Nice Guys Finish First: How to Maximize Joy Over Money

29:18I'm like, dad, you know, I'm gonna be 73, God willing. You know? So, my brother, on the other hand, was 11 years younger. I was his hero. I was as much, if not more, a father figure to him than even my own father was to him. I had already accomplished a lot, so he, you know, So I came into that partnership with a lot of emotional and experiential and results equity with my brother. And my brother, to his credit, we started the company 50-50 equity-wise. We didn't know. We didn't know how it would play out. But we looked at each other and we promised each other, we don't know how it's gonna play out, but we will adjust our entire careers to how it plays out.

29:59And to his credit, the way it played out was I was, and he will say it, much more significant impact than what the business became and when we started VaynerSports, even though he was running it full time, the equity was different in my favor even though he was running it and everything we've done subsequently, we have an - We all know families aren't easy, particularly, I mean I work with my husband so I say this to you as somebody who has familiarity and I really enjoy it and I'm grateful for it but it's not easy. No, it's not easy because you're blurring lines. It sounds so easy all of a sudden.

30:28My brother and I have had it easy. I'm being very, my father and I had it incredibly challenging, yet wildly easy in the macro. It is, I mean, I wish it on everyone. And we really had a lot of arguments and had a lot of tension and had a lot of moments, but my gosh, and I'm sure not lost on anyone in this room or anyone listening, as you get older, the time you spend with your family increases in value, and all the other things you worried about decrease in value. and I cry, back to crying, I'm getting a little emotional now. I had a very interesting moment. I think it was my junior year of college.

31:06I called my mom one day out of the blue and completely broke down and said, mom, because basically since I was 15, I'm like, I'm coming into the family business. I'm going to build a monster. And I wanted to build it for my parents. I wanted to. I was so grateful for them. I had that nobleness, superhero syndrome and I knew I would have more time. I knew who I was. doing VFriends, because you really always did want to be a superhero. 100%. 100%. And I was raised to be a superhero. I don't know if I always wanted to be a superhero. My mom made me a superhero. You know, again, my mom was very affected by her upbringing.

31:39You know, at the time I was seven or eight, nine, 13 years old. My mom was an immigrant mom who lost her mom early and my dad lost his dad early. And she would say things to me of like, to my face, you know, this is my hero. If anything ever happens to us, you have to take care of your brother and sister i will say though as a kid again right i have a younger sister seven years and there was always that sense because you're the eldest that's right of this of like if something happens it's on you so i mean there was the yeah sense of incredible responsibility of an older child is a thing it's a thing and i just brought it up earlier because it's the thing i'm most working on in my lab right now my head this early adulthood late adulthood you and i had that and and I'm gonna say it again, I'm poking at this zit for everyone who's listening, because I know what's going on with a lot of parents that have 25 year olds.

32:27There's a lot going on right now. I get all the DMs from both of them. You and I had that, and we have 29 year olds where mommy and daddy are picking up the phone 13 times and taking care of everything financially and emotionally. We have a problem. And a lot of what the world's upset about and that's going on has to do with that. Not social media, not other things, the just sheer lack of adultness and lack of self-esteem that we have in the younger generation at scale. Many are not, I'm not generalizing, but shocking amounts do. So anyway, that's kind of where I was at. Sorry. Yeah, I call my, oh, I'm sorry.

33:00Yeah, I know. Don't finish your story. Thank you. I never, I never do. And I'm just bawling to my mom and I said, mom, I don't know if I want to go into the store. I don't know if I want to join the liquor store after college. I feel like this was a moment of potential insecurity. I'm like, I think I'm going to be one of the great businessmen of all time. I've got all this stuff, but if I, you know, dad's tough, like, you know, and he's the best. I mean, I wanna make sure I'm painting a very clear picture. My dad, in his, you know, my dad's a cact. You can love him and he can still be tough. I'll tell you exactly who my dad is.

33:29He's a cactus. He's super, you know, tough on the outside, but inside it's mushy, which is why he has the cactus. I know it all, a lot of it. Anyway, nonetheless, I really broke down. I didn't wanna do it. If I go, I'll never get credit for who I am. Everyone's gonna be like, your dad, you know, and all this stuff and it was just one day, it was a 20 minute conversation. I moved on literally the next day, I'm sure my mom, I don't even recall what my mom said. I just remember how I felt, I'm sure it was lots of encouragement and you know, that's kinda how my game played out. But my dad and I, 80 % of the time it was wonderful, 20 % of the time there was real contention.

34:08Hard to leave? When you get that choice? No, no, because my dad wanted it too. let's talk about the other side of the story. My father comes to this country with 100 bucks. He works his face off every minute to have his own liquor store business. He's an old school man. He's the man. Here comes his son. And son starts to work around the store. First he's just happy that the son's not a schlemiel and can contribute. Then all of a sudden he looks around and five seconds later his son's 23 years old and everybody that he's had a business relationship for 20 years has no interest in talking to him and they only want to talk to his son and his son's the boss, not him.

34:47Yeah, not so fun. So I'm incredibly compassionate to like how that must have felt. So now, and don't forget, now I built a monster for him. So now we're one of the most powerful stores in the country. Wineries from France are coming in to kiss the ring and do a deal and like we're as hot as hot gets. We're the kith of like wine retail to put it in street wear terms and now I'm willing to walk away and he gets all that power, he was hyped. He was also... So you had no sense of guilt? I definitely had no sense of... Are you kidding? Do you know what I just did? I just got paid$50 ,000 a year for 12 years to build a$65 million business for my dad and I'm giving him all the power which is the only thing he actually wants right now.

35:28I felt like a hero. And my dad was naive. You know, I always like to razzle... He can do it without you. That part. My dad rewrote history and I get it out of pride. In fact, the greatest thing that happened to me was the decline of the business in the next 10 years finally allowed me to get what I was looking for, which is my dad giving me a hat tip that I... I like that for you. You know, that was, oh, that was, I mean, when my dad asked me to help... That had to have been so difficult for him. I still can't believe it happened. That, you know, I can believe it happened because I know where the business was going and it was starting to get a little weird.

36:01A lot of those people who would have just... Died on the ship. You know, my dad is a die on the ship. You know, the good news is, the truth is, actually, I believe if my father and I did not have a good relationship, he would have died on the trip. The good news is we have a great relationship and we're really close and I love him the most. And so I don't think it was that hard for him. Okay, so let me pivot to your brother leaves and you know, one of the things I realized is you're in a lot of different businesses. Yes, I am. Pickleball, V Friends. Yes. Right, a lot of things. And as somebody who also has a lot of interests, I worry sometimes about prioritization.

36:35Like how can you put, right, when you were focused single-mindedly on that wine business, right? Versus having like to share your interest across six things. I joke now I have six jobs. It's very hard to be good at six jobs. How do you think about that? Easily. That is such a lie. It's really not. In fact, I had a meeting yesterday with my comms team. There's some business magazines that want me on the cover, which is humbling. And they asked me what I want on that cover. And I said, I want it to be a a picture of me juggling nine balls with three of them falling, and I wanted to say the juggler, the untold story of Gary Vaynerchuk's business life, because to your point, even people that know me well have no idea that I have a flourishing TV and production company in Vaynerwatt.

37:20I have a restaurant group in New York City in Vegas and now New Jersey that's crushing called - A private club. A private club called VCR and Fly Fish Club downstairs. I have seven to 10 alternative sports investments, pickleball, wiffleball, unrivaled the women's basketball league, many many the sailing league I'm really deep in alternative sports I have a 2500 person VaynerMedia that people know VFriends people are starting to get know more and more I still quietly run the wine business through my best friend and we do wine text I have a lot going on let me tell you why the answer is easily okay I ask you in return what's your KPI what's your ROI what are you trying to achieve I am trying to maximize joy okay say more because I want to hear about that.

38:04If I wanted to maximize money, someone's argument of like, you should prioritize, would hold more weight with me. Do I believe that if I spent every minute on VaynerX or VaynerSports or VFriends or VCR, that that thing could go and one could argue, definitely VaynerX, VaynerMedia, that if I put 100 % into that, would I financially do better than spreading it out? The answer is, there is a path for me to believe that. That is just not what I'm trying to achieve. I want to wake up tomorrow morning and be excited. And what excites me is doing a lot of things. I like potpourri. I want many things.

38:45I do not want one thing because I want to enjoy myself. And when I go deep into something, and I do, I can go three months where Vayner eats up every minute. The fact that I can step outside for a second after that and go play here or go play there, that is my joy. That's what I want to do. so I don't struggle with prioritizing. What do you think drives the curiosity to learn? Because that's really what you're describing. I'm inherently wildly curious. You nailed it. That was a real aha in the last five years. I'm like, oh shit, I'm wildly curious. The end. I think what's driving me is I'm very creative.

39:19I'm very curious. These are not the obvious things of Gary Vee. I've got all these elements to me. I just, I'm into it. There's a term that you hear oftentimes in sports, other areas, listen to your body. right, in medicine, I'm very good at listening to my soul. I'm very good at listening to my body. Mary, this might make sense to you based on the vibe of this combo. Sometimes I'm like, man, I wonder if I'm just gonna wake up at 62 and be like, you know what? I'm moving to Peru and I'm gonna live on a mountain with a goat. Like, I will listen to my body to the end. And if that's what I wanna do, that's what I wanna do.

39:56Okay, so for people listening who are like, I'm not in touch with my body. What are you saying? How does one get in touch? I think it's different for everyone. For some people, it's therapy to unblock something. For some people, it's exercise. For some people, it's going on a heavy acid and shrooms trip. I don't fucking know. For some people, it's forgiving people that they're mad at. That's one. Let me go down this path for a second. Okay. I believe forgiveness is the answer to the quiz that many people are struggling with right now. What does that mean? I believe the dogs can sense I'm going somewhere big.

40:33I think they can feel it. That's the mailman. That's fine. But I think it was more that they, you know, they have a different sense. I think they know where I'm going. The dogs are like, what's happening? Here it is. I'm giving the big answer. I believe many people are fully clogged emotionally, are unable to be self-aware, in tune, connected, because they are holding enormous resentment and anger. Sorry. Is forgiveness let it be or let it go? or is forgiveness a combination of candor, like actually saying your piece? Yeah, I think both. I think forgiveness in the way that I'm describing it now is to actually call someone that you've not talked to and tell them that you forgive them, or even more powerful, forgiving yourself for something that you know you did that was completely inappropriate, illegal, whatever it might be, because you're in a different place now.

41:26I think forgiveness is a wildly underutilized, not talked enough about action and trait that I wish more people, what I'm doing right this second is desperately trying to get through to one person listening to this podcast to pick up the phone and call their mom that they haven't talked to in 20 years or go to the mirror and say, it's okay, you were 19, you were a different person then. I just think forgiveness is underrated. So, you know, one of the things that's interesting is I listen to you, right? I always learn as I interview people, which is part of the reason I think I like doing it. You know, we started this thing called The Longest Table, where we put the table down the block and invite neighbors to Pollock, and now over 2 ,000 people come.

42:11And oftentimes when I'm in industry with people we know, everyone's like, why are you not growing it? Where's the hockey stick? Have you monetized it? Like, what's happening? It's literally the immediate reaction. and when I say, well, that's kind of not the goal. The goal was to try and just connect neighbors to each other. I mean, of course, I'd like there to be people so that we're not three volunteers trying to band-aid it together, but the goal wasn't money. Right. And it's very confusing to people. Not to me. I would even, I mean, if we just want to go there, I'll go there with you. Like, I'm not even sure any of my business behavior is attached to the money.

42:54I just don't see it that way. My first chapter of my career was to give back to my parents. And the second chapter of my career is to fulfill my interest in play. And my play is building businesses. Some are to cook and some are to paint and some are to surf. And my play is to build businesses. Did you ever feel, so I buy that, but on the flip side, you know, as a kid who also had financial insecurity growing up, there was a sense of also having to pay my bills. Like I didn't want collection agencies to come bringing up my doorbell. Makes sense. I had something very good happen, which was I never even knew of a concept of not living within your means.

43:36Yeah, I never believed in borrowing money or credit card debt, so I relate to that. I literally thought as a grownup I would not have a credit card. That's how anti-credit card, and I also have another thing that really works in my favor. I don't care if you think my house is shitty. So basically it's like, I just didn't think about money that way. I always thought I could make some because I was good at it, right? Like when you're making 500 bucks in 1987, which is like a trillion dollars when you came from nothing. Literally in 1987, in 1988, I'm making 300 bucks at a card show. 10 years earlier, my family has 100 bucks to their name.

44:13So very quickly, my talents in this capitalistic USA, I knew that I could, but more importantly, I never was scared of that part. Money didn't drive me because I knew that if I made, if I made 50 ,000 a year, that I was gonna live a$35 ,000 a year life, and that's that, so what am I scared of? Okay, so here's some of the predictions I read, okay? Death of the smartphone, interest media versus followers, social shopping, brands starting their own AI influencers, So basically owning IP and AI optimization versus SEO. Those are just some of the ones because you love making predictions. And I know sometimes they're right and sometimes they're wrong.

44:56I mean, that's the nature of predictions, I suppose. But one of the things that struck me as I looked at some of these predictions was that do you think that some of these will leave the world lonely? That's a great question. I am very in belief of the conversation around loneliness is another version and another topic in our current society that continues to miss the point of accountability in modern parenting. Okay, what does that mean? That means it's very easy to not be lonely in today's world because of technology. And it's very easy to be lonely in today's world because of technology. I don't think the technology is the driver of loneliness.

45:41I believe that the way we are holding people accountable, the way we parent, the energy of the way the human journey is going is a much needed combo, for example. Loneliness is also being communicated because we now talk in the world about our feelings in a different way than we used to. Right? I think we can all agree with that. Now, I think we've come a great way in some ways. I think it's super awesome that it's not 1967 and every single person on earth has every feeling in their stomach and no one can talk. On the flip side, we live in a world right now where people literally, so we really track this stuff at Vayner, where people literally in their social have been out four nights this week and on Saturday will post a tweet and be like, I'm lonely.

46:33Now, I don't think going out means you're not lonely because you could be in your head lonely, but I think there's a lot going on on this issue. I believe that digital is the gateway drug to being less lonely. people meet on Instagram DM and on Tinder and then go out and have a date with each other the technology's in place for us to be less lonely I believe the self esteem issue is why people are lonely and I think that is the big conversation I'm it's not that I blame technology I'm not saying you do when we do the longest table one of the ways we let people know to come to the longest table is by posting on next door Correct, of course.

47:14Of course. In fact, we do storytelling. The way tables have happened around the country is because people have posted stories. And so let's break that down. Okay. And then someone's on the other side and sees that and they decide if they're going to go outside. Yeah, or decides to host their own table, by the way, which is what's happened. Correct. So for me, technology is an enabler. It's the exposure. Right. It's the great exposure. But. People stayed home and watched PBS and read books in 1984. I will say, I do think there's a difference. Because I think when I was in middle school, as the outsider kid in middle school, if somebody was having a party, I had no idea because I wouldn't know.

47:54I was in my home wondering where everybody was reading a book. It's not true. How would I have known? Because I love you with all my heart. I think you knew. I didn't. You might have not known a play date, but a birthday party? Yes. Okay, yes, a birthday party. But I wasn't also sitting at home like watching them all gather. Yes, but you know what you would do today as a 14 year old that wasn't invited to the party? You would go on Twitch, you would go play video games and find your friend that lives in Cincinnati. There are many people who use technology to create more friendships. I guess where I'm saying is I think it's a net neutral.

48:29And I think the combination of how we talk about everything these days is a factor. And two, the ones that continue to struggle with loneliness, there's the enablers around them. Parents have always been enablers. We've become remarkable at it. By the way, I have a 16 and 13 year old. Like I'm not pointing fingers. I'm talking about things in the general. You know, yeah, I mean, I'm not scared of AI making us lonelier. I'm really not. No, I'm not. I'm not saying you are. I'm just trying to answer the question. But I go back to you have teenagers. Yes. So how are you parenting differently? Than what?

49:11Than what you say most society's doing, which is causing these problems. I'm trying to communicate to them when I think they're going into patterns that may lead to what I deem as insecure mindset. So when my son, after a basketball game, he's very good, which is probably why I'm bringing it up. I love bragging about it, like every parent. When he looked, even though he's actually very damn good, and it's crazy to me he's this good, when he looks for excuses that I just watched were not true, I won't let him get away with that. He'll be like, Kenny didn't do that. You set up. One of your rules, no complaining.

49:46It's, you know, listen, I think we took it too far in our family because then we didn't talk about feelings. So I think everything, by the way, everything we're talking, by the way, last five minutes, everyone, everything's about purple, right, if anything, I hope. Actually, it's all about gray. Yeah, exactly, it's the same thing. I use purple now because everyone's locked into blue and red and I'm like, purple, purple, purple. All of this is purple. There is, you know, when I'm like, I really, you know, a lot of times when I'm like, this is what's happening with AI, it's because I'm trying to give another context point to what I watch the masses lazily leaning into, like, this is all gonna be bad.

50:17I'm like, really? Because that's what we've said about everything. You know, like, the tractor. Do you know this? Like, we all worked on farms. The tractor's invented. that everyone's like, everyone's gonna be out of a job. We went on to do bigger things. Like we, I promise you on the record, I can't wait for this to be played in 100 years when I'm long gone. I hope they have a party around this clip. We are about to go on to much more remarkable things because of AI. Now I'm not, I'm not doing - I'm not saying you are. I'm not saying you are. I'm gonna agree with you. Which I know is shocking.

50:52No, I, not from the way I view you. I actually think we see things similar. I think the world is gray and what I worry about is how most people feel so certain in their conviction about things. The more I know, the less I know, and yet I feel like people are just so convicted about their beliefs in ways that I really can't believe. My thing about practical optimism, which is what I think I'm spewing, it... If you hear noise, it's the dog. Yeah, it's awesome. Where I'm at with practical optimism, I mean, I had a great dinner last night where we really got into it with a group of six people. I'm like, okay, I'm going on history with context.

51:29you're saying it's over. My question to you is, if you actually believe what you're saying, you better change your behavior. If you think it's all ruined and it's all wrapping up here in the next 10 years, why are you not going to the airport right this morning? Like, why are you going to your job? This is what I said to the people. I'm like, where the fuck are you doing? Are you going to work tomorrow? This is literally when I went with my chest. I'm like, are you going to work tomorrow? Yeah, I'm like, the fuck are you doing that? You just told me in 10 years it's all over. Dad, it's all over.

51:55The fuck are you doing? So I just think that people love to wallow in negativity. I think we're a bunch of hogs moping around in mud. Woe is me, this sucks. Pointing fingers to everyone. Here's a big one. I just need to get this off before I'm out of here. I want to ask you a question. At what age is it appropriate for you to decide you're a grown-up and stop blaming your parents for everything in your life and realizing you are now a grown-up and you can do actions to mitigate the pain you're feeling. What age do you think that is? That happened to me when I was young. I get it. I'm not asking you or me.

52:33In society. I actually think you have to do that at any age. I agree. And I'm giving forgiveness. What age do you... Respect. I actually, on a show the other day, because we got hot on this, I went with 25 because I just decided to give a couple more years of grace to kids. Oh, that's when you're... Yeah, exactly. I like the fully developed. I like the fine, like I'm trying to find some, you know what I mean? I was like, but fuck man. I'm around unlimited 30 and 40 year olds, all they want to talk about is what their mom, they tell me the same story 400 times. I'm like, I know you. I'm like, I've been your friend for 25 years.

53:09I remember your mom. I know what she did. The fuck are we doing here? How much do you want to fucking slop in this slop? We're fucking slopping and slop. All right, we're not gonna be slopping and slop here. Okay, we're gonna go with her. Don't you worry. Rapid fire. Okay, biggest miss that still haunts you? I don't struggle with regret, but the biggest one that everyone knows about is I passed on Uber. Travis was my best bud. He's the only person I mentioned in my first book, Crush It, outside my family. We were that close. I did something that I don't believe in, which is scared money doesn't make money.

53:45I just bought my first big boy apartment. I had very little in savings that was comfortable to me. he came to his credit he came back a second time he's like bro how could you not be in i just fuck and that fifty thousand dollar check would have been five hundred forty million dollars so that one didn't work out okay one piece of advice you now think was wrong that's a great question uh you're like i just gave one i just kidding i've i i often back to candor i often told kids when i was growing up to find relationships that were easy you know like it has to be easy. And I realized that was me avoiding in hindsight conflict.

54:24And I think that led to less authentic relationships at times. And so luckily I stopped saying it by the time I made content publicly. So there's not a lot of videos of me saying, I don't think there's any by the way, but I will tell you the real answer because I want to be vulnerable and real and I hope this helps someone. My historic advice that I gave in my 20s and early 30s before I made content or when I was only making wine content to my inner circles and the people that would listen to me was relationships should be easy. And that's not true. Relationships should be real. It can be hard.

54:58Okay. One sentence your mom would say about you. He has a golden heart. I like that one. He's a superhero. She always said you have a golden heart. And that mattered to me. That's what I wanted to aspire to. What advice would you have for someone who needs to pivot? that that staying in the thing that you're in is worse than if the pivot goes catastrophically wrong um advice for a recent graduate so much um get off mommy and daddy's payroll at all costs at all costs live with nine friends and eat garbage food get off of their payroll at all costs number Number two, 22 to 30 should be nothing but high risk, high reward behavior, because you'll never have a framework that's that easy to go after your dreams, and you've gotta scratch that so you don't sit with regret on the back half of your life.

55:53Those two stand out for me. Okay, if you're gonna try to be a content creator today, you would? I would deploy self-awareness, figure out if you like writing, if you like Gift of Gab, do you like being on camera, do you not? Content creation comes in many forms. I'm loving the rise of Substack. I'm so happy for writers. I won on the rise of video because this comes natural to me. But I can't write for shit. All my best-selling New York Times books, audio. I literally have to audio. I have to talk my way into books. So be self-aware of what medium you like and then understand that volume of content is not subjective, but the quality is.

56:31What does that mean? It means that people do not understand how important volume is. Oh my God, you know who does? You. Yes, I do. And I would say that understanding the distribution of our day, which rewards volume, and understanding that is this good is completely subjective. Is this, do you guys like my sweater? Do I like that? I love that photo action. Jesus Christ, that's awesome. You know, like most things are subjective. The amount of output is not. And a lot of people from our world love high fidelity and production value and their opinions. And so I think that holds a lot of people back.

57:10I can't thank you enough for coming on. Did you have one final question, Andy? Back on the self esteem thing, and we'll let you go in for a second. Jets jersey, Jets sweater. Oh yeah, okay, you've told the story about your mom and the Jets jersey. I know you still wanna own the Jets. Yes. We're gonna - Pray for her. For you. She knitted you a Jets jersey, and I know you prized that. First of all, what was the number, who was the player on the back? And I think it was five. Pat Leahy was number five, the kicker at the time, but that wasn't why I did it. I did it because five was my favorite number when I was seven.

57:43I think because I decided my favorite number when I was five, and since I was five, it became my favorite number. I don't really recall the origin of that. Yeah, it's the most emotional story of my life. Every kid in the neighborhood had a Jets jersey. We're playing Nerf football all the time. I'm infatuated with football. I would argue that American football was my coming to America, my Americanization moment. Mine was being a cheerleader. There you go. So you get this a lot. It's very young. We're playing every day. Everybody has a Jets jersey. I want one. I asked my mom. The answer is no because immigrant families don't buy$20 Jets jerseys.

58:20And unbeknownst to me, every night my mom knitted me, similar to this actually, a jersey for me to wear. And did you wear it? Or did you not wear it? Because you were like, oh, it's not like everyone else's. No, I wasn't. You just spoke. No, yeah, I wasn't embarrassed. I didn't think it was worse. I wore it proudly all the time. And that actually says a lot about you. Yeah, it was there early. You know, to your point, I haven't thought about that. Like my ability to tune the outside, my mom said I was the best and I believed her and there was nobody outside the door that was gonna tell me otherwise.

58:54And that's my life. That's a perfect place to end. Gary, thank you so much for coming. Thank you. Hey everybody, if you enjoyed this podcast, please go back and look at the prior episodes. They're loaded. I appreciate your attention. And thanks for being part of this journey. See you later.