In short
Gary Vaynerchuk (Gary Vee) recounts his immigrant upbringing from the USSR to New York, how his parents’ support shaped his mindset, and how early hustles (lemonade, baseball cards, selling wine) led to his obsession with entrepreneurship and later digital commerce (eBay/Amazon). He argues that adversity, optimism, and “I believe in you” fuel success more than money does, and that entrepreneurial talent plus relentless practice drives outcomes.
Guests
Gary Vaynerchuk (Gary Vee), CEO of VaynerMedia; serial entrepreneur, angel investor, venture capitalist, public speaker, six-time NYT bestselling author; co-founder of Gallery Media Group, Sasha Group, VaynerSpeakers, VaynerCommerce, VaynerSports.
Key claims
“Self-made” is contextual and depends on others’ help; money isn’t the main motivator—comfort reduces hunger; entrepreneurship is partly DNA but can be built with work; bullying didn’t “penetrate” him—he reframed adversity.
Notable examples
Refugee arrival in Queens; mother knitting a Jets jersey; being forced to work in the family liquor store at low wages; baseball card shows at Phillipsburg Mall; learning wine by reading Wine Spectator; first internet night at college using AOL, then searching “baseball cards and wine,” predicting Amazon/eBay.
Written by AI. May contain mistakes. Listen to the episode to check what was said.
Chapters
Tap a time to open that second in VOEarly Internet Memories
0:00 to 0:39
Gary shares his early experiences with the internet and AOL.
“You guys are gonna be blown away by this.”
Gary's Family Background
1:41 to 2:09
Gary discusses his father's immigration from the USSR to the US.
“Let's start at the beginning, and I want to start with your dad.”
Influential Figures in Gary's Life
2:09 to 5:54
Gary talks about Jack, Arlene, and Bob and their impact on his father's journey.
“I right off the bat adore you because, you know, I've been very fortunate over the last decade.”
The Role of His Mother
5:54 to 6:52
Gary reflects on the influence his mother had on his life and success.
“Because it's unbelievably true, but it's also very contextual.”
A Memorable Childhood Gift
6:52 to 14:01
Gary shares an emotional story about a homemade Jets jersey his mother made.
“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.”
Childhood Memories and Mom's Love
14:01 to 15:04
Gary shares nostalgic stories from his childhood, focusing on his mother's sacrifices and the significance of a handmade jersey.
“Saving money was the currency back then, as you know, probably as a child.”
Money and Motivation: A Complex Relationship
15:04 to 15:39
A deep dive into how financial background shapes work ethic and motivation among youth.
“Did not having money motivate you to be successful?”
Growing Up in Adversity
16:28 to 20:26
Gary reflects on his upbringing in tough environments and how it shaped his entrepreneurial spirit.
“All right, now let's get back to the video.”
The Impact of Bullying
20:26 to 25:38
Gary recounts experiences with bullying in childhood and how they influenced his perspective on competition and success.
“I am so curious to how good am I at this skill?”
The Entrepreneurial Gene
25:38 to 28:00
A discussion on innate entrepreneurial traits versus learned skills, illustrated with personal anecdotes.
“But like my mom, again, I mean, you have parents in 2025 going to like yell at teachers for a C.”
Show all 17 chapters
Entrepreneurial Talent vs. Hard Work
28:00 to 29:40
Explore the debate on the importance of natural talent in entrepreneurship compared to hard work.
“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.”
Childhood Ventures: From Flowers to Rocks
29:40 to 31:10
Gary shares his early entrepreneurial experiences selling flowers and other ventures as a child.
“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?”
The Baseball Card Boom
31:10 to 34:00
Learn about Gary's fascination with baseball cards and the transformative impact of his collecting experiences.
“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.”
Challenges of Early Work Experience
34:00 to 36:30
Gary discusses the challenges he faced in his early work experiences and the lessons learned from them.
“It was, and my dad said, it'll be a good experience.”
Father's Influence and Salesmanship
36:30 to 40:00
Delve into Gary's relationship with his father and the impact of his father's expectations on his sales skills.
“And it really sucked until I realized that people collected wine and I was able to make that connection.”
Academic Struggles and Entrepreneurial Aspirations
40:00 to 42:00
Gary reflects on his academic struggles and how they motivated his entrepreneurial ambitions.
“Every parent also thought you were going to be a loser.”
Gary's Journey from Community College to Internet Pioneer
42:00 to 46:50
Learn about Gary's early experiences and his obsession with building a family business through the internet.
“If you went to Harvard, you were going to be successful.”
Transcript
Automatic transcript. May contain errors.0:00You 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 like, that's too crazy. I got finally on the computer at like 12, one o 'clock in the morning.
0:29You 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.
0:45Welcome 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 the most as Gary V. Gary is a serial entrepreneur, angel investor, venture capitalist, public speaker, six-time New York Times bestselling author, and one of the world's leading experts on the topics of marketing and social media.
1:21He 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 is 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 Babarisk, USSR. He moved to the United States when you were three years old.
1:55Didn'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 his future. I right off the bat adore you because, you know, 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 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.
2:43Jack 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. 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-focused on Walter Cronkite, big thing.
3:27And 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 Highest 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.
4:01When 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. It would have been very easy for them to look the other way of their 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.
4:48And 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 old, 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.
5:27All in five years. Which is remarkable if you think about it. And so, I mean, I think, you know, 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, you know, I think we all as human beings, you know, self-made is a very funny thing. Because it's unbelievably true, but it's also very contextual. It's like Lucky.
6:05Lucky 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 Gennadzi. 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.
6:52So 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 Dan 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.
7:32please 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 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 um she is the strongest person i know um she's just incredibly strong and she made me very strong and you know obviously just even already hearing how this interview is going to go i'm sure you've seen how much i speak about her and how I revere her.
8:24And 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,
9:08you know, when I talk about any time I'm brought up, even that intro, when I hear six-time this or great this or the accolades run right through me and I'd point 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? 100%. They said those words out loud? My mother, who was much more of a communicator in my life,
9:39not only did she say that, it was a constant currency in my life. like 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 or for a relative or for my sister, it was always reinforced with you're a golden heart, you're special, you're a star. There was never a day where I didn't feel I was capable.
10:31And 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.
11:18Where did you grow up? You're sure right. 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 p.m. when we were growing up that would air on network television that would say, it's 10 p.m. Do you know where your kids are? Because our parents literally didn't know. We were outside all the time.
11:50You might forget to know if they even came home for dinner. So I was raised by Edison, New 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 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.
12:33And another kid, I don't remember his name, he had an 85 and that was Wesley Walker. And so now we're playing football all the time. And 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 could probably get one at Kmart for 10 bucks or Bradley's. But we just did not. The only clothes we had as kids was the liquor T-shirts my dad would get as promotions from the store. Like literally, I did not buy a T-shirt until I was in college because every T-shirt we had was a liquor promo T-shirt.
13:16There were eight of you in the studio apartment. Yes. My core family was two. Those cousins, my grandma, they lived elsewhere. We eventually moved at us. it was just me and my mom, my brother, 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, 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 going to be born in January of 87. I'm laughing right now because I know my sister's about to hear this line and she's just laughing 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 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.
14:24Saving 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 when I take photos now I put up the number five is it's just a little head nod to my mom, who is my hero.
15:04Did not having money motivate you to be successful? And what's your advice to kids who grew 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.
15:37I hope you're enjoying this video so far. But before we jump back in, I want to know if you've ever thought about what you need to do to reach another level of success in your life. Over the last 25 years, I've been an advisor to more than 50 companies. I've invested nearly 100, including Google Lyft and Seagate. And I also co-founded a company that today is worth more than$15 billion. I've been incredibly blessed in my journey. And at this stage of my life, I want to give back. I want to share the lessons I've learned so you can reach incredible success way faster than I did. In my own journey, I've learned that having the right mentor is a massive advantage to achieving our goals.
16:09I'm hugely passionate about mentoring others. I'm looking for a few hungry entrepreneurs who are excited to take action on their journey to incredible future success. So if that's you, I've got an opportunity. In the description of this video, there's a link where you can apply to work with me. All you need to do is answer a few simple questions. And if you're a good fit, my team will reach out so we can build a game plan together. All right, now let's get back to the video.
16:33it'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 right 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.
17:17Peace of mind and lack of anxiety 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 Russia or the Soviet Union and then Queens in like the housing projects and then Dover and then Edison. I didn't even, 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.
18:20I definitely did not know. I actually thought we were good, like real good. My dad really grinded. And so, I don't know, we were in the mix. There was kids that I went to school with that literally didn't have lunch money, that wore the same clothes, that smelled. 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, 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 like what a Mercedes was when I was 11, it never crossed my mind that I wanted one.
19:05I 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. I was, you know, I look at the lights in your studio right now, you know, like in the summertime, like those lights that buzz 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.
19:48I was wondering if they like, no, 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 there was a chip on their shoulder.
20:30I 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'm viewed 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 you drink pee. Making you drink pee. But 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.
21:14Very 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 uh 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.
21:57So 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. 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 uh 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 a wrap like i i come from like street not like the streets but like i'm a i'm a 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 was that's 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 keith'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.
23:43I remember, 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, and 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.
24:31I 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. I had a chip on my shoulder big time. Yeah. And, you know, to me, I'm competitive. like i want to win 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 like i i want to win but i don't want you to lose does that make sense yeah like i don't 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 like let's all go home.
25:38It's not a winner take all. It's very abundant. Anyway, back to the Pepsi story. Yeah. But like my mom, again, I mean, you have parents in 2025 going to like yell at teachers for a C. That wouldn't even register it on my mom's radar. Yeah. If I came home and said, mom, these boys made, you know, made me drink pee. She'd have been like, okay. Or my dad, like, this is when my dad would show up once in a while. I remember one time we're playing baseball when I was more like 11 in Edison and the guy in the corner like yelled at me and 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.
26:20Like I 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 80s. 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 gene you had a lemonade stand at six years old you thought about franchising you did franchise you set this up on a street yeah i mean just so to make it clear for everybody But franchising was spending the whole day convincing my other friends to stand behind the lemonade stand so I could pick up the cash at the end of the day.
27:08Okay. And then you did a number of different things as well. You sold blow pops back in the day. You sang Christmas carols as a Jew. Yes. So how does a Jew... That's Robbie Turning'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 pick flowers in your neighbor's yard and then you went back and you sold them the same flower. 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?
27:49No, they're not. I mean, they're just not. And I'll jump to that part and 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 are confused by that.
28:33And 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. 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.
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29:18I 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?
30:00Yeah, I believe that. I think talent's part of the entrepreneurial equation. And then selling flowers that you pick back to a name. I love telling that story. It's actually one story. 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.
30:36they were real gifts to me because they just required work we had a hose you know and so but the flowers won 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 wanted to support me, which means a lot to me. So at some point, you got into baseball cards. We'll talk a little detail about that.
31:14Talk 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. I didn't know about divorced parents back then. And I didn't even register me, but I was always like curious. I'm like, why is 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.
31:48He liked building card houses, you know, like taking playing cards and building. Yeah, we did those. 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 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.
32:19I was like, what is this? That was like game-changing. So cool. And then I remember he said we could get them at Crousers. Crousers 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 Crousers 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, my parent, my mom and my uncle and aunt went there to like pick up some groceries or something, just check it out.
32:57And 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 was 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.
33:33And that started me getting really interested in fifth grade and then sixth grade came and the tidal 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, that was sixth grade where I tasted it, but by eighth grade when I moved to Edison, excuse me, to Hunterdon County, I did my own card show and crushed, I remember being petrified because the table's like 150 bucks or something like that.
34:28$280. Thank you. And it was a lot of money. It was, and my dad said, it'll be a 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 that's 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.
35:13So what happened that day and how did that moment change? That one's, boy, that hurt. By the way, that just hurt again. Yeah, I was super getting ready. Bought a table. And my dad's like, you're out. And I'm like, what do you mean? And he goes, you have to work now. So I was getting really bad grades at that point in my life. Like D's and F's. Not even C's. 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.
35:49And 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 505 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.
36:32And 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 it was Jewish. Yeah. And you know what's funny? It was, I speak of it as my dad really put me on the straight and arrow because I had salesmanship, gift of gab, like whatever it was to make a sale when I was 12.
37:13It was less than 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 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 hadn't really talked to my mom and dad about this.
37:55I'm gonna 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 Sarras.
38:29One 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, embellishing, and so 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.
39:22I see people who have natural salesmanship grow up in a family full of hucksters and they end up selling, 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 gonna go down the wrong path. I wasn't gonna be that But I'm very grateful that he tweaked and tightened me because I think it's made me more respectful. You mentioned school and you were a DNF 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.
40:05Yeah. 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 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 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, like I could see she was disappointed when she would ask me about how I was doing in school.
40:53But 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. Statz, like sophomore 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.
41:36For you here at Michigan. We'll talk about Jeff Powell and the related companies in a minute. So maybe that, again, because you went to a strong university and you got exposed to more stuff. I can tell you for me, 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.
42:22And 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 watching this podcast knows, this is his favorite college. And your freshman year, you were playing Maddens.
43:03And then what happened? Pete from Maine said, you've 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, I'm like, this is that internet thing. Informational superhighway, worldwide web. You guys are gonna 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.
43:46You 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 like, that's too crazy. You may get caught up. And yeah, I finally got on it late because it was like, you know, college life, right? If I recall, like, I didn't even get into that dorm room until like 10 p.m. I got finally on the computer at like 12, one o 'clock in the morning. And I typed in, you know, I typed the two things that I knew, baseball cards and wine. And I mean, out of a fucking movie. It was right that, like literally, if I was ever lucky enough to have a movie made of me, the scene would be accurate.
44:23It 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 um just really being fascinated by it and the only obsession i had was i'm gonna take my dad's liquor store online because at that point i was already committed that i was gonna go to the family business and i was very focused 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.
45:34That 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 like 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 gonna go and fucking crush for my parents because I can.
46:24and so all I was obsessed with is this is how I'm going to crush right because originally I thought I was going to open a hundred stores I always thought I was going to build the Toys R Us of wine library of wine my framework was comp you know comp USA 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.
From the publisher
Gary Vaynerchuk, commonly known as Gary Vee, is an influential entrepreneur, speaker, and internet personality, best known for his expertise in digital marketing and social media. Starting his career in his family's wine business, Gary's innovative approach to e-commerce and content creation catapulted the business from a local enterprise to a national leader in wine retail. He later founded VaynerMedia, a leading digital agency that services Fortune 500 clients across the globe.
In this episode, Gary shares his unfiltered insights on the dynamics of building and scaling businesses, the evolution of consumer engagement, and the relentless pursuit of hustle.
Timestamps:
02:41 - Introduction.
05:21 - Gary Vee narrates the immigration challenges faced by his family leaving the Soviet Union and adjusting to life in America.
08:02 - Gary Vee talks about his father's entrepreneurial journey from managing a store to owning it and the lessons learned from observing his work ethic.
10:41 - Randall Kaplan praises the inherent strength and resilience of influential women in challenging environments.
13:20 - Randall Kaplan shares an emotional personal story, underscoring the importance of strong family values.
16:04 - Gary Vee elaborates on the supportive dynamics within his extended family and the emotional bonds that shaped his upbringing.
18:41 - Gary Vee emphasizes the crucial life skill of dealing with adversity and finding comfort in uncomfortable situations.
21:20 - Gary Vee reminisces about his childhood summers, filled with familial connections and simple joys.
24:03 - Randall Kaplan reflects on his childhood outdoor activities, noting the less supervised yet richly interactive play of his youth.
26:40 - Randall Kaplan discusses overcoming personal challenges and the motivation behind his drive to succeed despite obstacles.
29:23 - Gary Vee debates the nature of entrepreneurial success, questioning if innate talent is a necessary component and sharing his personal experiences with early business ventures.
32:03 - Gary Vee discusses his youthful business initiatives, including running a lemonade stand and the creative ways he expanded it.
34:44 - Gary Vee recalls his childhood efforts to earn money through various small ventures, from selling flowers picked from neighbors’ gardens to singing carols.
37:22 - Gary Vee shares his philosophy on the value of hard work over formal education, reflecting on his personal and family experiences.
40:00 - Gary Vee looks back on a defining weekend in his youth that solidified his passion for business and innovation.
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