Self-Esteem and Confidence Building with Steven Bartlett | #4 of 2024 Top Podcasts

29:59I 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 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 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.

30:43Self-aware hair. Self-aware hair. The tortoise and the hare. 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, 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 room, 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.

31:21People 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 front. 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 VFriends. Nobody has a clue, including my inner circle of how much thoughtfulness I did in character development.

32:00This 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 podcast. 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 too ambitious, it's the reason they're listening. So self-aware hair 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, V friends.

32:44And 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 should 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.

33:28Lean 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?

34:12watch 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 vicanti 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 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.

34:47You 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.

35:23And so back to your point, we are gonna 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 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.

36:00there's a lot to your point there's a 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 100 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?

37:32They 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. 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 a good call out that may bring value instead of what I just said.

38:07Asking what you're in it for is humongous. Yeah, but 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, young guy. That's how I know. But I know too, but guess what? 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 too. 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.

38:42We've been putting on makeup since we had fucking clubs hitting each other. It's what humans do. We do things to communicate. to - 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's status too though. I want to be the most leftist. I want to be the most on the right. I want to, 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.

39:18It's another thing when you're trying to make someone feel bad about themselves. That's why the acts of us collectively at eight 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. 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 it's got to stop and i think it 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.

40:48I 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, I want to change the world, Gary. Yeah, of course. And then you go, well, what do you want to change about it? They go, I, 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. The problem with all the things I just mentioned is they're a vulnerability to your own happiness if it's not balanced.

41:21By 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 cars 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.

42:03That system's broke. It won't work. I mean, I don't know what to tell you. 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 three million dollars a year, 17 million dollars 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.

42:38An 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.

43:17One 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. I'm hypothetically. 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 shit gets crazy.

43:55You're describing me there. So I, at a very young age, only black kid in an all white area. We're also the poorest family. So we understand the value. So you had all the advantages of adversity. Exactly. Yes. In 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 go off into the world, I'm convinced. My subjective evidence is if you get the material success that 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?

44:32Hold 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 much that might not be enough because those first 10 years as we learn in childhood psychology you're 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 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 do you understand in America in 1968 in 1971 in 1971 In 1971 in America, if you were an astronaut or pilot, you were cooler than an athlete.

45:39I want everyone to fucking pay it. 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? Yeah. Do you understand? 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.

46:2730. 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 we managed to get seven-year-olds absorbing content, which I imagine is probably a lot of your plan with VFriends, that is empowering, that is creating new evidence in their mind.

47:06Purple, not red or blue, right? Back to what public it, purple, right? Like competitive clown is a motherfucker. Accountable aunt kids is the thing. Like if you lost, you fucking lost. I don't want to overcoddle 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.

47:40My 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?

48:24All 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 in. I'm trying to say that any early experience is going to be - Yeah, yeah. Could. Any experience from between the age of zero and 10, I think - Could be a major factor, right?

49:00And I've sat here with these childhood psychologists and therapists like Gabor May, who studies childhood trauma. In that first 10 years of your life, if your parents are constantly - I believe in that. Crying your eyes out about money. I believe in that. 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 yeah 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 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 of there's a layer between what happens and their interpretation.

49:47Right, because we overreact in both directions. It's your interpretation. That's right. And that's what the childhood psychologist said to me. That's right. He says, you can, there's what, it'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 regarding that person who grows up in a household where they interpret 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 going to, because for me, I just can't imagine a world where that was so deep inside me, that insecurity and shame.

50:20I 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 they're somebody and get an assistant to reply like I'm still in it and in that I see it.

51:16There'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 gotta play it. And as someone who's not good at poker and has won many hands with three seven 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?

51:57Yours 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.

52:37Billions, Steve. There's been billions of alternatives of the exact opposite. it. 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, 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 difficult It's Star Wars It's all Star Wars What's your dark side?

53:31Probably 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

54:09of course of course Steve there's a little ha ha but if 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 Minikawa 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? Not because of like the great place you're going with this path.

55:01Like 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 going to 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.

55:49That's winning in a different way though. 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 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 twelve 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?

56:52I 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 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.

57:31For real, no bullshit. I didn't, 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 this is 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 it 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.

58:16It 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. 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.

58:55When 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 I don't you play basketball at all? No? We play pick up 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 11-1 everyone's natural internal inkling is to like, let's reshoot for new teams.

59:43Mine is this deep excitement to get the other four people together looking at everybody's face and say, guys, we're fuck, like immediately, I'm 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 outthink them and most importantly we're gonna 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.

1:00:16But 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 this you're going through an introspective moment clear in your late 20s 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, even when I was getting admiration for it, 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 does that matter 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.

1:02:20I 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 sour pussed in the last stage of their life.

1:03:03America was fucked up when we all got here. It was a real recession in the Carter years. Queens was fucking Queens back then. 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, other shit.

1:03:34I 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 fucking studio apartment. And you know, I get that. But you were, so the question, which I'm sure you've had level it year 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, 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.

1:04:14So 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, 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 I should have taken more vacations in my 20s with my buddies 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 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.

1:06:02Actually, 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 Warnieke. 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 Schiffer and my second cousin and my dad.

1:06:38And 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 asked this for very, as if the cameras weren't here and the microphones weren't here. I'm earlier. I'm 30 years old. 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. On that, as it relates to that family and that personal piece, what I might get wrong. Because I know - So I don't think there's wrong. I think somebody watching me might say, you're doing this wrong.

1:07:16I might watch you and say, you're doing this wrong. 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.

1:08:08She has been wrong, she's been proven wrong, and so what that did for me, you know, I put my mom at the highest pedestal, is, oh, me judging Dustin or Steve, like, I'm gonna 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.

1:08:49That 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.

1:09:26I 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 want to 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.

1:09:58So 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. 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.

1:10:33And 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 - 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.

1:11:19What did she do? She made me happy.

1:11:31You 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.

1:12:11Gary thank you um 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 gonna say it's your face you create a blueprint um 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's 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 um i like that yeah um interesting i've heard i've heard you talk somewhat about this before what do you want your tombstone to read about you he gave more than than he took.

1:13:24It'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.