Can Anyone Be an Entrepreneur? | A Conversation w/ Randall Kaplan - The GaryVee Audio Experience: Summary & Transcript

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Podcast Summary: The GaryVee Audio Experience - Can Anyone Be an Entrepreneur? | A Conversation w/ Randall Kaplan

Overview In this episode of The GaryVee Audio Experience, Gary Vaynerchuk engages with entrepreneur Randall Kaplan in a deep discussion about the nature of entrepreneurship. The central question explored is whether entrepreneurs are born with inherent traits or if these qualities can be cultivated over time.

Key Themes and Discussions

Nature vs. Nurture in Entrepreneurship
Born vs. Made: Kaplan shares his belief that while anyone can improve their skills, innate talent plays a significant role in entrepreneurial success.
Childhood Ventures: They discuss personal stories, such as Kaplan's early entrepreneurial efforts like selling flowers from neighbors' gardens and running a lemonade stand.
Talent vs. Hard Work: Kaplan argues that while natural talent may give some an edge, hard work can lead to success for those without innate entrepreneurial skills.

The Role of Environment and Motivation
Impact of Upbringing: Kaplan reflects on how growing up with limited resources can drive entrepreneurial ambition, while those from affluent backgrounds may lack motivation.
Adversity as a Teacher: Both Kaplan and Vaynerchuk agree that learning to deal with adversity is crucial for success in business and life.
Curiosity Over Envy: Vaynerchuk emphasizes his curiosity and desire to learn, rather than feeling envious of others' successes.

Customer Service and Business Culture
Customer Service Story: Vaynerchuk recalls a pivotal moment when he personally delivered a case of wine during a snowstorm to emphasize the importance of exceptional customer service.
Building Company Culture: He underscores that actions taken during critical moments can define a company’s culture and values.

Personal Stories and Life Lessons
Family Influence: Vaynerchuk discusses the profound impact of his immigrant parents on his work ethic and values, highlighting the sacrifices and support they provided.
Childhood Experiences: He shares anecdotes from his upbringing, including experiences of bullying and his mother's efforts to instill confidence in him.

The Importance of Work Ethic
Controllable Success: Vaynerchuk posits that work ethic is the most controllable aspect of success, arguing that the hustle is crucial, albeit balanced with self-care.
Philosophy of Persistence: Both speakers emphasize the value of tenacity in overcoming challenges and achieving goals.

Views on Financial Success
Money and Happiness: Vaynerchuk warns against the pursuit of money as a primary motivator, stating that financial wealth does not guarantee happiness.
Long-term Goals: He shares his aspiration to own the New York Jets, illustrating the importance of having ambitious, personal goals.

Key Takeaways

Entrepreneurship is a Blend: While natural talent plays a role, entrepreneurship can also be developed through experience, hard work, and resilience.
Customer Experience Matters: Actions taken to ensure customer satisfaction can have lasting impacts on business and culture.
Work Ethic and Persistence: A strong work ethic and tenacity are vital components for overcoming life's hurdles.
Health over Wealth: True fulfillment comes from passion and purpose, rather than purely financial gain.

Conclusion This episode provides insightful reflections on the qualities that contribute to entrepreneurial success. It blends personal anecdotes with broader life lessons, encouraging listeners to forge their paths through curiosity, hard work, and resilience. Whether viewed as a calling or a craft, entrepreneurship is painted as an attainable goal for those willing to put in the effort.

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Transcript

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0:00You know, I look at the lights in your studio right now. You know how like in the summertime, like those lights that buzz, I always think about those little mosquitoes or things that go into the light. They can't help it. I always wonder if they like know they're about to get zapped and die. And that's how I feel about entrepreneurship. I think I was purebred. I think I was born into it. 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.

0:29You 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 called tingly tingly lane was your street yeah i mean just so to make it clear for everybody 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 you sang christmas carols as a jew yes so how does a do and and this is this is the favorite one. Silent night. I got it all good. Go ahead and sing a verse. No, no, I'm done. That's all I got.

1:02And 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? No, they're not. I mean, they're just not. And I'll say, I'll jump to that part. I'll 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 fuckin' Aretha Franklin, I would've finished that song.

1:45You 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. 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.

2:26Like 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. Right? 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.

2:59He'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 pick back to a neighbor? That's, you know, I love telling that story.

3:34It'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. They were real gifts to me because they just required work. We had a hose. You know, and so, but the flowers one, John, next door, they were a very nice couple.

4:15They were right next door to us and she had flowers and yeah, one day I ripped them, and ripped some of them out of her yard and rang her doorbell and said, do you wanna 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 let's talk about, 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.

4:56And 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, 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.

5:34I 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 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. I, one of the things that's interesting about growing up in like Russia and then, or the Soviet Union, and then Queens and like the housing projects and then Dover and then Edison, I didn't even, I didn't even know what money was.

6:32Meaning 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. 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.

7:15Like, 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. I still have never had a real high-end car. What do you drive now? Nothing. I have a driver so that's even like more ridiculous than a high-end car but like when I bought when I had money you know I got a Jeep Grand Cherokee and like to me that was I never thought of a car or a watch or clothes as a proxy of validation.

8:04For 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. You need to have great customer service to build any business. So talk to us about this crazy story about this woman who wanted a case of Behringer White Zinfandel in the two and a half hour snow. This was, this is such a, so anybody who owns a business, if you're listening right now and you want to make a point, a culture, do something in action.

8:58Don't make a fucking poster and put it in the hallway. don't tell a story that happened in the past you and I have enough more stories where we can tell the kids do an action so I was building this store we're now on fire at this point this is later this is like 2002 or 2003 we built a new store I grew up in a smaller store then we built a big store as I was growing the revenue I am the man on the floor and this is the holidays when I tell you from 18 to 34 years old, my December, and I mean all the first 24 days of December, outside of when I was in college, but even then I came home way early because I was barely going to class.

9:46I would spend from 7 a.m. to 10 p.m. on the floor of my dad's liquor store. That was prime time, especially pre-internet, you know? we are in the midst of one of the busiest days in the history of the store and now we're doing internet business and we get a phone call in the order department I'm running upstairs downstairs I'm keeping an eye on the internet and the store and I'm fucking a maniac and we get this call from the son of this elderly woman wasn't even her that her case got misshipped and this was like December 23rd or second or first. I don't remember, but put it this way. She lived in Jersey and that's one day delivery and I knew that if we put it back in the mail, she wouldn't have gotten it for Christmas.

10:33And he made a big to-do that she needed it for Christmas. I remember this day like yesterday. I knew that there would be a day that I wasn't gonna be at that store. I knew that I was gonna have to build my own life at some point because I knew my dad viewed it like an immigrant, which is, oh, this is your business, but it's really not. Like, I can't, buy a home because I have no equity. Like I couldn't, you know, like I would inherit it when he would pass, well I'm fucking gonna be 50 in 15 months and my dad's still working every day. So you can imagine I was smart enough, thank God, at 22 to be like I gotta do my own thing.

11:06But I remember I needed to do things because once I was gone I wanted them to know how it was built. I knew then.

11:19So even though I'm on the floor and generating 10 to$20 ,000 an hour, just me personally, on someone like you that had high net worth that would come in and be like, I need three cases of high-end wine for the holidays. I was that guy. I decide to make a huge to-do about this case of Behringer White's Infidel. It's snowing. Like the weather's bad. And I decide to grab a case from the basement and I tell my inner team, just like this, in a circle, I'm like, I'm gonna go deliver this because we have the best customer service in the game. And they are stunned. I never, I don't go to pee for 15 hours during the day.

11:58That's how busy it is and how committed I am. And now I'm going to drive to Bergen County. Isn't that an hour? And that's without snow. The fuck are you doing, Gary? And I said, this is, I just remembered that this was my moment to make a point. So I did it. I drove. I enjoyed it. I listened to sports radio on the way. Got back. Everybody was stunned. Everybody was sweating. Brandon was like you missed Mr. Thompson and Mr. Smith and like all this money was lost but it became a story. To this day that story is being told to employees in our store about customer service. I might have lost$20 ,000 in sales that hour but I've helped my dad make millions since and I think more companies should understand that actions carry enormous weight and I believe that every leader that's listening right now should think about what they care about most and instilling in their company and then should go out of their way for the most hyperbolized executions of those things so that it becomes lore.

13:01I mean, look at this. I literally did that action and here I am 20 plus years later having the luxury to tell that story on an important platform like this. Think about that. This is the meta of the thesis. It's how you build it. It's how you fucking build. How do you think everything's built? Everything's based on stories. Why do you think religion exists? 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 Babrish, 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?

13:48I 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 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 in the family in a lot of ways.

14:40He 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 focused on Walter Cronkite, big thing. And there's 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.

15:18The 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 gonna 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.

15:55In the 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. 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 old, that now Bob was really running.

16:39He was the older son, and 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 um and so yeah 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.

17:44It'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 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.

18:27And 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. Very. 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.

19:12Please 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. 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 going to go, I'm sure you've seen how much I speak about her and how I revere her.

20:05And 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,

20:47you 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 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

21:19not 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 5 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 your golden heart, you're special, you're a star. There was never a day where I didn't feel I was capable.

22:11and 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's was an incredible place to grow up in the 80s and um you know, how old are you? 55. So this is perfect. 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?

22:58Detroit. 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. Like we were outside all the time and like you might forget to know if they even came home for dinner.

23:33So 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.

24:13And 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 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, I did not buy a t-shirt until I was in college because every t-shirt we had was a liquor promo t-shirt.

24:55There 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, it 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 wish 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 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.

26:03Saving 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.

26:44I 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 peeing in a Pepsi cup and then making you drink pee. I've never heard of 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.

27:18I 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 looked 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.

27:54There was no crime. People were just scared. What did that mean? 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.

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28:34I found these kids. They were not good kids. 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 very sharp. I have common sense. I'm not very, like I'm very, I have a lot of common sense that I'm sharp. That's his core strength of mine. I have good instincts. I know when dangers is a wrap. Like, I come from, like, street, 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 was, that's what I most remember about it.

29:15I 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. Did you go home and tell your mom? Yeah, I'm sure. But the truth is, I remember not drinking it. You put it in the lips, you spit it out. I 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.

30:10Like 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.

30:47Yeah. Like I'm like, I cry. I cried every day. I mean, almost. 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 want to win, but I don't want you to lose. Does that make sense? Like 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.

31:32It'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 on my mom's radar if I came home and said mom these boys made me drink pee she'd have been like okay or my dad this is when my dad would show up once in a while I remember one time we were playing baseball when I was more like 11 in Edison and the guy in the corner yelled at me and my friends and it was really not nice it was definitely overly aggressive and I told my mom and my mom told my dad and my dad rang the doorbell and said don't do that to my son again And I was like, oh, my God, my dad showed up out of nowhere to be a hero.

32:19I like that. But, yeah, my parents didn't. It was the fucking 80s. You didn't get involved in too much shit. Now everything's so fucking sensitive. Back then it was just 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. 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 Oaktree 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.

33:05I didn't know about divorced parents back then, and I didn't even register me, but I was always curious. I'm like, why is this guy only here in the summer? you know like because 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 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.

33:42I loved the Yankees at that point. And I mean, I remember it 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. And I was like, what is this? And I 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 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.

34:44And 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.

35:24I 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. 280. Thank you.

36:02And 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 at selling cards. That was it. I've never really looked back. There's another show at Fullsville Mall that you were prepping for at 6 a.m. and you're all ready to go and your dad said you're not going.

36:46So what happened that day and how did that moment change your life? 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.

37:23And 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$5.05 in New Jersey at this point. And I was getting two bucks an hour and it was devastating. I hated it at first. And I had a bag of 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.

38:26On the way there? He thought you were full of shit and you had a very come to, Jesus would be the wrong word because we're Jewish, but. 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. 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 when I 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.

39:28I'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.

40:03One of the things I remember early on in my career that he wanted to sell. And he's like, how'd we do 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 of 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.

40:47And 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. I see people who have natural salesmanship, grow up in a family full of hucksters, and they end up selling huck, 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 D and F student.

41:26You weren't really studying that hard. You made a point to be a wine expert at 16, reading Wine Spectator in science class. Every parent also thought you were going to be a loser. 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, 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 gonna fucking show, you know what I mean?

42:31Like I never, nobody was atrocious to me. Teachers, I remember Mrs. Statz, my sophomore and senior year math teacher, really be disappointed did 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. Freshman year at Michigan. We'll talk about Jeff Blau and the related companies in a minute.

43:14So 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 gonna 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.

44:08And 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 is his favorite college. And your freshman year, you were playing Madden. And 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, cuckoo, I'm like, this is that internet thing.

44:50Informational super highway. World Wide 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. You just stayed in AOL. Like there was this browser, I remember it would just be like the worldwide web, and we're like, we're not gonna click that. That's like, that's too crazy.

45:27You may get caught up. And yeah, I finally got on it late because it was like, you know, college life, right? If I recall, I didn't even get into that dorm room until like 10 p.m. I got finally on the computer at like 12, 1 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 then, 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.

46:05I 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'd started doing with the internet. And I remember just really being fascinated by it.

46:47And the only obsession I had was, I'm going to take my dad's liquor store online. Because at that point, I was already pot committed that I was going to go to the family business. And I was very focused. And there's 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.

47:18I 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.

47:58And so all I was obsessed with is this is how I'm gonna crush for my, because originally I thought I was gonna open 100 stores. I always thought I was gonna 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 gonna build it through that. And I did that. You took a company from three million to$60 million in a short amount of time. You saw things that people didn't see at the time. You bought keywords, AdWords, wine was five cents.

48:33and then after nine months went to 10 cents. So what did you see that nobody else saw as really a first mover advantage with I think is so important sometimes in building businesses? It's what I see right now with live shopping on social. I'm going to assume that, I'm going to just look around the room, that people here know that TikTok shop exists, that people sell things on TikTok. I'm going to assume that people here know that, or this might be small, but you might know what whatnot is, live shopping. I'm going to assume that people in this circle know that China's been selling stuff on live social for the last seven years at scale.

49:08I'm gonna assume that people are listening and watching, might have saw the viral video of that woman with the handbags who does$8 million just by doing this. I know that all to be true. I also know that almost every single person in this circle right now is underestimating it. I know that 99.9 % of the people who are watching this right now don't understand it the way I do. I understand it for what it is, which is it's going to be massive, massive. that if you ask me right now, out of all the optionality in the world of how to make money in the next five years in America, that live shopping is at the tippy top of my list.

49:45That's what I saw with websites, email, and Google AdWords. I don't think I was the only person that saw it. I just think what I'm very good at is I view these trends like poker. And I view live shopping on whatnot and Fanatics Live and TikTok Shop and Meta will have to do it because it's gonna get too big. I view it like having the nuts in poker. I feel like I've got the best, like I know it's the best hand. And so if you know you have the best hand, educate me, you're poker players, you go all in. Cause you've won. Sure, they may fold, but you go all in. I know that. That's what I do for a living.

50:23What I'm good at is knowing what humans are gonna do. And I know when it's the biggest hand, the best hand. And so the reason I was able to build my daddy's liquor store was having a website was better than having a catalog. Right? I wanted to compete with Sherry Lehman's, Zachy's, Morel's, Sam's Wine Club in Chicago, K &L in California. I wanted to have the specs in Texas. I wanted to have the best wine store in the country. What were those stores doing when I was in high school and college? they were buying full page ads in the Wall Street Journal and the New York Times Wednesday dining in section and they were sending catalogs in the mail.

51:05I outflanked them by having a website and having an email newsletter. So my email newsletter in 1998 when 94 Dominus came out and Insignia, I would email everybody and they would buy from me. They would get the catalog from Sherry Lehman's four weeks later because catalogs are slow. Email is fast. catalogs are expensive to make and ship email was free so even though I had no money I outsmarted them by knowing where the attention was because Wall Street had moved to email but not everybody caught up I believe social media is now in my brain 20 % of all social media content is live shopping it's not yet but it will be and so I'm going to move fast during this era on it that's what I did with email with having a website at all and then finally the big final atomic bomb outflanking everybody on Google AdWords.

52:03Let's move to December 2008 and you have a meeting at ESPN. Your brother AJ's graduating BU and you walk out of there with a couple of things. What did you walk out with and then what happened next? Well, I first walked out with$5 ,000 and I couldn't comprehend how I, you got to remember at this point I'm still making less than$100 ,000 a year even though I'm 33 years old and built this huge business. immigrant life again if you don't live in an immigrant business you don't understand but like i built this huge business created hundreds of millions of dollars in revenue over that course a period of time and i'm still making very little my dad's making super little too but he owns the business so i'm starting to think about my next chapter my brother's about to graduate and we're bouncing a lot of ideas daily fantasy sports which probably would have done well something that looked like groupon and living social that probably would have done well something that looked like BuzzFeed that probably would have done well but those would have all taken time to build and I really didn't have any money and AJ surely didn't and because I just invested in Facebook and Twitter so all my liquid was gone and so consulting, getting paid for action was a better cash flow option and it's amazing and I get this random email because at this point I'd invest a lot of followers on Twitter but it's still early It's the first couple years of Twitter.

53:25And ESPN asks if I could come in and consult on how to grow their social, their Twitter specifically. What year was this? This is 2008. Steve Bornstein was CEO or he had left? It wasn't at that level. It was way lower down. It was three to four levels below that, maybe five, if I'm thinking properly of their org at the time. It was marketing, but it wasn't even like, it was definitely not the CMO. let alone the CEO and I don't even think it was the number two in marketing it was a lower level but the guy had the ability to write a$5 ,000 check which is nothing for a corporation so it was lower level anyway I go in I sit in a room like this I consult for a couple hours I enjoy it to no end and I leave and literally it's like old school like you got a check back then and I call my brother as soon as I'm in Midtown because it was in Midtown or something like that I call my brother I said I got it we're going to start a consultancy I didn't even call it an agency yet wasn't really even an agency but I couldn't believe that it was 2008 going into 09 and I couldn't believe the biggest companies in the world didn't understand social media because I've been committed since 06 and that's probably one of the first times I've learned about timing I'm just talking about it right now with live shopping I'll say it again I don't think I'm a Andreessen Horowitz invested in whatnot a long time ago I'm not a genius I just feel like in this nanosecond that everybody's underestimating how big it's going to be.

54:57And I didn't understand that. I didn't understand that it would take that long for people to get it. And as it got bigger, it got slower, right? I didn't know that. Entrepreneur land, information and action goes faster than it does in corporate land. And so I was like, wait, there's an opportunity. They still don't get it. And so that's why I decided to start VaynerMedia. Which is also blown up. Yeah, I mean, VaynerMedia started in the conference room of Buddy Media. With your friend Mike Lazaro. Yes. And you got equity for building a website. I got equity for giving a quote, not even building a new website.

55:31Which they lettered, and they sold the company to Salesforce for a billion dollars. Yep. That was a good outcome for a quote. For me, I did extremely well. I literally made seven figures to give a quote, because at that point I'd written a book called Crush It. That was the first time I'd hit the scene outside of the wine world. and very quickly after there I was starting to be viewed as an angel investor with the super angels Tim Ferriss and Dave Morin and Chris Saka and Kevin Rose and Travis Kalkin and I was definitely in the game, Kalkanis I was in the game in that era 2006 to 2012 it was a very good era for my personal brand with books and speeches and investing and VaynerMedia is something I'm very proud of we literally started it in a conference room and it's a$350 million a year revenue business now with 2 ,000 plus employees and we're definitely the most progressive contemporary agency in the world.

56:25And it's also been the foundation of my other behaviors. I started Resi inside of there with Ben Leventhal. 2014. I started Empathy Wines, which I sold to Constellation with Nate and John, two former interns in that company. 2019. And then VFriends, which I believe, and it's fun to put this on video, to look back on in 20 or 30 years from now, but I'm in the midst right now of building an intellectual property. I'm very affected and inspired by Pokemon being worth$100 billion. I do not think people realize how big that company is. I also am very inspired by Jim Henson, a real creative force who really wanted to leave a deposit of good on the world, Fraggle Rock, Sesame Street, Muppets.

57:08And so, yeah, I'm building VFriends and a lot of the talent that works inside of VFriends came from Vayner. So Vayner has been an incredible company, but it's also been an incredible incubator of talent and osmosis of like how I want to do things. And I'm very excited about it. So I'll tell you back in my life in 1999, I'm on my honeymoon with my first wife in Hawaii at Huala Life. I don't know if you've been there or not. Oh, actually I have. I spoke to Brian Jordan there. And this guy next to me is reading a magazine that no longer exists, the industry standard. And I said, hey, are you in the business?

57:47He said, yeah. I said, what's your name? I said, my name's Ron Conway. And so talk to us about Ron and the influence you had in your life. And then let's go back. Google was started in 2005 and sold one year, nine months, and 28 days later for$1.45 billion. And you read something about that. And then as part of the story, tell us about how making bad decisions on emotions is a terrible strategy. And you can talk about playing cook from Twitter and how you got that deal. And then talk about Facebook, Mark Zuckerberg, your dinner, and then his parents. Got it. So that whole Silicon Valley era for me started with, so now I'm right about email.

58:31I'm right about the website. I'm right about Google AdWords in 2005. And here comes YouTube. and I see that and I'm like, fuck, I'm gonna build my dad's store with this. So I've used the tool of web. I've used the tool of search and email and here comes video online and I start using the tool. I start Wine Library TV on February 21st, 2006, less than a year after YouTube comes out and I wanna take a moment right now and give a huge shout out to Eric Kastner. Eric Kastner was my lead developer. one of the most progressive things I've done in my life was the day I started working in my dad's store full time, May of 98, I told him from the day I started, I will take nothing in my salary, but we need to hire a computer guy.

59:17That's what I called developers back then. We need to hire a computer guy. And by 2000 or 2001, I was able to finally get to a place where I was able to hire Eric Kastner and then later John Casamanis, who's still our CTO. And we're a fucking liquor store in New Jersey and I have literal developers full time on my staff. It was so progressive. It'd be like if I hired astronauts right now. Like it just made no sense. Anyway, I want to give a shout out to Eric Kastner because without Eric Kastner, a lot of this does not happen. He was the one that sat closer than you and I are sitting right now at my desk and was like, read TechCrunch, read Metafilter, read White Web, read Dig.

59:57He was the one that showed me Web 2.0 and during that journey, he showed me YouTube because I asked him two years earlier if I could do videos on the site. And he said, no, too expensive to host. Now we found this, they were hosting it. So now I'm doing YouTube, I explode. This is where my career really takes a turn. The wine show explodes, and then I'm now really starting to get into this tech stuff and how do I use it to build a wine store? But it's still wine store, wine store, wine store. And then Google buys YouTube. And one point, you remember this. that number I don't think the kids can now everything's inflation you remember that number?

1:00:351.45 billion do you remember how everyone reacted? it was insane I'm saying it right now because I want you guys to hear and be affected by it it'd be as if you woke up tomorrow and TikTok was forced to sell and sold for a trillion it's like you couldn't we didn't see numbers like that everything was big numbers were hundreds of millions I mean Flickr sold for 40 million to Yahoo and that seemed like a trillion Flickr was the precursor to Instagram. Anyway, I'm just like, holy shit. And now I'm a little bit older and I'm reading more business magazines, not just wine. And I read a Wall Street Journal article about the sale because I was fascinated.

1:01:13I felt different this time. I was like, fuck man. I feel like I know, I feel like my talents are not being maximized. I'm using these things to build my dad's business. There's got to be a way. I just felt different. I was just reading everything about it. And one article specifically, it references Ron Conway and it says angel investor, I'd never heard the term in my life. Angel investor Ron Conway made a gadrillion dollars, I don't remember how much he put in or what he got, but it was staggering. It was like, for his $100 ,000 investment, made$4 million or, I don't know, it might even be, it was just staggering.

1:01:44I don't remember the details. I just remember immediately going from print because it was, I think, the journal to computer and Googling, not Ron Conway, Googling the term angel investor. Googling it. Ironically, very, very apropos. And I'm like, huh. And I literally, again, said to myself, I'm going to be an angel investor. I'm going to build up some savings. I had some savings at that point. And the first, one of the first videos I ever made that wasn't a wine video was called Facebook should be worried about Twitter. Because Twitter just come out. I I was again fascinated by it. And I promised myself after the Ron Conway article that the next time I felt it, that I would invest.

1:02:35And the next time I felt it was Twitter. And that video went viral. Blaine Cook was the first CTO of Twitter. First developer. Developer, thank you. And I met him at South By because now I'm going to these conferences. And he, Twitter, I don't know if, were you in the mix, you remember this? I was in the mix, but not, didn't invest in Twitter. Do you remember that Twitter would go down all the time? It was, yeah. It was down all the time. It was the hottest app in Silicon Valley, but it was down, down, did not work all the time. They did Ruby on Rails early on. It was complicated. He was getting so much heat.

1:03:12I met him for a taco at South By, and he told me he was quitting and selling every share, and did I want any? First, and I'm really proud of this, back to being a good person. first I tried to talk him out of it. I said, I think you're making a huge mistake. Second, I could see he was making an emotional decision and he just went the whole way and a couple weeks later on emails, like, do you want to buy it? I'm done. I'm like, Blaine, he's like, I'm done. And so me, Fred Wilson and Kevin Rose, if I recall properly, bought up all his shares. That was my first investment. And then - And he left$700 million to$2 billion on the table.

1:03:46That's right. Just staggering. And then - Oops. and then several months later because I become friendly with my video went viral Facebook Dave Morin asked me to speak at Facebook Zucks was there we had dinner that night we hit it off we started to get to know each other and his sister Randy called me one night when I was in Miami at a speaking engagement said our parents Mark wanted me to call our parents are looking to sell some shares they're going to buy a nice home near us in California because they were still in Connecticut would you like to buy some Facebook equity and I said absolutely.

1:04:21I literally took 80 % of my savings and invested in Facebook. Congrats. Thank you. I've never sold a share. I promised myself that night that as long as Mark was the CEO, I'd never sell. All right, so let's go a little quickly on some of these. You've invested in over 100 companies. What do you look for when making an angel investment? Early on, I went for the horse. Then I went for the jockey. Now it requires both. The horse was the idea. Biggest mistake I made as an investor early on as a kid, a kid in my 30s, was I, if I liked the idea, I could see how I could run it to success. I didn't realize I was a good operator yet.

1:05:00Then I learned that that wasn't always working. Then it was about the kid. But even with the best operators, if you're operating a bad idea, that also won't work. So now what I look for in angel investing is the jockey and the horse, the operator and the idea. And so what's the best way to pitch you? I read what you're going to say and what I would give is my answer is very different what you're going to give is your answer. What's your answer? My answer would be to come in prepared and if you have to get in the door and you don't know me you can create a ridiculous PowerPoint presentation that blows you off of your chair and I'm good on the preparation we'll talk about that in a few minutes but I prepared materials for people that they have to respond right because you know when you open this document, holy shit, did this take 40 hours to prepare or more?

1:05:50This thing's like a Rolls Royce. It's a Ferrari on steroids. And if someone's putting that much work into it, it shows the amount of thought, progress. It's brilliant. I've received a few of those sometimes. A lot of my deals, most of them, 99 % of them come from people I know. Right? And so it's a self-selecting process. But every now and then I get something ridiculous in the mail. We've never invested in a cold deal like that, but we've come very, very close. Interesting. Yeah, mine's the opposite. And this goes back to self-awareness. This goes back to like, you got to know yourself. Like, I always say everything works.

1:06:25Everything works. Like, there's a version of success and happiness that comes in so many different sizes and shapes that it can work. For me, I don't even consume decks. My team knows this. Like, to really prepare for me, I need to have the dialogue. I need to have the feel. Like for me, at this point, to your point, so much comes from word of mouth, different angles, but what really gets me is if somebody says something that I believe in that I can follow up with a couple of questions and they can answer it. For example, what cliche happens to me is I make a big stink on something like this about live shopping.

1:07:05Now I'm going to get pitched. This is real. I know. That's what I was thinking when you were saying that. I said, oh my God. I'm going to get bombarded. Yeah. I won't look at most of those emails. I won't go for the Rolls Royce deck. I will go for the person that finds me somewhere or I get a meeting through a person because I want to, if somebody co-signs someone, I'll take that meeting. But it's not what they say to me. It's my follow-up question. I really tend to invest in things I know. More and more, by the way, as I get older. and so I know what I'm talking about with live shopping so to me I enjoy the back and forth because the other thing I think I do well is push I push well in dialogue to like real places and most people can't answer those real places you know this a lot of founders are very good at the surface level conversation but when you poke and prod they fold like cheap chairs what the craziest thing is you ask someone about, they talk about run rate.

1:08:02Run rate doesn't apply to the cash in the bank. So I always ask, what are the gap revenues? You know how many CEOs know what their gap revenues are in the last three years? Less than 1%. And for me, the meeting's over. Right? I mean, if you don't know your finances well. And so for me, you're referring to things that are a little bit further along. I do so much early stage that to me, it's almost the reverse of, I love you for that. That like, that just, I wish people knew how nerdy I am with business. That just got me so fired up. But that's obviously a little bit of a later stage company in that scenario.

1:08:31For me, because I'm so intuitive of consumer behavior, I get excited about them having to answer pre-revenue, since I do such early stage, real questions about consumer behavior. And I'm so in the traffic. One of the reasons the Gary Vee brand still lives and I run the agency is I never want to be away from the dirt. Yeah. Let's talk about your views on marketing and and day trading attention. And we'll go back to Jab, Jab, Jab, your favorite number five. So talk about that book in particular and what you want to call it. And I know you want to call it something else. So what we did is we actually made you a new book.

1:09:11I'm so hyped. And here's your new book. It's actually Jab, Jab, Jab, Jab, Jab. So congratulations on your new book. Thank you. I'll show it to everybody. That's awesome. It was supposed to be left hook, by the way. Jab, Jab, Jab, Jab, Jab, left hook. So this book I wrote, because I realized no one understood what was going on with content on the internet. By the time I wrote this 10 years ago, 2014, there wasn't a lot of science around the art of a post. I believe as we sit here today, my friend, that the best social media organic post, just post on your account, is a more important form of advertising than any television commercial on television today outside of Super Bowl.

1:09:54The individual post. You said the Super Bowl, which costs$233 ,000 per second, is the greatest marketing spend on TV. It is. No, no, in America. In America. Here's why. My newest book, Day Trading Attention, I do believe that I sit at the top of the organization that is the best marketing firm in not wasting a penny on advertising and getting the most for a penny. And that requires a lot. I, Gary, and VaynerX, the holding company, cannot get 130 million Americans, cannot get 130 million Americans to consume a video for 30 seconds for$8 million. But the Super Bowl can. No meta, no Google, no all the other things, influencers, TikTok, there's no combination that can get there like the Super Bowl can.

1:10:48The problem is if your video's bad, you just wasted all the money. The creative is always going to be the variable of success. But buying the attention, yes. In buying the attention, the Super Bowl is the best. Let's talk about ingredients of success. What's more important, work ethic, talent, or passion? Yes. Look, you know this. I mean, look, the reason I like work ethic is it feels very controllable. It's like working out. Like, you can get there. working out came really not natural for me. I didn't do it at all until I was 38. Like at all. I didn't have a muscle in my fucking body. So if I, who despises it to this day, can get to a level of discipline that gets me there, I believe people can do the same professionally.

1:11:40I also believe that it's a lot easier to do that level of work ethic when you're actually passionate about it. so it's a very the reason I answered the way I did yes all three different for every one of us in here but of the three work ethic is controllable and it's something that I get scared that people try to downplay look as someone who's unfortunately been tagged with hustle culture and things of that nature I have been consistent had Ariana Huffington on the Ask Gary Vee show a decade ago I believe in sleep I just think work ethic matters not to burning yourself out and being sick. That's stupid.

1:12:21I am worried that people are using health and wellness and mental health and all these great things that are important as weapons to create entitlement or to create laziness or to justify non-action. And I think that's a mistake. I believe that work ethic is the most important ingredient in success, of our success, because as you said, you can control it. I have something called Philo, first in, last out, and I do a lot of coaching as I know you do as well. I tell every young professional, even mid-professionals, that come to me, hey, I'm not liking my job, whatever. If you're the first one and the last one out, great things are going to happen to you no matter what.

1:13:01I think that's exactly right because even if you're in an environment that doesn't reward that, you're going to learn that it doesn't instead of leaning on excuses, which will empower you to make the tough decision of leaving. I fully agree with you on that. Let's talk about my favorite topic, which is preparation. I'm writing a book called Extreme Preparation. I always want to be the most prepared person in the room. How important has preparation been in your success? And are there any examples you can give about your extreme preparation leading to something successful in your career? It's my entire life.

1:13:33So my favorite thing, and Sid just stepped out, but Dustin's here, so I'm going to look at him. Dustin actually probably knows this better than Sid. the thing that baffles all my top executives when they started my company is I go into meetings cold and dominate them they think I do no prep they make me huge decks and because of the way we do our decks they can see I didn't open it I walk into the meeting brand new client and they are baffled it's one of the best compliments I get it's it's so flattering they are it is by far are the number one chatter conversation of VPs and above when they first joined the company asking all the other OGs how the fuck did that just happen?

1:14:17It's because I only am prepared. It's the only thing I do. The reason I can walk into Nike or Smart Water or a t-shirt brand or Lexus or any brand and crush a meeting is because most businesses are not that complicated. I can promise you that what Smart Water wants is to sell more Smart Water. And if they're meeting with me, I'm not talking about supply chain. We're not talking about other things. We're talking about demand creation. So I think preparation is the only thing. The reason I do such narrow things is they're the things that I'm preparing on at all times. The reason I have VFriends and WineLibrary and WineText.com and Gary Vee is I have to actively work on the craft of marketing and demand creation to feel like I have any ability to talk to anyone about it.

1:15:06I'm a full practitioner. Of the moment. I can speak about live social shopping right now with the expertise I can because I sold$130 ,000 worth of clothes on a live stream a week ago. So I think you're on to something very powerful. I would argue that the bad version of it is school and the good version of it is sports. I'm always prepared because I never talk about anything or act on anything or involved in anything that I don't actually do. I think some people study, but they're not about it. And that's where the vulnerability, even with prep work, comes in. Because when people start poking and prodding, you start going to 301 instead of 101 level preparation.

1:15:49So I think the ultimate preparation is to actually be a practitioner of. That's why I love entrepreneurs that are investors. They lived it. How important is setting goals in our success? And do you believe in writing them down one, three, five, or seven plan? Seven-year plan? I think about this one a lot. So again, I play it a little looser, as you can tell, than black and white. Obviously, I've had a goal since fourth grade of buying the New York Jets. I'm sure it's had an impact on my success. Right. They're worth$7.3 billion today. And it's moving fast with private equity coming in. Right. Are you going to buy them one day?

1:16:22I think so. My intuition now is that as I get older, I'll start to put myself in a position for extreme wealth creation if I want to. But I'll be honest with you, just to be very clear, the chase of it is the great enjoyment. It's a lot of fun to chase that fucking football team that's pissing me off right now. Anyway, you know, I think people do it different ways. I've learned that I'm not a reader and writer. I'm an audio and visual guy. And so I talk to myself a lot about things I want to accomplish in personal life, professional life. Yeah, I think knowing where you're going is a good idea.

1:17:00But I would argue that the ability to adjust and not be rigid to them is equally, if not slightly, more important. If you're going to do this thing in five years but clearly something's happened, putting your goal on a pedestal when it does not contextualize the truth of your life at the moment you're in right now is a vulnerability. I think people look at you, they look at me, they look at all these other tech people who have done very, very well and they say, oh my God, that person is rich, they have nice things, et cetera, et cetera. And I think everyone wants to be a billionaire. Not everyone, but a lot of people.

1:17:35And I think that's the motivation. So what's your advice? And look straight in the camera. I mean, I talk about this till I'm blue in the face. People who are motivated by money are generally not as successful, and they're generally not always happy either. Either, you know, listen, I've read, I think you know this. I talk about this at nausea. I'm going to say this to the camera. I'm extremely deeply empathetic that the response to this for most people is, cool, rich guy, but I'd like to find out. Like, fuck you, easy for you to say, I'd like to find out. We have the luxury of spending time with people that have it, and we know how dark some of their lives are.

1:18:18There is just no correlation in any kind of common sense way of money and happiness. It just doesn't, it's black and fucking white. So what I would say is, God willing, if that's what you want, you are able to earn, not be handed, your way to a place where you have it. And I'm going to tell you right now, when you get there, you will see how right we are. Period. Your dad, at one point, said you're going to be the next Oprah. And at VCon, he wears a hat that said, I'm Gary V's dad. Yes. And he's so proud of you. How does it make you feel? unbelievable other than I wish he wasn't so one dimensional and spread some of that love to my siblings sometimes it's unbelievable and my dad does it very publicly and my mom does it very quietly and they both mean the same making my parents proud is probably my strength and my weakness it's a big currency for me I really like making them proud it feels really good we're at the end of the show and I always end it with of a game called Film of Blading to Excellence.

1:19:26Are you ready to play? Ready to play. The biggest lesson I've learned in my life is? Losing is the thing you should always strive for because it makes winning a lot easier. My number one professional goal is? To buy the New York Jets. My number one personal goal is? To have everybody that I love show up to my funeral with a very good feeling in their stomach about who I was. my biggest regret is my biggest regret is already realizing that as much as I keep an eye on it I want to spend even more time with the people I love the one piece of advice that I give to my kids is be a good human being on their terms not how you want to define it the craziest thing that's happened in my life is fucking all of it brother you know i am not detached from how miraculous my life has been and silly things like judging the miss america contest when that was something i watched with my mom um to important stuff like getting an email weekly from someone who says that a piece of my content took them out of not only a dark place but sometimes the darkest scariest moment of their life.

1:20:49It was super humbling. You read your own email? Yeah. The funniest thing that's happened in my career is? The funniest thing that's ever happened in my career? I mean, probably my first appearance on Conan O 'Brien. I could not explain to you how going from operating a liquor store to literally being on the hottest late night show in television in 2007 when that was a whole different game than it is today. It was, and it was funny, if you actually watch the clip, It is actually funny, so I think that's the funniest thing that's happened. The best piece of advice I've ever received is? You know, I know you've seen that because you've done your research.

1:21:28Fuck, man. I'm really glad my dad tightened me. Again, I wasn't going to go sell, like, junk bonds. But I just know that I couldn't be sitting here at the level that I'm at if I didn't fear, like, if I didn't put my reputation on a pedestal. 10 years from now I'm going to be doing exactly what I'm doing now waking up and working on what I want to 20 years? are you ever going to retire? no and I mean this not only am I never going to retire my great preference at this point God willing is that I'm always operating retirement comes as you know in all shapes and sizes people go to consulting people go to full time investing I define it as operating I prefer to be operating something for the rest of my life.

1:22:18If you could pick one trait that's led to your success, that trait would be? It's hard because I love traits. I was about to answer humility, which is not very seen in Gary V's content. You got to really know me. Then I was about to say patience because it has been huge. But I'm going to go with tenacity today. I'm fucking tenacious and it matters. the one trait that is most important to somebody else's success who you don't know is so the one trait that i deem is most successful to someone else's like universally a trait that is a good indicator to success yes tenacity hard work if you could meet one person in the world who would it be if i could be someone if you could meet one person in the world today who's alive who would it be who's alive we got you this is important because i've never because the macho man randy savage is dead if i can meet one this is this is a very interesting indicator of me i am so insular i'm very curious it could really be a lot of people if i could meet one person in the world that is alive who would it be

1:23:41you know who I'd like to talk to right now? Vince McMahon. Have you seen the Netflix? Have you seen the special? I'm only two episodes in. Let me tell you why Vince. There's so much there and I'm sure that surprised a lot of people and I'm very empathetic that there's plenty of there. But the angle in which I would want to talk to him and what I would want to talk to him about is strictly around character development. I believe that everything I've accomplished in my career will be dwarfed on my execution of V Friends. I believe that in 30 years when I sit here and do an interview with somebody as awesome as you what they're going to want to talk about is V Friends nothing of what we talked about.

1:24:22Sure they'll touch on it. I believe that Walt Disney and Vince McMahon and Jim Henson are the prominent figures of modern character development. Jim Henson and Walt Disney did it with fictional characters Vince did it with real human beings, which I think is very fascinating. The other two are dead. So character development, how to get people, by the way, you know who my fourth one on that list is? David Stern. David Stern understood that Michael Jordan and Larry Bird and Magic Johnson needed to be superheroes, not human beings. That's what sports is. Steph Curry's a superhero for little short kids, not a basketball player.

1:25:03And that's what I'm gonna do with my V friends and that's why Vince in this moment. If you could go back and give your 21-year-old self one piece of advice, it would be? Don't do a single thing different because at 48 and a half, almost 49, you're a very happy person. The one question you wish I had asked you but didn't is? You know, it's so funny. I don't think in that term because when I'm sitting in this seat, I think I'm here to bring value for the audience. Thus, I have no feelings towards questions. You know your audience better than I do. You're awesome. I want to do a shout out to Mike Hermelin.

1:25:44Yes. We wouldn't be here but for him today. Yes. I just met him. He's a new parent at our kid's school. He just moved to LA, as you know. Yes. He'd been here five weeks. He shows up at back to school night and randomly we start talking to him as we're walking out. That's awesome. We start talking. He works at Fanatics. I know someone there. Here we are. Here we are. I really appreciate it. Thank you for having me. Thank you. Thank you. Bye.

From the publisher

In this episode of the GaryVee Audio Experience, I am joined by Randall Kaplan. We dive deep into the age-old debate: Are entrepreneurs born with a natural talent, or is it a skill anyone can develop? We explore fascinating stories of childhood entrepreneurial ventures—like selling flowers from a neighbor’s garden—and dissect the mix of talent, grit, and curiosity that drives business success. You'll hear candid insights on what separates natural-born entrepreneurs from those who put in the work to excel. Plus, we discuss the role of environment, motivation, and what it truly takes to thrive in the business world. Whether you believe entrepreneurship is a calling or a craft, this conversation is a must-listen!

Be sure to Check out Randall:

https://linktr.ee/randallkaplan?fbclid=PAZXh0bgNhZW0CMTEAAaZTkLD8sQUoE48fcbhHzGzyP3lYq8hm42zef-zEzQtNUAPatW8bYCFDrRY_aem_9zsMuzYAyeEKNrJPLXGRnA

Can Anyone Be an Entrepreneur? | A Conversation w/ Randall Kaplan

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