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This is the GaryVee audio experience.
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When I'm out, whether it's on a lecture circuit or anyplace else, I got this famous saying, I'm brilliant because I know I'm not. I simply learn from those who are, and I take notes and I do it from there. And that's a perfect segue into talking to my next guest, because this is a man described as one of the most forward thinkers in the world of business. He's a serial entrepreneur, but strategist and is considered one of the leading global minds on what's next in culture, relevance, and, dare I say, even the Internet. The one and only Gary V. As in Gary Vaynerchuk.
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My man.
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What's up, my man? It's good to see you.
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It's such a pleasure.
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How you doing?
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Too good.
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When you hear yourself described in that fashion, tell me what comes across your.
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Mind similar to your opening line. Deep humility. I'm detached from it a little bit. I'm detached a little bit from it. I get that. I've worked really hard and I've earned, and I gotten to a place where I can get some roses and some flowers because I've put some points on the board. But, you know, I think a lot about, like, serendipity. Why was I born with intuition that led to me being right about a lot of things? You know, why was I fortunate to be born in the Soviet Union, come to Queens, New York, with nothing, and have a. Have the foundation of adversity? Adversity leads to success. That was. I would. I didn't pick when I was born. So there's a lot of serendipity that went into it. A lot of hard work.
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Okay.
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I'm not, you know, I don't think you just get there on vision boards. You got to do it.
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When you say points on the board.
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Yeah.
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Highlight and illuminate for folks what that means to you. What do you qualify or quantify as points on the board in your mind?
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Well, in my mind, points on the board is like what people talk about me behind my back that actually know me. That's the actual answer in the way that I used it there. Why do people look at me in a business world? I did invest in Facebook before people knew. I did invest in Uber before people knew. My brother took the first Uber in New York. I was early in this game. I did build my dad's local liquor store to an Internet company in 1997, when people weren't even thinking that way.
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Grew from 3 million a year to 60 million a year in four years. Is that accurate?
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In seven.
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In seven.
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I did start VaynerMedia in an office of another company because I had so little money. And the last 14 years it is a 3,350 million dollars a year business, you know, so I've, I've amassed my following. I've done work. I am a five time New York Times selling best author. I am a very prolific public speaker that gets comped properly. So I put in the work. But when I hear that, you know, it's, it's nice. But I always want to not get high on my own supply. I'm still in the game. I'm trying to buy the New York jets.
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Okay.
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I'm far away from that.
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Right.
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So what I'm really doing when I hear that is nice. Thank you. Grateful to my mom and dad, really. God, all that stuff. But still in pocket, still focused, putting nice wins on the board for my own self like this, you know, I'm honored to be on this show.
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I appreciate it.
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I'm a fan.
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Thank you so much.
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But then, you know, knowing that I want so much more so and being grateful if the God of life dropped down now and was like, this is it, you capping here going to flatten out, actually decline. I'm like, okay, like that's disappointing, right? But I'm grateful for what I have, but I'm hungry for more.
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You've already made me a bigger, even bigger fan of yours than I already was because you talked about never getting high on your own supply. So you love Biggie. I appreciate that. You, you Love the Notorious B.I.G. way to go with that. Way to go with that.
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Just asked me what my, literally an interview I just did, they're like, what would you be your ideal halftime show? I said bone Thugs in harmony and a hologram of Biggie. That's the halftime show I want loan and Biggie is forever.
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I see you. When people talk about the inordinate number of followers, I think it's like 45 million followers at the very least on social media. Why do you believe people follow Gary Vee? What are they looking for from you at this particular juncture in your life in terms of your interpretation?
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I think it's been ebb and flow. You know, my early beast was because I was talking about wine and a lot of people were interested in it and I wasn't talking snooty about it. So that was my early base. When I really popped off in 2006, 7, 8, 9, the economy was bad. And I was talking like, yo, you can make money on YouTube and Twitter. And people were confused by that. And so early on, it was for someone that was showing the way. I think now it runs a lot of gamut. I have a lot of people that follow me because I talk about modern parenting. I think parenting is in a weird place in the world.
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Yes, it is.
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You know, I think a lot of people follow me for what's next. Cause I've got that track record. You know, it's funny. I think as a public figure, I'm very good at finding purple. I like that you wear purple a lot, by the way. I like purple. I think America's gotten too red and too blue.
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I agree with that.
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And I think purple is the magic. And so I think today, if I analyze why there's traction, I'm in love with purple. And I think people appreciate that because I think we're a little tired of.
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The extremes I'm looking at right now. Just looking at some of your current companies. VaynerMedia.
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Yes.
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CEO, Global Advertising Agency that creates a lot of content for tweets, Facebook post pin interest, Instagram and others. Rare. Next. You're the chairman. Combination of several media companies, of course. Bana Sports. All right. Full service talent representation and brand consulting. We might need to talk. I need to talk. Okay. Empathy Wines, of course. Direct to consumer Winery. And that caught my eye because of the world that we're living in, moving from linear to digital in television. In my world, which obviously everything is your world with what you're connected to right now. So as we sit here today and you're a visionary, how are you feeling about where we are as a nation, as a world, from an advertising perspective, from a global reach perspective, in terms of being an influencer, how are you feeling about this right now?
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Very happy. Why? Because I'm going to be historically correct.
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Okay, but what if you're historically correct about something very, very bad that you predicted? What about that?
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Well, I'm not predicting anything bad. Okay. In the context you asked the question. I'm the person in advertising right now that's saying 90% of the money that big brands are spending is going in the garbage.
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Okay.
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I'm the one that's saying a $7 million Super bowl ad is a bargain because 165 million people will actually watch your commercial. But during even the biggest sport, the AFC and NFC championship game, nobody was sitting around excited to watch the commercials in between the game. I'm the one that's saying TikTok this or streaming that. So what I'm trying to do is day trade attention. That's what I do for a living. And by the way, it's why I've watched your career for so long. I mean, we're going way back. I'm like, oh, this kid's got something, you know, oh, this influencer. There's a reason Logan Paul or Charlie d' Amelio or all these things that happen in my career. I'm watching underpriced culture, underpriced distribution, underpriced executors. And so in the way that you asked in the media landscape, I'm excited. Cause things are about to change. Heavy.
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Okay. I was getting ready to ask you about that because I'm thinking about the merger that espn, Fox, the joint venture, I should say, not a merger that ESPN Fox along with, you know, Discovery, you know, Warner Brothers Discovery got into. I'm looking at stuff like that. I'm looking at what their collective worth is compared to Amazon, which is in the trillions. Apple, which is in the trillions. The rest of those folks are in the billions. I'm wondering how you're feeling about stuff like that. When you see it as a visionary.
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What's very clear is, and this is something I've been talking about for about seven or eight years, Apple and Amazon were not coming to fool around these traditional media companies, including my favorites, espn, all that. You know, there's always a bigger fish. And the reality is the Internet is the big dog. And so what happened was there was all these people that held onto the radio. When we finally had television in the 50s and 60s, I was a really poor student. Stephen A. But the one class I was good at was history. And I never understood until I got to my mid-30s. I'm like, Damn. That's because I believe in pattern recognition and history repeating itself. And so what's happening is. What do I think? I think the world's gonna change quite a bit. Apple has the mls, Amazon's going to own this football thing. It's going to play out and the NBA. And you know this because you're very close to it. They're not fooling around with this next deal. And there's a lot going on and Ryan Smith with the Utah Jazz is doing different stuff and Matt Ishby is with the Suns. It's like things are changing and the way people are going to consume content and how they consume and where, you know, this a kid that's got talent. 15 year old, you 19 year old you, 23 year old you. He now has TikTok and YouTube. He can build his audience. He didn't need people to put him on right. People had to pick you along the way. People had to subjectively say you're a talent and a lot. You know this. You came up with a lot of guys and gals. Some of them just didn't have the political luck of the draw. They didn't get picked. But there is no pickers anymore. Everyone goes direct to consumer. Now social media is not a ha ha ha joke. It is the foundation of everything.
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But is it just about numbers or it is about substance. I'm talking to Gary Vee and every word, every syllable that comes out of your mouth is about substance.
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And then I. And then I earn numbers.
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All right, and then you earn numbers. Now numbers are important. Numbers are matter. I pay attention to them every day. Make numbers everybody. But I also see people that are getting an exorbitant amount of numbers and they're getting it in a fashion, distributing and disseminating content that I might not necessarily vibe with. Do I go for the numbers and throw that aside and throw everything else aside because I want those numbers or do I attach myself the substance thinking that that's the long game that ultimately reap the fruits of my labor? What's the mentality that somebody with that dilemma, what's the mentality they should grab?
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I believe especially watching you from afar. It's an easy question. I understand even why you're asking me this question. It just depends on how you read the tortoise versus the hare. You know, to your point, I tell people all the time you need to be out there but if you're saying things you don't believe, that's right. It's not going to play out. Never the end. It's a very simple game. The it all so in my content. One of the things that annoys all these kids that gave me daps on the way to walk in here, the one thing they'll tell you if you really talk to them, the thing that annoys them is that I push patience so heavy and they hate it.
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You know this, the kids, they want everything now.
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When we grew up, we were like maybe at 40 some things would click in.
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They want everything now.
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And I don't blame world's fast. I get it but you can't do five pushups and look like a G. You got to put in the work. And so, you know, from my standpoint, what would I say if you want a Couple of years of enjoyment and some fake fame and accolades, then attach yourself to anything and not be about real life. If you want legendary status, if you want it forever, and most of all, if you want to be able to put your head on your pillow at night, you better spit things you actually believe. Listen, in your business, I see these people all the time, come and go and you know they're in trouble because you know they don't believe what they're saying. You know it.
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Yeah, I can't, I have no patience with phoniness.
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And so for me too, like I can't do you know in advertising how disliked I am. I'm sitting there and poking sacred cows. I'm saying every television commercial is a waste of money. Besides Super Bowl. I'm sure you can imagine that a lot of people in that $80 billion industry per year in America, it kind.
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Of hurts our feelings.
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They have feelings about it.
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Hurt their feelings. That's right, absolutely.
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And so. But I'm too scared to be wrong, right? How can you say things you don't believe?
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But if 80 billion, let's just say for example, 80, 90% of it is wasted time, wasted advertising, right? And we all understand that these are the kind of things that fuel the system. I mean you could look at the criminal justice system, you don't even get me started with that. You know, you know police officers, the lawyers, the judges, the, the prison system. Except the system itself, we know all of this. So anywhere you look, anywhere you go, there's always something systemic that has some level of influence, right? So when you say what you say, do you ever find yourself looking at society and saying to yourself, you, there's an abundance of people out there that are not equipped to handle the change that ultimately has come forward and how.
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As a society going to adjust to that, especially when in this scenario it's predicated on their own greed. Big companies go out of business because they care about the short term. Founders tend not to go out of business. Mr. Old School Toyota isn't going to be the reason Toyota failed. It's some executive that got paid and just wants to make their money on the stock price and so they'll milk it because they know they're retiring next year. Whoever gets left with the bag. That's right. So in this scenario, the reason people keep spending money on television commercials is cuz the four media companies that buy those commercials are publicly traded and they make money on buying TV upfronts and they don't care. So I get that. But the Reality is it doesn't mean that these consumers are acting that way. And that's why there's always opportunities for kids and people on the come up. Because big companies play short. Humans, the right ones play long.
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As we sit here right now, so many people in the business has looked at the transition from linear to digital.
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Yes.
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Not just in television, but in anything, everything. And their mentality is. Is that most people haven't learned how to monetize.
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Yes.
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Digital. Do you agree that that has been the case?
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No. I think big companies don't want to give up the big bags that they've figured. Traditional.
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Right.
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There's plenty of people that have monetized digital. As a matter of fact, there's way more humans that have figured out monetizing digital.
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But I'm saying those big companies that were making money in traditional, you can make money in digital. Why aren't you prioritizing, really, mastering how to make money in digital the way you did in traditional?
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Because at that level, those are nickels and pennies and dimes to the dollars they made in these big upfront monster deals. And so they're secondary. Plus, you know this because you pay attention. The big dogs in these companies, they're not about that life. And so they make decisions based on themselves.
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Right.
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It's the naivete of the game. They just don't see it.
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So your brilliance is obvious and it's well recorded and well documented. Riddle me this. Why the hell do you want to own the New York Jets? What is that about? Why does. Why would a winner such as yourself associate yourself. You're going to love your fandom, your love, your emotions, and everything else in between with the New York jets, who, by the way, haven't won a Super bowl since 1969.
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January 12, 1968. 68 season. January 12, 1969. Best day ever. I was negative six.
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That's right, negative six. Go ahead.
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Because I want to be driving the car. The most guaranteed way that I know I'm gonna get a Super bowl is for me to do it.
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Okay. And they say that you say you're not worth enough.
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I'm not.
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To purchase the New York Jets? Yes. May I ask how much you're worth, sir?
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I mean, if I liquidated everything and somebody thought that I would stay with the companies that I sold it to, I could get into some real numbers. Hundreds of millions.
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Okay. I mean, hundreds of millions is very vague, sir. I like specifics. I mean, can I get, like. I'm trying to be a little bit.
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More Practice with my life these days.
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Okay, no problem. Problem. But at least I asked.
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Look, the jets are growing. I'm. I'm building too. The problem is that these NFL teams are building fast, too. So, look, I think I need a good 10, 15 years of real execution to put me in pocket to make a play. But here's the thing. And. And again, looking from afar. We don't know each other like that yet, but hope we do over the next decades.
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Absolutely.
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When you're ambitious, you're kind of just, you know, this is probably. This is probably why you associate with athletes, too. This is my assumption from afar. You know, when you're in your zone. Yeah, I'm in my zone.
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Yeah.
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Like, I know. I'm trying to get there. I also know there's a lot of serendipity that goes into it. I'm not in full control. The Johnsons may want to sell next year and it's over. I would have never thought if, let's say my goal was to buy the Mavericks.
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Okay.
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I would have been cooling because I'm like, Mark's young Cuban's. Not selling this for another two decades. I'm good. Boom. It transacts. So I need a lot of things that I don't control to happen to go my way. I'm just focused on building an empire to give me a shot.
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Sports, yes, that's the Jets. But in your line of work, sports and culture are equally important. It matters to you. That's your future audience, that's what you're doing or whatever. How do you think they intertwine in this day and age? How comfortable are you with it?
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Oh, I think sports is one of the four to five pillars of popular culture, like sports and music. Fashion and food have had a good decade or two.
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Fashion, food, sports, music, and what else? You know, five. One of the five pillars.
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I got one. I got one that's really emerging. It's not there yet. Okay, I'm going to make a prediction because I want to look at this in 15 years and be like, okay, something crazy is going on with collecting, and I grew up with it. Sports cards, all that. But then all of a sudden, man, if I knew all those sneakers were going to be worth this kind of money when I was coming up. And then contemporary art and just as. Even if you look at the Taylor Swift effect on the super bowl, here's a fun fact that a lot of people aren't paying attention to that. I am. I'm watching little girls post Travis Kelsey, rookie cards on TikTok.
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Yes.
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So collecting is starting. And I think in 20 years, when you go out to dinner, you'll just ask everybody the same way. What are you listening to? Oh, that new Kendrick Lamar. What do you are. Oh, Rashid Johnson. When you're talking like collecting, I think people are just going to talk. They're collecting something.
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Got it. Two more questions before I let you get on out of here. Which clients of yours are running ads this year at the Super Bowl?
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We've got one. Starry.
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Okay.
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And we're really excited about it. It's proper. It's a good one.
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Best super bowl commercial you've seen in the last five years.
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Let me give you my favorite one of all time. And then last five years, favorite one's very personal. Cindy Crawford, Diet Pepsi in her Daisy Dukes. That was the day that I went from being a boy to a man. So that will always be number one for me. I was like, what are these feelings? I was like watching football, Redskins, Broncos, just chilling. Being a boy, I was like, why am I feeling different things? So that was a quintessential moment of my coming of age. Last five years, you know, coinbase two or three years ago, did that bouncing QR code.
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Okay.
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I think super bowl isn't selling enough or being transactional. They want to put celebrities in. They want to make us laugh. If I keep telling my clients and I and they're still not there yet, but I think in super bowl spots, you should be getting people to download your app. You should be getting them to buy stuff. I still think this is Super Bowl 58, right?
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That's right.
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Yeah. If I'm a company that sells $150 item, a sneaker, a technology piece. I'm saying my super bowl commercial is like for the rest of this game, until the game ends, triple zero on the scoreboard. This $150 item is $58. I don't think we're collecting first party data. If you're paying seven mil and then you got to make something for some money, get that data. Because first party data, that's the game. Got you back to direct to consumer. I know we're wrapping up. When you. You are fully direct to consumer because you will be. Because it's an inevitable chess game, something like that, you're going to want that first party data. It's Nice to have 10 million followers on Instagram. It's a lot better if you had 10 million phone numbers and emails.
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I'm with you. Last question. Real quick. I need a 1 minute answer on this.
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Gotcha.
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You leave here today because this will not be the last time you and I talk here. We promise you that. What message do you want my viewers and listeners to get from this conversation that we just sparked with one another.
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As we look forward in life? You find what you're looking for. If you want negativity, you can find negativity on the news and social media all day. But let me throw you the curveball. Curtis Martin, my guy, perfect guy to walk by. Perfect guy to walk by. But if you are looking for positivity, it's all out there. And so your viewers and I know your audience. Cause I'm part of it and I watch how we all chop up of the things you say and things you get into. You need to start looking for positivity because you actually can. There's systematic things that are broken. Maybe your mom or dad. It was this. There was adversity everywhere. But you are actually capable in this Internet world to do things. You just have to choose to.
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That gives, you know what? That gives us all hope for the future. Because if people choose to be positive, then the world will be a better place and we'll all be in a better position. That's basically what you're saying.
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And I'll really go one last notch because I know we're out. When you were met with positivity, you do not have to act that way in return. And I'm not even saying Michelle Obama, go higher. I'm saying feel bad for people that come with heat. Yeah. For somebody walk around and spend their time to tell you you suck.
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Yeah.
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Do you know, suck of a life that is.
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Yeah, that.
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So be happy you're not the one doing it. My man.
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One and only Gary Vee, right here with Stephen A. Right here on the Stephen A. Smith show. Over the digital airways of YouTube lessons, pearls dropped on everybody. This will not be the last time I have a conversation with this man on this show, I can promise you that. Because I love to entertain, but I also love to educate. And I just received an education. I really appreciate it. For Gary Vee, this is Stephen A. Signing off. Until next time, everybody, peace and love.
The GaryVee Audio Experience | September 7, 2025
In this dynamic conversation, Gary Vaynerchuk (GaryVee) joins famed sports commentator Stephen A. Smith for a candid discussion about the roots of success, the evolution of business and media in an increasingly digital world, and the role of culture and adversity in shaping individuals and industries. Together, they explore personal values, the value of patience over hype, the future of advertising, and the intersection of sports, business, and popular culture.
On Substance:
“If you’re saying things you don’t believe, that’s right. It’s not going to play out. Never the end. It’s a very simple game.” (09:51) – GaryVee
On Legacy and Ambition:
“When you’re ambitious… When you’re in your zone. Yeah, I’m in my zone. Like, I know. I’m trying to get there. I also know there’s a lot of serendipity that goes into it. I’m not in full control.” (16:05) – GaryVee
On Positivity:
“You need to start looking for positivity because you actually can. There’s systematic things that are broken. Maybe your mom or dad… adversity everywhere. But you are actually capable in this Internet world to do things. You just have to choose to.” (19:57) – GaryVee
On Haters:
“When you are met with positivity, you do not have to act that way in return. … Feel bad for people that come with heat. For somebody walk around… to tell you you suck. Do you know suck of a life that is. So be happy you’re not the one doing it.” (20:44) – GaryVee
Super Bowl Nostalgia:
“Cindy Crawford, Diet Pepsi… That was the day that I went from being a boy to a man.” (18:02) – GaryVee
GaryVee urges listeners to cultivate positivity, authenticity, and patience in an era defined by rapid change and limitless opportunity. He explains that, despite systemic barriers and cultural adversity, individuals still have unprecedented agency in the digital age. Ultimately, legacy is built on a combination of self-belief, resilience, and a long-term approach, not fleeting trends or shortcuts.
This richly engaging episode brims with actionable wisdom, humor, and hope—perfect for anyone seeking to navigate the changing tides of business, culture, or life itself.