The Diary Of A CEO with Steven Bartlett - Gary Vee’s Emotional Confession About His Success & Family!

Episode Date: December 26, 2022

If you have a social media account you’ve seen Gary Vee, but this is a version of Gary Vaynerchuk that you’ve never seen before. You probably know him as the fast talking business sage who has industry leaders and CEO’s hanging on his every word, now see him speechless. A Belarusian immigrant to America, Gary has always been driven and hungry for the next big opportunity. Using the burgeoning young internet he transformed his families wine business and fortunes and hasn’t stopped since. In this conversation Gary discusses the endless graft and struggle behind the glistening sheen of success and social media slogans, and just what it takes to become the investor that investors invest in, the entrepreneur’s entrepreneur. Gary: Instagram - https://bit.ly/3GfswJg Twitter- https://bit.ly/3VlWHCX @garyvee Follow me: https://beacons.ai/diaryofaceo

Quick one. Just wanted to say a big thank you to three people very quickly. First people I want to say thank you to is all of you that listen to the show. Never in my wildest dreams is all I can say. Never in my wildest dreams did I think I'd start a podcast in my kitchen and that it would expand all over the world as it has done. And we've now opened our first studio in America, thanks to my very helpful team led by Jack on the production side of things. So thank you to Jack and the team for building out the new American studio. And thirdly to to Amazon Music, who, when they heard that we were expanding to the United States and I'd be recording a lot more over in the States, they put a massive billboard in Times Square for the show. So thank you so much, Amazon Music. Thank you to our team. And

thank you to all of you that listened to this show. Let's continue. There's certain things that I'm not ready to talk about. Why? I just feel like... She made me happy. Gary Vaynerchuk. Gary V. Gary Vaynerchuk.

One of the world's leading marketing experts. Entrepreneur and investor. A New York Times best-selling author. And is one of the loudest voices on the internet. I've exhausted the conversation of grinding, learning how to be an entrepreneur in the streets of New Jersey. There was a kid who wrote a medium piece

about me being the face of hustle. I was on a plane, I landed, and it was just all this chaos. And there was a lot of things that weren't true. There were some things that really triggered me. I didn't inherit my dad's liquor store. I built my dad's store for him. I knew at 17 that I was a fucking guy.

What's your dark side? The only place I feel like I'm dark is when I'm competing. We did rock, paper, scissors tournament with our leadership team. I quickly thought after I lost in the first five seconds, should I fire him? I was incapable of dealing with losing. What is it that makes me want to be like this?

And to be very frank... You don't have to give me the details. I'll tell you. It's... Five years ago when we had a conversation, I asked you what your biggest fear was. I've got these photos here. In Russia.

How does that make you feel? It's very clear to me. It's been there for a long time in my head. With age, my perspective and my recollection of my childhood and my understanding of what was most significant, defining and important has evolved. You've just celebrated your 47th birthday. Yes. More energy than ever, shall I say. But what have you, as you recollect on your childhood from that vantage point now, what are the new insights that you've attained about yourself? Probably the most recent one is like

this incredible need to be a superhero. You know, I really took the being the oldest brother to heart. You know, it's funny, my sister and I have a joke that a lot of people don't know that she exists because obviously me and AJ were in business together. And I talk a lot about the Jets and that has AJ. But my relationship with my sister, who's three and a half years younger than me, may be one of the most profound relationships I have. She undoubtedly was the first person besides my mother that kind of cheered for me.

You know, she looked up to me. My mother is incredibly close to her brother. And so she spent a lot of time building that relationship. We're incredibly close. I feel much more kinship to her when I think about my childhood than AJ, because I was 11 years older. We didn't have the same childhood. We also moved when he was three. So all my childhood memories have her in it. And I think as I've gotten in the last two, three years, I'm like, oh, I have this like need to be admired, need, you know, everything that works for me is when I feel like I'm doing it for someone besides myself. I'm doing it to make my parents proud.

I'm doing it to show my sister the right way. I'm doing it for my employees. Even the way I got into better health and fitness was I hired a babysitter, but really what I hired was someone to do it for. Mike and Jordan is who I want to make proud. Today, my scale being 175 versus 176.8, which was two days earlier, and Mike texting me great job on the travel day,

I did it for him. And so as I'm getting older, which was two days earlier, and Mike texting me, great job, on the travel day, I did it for him. And so as I'm getting older, and so much of the Gary Venus I'm realizing is I'm happy when I'm doing things that make other people happy, or even at a higher level, creating a framework or a blueprint that they can interpret into themselves. The thing I, you know, as I got older with my sister, a higher level, creating a framework or a blueprint

that they can interpret into themselves. The thing I, as I got older with my sister, a lot of things I talked about was, this is my DNA, your DNA is different, but I want you to be happy. It's gonna be different for those kind of things. And so, when I do things like this, I always go with the first thing that came to my mind. I think what's obvious to me is I've exhausted the conversation of grinding

and having to do it for myself and learning how to be an entrepreneur in the streets of New Jersey. And recently, in the last couple of years, I've talked more about candor. When I wrote 12 and a half, I'm like, this is my kryptonite. I'm great at candor in this format.

Put me on stage, put me on a podcast, give me 30 people listening to me, I'm cand, this is my kryptonite. I'm great at candor in this format. Put me on stage, put me in a podcast, give me 30 people listening to me, I'm candor king. Managing Dustin one-on-one, I just love him too much. Like, even this interview, like I went from a company offsite and like I got emotional this morning speaking to 35 global leaders. And that was the first time I got emotional

the way I usually talk about my parents if I'm at a gala or something of that nature. And it hit me and my observation was, oh, these people are becoming my family. I talk about Brandon Warnke, my best friend, and I tear up. I talk about my parents and my siblings and I tear up. This was the first time I kind of teared up for real, for real, deep, deep, deep, deep, deep in a setting when I was talking about those 35 leaders. And it was a nice feeling. I'm like, deep, deep, deep, deep, deep in a setting when I was talking about those 35 leaders. And it was a nice feeling. I'm like, oh, this is becoming family. And so, you know, I think, I think that candor has been a weakness on a one-to-one basis when it's emotional that I've started talking about the newest thing of this moment. When you ask me is what is it that makes me want to be like this? And to be very frank, it's quite enjoyable

and it makes me happy. And even when I don't deliver, I'm happy at the attempt of. And so I think I'll probably spend the next half decade trying to finish this thought and probably produce content around it because the thing I always think about is if I'm this happy, if I lack the anxiety that I see in 99.9% of people,

I have a sense of responsibility to over-communicate in case a sentence on a podcast triggers something for someone and starts their journey to be happier. I don't know something more noble a human can do than be on a quest to leave collateral, you know, droppings along the way that may help and will help others. So many directions I want to take that in. I'm going to go with the first comment you made, and then I'll move on to the second. You said, I have a desire to be admired.

Yes. Now, when I reflect on that, I completely agree. I think I lied to myself for a couple of years and thought that I was more noble than I was. But what I came to learn often from doing this podcast was that some kind of insecurity or some kind of shame was really the driving force at the heart of me. And as I sit here with athletes or Israel Adesanya, the UFC champion or whoever it is, you uncover these stories, which at a very young age, the thing that might have invalidated them when they were younger is now the thing they're striving

to seek validation from as an adult. Well, it's funny. I agree with that. And now I'm going to tell you why I walk around earth with gratitude and guilt. Everything you just said is one of my biggest theses in life. That is 100% true.

Mine is slightly different. I got really fortunate. It's like really hard to talk about even without like getting weird about it. I'm, my circumstances are, you know, I think yes, in some ways, for example, the system. School took such a shit on me in the 80s and 90s. And you know this, we've run in similar circles.

I'm very good at fighting the systems of industries. Like it's also why I see things like Netflix, you're gonna win, Tesla, you're gonna win because I know they're fighting the thing. And so I recognize it. I've been a good investor. I've been a good operator. And I'm definitely a communicator, college, right? I was at a talk yesterday. I'm not speaking that much, but I like my dad taught me, you know, keep your word. So I had a talk from pre-COVID that got canceled and then canceled and then I got COVID. And so I still did it. And so I did it yesterday and a couple of moms came up to me and both of them the way they talked

to me about the content I'm putting around college was through love and admiration 12 years ago those same exact moms were really angry at me you know and so when you see things you know you you kind of challenge it and so yes I think I absolutely the thing that was an insecurity, I get bad grades, but what was different for me is I didn't believe them. This is where self-esteem is an obsession of mine. Not delusion, right? Not delusion, because that's what a lot of modern parenting does.

You can do anything, Sally. No, you can't. Sally, you are not athletic enough to be in the WNBA. It wasn't that. It was this weird balance that my mom created between deep confidence but accountability and truth. I remember trying to make an excuse for striking out in a baseball game and trying to use the sun in my eyes as an excuse and my mom not letting me do it very subtly. Talk about childhood forming you. Like this is why I implore everyone to communicate their truth to their children, to the world, through podcasts, through content. Like it's amazing to me sentences change people's lives.

Right? She didn't let me do it. And I became very accountable because of those levels of parenting and realities. And that accountability led to so much happiness. But for me, when the school system was saying, you're shit, I didn't believe them. And so I watch a lot of people being driven by hurt. And I can sense that I'm driven by love. I just sense it. Like for me, it's just like deep self-awareness that understands how fortunate I've been. Like so many things went my way. The mom of the century, being able to leave the Soviet Union

in this little window in the 70, 1917, 19, in the 72 years that the Soviet Union dictated people's life. And to remind everybody, this is something most Americans and Westerners don't understand the Soviet Union was like North Korea it wasn't like Iran Iranians right now are able to leave Iran and go to Turkey you know wherever their passport is taken they can't go everywhere but Turkey takes their passport Dubai takes their passport the Soviet Union that my family grew up in was North Korea you were not allowed to. But this little event in 1970 of eight Russians trying to hijack a plane to go to Sweden to escape created a global story that led to pressure on Russia where Spain and Israel and America teamed up and had this little moment where Russia had spent too much money on their weapons of war and were starting to run out of

resources and conformed to their anti-Semitism and decided to take money from the US and Israel in exchange for a couple of hundred thousand people and I'm one of those people and I, born with insane levels of entrepreneurship and gift of gab and offense get to go from the worst place on earth

at the time for someone like me in 1978 to the best place on earth, fuck. And then getting all love but not delusion. And so by 10, being in the grit of like studio apartment with tons of family members and queen, like all shit, but being 10 years old and having little, but being happy as fuck and being loved insane

and now a 10 yearyear-old me realizes that money has no impact on happiness, I was built to win. I was built to win. And so I agree with you. I see it in so many of my friends. I always say the two ways to build something insane is deep, deep insecurity turned into fuel

or deep, deep, deep levels of confidence turned into fuel. On that point of confidence, you said your mother gave you your confidence. Yes. Earlier on you said she gave you your sense of sort of self-responsibility. Yes. But I've also heard you say

that she's responsible for your confidence. And then another thing, the market. So yes, my mother, and so a lot of people are listening right now and they had positive reinforcement. There's two things to watch out for for everybody who's listening. Parents or youngsters

or just try to get everyone listening and by the way, this is a good time to say this. I consume a lot of content meaning I consume no content. I consume how people are consuming content. I just want to give you some roses and really the listener on the other side.

I've really enjoyed and this is very lightweight. This is a hot take. It's not, I've really enjoyed, and this is very lightweight, this is a hot take, it's not like I've done major homework on this, but I feel like you have a very thoughtful audience. I really like what's going on with you and your audience, and it's really both of you, right? It's not just you,

it's who self-selects to listen to your guests, and you're doing a great job casting it and all that, but there's something nice going on here, so keep going, and everyone who's listening, kudos on you for understanding there's value here in a world of unlimited content here's the two back to like kind of the respect i have i told i told you dustin i said hey pay attention today i'm going to be a little bit sharper it's out of my admiration here are the two things i want to go extra level to watch out for in confidence building too many people go too far and they go into that eighth place trophy delusional place here are the two things I want to go extra level to watch out for. In confidence building,

too many people go too far and they go into that eighth place trophy, delusional place, and then kids don't believe you. I'm going to be very transparent. I've already sensed that with one of my children where they're calling my bluff on it. I'm like, fuck, it's true. Like, I played AJ much harder in every sport

than I'm playing Xander. That's the facts. And so I'm already adjusting my damn'm playing Xander. That's the facts. And so I'm already adjusting my damn self. Xander's your child. Yes. So one, it's don't let it be delusional. The whole you can be anything, you can do anything you want.

You can be anything you want. You just might not be the best at it or great at it. You can be a musician. It doesn't mean that you're gonna be a financially successful enough musician to pay for your household. Or if you want to be, you can. You're just gonna have to live humbly

and live your passion, which I think is going to be the conversation in 100 years. I believe the evolution of you and I and a lot of people listening is a lot more people making $61,000 a year doing exactly what has them on fire and living, this is a big part,

and living within the means of that $61,000. But that's a different conversation for a different day. So number one, watch out for delusion. Number two, you can't be the only source of positive reinforcement. Had I never gone outside and my mother did everything she did, I don't think I am who I am.

The other part that made me was ringing doorbells and having 81 people say, no kid, I don't want you to wash my car. And having six of them say, yes kid, I do want you to wash my car for $5. I think what also made me was standing on a lemonade stand for months in my life, you know, two days here, three days here, five days here,

months of my life from six to 13 and watching 99.9% of the cars drive by my stand and not react to my great signs and not stop and buy my lemonade. I think what made me was 100 out of 105 people said no to shoveling snow. What made me was I had a baseball card table and I watched 100 people walk by and not want to buy anything from me, even though I had good stickers and good cards. And one, the market made me. All those no's became enjoyable it's the yes that acts as the evidence though so it's the it's the person coming along in the one in a hundred buying the lemonade that makes a

young gary or young me go do you know what i can sell lemonade 100 and i was i've thought a lot over the years because the more i speak on stage or the more i my brand has grown i get the same question over and over again which seems to be at the very base level of everything I do which is how does one build confidence you've talked about your mum's sort of subjective evidence that you are great and then you've talked about the evidence from the one in 100 buying lemonade I came to this hypothesis that our self-belief like all our beliefs is just based on false or correct subjective evidence we have about ourselves. So if that is true, if beliefs or beliefs are just evidence, what's your view on how someone can build that self-confidence? They're listening to this now. How do they go get that evidence? And do you agree with that thesis?

Yeah, I like a lot of that thesis. I also think one of the things to point out that might help a lot of people is my mom also created positive reinforcement for me on the right things. When I think back to what she positively reinforced, it was not when I get the occasional B in history as a DNF student, which would be logical. This is the first time I remember saying this publicly. It's the first time I had a clear thought on it.

It would be logical for a mother who really, she knew how smart I was, she was borderline pissed. She's like, can't you get Cs to appease me? You're so capable, I'm like Ds and Fs. Why she didn't positively reinforce the Bs I got in history, which was the one class I paid attention to, is actually a very interesting insight. She didn't reaffirm a subjective machine

that wasn't built for me. What she reaffirmed and built confidence in me was how nice I was to everyone. When I think of my 47 year old self, I am the byproduct of two energies. I'm a successful entrepreneur, which is what the world taught me. And for the people that know,

they know, like especially the people that really know, they know how nice I am. Like, you know this, you've been on, you know, a lot more about me and subtle little, like what I love about you is you're smart. So I know I can say this, you know. Yeah, I know. Yeah. Right. And we've had lots of dealings over the space of five years. Right. In every subtle way, in every subtle way, we've theoretically competed. There's been moments where I could or couldn't come. Like what I love about this is you know. And I've always said that when I go into the grave, so many people are going to know me

that as long as the people that actually know me feel what I want them to feel, I can't, you know, there are people who today don't think I'm a great dude. And it's off of one clip that somebody wanted to use me to do a split screen to build themselves up because they're in the business of tearing people down to build their building and that doesn't bother me actually it's one of like i actually have incredible compassion for that person has it ever hurt not so i'm gonna tell

you something so when i became a dragon on bbc's dragon's den i i was exposed to a new level of public criticism and misunderstandings of often intentional misunderstanding so anything you say or do um are you know articles and different sort of sides of the political spectrum who maybe hate entrepreneurship at times sure doing pieces on me and then the backlash and then other like real sort of takedown efforts. Yes. And there was days where even my walls of like resilience and toughness, something kept me up at night. Has that ever happened for you where? Yeah, we're all human beings.

I'm not a robot. Yeah. It's that it's so not sustained. Tell me about a time when that happened. You don't have to give me the details. I'll tell you. There was a kid who wrote a medium piece about me being the face of hustle porn, which to this day lingers.

And it was a Medium article. I was on a plane. I landed and it was just all this chaos. And there was a lot of things that weren't true. I didn't inherit my dad's liquor store. I built my dad's store for him. There were some things that really trigger me. That one always hurts

because I think I did one of the most noble acts a human with talent can do. I knew at 17 that I was a fucking guy. And I decided consciously that I loved my parents so much that I was going to dedicate a decade of my youth, prime fucking years, 20 to 30 is fucking, you got time, you got energy, you got, I gave 10 of my greatest years, they're not my wisdom years,

but they're my fucking, fucking years, and I gave them, gave them to my parents. Never made over 120,000 a year, built a business from three to 65 million, left with nothing. Started VaynerMedia in Mike Lazaro's conference room at Buddy Media at 34 years old because I had no fucking money.

I'm proud of that. So you can imagine when somebody writes a hit piece and says, you can't listen to this guy, he inherited his dad's liquor store, that hurts. When you say hurts, what are the symptoms of that hurt for you? Oh, you're going to love this because this is why it's not sustainable.

I'm neutral at all times. Gary, you're the goat. Thank you. Gary, you're shit. I understand. Why does it hurt? I know that there is millions of 15 to 25 year olds,

30 to 60 year olds, 61 to 90 year olds right now who've decided not to consume my message because one person who's hurting decided to build themselves up by targeting me because of the platform I'm on and that disappoints me more than anything. As someone who is deeply, deeply, deeply driven by leaving the impact at the highest levels

that he is capable of out of the guilt and gratitude of winning the DNA and environment game, the elimination of opportunity to help make the world more about love in lieu of someone reinforcing their beliefs of living the world of dark and hate is crushing for me philosophically. But the reason it's not sustained, Steve,

is my number one fan on earth, outside of my family, whoever that is, Sally Pants McGee, and my number one person that hates me the most, thinks that the whole thing is the worst, can't wait till I die, I equally feel the same about it. Zero. On that day, you land from that plane, you see the, I don't know, Twitter or whatever's blowing up and all these people are saying those things. If I was sat next to you, what would I have observed? Hey, this is too big to not address in a world where 99.9 things I won't address.

I want to at least create clarity because it's gone too viral in a world that I admire. The readers of Medium are my contemporaries, my friends, people I admire. And so I just didn't want six or seven things that weren't true to be the foundation of a hypothesis, especially when you go read Crush It, which is my coming out moment. It doesn't talk about making money and buying a yacht. When it talks about working hard at night, it was under the context of the 2008 recession, people losing their jobs, and me saying, hey, I don't know if you know this, but the internet's getting mature, and if you go on YouTube and Twitter, you might be able to fix this shortcoming you have,

and yes, I understand that some of you are also equally, it's not just about getting a new job or getting a job, it's also, oh my God, because this was insane to me, because I was just coming out to the world now i was like in my little wine library bubble i'm like people don't like their jobs like that was like i loved it so much even if i was doing it for my i loved it so much that i was taken aback by that i was like well if you don't like being an accountant and you love star trek start making star trek video mean, it's insane

what TikTok and Instagram and YouTube have created. You go read Crush It, which I wrote in 2008. It's insane how much of that became true, even to me. You know why I'm asking, I think I'm asking this question and I keep persisting on this topic is because I've always seen the way that you've publicly responded in those moments. And it's always been with an unbelievable level of gratitude and empathy and so i as someone who's been on the receiving end of it it's hard it's hard so it's just it's just you know i'm sorry i was gonna say so i've always wondered from afar as someone who's been on the receiving end of it what goes on as the the first you know like the first reaction we have to these things where you're like yeah i mean the first, you know, like the first reaction we have to these things where you're like, yeah, I mean the first hundred, honestly, the first hundredth of a second reaction is actually a very weird blend of you'll see. And I can't wait to be gracious when you come

to apologize. And I've, I've had moments like that where the thing, the story or whatever will just stay on my mind. And it will rattle over. And it might rattle over for like six, seven hours, eight hours. It might rattle over at nighttime that night. It might even rattle over the next morning. Does that happen to you too? It's very rare for it to be able to get to the second day that next morning.

Very rare. I just go deep into the fucking Gary cave of, okay, this person I admire just took a shit on me. This influencer decided to shit on me. And I'm not talking about the comedians who I love. The comedian stuff is like awesome because I'm like, and I just did Dylan's podcast and I said it.

I'm like, that I'm like humbled by. Like actual good comedians. Forget about the people that impersonate me and have built, not their careers because they impersonate others, but a couple of these characters have really benefited from impersonating me and that means so much to me that I brought,

VCon was my crowning event and the first people that hit stage were impersonators of me. There's no bigger cosign I can give to like that feels amazing that somebody's winning. The thought that somebody's winning in their comedic career

because they popped by impersonating me, that's like the most humbling feeling of all time. Not that. Not when people take shots at me and like hyperbolize what I'm saying for a laugh. I'm flattered by it. I'm talking about people that really are like, fuck this dude. he's bad.

And it's so bad how they do it. It's so very out of context and things of that nature. I just, it just doesn't register. If I'm hurt by midnight as I close my eyes, and then the first thing I do when I close those and then the first thing I do when I close those eyes and the first thing I do when I open those eyes, I say to myself, okay, the world, all eight billion people have decided

to go on social media and say, actually, I'm a piece of shit. Is that better or worse than my parents dying in a car crash right now on the way to the airport? I'd much rather have all eight billion people go on social media right now and say I suck than that to happen. Thus, I can't be upset about this in a real way. There's bigger problems. There's bigger problems. You referenced something earlier, you said wisdom years. I found that really, really compelling because you referenced, you know, I think you said 20 to 30. I'm now 30, just turned 30. So I guess I'm in said wisdom years. I found that really, really compelling because you referenced, you know, I think you said 20 to 30.

I'm now 30, just turned 30. So I guess I'm in my wisdom years. And one of the things- Well, I think this one's the in-between. The 20 to 30 is like, right? Like just fucking go ham. And for everybody listening,

this is the years to taste a lot of shit, make a lot of mistakes, have fun, try different things, like everything, eat it all. Go to the go to the you know the salad bar and try every single thing that's in there 30 to 40 is the refinement of 20 to 30

especially if you really go at it you're like okay i remember like 30 30 is when shit started popping for me february 21st 2006 is my first episode of Wine Library TV. So I'm 30. I just turned 30. And that is, I mean, the fact that within December, January, within three months of my 30th birthday, the very clear public data, very clear indication of the shift in my career

happened three months. So that was interesting. And I think those are when I think of 30 to 40 I refined a lot of things that felt natural 20 to 30 I refined my craft I started to get to know myself better when I think about 40 to 47 I'm like that's an evolution of 30 to 40 I'm still refining I'm still doing but I'm starting to get into a thought of like, okay, I like have real grasp on things. I can do some real damage. Like I'm scared in the most positive way

of what I'm going to accomplish selfish, selfish and selflessly from 50 to 60, scared. I think it's going to be banana shit. I think everything that is me right now is minor leagues compared to what I'm going to do 50 to 60 because I now have the context of 40 to 50, which is a more polished version of the refinement of

30, 40. And so for me, 50 to 60 feels like insanity. And then when I look at my 60 to 70 year old business friends, I'm like, fuck, I get an entire another decade after that decade of doing it at 100. And then I start debating what happens at 70, right?

Then I'm like, 70 to 80 is still a very clear decade for a certain very small group to continue to go ham and go fucking insane. I'm curious where I'll be. I know to 70, I'll be exactly the same way I am right now. It's inconceivable I'm not. Those 23 years are pretty clear to me. They're gonna look like the last 23 years. 70 to 80 becomes an interesting debate.

Will I take any foot off the pedal? Will I go to a different place? I often fantasize of going into a cave in Peru and whoever wants to find me can come and we get 30 minutes and I just do that for the next 30 years of my life. I don't know. Obviously, there's that very silly but very emotional goal of buying the jets for me that's more fun to chase than

like I almost think I the first time I might feel actual unhappiness or weirdness or some sort of version of like might be if if I buy the jets like I think about that a lot I'm like if this happens was this such a romantic journey this is not 30 and 40 and 20 year old Gary thinking it's cool to say this. This was 12 year old Gary telling Robbie Turnick and Eric Godfrey, I'm gonna buy this fucking team. This has been like a thing, like actually, like forever. On that point of those wisdom years,

one of the things that came out of my refinement, as you call it, and my kind of, maybe I'm just at the start of my wisdom years yes because i look back on my perspective on exactly what you've talked about i'm like hustling and like my own um insane luck of being a very optimistic person in the worst situations and i wonder i say steve is mindset a privilege and if and if it is because you described yourself as being as happy you've always had this this drive this motivation is there a risk in us if mindset if our mindset is a privilege in trying to advise others when they don't have the same privilege couple things one everything's a privilege yeah

do you see what i mean though like of course i got really scared i think in the last two years this is incredibly powerful first of all as a whole separate and intriguing conversation everything is a privilege and everything is a vulnerability and this is like a incredibly important subject to talk about i think mental content is the ultimate privilege yeah i think the second one is beauty i'm fascinated that we haven't gotten yet to attractive privilege. When I look at men and women navigate this world, there's nothing more clear to me in the privilege. They're like white male privilege.

I'm like, attractive privilege makes that shit look fucking minor leagues if you look at the data. So let's look at that then. I want to go back because I don't want to lose it and I will lose it because I know how we roll. I have no interest in thinking that I'm telling anyone what to do or giving, I do not think that I'm giving advice. I really don't. And I don't touch on this enough,

and I have touched on it at times, and this is a great format to touch about. I have no belief that I'm right. I have no belief that I'm giving advice. I have no belief that anyone listening to this should do what I'm right, I have no belief that I'm giving advice, I have no belief that anyone listening to this should do what I'm saying. I am putting info into the system and I'm hoping that people can extract

something of value for them based on their own self-awareness of themselves. Most people don't have self-awareness. I'm aware, which is why I talk about it so much. Yeah. There's a reason I talk about self-awareness so much, why it was a pillar of my last book, why it's a big character in V Friends.

Self-aware hair, self-aware hair, the tortoise and the hare. Yeah. I think people don't, one day when I'm, you know, I think 47-year-old Gary for cynics

and people that were watching is better than they thought it would be than 27-year-old Gary for cynics and people that were watching is better than they thought it would be than 27-year-old Gary, right? Like the hot takes on, I'll never forget when I hit the scene on Twitter, the whispers at conferences, I could hear them in the back, in the green room. And I definitely read it on Twitter

because I was like popping. They're like, out of everyone who's popping on Twitter in 2007, the consensus was the only person that won't be here in a decade is Gary. Because it was too hot, too fast, too much. People literally, I'm empathetic, when you have this kind of energy, I'm empathetic to how this story plays out

for different people. I get why the person burns out, I get why the person really does the ultimate bad thing and disappears off the, I get what that, but that's because I'm not on the extreme insecurity side. I'm on this other side. So I always knew. So, but one of the things,

so I get a lot of like joy out of like knowing that so many people didn't think I'd be there and I'm at the top of it. Same way I feel about V friends. Nobody has a clue, including my inner circle, of how much thoughtfulness I did in character development.

This is my Disney. This is my Sesame Street. Big Bird, Mickey Mouse, right? Optimus Prime, Pikachu. Like, self-awareness is profound. The story of the tortoise and the hare is profound to every listener of this. There's not a single listener right this second that's listening here right now. If they're eight or if

they're 88, that isn't extremely vulnerable to the lack of patience because they're too ambitious. It's the reason they're listening. So self-aware hare for me is a phenomenal story I get to tell for the next 50 years. And I can't wait to make self-aware hair more famous than Gary Vee is today because that will be the way I scale putting positivity into the world, VeeFriends. And so I'm excited about that. But back to your point, my friend,

as long as you come from a place of humility and understand that ego kills people. Yes, we have some luxury of mindset and communication, but for me, I don't think people should listen to me. I think people should listen to everything and try to find positivity and usability out of everything. And they should dismiss what is clearly negative and selfish and they should triple down on everything that is selfless and positive

and that is the answer to your question that started here. What should people do? They should be very, very focused on trying to do the following. Lean in dramatically more to things that are positive. Your grandfather, podcasts, upworthy.com, lean into positivity.

Then they should be on the awareness, eyes wide open, on is this delusional and lacks practicality? Like, you know, if I just dream it, it will happen. No. Lean in, cut out. Literally when this podcast is over, step back, audit your entire life from the people you spend time with, your family, your friends. Look at every person you follow. Are they triggering your insecurities for their own self-interest or are they trying to put love

into it so that you go on and do your thing watch look for it but whatever you do back to like working out like you know protein and you know when i when you know when mike vacanti is like all right you did a lift like protein i'm like really okay and like during covid i'm like wait a minute i'm starting to finally get some muscles oh because i was doing protein as fuck after lifts and not after not lifts i was doing it right here's something right for everyone cut out one hour of negativity add one hour of negativity, add one hour of positivity. If you're listening right now and you're like, social is such a drag, it's because you're in a drag mindset and the algos and the people you follow are following you.

You know what my social looks like? Fucking sunshine. I'm being dead fucking serious. You know what my algos look like? Fucking sunshine. In the world of the momentum of darkness right now, sunshine. You know why? I choose to fight for positivity, but I refuse to not be grounded in practicality, which is why I've always thrown curve balls. Love everybody, it's all awesome.

Fuck eighth place trophies. What, Gary, what? What? Eighth place trophies lead to entitlement and fear of losing, and it fucks up kids so like it's kind of that juxtaposition practical positivity is something everyone needs to add more and so back to your point we are going to put out stuff forever because it's how we're wired the people who are listening right now for a lot of them they need to understand where they match with us and where they don't. You and I match on a lot of things.

There's a lot of things we don't match on. The person on the other side needs to figure that out. You, I would argue, watching you from afar, we know each other, but not that deep. We never, we haven't had those six hours that we need that we will have in the next 50 years where it starts to get even closer. But even from afar, it's clear to me

that you're understanding more and more what is right from the messages you've heard and what's not right for you and you refine it and you refine it. To your point, I say it all the time, please don't be me. The only thing I want people to be like me is be as happy as me. That's an insular game.

That's a self-awareness game. That's a process game. That's the only thing I want people to be like with me like I'm weird I've got a lot of weird nuances I do a lot of things that are not scalable I don't maximize for I'm always worried when people are like oh I want to learn how you build your businesses I'm like it's real different like you know I don't maximize for profit I maximize for retention of relationships if you aren't as confident as I am when those people leave and compete with you, you become grudge-oriented and envy-oriented

instead of happy-oriented. Like, I've got some weird elements that people can't run my playbook, but I couldn't run other people's playbook. So pay attention, find what works for you, try shit, try it multiple times. Steve said something you like, try it once. Didn't work?

Steve's not an idiot. You don't suck. Try it again. On this, the very crux of all of this is that key point which is about self-awareness and as i realized that in my late 20s that self-awareness was really the key to um to most things in life and i remember writing a quote on my instagram which is still my favorite quote of all time where i said um there's no self-develop um there's no self-development without self-awareness. You can read as many books as you like, but if you can't read yourself, you'll never learn a thing. It's why I've never read a book. Yeah, exactly. So like, to me, the only thing I've read is my feelings. So how does, how does one person listening to this now that's been listening

to our content and, you know, they really want to be a, an entrepreneur, they want to have a big media company, whatever it might be, but they don't know, they want to have a big media company whatever it might be but they don't know they don't have them like but objectively they don't have the minerals well how do they go about discovering they don't have the minerals by going in the pool and drowning okay you know it's not for you and i to judge because we've been wrong too much yeah i've been wrong so much it scares the fuck out of me and i'm gifted with intuition that when i'm dead, I hope they can test for it because I think I'm all time. And I've been wrong a ton. That makes me believe everyone's wrong.

So if you're listening, here's a couple things that are good call out that may bring value instead of what I just said. Asking what you're in it for is humongous. Yeah, this generation, I don't think they know. Because people come up to me- And you know this, first of all, you're part of this generation i don't think they know because people come up and you know this you'll first of all you're part of this generation young guy that's how i know but you know but i know too but guess what my generation this i'm so done with this my generation didn't know either

guess what when i was 22 all my friends wanted to hook up to all my friends wanted a bmw too and by the way as somebody who observed people his whole life the people that were older than me the people that were buying expensive wine for me when I was 20 and they were 35, everybody wants stuff to communicate to others that they're winning. We've been putting on makeup since we had fucking clubs hitting each other. Like, it's what humans do. We do things to communicate. Status and stuff. Yes.

Why? To hide. We're hiding. We used to do it with status right now we've decided to shit on each other our current move to hide is by tearing each other down that status too though i want to be more i want to be the most leftist i want to be the most on the right i want you know of course the problem is unlike buying a bmw and going into debt when you're doing this one you're hurting other people's feelings. It's one thing when you're hurting your credit score.

It's another thing when you're trying to make someone feel bad about themselves. That's why the acts of us collectively at 8 billion people right now is completely and utterly unacceptable, which is why I'm desperately communicating at the highest levels about the stuff that I want to put into the world as a counter to people's us against them. desperately communicating at the highest levels about the stuff that I want to put into the world

as a counter to people's us against them. Girls versus boys, blacks versus Jews, Republicans. It's fucking exhausting. Like once people understand there's one team, humans, you can be mad at elephants, you can be mad at falcons, but like being mad at each other is the most counterproductive thing. And we need to go into tribes, my country, my sports team.

I understand this because I hate all the other football teams. It's the only place I get those feelings. The way people feel about Republicans and Democrats or genders and races or countries. The only place I can touch on it emotionally is American football. My level of actual disdain towards Patriot fans is real. I feel the rage. But the fact that I do that for something silly that's a form of escapism that's a couple hours a

week to like reset and like enjoy and escape like people watch movies or ski or exercise. That's silly. That's football. That's silly. We're doing this in real life to each other. And it's got to stop. And I think it starts with people understanding if you are shitting on others right now,

it's a complete reflection to your own unhappiness and insecurity. I had a kid come up to me and this is why I was asking the question is after I did a talk and he said to me, as I knelt down on stage, he said, I want to be, he must've been 18. I want to be a public speaker too.

And I'm like, why? Why is always the right answer. And the answer you'll get from this generation, this my generation is, well, I want to change the world, Gary. Yeah, of course. And then you go, what do you want to change about it? They go, in fact, what I came to learn

is they want to be the type of person that's known for changing the world. They want the admiration. That's right. They saw the audience clap and they want that feeling. The money, the fame, the accolades, the blue check, the followers, the fun. I understand.

It's the problem with all the things I just mentioned is they're a vulnerability to your own happiness if it's not balanced. There's nothing, by the way, sometimes people get mad at me in the other direction. They're like, fucking Gary, I worked my fucking face off, I can buy a fucking watch or a car. I'm like, of course you can.

The why? If you like love the shit, like I don't understand sports cars and the feeling of going that fast. That's not me. But I understand buying rare sports cards and that's enjoyable. If you enjoy that, that's phenomenal.

When I talk about materialistic things, I talk about makeup for insecurity. If you are burning the midnight oil, you know how people burn out? They're working till two in the morning to buy the expensive car, to use it to close their insecurity to get the affirmation from the opposite sex or their friends that's that that system's broke it won't work i i mean i don't know what to tell you like everyone's like okay gary but i'd rather have the fucking money like

this whole like i'd rather cry in my ferrari than drive a Toyota or take the bus, you say that. Do you really want to be in a mental place where you're on the borderline of suicide and you have heavy drug usage, even though you make $3 million a year, $17 million a year, because you know this now, Steve, you've worked very hard and you have the talents and the luck of the draw and you put in the execution

to now run in circles where you know what I'm about to say is ungodly true, which is the following. An extraordinary amount of people that have unlimited resources are desperately lonely, insecure, unhappy, and borderline depression suicidal. That's just truth. And so like the thought of me talking in any other direction when I know that to be true Seems like the least authentic thing I can do But even when you say that you must know that for a huge amount of people including myself We have to have that hypothesis that those things will give us some kind of

Fulfillment or meaning we have to have that fail us before we learn the lesson gary's words Versus the insecurity that was developed from my mother and my father on the playground, hypothetically. One of them, you know, when I was seven years old, the kid said I'd never be nothing. Then my teacher, I'm not talking about myself. No, I got it, I got it. The teacher comes in and says, you're an asshole.

I think that's right. On one side of the scale, you've got Gary's words. I don't think it's either of those. I think it's the macro conversation of happiness. I believe if the kid's getting picked on, you'll never be nothing. And she or he decides, I will be content at 25.

I will have peace of mind. I will smile 89.3% of my life. Instead of I'm going to have a mansion and a super yacht, I think she gets crazy. You're describing me there. So I, at a very young age, only black kid in an all white area. We were also the poorest family.

So we understand the value. So you had all the advantages of adversity. Exactly. Yes. On the context I was in, I was the Blackberry in a world full of iPhones. So I had that feeling of like not enoughness. I get it. That means that as I of like not enoughness. I get it. That means that as I go off into the world,

I'm convinced my subjective evidence is if you get the material success others have, if you get there, then you'll be happy. Nothing on planet Earth could have told me different. What if your 17 heroes on TikTok and YouTube were talking about something else? Hold on. Yeah, yeah, yeah.

No, no, this is super duper important. What if you're 17 heroes, how has everything changed in the world? Can I say why that might not be enough? Because those first 10 years as we learn in childhood psychology. The problem is in those first 10 years, you will have heroes outside of your family.

What if your seven year old you on YouTube Kids finds a hero or on ESPN app or something? What if Messi, your hero at seven, in every other interview spoke about peace of mind, living with it? What if the conversation changed? Because the conversation has changed on race, on gender, on religion, on status.

Tulips used to be the most important thing. In your life. The king, the king. Do you understand in America in 1968, in 1971, in 1971 in America, if you were an astronaut or pilot, you were cooler than an athlete. I want everyone to fucking pay, like this is a big fucking deal.

This is what my fucking mission is. In 1971, in fucking America, if you were an astronaut or pilot, you were more famous than everybody but the top 10 athletes in America. Joe Namath was more famous. Love him. But you understand?

Do you understand that Joe Namath is actually a great comp. The Jets quarterback that stunned the world in Super Bowl III became a sex symbol. And that started to change. He was a celebrity, which was different. You and I are affected by entrepreneurship now being a celebrity status, something that couldn't have even crossed my mind when I was 18 years old,

maybe even 30, your age right now, 30. It was starting to, because you have to understand, do you know who was the biggest entrepreneur when I was your age? Bill Gates, the nerdiest fucking looking person on earth. Think about how, but this is why it's fun. You're properly speaking in the framework of our society now.

My argument is that communication changes frameworks and what if we collectively got on this boat? I wanna, so here's what i'm thinking so if if we manage to get seven-year-olds absorbing content which i imagine is probably a lot of your plan with v friends that is empowering that is creating new evidence in their mind purple not red or blue yeah right back to republican purple right like like competitive clown is a motherfucker accountable ant kids is the thing like if if you lost, you fucking lost. I don't want to over coddle it.

Yeah, yeah, yeah. But in Gary Vaynerchuk's seven-year-old world, if his mother was crying on the kitchen counter every day because of, I mean, we started this by talking about- Using Gary Vaynerchuk and Steve and not acknowledging that there is extraordinary amounts of people that are bringing joy into the world that had alcoholic parents, depressed mom and dads bipolar moms and dads lose it my mother lost

her mom at five and her father ready you know why i have confidence in this let's talk about tamara vaynerchuk not gary vaynerchuk tamara vaynerchuk was born in the soviet union in 1955 about as bad of a fucking draw as one can get. She goes on to get another tough card. It's called her mother dies at five. She goes on to have an even more insane card, which is her father goes to jail for basically, in this environment right now,

this will make sense to people finally, for being Jewish in the Soviet Union. And he went to jail for 10 years. She finds herself at 10 with her mom dead and her dad in jail for a decade and a stepmom raising her who's a young kid

who doesn't know what the fuck just happened to her either, right? All the family's gone because everyone's like just fucked up. All the dynamics, the mom's side,

the dad's side, you're following the story. She goes on to become the person that built me because she is me and i am her more importantly the core positive person for any person in her life from acquaintance that met her once to clearly her three children she exists i'm not saying that any early experience defines which way you're going to go and i'm trying to say that any early experience is going to be good yeah yeah could any experience from you between the age of zero and ten i could be a major factor right and i've sat here with these childhood uh psychologists and therapists like

gabble may who studies childhood trauma in that first 10 years of your life if your parents are constantly i believe in that crying i believe in that you know so i believe in by the way just so everybody who's listening because it might seem the opposite, because I'm kind of going fast. I believe in that, comma. There's something I believe in. If one person that lived that cliche life has gone on to be an incredibly happy and productive person,

it now means it's capable and true. I've noticed this in my guests on this podcast. So I'd sit here with a guest whose father was um incredibly violent and did domestic uh domestic violence on his mother yeah this person is the kindest person i've ever met i've sat here with someone whose father did domestic violence because there's a layer between what happens in their interpretation overreact in both directions it's it's it's your interpretation and that's what the childhood psychologist said to me he says you can there's what there's almost like having sunglasses on your eyes steve there's nothing else you know that right yeah 100 there is nothing else on earth yeah so the point the point here is um regarding that person who grows

up in a household where they interpret yes that money is the most important thing do they then have to have that belief fail before they can learn that the lamborghini isn't gonna because for me i just can't imagine a world where that was so deep inside me that insecurity and shame i can't imagine a world where steve bartlett doing a quote on instagram or doing a podcast would have been stronger evidence than watching my parents scream at each other every day my argument is you don't know you just know the alternative and i would argue that many people like yourself and I know weird things because we get unlimited DMs and emails. And you know this about me

because this is where I'm a little weird. I took a six hour flight yesterday and read a gadrillion DMs. I think what I do that's a hair different than a lot of my contemporaries is I'm in the dirt heavy like I really still see extraordinary levels of value of being in the trenches reading those dms replying to those dms like long after I mean I'm watching people get 10,000 followers and think there's somebody and get an assistant to reply like I'm still in it and in in that, I see it. There's a reason that people that were deeply

alcoholic have been able to be sober the rest of their lives after going through a process. There's a reason that therapy is profound. There is a reason that meditation is profound. There's a reason that exercise is profound. To me, everything you just said is right. But it is the cliche, you get a hand and then you got to play it. And as someone who's not good at poker and has won many hands with 3-7 offsuit because I'm just a fucker like that,

I believe in that in life too. There's every version. Do I believe that to your point, I believe more than anything that those first 10 years, there's so much going on, it's insane. Including the environment you're in, right? Yours was one, mine was one. But do I believe that if you then decide like many do, well, I got fucked. I got fucked. Well, then if you've decided back to perspective, being everything, if you've decided I got fucked, well, then the game's over anyway. The fuck are we doing here?

If you've decided I can't because I was unlucky, my mom this, my dad this, my country this, my gender that, my income level this, well, then it's over. It doesn't matter what I think, you think, anyone else thinks, it's over. I just refuse to talk to another human being and believe that to be true

because there's been billions of examples of the alternative. Billions, Steve. There's been billions of alternatives of the exact opposite. I agree with you. It's just that point sometimes I ponder, which is you'll meet someone and you'll think this guy, regardless of what I say to them, or this woman is going to have to have their current worldview fail them. By the way, I believe that about every person. I don't believe a single person that I've inspired or got through to now wins. They have to taste everything for themselves. Yeah. You said you're weird. And I sat with Tim Grover. Tim Grover, who used to train LeBron and MJ and Kobe, he said to me that we all have our brilliance our greatness and then often connected to that and responsible for that is our dark side that's the word he used the thing that

you know becomes the the star wars the difficult wars what's your dark side? Probably my unhealthy. There's a version of me on a competitive scale that can get dark. I'm incredibly competitive. The only place I feel like I'm dark is when I'm competing. Like it's crazy. Moments ago, a couple hours ago, we did rock, paper, scissors tournament with our leadership team as an exercise. I lost to Peter Chun, head of platforms, the guy that talks to Snap and everything. I quickly thought after I lost in the first five seconds, should I

fire him? Of course, Steve, there's a little ha-ha, but if I'm being naked and authentic and transparent to this audience, thank God at 47, the wisdom years, I used to punch, if Dustin Bingham, Joe Minakawa,

Glenn Curtis, Eric Rainey, can you guys all stand up and go to social media and tell everybody the following truth of what happened any time I lost in Madden 94 in a dorm room? I would punch a hole in the wall knowing I would have to pay a fine with my own money, but I was incapable of dealing with losing.

Why? Because I wanted to win. Yeah, but why? Because it felt better than losing. Why? Because I wanted to win. Yeah, but why? Because it felt better than losing. Why? Not because of the great place you're going with this path. It's really funny, it's no different to the... One of the great lessons, I've gotten so weird

that there's a part of me now that wants me not to buy the Jets more than buy the Jets. I've seen this evolution. Because I want to show the world how pumped I'm gonna be for Sarah McGee who bought it. And this is a brain fuck. But I'm starting, I lived my whole life saying, if I can show kids that you can go from not being able

to afford a fucking jersey to buying the whole team, I can help. Now I'm starting to believe when I show the grace and happiness for someone else's accomplishment at the expense of my lifelong dream and teach people that it was the great enjoyment to try it, that I can have a bigger impact than showing that you can do it. That's winning in a different way.

In a very different way. And that's what happened with me with winning and losing. I wasn't per se trying to, listen, again, I am not a robot. Everyone's loaded with insecurity. I have insecurity with girls much more than business. Like nobody was scary to me to talk to in business, but Pam Moses in high school, like even though there was a clear indication

that she had interest, that was still like, ooh. Whereas I could have had a meeting with Bill Gates the next day and be like, I'll beat you. Right. So we all have our places, right. Of insecurity, things of that nature. But like, you know, when you're five, like there was just such a, like, I love competition and I'd prefer to win. Right. And I prefer to win. I did not have a relationship with it from three to four to 12. Now, one thing I love, and I'm watching a lot of kids now

because I have kids growing up, here's where I get interested in tenacity and self-esteem. I would lose and I liked it. So there's some, you want a dark side? I like losing. I might have cried and been pissed and wanted to do something about it, but I wanted to play again.

There was almost this weird enjoyment of losing more than winning. As a matter of fact, I cheered for four teams growing up as religious as I am about the Jets. The New York Yankees, the New York Rangers, the New York Knicks, and the New York Jets. To this day, I am so wildly weirded out by the fact that I love the New York Rangers and the Yankees as much as I like the Jets,

but the Rangers won the Stanley Cup in 1994 and the Yankees won the World Series in 1996 and the next day, I stopped following them. For real, no bullshit. It wasn't a plan. I was 18 years old when the Rangers won the cup. I didn't think of it as like the thing I wanted to do. I literally woke up that next September, October

when the hockey season started and I didn't want to watch. Why? Now at 47, I believe it's my addiction is the process and the game, not the thing. And where did that, you're clearly a unique standout person that loves to win. Where did that, like, was there an early moment where that was reinforced? That winning is great, Gary?

No, as a matter of fact, it was like not even like talk. You know, this is why the 80s were epic. And more importantly, I'm joking. This is why my mom was epic. It wasn't like she was like, you have, like, there was no talk of that. It was just pure DNA. I'm massively competitive. I like it.

I like the game. My brother has it. My dad has it. Like, we're competitive. I think it manifests in different people, but it wasn't reinforced. It just was like innate. And I really like where I have it now at 47,

which is like, I've learned how to deal with the fact that I'm not the best at everything. That's what life taught me through the years. But I really like trying. You know what's one of my favorite scenarios? This is gonna really, by the way, if this resonates with you, please email me at gary at vfriends.com

or gary at vaynermedia.com because I think this is gonna resonate with a lot of people. I thought about this yesterday on a random thing. I must have saw something on social. My favorite thing, one of my favorite weird tiny things that I know is going to resonate

with 2% of this audience, but please hit me up because I want to get to know you. When I'm on a pickup basketball team of random people, like friends play pickup basketball, five on five, college, high school, your buddies get together. When our team gets smoked, like 11-3 in the first game,

the second that 11th point goes in, I get so hyped. When you get smoked, 11-0, 11-1, as you, you know, you play pickup basketball at all, no? We play pickup soccer. I know, football, proper football. Football, yeah. In basketball, and this may resonate in other sports, cricket if you're listening in India, football around the world, we play pickup soccer I know football proper football in basketball and this may resonate

in other sports cricket if you're listening in India football around the world when we get smoked where it's very obvious to everybody that four of the five

best players are on one team and that's why the score was 11 to 1 everyone's natural inkling is to like let's reshoot

for new teams mine is this deep excitement to get the other four people together looking at everybody's face and say guys we're fuck like immediately like we're not fucking shooting for new teams let's run it back and then huddle and i look at everybody's fucking eyes i'm like my friends we're gonna win this fucking game because we're gonna outwill them even though they are dramatically more talented we're gonna out win this fucking game because we're going to outwill them. Even though they are dramatically more talented, we're going to outthink them.

And most importantly, we're going to outwill them. And when that happens, because by the way, 70% it doesn't happen. The talent is just too great. And unfortunately, we also found somebody on the other side who's talented and has will. But the feeling when you know that you are dramatically inferior and you get a group together and you out accomplish them predominantly on will with a mix of strategy,

there's something there that just gets the hairs on the back of my neck up. Is winning associated with your own sense of self-esteem? Definitely not. One of the things that makes me so happy is, here's a great indication.

I didn't know that until probably the last five years. This is the truest statement I will say on this podcast. My professional success has no currency with my heart and soul. This is where my life got really fucking crazy. You know, you know this, you're going through an introspective moment, clearly in your late twenties and like, it's clear. So this is like fun for me to tell you. I'm like really in the zone. I feel like we're sitting and just like, you know, having a drink. When I realized somewhere about five or six years ago, oh fuck, none of my professional accolades,

net worth, exits, followers, awards, even things like being on the board of Charity Water and Pencils, like even when I was getting admiration for, when I realized none, none of my professional successes make me think it's a reflection of me or is an indicator for me or is a barometer of self-worth, it fucking took, I was already flying, it took me to the fucking stratosphere.

My entire self-worth is wrapped up in the middle of this podcast when I looked at you and said, you know. My entire self-worth is 100% predicated on people knowing the truth of how I've interacted with them. What is that, Matzo? I have a deep love for human beings.

I love them. For example, back to being a little transparent, I'm a little weird with animals. I have a little bit of a level of resentment towards animals. This is something my inner circle knows. You know, we joke, I don't hate dogs. I do hate that humans default into loving dogs with all their heart and don't do that to each other.

I struggle with that. I got so damn lucky, Steve. I came out the womb, my mom talks about this a lot. You know who I was in the playground at three years old when we first moved to America, like immediately running to all the 80 year olds and schmoozing with them. You're fucking four.

You didn't read Malcolm fucking Gladwell. You didn't listen to Gary Vee. You're fucking four. I'm fucking four years old and I'm going out with my Jessica Shia, my grandfather Shia, and I'm fucking gabbing it up with the 82 year olds and like desperately trying to make them laugh and smile because a lot of them came from Russia

and were sourpussed in the last stage of their life. America was fucked up when we all got here. It was a real recession in the Carter years. Queens was fucking Queens back then. Not like it is now. Like it was fucking, and like I had a deep need to make these 85 year olds smile for a second

because they weren't smiling the rest of the day. It's who the fuck I am. Whenever I've observed you, especially in the pre-pandemic times where you were flying all over the world and talking in every corner of the world, you were on some other shit. And I was to some degree too.

I remember I lived in New York, but I was traveling 50 weeks a year, but you were on some like other shit. I was looking at you thinking, fuck, that's the only guy that's out working me. And I'm thinking this dude has a family. Yes. I was a single dude living in a studio apartment and you know i

get that but you so the question which i'm sure you've had level at you and over again is what's the cost there there's cost there's cost to everything but one thing i did extremely well was and i still do this well um is I over-communicate things that I think bring value to people and I don't communicate things that I don't think bring value to people or things that are important to me that can be owned behind the door

instead of in front of the door. So I think people would be really stunned by how much family time and personal time I have. Do you have regrets? Of course. What kind of regrets do you have? You know, there's certain things that I'm not ready to talk about,

but I think people are, I'm too public of a figure to people know there's things that have happened in my life more recently and things of that nature. So of course I have regrets. I also have regrets that I think will really help people, which is that I am ready to talk about, which is no bullshit. I should have went to a couple more high school parties. No bullshit. I shouldn't have come home every weekend when I was in college and worked in the liquor store. I should have did a keg stand

or two here. No bullshit. Like I should have taken more vacations in my twenties with my buddies. You know, like, like I should have had a little more fun. The truth is, I'll tell you why that was all hard for me to say. They're micro, micro, micro, micro, micro, micro regrets. These are like, yeah, they mean like these, I have nothing in my body, including some of the stuff I'm not ready to talk about. That's like, fuck, you know, like I'm in pain over this. They're just like little micro regrets. And I answer this because I want people to see a clear picture on the other side. Like if this was me and you actually having a drink, the answer might have been no. The only reason I think I just said yes is because I think it's important for people

to know like nobody's like, I'm just scared that I'm so happy that it seems almost like bullshit, but it's just kind of true because I always go to the same place. I'll give you an example. I think real regret is only grounded in a very small circle of the people you love. I really do. And I've put the fucking work in on the family side. It's funny. Actually, that was a really interesting segue. The fact that I can say to you no

because I've put in so much deposits on the family side that actually I'll give you a good one. I've got a brewing regret. My best friend in the world is Brandon Warnicke. I met him the first day of freshman year of high school. Within the first six months, I'm like, this guy's gonna work with me. We did baseball card shows together.

I knew I was gonna build my dad's business by then. I wanted him. I fucking courted him to be in that business from sophomore year on. And he became my partner in crime along with Bobby Schifrin, my second cousin and my dad, and we built Wine Library. Lately, I've been feeling that we have not had enough friend time one-on-one as we start going and starting to see 50 and it's something i really want to work on

i am i asked this for very as if the cameras weren't here and the microphones weren't here i i'm earlier i'm 30 years old yeah and i want to know the advice from you someone that i consider to be a mentor and a friend you're an investor in one of my companies as well. Um, on that, as it relates to that family and that personal piece, what I might get wrong. Cause I know, I don't think, I don't think there's wrong. I think somebody watching me might say, you're doing this wrong. I might watch you and say, you're doing this wrong. Uh, I gave some advice to a friend of mine, Ryan Harwood, in a pool in Miami a couple of years ago that I feel great about. I checked in once in the last three years, curious if he was doing it. I'm positive I'm right, but I'm not right. Because what's so interesting about being,

we're all unique, but I have a sense of like how I roll. the amount of things that people have observed, including my mom, who's the singular person that knows me best. We share 83% DNA. That's obviously a subjective number, but like I'm trying to paint a picture of how similar we are. Even she is remarkably, and she is the, I am so intuitive because of her, but earlier to this podcast when I'm like, I get wrong all the time, nobody has the ability to be more right about me than my mom. And she's wrong about things. She has been wrong.

She's been proven wrong. And so what that did for me in the, you know, I put my mom at the highest pedestal is, oh, me judging Dustin or Steve, like I'm going to be wrong all the time. I know nothing about them. So what you need to know is yourself. What you need to know is yourself.

For me, regrets are completely grounded in did I spend enough time with the people I love? Did you? I believe that above me, I absolutely have. That my parents today could go and I used to be scared, both my parents, my dad lost his dad at 15. I already told you about my mom.

I lived in fear. You know, actually we didn't get on that. That one, that one is something I wish I popped up 20 minutes ago in this podcast. The fear of my parents dying because both of them had a parent die at a young age was a profound currency in my life in my first 15 years, profound. And so I think because I'm on the other side of it,

there's such heavy levels of gratitude that I got to keep them that I'm like pumped about it. And I can tell you today as a 47 year old man, my parents are young. I expect another good 20 years minimum, hopefully 30. They're like in their late 60s, right? I'm looking for 30. But if God forbid, I won that game in a way

that a lot of people haven't. I like was with my mom all the time as a kid. I was with my dad 15 to 35 all the time. I've checked that box. I mentioned Brandon. I think about other people I love like Bobby Schiffer and others that I don't spend enough time with. And then of course my kids are so young

that I still wanna like milk that in a significant way. But I'm sitting a hell of a lot more pretty, I think, than a lot of people. Because a lot of people have also gotten into weird places with the people they love. They fought over money. They fought over an argument. They've cut people out of their lives that they actually love, but it was their own hurt. So I'm incredibly at peace. I'd like to do more. And I think all of us do. Five years ago, when we had a conversation, I asked you what your biggest fear was. And you responded with that exact answer,

which was fear of losing your parents. Yes. This profound impact that your mother has had on you has become- And my father, by the way, real quick. We didn't get there. Yeah. My dad telling me that word is bond might be the single piece inside of me

that allowed me not to be the bad version that some people think I am. The first time I've seen you get emotional recently as it relates to on stage was that moment where you talked about your mother. And I, I was, I was going through, I've got these photos here of you as this young man. I was going through all of these pictures and I was reading how you've described her, especially in recent years. This was my favorite picture here of you and your mom. Yeah, in Russia. Yeah. I've never seen you get emotional on stage before, other than when you talked about the profound influence she's had on you. So if this were, God forbid, the last day you had on earth

to send a message to your mother, what exactly would you say? You did it. She just really wanted to be the best mother because she didn't have one. I would just say she did it. What did she do? She made me happy. You know, I want to make everybody happy. And it's because I'm aware that she did a better job making me happy than anything I've ever seen about anybody and anywhere about anything. And I just feel like if I don't do that,

given that I was given the gift of gab, if I don't scale that, if I don't help every, you know, the biggest thing I can do for her is scale what she did for me. Gary, thank you. Thank you. I have to, you know, I sent you a voice note on your birthday, just telling you, communicating to you the influence you've had on my life. But I've, I'm going to say it to your face, you create a blueprint, which is an evolving blueprint. And I followed the evolution of that blueprint as it's become even more centered on

empathy and kindness and how we treat others clearly that comes from this wonderful woman here um so i thank her for creating a son that's inspired me so much and guided me there's so much that you've done which i've literally copied and i think it's important to say that to you because sometimes people say it to me i've copied your blueprint and that blueprint has changed my life. The thing I wish for you and everybody is I'm incredibly aware of that. And the fact that that makes me happy is the thing I think about every day because it makes so many of our contemporaries unhappy. Amen. I really wanted to say that to your face while I had the chance. We have a closing tradition on this podcast where the last guest asks a question for the next guest. I like that.

Yeah. Interesting. I've heard you talk somewhat about this before. What do you want your tombstone to read about you? He gave more than he took. It's very clear to me. It's been there for a long time in my head. Listen, I have a lot of dreams and hopes for myself. We need to teach people that's okay. That doesn't make you bad. That makes you awesome.

But if you can balance that with also giving just a little bit more in whatever that means. And for me, it's communication and perspective. I'll donate plenty of money, but that's easy. A lot of people do that, that are lucky enough to be good enough at that. I gave more than I took.

I believe in that. You've certainly given me much more than you've ever taken. So thank you for that, Gary. I appreciate you. And it's an honor to spend some time with you. Thank you, my friend. you