Do YOU Have What it Takes to Succeed?

0:00The problem is, a lot of people have struggled with failing in front of everyone. When you're not built for it and then all of a sudden you go for it and then it fails, that's failure in front of everyone. And the one reason that most people don't do entrepreneurship is they do fear failure. Attention is the number one asset. Tell me your story, how? You moved here and you immigrated here in 1978. Yes, I convinced my parents when I was three years old to immigrate from the USSR. I love your father's hat, by the way. His hat has changed. Yeah, mom and dad are in the building. Yeah, I mean, honestly, it's a very classic story.

0:39There's lots and lots and lots and lots of people on earth that have that incredible fortunate scenario to come to this remarkable country from another place. You know, for me, which I think is a little more rare, I had really exceptional parents. And so it was like this perfect storm of right place, right time, right circumstance. when I analyze my life and when I look at many others and really for the many in here, which I appreciate the comments, but I know a lot of people here don't know who I am or don't know the depths of my story. You know, really at the end of the day, I'm incredibly interested in people.

1:18You know, one thing that's just become more and more obvious to me is I like people more than most people. Like genuinely, like even wanting to go out in the cocktail hour and talk to people instead of just being in my green room. That's just who I am. That's who I was born from day one to be. And I was able to really hone it over time. I think practice matters. You know, I always, every time I say practice, I hear Allen Iverson's practice. And I understand what he was saying. But for me, it's the reverse. You know, a lot of people ask me about my entrepreneurial career. I'm 47 years old and I've been practicing for over 40 years.

1:58you know like for me it was the only thing I did I was you know I'm not sure if I'm allowed to say this in this setting but I was an atrocious student and it was because I was pot committed long before people said go all in or be passionate there was a level of self awareness there was a level of self belief there was a level of not willing to compromise there was something that was inside of me that understood who I was I just really understood it I wasn't I wasn't gonna apologize for it. I was definitely not interested in doing anything bad. I was just looking to be fully myself. And you know, I think a lot of luck with DNA, a lot of luck with circumstance, and I think it was a perfect storm.

2:44Even the era that I'm growing up in, what is very clear to me is that I have a very strong knack for understanding attention, right? I just have always understood it. Even when I was doing lemonade stands, when I was six, seven years old, back to practicing for 40 years, I was more interested in the signs and where I was gonna put the signs to get people to buy the lemonade than the lemonade, than even the money. I was more interested in the attention than the money. So, you know, look, I'm 47 years old. The explosion of the internet happened just as I was ready to go into the real world. That's just a little bit of a luck of the draw.

3:19Sure, I can decide that I would have been a good newspaper man or a radio man or a TV man if I was born two generations earlier. But in all those scenarios, there are gatekeepers. There are gatekeepers, the internet and social media. And the reason this is such a big deal and whether you think it's awesome or you think it's bad, there's so much that goes along with it. What everyone's struggling with is nobody's in control. Facebook, Instagram, TikTok, YouTube, these platforms are empty. There's no editor-in-chief. There's no head of the studio. This is not a subjective opinion. It's merit. Who's the human can put in the work, put in the message that most attracts people's attention?

4:02And we judge. We judge in this room and the world who people pay attention to, but that's silly. You know, that's you judging clear data that supports that other people find XYZ interesting. We all have different interests. We all think different things are interesting. So, you know, I think the story of me is I'm very fortunate. And that's why I'm incredibly driven by gratitude. You know, I'm a very simple dude who's doing a lot, right? I think when people look at me from the outside, I have 700 trillion businesses. I'm putting out content 58 times a day. I'm always up to something. But in reality, I think I'm incredibly simple, which is I keep life very basic.

4:48I'm not doing it for the accolades or the trophies. You know, I'm humbled by it. I'm humbled to take a selfie, but it's not what I strive for. I don't need that. My parents took care of my self-esteem, so I'm good. I'm just living my life, and at this point, I'm just trying to, you know, there's even a part of, there's probably a level of guilt that is a currency inside of me that it worked so well for me, that that mix between gratitude and guilt inspires me very heavily to try to give an ounce to the world what's inside of me. And so that's how I roll. Trying to get a sense of a little Gary, right?

5:31Little Gary, eight, nine, 10 years old. You know, you had an entrepreneurial spirit from a very young age. You started eliminating that. But what, and then going into high school, what stereotype bucket did you fit in? Or maybe not. Were you the jock? Were you the nerd? Were you the brainiac? Were you the Romeo? Were you the... I don't know. Tell me. Paint that picture for us a little more. I think, you know, this now makes sense to me when I'm older. I think I have unusual outcome because I think it was a little bit interesting. Like, you know, right around fourth or fifth grade from the jock standpoint was when I transitioned from wanting to be on the New York Jets to thinking about buying them.

6:19So up first, that was about 10, 11, about 12, because, you know, seven, eight, nine, I have such remarkable hand-eye coordination that I was able to dominate first and second grade, but somewhere around fourth and fifth grade, things changed a little bit. You had to actually be strong and fast and athletic and all these other things. I'm like, uh-oh, this might be a problem. I was really a bad student. Like, you know, by fourth grade, I know mom, I had to actually ask my high school to send me the report card because my mom changed the story in her mom, in her mind, and decided I was a C student.

6:56But by fourth and fifth grade, I started getting a lot of D's and F's. And that was actually extremely challenging. You know, I had a lot of teachers and a lot of my friends' parents really communicate to me in an incredibly negative way because of my grades, right? Like I remember, you know, for the people over 45, you might remember this, for the kids, this might be a reference that doesn't land, but for some reason in the late 80s, early 90s, the way they tried to scare you, and I feel terrible for people in the sanitation business, but the amount of teachers that told me I was gonna end up being a garbage man was like staggering.

7:35It was like an everyday barrage. But for me, this is why I love entrepreneurship. There were, you know, sports started to tell me I wasn't good enough, right? And that was a very early first, second grade dream. My teachers were definitely telling me that I wasn't good enough. That started bleeding into my friends' parents having comments and snarky comments. But the two places that always told me I was good enough was home and business, right? When I started selling baseball cards in sixth grade, I was the best at it. I was the best at business. So the reason I love the market and the world is the world's always been good to me.

8:22It's always told me that I was good. And so I think a lot about positive affirmation. I think a lot about the parents in this room that have kids. And I think a lot about what do they tell their kids? Meaning, what are they cheering for? For me, that's a very interesting game. I struggle with cheering for things that are very transactional. You know, I fear that. I fear that it makes our kids robotic and it makes them every 90 days and it makes them robots. And I think we struggle as a society to understand creativity, to understand different. And I got very fortunate, I think. And I'll tell you another thing.

9:06what I really think my mom drilled, which is a super challenge, because I'll be honest with you, I'm not great at it as a parent, was she made me not think my grades were a reflection of who I was going to become. But she held me accountable for having bad grades. To find the balance of making me believe that these bad grades would not define me, but also grounding me every three months when my report card came home is a very fine tightrope that I think every parent here can understand is almost impossible. Like I really struggle to see it because I think we go too far in any direction and so, you know, to answer you directly, little Gary by fourth grade understood he was going to win the world.

9:56Nobody was going to stop him and he lived in his own cocoon. I lived in my own head. And so your parents were entrepreneurs or they were small business owners. at what age would you say you really understood the word entrepreneurship? I mean entrepreneurship wasn't a word. Like when did I realize entrepreneurship? I don't know, 2006? Like the word was businessman. There was no entrepreneurship. As a matter of fact, and this will land with people over 40, the only times I heard the word entrepreneur by the time I was 35 was I'd heard it randomly and it usually meant the person was a loser. It meant that they were making pretend to be a business.

10:39I remember business man was here, and entrepreneur was here, and usually thought it was someone using mommy and daddy's money to make pretend, it's actually now become that again.

10:52But when I was growing up, I mean you rarely say, I actually think Entrepreneur Magazine might have been the first time I even, going on a wine trip, I grew up in my dad's business, in the wine business. I actually remember maybe going to Napa in my early 20s and seeing Entrepreneur Magazine on the shelf, and I was like, it was just, I just thought I was a businessman. And so, and you have to understand, again, there's no entrepreneur when all the kids we just talked to, when I was their age, there was no businessman that you put on a pedestal. It's now popular culture. It's now cool. There was nothing cool about businessmen.

11:29When I, like, the most, like, entrepreneurial or most successful businessman, when I was like in high school was the fucking biggest nerd on earth. There was nothing you were aspiring to. It was like, you thought, you know, like it was just not this way. Today, it's, you know, and I think about this a lot. I think people don't, you know, the one class I was solid at and not got F's in was history. And I think about, I use history a lot as a frame of reference for the future. So, you know, 70 years ago, 60 years ago, a pilot and an astronaut was super famous in America. Like astronauts off the charts and pilots were like, whoa, like athletes.

12:12In the 1950s, professional athletes took summer jobs or off-season jobs because they didn't get paid enough. Literally Yankees that won World Series would then go work in hardware stores in Hoboken because they were getting paid so little or less in comparison and now they get paid$70 million a year and so I think, you know, I think things change and I think the entrepreneur really hit fever pitch three, four, five years ago and I think about that a lot because I'm worried about that to be honest. How so? Well, I think if you think entrepreneurship is cool like being a rapper or a rock star or like the cool stuff, well then you try to become one which is amazing.

12:58The problem is entrepreneurship is not like school. Entrepreneurship is not like your parents. Entrepreneurship doesn't care about your feelings. Entrepreneurship is not fake. Entrepreneurship is not something you can easily figure out and the results you can't hide. When you get a bad grade, you can blame the teacher. Right, you can do stuff. When you work in government, like it's a machine. In corporate America, machine, you can hide. There's a reason sayings like success has a million fathers, failure has none, exist. There are many, many, many, many fake environments in the world. But sports, you can't fake.

13:41Last night the Jets played, they lost. They almost won. They almost won. They did all right. They did all right. Another game that happened to happen yesterday was the Dolphins got their face beaten. Sports, you know, can't, the Dolphins can't wake up today and be like, oh, we did it. But you can do that in corporate. You can do that. it's fake in a lot of places on earth. Sports is not fake. The closest thing to sports is entrepreneurship. Your business either works or it doesn't. You either make money or you don't. It either stays alive or it goes out of business. And what I worry about is a lot of people who are not actual entrepreneurs, who are playing entrepreneur or not purebred, I want everyone to be an entrepreneur if they are one, but for a lot of people they're a number two, they're a number four, they're a number eight, and that's amazing.

14:30Some people are a stay-at-home dad. Some people are a lawyer. We need everything and that's amazing. I don't want people to be entrepreneurs. I want people to be self-aware to figure out what makes them happy and live that life. When we made entrepreneurship so cool, a lot of people went for it. The problem is a lot of people have struggled with failing in front of everyone. When you're not built for it and then all of a sudden you go for it and then it fails, that's failure in front of everyone. And the one reason that most people don't do entrepreneurship is they do fear failure. And I think a lot about fear and failure.

15:08I think one of the great things that happened to me was I did love sports, which meant I lost a lot. And then with school, I was losing so much in fourth, fifth, sixth, seventh grade, that by the time I was 14, I was used to losing. I would argue I loved losing. I think it's why I love being a Jets fan. I'm being serious. I'm being serious. As pissed as I was last night, there is a secret percentage of me that was like, good, good. You know, like, you know, and I think that is a characteristic of an entrepreneur and that was a huge characteristic of mine. I think a lot about the kids that I see now that run away from playing something because they're scared to lose.

15:51For me, I was the reverse. I would play and play and play. I would cry. I cried a lot. When I was a kid, if you want to know about me, I cried a lot at nine, 10, 11, 12, but I would just get up again and play and get up again and play. And I think we've done a terrible job in our society on demonizing losing. When we give kids eighth place trophies, we confuse them. You understand? We start to tell them as parents, losing is bad, so we have, because they know, I promise all the parents in here, when your kid's eight and they get an eighth place trophy, they know it's weird. And when we give them that trophy, we're telling them losing is so bad, we need to like coddle your feelings and we're gonna give you this bullshit trophy.

16:37And what ends up happening is it doesn't set them up for real life because real life happens and it doesn't work that way. Before we go to the room, I wanna ask you one question about failing. What's your biggest professional fail? I could take the next, I passed on, you heard that I invested in Uber? In the second round. I passed on Uber twice. And I wrote, my first book I wrote was called Crush It. I acknowledge only my family and one random person, the founder of Uber, Travis, because he helped when I wrote the book. He was the person I sent it to and he gave me great feedback and I wanted to acknowledge him.

17:14We were real friends' friends. And I keep a very small circle. I have a lot of acquaintances, but friends, small. He pitched it to me twice. twice, the first time I passed, the second time, he picked, I mean, it was in this like grove in San Francisco, I think I stopped going to San Francisco because I didn't want to drive by it. He pitched me emphatically, like hey, I really want you in, and it's funny, it goes back to offense versus defense. I just bought my first meaningful apartment in Manhattan, and I was a little less cash rich than I was accustomed to, and I just didn't feel like I wanted to write that$25 ,000 or$50 ,000 check, which I could have.

17:56That$25 ,000 to$50 ,000 check, I left$400 million on the table. All right. That is a fail. However, it's not a fail, fail, fail. Well, I don't know how to fail, fail, fail because my parents taught me how to save money. Okay. I don't bet the farm to go to zero. You know, my failures are things I've left on the table. My failures are the things I didn't do. When Steven Ross, the owner of the Miami Dolphins, bought a piece of VaynerMedia, he offered us, me and my brother, instead of cash, he offered a piece of the Miami Dolphins. I, out of pure emotion, because it was a good business deal, because I hate the Dolphins with my entire heart, passed on that.

18:49instead of the$25 million in cash that we got to put into a fund and a couple, maybe 10 more million in cash for me and AJ to split to take home, that 35 is probably 350 million. So I don't know, I've told you two stories that I've already left$700 million on the table. I mean, I can go on. I mean, this is the life of an entrepreneur. Like, honestly, I know what those numbers, I mean, honestly, I'm saying it out loud. I'm like, what the fuck? But like, you know, like, I understand what it sounds like, but the reality is, is like, I'm not doing it for the money. I think that's the biggest reason we have so many fake entrepreneurs.

19:28I think the majority of them are doing it for the money. I think most people go into entrepreneurship or business to buy things that the business allowed them to buy. I just want to build businesses. I just want to play my game. And so I've made a ton of mistakes. But the one that I most regret is the one I've been most working on. I really struggled with candor in my professional career, which is wild because as a public figure and as a personality, when I'm talking to the world, candor is my strength. But when I spoke to people individually that worked for me or that I cared about, I struggled with it.

20:05Because if I like you, telling you the truth that you're not doing well at something was a real struggle for me. And by the way, authentically, still is. But I've worked on it a lot the last four or five years and I think it's really impacted my business in a very positive way. The thing I most regret are the people that I fired along the way who really weren't good at their jobs but I never set them up to fix it because I couldn't tell them the truth and then I would surprise them and just fire them. And it's a huge regret and by far the biggest mistake of my career and I'm proud that I'm working on it.

20:38Okay.

20:44So we're gonna pivot a little bit I've been talking about parenting, and I've seen a lot of your content on Instagram, and I've never heard, we have some questions that I've probably never heard. So, you spoke about micro-adversities, and how some of those micro-adversities really contributed to you, so it's not a success now. You talked a little bit about some of the struggles that you've had, and I'm sure all that filled your emotional fortitude to handle the feeling. There are a lot of immigrants here in this room, and there are a lot of people who came to this country who made it big, and Malcolm Bible talks about this too.

21:13they're not able to recreate those same conditions. Like you're not gonna have your daughter in a studio with eight people having to relive some of what you did. You can't fake environment. So I think the big question that a lot of people here are interested in is how do you build that same strength? How do you build that same entrepreneurial drive? You don't. What hope is there? None. Look, it's hard to be hungry when you're fed.

21:43You know, and so in a room of a lot of immigrants who made it, like, is anyone confused? Like, you're living it. You know. There's a reason it works the way it does. And I also challenge all of us parents who've lived that journey that we shouldn't idolize how we did it and that shouldn't be imposed on our children. We should maybe idolize, you know, things that we like about our kindness, who we are as human beings, but we're not gonna be able to replicate the environment. I mean, I sit on the board of Pencils of Promise and Charity Water. We do a ton of work in Africa to build schools where there are no schools to get clean water.

22:25By the way, you wanna be grateful real fast? There are 750 million people on earth, almost 10 % that do not have access to clean water. We worry about dumb, silly things. Like our internet's slow, right? Or like silly things and there's 10 % of our society doesn't have access to clean water. Think about that. So I sit on these boards. I have all my wealthy friends, many who came up the way I did with less than more. And they're like, Gary, can you take my 15-year-old son to Africa for a week? I want to really show them. I'm like, okay. But like, just to save you some time, they're not going to come back and be totally different people.

23:07Like, you know, we try to do all these silly tactics we're not gonna win that game. I think what we can do, I think we need to focus on civility and humanity and good traits. One thing we do very poorly is we create ideology that can't be accomplished. It is the human spirit. We need to get off the religious bandwagon of that, you can recreate it, you can't. Right? You can control it, you can mitigate it. Money is a big one. you know I have you know I talk to my parents about my situation and I'm always like well there's gonna be an age where I stop giving it to them and like I look at their eyes and I walk away and I know they're laughing at me because they think it's already too late at 14 and I think oh no that's the right time and you know you go by stories I have unlimited friends who came up in very wealthy environments whose parents made them get jobs and stopped giving them money around 14, 15, 16 and when I analyzed them versus friends who didn't in over 40, 50 people, it feels a little bit better.

24:10But we're not gonna be able, you know, my kids are not gonna work in my dad's liquor store for 15 hours a day from 15 years old on, seven days a week for 20 years. That's not happening. And that's okay. It allows me to make fun of them that they're soft.

24:32So, I think you highlighted some of this, but talk to us a little bit about this hustle mindset, this working hard, grinding through the knife, but yet maintaining integrity and really emphasizing character. Well, that's where we screw up words. It's funny even that you asked that. I'll explain what I mean by that. The reason you asked that is we manipulate words. You know, when I was growing up, hustle meant hard work because Pete Rose was Charlie Hustle and he worked hard and that was a good word. Then to your point, somewhere in the last five to 10 years, the word hustle kind of got conformed into, and I know that the word hustle is like I hustled him, so there was a negative connotation, but to me, when you just asked that question, I laughed.

25:16Why would work ethic compromise honor? Those are the two easiest things to balance on Earth. So I think that just comes down to how we interpret words. I used hustle as a public figure from 2006 to 2014 aggressively. It communicated what I believed, which is there's a lot of things all of us cannot control. But one thing we can all control is how much effort we put into things. It's the most controllable thing. But then the word got manipulated and started to mean burnout or win at all costs or money over everything. And so I walked away from that word. I mean, my usage of that word is so low now.

26:00I just use work ethic. It allows me to explain the same thing. and I'm not emotionally attached to any words, but being able to balance work ethic with doing the right thing is the only thing I believe in. Very nice. So the last. I'll give you one to build on if I may. The guy. I think one thing, I'm sorry to jump in, but that really inspired me. There's another thing I think a lot about. So how many people here by show of hands consume some of my content or have a good gist of my content? Raise your hands. Thank you. So for the people that raised their hands, for the other people that didn't, one of my favorite things to talk about is patience.