lack of anxiety matters.

and content are far more interesting than private planes and Rolexes and houses in Cabo. So what do I think? Do I think not having money motivated me to be successful? I don't think so. Let me explain. One of the things that's interesting about growing up in like Russia and then, or the Soviet Union and then Queens,

in like the housing projects and then Dover and then Edison, I didn't even know what money was. Meaning when everyone around you doesn't have shit either and you're pre-internet and you're not really watching a lot of TV, like you don't know. So when I think about that and then I think about, I definitely did not know we didn't have money when I was six when all I wanted to do was have a lemonade stand.

I definitely did not know. I actually thought we were good, like real good. We had, you know, my dad really grinded. And so like, I don't know, like we were in the mix. We weren't, there was kids that I went to school with that literally didn't have lunch money, you know, that wore the same clothes that smelled like I, like I grew up in a lower middle class. I wouldn't say ghetto or poor, but like poor for sure at first. So anyway, punchline being, um,

I did so many money-making activities long before I had any context of money or where we sat or what was out there or what was possible. And then even when I learned what a Mercedes was when I was 11, it never crossed my mind that I wanted one. I still have never had a real high-end car. What do you drive now?

Nothing. I have a driver, so that's even more ridiculous than a Cayenne car. But when I had money, I got a Jeep Grand Cherokee. And to me, I never thought of a car or a watch or clothes as a proxy of validation. So I think for me, and I think this is for other people too, the game...

Was you know I look at the lights in your studio right now You know like in this summertime like those lights that buzz the beat the you know Like I feel I always think about those little mosquitoes or things that go into the light. They can't help it I was wondering if they like know they're about to get zapped and die, but they just can't help it And that's how I feel about entrepreneurship. I think I was purebred. I think I was born into it I think

I think, and you know this, some of the people that we've been lucky enough to meet along the way of success that are very wealthy actually have kids that are fucking grinders and love building businesses. That wasn't a hunger thing. That wasn't a necessity thing. It's their DNA. So DNA is powerful. For me, it wasn't envy or need.

I see so many people motivated by they had it hard and they saw money as the way out and it was a chip on their shoulder. I don't have a chip on my shoulder. I have a curiosity in my stomach. I am so curious to how good am I at this skill? How do I play the game? I view it like chess, like boxing. I like the craft.

I think a lot of us have experiences as a kid that helped shape our future. We all do. I was bullied. I stuttered. Talk to us about Dover and some kid making a drink cup and then making you drink pee. I've never heard such a thing. I can't believe you brought this up. I know I've only brought that up in one or two interviews, which again, I'm giving heavy accolades to anybody involved in the research team for this interview or you yourself. Very impressive.

But what's even crazier about this is I literally thought about this either today or yesterday or the day before. In the last 72 hours, I thought about this. I don't even know why. I do know why because it probably meant that I knew this question was coming. That's a whole other story for another day. But it's really fascinating you just brought that up. I remember it very well. I was in Dover.

I cannot even recall what the kids look like, but I remember one was tall. I actually think I'm starting to remember. I think one of the kids name was Elliot. He was the alpha kid. There was four or five kids. I was fucking five, maybe six. And again, my mother grew up in the Soviet Union. In the Soviet Union, everyone's scared of the government. So there was no kidnapping. There was no crime. People were just scared.

What did that mean? It means kids were outside playing by themselves as early as four. By themselves. I remember my mom telling me to take care of my sister when we moved to Edison. We played outside. We moved in September, August of 82. My sister was born in July. My sister was three and played outside with me without my mom anywhere near her.

Like that's just how it was. So anyway, obviously if that's how it was, that's how it was for me. We moved to Dover. I'm five. I'm outside. Just fucking outside. You just literally, again, you may know this. You're just trying to find kids that are doing shit. I found these kids. They were not good kids. And, and yeah, I remember it vividly. Like I remember it's hazy, but it's vivid. You know, kid runs off to the side, peas in the Pepsi can. I'm, I'm very sharp.

I have common sense. I'm not very, like I'm very, I have a lot of common sense and I'm sharp. That's a core strength of mine. I have good instincts. I know when dangers is, like I come from like, not like the streets, but like I'm a Jersey kid. Like I'm not getting tricked. Like my wallet's not getting stolen. Like shit like that. So I knew something was, like I knew what, that's what I most remember about it. I knew that it wasn't Pepsi.

But they were able to force me to take a sip, you know, like, and it's not fun to drink another kid's pee, you know, and I really go home and tell your mom and yeah, I'm sure. But like, you know, like the truth is like, I don't, you know, I remember like not drinking it. Like, you know, putting the lips, you spit it out. I remember I, you know, it's so crazy. And this was foundational for me. Bullying has never penetrated me. Meaning even then it's funny where my brain's going.

It wasn't fun, right? It wasn't like I enjoyed it. But I don't think of it as like this iconic event. I think of it as a good story that paints a picture of like not everything is rosy.

But I can give you a lot of those events. Like when I think, I had twins move in, big guys, they were Andrew and Gregory, they were in fifth grade when I was in second grade in Edison. They were tough kids. They were the biggest kids in fifth grade. I was the smallest kid in second grade and we played football every day and did make pretend WWF wrestling. I was getting my ass kicked every day. And they were like bullying definitely by bully standards. I view them fondly as my friends.

I just think there was a lot of adversity. I'm sure. I mean, I cried all the time until I was 12. Yeah. I'm very emotional. Yeah. Like even you getting emotional is like starting to trigger me. Yeah. Like I'm like, I cry. I cried every day. I mean, almost, you know, my mom said, don't worry, you'll be more successful than all these kids one day. And it did. Yeah. I had a chip on my shoulder big time. Yeah. And I, you know, to me, I'm competitive. Like I want to win. Yeah.

And maybe the chip is so deep that it doesn't even look... For me, it's just so healthy. I'm just always so happy. I want to win, but I don't want you to lose. Does that make sense? Yeah. When I compete, I don't think I'm taking something from someone. I love capitalism in its most purest form because it's just who's better. And then let's all go home. It's not a winner-take-all. It's very abundant. Anyway, back to the Pepsi story. Yeah, but my mom...

Again, I mean you've parents in 2025 going to like yell at teachers for a see That wouldn't even registered on my mom's radar Yeah, if I came home and said mom these boys made you know, maybe drink pee should have been like okay or my dad Like this is what my dad would show up once in a while remember one time we're playing baseball when I was more like 11 and Edison and the guy in the corner like yelled at me my friends

And like, it was really not like nice. It was definitely like overly aggressive. And like, I told my mom, my mom like told my dad and my dad like rang the doorbell and said, don't do that to my son again. Like, it was like, oh my God, my dad like showed up out of nowhere to like be a hero. I like that. Like, but yeah, my parents didn't like, it was the fucking eighties. You didn't get involved in like too much shit. Now everything's so fucking sensitive. Back then it was just like, you know, like she would comfort me.

And then she would tell me to wipe it off. And it was easy for me to wipe it off. You mentioned you grew up with the gene.

Entrepreneurial Jane you had a lemonade stand the six years old you thought about franchising you did franchise you set this up on a street called Tingly Lane Yeah, I mean just so to make it clear for franchising was Spending the whole day convincing my other friends to stand behind the lemonade stand so I could like pick up the cash at the end of the day okay, and then You did a number of different things as well. You sold blow pops back in the day and

You sang Christmas carols as a Jew. Yes. So how does a Jew... That's Robbie Turding's favorite. This is the favorite one. Silent night. I got it all good. Go ahead and sing a verse. No, no, no. I'm done. That's all I got. And this one is the one that I find most interesting. You picked flowers in your neighbor's yard and then you went back and you sold them the same flowers. So...

How did you do that in particular? And are entrepreneurs who aren't born with the gene as successful as those who are born with the gene? No, they're not. I mean, they're just not. And I'll say, I'll jump to that part. I'll go back. Let me tell you why I believe that. I believe that anybody can get better at anything, but I do think talent is a real life thing. How can we not believe that?

Back to me not wanting to go more verses, I promise you, if I sounded like fucking Aretha Franklin, I would have finished that song. Back to us talking about football, I promise you, if I was fucking Aiden Hutchinson, I'd be in the NFL. That's my boy right there. The best. You know, so, you know, to me, this concept that entrepreneurship is not a skill is a ludicrous one, if anyone believes it, which I don't think most people believe.

are confused by that. And so I believe everybody in this circle, I'm looking at everybody in the room right now, right? I believe eight of us all got different things. And entrepreneurial talent is one of them. And by the way, somebody in this circle who's less successful entrepreneur than you and I might actually have it

I think having it also draws you to it back to the bug in the light. But let me play devil's advocate. But they didn't put in the hours against that talent. Like I, my brother loves golf now over the last 10 years. He's so frustrated that I won't take it up because he knows that the eight or 10 times I've played with him and he knows by the other sports we play with each other, I'm probably more naturally gifted at golf than he is.

I have a more natural swing. My hand-eye coordination is better than AJ's. He's got better skill sets in basketball and things of that nature. But in purest form, I think if he was sitting here, he would say, because he says it all the time, so I know he believes it, Gary has more natural skill in it. But I've only played 10 times. He's played 10 times in the last month. He's better at golf. I think that people that do not have a ton of entrepreneurial natural talent can be incredibly successful entrepreneurs because they put in the work.

But do I believe that if I was matched up with somebody who has less or more natural entrepreneurial talent, and we all put in the same amount of work, that there's a higher propensity that I would have that success? Yeah, I believe that. I think talent's part of the entrepreneurial equation. And then...

Selling flowers that you picked back to a name. That's you know, I love telling that story It's actually one story. It's it I only did it to one neighbor. She was the best I probably understood she liked me so much that she was willing to buy her own flowers for me. But yeah, I mean Painting rocks like when you have nothing you're trying to sell something Even lemonade was a little bit of a stretch for me early on because my mom wouldn't want to buy lemonade mix so, you know

Rocks, the biggest ones were washing car and shoveling snow. They were real gifts to me because they just required work. We had a hose, you know, and so, but the Flowers one,

Uh, John next door, they were very nice couple. Um, they were right next door to us and she had flowers and yeah, one day I ripped them, ripped some of them out of her yard and rang her doorbell and said, do you want to buy this? And she did. I wish I had the video of that because I can't remember all the details. I have a funny feeling. She had a funny smirk on her face and, and wanted to support me, which means a lot to me.

So at some point you got into baseball cards. We'll talk in a little detail about that. Talk to us about when you were at John Adams Middle School and the first card show you had on Oak Tree Lane at the Jewish Community Center. Yeah, the sixth grade baseball card collecting club was transformational. Up until that point, there was a kid by the name of Eric Conrad that used to come play.

Didn't know about divorced parents back then and I I didn't register me, but I was always like curious I'm like why does this guy only here in the summer, you know, because when I was in second grade I was young but he was the first one that introduced me to baseball cards He wasn't even actually a baseball card collector. He liked building card houses, you know, like taking playing cards and building We did though. Yeah, you did those so I would go over his house in the summer. We met him He stayed inside more than we did. He was like less active outside, but he would stay inside and

And he would make card houses. I thought that was cool. And so I'd come over once a week or once every two weeks and build a card house with him. I was into sports. I loved the Yankees at that point. And I mean, I remember like yesterday, we're in his basement. He brings out his cards, but this time there's baseball cards too to make the card houses.

I was like, what is this? And that was like game changing. So cool. And then I remember he said we could get them at Krauser's. Krauser's was like a 7-Eleven in New Jersey. I promise your friend knows what it is. It was also on Oak Tree Road. We walked or took our bikes to Krauser's and there they were, baseball cards. And I started buying them. And I just, that was fine. And then again, another great New Jersey Edison story. There was a flea market on US 1,

Route 1, the US 1 flea market. And me and my parents, my mom and my uncle and aunt went there to like pick up some groceries or something, just check it out. And there was a guy who had a baseball card booth, caught my attention and he had a price guide. And I begged my uncle Misha to buy it for me or my mom, one of them did. And now I came home and had a price guide. This is before Beckett, which is the big price guide. And it was CDM, I think, or something like that. Anyway, that was the first time I knew they were worth money.

And I ran up to my room and looked up every baseball card I had. And like some of them were worth like 30, and by the way, a card that I had being worth 35 cents was like striking fucking gold in Texas. I thought that was insane. And that started me getting really interested in fifth grade and then sixth grade came and the title wave came. There was a baseball card collecting club. This was now 1986 when the whole card thing really started happening the first time in America.

And that was the first big card boom. And I was in it. I was in it, affected by it. And then I did a card show at the JCC on Oak Tree Road. And...

I had the bug. I had the bug. And then the big one, the big first, that was like a half-assed card show. Like my friend really had the table. I kind of stopped by. My first card show was at really me driving. It was at the Phillipsburg mall. Once I moved in eighth grade, um, that was sixth grade where I tasted it. But by eighth grade, when I moved to Edison, excuse me, to Hunterdon County, um,

I did my own card show and crushed. I remember being petrified because the table's like 150 bucks or something like that. 280. Thank you. And, and it, it was a lot of money. It was, and my dad said, it'll be good experience. Everybody in the family thought I was going to lose. And we made, I mean, I had a great first day and made all my money back the first day. And,

I would argue from that moment on, I've never looked back. I would say Phillipsburg Mall, 1989, card show, when I made that money that weekend, when I was good, when I could tell that I was better than the grown men around me at selling cards, that was it. I've never really looked back. There's another show that you were prepping for at 6 a.m., and you're all ready to go, and your dad said you're not going. So what happened that day, and how did that moment change you? Oof.

That one's, boy, that hurt. By the way, that just hurt again. Yeah, I was super getting ready, bought a table. My dad's like, you're out. And I'm like, what do you mean? He goes, you have to work now. So I was getting really bad grades at that point in my life, like Ds and Fs, not even Cs. And my parents were pretty real about it. My mom grounded me all the time for progress reports and report cards. And my parents were like, look, if you're not going to be a scholar, you're going to be a worker. And so you have to start working in the store.

And I did. And, you know, I went from making thousands of dollars a weekend at baseball card stores to making two bucks an hour because that's what my dad got paid. I remember vividly that minimum wage was five oh five in New Jersey at this point. And I was getting two bucks an hour and it was devastating. I was I hated it at first. And I had a bag ice in my dad's basement.

You know a year later. I was stocking shelves and the first year was very challenging for me It was always a chore. I never wanted to do it. My mom was a ray of sunshine My dad was very quiet introverted very negative. So it was a new environment of adversity for me, too and

It really sucked until I realized that people collected wine and I was able to make that connection. And that transformed it. When I was 15, a year in, I realized that it changed kind of the way I would talk to my dad about it and really got it going.

When you were 14, your dad had a serious conversation with you. On the way there? He thought you were full of shit. And you had a very come-to... Jesus would be the wrong word because of the choice, but... Yeah, and you know what's funny? It was...

I speak of it as my dad really put me on the straight and narrow because I had salesmanship, gift of gab, like whatever it was to make a sale when I was 12. It was less that he thought I was full of shit. It was that he didn't like that I embellished the amount of cases we sold one day. So pretty early on,

About a year in, the first year was terrible. Basement the whole time, bagging ice, maybe making an occasional appearance upstairs just to pack something out. But the second year, I

I got to be upstairs and that really was good because then I was in the action. I was in the traffic. Customers would walk in. I was in the game. What I liked. That's why I liked flea markets. That's why I like baseball card stores. So pretty quickly, I would say within two or three weekends, my dad was, this is when my dad, I wish I haven't really talked to my mom and dad about this. I'm going to speak to them about this. My mom definitely gassed me up to my dad when I was coming in. She's like, he's got it. He didn't know. And he's skeptical. He's like, we'll see.

Very quickly once I was upstairs at 15, I think my dad realized he's got it. And so he started to really, that's when it got fun. He's like, "Hey, we got a lot of cases of this wine, sell it." I'm fucking 15, I look 11 and I'm slinging wine, effectively. And so it was really neat. And I just remember this one weekend, I don't remember if it was Iron Horse Chardonnay or Kenwood Chardonnay, some of the most prominent, Parducci, Petit Sorce. One of the things I remember early on in my career that he wanted to sell

And he's like, how'd we do, you know, on the way home? And I was like, crushed. I sold like 25 cases or whatever. And the real number was like 17. And the next day my dad came home because he didn't have the date in front of him. And he really made it to do with like, if you fucking sell 17 cases, you say 17, not 25. And that was kind of like the way he was addressing like

Word is bond, like straight. Like my dad's to this day, if you embellish to my dad, you've done a catastrophic lie. He's very rigid when it comes to lying, uh, embellishing. And so, um, I think that was very healthy for me because I had such natural gab at that point. And if I had a different, like I see it in people, I see people who have natural salesmanship grow up in a family full of hucksters and

And they end up selling hot, you know, you know this, what I'm about to say. Selling bullshit and selling real shit is the same shit. Some kids just go down the wrong path. And I don't think I was going to go down the wrong path. I wasn't going to be that. But I'm very grateful that he tweaked and tightened me because I think it's made me more respectful. You went to school and you were a D and F student. You weren't really...

Studying that hard, you made a point to be a wine expert at 16, reading Wine Spectator and science class. Every parent also thought you were going to be a loser. Yeah. And how did that feel and did that motivate you? Yeah, that motivated me. You know, back to chips on shoulders, again, and I, you know, it's fun to dissect it in this kind of environment.

I think there's healthy chips on shoulders and not healthy. You know, I always say there's two ways to build the biggest building in town. Just build the biggest building or spend your time tearing everyone's buildings down. I'm definitely, you know, you know, it's funny, even as I'm trying to go in this direction in the conversation, I don't think it's fully true. Meaning, I don't remember saying to myself that Steve Nash's mom, lovely lady, said,

Like I could see she was disappointed when she would ask me about how I was doing in school, but it didn't leave me saying like, I'm going to fucking show, you know what I mean? Like I never, nobody was atrocious to me. Teachers. I remember Mrs. Stats, my sophomore and junior and senior year math teacher really be disappointed in her reaction. And maybe a little razzy when I was a senior, but yeah, I mean,

You know this. Were you a good student? That was my ticket out. So I graduated top one percent of my class at Michigan. You know this.

We all knew that that we didn't even know that entrepreneurship was a ticket out when you and I were growing up It wasn't in the ether not for me at least what's for you near at Michigan? We'll talk about Jeff Wow and the related companies in a minute So you so maybe that you know again because you went to a strong University and you got exposed to more stuff I can tell you for me it was

We were all propagandized and brainwashed in junior high and high school that your college, where you go to college, is the unilateral, black and white, undisputed proxy and indicator to being successful. If you went to Harvard, you were going to be successful. And if you went to community college, you were a fucking loser. And that's how the world was that I was living in. And so...

It was a huge currency and I was adamantly debating it in my own head. I was completely convinced that I was going to be fiscally successful and emotionally successful. And I do believe that that's because of what my mom was saying internally at home and what was happening to me in the market. The merit of the market was speaking to me. I was making more money at card shows than grown men that were doing it full-time for their profession.

And that gave me huge confidence. So you end up going to Mount Ida College, which I'm sure everybody who's watched this podcast knows is his favorite college. And your freshman year, you were playing Madden's.

And then what happened? Pete from Maine said, you got to come and see this. And I go into a dorm room and there's a computer and I hear for the first time, cooch. I'm like, this is that internet thing. Informational superhighway. Worldwide web. You guys are going to be blown away by this. Literally, it was so crazy. We would sit there and watch people surf the web. Like, watch them.

Like I stood there for two fucking hours before I got to get on the keyboard watching Pete from Maine and others get on the computer and do different things. And even then what was super interesting was everyone was scared to leave AOL.

You just stayed in AOL. There was this browser, I remember, it would just be like the World Wide Web, and we're like, "We're not gonna click that. "That's too crazy. "You may get caught up." And yeah, I finally got on it late, 'cause it was like college life, right? If I recall, I didn't even get into that dorm room until like 10:00 p.m. I got finally on the computer at like 12:00, one o'clock in the morning, and I typed the two things that I knew, baseball cards and wine.

And I mean, out of a fucking movie. It was right there. Like literally, if I was ever lucky enough to have a movie made of me, the scene would be accurate. It was that dramatic. I literally remember seeing the reflection of my own face in the monitor saying, this is it. I just knew. And what I knew quickly after that was that Amazon and eBay were the game.

Pretty fast, you know, like pretty fast. Because it might have been second semester of freshman year, it might have been 95 already. Or maybe I'm blurring it and maybe it was a year later. Within the first year of my journey, I just knew that this was going to be it and I wanted to be as great at it as possible.

And I just studied it and would go to CompUSA, remember that retailer? And buy a magazine and read about it. So what I was doing with wine, I started doing with the internet. And I remember just really being fascinated by it. And the only obsession I had was, I'm going to take my dad's liquor store online. Because at that point, I was already committed that I was going to go to the family business. And I was very focused on

And this only deeply immigrant kids, I think, will understand me right now. This is hard, I think, for an American kid to understand. Based on American culture, it's not good or bad. But I was obsessed. That would be the word I would use. I think there's a lot of American kids who are excited to help their family business as long as it helps them. I think immigrant kids will understand this. I was obsessed with building up the family business for my parents.

And even today, even as I say that, I'm almost like, was I brainwashed? Am I that noble? Did my parents do such a good job and I had such a good understanding that I would still get mine later? I don't know, but I think it was very unusual. I remember people thinking it was unusual.

I don't know if I was addicted to the nobleness of it, but at that point in my life, before I saw the internet, like junior year of high school, two years earlier, three years earlier, I was like, I'm going to go and fucking crush for my parents because I can. And so all I was obsessed with is this is how I'm going to crush. Because originally I thought I was going to open 100 stores. I always thought I was going to build the Toys R Us of wine library, of wine.

My framework was CompUSA and Staples and McDonald's and Toys R Us and Walmart. There was no Amazon and eBay to look to. But that was the night I decided I was going to build it through that. And I did that. You're listening to part one of my incredible interview with Gary Vee. Be sure to tune in next week to part two of my incredible conversation with Gary. Thank you.