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Being a Great Operator Is My Biggest Vulnerability | Gary Vaynerchuk

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About this episode

“I had to come to a hard realization in 2024. Me being such a great operator is my biggest fault.”From the transcript

Your operator strengths might be the very thing holding you back. Gary Vaynerchuk shares a hard financial realization.

Gary Vaynerchuk is known for spotting internet trends years before they happen. But even with that foresight, he faced a brutal reality in 2026. Sometimes, the skills that get you to a certain level of business growth are the exact same habits that prevent you from scaling further.

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In this episode, I sat down with my GOAT, Gary Vaynerchuk, and he did not hold back. Gary broke down his entire empire, from VaynerX and VeeFriends to Vayner Sports and his new TV production company, and explained why he refuses to follow the "just focus on one business" advice so many of us preach. He opened up about building Wine Library into a $50 million business for his dad, walking away at 34 with nothing, and growing VaynerX to roughly $400 million in revenue without a single outside dollar to start. We got tactical on where attention is right now, including TikTok Live, Substack, Facebook, YouTube Shorts, and Snapchat Spotlight, and why he calls this the era of "interest media." Then we went deep: why being a great operator is his biggest vulnerability, why he has no one he goes to for advice, how he runs his companies like a family business, and whether Gary Vee is actually happy. This one is packed with real advice you can use today.


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Being a Great Operator Is My Biggest Vulnerability | Gary Vaynerchuk

The Entrepreneur DNA

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The Entrepreneur DNA — Being a Great Operator Is My Biggest Vulnerability | Gary Vaynerchuk. Machine-transcribed; use the interactive transcript above to jump the player to any line.

Who does Gary B go to for advice? I had to come to a hard realization in 2024. I mean financially brutal realization. Is that a nut? I'll bet. Me being such a great operator is my biggest fault. Gary Vaynerchuk, one of the world's leading marketing experts, entrepreneur and investor, a New York Times best selling author, and is one of the loudest voices on the internet. Gary Vaynerchuk has been telling people what's about to happen on the internet, about three years before they're ready to hear it. Here's a data point that's not subjective, it's objective. There are more millionaires and there's 20s right now than ever before. So everyone crying in Gen Z that we don't have opportunities. What about your contemporaries who are crushing it on social? The way I think about businesses, employees first, customer second, me third. Is Gary be happy? I... So why is social media no longer social? I think it's just voyeuristic at this point. Well, it's not social because the term of social meant your social graph.

Your people would follow you. It was always voyeuristic. Yeah. It's always been the same. The reason it's interest media now is the algorithms benefit good content, not people with followers. Which should make everyone listening intoxicated. Yeah. Because now we have no more excuses. That's right, no more excuses of like, oh, I missed it. Gary Vaynerchuk, you've been doing it for 20 years. I'll never be like you. You sure will. Yeah. Alex Earl was unknown three years ago. Drake, this is a little down for me. This is my own curiosity. Yeah. Vayner sports, Vayner media, VaynerX. VaynerX is a holding company where Vayner Media... So VaynerX's marketing is a marketing production, is a production media creative marketing company. Within it is VaynerMedia the crown jewel. Two other junior main, but soon to be equal VaynerMedia's Chuck Media. Which used to be known as Sasha Group. I rebranded it. So now like my whole last name is in there. VaynerChuk, Chuck Media and Tamara Group,

which is named after my mom. And then Gallery, which is a publishing our purewow.com covetour and then the speaking bureau VaynerSpeaker. So that's VaynerX. Yeah. Outside of VaynerX is VaynerSports. Because my minority investing partner in VaynerX is Steven Ross, the owner of Dolphins. And he can't own any piece of a sports agency by NFL rules. So AJ and I had to put VaynerSports outside of VaynerX. Then there's VaynerWat, which is something I've just started talking about. Which is a three year old TV production company with my partner Eric Watt in Berg. So VaynerWat. So you'll start watching Netflix, Hulu, Amazon shows in the next year or two. And in the beginning, see that logo VaynerWat. So we'll be spending more time in Hollywood. The restaurant group, the wine store, the alternative sports investment. I was on CBC last week. My with a ball ownership. We just won a World Series. Pickleball. Thank you. Pickleball. Unrivaled.

The three on three women's basketball. The sailing league. Like we're, we're, meanager building a very big portfolio of alternative sports investments. Yeah. So pretty active in that. My personal brand, you know, the content and all that is an entity in itself. Of course. Do you actually have it like as a true entity? No. I have a personal LLC, which it might interact with at times. So, you know, quite a bit of stuff. All of which, you know, I'm very active in. Yeah. And so I'm definitely, I go on this rant early on, not for bravado, but more to create permission for the entrepreneurs that are listening who want to do more than one business in a world where a lot of the entrepreneurs we look up to tell you to focus on one. I was going to ask, how do you do all that? Because I would sit here. So I run kind of a consulting team for businesses, small businesses.

I would tell most people to say like, if you don't get focused, yeah, you're going to, you're going to, you know, screw the pooch here. I think there's a little bit of Bo Jackson, Deon Sanders in me. Okay. I just think I'm actually capable of doing more than one thing. Like, there's just the truth. So there is a level of like, and by the way, on the record, it's nothing to do with me. My mom and dad had sex at the right second and gave me DNA that allowed me to, so I do think that's true. And just like Bo and Deon, like, it's hard to do that. It's rare. So I do think it's rare for someone to be able to meaningfully run, you know, every business I just mentioned, every one of them does over eight figures in revenue. These are all ten all of that. I mean, and we didn't even get into defense yet. That do you understand? I do. I do. I do. That is why. But I also don't think it makes me special. What I think is special about what I'm doing and why I'm intoxicated of still doing podcasts like this is I'm not trying to maximize dollars.

Explain that. Well, I'm not so sold that all these eight businesses are actually maximizing my financial upside. I think back to your advice, I think if I want one hunt, we didn't even mention V friends, which is getting a ton of my attention. It's my Pokemon Marvel Disney business. I mean, it is so cool. This is for my daughter, by the way, I have a five-year-old like one of my favorite things about friends is it's a massive girl dad brand. Two of the five hottest characters in our universe is fearless, fairy and ambitious angel. And so anyway, I believe if I went 100% of V friends or 100% of VATER X or 100% of Vainer sports or 100% of DCR group or VaynerWat or Wine Library, that there's a chance I would make more money. And you don't care, not because you don't care about money, because you just have more passion than other, you and rather do it. Yeah, I got these NFs in school because I, from so look, I've never done anything about money. From 22 to 34, I gave 100 hours a week to my parents,

left with nothing. You know, sometimes people try to razz me in comments with all the content. And they're like, don't listen to him. He inherited his family's wine business. Not only did I not inherit it, I built it. I currently do not own any of it. My father owns all of it. And I gave up my greatest youth years. Yeah. You said you exited at 34, 35? At 34, I left. I definitely didn't exit shit. I left the business. And started VaynerMedia and started it in a conference room smaller than this little studio we're in with my brother and three of his friends because I had no money. Yeah. Right. And so, and so you should go start a business with the whole money? How old are you? 45. Right. Think about 34 years old, not having a, literally not having any money. Like did not have enough money to pay a lease for a couple thousand dollars a month, because what had happened was I did save up a lot of money. Even though it was making 65, 75, 80,000 a year when I was 25, 29, 30.

Sure. I was living a 24,000 dollar year lifestyle. I had a shitty apartment, buy the liquor store and did nothing. So when you don't do anything and you don't spend any money, you can save. And right before I started VaynerMedia, I had invested all my savings into Facebook and Twitter. You literally went for the moon like... Moonshot. I'm going for it. Going for it. By the way, it was $200,000. It wasn't like it was a billion. It's everything you have. But it was everything I had to your point. And I was 33 and I had resentment built up because I built up a $50 million of business for my dad and he wasn't paying me anything. And his answer was, you'll inherit this when I die. And I'm like, Dad, we're 22 years apart. You have great genetics. Like, I'm going to be fucking 74 when I inherit this shit. So that's why I had to leave. Because I wasn't in control. But I was okay with that because I knew what I was doing from 22 to 30. I had no problems from 30 to 33. It was starting to build up. I'm like, fuck, I'm getting fucked here a little bit.

You did have a little bit of that. We know. Yeah, I don't. I've studied you as much as any like you don't talk about. No, because I don't want to paint my father in the wrong picture. Of course. Because I don't think it was so much his fault. I think every immigrant that's listening that grew up like with a gas station or a deli knows in immigrant families, not American families. Yeah. Like the mindset is you give it all to the business and you inherit it when you're old. So I don't think my dad was trying to fuck me. But I definitely started feeling some sort of way. The business was doing 3.8 million when I started running it. Now I'm working 120 hours a week every day. Did you and your dad have this conversation where you said, Dad, I'm getting frustrated. Me and my dad fought tirelessly. We had many arguments about not really that part that started to happen later at 30. Okay. What we thought about was just like how we treated our employees, how to run the business like day to day shit. But yeah, from 30 to 34, there was a four year buildup of me being like,

fuck, I'm an AJ was also coming. My brother's 11 years younger to me. Okay. At this point, he's 19 when I'm 30, he's going to college. And he's like, I'm not fucking working for that. I was going to say where you're like, bro, you got to get in your arm out. No, I wasn't mad. I was like, I thought when he was 14, bro, get in here. We're going to do this. Oh, okay. Bro was smarter than me. Bro at 15, at 15 was like, bro, I'm never going to fucking work for dad. So I knew in back of my head for a while, like, oh, shit, if I want to be a business with my brother, it's going to be have to be outside of one library. But anyway, going to the point, I've made no decisions on maximizing finances. And if my financial team was sitting here, they'd be like, yeah, he's an idiot. Like, he doesn't maximize against taxes. He doesn't do safe shit like real estate. And as if he's like, I'm just living for joy. Yeah. I'm not scared of going backwards. I'm not scared of the judgment of the entrepreneurial community if I lose it all. No kidding. Real talk, brother. We don't know each other like that. I'm telling you, you look at Trains Body Language.

Yeah. Which like, I, all the propaganda I put out every day of not listening to anyone, it's real to me. Like, okay, like what? I'm not living for the cheering in the comments section. I'm wildly humbled by the way you started this podcast. Like, the warmth is like real. Like my goat, are you kidding me? Like, look, I'm literally even getting goosebumps. Like, that's insane. You're my goat, bro. But I'd be okay with disappointing you by like losing everything because I'd hope you'd learn from whatever the fuck I did to go to that. By the way, does that make sense? I view myself as a proxy to the game. Sure. Selflessly to the game that gave me so much more than the selfish things the game can give to me. Yeah. Okay. I'm not in the game of entrepreneurship for a yacht. You know this about me. I've never posted anything bougie. Never. Ever. Like to the point of like, come on, buy yourself something nice. Yeah, because for me, nice is I already bought it, which is on Janality.

Oh yeah. I don't want a 13th home. I want what I have, which is, I'm going to do whatever the fuck I want. How do you do it? So let's go to that. How do you have time to do anything? I mean, I literally people. Yeah. One of the things I'm great at is developing relationships with my employees. Okay. To me, the way I think about business is employees first, customer second, me third. I think one of the biggest reasons so many people here are not winning is they want what's in it for them first. I'm going to start this t-shirt business because I'm going to make $4 million and I'm going to get a million followers and I'm going to hook up with a bunch of chicks or a bunch of guys or I'm going to go on shopping sprees. I, I, I, my brain is like, what's in it for train to work with me? Yeah. And then I'm in it for like, what's in it for someone who buys V friends, right? I hope I bill on Walt Disney and that one day they'll wake up in 19 years. They might have bought it for their daughter, but one day in 19 years they might go in the attic and be like,

this is worth $4,000. You know, like I think about that a lot. And then if all of that's true, if train has an incredible career and makes lots of money, if you and your daughter have a collectible that's worth $4,000 from a box, you bought for $300 one day. Well, if those things are true, well, then I fucking really won. You won. Like if those things are true, then I really won. And so my selflessness with relationships with other humans is actually the ultimate selfish card. It comes natural to me. I do naturally think about other people. But the reason I'm winning is let's break it down. VCR group, David Rodelitz. David Rodelitz is the active CEO and operator. I am definitely his like right hand in thinking, supporting. Sure. You know, the NFT restaurant was a brilliant move. It really worked out. By the way, if you all remember years ago, my NFT restaurant, it's fucking crushing. It's called Fly Fish Club. You know, I'm there for those big moments to think through stuff, to support with Vayner X

supports our restaurants really well, because we have a lot of employees in Manhattan. So why does VCR group work? Because of David Rodelitz. Vayner Y. Eric Womburg was 20 years at CAA. Was a big dog at Wheelhouse, which does a ton of TV shows that did really well. Like, why is Vayner Watt working? Because of Eric Womburg. I'm there to like sell a show, to be the magic at times, to star in Sheddy's. I got a, like if anybody goes on Delta right now, look up Wine Game. Like, I'm in that show. Watt did that production. He asked me to be in it with Carmelo and Chef Andres. Why does Wine Library work? Because of Brandon Warnicki. Brandon Warnicki is there day to day. I'm his thinking partner, but he's in the trenches day to day. Why does Vayner Sports work? Because AJ is a fucking gangster, right? So why does V friends work? Because I'm the one, in those businesses, I'm the one B or two. Yeah. In V friends and Vayner X, I'm the one edge. I'm the guy. But Andy Craniac and John Troutman,

my right and left hand, and May knew, like there's a lot of people at V friends. And then Vayner X, JT Kaelin, ultimately at the highest level, Mark Yudkin, my general counsel, like my true, like if we were a mafia, my true confidate, you know, like that was the boss, like Yudkin's taking that walk in the backyard saying, are we Wack and Johnny? Or are we not like, he's my guy, right? Like Anthony Lattino, our new CFO, he's been my brother's best friend. One of my brother's best friends since they were six. He was the number two in finance for the last decade. Like, you know what kind of peace of mind it is when I have a $400 million revenue business, and the CFO is someone who I remember pooped his pants when he was six. So family business, like whether they start his family, like Marcus Cresastic who runs international for Vayner X, who was also Anthony Lattino and AJ Vaynerchuk's best friend and first grade and they were three musketeers. Do you know what kind of peace of mind I have about Singapore? And like what I do is I convert people into family,

JT Kaelin, Mark Yudkin, Eric Wattenberg, David Rodelitz, or it starts his family. Brandon Warnocky, 14-year-old best friend, AJ Vaynerchuk, my actual brother, you know, Anthony Lattino, Mark Yudkin. So to me, the reason I, like ultimately, if I always thought that my autobiography was going to be called the bridge because I pull from very opposite directions, competitive fucking gangster will slice your throat, but I'll love you to the death. And like, you know what I mean? Yeah. But even like sitting here, I'm like, huh, I wonder if I should, my autobiography should be called Family.business. Because I think it's family business. Mm-hmm. I mean, I do something I've never done with podcast because you're so prolific. I'm actually going to read some quotes that I love from you and I want you to do a deeper dive. Okay. But before we go there, you put out a book about two years ago. Yep. Day trading. Attention. Attention. Two years, a long time, social media. Yes. What has changed from that book two years ago to today?

Everybody go to GaryVee.com slash attention. It's a 50 page deck that is the sum up of that book. I'm even saving you 20 bucks of buying the book. Buy the book. Get it. Buy the book. Buy 10 of the books. The book is still incredibly relevant. Thank God. No, I agree, by the way. Uh, which I'm shocked. Actually, I'm shocked by that. Usually it moves too fast. Here are the updates that are not in the book. Live shopping and live streaming are the two biggest changes. No kidding. I would tell you, you, you, you, you, you, the number one thing you should do every morning is go live on TikTok for an hour and just talk to the random people that show up on the screen. There's no place that gives you discovery. Like TikTok live. Instagram live. You go live. It pings all of, as you know, it pings all your followers. Yeah. And they come on. And if you're not entertaining them, they drop off. You lose half your audience immediately. Yeah. And it's all people who know you. They follow you. Yeah. So you get TikTok. That's right. TikTok. You go live. You just randomly show up in people's FYP. And that's how you get discovered. It's the number one brand building.

It's the number one mistake I'm making right now of not doing it every morning. I need everyone to rewind that. Write the second. That is the best game because my next follow up question. The book is very relevant. Today though, I think you just answered what platform, for growth, for attention, for awareness, for. Yeah. No, no. Back to the book. I said it's shockingly relevant because so much changes. I can also argue it's not as relevant because it changes so fast. So we've got TikTok live going live. We'll get to live shopping. So Justin Colby has to go. Justin, you hit with some guys we want to go talk about whatever. Yeah, you're like literally live. And the way I would do it, just in case you're looking at the screen. And you're like, yo, I'm an entrepreneur. I help small businesses. Let me tell you what's on my mind. Had a meeting last week with a guy with a car wash. Where he's fucking up is these, his expenses are at a whack or his customer acquisition or Google adwords is not working anymore because everyone's going to chat GPT and clawed. Yeah. And so the SEO game. And then people are just listening to you. Yeah. And then like Johnny Pants 49 is like, wait, tell me more about SEO

and you're just interacting with them. Not presenting. Yeah. You're presenting interacting. That's it. Substack. Okay. So I'm incredibly bullish on Substack. Which, do you know much about it? No. I could tell by your reaction. I'm excited. Yeah. You got to look at it. Are you a writer or no? No. Okay. Funny. English major at UCLA. Not a writer. Need the same. But I have a team that transcribes my words in podcasts like this into writing. Yeah. So Substack is a massive newsletter platform that's starting to be a newsletter slash Twitter ex massive. Next, Threads. I don't use it. It's happened. Real fucking sucks is a gangster. It's happened. I myself am like pushing myself harder on threads. Threads is like a weird Twitter alternative. Like it's there. No kidding. Yeah, it's there. I don't use it at all. Twitter's gotten better too long form on Twitter, writing like three paragraphs on Twitter, doing five minute videos, posting on Twitter, Twitter, continue ex, continue to grow.

Now everyone's so concerned these days with growth. Yes. You know what you didn't mention is Instagram. I lean heavy on Instagram. You might say Justin, you are. I love Instagram. It's an incredibly important platform. The reason I didn't mention it yet is my assumptions. Everyone's on it. And my knowledge is that everyone's over-dependent on it. I agree. I'm one of those for sure. So the reason I don't bring it up is because I know all of you have already focused on it. I think it's become most people's vulnerability. I would argue that people have become over-reliant on Instagram and TikTok in pop culture, influencer, business. And that YouTube shorts, Facebook blew the classic Facebook. I love Facebook, by the way. Facebook's a monster. If you're not making content daily for Facebook on here, everyone, you're making a massive mistake. Facebook, you know, like a fan page, like the classic brand page.

Snapchat spotlight for people under 30 that are trying to target people under 30. Excuse me. Like me, I'm not under 30, but I target under 30. So Snapchat spotlight. I don't even know Snapchat was the little thing. I gotta shoot just like I'm like, once DJ Calab left, you're like, if you go to Snapchat, right? If you go to Snapchat, there's a part of it that is literally, as you can see, just like Instagram. But like, look at this person's data on the right. Like there's a lot of people. Wow. Yeah, like basically Snapchat has its own and look at the data on that. Look how much interaction. That's insane. So literally just posting it. And that's nothing. That's not an influencer. That's not Gary Vee. There's some random, well, that's the other thing. All these algorithms now, everybody is on the same plane. No matter how many followers you have, if you make good content, you can get four million views. That's the big innovation of where social media is now at, we're at interest media, not social media. It doesn't matter how many followers you have on your social graph. It matters how interesting your content is. Someone listening right now, who's never been on Snapchat's spotlight, who wants to break out might,

on their third post, because they've been inspired by me with four followers on Snapchat, might get 40 million views. That's intoxicating. I don't know how that doesn't get everybody up at night. And to make content on all 10 platforms. LinkedIn, YouTube shorts, these are monster platforms. So the biggest thing going on right now, in marketing, is everybody's a one or two trick pony. Yeah. When they should be posting at bare minimum, which I hate that they do this, but I'll take it, post the same fucking video on all 10 platforms, and I call it a day. Even if you use one of those companies, that goes, yeah, which I don't love, because you're not maximizing the nuances, changing the wording a little bit, because as you can imagine, under 25 year olds on Snapchat, versus what you would post on LinkedIn, there's going to be a nuance difference. Of course. But you can make the same video and post it on it. Maybe you change the first three seconds. Maybe you change the headline. You definitely change the copy that you support it with. This is so great. You've been known to say,

patience for me is macro. Tenacity is micro. You have to be tenacious at the task at hand, but patient in the overall mission. I would argue one of the most misunderstood things about me is that I talk about like, oh, you're 40. Like a lot of people like to take jabs at me saying, oh, fuck. How old are you? I'm 50. I'm saying what I make content. Hey, you're 40, you have time. Yeah. A lot of other content creators like to razz on me on that. They're like, I love Gary Vee, but he always talks about 50, you have time. He's wrong. You have to fucking, like go hard now. No one goes harder than me. No one. No one. 14 active businesses, and we're 12 hours a day minimum. Yeah. When I talk about patients, or like you're 34, you have time, friends, I'm not saying lay on your couch and jerk off all day. Yeah. And like, I'm talking about, don't use the fact that I'm 28, and my life is over. If you believe that, your life is over. Yeah. Have a good relationship in the macro about life. But go fucking hard day to actually achieve what you're crying about.

So I think people miss that when I talk. I've said the fifth law of success for me is removing your time expectation on the result you want. 100%. That's what that's my way of saying the same thing. That's my point. Yeah. Well said, and that's my point. Like, and again, my point is also choosing optimism over cynicism. Like it's not very complicated. If you think it's over at 43, if you're brain, if you're soul, if you're talking to yourself and saying, I fucked up, I've married the wrong girl. Yeah. I fucked up. I should have went with those buddies on that startup. I would have made so much money. I stayed in the safe. If you're looking backwards, how the fuck are you gonna, like you're gonna lose. You're gonna run into a fucking wall. Break your neck. Like, my point is that if you've decided it's over, it's actually over. I actually don't believe there's any truth in life. I just believe there's perception. Okay. Just believe your life is like how you see it. Like I don't know. Like I think the world's great.

Yeah. I have a funny feeling. A lot of people listening here. I think everything's fucked right now. 100%. So I don't know. Like that's what I mean. Yeah. Like my perception is that yes, there's a lot of things fucked up. But this romance of the 90s. I love when I was like the 90s had it so good. The 70s had it so good. The 40s had it so good. Friends, did you know how much fucked up shit was going on? 100%. We didn't see it because there's no social media. Yes. And because you know, like inflation and separation of wealth. And like I understand what everyone's complaining about. Let me make it very clear. Here's a data point that's not subjective. It's objective. It's black and white. There are more millionaires in there's 20s right now than ever before. So everyone crying in Gen Z that we don't have opportunities. What about your contemporaries who are crushing it on social? Mm-hmm. Why would someone need to go to social right now? Because we just gave a macro look of all the platforms what it could do. If you don't run a Gary V. style business. If you don't try to get clients, what would be people's needs to be on social?

Well, if you don't have a B2B or a B2C business or you aren't interested in building up your profile so that you can get brand deals, your NIL, your name, image, and likeness. If you're not trying to sell something which is B2C, right? Wine, you know, V friends. Or you're not trying to do B2B. I'm on LinkedIn all day because I'm trying to get Coca-Cola, BMW, American Airlines to be clients. For VaynerMedia. For Vayner. So that's, you know, I'm not, VaynerMedia doesn't sell to these people. Right. It sells to Fortune 500 companies. So if you're not selling to the world stuff, if you're not selling B2B or you're not trying to build your NIL, right? I am building Gary V because I get paid $350,000 to give a one hour speech. Right. That's absurd. Insane, by the way. I can't even believe I said that out loud. So I'm monetizing at all three levels. NIL, right? I signed seven, eight figure book deals. I get paid six figures to give one speech. I get offered millions of dollars and tons of equity

to be in business with businesses like Stan and others. Yeah. NIL, I do B2C clearly. Like everyone, please go to vefriends.com and check out my collectible universe. And then I do B2B. Yeah. All right. If you're a Fortune 500CMO, please go to VaynerX.com and, you know, fill out the forum and let's have a meeting. If you're not doing one of those three things, I have no idea why I can fuck someone's on social. So for example, you know this about me because you know me well. I don't put out my personal life at all. I was going to get there. I, in fact, how about this? How about I got a curveball in a hat for you? If I wasn't doing what I'm doing for a living right now, I probably would not have a social media account because my interest in gossip, in voyeurism, in rubber necking, in being a yenta, in knowing what my friends vacation is zero. Zero. My, I interact with my friends on text and phone calls and over dinner. Yeah. Yeah. I interact with my friends on,

now listen, real talk at 50, not a business, maybe I would have a Facebook to see like, to, I'd go once every six to eight weeks to see what my high school friends are doing. Yeah. NIL, let's bring up NIL, which I don't think a lot of people thank you for explaining that. I'm one of those people that argue personal brand over company brand. Yep. You need to brand Gary V before Gary can go launch VaynerMedia the way it's been. I, I think it's and I would argue, I understand what you're saying. Yeah. And I'm a very bullish. Look what you do with, uh, case-wiz. Rather, I wrote Crush in 2009 that makes this argument. I'm with you. Yeah. That being said, I do think you can do both. And I think it can go both ways. Melanie Perkins built Canva. Okay. And then built up her personal brand. And Canva is a multi-billion dollar company. Yeah. So like, I think you can go, you see what I mean? Yeah, yeah, yeah. Look at Elon and Zux. Yeah, but businesses were built for sure. I'm just saying, I'm just saying, Sarah Blakely, Spanx was built before her brand.

Yeah. What I'm saying is it's aunt. And you can pull up either at any time. Yeah. So you could be Gary V for four years, NIL monetized and then start a business off that equity. Yeah. Right? A serial brand or a sneaker. Yeah. But you could also build a business that's doing the grueling CEO who just sold his company for a billion dollars to Unilever. He can now decide if he wants to be a personal brand. Right. Right. Right. Stephen Bartlett built his brand. He's building a ton of businesses against it. Yeah. Right. But like, Cody Sanchez was doing business. Now she's building her personal brand, which will create more businesses. What I'm saying is it's very, I'll use fighting. Okay. It's very left and right. It's good to punch with both. Another book that you may have. Yes, jab, jab, jab. Right. You brought up Stephen Bartlett. I've been podcasting 13 years. He has done something so special. I mean, I'd watch him and I go, what do you think he has or what he's done that separates all of us? Right.

Like I might be in the top 20. He's number one. He acts like this is what he did. This is what Hermosi's doing. This is what Alex Earl, Alex Cooper, none of you invented it. None of you were first. This is not a game of first. Yeah. This is a game of best. The reason I've done really well is I've been early and good enough. Right. Yeah. Yeah. But they should all these people, you know, Logan Paul, Charlie, Demolite, everyone should intoxicate everyone in the audience right now. What has he done? He executed. Yeah. He executed. I mean, he's just crushing it. I watch him and I go, this is brilliant. No, he's very good at what he does. Yeah. And like, like, but again, why can't people? Like I keep telling people, this is sports. Like, what did SGA do? He was just good at basketball. He didn't fucking invent basketball. He wasn't the first to play basketball. It's a great analogy. You know what I mean? Yeah. It's a great analogy. What did Michael Jordan do? He was just maybe the best ever.

But he wasn't first. Right. Will Chamberlain and Magic Johnson and Larry Bird. These are all just games. Yeah. And people come along that are better at it. Yeah. It's better to be fast than to be perfect. Speed is four billion times more important than perfection. I'm so glad I just went off the sports rant to this. Speed in sports is an crazy variable. If you are fast and basketball for fall baseball, ten, like, it's one of the key elements. Yeah. I believe that is true in business. I believe the reason I win a lot is I go fast hard. I don't overthink things. I'm not fearful of the loss. The reason people don't go fast is they're scared to lose money. I mean, I mean, do you ever start a business that just goes, now that didn't work. I mean, I did a side project slash business called Vayner Toys where I've said I really wanted to garage sale and flea market my whole life. I watched that whole thing. So, yeah. So, I really, there was a company called Vayner Toys that I kind of stood up that failed.

There's a lot of divisions within Vayner Media, Vayner Live, Vayner Sampling that have failed divisions. If I'm the one A and I'm like driving, if I'm doing only because I don't do things that are, I don't overextend myself. You know, you're... I know myself. Yeah. I fight within my... Like, if I was a UFC fighter, I would have been one of those that like, I mean, listen, in fighting, anything's possible. But like, I feel like I would have been one of those people that never got knocked out. I don't do the things that... But I'm aggressive, right? Some fighters are so defensive. They don't get knocked out, but they also lose their fights. I have a good mix of being offensive and defensive in business. And business is easier to pull off than fighting, because one shot and fighting it, it's over. And I've definitely been surprised in business, so maybe those would have been the shots that knocked me out. I just think that a lot of people that are watching right now want to be like people, but they don't realize that they're... They're pusses.

Are you an operator? I had to come to a hard realization in 2024, and it, I mean, financially brutal realization that I'm not the fucking operator. Do you want to know the craziest thing of all time? Me being such a great operator is my biggest vulnerability. Really? Because you want to get in... I should... I'm too deep. Yeah, yeah, you want to be in the mud. I'm very COO at VaynerX. Really? Yeah. Because I mean, obviously, as a new friend, but like I'm watching outwardly, and you're just 30,000 feet above everything. Don't forget my narrative. I built Wine Library. I built VaynerX. Bro, from zero. That's right. VaynerX is going to do 400 million dollars of revenue. From zero. Like, not valuation, not investment, $400 million in sales. This year, like, we will charge clients, $400 million, $385. Like, we'll see where it ends up. I built that from zero. How do you start that? So I just had this conversation, Ryan's her hand. He didn't take on any money. He literally said, I went and sold. Yeah. I took my money on my pocket and I said,

Yeah, that's what said. You say him. So when you're a salesman, that's what you do. No bank, no debt. Now, maybe that's changed for you, but initially it was just... Never went to... To this day. It's all self-hanging. Yeah, well, we got that investment from Steve Ross. Four years, five years in, but we took every dollar off the table. AJ was very young and wanted to like jumpstart his life, get his house home and all that. And I just took it and invested in startups. So, yeah, this business comes from zero to 403, 380 to 400, depending on where we end this year, all on self, all on the, you know, the NHL paying is 500K. Me servicing it for 380, having 120,000 of profit and putting it back into the business. Who does Gary Vee go to for advice? No one. But that is not a strength. Yeah. That is not a strength. That is a weakness. But it is the truth. Who do you rely on to protect your downside? Like literally, like, whether it's lawyers, asset protection lawyers, tape like, do you have all this? Do you go out of this sucks? But I built something impressive.

Yeah, I mean, I, again, I brought up Mark Yodkin. He's my true confidant, my legal, you know, I've got Anthony Latino as a CFO now. Alan Harker did a great job for almost 10 years before him. You know, Ted Byer is like a gentleman. I use all my personal finance stuff, but it's, again, I'm not doing any, like, I'm in the business of making money. I'm not in the business of managing my money. Hmm. There you go. You understand? Yeah, yeah, absolutely. Like, that's how I did. Yeah, tough to be s- Like, I'm not on defense, bro. Yeah, you just keep going. Like, I'm just creating wealth. I'm creating things. I'm building things. I'm not protecting a lucky moment in my career. How, uh, from now side perspective, my interest in sports cards has increased since COVID. You and Michael Rubin, were that friendship start? We met, you know, we were coming up the game and different. I feel like you guys like, because I don't know him at all.

I feel like you're the same. We have a lot of, yeah, we're back. There's a lot of, we have a pretty close friendship there. There's a very close friendship there. I mean, I've spoken, I mean, I've spoken to him four times in the last week. Yeah, we're very close. We met in, you know, I remember, I remember once 15 years ago, maybe more at a, at a Dr. Oz party up in Bergen County, New Jersey. We had a nice little app. I think it started to get more serious our friendship in maybe 17. I think it was maybe 15. I think in 2015 was the first time I told him he should buy tops. Look where he's at. And so, uh, and then, and then we really got close to our in COVID. Okay. He called me, we had kind of started hanging out every six months, maybe in 15, 16, 17, 18, and then 19 was COVID. 20, 20, 20. Yeah, you're right. March 20. He called me two weeks into COVID. I'm like desperately trying, like Vayner's losing client.

Like, I, that was a very, very treacherous moment. Sure. Vayner was very vulnerable because big clients were scared and they were just firing us. Who wasn't scared? Preemptively. Like, hey, we love you, but we're not paying you. Yeah. Fuck. He called me and said, hey, a lot of people are going to get hurt because of this. People that are very much less fortunate than us. Would you like to help me? I want to do a big charity campaign. But I'm going to need 12 hours a day of yours, of my time. And I'm like, fuck, man, like Ruben was good because like, dot-com businesses were exploding. So for that, it was crushing. Vayner was not good. But I remember just something in me saying, I can do this. I can do both. I can go 24 hours for a couple weeks or a month. And I'll always be happy I did it as a human.

So we created, he created, I kind of co-steered. Alan Tish was there as well. Something called the All-in Challenge. Like you could probably everyone go into all-in challenge.com right now and see it. It we basically him and I, Alan Tish a little bit as well, reached out to every contact we had and we asked the most famous people on earth would they auction off their time? You know, cook with this chef. Shoot shots with this basketball player. You know, be on the set of this, you know, person's movie. And people auctioned it off. And I don't remember, we raised, I think, between 30 and $60 million. In a month for people who had no access to food. Dore and COVID, like really, really like those are the things that no, you know, someone may have known that, but that needs to be. I would argue I'm very, very boisterous about like really wanting everyone to buy V friends. Very proud to be loud about what I sell. I'm incredibly quiet about my personal life.

Am I charitable life? You know, I sit on the board of pencils of promise. I sit on the board of charity water. They give you talk to pencils of promise, during COVID and other times I was instrumental in keeping that, you know, place going, you know, multiple, I mean, I made a $10 million commitment to charity water. They interact with me. I made a $10 million donation over 10 years to charity water to bring clean water to people that don't have access to it. You know, I'm playing it the reverse of everyone. I think a lot of people overthink their content to try to position themselves better than they are. I think I make my content to position myself lesser than I am. I think I'm silly. I think I'm irreverent. I think I show things like garage sales and other things. I don't think people understand the magnitude of businessman I actually am. And I definitely don't think they understand the magnitude of human being that I am. Because I don't use my platform to try to position myself greater than I actually try to

position my content only to be valuable to my audience, not to me. You've said something I was going to read this quote. People are too consumed about their own ego and their content versus the value they provide others. 100%. I think the reason I'm at the top of the game and in that top tier is because I care more about my audience than everyone else. I say that with humility and I say that with confidence. I watch everyone. I struggle to find the individual that is more pocket committed to every single person that comes across a piece of their content getting value out of it, whether it's mentally and getting people stop blaming and start being accountable or whether it's tactically what I said about TikTok live here today. What I said about sub-stack, what I said about Snapchat spotlight, that is better tangible advice to grow your business or personal brand than most of the horseshit that top 10% people are putting out. Yet it was subtle. I said it quickly. Very nonchalantly. You don't have to go really deep into it.

Just go do it. I'm going to leave with it. So you see what I mean? So it's very easy to underestimate what I'm doing. I'm not sitting here with a whiteboard for 15 minutes and people are like something. Which is everyone right now, right? Yeah, and so I'm not doing like S tier A tier. I'm not doing the same stuff. I'm doing the thing, the actual thing. Yeah. And it's very off-speed pitch. Like, again, I'm breaking it down for everyone here. I did it. I did the tangible, like I did the three, I did the thing. I did it. It was simple, but I did it. But most people won't do it. And that's why I get into my content so heavily around in security. Like, you're not going to be able to take the advice of all these experts that you think are giving you detailed advice unless you're in a place of emotional and mental stability. In a place of self-awareness to realize, oh, fuck, I'm not an operator. Hmm. Like, right? Like, and that's okay. I get there, boy. And by the way, I'll say it again, one of the things I'm fighting with.

In fact, I'm going to try to use this moment to push myself further. I need to get out of operating. I've had a great 30-year-run of being COO. For me to accomplish buying the jets, for me to maximize my entrepreneurial legacy, I need to get the fuck out. Hmm. Yeah. The problem is my operating also mixes with my HR. My, when I'm operating, I'm also doing HR work. Yeah. And I said it earlier, family business. Yeah, yeah. And to build my family business dynamics, I need to do my HR. And that's like a thing that I'm going to have to figure out. Because if I go to CEO, to, to mogul, I'm going to be too far from the trenches. And that's where I may lose my culture and HR sub-anteness. And that's a vulnerability that I have to reconcile. You have to figure that out. I go around speaking on stages and part of what my hour-long speeches is talking about people are building businesses the wrong way. And I talk about people who has a 6,000 square foot home.

These people raise their hands. I said that is meaningless. And I talked to them about one thing, I believe. I'll get to my question. People should build a business-based round their happiness. Not based around the thing that the business can afford. Is GaryVee happy? GaryVee's the disproportionate happiest entrepreneur in the game. In a way that, I'm inherently too private personally. And have no interest in exposing my family to the world. But I wish at times I could. Because it would be the cherry on top of explaining to people the truth of how happy I am. But my happiness comes from simplicity. I don't need anything. I definitely don't need a 6,000 square foot home. I don't need to take a private flight. I don't need a million dollar watch. I'm incredibly baffled by the obsession with materialism.

But I understand it clearly. It is grounded in the need about validation. I said I'm a human being. I'm sure there's subconscious subtle elements of my need for that as well. But fucking shit. It is not at the forefront of my mind. It is not how I move. It's not how I think. And my ability to navigate high school peer pressure. And never do things that compromise to who I was. I never made fun of a kid that was lesser than I never drank alcohol or did drugs because I got pressured into it. I always knew who I was at 14, 15, 16, 17. So if I was able to navigate junior high and high school and college peer pressure, well why the fuck would I be playing high school as a grown-up? And that's why I give my mom all the flowers. Because the way I was parented, this is not been a I'm so cool. This is tomorrow Vaynerchuk is so cool because she built me and I am a byproduct of her

and I stand on her shoulders and all of this good stuff in this podcast is because of her. And like cool, I'm very happy about everything we talked about on this podcast about me. But I feel there is no me. I feel I'm the product of her crafting. Gary Vaynerchuk. Great human, great businessman, everyone needs to get to know him by all his books. By everything he's got. You're a great person. I really appreciate you coming. Thank you brother. All right y'all if a couple people need to see this, make sure you share this with at least two of your friends and make sure to give our five star a resume. Five. We gotta go with five. Five. See you guys on the next episode. See you.

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