Gary Vaynerchuk : How To Buy A Sports Team (Plus Thoughts On Politics, Marriage, and Marketing)

I am willing to punt the next 10 years huge. I am willing to eat shit for the next 10 years.

I believe you.

Thank you.

So go ahead.

So. So I would like for you to poke some holes in my strategy because I want to be having this conversation ten years from now and me telling you what I did differently as a result of this conversation.

Gary. Yes. Good to see you, man. Good to see you. Thanks for hanging out with me. So I want to start, actually, I finally realized something that you say a lot. There's this phrase that I've never really been able to place that you say, and I finally understand what you mean by you have to learn to love your losses. And I've learned this because it's baseball season and I had one of my friends was complaining about the Indians making a, what they call it, like a step back on paper because they lost some of their players.

Yep.

And he said he was basically boycotting the team because they don't look good this year. And I went, when you have those.

Three pitchers, I'm a rotation in baseball. When you have Trevor Bauer, when you have Cleanse, when you have like Carrasco, like you guys are in the mix, period.

Best rotation in baseball. And, and rather than make that point, I said some words that I know you don't like. So forgive me, I slipped. I said, you spoiled millennial. You don. Deserve a World Series. And what's, what's interesting about this is.

How old are you?

I'm 31.

Right. So like, you, like, because you were a fan so early on, like, you realize, like, this is still a very good team in the, I mean, as a 43 year old, this is still an incredible team in the context of Indian lore. Oh, of course, might not be Tomi and Lofton and Manny, but. And Nagy and all that.

But we won the division three years in a row and we're.

I think the Indians could win the World Series this year.

I hope, I hope you are right.

I mean, now I will. Like, when you have three pitchers that look like those three guys, you're in the mix.

Yeah, absolutely. So thanks, Gary.

You're welcome.

So the, what I, what I realized in that moment was it the fact that we are good, the fact that we have the best rotation in baseball is so special to me. But to somebody who's a fair weather fan who has not learned to love the losses in the process, it means nothing to them. They just see a step back. And for the first time I was like, oh, my goodness. I think I know what Gary Means by learning to love your losses. Like, I am so thankful for all of the wins that I've had because of the losses. Not, not in spite of them, but because of the losses.

If You're a hardcore 27 year old Boston sports fan, you've won on most people's eyes, right? You've won all four major sports. You've won five, six with five, six with the Patriots, you've won you, you know, one with the Celtics, you've won three probably now with the four with the fucking Red Sox. And like, what else? Like you have. That's it. No, you don't get the climb. Like, you're talking to somebody who was a Yankees and Rangers fan. They won a championship and I bounced. Like, I actually only like the process of the climb.

I get it. I so get it. In game seven.

How old were you when Renteria got that base hit?

I was seven years old.

You remember it?

Ish. Oh, I remember it. Yeah.

To good health.

Yeah, thanks. Cheers, man.

That was. I mean, Kenny Lofton is my favorite non Yankee of all time.

God bless you. God bless you.

So. Me too. Favorite all but the. At game seven of the World Series when they, when they lost to the Cubs. Even being there now, now, yes, I want a World Series more than anything, but even being in the World Series was like just.

I know we're getting very nerdy. I apologize for everybody listening to the podcast. Four seconds on what you felt when Raji Davis hit that home run.

Oh, my.

It was.

It was a feeling I have never experienced. I genuinely believe that sounds came out of my body that I had never heard before.

Is it true that that is one of the three greatest moments of your life?

Absolutely it is. Are you kidding?

Is it?

Number one, birth of my daughter, Raje Davis. Home run. And probably some things I can't talk about publicly in there. Yes.

For me, the jets beating the patriots in the second round of the playoffs after five, six weeks earlier, they lost. 45 to 3 is the best day of my life. I have two children. I'm married. I'm pretty successful in the scheme of things. I've had a lot of weird, crazy shit. Go my way, number one.

I'm not.

Are you getting in here, Coach? Good.

I am not shitting you.

I know what you're about to say. Admit that you're stunned. It's this good.

I'm stunned. It's this good.

Can I tell you why?

Not like Rose. Can I tell you why I think Rose's fake wine. Can I tell you why this is damn good.

Can I tell you why?

Please.

Something about being a personality and something about life makes people not believe me when I say we made a $40 wine for 20 bucks. Right? This is just like, that good of a. I also made it knowing I know so much about wine. So I know what drinkers like. I know what non drinkers like. I know the collective. What this has is so much fruit that it almost feels sweet, but it's dry. So, like, if you're a Sancer or a Chablis drinker, which is like a hardcore white wine from France, you're gonna like this. It's also just delicious.

It's really. I'm very impressed, dude.

It's crazy how many of my, like, hardcore wine friends or, like, hardcore red wine drink, like, texting me and they're like, look, I bought this because I love you. I thought I would, like, I don't know, share it at a party or, like, give it away. What the hell? Like, literally, like, unlimited taste.

Great work. Congratulations, you know?

Thank you.

Yeah, sure.

And these are the same friends that are like, I don't like your new K Swiss or ugly. Like, they'll keep it real as shit with me. So I know we're onto something with this wine.

So I've got several questions about empathy wines and, like, overall, your strategy here. But before I get there, if I get nothing else, there's one question I'm just dying to ask you. And I really appreciate the fact that you have made it kind of public for entrepreneurs to address the mental health issue, because I think we're all. A lot of us have a lot of junk, and that's what's driving us. So in the last year or so, that's been like, my primary focus is, like, I hit a ceiling in my success. I built and sold a couple of companies.

I remember talking to. Yeah.

And then. And I told you last time I saw you, I felt like I was. My actions were not reflecting someone who was after buying the Cleveland Indians, which is my dream. I mean, I told you, and this.

Is really cool, right? Because something I haven't brought up in a long time. It was my 30th birthday only. You're 31, right? Yeah, my 30th birthday, where I was like, oh, my God, I'm not gonna buy the jets.

Is that when you looked yourself in the mirror and said you're fucking on the highway?

Yeah, like, flat out looked myself dead, literally, on the New Jersey Turnpike on my 30th birthday, driving to work because I work on my birthday. Cause I love it. Looked me dead looked. It was the weirdest thing. I was looking in the rear view because the Jersey Turnpike gets gangster and you gotta be sharp. And for some reason, I looked at myself, it was so instant. And I said, you're full of shit. For the first time. I'm pretty good at not being full of shit. And it was okay. It was actually a very interesting moment. I remember spending kind of the rest of the day and maybe even the rest of the week and maybe even the rest of the year debating if the chase of the New York jets still made me happy. And the answer was actually interesting because the fact that I was questioning it and the answer was resounding, yes. It was probably foundational to me loving all these losses and grinds.

So I have so many things to say on this. But. But for me, it has changed from I used to wake up in the morning and be depressed that I didn't own the Indians and feel like a piece of shit because I didn't know how, I didn't know what I was going to do. And now it's like it's all about just growing as much as possible on the path to buying the Cleveland Indians. And that is like.

I also think, and I know you very little, we've had some interactions. Just in those limited interactions, I think one of the advantages I had, maybe even over you, and I'm asking you this in question form, is you're cooler than me. I'm being really. This is.

Thank you.

It's really crazy how nothing in between the ambition of buying the jets and.

My mental, physical, financial, emotional state at 18, nothing ever mattered to me except being happy. In my process, there was never a time where I needed anything of any kind. And I genuinely believe that the reason most entrepreneurs are not happy is because they've allowed 1%, let alone what I think is really happening, which is 50 to 90% of other variables that money.

Makes happen then status, other people's opinions.

Girls, boys, trips, money, like pictures, like cars, like nothing. Besides, the game has been interesting to me.

I get that now.

It's huge. You're lucky you're so young. That's huge.

Thank you. Thank you. So that's actually where I want to go with this, because I had to do years of therapy, a lot of introspection, sometimes illegal activities I can't talk about publicly in order for me to uncover that truth. Yes, all of the junk, right? In order for in. Or I have to be so dialed in in order for me to think 20% of the time like you, like I perceive you think most of the time. And when I'm really, really, like clear and quiet up here, I hear you very differently interesting than. Than at other times.

That makes a ton of sense to me.

So when I'm really clear and when I'm really good, I know you're right about a lot of things. And I have to work real hard to undo a lot of that to get there.

Less hard than you did a year ago.

That's true.

And it will continue to compound.

So my question for you is, are you a freak who is born this way or is there something you do on the weekends to stay so emotionally and mentally healthy that everybody needs to be doing?

I'm not a freak. I'm outrageously fortunate to have been born this way, parented this way, and the serendipities of my life early on created that framework. I'm fortunate that I took a great blend of the DNA of my mom and dad.

I'm extremely fortunate that I don't have entitlement. I can't tell you how big of a deal that is coming from. Nothing, very little.

I can't tell you how much I genuinely believe adversity is foundational to success. And I got parented in a way that built a lot of self esteem, but not entitlement. And that's where a lot of parents fucked up in the last 15 years. They thought rightfully so let me build up self esteem. You're the best. You're the best. You can do anything. They didn't add the second part, which is you're the best. You're the best. You can do anything. You went 0 for 4:53 games in a row. You're bad at baseball. They didn't add that part. They created delusion, which created entitlement. I got, you're the best. You're the best. You're the best. And when I would make $3,000 at a baseball card show, you're the best. When I.

Didn'T do good at school, like you suck at my parents at my mom at 12:13 started really going into, you suck at school.

So you're not going to Harvard, which means you're not gonna be a lawyer or doctor or get some big corporate job. So you, motherfucker, are gonna work at dad's liquor store every weekend, every summer because your whole life is gonna be working hard. Cause you're not gonna go the easy route of school.

I get it.

Versus what some parents are doing right now, which is their kids are failing at school, they're new wave parents and are like, oh, you're gonna be the next Gary Vee, Mark Zuckerberg. Right. But they're not getting the success in business either. Like all the parents listening right now. This is the most weird thing I'm gonna say. Cause I've been pushing you to stop forcing your kids to go to school and let them be entrepreneurs. Let me throw you a triple curve ball. If you are now a progressive parent with all this new age shit going on and saying, fuck it, you don't have to go to college. Ricky, you're a great entrepreneur because you wanna be, but Ricky's not bringing home money. Ricky might suck at entrepreneurship too.

So you.

I'm like scared of the thing that I'm the face of you.

So you.

Because I don't want any delusion.

So your parents raised you to be incredibly practical because they didn't put any expectations on what would have been delusional is what you're saying.

Correct. And we were only like, immigrants are practical. There isn't a whole lot of ideology when you're just trying to put fucking food on the table.

Did you have expectations of yourself when you were a kid?

Yeah, that I was going to dominate life.

Yeah. Well, I think, I think there's like a, A lot of kids imagine what their life is gonna be like and it doesn't go that way. And they get depressed and that's where, that's where a lot of junk comes in.

Yeah, that's of course, because they didn't realize how much work was part of the equation. It's work.

And you never had that delusion.

No. And I think one of the things that I'm scared of right now is like some people are trying to like, you know, pigeonholed me as like somebody who's pushing hustle porn or like too much work and burnout. And it's just the furthest thing from what I'm saying. But I'm saying a scarier thing than saying overwork yourself is to be delusional. And I'm also saying don't work if you're not happy. And I'm also saying $40,000 a year is awesome. And work four hours a week. I don't give a shit. I'm just saying happiness and self awareness and not living on anybody else's expectations. I'm desperately scared of my popularity growth because I don't want people to try to be like me. I'm an enigma. I know that. How many kids at 6 years old think it's more fun to shovel snow than to have a snowball fight. Not a lot. There you go. And that's why you are who you are too. And that's, to me, the tell. This current state of entrepreneurship being cool, but you were like a bookworm the whole time. I'm cynical. I need you to sell some blow Pops. I need you to shovel some snow. You had to show me some natural cards and rage. And in the same way that Beyonce wanted to dance and sing, the same way Larry Bird shot free throw. Like, there's a reason people are successful at things. They put in the work. It's easier to put in the work when you obsess over it. Like, I'm not good at making post production videos. I didn't sit around on fucking software and think that was like, that's why I'm not as good at it.

And when you're doing something that you're really happy with, you have a much better shot of breaking out into something that is great than if you were just pursuing a result. And I.

Somebody else loves it, which means they'll work harder, which means they'll have an advantage.

When we saw each other not quite a year ago, when we were at dinner with Jay Shetty and Lewis and those guys, I was just at the other end of my.

I remember.

Of my full share moment.

I remember.

And so just for context, I started following you. I was 21 when I started following Gary Vaynerchuk. So it's been 10 years because I saw this guy get on stage at an event and say, I want to own the New York Jets.

And you're like, holy shit, me too. With the Indians.

Exactly. And so I said, okay, this person is 10 years older than me and I think 10 years ahead of me. So I'm gonna start following him and just watch how he places things.

Right. I'll contextualize things, which. That's super smart.

So I didn't know you were gonna break out like you are now, but I've been following you since those days. And I want to tell you what I think I see as your strategy, please, based on watch what you say, not what. Or watch what you do, not what you say.

I'm super excited.

And so. So from what I can tell, and I started to put this together when we were on stage together at the capitalism conference a few years ago. And from what I can tell, your audience and all of the content that you put out basically gives you connections and leverage and exposure so that when you have an Empathy, Wines. So when you have a. A K, Swiss. So when you have a podcast, puffs. Is that right?

Yeah.

Right. So is there any of that laying around, by the way? So. So when. When you. When you've got like the idea or you have equity in a company and one of those breaks out, you can bring all the resources that you have together in order to support that. That. That's. That's what I perceive. And that's.

Right. Let me.

A few years from now, if there's.

A nuances to that. Yes, but there's a huge part of this. When I started putting out content for free in 2009, even with wine. Actually, it started in 2006 with wine. When I did Wine Library TV, I had no intent of selling the wine on the show at Wine Library and that nobody believed. But I think if you listen carefully and I know you have a smart audience for the people that are listening. Let me break it down.

I have no expectation on converting any of the audience I have into anything I sell. I'm being dead serious. I don't convert anywhere close to enough that I deserve for what I give away. Not even close.

I can relate.

We haven't started running ads really heavily on empathy. We're about at 6,000 cases. A lot of it's barter. A lot of people being strategic. That is like massively underwhelming to the fact that there are probably 100,000 people a day that consume my content endlessly for free every day who've already felt. This is just a couple hundred thousand of people who have felt the impact of my free content financially, who have not even bought a three pack for $81.

So the answer is yes. But it happened post game, not pregame. I put out good content for the sake of putting out good content. I built VaynerMedia in 2011 to take advantage of K Swiss or this. I never and still don't anticipate having 6 million people on it. 5.5 million people on Instagram convert, which is actually why I think it works. I'm comfortable asking my audience to like. My whole pitch is very simple. If you wear sneakers, if you drink wine, I'd love for you to consider buying mine versus buying someone else's. But it's amazing. The reason I'm so happy is the value I've brought versus the return on my investment in what I've gotten is a terrible deal. The people that are hucksters that I make fun of, who are just converting their audience from day one. They're killing me in the short term. But I'm not playing for money. I want my audience to show up at my funeral. I mean that. I don't need their fucking money for my wine and my sneakers. I have a marketing capability. I'm gonna sell way more empathy wine to people that have never heard of me than to the audience that has extracted enormous value out of me.

So is the play then, for something like empathy, it was really building vaynermedia. That was the play in order to put something like empathy on the map.

Correct. Or the brands I buy in the future. And I think this is gonna make sense to you because what I just gave you is the 201 of the aha. That you understand of the 101 of me versus a lot of people that look like me. Somewhere along the line you're like, gary's playing this slightly different than the other guys and girls that look like him, right?

Absolutely.

I'm now giving you. And in three years, another thing's gonna happen. You'll be like, fuck. I actually fully believe right now, you believe me 92%. I mean it. I understand it. But eventually you'll understand it 100% only because it's my truth. How much value I've given away, especially the last two years, and how big my audience has become. That's a joke. I should be sold out of all 30,000 cases. I'm not. Because it's not how humans act. Humans do not feel a sense of responsibility to deliver back to somebody. This is why I keep telling everybody, you want to be happy. Give without expectation. You want to be super unhappy. Think you're getting something for your actions. You want to get really unhappy, do shit for the sake of something else happening, which is what everybody does. I watch people game me every day. The problem is they don't understand that I understand what they're doing.

I'm having what. What we call a braingasm here@capitalism.com. and it's actually a bit of a humbling braingasm because. Because my next question for you is I want to. I want to. Wanted to lay out my strategy. And I can sit here and tell you, like, I've been putting out podcast content specifically for six or seven years and written content even longer than that. And my audience is still fairly, fairly small. I have like 15,000 Instagram followers, 75,000 YouTube. So it's fairly humble. But every day I'm recognized on the street by people who come up to me and say, I built a seven figure business because of your free content, the free stuff. And so part of my question is I feel like there must be something a little bit off in the strategy, but immediately after hearing you say that, it was like, actually there's just an expectation there that by me putting out good stuff, I just expect people to do something for me.

That's right. And I think that I understand that that may happen. I know there's plenty of people who bought nine cases, three subscriptions, because they're the kind of person that was like, it's obvious to me that Gary's pushing hard. Let me take a step back. I've literally made $4 million because of this guy. I could probably throw him 2,100 bucks. Fuck it, I'm going to. It's gonna make me feel good. And maybe if I tell him, he'll like my post or make like, I just don't have expectations. I don't know what else to tell you. Like, I don't think it's a customer's responsibility to do anything and I don't do anything. Like, it's funny even the way you say strategy. It's funny what my brain's doing.

Tell me.

My strategy is to not expect anything from these people. You know, like, my strategy wasn't like, I held my breath longer than other people, thus I got a bigger. I think that's what people think right now.

Yeah. Yeah.

If you ask me what I think is happening in the culture right now, you're biting. I think people like, whoa, Gary was just more patient than us. We had funnels and masterminds and products. He was just smart. He waited a little longer, but now he's going in for the kill. I'm not going. There is no kill.

Otherwise I wouldn't have built VaynerMedia. Like, I keep telling people. Like, hey, I understand what you're assuming. Please look at my actions. Like, if I just wanted to, I would have just built my own audience. Like, I would have built 53 million followers. The fuck am I doing running a company that is client service? This is a stupid fucking business.

So I think people, I think what's happening right now is the more mature version. In 2009, 10, 11, people are like, here comes the fucking cliche shit. Then it didn't come. They're like, oh, Gary's doing a little different now. They've seen K Swiss and empathy. They're like, aha. And I'm like, look harder, look harder. No, I think the person who can build a Framework that doesn't look to monetize their audience wins. You know, much cynicism I have for churches and temples and mosques where it's actually just a business.

I went to school to be a.

Pastor, so, like, I look at this, it didn't happen, by the way. You know, I think people look, my thing is like, giving is giving. And asking is that I'm unbelievably comfortable making a post on Instagram that says, if I've ever brought you fucking value, buy three fucking cases. I'm super comfortable. But here's the best part. 24 hours later, when we've only sold 19 cases, after everything, 5.5 million of it, I don't give a fuck. I'm grateful for the 19, not pissed as shit that it should have been 40,000 cases.

Can I ask if you only sell 19?

Yeah.

What do you do to fix that business? Can I pour more of this, by the way?

Well, here's the beauty. The business empathy is built on VaynerMedia. Like, I'm gonna. I'm gonna run ads, I'm gonna do creative.

You're gonna build it like you would build any other business. And Gary Vee gets to be an amplifier.

Maybe Gary Vaynerchuk. Correct. Gary Vaynerchuk built Wine library. There was no GaryVee. People forget Gary Vaynerchuk is building VaynerMedia. If you think the fucking CEO of SAP gives a fuck that I have followers on Instagram when they're writing these million dollar checks, they don't give a fuck.

That's my big braingasm of today.

Got it.

Yeah. Thank you for that.

What's happening right now? And I think you're gonna get it. Cause I've been listening to. I remember very carefully our dinner, and I saw like, I'm like, okay, he's getting it.

I'd love to hear what you perceive.

I perceive that the guy I met on stage to the guy I had dinner with in the club to the guy that's sitting here, is evolving more in the school of me versus going the other way. And I've also met kids that were exactly like you at the time that I met you on stage that have gone the other way. As a matter of fact, I would argue right now in the micro, there's a lot of people running away from my model who've been into me the last year or two because it's hard.

Of course, I think there's a lot.

Of people in the last year or two because I got bigger, are like, you know what I'm gonna do? That held their breath for 18 months, are getting 19 cases and are saying, gary's a fucking loser. I'm going back to fucking like conversion shit.

Well, even you don't have the organic reach that you had 18 months ago.

That's right.

So you don't have the immediate win of taking off the day.

Because I'm worried about tomorrow and I'm worried about fucking forever.

You said something. I will never forget this. Cause it changed my brain. When I asked you, I think you were talking about 137. You were talking about the businesses that you build and acquire and you scale the teams. I was like, gary, how do you manage all of the scale for that? And you're like, well, we don't make much money. And then I said, how are you comfortable just continually rolling all the profits back in? And you said this. My only fixed expense is rent. I was like, holy shit. You have no fear in losing it all because you can. If it all goes away, your only fixed expense is rent, and you're fine.

That's right.

There's no ego in that. There's like no ego in that, dude. When people think, I have to understand how like that mentality.

Because I'm humility disguised in perceived ego.

My personality, my vibes, my energy on camera makes people think I'm ego. My actions over the last 20 years. And the people that know me the best know I'm predicated on humility. I have audacity and confidence and fucking I'm an alpha. But I'm built on the ground of humility and lack of entitlement and recognizing for. Look, I genuinely think there may be a statue of me one day. And I equally know that I mean nothing. Think about that fucking contradiction.

I 100% understand.

I genuinely believe that. I genuinely, in my heart, if I can stay healthy and no tragedy happens that I think I'm up to so much that I think I could pull off a statue I don't know where. Hopefully a real big one that everybody wants to visit. But even if it's in my fucking back, I think there's a statue. I also know from my statue that nobody gives a fuck. Even the eight family members that I have that hold near and dear, three years later, they're gonna have to move on with their life. Like, I believe in that.

There's something in that. And I think that's. That was a very good observation by you. I love it. I was excited to see what you're gonna say. So that was very good. It gives me more competency. You're building in the right direction. You're exactly right, brother. I don't care if I lose everything and everybody on social goes off and everybody throws stones. Everybody. Even people that were my friends. Right. I knew it. Even people that blindly believe in me, then I fail. They don't want to be part of a losing team. Even if they blindly, 100% in their soul believed in me. I fail and they're the first person to jump in, be like, I fucking knew it. Cause they're insecure and they don't want to be part of a losing team. Right. They want to be a Warriors fan, not a Knicks fan. Do you understand? I understand people.

I don't care. Yeah.

In my context, it's like all these Fairweather fans jumping on the Cleveland Browns bandwagon because they're good, which, by the way, you said Baker Mayfield was the real deal, and I was hoping you were right. And now we have all these people who are piling on, bro.

You ready for this?

Fair weather, fans.

I have seen more Browns T shirts and hats in the last. I've paid attention to this. This is my shit. I have seen more Browns in the wild. Not in Cleveland, in the wild. I saw one in Florida the other day. In Dallas the other day. I've seen more Browns. It's so crazy. I can see the guy in Dallas. I was like, is this a real. I just remember walking by him. He was with his girlfriend. I was like, is this a real fan or bullshit? Yeah, man.

And my reaction is like, you don't even know. You don't know what it's been like.

When the jets went to the AFC Championship game in 98, it was the first time they were good, you know, kind of in like 16 years. And I remember, God, this is good wine. And I remember going to the malls. My mom called me and she goes, son, you know, she's, you know, she's like, there's so many Jet fans. I'm like, we're winning, Mom. They're not real Jet bands.

And you know, you know, it's interesting, when the Indians were really bad is when I really bought into the team because I loved watching the process of them building up the young people who mature and do well is so much fun. So much fun. That's why I want to own the team, though. Like, the golding is. Is. Is the fun, like entrepreneurship. Me too. So I would like for you to poke holes in my strategy.

Go.

So. So 10 years ago, I started following Gary Vaynerchuk. Right. 10 years later, I'm sitting at dinner with you right in the middle of my I'm full of shit moment.

Yep.

Right. I've spent the last 6 to 12 months addressing mental health, addressing my mindset, my mentality. And Gary, I feel like. I feel like I'm, if not ready, really close to ready. Like, I really feel like I am whispers away from the next chapter. Yeah, super awesome. Where you were 10 years ago. And you know, it's funny, my dad.

Go to a Knicks game with him. You know, I brought this up and you follow my content. I know my team's heard this when he got me when I was 14, 15, and he was like, you know, it's funny, I always say I'm doing for everybody, but I usually reference my mom. If you listen to me carefully, I'm saying I'm giving to the world what I got, but I'm always kind of leaning more into my mom. And only in this moment, this is the first time I'm ever saying it. Did you just make me realize I'm also doing for people what my dad did for me. My dad took a 14 year old kid who would literally say anything to sell. Let me be very clear, 1989, Gary Vaynerchuk would lie directly out of his mouth. Anything to make a sale. I don't know what to tell you. I would make pretend I actually drank wine when I was 14, which is laughable because I looked 11. I have no idea what those people thought at a baseball card show. If I had something rare, I'd talk about like finding it in an attic at a friend's, like, whatever it took. And my dad.

Hates, hates embellishment. My dad thinks a juicy adjective to a story is like a death blow lie. He's got nothing in him. I'm like, fucking add anything to make it juicier to the story. He's. I could be like. So I came home at 5:45. He's like, 5:43. Like, fuck. Like, that's how much he suffocated it. And I just realized, like, as you were talking, like, man, he's ready. And like, I know you've been watching for 10. Like, to your point, when you're really quiet, I'm like, I can feel it, man. I genuinely believe. I believe this. I believe this moment with me. And I honestly, I know, you know, we're recording this the day after Nipsey was murdered. And it's really hit me hard. And I think the reason I really leaned into that friendship. Out of all the hip hop heads that I've met over the last couple years is there's a purity in him that's so real. And I feel like he was changing the culture, his culture, his environment. And I feel like that's what I'm doing. In a world where there's a lot of guys and I'm gonna go, guys. Usually I say guys and gals. You know how I talk. Let me say it very clear. In a world where there's a lot of guys that kind of look like me and everybody's confused on who's what and what have you. I think I'm doing something right now for alpha winner guys 15 to 30 that will be absolutely, I'm convinced, my legacy. No matter what. I can go on to buy the jets, call my shot for 40 years. And when I go to the ground, my intuition is a generation of men and I affect. Listen, I have a ton of female fans, way more than people think. But there's nothing a lot of guys to look up to that talk about what I talk about. And now it's getting cool because I'm looking at one right now. Now I'm going to start influencing it just like I did in the wine business. When I started doing my wine videos, there wasn't anybody talking about wine like a normal human being. And then I influenced the generation of sommeliers to talk like a human, not like a jerk off. I'm convinced that my whatever the Instagram feed of the day is in seven years is gonna be filled with 26 year old dudes talking that good shit about gratitude and patience and kindness and Word is bond and a lot of other shit. And empathy for sure. And sympathy. Something I need to start using more because I use empathy too much, as a friend pointed out, when it's actually sympathy and a lot of other things. Because I'm evolving too. But I've started the process and I've started it and I know that you know how powerful that feels because there's a lot of people that have been talking about it, but they weren't an alpha dude got it. There was people talking about, I'm not the inventor of gratitude. I'm the first guy at scale that looks like me talking about it in a way that got a 17 year old that wants to fucking dominate think that it's cool. That's a game changer.

You said seven years from now, 26 year olds. Seven years from now I'll be 38.

Yes.

And I Am willing to, to punt the next 10 years huge. I am willing to eat shit for the next 10 years.

I believe you.

Thank you.

So go ahead.

So. So I would like for you to poke some holes in my strategy because I want to be having this conversation ten years from now and me telling you what I did differently as a result of this conversation. So my, my strategy, my thesis up until this point has been to continue to create content for entrepreneurs.

Yes.

And as a result of doing what I've been doing@capitalism.com I've opened up resources and connections with investors, connections with entrepreneurs who are building something really, really cool. And I, I am influencing a lot of people who are building really cool seven and eight figure businesses. People are selling businesses.

Yep.

I could sit here and tell you stories all day, believe it. So my, my thesis up to this point is to continue to do that because it opens up opportunities for me to get in the dirt with those entrepreneurs who are building something cool. And as a result, I'll be a part of something that goes to 100 million a billion dollars and bring in my resources to be able to do that. And then when I have the cool podcast puffs idea that I want to launch, I'll have the audience to be able to at least light that fire. You asked the question. I think this is such a great clarifying question. When people are using kind of word salads, you'll say what do you want to happen? And the things that I want to happen are I want to light a fire that I'm really excited about. Somebody's got an idea and I want to be able to bring the resources, the attention, the investment dollars into that and set that on fire.

Makes a lot of sense.

That's what I want to see happen.

Makes a lot of sense.

I've been doing it for almost a decade. Let me give my audience.

Let me.

Give you a comp right away. Let me give you a reinforcement of a real life example. Marc Benioff Salesforce multi billion dollar valuation often says that Tony Robbins helped him on his path. Tony had a very different model in the 80s and 90s. But in theory. And forget about self help. And like, you know, I've always kind of like you're very tact, like it's funny. I want to be tactical. People think I'm a little too up there. I'm like fuck, just watch what I do. That's the tactics. And then listen to what I'm saying. Cause if your operating system's right, then you can do the tactics. You know what I mean?

If you give to your audience who are then capable of Building 7 and 8 figure businesses, as long as you eliminate short term wants and needs from them, you will give yourself disproportionate leverage to own 11% of Facebook, to own 7% of Tesla. The vulnerability is when you want to light your podcast puffs on fire. I think the most important thing happened here today, which is I told you that it doesn't convert very well and that's fine. Which means that you're then playing what you need to do. If you really want to follow my model. My audience.

Is never going to be the source of paying for my livelihood.

Understood?

The end.

Understood.

This is where I laugh at what people think is going on with me.

I know you have to bounce, so I let's do a speed round.

Cause I know there's a lot of things you thought about and I'm really enjoying this and I'm gonna fight for every minute.

Appreciate that. So I'm gonna give you your choice of answering one of two very, very easy questions. I know you like trends and you're pretty good at predicting them. So number one, and you know where.

I stand on me predicting. I think I'm very good at moving very quickly. So I'm not predicting. I'm communicating what has already been proven to me. I don't guess.

Understood. So without guessing, I want you to tell us what's going to happen in the 2020 election. And I want you to tell me the future of marriage.

That's a very interesting question because that could. Those two questions could only come from somebody. They're not actually layups. I'll tell you. Let me like, let me say this out loud. Those two questions are disproportionately.

Smart. If you follow me carefully. I never talk about politics and I've been alluding to what happens when the world becomes super transparent. Because I'll answer number two. I think marriage is a super interesting debate over the next 20 to 50 years. Here's why I believe this to be true. I believe that the shadows of our society, infidelity, prostitution, strip clubs, have been massively important to the current state of marriage because they've given an outlet. Let me say this very clear to both men and women. And by the way, no question, because of hardwiring. 85% men. 80. I don't know the data, but I live in life. I know many women that do things that are not popular, that are alphas.

So nonetheless, it provided cover.

It created foundational pieces that in a world where nobody can hide. I'm curious what's going to. I'm curious if people are not. I think there's a lot of people who got into marriage over the last hundred years that knew themselves and said, if I needed to be sexual with another partner, I can do this. Because I do want to be married and have kids who now are going to think I will get caught and I don't want that scarlet letter. So I need to debate this to begin with. And I think that will be a hundred year thing. And I do think marriage is in a very interesting spot in the next hundred years because I do think lack of privacy will lead humans to adjust to it. I don't know where it goes, but if you ask me if I'm a betting man, in 50 years, are more people married today or less? I would say way, way, way less. Doesn't mean people won't have. I think you'll see people go through what we see with divorce. This is why as divorce's stigma went away, it went from 10% to 60%. I think you're gonna see people have a lot of. I think the modern person 100 years from now will probably have three meaningful relationships in their life lasting eight to 15 years each.

I think our mutual friend Aubrey would agree with that.

This is the way he stands. I'm gonna see him soon, so I'll ask him.

You're coming to Austin, right?

That's what I was gonna ask him. I think Donald Trump's in a very much better position than most people think. I think he's high as far as electability. Yeah. I think he's gonna get more likely reelected than people think. I do think that Joe Biden could beat him.

I hate talking about politics, even though. So I have very many views. I'm outrageously socially liberal, which makes me struggle with a lot of the GOP point of view. I think it skews too much towards hate at times. I'm also super scared of like. And I don't think it's. I think the socialism thing is laughable as somebody who came from communist Russia. But at the same token, like, I get DMs from 22 year olds that say, Gary, you're rich, you should pay 90% taxes. So I should get money. I DM back and say, I'll give you 100,000 right now personally. To which then they're like, what are you talking about? I'm like, I don't think you getting. I don't think people that don't want to work and don't have talent, can be successful regardless of how much money I give them. And as long as every other person that makes as much money as me pays 90% taxes, I'll pay anything.

Do you think that this is. That there will be an end to the two party system in the next few elections? No, I don't think so.

Not in the next few. I take longer view than that.

Yeah. Okay.

It's more to marriage. I believe we're seeing the beginning stages of a four party system in America in the next 50 to 100 years.

Interesting.

I think you're gonna see the left and right. Right now I'm unbelievably comfortable with the extreme of the left and right, which has not been hist. Where I sit. Which makes me feel like you'll see a middle for both.

Absolutely. And it feels three.

I think it's four, I think a left middle and a right middle.

That's. That's interesting.

I feel like a Republican and Democrat party of 1980.

Yes.

In 20.

I feel like it's faster than that. It may be, but, but, but that's.

I also think that America's in a funny spot where it needed to pay the Piper in 2000. This is funny that the. Both the Republicans and Democrats bailed us out in 08. Both Bush started it and then Obama finished it, which I love because then both are responsible.

They're both guilty.

I think the great undermining of America, if there ends up being one, was that we didn't pay the Piper in 08.

Fuck yes.

I'm sorry. I was an economics student during the crash and everybody was saying we needed to bail them out. And I was like, all we're doing is punting it for 10 years and we're punting. I thought we were going to have like a big meltdown way earlier than now. We continue to punt and we continue.

To do that which creates really bad behavior.

What is the source of that? I say the Federal Reserve and low interest rates. What is.

I don't know.

Okay.

I love that I got to say that I've been waiting for a I don't know moment. I just got one. I don't know. I'm not a macro. I'm not educated enough. What do I really think? Collective softness at the highest levels. If I was the President of the United States when this all went down, I would have gotten on TV and said, we deserve this and we will get through this, but everybody bunker down and eat some fucking shit.

God bless you.

Because that's how you win. That's how you win. You don't win by fake environments. Everybody's so mad at these parents that paid for these kids to get into these colleges. That's what we did as a macro government for the whole country. We should have paid the piper.

Amen, brother. I'm gonna leave it on that one, Gary.

Thank you, bro.

Thank you, man. Thanks for having me.

That was fun. I believe that your trajectory with me and what I'm listening to has given me confidence. I mean, this I believe the kid at the stage, and maybe even, to be frank, the kid on the stage. No way. The kid at dinner, I'm like, ooh, I'm intrigued. This dude that's sitting in front of me right now. Anybody you want me to meet? I feel comfortable because I don't think he's going to me. Hucksters.

Hot damn.

So it's my email. Me and Tyler, boom. Me and Alex, boom.