Today's guest needs no introduction, but I'm going to give him one anyway, because his story is just that good. Gary Vanachuk, entrepreneur, investor, producer, host, best selling author, and one of the most electrifying voices in business today, is joining us. From building Wine Library into a powerhouse, to leading Vaynerrex Veno Media, be Friends, Veno Sports, Venusree and shaping the future of marketing and so much more. Gary has redefined what it means to stay ahead of the game.
His insights on brand culture and the power of attention are legendary, and his energy absolutely unstoppable. So get ready for an unfiltered, no bullshited conversation about his personal story, the future of business, content, social, and what it really takes to win in today's world. Gary, Welcome to the show. I'm honored to have you with us.
That was very nice. Thank you for having me. I'm glad to be here. Let's do that.
Yes, awesome, great. So I always started with a couple of more personal questions, so I would love to ask you. You are as I said, you know, a high energy entrepreneur, marketing guru, futurists. However, we call you and you let us know maybe in a minute, but that barely scratches the surface of so many talents. With all the projects and companies you've already launched, what's one idea or one passion you haven't had time to pursue yet but would
love to bring to life sooner rather than later. Is there anything that's a great question to start this up?
And it's really tough one because really, v friends, was that I knew my whole life that I either want to buy or start an intellectual property. You know, I'm forty nine years old. I grew up in the eighties. It was everything Star Wars, you know et you know, Transformers, Gi Joe and I have three and a half, your younger sister I was very close to. So it was Cabbage Patch Kids and my little Pony and Strawberry Shortcake, and you know, it was just back to the future.
There was so much good going on in the eighties of intellectual property being created. So I would say that one always loomed I got to it. I would say, the last thing I really want to get to for sure is I do get excited about the concept of doing private equity to buy iconic nostalgic brands and refurbish them with contemporary marketing. And that's why I started Vainermedia in a lot of ways. So that's still looming for me.
And then I want to have an era where I go to a cave and not shave for a year and just have people find me and ask me questions, like a Yoda like character. So I definitely want to scratch that in my career, like a sabbatical where I just give back on a one to one level in an unscalpable fashion. Obviously I just used a silly kind of example, but something like that is something else I want to do professionally, and there's probably some other things for sure.
Awesome, Awesome, I mean what an ants as the first for the crush questions? And obviously you know, if we weren't possible long enough, you know, we won't become iconic enough for you maybe to step into our business as well, maybe in fifty years or something like this. All right, good to know it, was there ever a moment in your childhood, you know, in your early days that perfectly
foreshadowt the entrepreneur you would become. Was there a moment where you where you learn about this and you knew what to do in your life.
The first part, for sure. I actually ironically just brought it up earlier today. I am fascinated to this day of how interesting my Lemonade Stan career was. You know, having a lemonade Stan is such a tail tale kind of indication to entrepreneurship, especially in the eighties and nineties. Ye, but when I did my lemonade Stan, I you love
this Christian. I spent more time making signs and figuring out what tree and what poll to put it on, and so the even at my early stage, it was clear that I was going to be a marketer, because I think I put more time into marketing my lemonade stand than definitely making the lemonade. I think I should have done a better job making it a little more delicious.
There's too much sugar in there, So that's that I think. Yeah, very early on the first time I did a baseball card show, selling my own baseball cards in a mall in New Jersey, I knew that I would never not be a businessman, you know. So somewhere around five, six, seven, eight, nine, ten, eleven, twelve, those formative childhood years when it would snow and we would have a day off from school. Most of the
kids went and made snowmen and had snowball fights. And I did a lot of that too, but I would say at least thirty to fifty percent of the snow days, I would go into my parents' garage, grab a shovel, and go ring doorbells and work hard for five bucks. And so my childhood is an incredibly clear preview to who I became. And I think one of the reasons business works for me is I do it for the game, not for the money that comes along with the game.
And I see a lot of people who do that, and I think they're happier, less anxious, not always more financially successful. I see a lot of people who just do it for the money make more money than people that do it for the love of the game, but all of them are less happy, more anxious, and I'm very grateful.
I agree completely with you that you know, having just one motivation doesn't matter what it is, you know will limit you in your success and your business success, whether it's just going for money or or just having fun. I think it has to be a kind of combination of a lot of things. However, we come back to this in a second. Okay, So one thing I would love to hear from you is, you know, if you had to choose, what would you say is your most
defining character trait? Is it a perseverance, is it creativity, is it integrity? Or is it something completely different?
Self awareness?
Self awareness?
Yeah, if you ask me to answer you on that, I think being competitive is very up there. Yeah, being tenacious is very up there. I think optimistic is huge for me. And I know people are confused by this, but I think being kind has been extraordinarily important to my success. As you know, because we run in the same industry. There may be some people that don't like me, but nobody who actually knows me doesn't think that I'm
not a nice guy. And I'm proud of that, and that's an indication of being well parented and a strength of kindness. But all of those things are secondary. I think self awareness, which I think leads to the combination of confidence and humility. Yeah, you know, I just know who I am, and I know what I'm good at, and I know what I'm not good at, and the things that I'm not good at, I don't think I stink that doesn't lead to insecurity. That just leads to reality.
Everybody has strengths and weaknesses. I feel like I'm also empathetically self aware, meaning when I was when I was a bad student, I understand I was coming into business world. I knew that people thought I was dumb and not good because in the eighties and nineties, where you went to college was the indication of your worth. And I wasn't upset that people thought I wasn't going to be good.
I understood them. Today, when I walk into a room in our industry and I can see someone's like not jiving, I'm empathetic. I'm like, oh, that must be a competitor who doesn't know me or took something I said out of context. So I think self awareness has been the one.
Which is a huge achievement. I think if you know who you are, I think that's a big advantage how to act and that people can really rely on you whatever personality you are. I think that's a huge achievement. I think obviously you've met and you've mentored so many people, young people, senior leaders across the industries. Who's the one person who has truly surprised you with their journey, and
why is there one who stands out of this? Maybe you had a complete different expectation, you know, meeting this person.
Well, i'll give you an interest one. I'll go with age a Bayer truck. I'll go with my brother in this one, all right. My brother grew up very similar to me. We're eleven years apart. We grew up differently because we were in different economic situations in our childhood. But he's incredibly capable. He has a lot of strengths that are stronger than mine. He's wildly competitive. He's extremely ambitious.
You know, you said you are. I don't know if he's more ambitious, but you know where I'm about to go with this story is interesting, you said, who surprised you? Aj has Crohn's disease, and early in his career at Vayner he had a pretty bad spell and had to have a decent chunk of his small intestine taken out and it completely changed the course of his life. My brother is way more rounded than I anticipated. I saw him as, you know, a little bit more like me.
And because he is a lot like me, right, and I'm saying this as a positive, I'm really proud of him as a father of three young little ones, as a human who has found lots of time for his passion and golf in his tempered ambitions of professional achievement. I think he's incredibly well rounded and incredibly comfortable in his skin, and also has a brother that went on to be really like me, you know, and just the way he cheers for me and doesn't see it as
a negative, and the way he preshoots me. I'm just grateful, as you could probably tell by my tone. But if I'm truly going with surprise because I had so many expectations because I just watched him and enjoyed him, and you know, when he was thirteen, he would like out negotiate me for business deals we did together, like you know, because he was tough. He was like, no, we got to be fifty fifty. I'm like, I'm put up all the money and doing all the work. You're just shipping
out the packages for eBay. He's like, well, they wouldn't ship without me. I'm like, that's true. I'm business building, that's business. So like you know, I just he would be the one that most surprised me. Yeah, I'll give you another one, you know. I would tell you. The one that least surprised me was Mark Zuckerberg.
All right, why is that?
When I met him very early on. Yeah, I know this is probably podcasts. I don't know if this is visual, but you're looking at Facebook stock here. I bought Facebook very early on off with Mark's parents. I met him very early on, right, and he was the only person I'd ever met up into that point where there was no doubt in my mind after my first dinner that he was going to build one of the biggest companies in the world. All right, you know that would be like that's an it Like it was funny when you
asked the question. Like the things that ran through my mind, that one stands out because, like I truly thought he was going to build one of the five or ten biggest companies in the world, which is a ludicrous thing to think after one dinner at like, you know, and the company was big ish, but like not to I
knew it. I knew it because he knew consumer, which I look for, right, And then there's a there's a lot of you know, the other thing that I'm thinking about that could have happened if I go a different route. I've made a lot of investments in guys and gals that I knew could either build something big or it was gonna fail horribly, and normally it fails horribly. I've changed my investment thesis, like this is you know, it's funny by the way I think I represented this for
a lot of people. There's a lot of people that come up to me through the years that say, man, you know, it's just where they are with me at this point. They're like, man, I got to give you some respect or flowers. They're like, the first time you came across my path, I'm like, this fucking guy's a piece of shit. Like he's not gonna he's not gonna last. This is a fly by night and I and I
understand why. I think when you're very big personality, when you're you're high energy, when there's a lot going on. But because I knew I had it, I invested in a lot of kids that had what I had. The problem is, ninety percent of the time does end up being what you think it is, which is all hot air. And so it's been it's been an interesting journey of expectations versus surprising outcomes. But aj because it's a respectful surprise. I'm so happy for the balance he has for himself.
And it's a great story you can share with our listeners because you know, it's obviously somebody you're very close to all your life, and you you work with him, you spend a lot of time with him, So which is great. You have said person who surprised you most, as you said, you know, still in your life, and you know, being being a core part of your life,
which is which is amazing, Which is amazing. I just think about, you know, going back to your to your Mark Zuckerberg example, because obviously you invested in so many companies. You've mentioned Facebook, but you invested into Twitter early days, coin Base, Slack, Liquid Death, Uber, and and so on. Was it just because you knew this person? You know?
What was this? I can break them all down for you. Facebook and Twitter and Tumblr were the first three companies I invested in. It was a It was a moment of brilliance being in the right place at the right time, and I probably will I'm not sure if I'll ever be able to replicate it. I was so uncomfortably right that social media was gonna win, and I did such a good job vetting the entrepreneurs. Back then, I didn't think I was an investor. That's a lesson. I want
to really make everyone listen carefully. When I didn't think I was an investor, I invested best. Okay, all I did in two thousand and six and seven when I invested in those companies was I had a little bit of savings after working for twelve years for my father. I didn't make a lot of money those years, but luckily I lived so humbly that I had a little
bit of savings and I spent it all. All the savings that I amassed in my life, I invested not equally, seventy percent of Facebook, twenty percent to Twitter, and ten percent to Tumblr, and they all returned staggering. If I had money back then, I'd probably be running the jets for the last ten years. It would have been open. The multiples were tens of thousands of X, like crazy numbers. But I didn't put enough capital to like completely go
to stratosphere. But I'm not complaining Comma. So those my friend Christian was I was. I knew social was going to happen, and I met everybody, and I just thought those three and the one for me at Twitter wasn't Jack Dorsey was actually Avan Williams. Okay, he was the founder that I most was like, that's the guy, and he was the guy at the time more than Jack. Actually were equal to Jack, but Evan was a little more front facing. That was that Liquid Death. Mike worked
at vayne or Media. The day before he started at Liquid Death sent me an email and I wanted to support him because I liked the narrative of me supporting my employees on their own entrepreneurial venture. And I liked him and thought he was creative. But I would be lying out of my ass if I could have comprehended the level of business that he's been able to build. And I'm so happy for him. Slack's a wild story.
Stuart Butterfield, the founder of Slack, was the founder. The co founder of Slack, was the co founder of Flicker. Flicker was one of the most important websites in Web two point zero and in a lot of ways was a precursor to Instagram. Right, it was a photo app, but it was desktop, not mobile, wasn't out yet. It sold to Yahoo for like forty to sixty million dollars which was an enormous number at the time, and I read a lot about Stuart and I when I went to California on a trip, I went out of my
way to like find him, meet him. I met him. We hit it off. We didn't we hit it off in the moment for an hour, for thirty minutes, that was really it. We would talk on Twitter a little bit, an email here. But then when Slack pivoted from I don't know if people know this Slack was a game. No, I didn't.
I didn't know that.
Do you know that.
Slack was a product that was built for a remote workforce building a desktop game. They built it for them sells to talk to each other, and that became the actual company what if?
Sorry?
Yeah, they ate their like it was crazy. Their own feature internally became the app. It's I love when sawdust becomes the actual thing you sell. It's an amazing story. So I got in early there because of that. Uber's a wild story. I mean, Uber's my biggest miss. I didn't invest any Angel round. Travis was my closest friend in that era of social investing. We were investing together a lot, and I said no twice because I just bought an apartment in Manhattan, and I was very, very
e liquid. Yeah, And I love that I lost out on hundreds of millions of dollars by saying no twice because it reaffirms my biggest thesis, which is scared money doesn't make money. And it was one of the few times I was on defense in my entire life, and it was one of my biggest financial misses. It's my biggest financial miss.
Have you ever missed one opportunity completely where you missed to invest any single dollar in where you say, oh shit, you know this is something I should do.
The biggest misses in my career Uber I invested later. I still did very well, but it could have been I mean I literally could have made three four hundred million dollars on fifty thousand dollars investment. AIRBMB emailed me. It was Joe, one of the co founders. His email was Joe at air Ben and Breakfast. I don't know if people know this Airbnb the B ANDB stands for
Ben and Breakfast. Airbnb emailed me. I never saw the email, so I love that I have the email, but I don't regret it because I don't take that loss personally because it's not really lost. I didn't see it. Pinterest was introduced to me before Ben even went to California when it was being done in Pennsylvania. Also, I didn't have the meeting. I later invested fairly early on again kind of a half win half loss. Yeah, what is the biggest company that I passed on where I was like, no,
this doesn't have it. You know what's funny, I'm so con sumer centric. Yeah, that I'm pretty good at the game because trying to I really want to give you one. I mean, I have the uber and you know there's some losses there. What's a I don't know if I think you mean.
You know you mentioned the biggest successes obviously, but also you know those ones where you.
I got one, I got I got one for you brother. It's not that it went on to explode. It's the one that I thought was going to be massive that was a dud. During that era, I invested in something called Yo Bongo.
I've never heard about that.
Yo Bongo. I invested in because I had been chasing what is now known as Tinder for two years. Grinder had been an app that was doing very well in the gay community, and I fully believed that there was going to be one for heterosexuals, and I for months and years stayed my ear to the ground waiting for the dating app. And there was this app that came out called Yo Bongo, which was because the iPhone had just come out, which was it was positioned as you
could meet people. You would open the app and it would see other people near you that would have the app, and you could make friends. I was like, yeah, friends. I already knew where this shit was going to go, and I wanted to invest in it. So I invested in it. Right behind that, an app called Highlight came out did the same thing and got even more traction. And then a couple months later or a year later, I saw Tinder and I was like, this is it.
I lost my mind. I went to go try to invest and found out that it was incubated inside of IAC in the match group. So I never got a chance to invest in it. But I thought, I told everybody that Yo Bango was going to be enormously big. I wrote a big check by my standards at the time, and it just didn't happen.
Oh, but I mean, this is would be unusual if there's not a single case.
Oh, actually, I'm sorry, Christian. I have hundreds of things that have gone to zero, hundreds of things that have gone to zero. But all of those, many of those, I knew that there was a chance it could go to zero. I was very confident about your bombo.
Right.
We talked about the investments, which is great. Let's talk about your own kind of ventures. You know, all the companies you created. How do you before we dig into this a bit more, how do you measure success for your own companies? We touched it, you know, a couple of minutes ago. Whether it's you know about money, whether it's about recognition, you know, whether it's about the size of a company. What is your measurement of a success?
The first thing king to mind. I was going to jump in, but I want to give you a little room. Is it not going out of business? You know, My first measure is it's still alive. I don't think people realize how many businesses go out of business.
So that's number one. I measure it on financial health for sure. Business is like sports. There is a score so Vayner Sports, Vayner Media, Vayner Watt, which is my new TV production company. They will be scored first by do they go out of business or not? That's the binary part, and then how big do they get? No question, of course, there's all the emotional stuff Vayner Media. How many people come out of the company to go on to have big marketing careers. Nicole at t B being
the CMO and doing well. I have a lot of pride in that. That excites me. So how many winners do we create? Mike at Liquid Depth, Even though I don't think Nicole, I feel more of my thumbprint. I think Mike had a lot of what he had. Maybe there's a couple of things he picked up at vayner Those things excite me. When alumni go on to crush, then there's exits. I don't know if you know this, Christian, I co founded Rezi, the restaurant app.
No, I don't know that.
I invented Rezie with Ben levinthal over dinner right before Christmas that year, and Rezi incubated and lived out of Vaynermedia for the first three years of the company. All right, how did I measure that? It was a multi hundred million dollar cash exit? Very easy to measure empathy wines, which I sold to Consolation Brands. Very easy to measure and a triple win for me. I did well financially. It was only two years old when it sold, so
it was fast. It was a big exit to a big company, and my two co founders both started as interns at Vaynermedia. Like that stretched every inch. So you know, I think those tend to be.
The places awesome awesome. What kind of business you launched do you think where people should talk about more? You know, do you feel that one or maybe some of your businesses that never got the kind of the recognition out there? Anything you know you feel okay that should be bigger or better recognized out in the market. Is there anything?
I don't really build my businesses for the market. Yeah, but I'm very aware of this question, so I'll break it down. Rezi is probably the business that I co founded that is most known by the way outside of me, Gary Vee, Right, So I don't think, you know, it's funny. I don't think I story told that co foundership enough or it's not aware. So that's interesting. I got a big one for you, especially in this time in marketing. I started probably based on my Google searches. The first
influencer agency. It was called grape Story. It was an agency to represent Vine stars and I did that with Jerome jar one of the original Vine celebrities. We signed, amongst others Logan Paul, who we discovered through a campaign to find the next fine celebrity, Rudy Mancuso like it was King Batch we did deals with back then, like
we really nailed it. So Grape Story in Rezi sit in a very interesting place because I don't think people know that about me, you know, the improbable nature of how big of a business I built for my father with no money in that era. I think I have the most pride in but it's probably just thought as like smaller. But you know, listen, I think V Friends is a lot of fun for me right now, Christian, because I think a lot of people think of it as like something that I don't even do anymore because
afts are not as hot or you know. But that one I'm quietly building, and I think that one will surprise people in seven to fifteen years. Look back to this podcast. In the industry, I will tell you a lot of people are flabbergasted of how big Vayner Media is. I don't think most people know how big vainer X is.
I don't think most people in advertising today know that we're a two thousand person global holding company doing you know, hundreds and hundreds and hundreds of millions of dollars in revenue. We're much much, much bigger than our industry realizes because I don't play to the industry. But honestly, all of that is vanity stuff.
Me.
I'm not overly worried about what people think or don't think. I'm much more worried about what my employees think about their happiness. If you ask me, Gary, if Vaynermedia was known by everyone in the industry and you got all the accolades and every ad week, pr Week, ad age at the possible conference, you were awarded the best marketer
to ever live in Vaynermedia, the best agency. All of that combined is half as interesting to me in that my company's fifteen years old and you have almost one hundred people that have worked in it for over ten years, in an industry where people leave after eighteen months every day, that I like the truth. I like real shit retention of your employees for an agency owner should be the number one, two, three, four, five, six, and seven kpi
other than can you make payroll right? Not the amount of people that spend more time in our industry, counting how many can lions the firm has won versus their employee retention tells you everything that I think you need to know about our industry right now.
And how they talk about yourself as a leader and the business you're running. E said, Yeah, well that's the thing with me. I'm such a big personality. I'm a character. I'm not confused by that.
I've watched people be surprised how well my employees talk about me behind my back, and that is deeply rewarding, deeply rewarding, what super rewarding.
Congratulations to this. I hear you know that you're proud of this, and you can be for sure, and obviously that gives you confidence. You know that you do a lot of things right, you know, running your different companies. So let's talk about our industry we are acting in, you know, the wider marketing world. Yes, I think it's a trend to talk about trends. Right. Everybody you know on a stage is asking you how what's coming up? So you're in social media, you and NFTCRE in cryptocurrency
and concentration. Okay, so I've heard you talk about social shopping as a kind of trend. Everybody what a surprise talks about AI. Yes, let's specify a bit more. What is the trend we are facing in the next couple of months.
So look, and you may know you're you're so, you're so in this as well. You'll probably know this probably if you especially if you're prepping a little bit for this interview. I have stayed somewhat quiet so far on AI compared to the way I usually roll. And the reason I've done that is I don't like to talk about shit until I'm really knowledgeable. I've been watching China live shopping for eight years. I've been waiting Christian for
live social shopping like you can't imagine. I've been waiting for the qvcification of social for a long time, and it's immediate. Abercrombie and Fitch right now is a fact did by live shopping and affiliate influencers like it changed their business Mary Roots Organic Like. What I like about why I'm talking about live social shopping is I know everybody on the incredible possible stage that I'm going to take in a couple of months if they sell something, not B to B, but if they or a service.
But if they sell something can be very impacted positively because of it AI as a trend. And I'm gonna say this as respectfully as I can, because I feel like I was getting you know, I always feel misunderstood when I'm rasing the industry. I RaSE the industry because I love the industry and I don't want us to disappear. Yeah, you know, there's a reason people are taking things in house.
We as agencies are not providing enough value. I think what's happening in our industry, with all due respect the Madison Avenue industry compared to the Silicon Valley industry is we have a lot of talking heads talking about AI that really have no idea what the fuck they're talking about. And so I don't want to be a contributor to that. And and it's so big, you know, Live social shopping is a nice transformation in commerce and content creation production days,
and I can get nerdy about it. AI is one of the biggest inventions and innovations in the history of mankind, and so I am trying to be very thoughtful and listening and paying attention. Plus it's moving very quickly, and so you know both. I mean, AI is something everybody who's listening to this podcast, everybody that comes to your incredible conference, should be spending time on. They should be using it, they should be downloading the apps, they should
be understanding it. It is a big deal. It's a big deal by the way, for anyone who's listening that their business relies on search, they should really be paying attention because it's going to disrupt search engines. It's a big deal. But it's way beyond what everyone thinks. It's
going to be omnipresent. It's gonna affect so much. So anyway, I think that people should be doing their own homework on AI, meaning actively using these products, becoming a user of not just listening to talking heads talk about it. I think the two actually mix in. I think, let me just put a string of trends together. I think virtual influencers is going to become a big deal. Okay, I think virtual influencers doing live shopping backed by powered by AI is going to be a big deal for
a lot of our businesses. And so there's just a lot going on. I think I'll give you a less exciting trend, but it's been my passion. I'm excited it's finally happening. I think the reallocation of the P and L budget to organic social creative because of how the algorithms work is one of the biggest trends everyone should
be paying attention to. That's interesting, it's less sexy, it's very narrow, but I cannot believe how much growth my company has had this year where brands are spending more on social organic creative than they are on above the line. And that happened over the last twenty four months in a meaningful way, and it's a back to like caring about practicality versus futurism. I think a lot of people
listening here. I hope they're paying attention to that because that's a big game changer for a lot of brands right now.
So spending time creating experiences being really using that and not just listening to people. What should be the next one I hear you, is this the biggest you know gap you know for traditional corporate leaders that they might not still do understand about the modern business landscape? Is this the case or is there anything else you would give them? What kind of advice you would give corporate leaders?
Is it to spend more time, you know, with what's really going on out there and not just tetting your team, Hey, let me know what you think, but spending their own time doing this.
Yeah. Look, I think being a practition to your point of where you're leading this, being a practitioner is incredible, Like you know, one of the reasons, Like I don't know if people know this. If you go into the history of me, there's two years where there's no Gary Vee content because I wanted to be the operator and I am the operator Vainner Media twenty eleven twenty thirteen, Like, there's very little content of me, very little, it's insane.
From six to today, I am prolific, but there's this weird little twenty four month gap. And do you know what happened, Christian? I was running my business less wine videos, right, less business videos, and at the back end of those twenty four months, it became obvious to me that I was losing my touch. Interesting because I wasn't being a practitioner anymore. I could feel like people would ask me something about
Reddit or Twitter or something. I'm like, oh fuck, So I went all back into Gary Vee and I did everything YouTube and LinkedIn and Snapchat and and it's I believe today, when I'm in again, it will happen. When I come to Possible, there'll be a cocktail hour, There'll be six of us hanging around, and when we get into it, it's very quickly obvious to me that the agency CEO that's sitting there with me that the two CMO those that you know, somebody that like most people
that get senior, they lose or touched to the dirt. Yeah, and so yes, I think that's very good advice. I would also say the following creative's too expensive for our industry and we're getting outflanked. We have to stop paying the production dollars we're spending. And number two, the other thing I would say that I would recommend to corporate leaders is our media spends are being spent on potential reach, not common sense actual reach.
Yeah, and I.
Would highly recommend, if that caught a nerve, for them to look under the hood on how we're reporting against reach and our mmms. And there's some real, real, real vulnerabilities in marketing right now, and the doors are closing in on us with these new brands that are popping up, that are doing it in a contemporary way that don't follow the Madison Avenue playbook, and we need to adjust or we're gonna have some problems.
So becoming or going back to the entrepreneurship in some way, right, you know, when you start your business you do everything on your own. That's a kind of step you know, back and learn more about, you know, than just listening to somebody. So talking about advice for leadership and you know also young people you've mentioned already, you know, being happy about your self awareness. What's the one misconception people
have about what it really takes to be happy? What is the you know, to fulfill you know, what you do and to not necessarily meet expectations of course, and also not not everybody's expectation out there, because you know, if people know somebody, then they should have an opinion on you, but not you know, not knowing somebody and talk about but what makes a difference to be really happy in business?
Yeah? I think this bleeds into life. I believe what and this is a man This has been something I've been fascinating my whole life. Yeah, you know, some people are lucky. And I don't like using the word luck because I think the word luck is weaponized by people that are entitled and not looking to do anything. But some people are lucky. And I'm one of those people where where you're born into your DNA is a certain way, and then the parent or parents that mold you are
a certain way. When people like one of the reasons I'll do a podcast like this and talk about myself quote unquote is I don't think I deserve any of the accolades that are bestowed on me. I think that they are When I get accolades, that's a flattering moment for my parents, not me. So I enjoy this because I know my mom's listening right now because she listens to everything. And I like when you're like, hey, good job, Gary, I feel that's like you're giving love to tomorrow Vaynerchuk,
not Gary, so that I like. So some people are just fortunate. I knew that I was fortunate. I was self aware. I was so emotionally intelligent in the scheme of things. In hindsight, my whole life. I see it a lot of my son by the way, so now I know what it is. He's very empathetic. It's crazy like everything he just feels, and I was that way. I have some answers to this because I've studied for
a long time and I watch people. I believe disproportionately the secret to happiness and business and in life is simplicity. You know, we're getting to know each other more and more Christian. If you really knew me, let's say we really grew up together, you really knew me, well, you would know. And twenty people know this about me? Is
I care about nothing professionally? It would I'm telling you, brother, I'm telling you, it would fucking stun you how little fucks I give about Gary Vee, Vayner viv It's shocked. I am so detached emotionally from my professional career. It's almost like I don't know if it's brilliant or fucked upness. I don't know what it is, but I will tell you that the only thing that I give a shit about actually is are the fifteen people I love the
most on earth, healthy and alive. And I'm crippled when there's a health scare, and I'm light as a feather when there's not. I have so much adversity. I'm a human being. I'm forty nine years old. I have things in my personal life. I have a billion pressures in business. There's not a day in business where I don't have fucked up news. We let go of somebody today that I care about deeply. It's fucked with me for three months. Three months, this has been a heaviness on my chest.
It's hard to be a leader and to be out there, and I'm a public figure, all that judgment, all those whispers behind your back, like all that stuff. But the reason is it's humility. I don't think I'm that important. I think I'll die one day. Maybe I'll get twenty four hours on whatever the social media, if social media even exists at the time, I'll get some flowers, right, and then everybody will move on with their life. My family will care longer. And so I think humility and simplicity.
I don't need stuff. I don't need a fucking private jet to impress anybody. I don't care if people think I'm good, bad, or indifferent. I want them. I care if you know me, By the way, Christian, I care more today what you think about me than two years ago, because we've interacted more that matters to me. But right now, I promise you, Maddie, who's sitting right heroes worked with me. Now what Mattie nine eight years, I really give a lot of I care. Maddie is not as important to
people in the advertising world as Christian is. But I can tell you right now, I could give a fuck what you think compared to Maddie, because Maddie knows, and so I think the secret to life is detachment from bullshit and deep attachment to love.
Which is a huge achievement if you allow yourself to think like this, I would say. But also in acting in business, you know, in so many ways to give a shit on you know, other's opinion in that way. Not many people can do this, as we all know. We know we are pressed into a framework, you know, especially when you work for bigger companies, et cetera. But you're your own boss, and maybe that's also one of the key differences.
Yes, but I'm my own boss that plays with the market, right right, Like you know, it's a different version. Yeah, there's many days when I wake up and I'm like, you know, being judged by three random people that are my bosses. Sounds really good right now, versus you know, the field of society, you know, so like you know, there's different versions of it, but yeah, simplicity and humility, and people say it, but then they don't act on it.
I've unfortunately had to let go of leaders through the years who say they care about people, but they don't. They're posturing, they're politicking me, they're trying to appease me. But you know, I tell people, I mean, I tell people all the time, don't worry about what I think about you. Worry about what the people who work for
you think about you. Maddie Will if you hung out with Maddie, she would tell you it's wild how senior some of the people have been that have gotten fired here, the leaders, because they just if you can't get along with the boys and girls, especially the ones that you're leading, you're not for me.
Yeah, Gary, I have a last one. Please, You've accomplished so much already. What's one thing you still feel, you know, like you you must do before you call it a day, professional whatever, whatever?
Overall, I'd like to I'd like to become even a better father. I think I'm a great son, like the best I feel like, I feel like I can walk. I can't wait to go to heaven. I expect God to give me like best Son Ever award, But I feel like there's more to be done as a father. I have a fifteen and twelve year old. I want
to really crush that and do more there. Number two. Professionally, I'd like to create a company that has the most amount of offspring from the company that went on to build companies that are similar to mine, which are wildly successful but also nice to their employees. I'd like to reframe the company. Actually, I'm going to give you a slightly different answer, but it's the same answer. Before I'm done. Professionally, I would like to rebrand nice Guys Finish Last to
nice Guys Finish First. That's what I would like to do.
That's a great statement to the end of our conversation today, and to your first point, I'm pretty sure and I know that he's a great son because you're a great father, so that's for sure. And I can tell you because I have a son as well as you know, and I feel in a very similar way. So Gary, that conversation was nothing short, but incredible. Thank you so much for your time, your energy, insights, and that honest conversation.
And I'm sure you know many of our listeners will walk away ready to hustle Haara and think bigger, appreciate manness.
Let me say one last thing. I assume we're going to put this out before the conference, right, that's a plan. Yes, okay, good? Let me just send with this please please please, Because I see it in your eyes, which is why I approach so many people. I'm going to be around quite a bit. I actually am so happy this is happening because I get to say it out loud. I send this to you in person. Now I want to say it out loud. The conference you've created has become the newest,
most important conference in our industry. That's an incredible accomplishment in what is fucking two minutes? What is this year?
Three?
It's going to be the three yees.
Correct, It's absurd what you've become published you and your partners. I'm going to be around a lot more this year because I'm allocating more time, because it's that important. If you happen to see me, like walking in the hotel wherever, and you want to say hello. Please say hello. Relationships are everything.
We make sure you have to connect with the right people and then connect with the right one and this is you for sure. Gary, appreciate you. Thank you very much for mind see you by. Thanks for tuning in everyone. Once again, I'm your host, Christian Moho. If you have a question or suggestion to me, reach out, send me a d M on LinkedIn. If you're courious to learn more about Possible, sign up for our newsletter, or if you want to join us at the Possible Show in Miami,
visit possibleevent dot com. Possible Now is a co production of iHeartMedia and Possible. Our executive producers are Ryan Martz and Yasmin Melendez. Our supervising producer is Meredith Barnes. Special thanks to Colleen Lawrence Mac from our programming team. Our theme music is composed by Anthony Keticoli. For more podcasts from iHeart, visit the iHeart app Apple podcast, or wherever you listen to your favorite shows.