The Entrepreneur DNA - Being a Great Operator Is My Biggest Vulnerability | Gary Vaynerchuk

Episode Date: September 29, 2026

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. --- 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. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Who does Gary B go to for advice? I had to come to a hard realization in 2024. I mean, financially brutal realization. That I'm not operator. Me being such a great operator is my biggest focus. Gary Vaynerchuk, one of the world's leading marketing experts. Entrepreneur 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 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?

The way I think about business is employees first, customer second, me third. Is Gary V happy? 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. Okay. It was always voyeuristic.

Yeah. Like 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 you know, no more, that's right. No more excuses of like, oh, I missed it.

Gary, you've been doing for this 20 years. I'll never be like you. You sure will. Yeah. Alex Earl was unknown three years ago. Break this a little down for me. This is my own curiosity. Vayner Sports, Vayner Media,

VaynerX, like. VaynerX is a holding company. Where VaynerMedia, so VaynerX is marketing. Got it. Is a marketing production, is a production media, creative, marketing company. Within it is VaynerMedia, the Crown Jewel. Got it.

Two other junior media, 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, Vayner Chuck, Chuck Media, and Tamara group, which is named after my mom. And then gallery, which is a publishing, our Purewow.com, covitor,

and then the speaking bureau, Vayner Speaker. So that's VaynerX. Outside of VaynerX is VaynerSports because my minority investing partner in VaynerX is Stephen Ross, the owner of Dolphins, and he can't own any piece of a sports agency. Got it. By NFL rules.

So AJ and I had to put Vayner Sports outside. side of Vayner X. Then there's Vayner Watt, which is something I've just started talking about, which is a three-year-old TV production company with my partner, Eric Wattenberg. So Vayner Watt. So you'll start watching

Netflix, Hulu, Amazon shows in the next year or two and in the beginning see that logo Vayner Watt, so we'll be spending more time in Hollywood. The restaurant group, the wine store, the alternative sports investment. I was on CNBC last week. My Wiffle

ownership, we just won a World Series. Congratulations, thank you. Pickleball, unrivaled, the three-on-three women's basketball league, the GPL, the sailing league, like we're, me and age you're 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. But 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? 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, Dion Sanders and me. Okay. I just think I'm actually capable of doing more than one thing. Like, 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 Beau and Dion 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 every business I just mentioned every one of them does over eight figures in revenue these are all 10 all of that I mean and we didn't even get into V friends get that do you understand I do I do I do that is wild but I also

don't think it makes me special what I think is 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. Okay.

I think back to your advice. I think if I want one, 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 V-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 Vader-X or 100% of VaynerX or 100% of V-CR group or VaynerWatt 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 and other, you would rather do.

Yeah, I got D's and F's in school because I, from, so let, 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 my, 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 no money. How old are you? Forty-five. Right. Think about 34 years old, 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, $75, $80,000 a year when I was 25, $29.30, I was living a $24,000 a year lifestyle. I had a shitty apartment by the liquor store and did nothing. So when you don't do anything and you don't spend any money, 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, moon shot. 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 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 of heart you have great genetics like I'm gonna be fucking 74 when I inherit this shit so that's why I I had to leave yeah because I wasn't in control vain and I was okay with that because I knew what I was doing from 20 to 30 from 22 to 30 had no problems from 30 to 33 it was starting to build up of like fuck I'm getting fucked here a little bit you did have a little bit that we don't yeah

I don't I don't I've studied you as much as any like yeah 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 with a gas station or a deli knows in immigrant families, not American families. 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 at 30. Okay.

What we fought 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. And 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 dad I was gonna say were you like bro you got to get in here I'm out no I wasn't mad it was like I thought when he was 14 bro get in here we're gonna do this oh okay bro is smarter than me bro at 15 at 15 was

like bro I'm never going to fucking work for dad so I knew in the back of my head for a while I'm like oh shit if I want to be a business with my brother it's gonna be have to be outside of wine 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 S&B. 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, look at Trains' body language. Like I, all the propaganda I put out every day of not listening to anyone, it's real to me. Like, okay, like what?

Like, 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. Yeah. Like my goat, are you kidding me? Like, look, I'm literally even getting goosebumps. You are. 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 learn from whatever to 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 you something nice. Yeah, because for me, nice is I already bought it,

which is optionality. Oh, yeah. I don't want a 13th home. I want what I have, which is I can do whatever fuck I want. How do you do, 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. Hmm.

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? And then I'm in it for like what's in it for someone who buys V-Friends, right? Like I hope I built 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. Like, 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 Rodolitz. David Rodolitz 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 Rodolitz.

Vayner Watt. Eric Wattemberg was 20 years at CIA, 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 Wattenberg. I'm there to like sell a show to be the magic at times to star and shit he's like like if anybody goes on delta right now look up wine game like i'm in that show what did that production he asked me to be in it with carmello and chef andrese why does wine library work because of brandon wernicke brandon warneke's their day to day i'm his thinking partner but he's in the trenches day to day why does fainer sports work because a j's 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. And Vee Friends and Vayner X, I'm the one A. You're the guy. I'm the guy. But Andy Kraniac and John Troutman, my right and left hand and May knew, like there's a lot of people at Vee Friends. And then Vayner X, JT, Kalin, ultimately at the highest level, Mark Yudkin, my general counsel, like my true, like if we were a mafia, my true confidence. You know, like, if I was the boss, like Yudkin's taking that walk in the backyard. saying, are we whacking Johnny?

Or are we not like, he's my guy, right? Like, Anthony Latino, 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, do 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.com. Like whether they start his family, like Marcus Krasastic, who runs international, for Vayner X, who was also Anthony Latino and AJ Vaynerchuk's best friend in first grade and they were three musketeers. Do you know what kind of peace of mind I have

about Singapore? And what I do is I convert people into family, J.T. Kalen, Mark Yudkin, Eric Wattenberg, David Rodolitz, or it starts his family, Brandon Warnockie, 14-year-old best friend, AJ Vaynerchuk, my actual brother, you know, Anthony Latino, Marcus, so to me, the reason I, like, ultimately, I always thought that my autobiography

was going to be called the bridge because I pulled 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? But even like sitting here I'm like huh I wonder if my autobiography should be called family dot business dot

because I think it's family business I'm here to 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 in social media. Yes. What has changed from that book two years ago to today? Everybody, go to Gary VE.com slash attention.

It's a 50-page deck that is to sum up of that book. I'm even saving you 20 bucks of buying the book. Buy the book. Buy the book. Buy the book. the book is still incredibly relevant, thank God. I agree, by the way. 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. 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 no exposure. 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 right this 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 could 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 in a second.

So Justin, hey, what's up, guys? We want to go talk about whatever. Yeah, you're like literally live And the way I would do it just in is 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 his expenses are out of whack or his customer acquisition or Google AdWords is not working anymore

because everyone's going to chat GPT and Claude. 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 can tell by your reaction. I'm excited. You got to look at it.

Are you a writer or no? No. Okay. Funny. English major at UCLA. Interesting. Not a writer. Same.

But I have a team that transcribes my words in podcasts like this until writing. Yeah. So Substack is a massive newsletter platform that's starting to be a newsletter slash Twitter X. Massive. Next. Threads. I don't use it. It's happened.

Cuck and Zucks 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, X considers to grow. Now everyone's so concerned these days with growth, right? Yes. you know what you didn't mention is Instagram. I lean heavy on Instagram and 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 blue, 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 didn't even know Snapchat was the whole thing. I got a shoot like I'm like once DJ Calib left it. 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 look at this person's data on the right. Like there's a lot of people. Wow. Yeah. Like basically Snapchat has its own Instagram. Look at the date on that. Look how much interaction. That's insane.

So literally just posting. And that's nothing. That's not an influencer. That's not Gary V. That was 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. Yeah. 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 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 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 used one of those companies that go. 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 nuanced difference. Of course. But you could 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, fucking get. I'm 50. I'm saying when I make content. Hey, you're 40. You have time. A lot of other content creators like to Rasm. me on that. They're like, I love Gary V, 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. Nobody. 14 active businesses and

work 12 hours a day minimum. Yeah. When I talk about patience or like you're 34, you have time, friends, I'm not saying lay on your couch and jerk off all day. Yeah. 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 day to actually achieve what you're crying about. And 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 my way of saying same thing. That's my point. Yeah. Well said and that's my point. 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 your brain, If you're a 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 same. If you're looking backwards, how the fuck are you gonna, like you're gonna lose, you're gonna run into a fucking wall

and 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. I just believe your life is your 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 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 whenever it was like the 90s had it so good. The 70s had it so good. The 40s had it so good. Friends, do you know how much fucked up shit was going on? 100%. We just 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 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? 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 Vayner Media. For Vayner Media. 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 in 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. NIL. I do B2C clearly. Like everyone, please go to VEEFriends.com and check out my collectible universe. And then I do B2B. Right? If you're a Fortune 500 CMO, 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 you fuck someone's on social. For example, you know this about me because you know me well. I don't put out my personal life at all. I was gonna get there. I, in fact, at all. 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, 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. 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 a brand Gary V before Gary can go launch VaynerMedia the way it's been launched. I think it's and I would argue, I understand why you're saying. Yeah, yeah. And I'm a very bullish. Look what you did with K-Swiss. Brother, I wrote Crush it 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 Zucks. Yeah, but I always, their 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 beat Gary Vee for four years, NIL monetize 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 Gruen's 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. 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. Yeah.

It's good to punch with both. Another book that you may have. Yes, jab, jab, jab. You brought up Stephen Bartlett. I've been podcasting 13 years. He has done something so special. I mean, I 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. This is what he did. This is what Hermosie'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.

This is a game of best. The reason I've done really well is I've been early and good enough, right? Yeah, yeah, yeah. But they should all these people, you know, Logan Paul, Charlie DeMilly, everyone should intoxicate everyone in the audience right now. What is he done? He executed. Yeah. He executed.

I mean, he's just crushing. I watch him and I go, this is brilliant. No, he's very good at what he does. 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, what did Michael Jordan do? He was just maybe the best ever. Yeah. 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 crazy variable. If you are fast in basketball, football, baseball, it's one of the key elements. 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, time. I'm losing the micro all the time. Do you? All the time. Do you ever start a business that just goes, well, that didn't work? I mean, I did a side project slash business called Vayner Toys where I really wanted to garage sale and flea market my whole life. I watched that whole thing. 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 1A and I'm like driving, if I'm, if I'm, if I'm, if I'm, if I'm, if I'm, if I'm, if I'm, If I'm doing, only because I don't do things that are, I don't overextend myself. You know your. 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. in business. And business is easier to pull off than fighting because one shot in fighting and 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 their pusses. Are you an operator? I had to come to a hard realization in 2024. And I mean financially brutal realization

that I'm not the fucking operator. Do you want to know the crazy? easiest thing of all time. Me being such a great operator is my biggest vulnerability. Really? Because you want to get in. I'm too deep. Yeah, yeah.

I'm very C-O-O at Vayner-X. 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 Vayner-X.

Bro, from zero. That's right. Vayner-X is going to do $400 million of revenue from zero. Like, not valuation, not invest. 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 with Ryan Sourhand. He didn't take on any money. He literally said I went and sold. Yeah. I took my money out of my pocket and I said. Yeah. That's what's same.

Same thing. 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. no, no, until... To this day, it's all self- financed. 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 and get his home and all that. And I just took it and invested in startups. So, yeah, this business has come from zero to 400, 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 in profit and putting it back into the business.

Who does Gary V 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, the state, like, do you have all this? Do you go like, oh, this sucks? But I've built something impressive. Yeah. I mean, again, I brought up Mark Yudkin. He's my true confidant, my legal. I've got Anthony Latino as a CFO now. Alan Harker did a great job

almost 10 years before him. You know, Ted Beyer is like a gentleman I used on 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. There you go. You understand?

Yeah, yeah, absolutely. Like, tough to be, like, I'm not on defense, bro. Yeah, you just keep going. Like, I'm just creating well. I'm creating things. I'm building things. I'm not protecting a lucky moment in my career. How from the outside perspective, my interest in sports cards has increased since COVID.

You and Michael Rubin, where did that friendship start? We met, you know, we were coming up the game in different. I feel like you guys, because I don't know him at all. I feel like you're the same. We have a lot. Oh, yeah. There's a lot of. Pretty close friendship there.

There's a very close friendship there. I mean, I've spoken to him four times in the last week. Yeah. They were very close. We met in, you know, I remember once 15 years ago, maybe more at a Dr. Oz party up in Bergen County, New Jersey. We had a nice little yap. 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. first time I told him he should buy tops. Hmm. Look where he's at. And so, and then, and then we really got close during COVID. Okay. He called me, we had kind of started hanging out every six months, maybe in 15, 16, 17, 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 is losing, like, I, that was, I was, I was, a very, very treacherous moment. Vayner was very vulnerable because big clients were scared and they were just firing us.

Who wasn't scared? Preemptively. They're like, hey, we love you, but we're not paying you. Yeah, 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?

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 Fanatics 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. Okay. Like you could probably everyone go into All Inchallenge.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. Yeah. And people auctioned it off. And I don't remember, we raised, I think, between $30 and $60 million.

Okay. In a month for people who had no access to food during COVID. Like really, really like. Those are the things that know, you know, someone may have known that, but that needs to be talked about. 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. Yeah. I'm incredibly quiet about my personal life

and my charitable life. You know, I sit on the board of Pencils of Promise. I sit on the board of Charity Water. I think if 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 interacts in me. I have 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. Yeah. 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 pot 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 to stop blaming and start being accountable,

or whether it's tactically, what I said about TikTok live here today, what I said about Substack, what I said about Snapchat Spotlight, that is better tantaliener, manageable 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 gonna 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 like people like sometimes. Which is everyone right now, right?

Yeah. And so like I'm not doing like S tier A tier. Like 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, oh, 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 insecurity. Like, you're not gonna be able to take the advice of all these experts that you think

are giving you detailed, 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. Like, right? Like, and that's okay. And by the way, I'll say it again, one of the things I'm fighting with,

in fact, I'm gonna 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 like maximize my entrepreneurial legacy, I need to get the first, fuck out.

Yeah. The problem is my operating also mixes with my HR. 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. Yeah.

And that's like a thing that I'm going to have to figure out. Because if I go to CEO, too, too mogul, I'm going to be too far from the trenches. and that's where I may lose my culture and HR savantness, 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 speech 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. And I'll get to my question. People should build a business based around their happiness, not based around the thing that the business can afford. Is Gary Vee happy? Gary Vee'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 of outside 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 compromised 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. I was at 14, 15, 16, 17. So if I was able to navigate junior high and high school and college, you know, peer pressure, well, why the fuck would I be playing high school as a grown-up? Yeah.

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 Tamara 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 and 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 known 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 a five star resume five. We got to go with five. See you guys on the next episode.