Gary Vaynerchuk
Appearances
Leap Academy with Ilana Golan
GaryVee: From Earning $2 an Hour to Running a $350M Digital Empire
Entrepreneurship or running a company is a series of micro headaches and problems and anxieties. Me, I'm addicted to eating that crap.
Leap Academy with Ilana Golan
GaryVee: From Earning $2 an Hour to Running a $350M Digital Empire
It's the reason.
Leap Academy with Ilana Golan
GaryVee: From Earning $2 an Hour to Running a $350M Digital Empire
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 nos has been foundational for me.
Leap Academy with Ilana Golan
GaryVee: From Earning $2 an Hour to Running a $350M Digital Empire
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.
Leap Academy with Ilana Golan
GaryVee: From Earning $2 an Hour to Running a $350M Digital Empire
I watched a kid open a, now we're into the laptop era, so it was cool, or maybe it was desktop. Anyway, a kid goes on the internet, I heard cuckooch the 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,
Leap Academy with Ilana Golan
GaryVee: From Earning $2 an Hour to Running a $350M Digital Empire
that this was going to change my life. Up until five minutes earlier, I always dreamed that I was gonna go help my dad and I was gonna open up the Toys R Us of wine stores, that I was gonna have 100 locations in the country. Within a moment's notice, I said, I'm gonna build this .com thing. I'm gonna build a store inside the computer.
Leap Academy with Ilana Golan
GaryVee: From Earning $2 an Hour to Running a $350M Digital Empire
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.
Leap Academy with Ilana Golan
GaryVee: From Earning $2 an Hour to Running a $350M Digital Empire
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.
Leap Academy with Ilana Golan
GaryVee: From Earning $2 an Hour to Running a $350M Digital Empire
But 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. 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.
Leap Academy with Ilana Golan
GaryVee: From Earning $2 an Hour to Running a $350M Digital Empire
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.
Leap Academy with Ilana Golan
GaryVee: From Earning $2 an Hour to Running a $350M Digital Empire
I had heard about the worldwide, 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.
Leap Academy with Ilana Golan
GaryVee: From Earning $2 an Hour to Running a $350M Digital Empire
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.
Leap Academy with Ilana Golan
GaryVee: From Earning $2 an Hour to Running a $350M Digital Empire
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, 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. And being respectful and behind the scenes, there was merit.
Leap Academy with Ilana Golan
GaryVee: From Earning $2 an Hour to Running a $350M Digital Empire
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. Reputation. Completely melted the anger.
Leap Academy with Ilana Golan
GaryVee: From Earning $2 an Hour to Running a $350M Digital Empire
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.
Leap Academy with Ilana Golan
GaryVee: From Earning $2 an Hour to Running a $350M Digital Empire
The amount of people that built their personal brands in 2008 after I wrote Crush It, that book all there in the corner.
Leap Academy with Ilana Golan
GaryVee: From Earning $2 an Hour to Running a $350M Digital Empire
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 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.
Leap Academy with Ilana Golan
GaryVee: From Earning $2 an Hour to Running a $350M Digital Empire
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.
Leap Academy with Ilana Golan
GaryVee: From Earning $2 an Hour to Running a $350M Digital Empire
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?
Leap Academy with Ilana Golan
GaryVee: From Earning $2 an Hour to Running a $350M Digital Empire
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. It is honestly the only insurance policy you've got.
Leap Academy with Ilana Golan
GaryVee: From Earning $2 an Hour to Running a $350M Digital Empire
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.
Leap Academy with Ilana Golan
GaryVee: From Earning $2 an Hour to Running a $350M Digital Empire
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? You are literally one video away.
Leap Academy with Ilana Golan
GaryVee: From Earning $2 an Hour to Running a $350M Digital Empire
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. Not bashing their company.
Leap Academy with Ilana Golan
GaryVee: From Earning $2 an Hour to Running a $350M Digital Empire
No, no, let's say they're in 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 DM him and say, do you want a job?
Leap Academy with Ilana Golan
GaryVee: From Earning $2 an Hour to Running a $350M Digital Empire
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.
Leap Academy with Ilana Golan
GaryVee: From Earning $2 an Hour to Running a $350M Digital Empire
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 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.
Leap Academy with Ilana Golan
GaryVee: From Earning $2 an Hour to Running a $350M Digital Empire
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 days, I was ringing doorbells, shoveling snow.
Leap Academy with Ilana Golan
GaryVee: From Earning $2 an Hour to Running a $350M Digital Empire
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 gonna 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.
Leap Academy with Ilana Golan
GaryVee: From Earning $2 an Hour to Running a $350M Digital Empire
You know, a lot of parents are like, social media's bad, I'm gonna take the app off the phone. Fine. 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 it.
Leap Academy with Ilana Golan
GaryVee: From Earning $2 an Hour to Running a $350M Digital Empire
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. You know, it's why everyone's giggling behind the camera.
Leap Academy with Ilana Golan
GaryVee: From Earning $2 an Hour to Running a $350M Digital Empire
I don't know what else to tell you. I believe, and 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 eight billion people need to get over the hump. The reason I've been able to do so much and put myself out there is someone might be right.
Leap Academy with Ilana Golan
GaryVee: From Earning $2 an Hour to Running a $350M Digital Empire
You know, 50 people are 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.
Leap Academy with Ilana Golan
GaryVee: From Earning $2 an Hour to Running a $350M Digital Empire
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. 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?
Leap Academy with Ilana Golan
GaryVee: From Earning $2 an Hour to Running a $350M Digital Empire
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.
Leap Academy with Ilana Golan
GaryVee: From Earning $2 an Hour to Running a $350M Digital Empire
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 are empowering people to chip away at their fears.
Leap Academy with Ilana Golan
GaryVee: From Earning $2 an Hour to Running a $350M Digital Empire
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. I'd rather die on my own sword than someone else's.
Leap Academy with Ilana Golan
GaryVee: From Earning $2 an Hour to Running a $350M Digital Empire
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 whatever it is. Die on your own sword.
Leap Academy with Ilana Golan
GaryVee: From Earning $2 an Hour to Running a $350M Digital Empire
And now they're in blame. Listen, if you're a blamer or a complainer, I can give you a direct correlation. I know what you're going to say. 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.
Leap Academy with Ilana Golan
GaryVee: From Earning $2 an Hour to Running a $350M Digital Empire
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?
Leap Academy with Ilana Golan
GaryVee: From Earning $2 an Hour to Running a $350M Digital Empire
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. Please audit your circle and pay attention to who listens because I promise you, let me tell you who's not around.
Leap Academy with Ilana Golan
GaryVee: From Earning $2 an Hour to Running a $350M Digital Empire
friends and acquaintances and coworkers that you used to have who are positive and on the offense, and they've weaned you out.
Leap Academy with Ilana Golan
GaryVee: From Earning $2 an Hour to Running a $350M Digital Empire
This goes back to New York City. Let's talk about America. We just had an election. You know, it's been very, Israel, like the world is very contentious. But I say this all the time. I'm 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.
Leap Academy with Ilana Golan
GaryVee: From Earning $2 an Hour to Running a $350M Digital Empire
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 news. 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.
Leap Academy with Ilana Golan
GaryVee: From Earning $2 an Hour to Running a $350M Digital Empire
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.
Leap Academy with Ilana Golan
GaryVee: From Earning $2 an Hour to Running a $350M Digital Empire
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.
Leap Academy with Ilana Golan
GaryVee: From Earning $2 an Hour to Running a $350M Digital Empire
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 overnight success. I'm gonna say very real truth.
Leap Academy with Ilana Golan
GaryVee: From Earning $2 an Hour to Running a $350M Digital Empire
I would argue that entrepreneurship or running a company is 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 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.
Leap Academy with Ilana Golan
GaryVee: From Earning $2 an Hour to Running a $350M Digital Empire
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. 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.
Leap Academy with Ilana Golan
GaryVee: From Earning $2 an Hour to Running a $350M Digital Empire
When you become a parent, something weird happens where you realize, wait a minute, this little thing, this kid, I'm responsible. I'm the last line of defense.
Leap Academy with Ilana Golan
GaryVee: From Earning $2 an Hour to Running a $350M Digital Empire
for the over 2,000 employees I have globally, when there's a leak in the roof in Thailand, and this is real stuff I'm not talking about, of course there's people that handle that, but if it gets, the fires in LA, 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.
Leap Academy with Ilana Golan
GaryVee: From Earning $2 an Hour to Running a $350M Digital Empire
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.
Leap Academy with Ilana Golan
GaryVee: From Earning $2 an Hour to Running a $350M Digital Empire
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 report card number one time because I knew I was walking into a firing squad. I was going to be punted. This is like clockwork.
Leap Academy with Ilana Golan
GaryVee: From Earning $2 an Hour to Running a $350M Digital Empire
I don't know what I'm doing.
Leap Academy with Ilana Golan
GaryVee: From Earning $2 an Hour to Running a $350M Digital Empire
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, I feel I was very capable of doing.
Leap Academy with Ilana Golan
GaryVee: From Earning $2 an Hour to Running a $350M Digital Empire
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.
Leap Academy with Ilana Golan
GaryVee: From Earning $2 an Hour to Running a $350M Digital Empire
�, �, �, �, �, �, �, �, �, �,GGGGGGGGGGGG�, M. M. M. M. M. Thank you.
Leap Academy with Ilana Golan
GaryVee: From Earning $2 an Hour to Running a $350M Digital Empire
I think from a genetic standpoint, but 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.
Leap Academy with Ilana Golan
GaryVee: From Earning $2 an Hour to Running a $350M Digital Empire
entrepreneurship was my life. Me getting in front of a camera at 30 years old, me taking my life savings and investing it in Facebook and Twitter, me buying Bitcoin in 2014, 15.
Leap Academy with Ilana Golan
GaryVee: From Earning $2 an Hour to Running a $350M Digital Empire
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. First of all, the word entrepreneur didn't exist, 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.
Leap Academy with Ilana Golan
GaryVee: From Earning $2 an Hour to Running a $350M Digital Empire
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.
Leap Academy with Ilana Golan
GaryVee: From Earning $2 an Hour to Running a $350M Digital Empire
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, we land in America. My parents here in Russia, the Soviet Union, that America, the streets are paved with gold.
Leap Academy with Ilana Golan
GaryVee: From Earning $2 an Hour to Running a $350M Digital Empire
Well, we go to the 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,
Leap Academy with Ilana Golan
GaryVee: From Earning $2 an Hour to Running a $350M Digital Empire
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.
Leap Academy with Ilana Golan
GaryVee: From Earning $2 an Hour to Running a $350M Digital Empire
The reason I've been able to do so much and put myself out there is 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. High school is over. Getting made fun of cannot stop you from building your life
Leap Academy with Ilana Golan
GaryVee: From Earning $2 an Hour to Running a $350M Digital Empire
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 words 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. I think I'm the byproduct of Sasha and Tamara Vaynerchuk and that makes me happy.
Leap Academy with Ilana Golan
GaryVee: From Earning $2 an Hour to Running a $350M Digital Empire
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.
Leap Academy with Ilana Golan
GaryVee: From Earning $2 an Hour to Running a $350M Digital Empire
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.
Leap Academy with Ilana Golan
GaryVee: From Earning $2 an Hour to Running a $350M Digital Empire
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, that's hard. So I think there's a couple things to think about.
Leap Academy with Ilana Golan
GaryVee: From Earning $2 an Hour to Running a $350M Digital Empire
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 gonna 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.
Leap Academy with Ilana Golan
GaryVee: From Earning $2 an Hour to Running a $350M Digital Empire
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.
Leap Academy with Ilana Golan
GaryVee: From Earning $2 an Hour to Running a $350M Digital Empire
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 are borderline suicidal, are drug addicts, are deeply depressed, are anxious.
Leap Academy with Ilana Golan
GaryVee: From Earning $2 an Hour to Running a $350M Digital Empire
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.
Leap Academy with Ilana Golan
GaryVee: From Earning $2 an Hour to Running a $350M Digital Empire
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.
Leap Academy with Ilana Golan
GaryVee: From Earning $2 an Hour to Running a $350M Digital Empire
I love when everyone's like, you know, making 100K in New York City, you can't even live a lifestyle. I'm like, leave New York City. Do you like that? 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?
Leap Academy with Ilana Golan
GaryVee: From Earning $2 an Hour to Running a $350M Digital Empire
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 cups of coffee from Starbucks three times a day. Right. Like people don't know how to manage their money. People live above their means. I know millionaires that are broke.
Leap Academy with Ilana Golan
GaryVee: From Earning $2 an Hour to Running a $350M Digital Empire
People that earn five, six, seven, 800, 2 million a year, but they spend more. So there's money management issues. The credit card created a huge pandemic.
Leap Academy with Ilana Golan
GaryVee: From Earning $2 an Hour to Running a $350M Digital Empire
Liquor at the time. Shoppers Discount Liquors was the name of the store.
Leap Academy with Ilana Golan
GaryVee: From Earning $2 an Hour to Running a $350M Digital Empire
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 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 because I at one point had $10,000 and that was like 40 billion now.
Leap Academy with Ilana Golan
GaryVee: From Earning $2 an Hour to Running a $350M Digital Empire
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 I thought it was five. No, 505 was minimum wage. My dad paid me under the table cash, two bucks an hour.
Leap Academy with Ilana Golan
GaryVee: From Earning $2 an Hour to Running a $350M Digital Empire
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, a couple months in or a year in, I'm allowed to stock the shelves. That was my promotion.
Leap Academy with Ilana Golan
GaryVee: From Earning $2 an Hour to Running a $350M Digital Empire
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 because of this. Stocking shelves for 12 hours a day, back to before we started filming, lunch, water. Yeah. Didn't eat lunch. It was immigrant 101. Son of a merchant. 1930s Brooklyn life. That's what I was living.
Leap Academy with Ilana Golan
GaryVee: From Earning $2 an Hour to Running a $350M Digital Empire
And the first year, I hated it. The second year, though, something miraculous happened. A gentleman walks in, asks for a wine. I remember it like yesterday. Caymus 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.
Leap Academy with Ilana Golan
GaryVee: From Earning $2 an Hour to Running a $350M Digital Empire
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 part? Yeah. 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.
Leap Academy with Ilana Golan
GaryVee: From Earning $2 an Hour to Running a $350M Digital Empire
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. 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. My family had a liquor store my whole life.
Leap Academy with Ilana Golan
GaryVee: From Earning $2 an Hour to Running a $350M Digital Empire
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. I still to this day have never smoked anything or done a drug in my life. So very, very much had a mother that was passionate about that subject.
Leap Academy with Ilana Golan
GaryVee: From Earning $2 an Hour to Running a $350M Digital Empire
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.
Leap Academy with Ilana Golan
GaryVee: From Earning $2 an Hour to Running a $350M Digital Empire
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. I didn't taste yet.
Leap Academy with Ilana Golan
GaryVee: From Earning $2 an Hour to Running a $350M Digital Empire
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 I'm gonna be 50 this year. 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 important to me. And I believe in it and I live my life based on that will be true.
Leap Academy with Ilana Golan
GaryVee: From Earning $2 an Hour to Running a $350M Digital Empire
And 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.
Leap Academy with Ilana Golan
GaryVee: From Earning $2 an Hour to Running a $350M Digital Empire
Just to give the punchline to everybody who doesn't know, I built my dad's business from four 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. 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.
Leap Academy with Ilana Golan
GaryVee: From Earning $2 an Hour to Running a $350M Digital Empire
I'm so happy to be a part of this.
Leap Academy with Ilana Golan
GaryVee: From Earning $2 an Hour to Running a $350M Digital Empire
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. 15 years later, it's the best decision I ever made in my life. Giving that contribution to my parents, who I give credit to everything, feels incredibly appropriate.
Leap Academy with Ilana Golan
GaryVee: From Earning $2 an Hour to Running a $350M Digital Empire
And I'm really glad I did it.
Young and Profiting (YAP) with Hala Taha
Unlock Your Potential and Thrive as a Content Creator | Presented by OpusClip | YAPCreator
It's the first time we can. You know, because for the first time ever, the creative is the variable of the reach. And that's marketing jargon, so let me say it again. For the first time ever, how good your picture or video is can lead to millions of people seeing it that never existed before. In the history of time, you'd have to be on television.
Young and Profiting (YAP) with Hala Taha
Unlock Your Potential and Thrive as a Content Creator | Presented by OpusClip | YAPCreator
We're on the biggest magazine or newspaper to ever get a million people in America or the world to know anything. And you'd have to spend millions of dollars for that. Now, every day, we all know, every day that happens to somebody. Now, what we've also learned is just because you go viral once doesn't mean you're going to be a billionaire.
Young and Profiting (YAP) with Hala Taha
Unlock Your Potential and Thrive as a Content Creator | Presented by OpusClip | YAPCreator
It usually means that you're going to have this moment that you refer to your whole life and you're actually going to be sad six months later because you weren't able to capitalize it. That goes into being a real entrepreneur. But for the first time ever, entrepreneurs, you have a fighting chance. Ember Chamberlain's coffee can compete with Folgers. Charlie D'Amelio's popcorn can compete.
Young and Profiting (YAP) with Hala Taha
Unlock Your Potential and Thrive as a Content Creator | Presented by OpusClip | YAPCreator
Logan Paul and KSI's energy drink is really competing. Mr. Beast's chocolate is really competing. And they're the preview, not the anomaly. I started a wine brand and sold it to Constellation for tens and tens of millions of dollars because I made organic content on the internet about wine and then started a wine brand. That will be a very normal occurrence for a long time.
Young and Profiting (YAP) with Hala Taha
Turn Your Followers Into Superfans With Trust and Authenticity | Presented by OpusClip | YAPCreator
When I make content, sometimes I'm like, this piece of content that I'm going to make is going to hit 45 to 55-year-old first-time moms everywhere. on the coasts. More New York, LA mentality than London, than Ohio, than Spain. So if I know that I'm doing that, don't you think that my adjectives and analogies tone intent, right? So I want everyone who's listening to start thinking about cohorts.
Young and Profiting (YAP) with Hala Taha
Turn Your Followers Into Superfans With Trust and Authenticity | Presented by OpusClip | YAPCreator
Gary, what do you mean? I just do sneaker content. Okay. Well, there's a lot of different niches within sneaker content. There's people of high net worth like myself who can afford bougie fucking Nike Air Force One collaborations. There's other people who just really like New Balance. There's the Reebok movement that I'm getting into as well. There's a lot going on.
Young and Profiting (YAP) with Hala Taha
Turn Your Followers Into Superfans With Trust and Authenticity | Presented by OpusClip | YAPCreator
Crocs, if you want to expand it a little bit. Do you know who you're making this video for? Because everyone's going to Vanilla. I make content for entrepreneurs. I'm like, okay, knock yourself out. Imagine how much better a piece of content is that you know that you're going to make.
Young and Profiting (YAP) with Hala Taha
Turn Your Followers Into Superfans With Trust and Authenticity | Presented by OpusClip | YAPCreator
I'm going to make content for first-generation Hispanic entrepreneurs that are 18 to 22 that came from immigrant parents that came from Mexico. I'm going to use analogies. I'm going to make reference to rigatón. I'm going to talk about San Antonio culture.
Young and Profiting (YAP) with Hala Taha
Turn Your Followers Into Superfans With Trust and Authenticity | Presented by OpusClip | YAPCreator
It's called relevance, everyone. If you're not relevant to someone, the second I make a long-tail barstool joke, every barstool dude is like, fuck, yeah. Like, it's not super complicated. And so, because everyone gets so boring and vanilla right away. People say to me all the time, they're like, it's a really funny thing that I fuck people up with.
Young and Profiting (YAP) with Hala Taha
Turn Your Followers Into Superfans With Trust and Authenticity | Presented by OpusClip | YAPCreator
Like, because I've been so consistent and growing and all this stuff. But then, like, sometimes they'll be like, but Gary, you say the same shit. I'm like, what do you want me to make up stuff I don't believe in? Mm-hmm.
Young and Profiting (YAP) with Hala Taha
Turn Your Followers Into Superfans With Trust and Authenticity | Presented by OpusClip | YAPCreator
And then they go, like if they stick with me in that combo, they start to realize, ah, I say the same macro 15 things, but the way I say it differently and how and where and what and to whom, that's the game. So cohorts, these are consumer segmentations. In old television talk, it was, we're trying to reach the 18 to 35-year-old demo.
Young and Profiting (YAP) with Hala Taha
Turn Your Followers Into Superfans With Trust and Authenticity | Presented by OpusClip | YAPCreator
I like to think, and I know I'm looking at your crew a lot because I like doing that. I like to think everyone in here is at a point in their lives where they realize an 18-year-old person and a 32-year-old person are very different. But that was television. You didn't have the internet. Now that we have the internet, Like everybody who's listening should be posting on Facebook. It's huge.
Young and Profiting (YAP) with Hala Taha
Turn Your Followers Into Superfans With Trust and Authenticity | Presented by OpusClip | YAPCreator
Still, I'm getting 25, 30 year old audience on Facebook. Now they're on there like once in a blue moon compared to whatever. But like, like you should be relevant to Facebook audience. You should be relevant to TikTok audience. Snapchat's culture is slightly different than TikTok's. Like it's all different rooms out there and you want to be in every room.