GaryVee: From Earning $2 an Hour to Running a $350M Digital Empire

[00:00:00] [00:01:00] Ilana Golan: This is going to be such a special episode. So first of all, Gary, the fact that you let us into your home and just seeing this, feeling this, we are live in VaynerMedia with the one and only Gary. Gary Vee: Thank you for having me. I'm so happy to be a part of this. Ilana Golan: For those who lived under the rock, which I have until about 2016, we talked about it. If you haven't heard of Gary, Serial entrepreneur, I think is an understatement for this guy. Like he is all over so many ventures. He has what? 44 million followers. I don't know. Incredible. He is an author. He is a podcaster. He's invested [00:02:00] in Facebook, Tumblr, like snap, Twitter, Venmo, et cetera. Gary, we chatted a little bit before we started, you were entrepreneur from. Day one basically, but I want to take you back in time So this is going to be all about your career and how you got to where you are and you A small kid immigrant family. Yes Why? Gary Vee: It's almost like the reverse It's funny when you just said why, the answer that bounced in my head is why not? Meaning, I had no choice. I cannot explain in any other way than I'm about to why entrepreneurship was my life. Me gravitating towards entrepreneurship when I was six with lemonade. Or when it would snow, instead of, you know, I would play a little bit, but if there was two snow days in a row, it was impossible that I was sledding, snowball fighting, playing football in the snow, and making a snowman. One of those two [00:03:00] days, I was ringing doorbells, shoveling snow, washing cars, trading cards, and everything I've done in my career. The only way I can explain it is, if I was to ask everybody on the other camera right now, why do you breathe oxygen? Why do you guys breathe oxygen? Ilana Golan: It's just an instinct. Gary Vee: There's And not every entrepreneur Is a terrible student, but I was, and I think there isn't reason. I believe that I was willing to die on the hill of entrepreneurship. I could not think about anything else. And I was willing to face the ramifications, which at that time meant that I would be grounded multiple times a year by my mother. This is real. And by the way. I used to get very aggressive anxiety come rapport card number one time because I knew I was walking into a firing squad. I was going to be punished. This is like clockwork. I would be punished three times a year because my mom kind of let me go for the summer three times a year I would be grounded For two weeks, with no television, no [00:04:00] video games, and no friends, and it was devastating! And yet, even with that, I was not willing to get C's, which, in hindsight, I feel I was very capable of doing. Because I needed every minute to study my baseball cards, to sell my baseball cards, to sell pencils, to sell gum. To think of a business idea, to make a movie, to make a song, to sell. I was creative to sell it. Me and my buddies, let's make a rap song in 86 when it was hot. Why did I do that? So we could sell the tapes. It was business. Ilana Golan: Do you think your dad's entrepreneurship was part of it? I think, Gary Vee: I think from a genetic standpoint, to be honest, my father worked every minute. I never saw my father. It wasn't like my father was at dinner. You know, like how some entrepreneurial parents are like teaching their kids. Like I am with my son, specifically. I didn't have those kind of talks with my dad. I was aware that my dad went from being a stock boy to being a manager at a liquor store to eventually being a partner and owner in liquor store. First of all, [00:05:00] the word entrepreneur Ilana Golan: didn't exist Gary Vee: as we know, he had a business. I did not make the connection in my youth, even into my teens, that my spirit was tied into it. So I don't know if I was affected by him doing it, but I do feel I was affected by him giving me that entrepreneurial DNA, of course. Ilana Golan: And in retrospect, the more I read about him and your mom, it's amazing how incredible, I mean, they moved across the ocean. You know at a time that entrepreneurship didn't exist. I mean Barriers Gary Vee: timing like I was born in the soviet union. We got out with political asylum and we Were able to come to the us in 78 Jimmy carter just passed and a lot of people talk about his incredible life and he was an incredible man But the economy during his tenure was quite weak I mean weak land in america my parents here in russia the soviet union that america the streets are paved with gold Well, we go to the [00:06:00] hood of Queens at a time where people can't get gas, you know, so it was a rude awakening, but the promise was true, which was, no, the streets were not paved with gold, but the American dream was alive and well in 78. And to remind everybody right now, it is alive and well now the opportunity is extraordinary. by most standards and um, if you put in hard work as a foundation and then you have good strategy and serendipity and some fortunes, have the ball bounce your way, there's real opportunity and I won the parenting lottery my father, we had nothing and it was important for my father that my mom stayed home and raised us so he supported on his back 15 hours a day, that reality and then lucky for me, that mother ended up being the best mother of all time And parented me in a way that makes all the accolades and all the kind things that are said about me [00:07:00] very easy for me to stay humble, because when I hear them, I don't think that I did it. I think I'm the byproduct of Sasha and Tamara Vaynerchuk. And that makes me happy. Ilana Golan: And it's amazing because also in your books. You tell us to write your dad and that's that's going to happen because I wanted him to tell him about this meeting with you, but how do you? Make people hungry when today they have everything. Gary Vee: So one of my favorite sayings is And this is huge for parents, I have two children, some of us who are watching this grew up with very little and now have more than they could have imagined or at least enough to do a lot of things. One of my favorite sayings to tell a lot of my wealthy friends that are parents now, and I have this conversation a lot, a lot of people connect, I think it's a very connection point when parents grew up with little and now have a lot, they're always stressed about this question. My number one belief in this is you cannot be hungry when you're fed. Ilana Golan: Right, [00:08:00] and I love that quote. I even wrote it down. Yeah, Gary Vee: and I believe in it and what it's meant to say to my friends my new friends that are watching right now or listening is Look, you can't fake environment if you live in a bougie neighborhood and you fly private like your kids are living in that environment. You can't be like, well, you should be more hungry. Well, it's that's hard so I think there's a couple things to think about. One, what do we as parents and human beings value? I, for example, do not value my children being overly financially successful. And that is not because I have, and I think they'll have. I'm not even sure I'm going to give them anything. It's because I have now lived 49 years, and I've got very fortunate. The first half of my life, I lived in environments that were lower. And sometimes middle class. Last 10 15 years of my life, I've been around extreme wealth. And I can sit here, whether one wants to [00:09:00] believe it or not, and I can without any concern, with quite ease, you know where I'm about to go, tell you there is no correlation of financial success with actual joy. I know right now, I can look through my phone from A to Z, and I would never do this, but I could rattle off to the audience right now. Not dozens, hundreds of human beings that I personally know who have tens, if not hundreds of millions of dollars in their bank account. And they're not happy. And are borderline suicidal. Are drug addicts, are deeply depressed, are anxious. Me, I'm one lousy human and I can give you 50 to 60 easy, probably 100 right now. That I know, right this second. I think there's an incredible misconception. I believe it is one of human beings biggest flaws that they have bought into this baloney. So, for me, what I would say is, look. I don't want my kids to be lazy bums, but I want my kids to be passionate, happy, yes, of course, [00:10:00] fulfilled, joyous, passionate, like, if you get up in the morning and you're fired up, whether you make 40k, look, if you make 45, 000 a year, as long as you live a 45, 000 a year lifestyle, you could be good, and I'm not naive to the hardships of it, but again, you don't need to live in New York City. I love when everyone's like, you know, making a hundred K in New York City, you can't even live a life. So I'm like, leave New York City. Do you like that? Like, like, I love accountability. Accountability is my addiction. If you can't, I don't know. Like, I was just in Montana. Do you know how many happy people live in rural areas where cost of living is different? And by the way, don't even get me started on It's 2025 right now. People can have remote jobs. People can zoom into every meeting. And you also don't have to, if you're complaining about money, you also don't have to buy 7 dollar cups of coffee from Starbucks three times a day. Like, people don't know how to manage their money. People live above their means. I [00:11:00] know millionaires that are broke. People that earn five, six, seven, eight hundred two million a year, but they spend more so there's money management issues You the credit card created a huge pandemic Ilana Golan: I always laugh the more you make the more there's ways to spend it, so you somehow at age 14 Join your dad. Yes in a wine business Gary Vee: Liquor at the time. Shopper's Discount Liquors was the name of the store. Ilana Golan: And even sell wine at age 16, which is not even allowed to like drink. Talk to us just a little bit about what is it like for you? Is that forced? Is it felt great? Is it Gary Vee: It was terrible year one. 14 to 15 weekends and summers was devastating because I was making a lot of money. Hundreds of dollars a weekend selling baseball cards. I'm being my own boss. And by the way, having thousands of dollars consistently when you're 14 in 1988, 89, I'm not sure I'll ever be wealthier than I was back then. Cause I at one point had 10, 000 [00:12:00] and that was like 40 billion now you, I didn't even know how to spend it back to like the thing you said earlier. And now all of a sudden, I'm cruising, I'm the man, I'm feeling good, and my dad walks in and goes, you're coming to the store. I'm like, which store? The store. And now I have to work for two bucks an hour. Ilana Golan: I thought it was five. Gary Vee: No, 505 was minimum wage, my dad paid me under the table, cash, two bucks an hour, family business, immigrant vibes. He made two bucks an hour when he started, so I have to. I was like, yeah, but dad, that was 1978, it's 1990, you know, 1990. Nope, doesn't matter. Two bucks an hour, and I'm doing hard labor. I am bagging ice from an ice machine for hours. Or, finally, a little bit, couple months in, or a year in, I'm allowed to stock the shelves. That was my promotion. Now I'm allowed to stock, like, I'm a 14 year old kid, and by the way, no thought on all the things we think about now. I'm carrying huge cases of alcohol, hurting my back, I mean, I had a bad back my whole life [00:13:00] because of this. Stocking shelves for 12 hours a day back to before we started filming lunch water didn't eat lunch. It was Immigrant 101 son of a merchant 1930s Brooklyn life That's what I was living and the first year I hated it a second year though Something miraculous happened a gentleman walks in asked for a wine I remember like yesterday came a special select cabernet from Napa Valley. He said do you have it? I said no I might be able to get it. I go, how many would you like? This is blurry, but he said a lot. So, he said three or four cases. Which, that seemed like a lot. I say, are you having a party? He goes, no, I collect wine. Do you know those moments in your life where like the C's part? Ilana Golan: Uh, yeah. Gary Vee: I was already passionate about helping my family. I was an immigrant. So like, me putting in those 15 hours, I felt like I was contributing to our family getting out of, You know, I felt proud about that. I wanted to help. And I thought it was a good businessman [00:14:00] already as a kid. I wanted to help my dad. I was still scared of my dad and didn't couldn't share my ideas yet, but I didn't like what my dad sold my mom because of all the alcoholism in Russia, demonized alcohol. I didn't drink alcohol until I was 21 years old. Which is wild. Right. My family had a liquor store my whole life. Right. I went to college like every other normal kid in high school and did not drink. Did not have a beer until I was 21 years old. Because my mom scared me so much. Nancy Reagan. Drugs. No drugs. I still to this day have never smoked anything or done a drug in my life. Ilana Golan: Me neither. Okay. Gary Vee: You know, so very, very much had a mother that was passionate about that subject. It wasn't cool to me like other high school kids of selling Budweiser or Crown Royal. Like I didn't think it was cool and it was boring compared to sports cards. But collecting because I was into collecting sports cards So I took all my energy of knowing everything about baseball cards reading the Beckett and I took it to wine I was gonna learn everything about wine because people collect it and I read the wine spectator now Instead of the Beckett baseball card guide and that [00:15:00] changed it. And so how was it horrible year one? It's been nirvana ever since You know, from that moment on, I just became incredibly educated about wine. By the time I was 18, I knew everything on paper. I didn't taste yet. You know, it's funny, I just turned 49 in November. And, you know, my parents are 72 and 70, so still young, thank God. But, I'm not 20 anymore either. And, you know, I'm going to be 50 this year. That makes you think about stuff. Those are fun things to think about. And I also think I'm going to live to 100. That's always been, like, important to me. And I believe in it and I live my life based on that will be true. And, you know, I feel like I'm at halftime, just like a good sporting event. You go into halftime and you reflect on the first half and try to adjust. I will tell you, and I've said this for a long time, building my father's business for him, and that's what happened. Just to give the punchline to everybody who doesn't know, I built my dad's business from 4 to 60 million dollars in a very short window, and changed my dad's life. But I didn't own it. And I also didn't get paid much because that's how immigrants [00:16:00] do it. So I had to leave at 34 to start my own life. I gave up 22 to 34, 100 hours a week to build a business for my parents. As you can imagine, when I left, there was levels of resentment that were real. I worked all this stuff, I was the driving force, and I've got nothing to show for it. And now I have to build my life all over again financially. Fifteen years later, It's the best decision I've ever made in my life. Giving that contribution to my parents, who I give credit to everything, feels incredibly appropriate. And, um, I'm really glad I did it. Ilana Golan: For those who don't know the story, I think it's important to go back there for a second. Gary Vee: Please, happy to. Ilana Golan: Because in 1995, Yes. I was in the Air Force. We were starting to get the winds of change coming, but you took it, somehow you always know what's coming. That's pretty incredible. And you took it and realized that you need to bring the store online and that's a big part of, and I [00:17:00] mean, you rebranded it and that's a big reason why it went from 4 million to 60 million. Gary Vee: It's the reason. Ilana Golan: So, how did you realize it and what was the change? Let's talk to her for a second. Gary Vee: Thinking about this audience, let me throw a word out to answer your question. I believe one of the most powerful words in the world is maybe. And the reason I think the word maybe is powerful is if you fall in love and become addicted to it, it stops you from the word no. So I believe if I analyze my career that the word maybe that led to yeses and noes Transcripts have been foundational for me. I did not grow up a good student. I did not have a computer in my home my entire life. I was born, and I went to college at 18, and I had never had a computer in my home. It was not part of our culture. We wouldn't have bought it, and I'm also of the age where it wasn't required. I then saw The internet in 1995 for one second. I watched a kid [00:18:00] open a lat and now we're into the laptop era So it was cool. I mean it was desktop. Anyway, a kid goes on the internet. I heard cuckoo First time I was like, what was that? He's like, that's the phone line like literally and I watch him go on AOL on different places and I decide right then and there right then and there within the first 10 minutes That this was going to change my life up until five minutes earlier, I always dreamed that I was going to go help my dad and I was going to open up the Toys R Us of wine stores that I was going to have 100 locations in the country within a moment's notice. I said, I'm going to build. This dot com thing. I'm gonna build a store inside the computer I didn't even know what I was saying But it was so crystal clear and the answer is because the second he said everybody come and see this thing Cuz it was like that. I mean there was six guys hovering over him. It was that like profound Everybody was in no culture. [00:19:00] This is stupid. This is nerd stuff. I'm gonna play basketball and I was like, maybe And I was not techie, I still can't keyboard. Thank God there's this. I will tell you that. moving our ads from print to Google, me getting in front of a camera at 30 years old and doing a wine show, me taking my life savings and investing it in Facebook and Twitter, me live shopping on social today, Web3, me buying Bitcoin in 2014 15, like, everything I've ever done. Has been because it's maybe a lot of it fails. Here's two things. I do one. I'm willing to play long I'm willing to invest my time and learn to something. I believe will be true in 10 years So I'm investing to I watch people and I think too many people make decisions based on themselves they say I Don't like social media because it's political or it's bad for the kids So I won't [00:20:00] take my dress shop and put it on social. I don't like social media I don't like anything. I just as a business person when I put on my business hat I like nothing and I watch what consumers like and then I bring value within it And so how did I know I knew nothing about computers? I had heard about the World Wide Web, like to your point, there was like an article or two, I had heard of it. So it wasn't like I didn't know what was happening, I knew it was like that thing. But the first moments of my relationship with the internet, I was coming in with maybe. And that led me to that evening. I finally got my chance to go on the computer like 3 hours later, because everybody got like 30 minute chances. And that night, I found a message board where people sold baseball cards, and I knew, and I knew. Ilana Golan: Amazing. You reminded me, as you were talking about it, because I was supposed to stay in the military five more years to bring the F 15 to Israel. And I actually left [00:21:00] and joined Intel as the youngest engineer ever, uh, that they hired until then. So that it sounded so amazing, but in 2006, I'll take you there for a second, because you somehow understood the power of personal branding probably about a decade before I even understood why this even important. And I think a lot of our audience. Are still at the point of I gonna give a thousand percent to where I work and I will never build myself on the journey So tell me more about that Gary Vee: Ideology and not understanding nuance. Let me explain what I mean by why I just said that personal brand When the term first started hitting the scene in 2009 I was at the forefront of making awareness for it. People thought it was yucky Right? Because I understand that self promotion when out of whack is not good. And being respectful and behind the scenes, [00:22:00] there was merit. I remember in 2009, when people would get into a debate with me. At a bar, or like at a conference, or like in the halls of a conference, or at a table, or in a meeting. And I would literally say, and this is where I'm going with nuance, I would say, okay, personal brand. Let me say it a different way. Reputation completely melted the anger. People got so caught up in the semantics of the word. Why is cancel culture on its back foot right now? Because we can't fight on semantics of words, we have to interpret intent. When I said to everybody back then, build your personal brand, the intent was to do good by both the company and yourself, but for real talk, it was to protect protection and give you optionality. The amount of people that built their personal brands in 2008 after I wrote Crush It, that book all there in the corner. I love that, yeah. The amount of emails I got in 2010 from people that literally titled, I love you. It was a wave of love in 2010 11 for me. Here's [00:23:00] why. Many people started losing their jobs when the economy got tighter. But because they built their personal brand, they were able to get jobs immediately. And they saw that people that weren't on Twitter and Facebook at the time, and LinkedIn, did not. And they thanked me, and they thanked me, and they thanked me. And I sit here today in 2025, and I implore everyone. Listen, I always am fascinated that I was one of the Pied Pipers, because I have an extreme personality. It's very high, it's very excitable, and it doesn't work for a lot of people. Don't look at how I communicate. Find your own way. Right, you don't have to dress down, you know, if you find me on the internet, I curse a lot, you know, you can see I get excited sometimes I a lot of things that won't work for you, but what works for you, that's right, you can wear a suit and be articulate and be respectful and talk slow and whatever, just get your ideas into the world, there's no downside, https: otter. ai The only insurance policy you've got, Ilana Golan: I love that you just [00:24:00] said that, first of all, because I needed to fall really deep in order to realize that I didn't build any safety net. I was a complete nobody. I'm starting from scratch. You reminded me of that. And if I just built myself and this is what we do in Leap Academy, we're trying to help people elevate themselves, at least tell your story, understand what's your zone of genius, start telling it to the world. Ilana Golan: Because Otherwise, you're just your title, or you're just the company that you're with, and you call it brand equity, which I just love that term. Gary Vee: And again, those are marketing terms, and I'll say it again, because I love the mission of Leap, and what you're doing, reputation. Why, if you're good, or you know something, or you've done something for a long time, Why wouldn't you want as many people to know it as possible? You're literally one video away. For this crew, everybody here is one video away. Posted on LinkedIn from getting so many things they drea Do you know how many people [00:25:00] missed out on a promotion and somebody else got it? And they're upset and angry? But they're golden handcuffed, they can't leave the job. If they make a post, not No, no, I want everybody to hear this. Not bashing their company. No, no, talk, let's say they're in um, SaaS, software sales. If they make a video and say, I'm Johnny, and let me just talk to you about the industry as a whole. Here's some three tips I've learned in 20 years of SaaS salesmanship. A CEO of a SaaS company might see that and be like, wait, I like Johnny. Let me offer, let me DM him and say, do you want a job? I mean, All of this is back to what I said earlier, which is ideology. Some people feel that them putting themselves out there isn't respectful, isn't classy. Or even worse, they're insecure and they're scared what people are going to say about how they look. Or that somebody says they're dumb and then they stop. The amount of people that have listened to my content for 15 years started and then stopped within a week because somebody said they're ugly, or they're stupid, or who do you think you are? And I [00:26:00] remind everybody who's watching this. You left high school. High school is over. Getting made fun of cannot stop you from building your life, and I implore you to do that. Ilana Golan: let's go there for a second, because you're absolutely right. Probably one of the biggest fears is the hate. And today in the digital world, it is a little easier to hate and to give a bad comment and to, you know, not to send you, I love you, but to send you, I hate you. Gary Vee: That's right. Ilana Golan: So how do you create a tougher, maybe a thicker skin or something to just let the noise go away? Gary Vee: If you're one of the people that is crippled by that, me sitting here on this podcast and unwinding parenting and circumstances that have led to insecurity is going to be incredibly challenging. So that's the real answer. The real answer is, everybody here needs more actual self esteem to be able to combat it. You know, a lot of parents are like, social media is bad, I'm going to take the app off the phone. Fine. [00:27:00] Good. Allowed. I get it and I think moderation matters. Comma, you're not going to protect your child from real life. Like, real life happens. What you really need to do is build self esteem so that they have the strength. To make good choices give them tools to cope with what are we doing here? So what I would say to everybody is if you're a grown up and you're still a child meaning you're insecure Here's a series of questions that work for me. Do you really want your entire life's happiness to be predicated on? Johnny Pants 4, 7 3 saying that you're like, you know, it's, this is why we all laugh. Like, you know, like it's, it's why everyone's giggling behind the, like, I don't know what else to tell you. Like, I, I, I believe, and I hope you, I hope you agree with me, that it is incredibly ridiculous to let your life be dictated by an anonymous person on the internet. And we collectively as 8 billion people. Need to get over to hump the reason I've been able to do so much and put myself out there is Someone might be right, [00:28:00] you know 50 people like this is silly Gary that you're doing this. They might actually be right I could be wrong. I could be out of touch. I could be out of bounds But here's the powerful word next, and so what? Everyone's a human being. Everybody makes mistakes. Listen, when I'm on my last breaths, or maybe when I first enter heaven, and I have to give a, maybe we don't know what heaven is, and maybe the opening line is like, Alright Gary, you're in heaven. You've got one minute to sum it up. I think my answer is going to be like, It's all just one big game of eliminating fear. If you're a leader right now and you're a CEO, what's your job? Number one, the elimination of fear. If you're a parent right now, the elimination of fear. This is why I'm so mad at mainstream media. Social media that gets a lot of rub from mainstream media has enormous amounts of fear. It also has enormous amounts of hope and love. Regular media has just fear. I'm struggling because I'm clicking the channels. Show me the optimism, show [00:29:00] me the offense, show me the smiles, I can't find it. And so, it's just fear. You want to sum up leap from my perspective watching from afar? Yeah, you were empowering people to chip away at their fears. Ilana Golan: Yeah, make decisions based on hoping dreams not fear and doubt That's it Gary Vee: because ultimately I hope everybody heard me, and so what? Let me tell you the thing I fear the most. Back to building blocks on this topic. Regret. Regret scares the crap out of me. So why do I do things that might not work out? It's because I don't want to regret. I'd rather die on my own sword than someone else's. Do you know how many people have taken the advice of their parents or friends or a colleague or their spouse and did something against what they thought they wanted to do and then it fails and they double lose? Because it failed, and now they're pissed that they knew they should have done the store instead of the online thing, or red instead of black, or, you know, whatever it is, die on your [00:30:00] own sword. Ilana Golan: And now they're in blame. Gary Vee: Listen, if you're a blamer or a complainer, I can give you a direct correlation, you know, like, right? I mean, if you're one of those two things, and by the way, everybody, please pay attention to who listens to your blaming and complaining. The only people on earth that will listen to a complainer and a blamer are two groups. One, other losing players that blame and complain, and you're just in one big circle of complaining and enabling each other, and the occasional parent that's an enabler of your bad behavior. Right, or a sibling, or someone who loves you, who's just enabling you, they love you. If you, please audit your circle, and pay attention to who listens. Because I promise you, let me tell you who's not around. Friends and acquaintances and co workers that you used to have who are positive and on the offense and they've weaned you out. Ilana Golan: Do you want to be a victim? You want to be a victor? You choose. Gary Vee: This goes back to New York City. Let's talk about America. We just had an election. [00:31:00] You know, it's been very, Israel, like the world is very contentious. But I say this all the time. I am now of the age where whether a Republican or Democrat has won, I have an entire group of friends who say, well, if George Bush wins, I'm out of here. Well, if Obama wins, I'm out of here. Well, if Trump wins, I'm out of here. Well, if Biden wins, I'm out of here. I've had that now for 15 years. So far, no one's left. First of all, that's the newsletter. But more importantly, when I have those dinners with people, I say, good. I said, good news. If you don't like it, you can move to Sweden. Great news. Kenya is amazing. Knock yourself out and that goes into blame and complaining. You don't like your job? Get another job. Oh, by the way, if you listen to me 15 minutes earlier and make a lot of LinkedIn content, you'll get another job. You are actually in control and anybody that tells you you're not, a parent, a government, anything that does make you feel like you're not in control is a poison. Ilana Golan: And I think this is so, so, so [00:32:00] important and I appreciate your sharing that. For you, you start VaynerMedia with your brother, AJ, we're what, 15 years later, 2, 000 people, 350 million, like this thing is an empire at a whole different level, plus you're doing all these other things, which I don't know how you live, but can you share some hard moments? Because I think one of the biggest things that our listeners have is this confusion about the overnight success. And a lot of these things are a decade plus long overnight success. Gary Vee: I mean really this is 43 years in the making. Literally lemonade stands and baseball cards led to where I am today. I mean the hard moments, let me give you a different counterpoint to your point that people think people got lucky or it's an overnight success. I'm going to say very real truth. I would argue entrepreneurship or running a company is [00:33:00] a series of micro headaches and problems and anxieties with the occasional micro wins or macro wins or if you go out of business, the ultimate macro loss. I would argue that when you're the number one, I always say this to a lot of friends. I'm like, if you have it in you to be a number two, go for it. I lay at night sometimes and I'm like, man, I wish I was number two. You don't get all the financial upside, but you get a nice little something. Oh yeah. And boy, you get none of what I'm about to say, which is Again, I can only explain this to people who are now parents, but are not owners of company. When you become a parent, something weird happens. Where you realize, wait a minute, this little thing? This kid? I'm responsible. Like, I'm the last line of defense. For the to over 2, 000 employees I have globally. When there's a leak in the roof in Thailand, and this is real [00:34:00] stuff I'm not talking about, of course there's people that handle that, but if it gets the fires in Ilana Golan: LA, Gary Vee: I'm deeply have to be involved with that. We have employees that lost their homes. Nobody's allowed to write a check to buy somebody a new home without me. Can't do that. But I can, if I want to, if I can afford it. When last year, hard times, for me it's all that these employees, they're not my children, but they're definitely not strangers. So when four employees go to summer vacation in my Asia office to take a trip all together and get into a car accident and one of them dies, it destroys me. Not only do I have to deal with that, but I have to deal with the ramifications of those three people, all 200 people that are affected by that tragedy. I'm gonna be very transparent and vulnerable here. We got ourselves in a real pickle in EMEA, in Europe. We had to do a layoff this last quarter. We've only had two in the history of the company. That was six months of sleepless nights for me knowing we were walking into that [00:35:00] fire. And then the ultimate day when we're letting go of 40 people? It's devastating. Those people, before the holidays? You know, and then you start to question yourself as a human being? You're like, you know, like, I know why I have to do it for bank covenants. Like, you know what sucks about business? Is it's not government. It's not academia. It has consequences. When you're in government, you just keep printing money. Let me give you the news alert, people. Those politicians don't, they don't care. but when you own a business, if you don't make payroll, you have a problem. Businesses go out of business. Families are screwed up and get whatever, but they can reconcile sometimes. Even after 20 years, brothers have been estranged. Yay! Academia? There's no consequences. Government? No consequences. This is one of the few places that there's consequences, and it's very hard. So, let me take the other side. It's only eating crap with an occasional carrot and tomato and strawberry. I'm being [00:36:00] dead serious. Now, for someone like me, I'm addicted to eating that crap. I promise you, if I really could, I don't think I would've chose it. I think I would've been a great guidance counselor. Would have loved that life, would have crushed as a coach, oh, be a guidance counselor and a coach of the sports team in the school, would have rocked. I hate that my chemicals made me want to build and be entrepreneurial. I always dream about this movie I want to create where the world learns how to take personality traits out of you and inject you with it. And the reason I came up with this script was because I've literally thought in times of my life that if I was able to take out my entrepreneurial spirit, I would because I'm such a simple guy and I would have had like such a calm, simple life. And I mean it. I mean it. Now, let me add some color to this because it's important because people are listening and people are feeling different things. I will say, for all I just said the last five minutes, There's nothing I'd rather be doing. Let me [00:37:00] not use crap because this may land better. I, this is real what I'm about to say. I love caviar, oysters, uni, octopus, frog slags, sweet breads. I eat very exotically. Very. That's my palate. I like those things. I love vegetables. I have family members who eat like steak. we're all different. So, even though these are challenging flavors, or different, or weird, like I just talked about, they're the only flavors I want to eat. And so, I love it, but I want to make sure that people know, if they're going to go into it, do they have the stomach for it. I had a moment happen, if I may, just last thing on this. Somebody committed suicide in the tech industry in Las Vegas. Remember when Tony Hsieh built out? Of course I remember. So, a startup left San Francisco, a gentleman I knew, and he was one of the 25 first downtown Vegas startups as they were building out. And he committed suicide. I was [00:38:00] devastated. And this was before even like suicide itself was less common. Ilana Golan: We didn't talk about mental at all. Gary Vee: No. And when this happened, it was very much, we were still in the naivete, nirvana era of web 2. 0. Hippie like, you know, everything's going to be great. And it crushed me. And then when I found out that the reason he did it was because his business was going to fail. It just sent me into a spiral. It had never crossed my mind. That somebody would have their entire self esteem wrapped up in their business going under or their entire emotional framework. And there's obviously many things that brings a hue. I don't want to project. But I interpreted, or the way it affected me was, I need to start talking about entrepreneurship in a way that people understand you have to be built for it. and everybody in that era thought it was the coolest thing and I was riding the wave Like no question I was getting attention for being an entrepreneur which was wild to me because I never thought being a businessman was gonna bring me Any level of notoriety [00:39:00] and I still think entrepreneurship is the best But I have for the last 15 years been very clear that this is not for everyone That being a good number two is amazing. I just said it a number set by the way the number seven at Facebook Ilana Golan: Eh, not bad. Gary Vee: Not bad? The number 7 on Facebook, if she or he has not sold any stock, has more money than almost every human on earth. So this ideology, because if you're not built for it, it is a lonely, hard place. If you're built for it, it's your place. Ilana Golan: This is powerful and I think this is a big thing that I want the listeners to understand is it's okay to be in corporate. It's okay to climb up the ladder. Just don't forget yourself and attach all your identity to this one title and one company. Gary Vee: And, that brand and build optionality. Don't over romance, uh, CEO of your own company. In fact, let me give you a weird one that you just inspired me on. How about this one? I'm dying to see what you think about this. Do you know how many people I've [00:40:00] watched make the mistake of not taking a lower title for a much better company and more growth in the future? Ilana Golan: I just interviewed the former president of Starbucks. You need to hear what he says about that one. Yeah, I'm dying to see it. Gary Vee: Yeah. I have had enough experience at this point that I've watched people I remember the big one was all the people in the traditional media companies and search companies not going to Facebook and Twitter and those companies. Because instead of being an EVP, they're like, wait a minute, I'm an EVP of Paramount. What the hell am I going to be an SVP at Twitter for? Well, I don't know, it's because if you would have done that, you'd have stock options, like, like, and you would have, like, I love what you said. Do not hold anything dear, especially something as vain as a title in a corporation. A lot of you are making bad mistakes because of an ideology. You don't have the humility. I will argue the biggest thing that is not obvious in this interview and in the way I produce content and the way I even roll. Is that if you ask me deep down, [00:41:00] what are the ingredients that made you, you and the things you admire and others that have made it, it's humility. I talk with incredible conviction and bravado here. I'm not confused by that. But I promise you, in my actions, what has absolutely made such a difference is humility. I'm very aware of what's going on with me. I promised you when you said 44 million followers, I don't know if, you know, you can't see into my soul, but I've even gotten to the place where it's a little embarrassing. Like, which is wild, because I'm proud of it, but humility is the secret weapon in the Swiss Army knife that is life and career, and uh, I hope that little rant inspired someone to maybe take a step back and think about something they're dealing with right now, and they realize their ego, which is insecurity with makeup on. Is holding them back for incredible opportunities and you know, this just happened the other day, somebody the other day sent me a message around this topic different than the way I'm saying it now and said they're 63 years old and they wanted to be a chef. But at the [00:42:00] time, being a chef in the 80s and 90s was the help. Today, a chef is a celebrity. Follow your gut, follow your dream, follow your intuition, don't worry about what people will think. This man wrote me a fucking soliloquy of like, just from the heart of how he is now getting older, and it eats him inside. That he was a financial advisor when he knows that he could have enjoyed his life and even thinks now in hindsight could have made more money if he followed what he wanted to do, which was to be a chef, but his parents and he himself, he didn't throw them under the bus, thought that was a beneath job. And so if you want to go be a plumber. Because that's in your soul and be a plumber because oh, by the way, those guys make a lot of money. Ilana Golan: Although they do work with shit, but Gary Vee: Yes! They literally do work with shit! I love you for that. That was so well done. That was so well done. Ilana Golan: Anyway, but I know I could probably talk to you for like [00:43:00] 15 more hours, Gary. You are one of the most sincere, humble, down to earth Fun people I've ever met. Thank you. So first of all, thank you. Gary Vee: Thank you Ilana Golan: Maybe last thing that you would say to our audience Gary Vee: I think in the energy that this took and by the way I'm enjoying this so much and so sad that I need to run that I'm throwing it out there into the ether I'm not against a part two at some point in the near futureI'm gonna leave you with this sentence. I believe that life is how you see it if you decide it's bad And the world is traumatic and horrible, then it is. Then it is. And if you decide, between AI and social media and live shopping and, and the phone, that there's never been more opportunity to be creative and build your life, and it's the greatest era. That it is. I genuinely believe that if you've signed up and you're a part of this incredible project that I've watched from afar, whether you consciously [00:44:00] know this or it's subconscious, you're trying to choose optimism. You're trying to choose offense. You're trying to choose win. Hold on to that and don't let anybody drag you into the alternative. Life is how you see it. And so, learn the tools that will allow you to choose optimism and hope versus cynicism and fear. Ilana Golan: Bam. Mic drop. Oh my God. Gary Vee: Thank you. Ilana Golan: I can, I can literally talk to you for so many hours. Gary Vee: You're very sweet. Ilana Golan: I appreciate Gary.