Lessons from 40+ Years of Entrepreneurship | Ilana Golan

0:00This is the GaryVee Audio Experience. Gary, we chatted a little bit before we started. You were an 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, you know, a small kid, immigrant family. Yes. Why? It's almost like the reverse. It's funny when you just said why. the answer that bounced in my head is like 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.

1:03One of those two 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? It's just an instinct. There's, there was, and this is why I think, 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.

1:51this 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 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 that 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.

2:31I 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. Right. Do you think your dad's entrepreneurship was part of it? I think from a genetic standpoint, but to be honest, my father worked every minute. I don't know if I even understood, I never saw my father. It wasn't like my father was at dinner saying to me 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 a liquor store but I didn't, first of all, the word entrepreneur didn't exist.

3:18as we know. You know, he had a business. Like, 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. Right. And in retrospect, like, the more I read about him and your mom, like, the more, you know, 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. We also, timing, like we, I was born in the Soviet Union. We got out with political asylum and we were able to come to the U.S.

4:02in 78. You know, 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 hood of Queens at a time where people can't get gas right you know so it was a rude awakening um but the promise was true which was no the streets were not paved with gold but the American dream is 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.

4:48And 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 yeah, I mean, I got very fortunate. I won the parenting lottery. You know, 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 very easy for me to stay humble because when I hear them, I don't think that I did it.

5:34I think I'm the byproduct of Sasha and Tamara Vaynerchuk and that makes me happy. And it's amazing because also in your books you give um you you tell us to write your dad and that's that that's going to happen yes um because I wanted him to tell tell him about this meeting with you um but how do you um make people hungry when today they have everything so how do you so one of my favorite sayings is and this is huge for parents I have two children a lot of us that are probably watching this or some of us, I'm not gonna say a lot, but 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.

6:19One 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. Right and I love that quote I even wrote it down yeah. And I believe in it and what it's meant to say to my friends my new friends that are watching right now are listening is look you can't fake environment. If you live in a bougie neighborhood and you fly private like like your kids are living in that environment you can't be You're like, well, you should be more hungry.

7:01Well, that's hard. That's hard. So, you know, 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. You know, like, 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. The last 10, 15 years of my life, I've been around extreme wealth. And I can sit here, whether one wants to 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.

7:55I 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 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.

8:40Right. But I want my kids to be passionate. Happy, yes, of course. Fulfilled. Fulfilled, joyous, passionate. Like, if you get up in the morning and you're fired up, whether you make 40K, hey, 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, making 100K in New York City, you can't even live a lifestyle. I'm like, leave New York City. Do you like that? I love accountability. Accountability is my addiction. if you can't I don't know like I was just in Montana like 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 India or whatever yeah there's that yes but I'm actually going to go somewhere else it's 2025 right now people can have remote jobs people can zoom into every meeting like and you also don't have to if you're complaining about money you also don't have to buy seven dollar cups of coffee from Starbucks three times a day right Like people don't know how to manage their money.

9:51People live above their means. I know millionaires that are broke. Because people literally, and when I say that, I say it with a slang. Like people that earn five, six, seven, eight hundred, two million a year, but they spend more. So there's money management issues. The credit card created a huge pandemic in society. I always laugh that the more you make, the more there's ways to spend it, right? I mean, it's incredible. But let me, so you somehow at age 14 joined your dad in a wine business. Liquor at the time. Shoppers Discount Liquors was the name of the store. And even sell wine at age 16, which is not even allowed to drink.

10:30Correct. Talk to us just a little bit about what is it like for you? Is that forced? Is it felt great? 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 and being my own boss. And by the way, having a couple thousand dollars, having thousands of dollars consistently when you're 14 in 1988, 89, I mean, I'm not sure I'll ever be wealthier than I was back then because when you're like, I at one point had$10 ,000 and that was like 40 billion now. 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?

11:19The store and now I have to work for two bucks an hour I thought it was five no five oh five 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 1978, it's 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, a 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.

12:01I'm carrying huge cases of alcohol, hurting my back. I mean, I had a bad back my whole life 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. The second year though, something miraculous happened. A gentleman walks in, asks for a wine. I remember like yesterday, Caymus Special Select Cabernet from Napa Valley. He said, do you have it? And I said, no, but I might be able to get it. I go, how many would you like?

12:40He said, 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 fees parked? 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 it. You know? I felt proud about that. I wanted to help. And I thought I was a good businessman already as a kid. I wanted to help my dad. I was still scared of my dad and couldn't share my ideas yet.

13:15But I didn't like what my dad sold. I actually, 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. My family had a liquor store my whole life. 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. That's incredible. And because my mom scared me so much. Nancy Reagan, drugs. I've still to this day, I've never smoked anything or done a drug in my life. Me neither. You know, so very, very much had a mother that was passionate about that subject. So it wasn't cool to me like other high school kids of selling Budweiser or, you know, Crown Royal.

13:52Like 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 going to learn everything about wine because people collect it. And I read the Wine Spectator now instead of the Beckett baseball card guide. And that 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.

14:27I didn't taste yet. and you know building my you know it's funny I'm 40 I just turned 49 in November and you know my parents are 72 and 70 so still young thank God but you know I'm not 20 anymore either and you know I'm gonna be 50 this year and so you know me too yeah well you look amazing so I'm gonna be 50 this year and you know that makes you think about stuff those are fun things to think about and I also think I'm gonna 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. Water does help, by the way. Yes, I'm aware of it. Thank you.

15:02Thank you. Sorry. I just had to say something. That's very fair. That's very fair. And, you know, I feel like I'm at halftime, you know, 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. 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 do it.

15:36So 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 probably, let me not sugarcoat it, there was levels of resentment that were real. You know, like 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. 15 years later, it's the best decision I ever made in my life. Like giving that contribution to my parents who I give credit to everything feels incredibly appropriate and I'm really glad I did it.

16:14That's incredible. And I wanna, for those who don't know the story, I think it's important to go back there for a second. Please, happy to. 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. Yes. And that's a big part of, and I mean, you rebranded it, and that's a big reason why it went from$4 million to$60 million. It's the reason. Right? So how did you realize it and what was the change? Let's talk to it for a second.

16:59Thinking 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. I love that. So I believe if I analyze my career that the word maybe that led to yeses and nos has 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.

17:41I then saw the internet in 1995 for one second I watched a kid open a lap 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 koo cooch the first time I was like what was that he's like that's the phone line like literally and I watch him 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.

18:24That 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 going to 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 because it was like that I mean there was six guys hovering over him it was that like profound everybody was in no culture this is stupid this is nerd stuff I'm going to play basketball and I was like maybe and I was not techie I still can't keyboard I will tell you that 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 but what people don't understand is when you're willing to do two here's two things I do One, I'm willing to play long.

19:35I'm willing to invest my time and learn to something I believe will be true in 10 years. So I'm investing. Two, 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 take my dress shop and put it on social. I don't like social media, but 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 worldwide, like to your point, there was like an article or two.

20:25I'd 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. Amazing. And that led me to that evening. I finally got my chance to go on the computer like three 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. Amazing. And I love that. 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 and joined Intel as one of the first, the youngest engineer ever that they hired until then.

21:08So that, it sounded so, you know, it's like amazing. But in 2006, I'll take you there for a second. Because you somehow understood the power of personal branding. Yeah. Probably about a decade before I even understood why this is even important. and I think a lot of our audience are still at the point of I'm gonna give a thousand percent to where I work and I will never build myself on the journey. And so tell me more about that. Ideology and not understanding nuance. Let me explain what I mean by why I just said that.

21:50Personal brand. When the term first started hitting the scene in 2009, 10, 11, 12, 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. Right. And being respectful and behind the scenes, there was merit. I remember in 2009, 10, 11, 12, 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.

22:31Reputation. 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 over there in the corner. The amount of emails I got in 2010 from people that literally titled, I love you.

23:10It was a wave of love in 2010, 11 for me. Here's 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, don't think of, 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.

23:46Don't look at how I communicate. Find your own way. You don't have to dress down. if you find me on the internet, I curse a lot. You can see I get excited sometimes I jump in and cut off. There's 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. Just get your ideas into the world. There's no downside. It is honestly the only insurance policy you've got. Right, and I love that you just said that because first of all, because I needed to fall really deep in order to realize that I didn't build any safety net, right?

24:25I 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 try to help people elevate themselves, at least tell your story, understand what's your zone of genius, start telling it to the world, 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. 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. 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?

25:09You're literally one video away. For this crew, everybody here is one video away posted on LinkedIn from getting so many things they dream, do you know how many people 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, I want, not bashing their company, no, no, talk, let's say they're in SaaS hardware sales, SaaS software sales, excuse me. 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 I do not understand and all of this 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 they're scared 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.

26:16The 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 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. So I love that you said that but let's go there for a second because you're absolutely right. Probably one of the biggest fears is the hate. Yeah. 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.

26:57That's right. Right. So how do you create a tougher, maybe a thicker skin or something to just let the noise go away? Unwanted, 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. A lot of parents are like, social media is bad. I'm going to take the app off the phone. Fine. Good. Allowed. I get it and I think moderation matters. Comma, if you want your child, you're not going to protect your child from real life.

27:41Like real life happens. And so 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 it. 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 473 saying that you're like you know this is why we all laugh like you know like it's why everyone's giggling behind like I don't know what else to tell you like 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 the hump.

28:32The reason I've been able to do so much and put myself out there is someone might be right. Like if, you know, 50 people are like, this is silly, Gary, that you're doing this. They might actually be right. Like, I could be wrong. I could be out of touch. I could be out of bounds. But here's the powerful word next. And? Right. So what? So what? Right. Like, everyone's a human being. Everybody makes mistakes. Like this is, 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, all right, Gary, you're in heaven.

29:10You've got one minute to sum it up. You know, I think my answer is gonna be like, it's all just one big game of eliminating fear. I believe 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 me the offense show me the smiles I can't find it and so it's just fear I mean you want to sum up Leap from my perspective watching from afar you are empowering people to chip away at their fears make decisions based on hope and dreams not fear and doubt that's it 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 is because I don't want to regret.