In Search Of Excellence - Gary Vee: $2 Billion Dollar Taco, Live Shopping, and Customer Service | E171

Episode Date: August 16, 2025

Gary Vaynerchuk, commonly known as Gary Vee, is an influential entrepreneur, speaker, and internet personality, best known for his expertise in digital marketing and social media. Starting his career in his family's wine business, Gary's innovative approach to e-commerce and content creation catapulted the business from a local enterprise to a national leader in wine retail. He later founded VaynerMedia, a leading digital agency that services Fortune 500 clients across the globe. In this episode, Gary shares his unfiltered insights on the dynamics of building and scaling businesses, the evolution of consumer engagement, and the relentless pursuit of hustle. He opens up about his journey from a Belarusian immigrant to a global business mogul, reflecting on the impact of his heritage on his work ethic and entrepreneurial spirit. With his characteristic candor and deep passion for empowering others, Gary offers listeners not only a glimpse into the competitive world of digital marketing but also imparts profound lessons on perseverance, vision, and personal branding.Timestamps:00:00 - Gary Vee discusses the early influence of social media on his content creation, specifically Twitter.03:02 - A discussion on strategic moves in poker and their parallels to business decisions.06:02 - Gary shares his experience of working in his father's store during college and the lessons learned.09:02 - The conversation covers the significant impact of actions in leadership and business.12:02 - Gary talks about the inception of his agency and his disbelief at the scale of corporate engagement in the late 2000s.15:05 - Reflections on personal moments, including a honeymoon in Hawaii and the settings that influenced his life.18:05 - A hypothetical scenario is discussed where a major social platform is forced to sell, reflecting on the potential impacts.21:06 - Discussion of missed opportunities and the financial implications of quick decisions in business.24:07 - Gary Vee emphasizes the power of word-of-mouth in marketing and personal convictions.27:09 - Analysis of the cost-effectiveness of Super Bowl advertising and its comparison to other marketing platforms.30:10 - Advice for professionals feeling dissatisfied with their job, stressing the importance of commitment and effort.33:10 - Gary discusses the importance of setting goals and the effectiveness of writing them down.36:12 - A personal reflection on family dynamics and the distribution of affection among siblings.39:15 - Gary shares his views on retirement, emphasizing his desire to never stop working.42:18 - Thoughts on legacy and giving back, including advice Gary would offer to his younger self.In Search of Excellence Podcast - with Randall KaplanListen to this episode on the go!Apple Podcasts: https://podcasts.apple.com/us/podcast/in-search-of-excellence/id1579184310Spotify: https://open.spotify.com/show/23q0XICUDIchVrkXBR0i6LOne-on One Coaching: I coach a select group of high achievers on how to elevate their careers, grow their businesses, and unlock their full potential. Apply Here = https://www.randallkaplan.com/coachingFollow Randall!Instagram: https://www.instagram.com/randallkaplanTikTok: https://www.tiktok.com/@randall_kaplanTwitter / X: https://x.com/RandallKaplanLinkedIn: https://www.linkedin.com/in/randallkaplan/Website: https://www.randallkaplan.com/Coaching and Staying Connected:1-on-1 Coaching | Instagram | YouTube | TikTok | LinkedIn

One of the first videos I ever made was called Facebook Should Be Worried about Twitter. Because Twitter just come out, I was again fascinating by it. That video went viral. Blaine Cook was the first CTO. I met him for a taco at South Buy, and he told me he was quitting and selling every share and did I want any. First, I tried to talk mad of it. I said, I think you're making a huge mistake.

Second, I could see he was making an emotional decision. A couple weeks later on emails, like, do you want to buy it? I'm done. I'm like, Blaine. He's like, I'm done. And so me, Fred Wilson and Kevin Rose bought up all his shares. That was my first investment. And he left $700 billion and $2 billion on the table.

That's right. Just staggering. Several months later, my video went viral. Facebook, Dave Morin asked me to speak at Facebook. Zucks was there. We had dinner that night. We hit it off. We started to get to know each other.

And his sister, Randy, called me. Mark wanted me to call. Our parents are looking to sell some shares. They're going to buy a nice home near us in California. Would you like to buy some Facebook equity in? I literally took 80% of my savings that invested in Facebook. You're listening to Part 2 of my incredible interview with Gary Vee. If you haven't yet listened to Part 1, be sure to check that one out first.

Now without further ado, here's part 2 of my awesome conversation with Gary. You took a company from $3 million to $60 million in a short amount of time. You saw things that people didn't see at the time. You bought Keywords, AdWords, wine was $0.5. And then after 9 months, went to $0.10. So what did you see that nobody else saw as really a first-mover advantage but I think is so important sometimes in building businesses? It's what I see right now with live shopping on social.

I'm going to assume that I'm going to just look around the room, that people here know that TikTok shop exists, that people sell things on TikTok. Huge. I'm going to assume that people here know that, or this might be smaller, but you might know what whatnot is, live shopping. I'm going to assume that people in this circle know that China's been set. selling stuff on live social for the last seven years at scale.

I'm going to assume that people are listening and watching by just saw the viral video of that woman with the handbags who does $8 million just by doing this. I know that all to be true. I also know that almost every single person in this circle right now is underestimating it. I know that 99.9% of the people who are watching this right now

don't understand it the way I do. I understand it for what it is, which is it's going to be massive, massive. That if you ask me right now, of all the optionality in the world of how to make money in the next five years in America, that live shopping is at the tippy top of my list. That's what I saw with websites, email, and Google AdWords. I don't think I was the only person that saw it. I just think what I'm very good at is I view these trends like poker. And I view live shopping on whatnot and Fanatics

Live and TikTok shop and Meadow will have to do it because it's going to get too big. I view it like having the nuts in poker. I feel like I've got the best. Like, I know it's the best hand. And so if you know you have the best hand, educate me your poker players. You go all in. Because you've won. Sure, they may fold, but you go all in. I know that. That's what I do for a living. What I'm good at is knowing what humans are going to do. And I know when it's the biggest hand, the best hand. And so the reason I was able to build my daddy's liquor store was having a website was better than having a catalog, right? I wanted to compete with Sherry Lehman's, Zaki's, Morels,

Sam's Wine Club in Chicago, K&L in California. I wanted to have the specs in Texas. I wanted to have the best wine store in the country. What were those stores doing when I was in high school and college? They were buying full-page ads in a Wall Street Journal and the New York Times Wednesday dining in section, and they were sending catalogs in the mail. I outflanked them by having a website and having a email newsletter.

So my email newsletter in 1998, when 94 Dominus came out and insignia, I would email everybody and they would buy for me. They would get the catalog from Sherry Lehman's four weeks later because catalogs are slow. Email is fast. Catalogs are expensive to make and ship email was free. So even though I had no money, I outsmarted. them by knowing where the attention was because Wall Street had moved to email, but not everybody caught up. I believe social media is now, in my brain, 20% of all social media content is live shopping.

It's not yet, but it will be. And so I'm going to move fast during this era on it. That's what I did with email, with having a website at all, and then finally the big final atomic bomb outflanking everybody on Google AdWords. You need to have great customer service to build any business. So talk to us about this crazy story about this woman who wanted a case of Berringer White Zimvedel in the two and a half hours still. This is such a, so anybody who owns a business, if you're listening right now and you want to make a point, a culture, do something in action. Don't make a fucking poster and put it in the hallway.

Don't tell a story that happened in the past. You and I have enough war stories where we can tell the kids. Do an action. So I was building this store. We're now on fire at this point. This is later. This is like 2002 or three. We built a new store.

I grew up in a smaller store than we built a big store as I was growing the revenue. I am the man on the floor. And this is the holidays. When I tell you from 18, to 34 years old my December and I mean all the first 24 days of December

outside of when I was in college but even that I came home way early because I was barely going to class I would spend from 7 a.m. to 10 p.m. on the floor of my dad's liquor store that was prime time especially pre-internet you know

we are in the midst of one of the busiest days in the history of the store. And now we're doing internet business and we get a phone call in the order department. I'm running upstairs downstairs. I'm keeping an eye on the internet and the store and I'm fucking a maniac.

And we get this call from the son of this elderly woman. Wasn't even her. That her case got misshipped and this was like December 23rd or 2nd or 1st. I don't remember, put it this way. She lived in Jersey and that's one day delivery and I knew that if we put it back in the mail, she wouldn't have gotten it for Christmas.

And he made a big to-do that she needed it for Christmas. I remember to stay like yesterday. I knew that there would be a day that I wasn't going to be at that store. I knew that I was going to have to build my own life at some point because I knew my dad viewed it

like an immigrant, which is, oh, this is your business, but it's really not. Like, I can't buy a home because I have no equity. Like I couldn't, you know, like I would inherit it when he would pass.

Well, I'm fucking going to be 50 and 15 months. and so my dad's still working every day. So you can imagine I was smart enough, thank God, at 22, to be like, I got to do my own thing. But I remember I needed to do things because once I was gone, I wanted them to know how it was built.

I knew then. So even though I'm on the floor and generating $10,000 to $20,000 an hour, just me personally, on someone like you that had high net worth that would come in and be like, I need three cases of high-end wine for the holidays. I was that guy

I decide to make a huge to do about this case of Berringer White's infidale it's snowing like the weather's bad and I decide to grab a case from the basement and I tell my inner team just like this in a circle I'm like I'm gonna go deliver this because we have the best customer service in the game and they are stunned

I never I don't go to pee for 15 hours during the day that's how busy it is and how committed I am and now I'm going to drive to Bergen County. Isn't that an hour? And that's without snow? The fuck are you doing, Gary? And I said, this is, I just remember that this was my moment to make a point. So I did it. I drove. I enjoyed it. I listened to sports radio on the way. Got back. Everybody was stunned. Everybody was sweating. Brandon was like, you missed Mr. Thompson and Mr. Smith and like all this money was lost. But it became a story. To this day, that story is

being told to employees at our store about customer service, I might have lost $20,000 in sales that hour, but I've helped my dad make millions since. And I think more companies should understand that actions carry enormous weight. And I believe that every leader that's listening right now should think about what they care about most and instilling in their company

and then should go out of their way for the most hyperboized executions of those things so that it becomes lore. I mean, look at this. I literally did that action. And here I am, 20 plus years later, having the luxury to tell that story on an important platform like this. Think about that. This is the meta of the thesis.

It's how you build it. It's how you fucking, how do you think everything built? Everything's based on stories. Why do you think religion exists? December 2008. And you have a meeting at ESPN and your brother, AJ's graduating BU. And you walk out, and there were a couple of things. What did you walk out with and then what happened next?

I hope you're enjoying this video so far. But before we jump back in, I want to know if you've ever thought about what you need to do to reach a nice level of success in your life. Over the last 25 years, I've been an advisor to more than 50 companies. I've invested nearly 100, including Google Lift and Seagate. And I also co-founded a company that today is worth more than $15 billion. I've been incredibly blessed in my journey. And at this stage in my life, I want to give back.

I want to share the lessons I've learned so you can reach incredible success way faster than I did. In my own journey, I've learned that having the right mentor is a massive advantage to achieving our goals. I'm hugely passionate about mentoring others. I'm looking for a few hungry entrepreneurs are excited to take action on their journey to incredible future success.

So if that's you, I've got an opportunity. In the description of this video, there's a link where you can apply to work with me. All you need to do is answer a few simple questions, and if you're a good fit, my team will reach out so we can build a game plan. together. All right, now let's get back to the video. Well, I first worked out with $5,000 and I couldn't comprehend how I, you got to remember at

this point I'm still making less than $100,000 a year, even though I'm 33 years old and built this huge business, immigrant life. Again, if you don't live in an immigrant business, you don't understand, but like, I built this huge business, created hundreds of millions of dollars in revenue over that course of a period of time, and I'm still making very little. My dad's making super little, too, but he owns the business. So I'm starting to think about my next chapter, my brother's about to graduate. And we're bouncing a lot of ideas, daily fantasy sports, which probably would have done well,

something that looked like Groupon and Living Social, that probably would have done well, something that looked like BuzzFeed, that probably would have done well. But those would have all taken time to build, and I really didn't have any money, and AJ surely didn't, because I just invested in Facebook and Twitter,

so all my liquid was gone. And so consulting, getting to, paid for action was a better cash flow option and it's amazing and i get this random email because at this point i'd massed a lot of followers on twitter but it's still early it's so first couple years of twitter and espn asks if i could come in and consult on how to grow their um social their twitter specifically what year was this this is 2008 steve bernstein was CEO or he had It wasn't at that level. It was way lower down.

It was three to four levels below that, maybe five, if I'm thinking properly, of their org at the time. It was marketing, but it wasn't even like, it was definitely not the CMO, let alone the CEO. And I don't even think it was the number two in marketing. It was a lower level, but the guy had the ability to write a $5,000 check, which is nothing for a corporation. So it was lower level. Anyway, I go in, I sit in a room like this, I consult for a couple hours, I enjoy it to no end. And I leave, and literally it's like old school. Like you got a check back better.

And I call my brother as soon as I'm in Midtown, because it was in Midtown or something like that. I call my brother. I said, I got it. We're going to start a consultancy. I didn't even call it an agency yet. It wasn't really even an agency. But I couldn't believe that it was 2008, going into 2009.

And I couldn't believe the biggest companies in the world didn't understand social media because I'd been committed since 2006. And that's probably one of the first time. I've learned about timing. I'm just talking about it right now with live shopping. I'll say it again. I don't think I'm Andreessen Horowitz invested in one not a long time ago. I'm not a genius. I just feel like in this

nanosecond that everybody's underestimating how big it's going to be. And I didn't understand that. I didn't understand that it would take that long for people to get it. And as it got bigger, it got slower, right? I didn't know that. Entrepreneurland information and action goes faster than it does in corporate land. And so I was like, wait, there's an opportunity.

They still don't get it. And so that's why I decided to start VaynerMedia. Which is also blown out. Yeah, I mean, VaynerMedia started in the conference room of Buddy Media. Fred Mike Lazaro. Yes. And you got equity for building a website. I got equity for giving a quote, not even building in that website.

And they sold the company salesperson for a billion dollars. Yep. That was a good outcome for a quote. For me, I did extremely well. I literally made seven figures to give a quote, because at that point, I'd written a book called Crush It. That was the first time I'd hit the scene outside of the wine world. And very quickly after there, I was starting to be viewed as an angel investor

with the Super Angels, Tim Ferriss and Dave Morn and Chris Sock and Kevin Rose and Travis Calcutting. And I was definitely in the game, Calcanus. I was in the game in that era, 2006 to 2012. It was a very good era from my personal brand with books and speeches and investing. And VaynerMedia is something I'm very proud of. We literally started it in a conference room. And it's a $350 million a year revenue business now with, you know, 2,000 plus employees and we're definitely the most progressive contemporary agency in the world.

And it's also been the foundation of my other behaviors. I started Rezi inside of there with Ben Leventhal. 2014. I started Empathy Wines, which I sold the consolation with me and John, two former interns in that company. 2019. And then V-Friends, which I believe, and it's fun to put this on video, to look back on in 20 or 30 years from now, but I'm in the midst right now of building an intellectual property.

I'm very affected and inspired by Pokemon being worth $100 billion. I do not think people realize how big that company is. I also am very inspired by Jim Hudson, a real creative force who really wanted to leave a deposit of good on the world. Fraggle Rock, Sesame Street, Muppets. And so, yeah, I'm building V-Friends, and a lot of the talent that works inside of V-Friends came from V-Ner. So Vainer has been an incredible company,

but it's also been an incredible incubator of talent and osmosis of, like, how I want to do things, and I'm very excited about it. I'll tell you back in my life in 1999, I'm on my honeymoon with my first wife in Hawaii at Huala Life, I don't know if we've been there or not. Oh, actually, I have. I spoke to Brand Jordan there.

And this guy next to me is reading a magazine that no longer exists, the industry standard. And I said, hey, are you on the business? I said, yeah. I said, what's your name? I said, my name's Ron Conway. And so talk to us about Ron. Ron affected me too.

And then as part of the story, tell us about how making bad decisions on emotions is a terrible strategy. and you can talk about plain cook from Twitter and how you got that deal and then talk about Facebook, Mark, Zuckerberg, your dinner and then his... You got it. So that whole Silicon Valley era for me started with,

so now I'm right about email, I'm right about the website, I'm right about Google AdWords in 2005, and here comes YouTube. And I see that, and I'm like, fuck, I'm going to build my dad's store with this. So I've used the tool of web. I've used the tool of web.

of search and email, and here comes video online, and I start using the tool. I start WynobTV on February 21st, 2006, less than a year after YouTube comes out. And I want to take a moment right now and give a huge shout out to Eric Castor. Eric Castner was my lead developer. One of the most progressive things I've done in my life was the day I started working in my dad's store full time, May of 98, I told him from the day I started, I will take nothing in my salary, but we need to hire a computer guy. That's what I called developers back then. We need to hire a computer guy.

And by 2000 or 2001, I was able to finally get to a place where I was able to hire Eric Castor and then later John Casamantis, who's still our CTO. And we're a fucking liquor store in New Jersey and I have literal developers full time on my staff. It was so progressive. It'd be like if I hired astronauts right now, like it just made no sense. Anyway, I want to give a shout to Eric Castor because without Eric Castor, a lot of this does not happen.

He was the one that sat closer than you and I are sitting right now at my desk and was like read TechCrunch, read Metafilter, read, read by web, read, you know, dig. He was the one that showed me Web 2.0. And during that journey, he showed me YouTube, because I asked him two years earlier if I could do videos on the site and he said, no, too expensive to host. Now we found this. They were hosting it. So now I'm doing YouTube.

I explode. This is where my career really takes a turn. The wine show explodes. and then I'm now really starting to get into this tech stuff and how do I use it to build a wine store, but it's still wine store, wine store, wine store. And then Google buys YouTube. And one point, you remember this.

That number, I don't think the kids can, now everything's inflation. You remember that number? 1.45 billion. Do you remember how everyone reacted? It was insane. I'm saying it right now because I want you guys to hear and be affected by it. It'd be as if you woke up tomorrow and TikTok,

was forced to sell and sold for a trillion. It's like you couldn't, we didn't see numbers like that. Yeah. Everything was, big numbers were hundreds of millions. I mean, Flickr sold for 40 million to Yahoo, and that seemed like a trillion. Flickr was the precursor to Instagram.

Anyway, I'm just like, holy shit. And now I'm a little bit older, and I'm reading more business magazines, not just wine, and I read a Wall Street Journal article about the sale because I was fascinating. I felt different this time.

I was like, fuck, man. I feel like I know, I feel like my talents are not being maximized. I'm using these things to build my dad's business. There's got to be a way. I just felt different. I was just reading everything about it. And one article specifically, it references Ron Conway. And it says, angel investor, I've never heard the term in my life.

Angel investor, Ron Conway made a quadrillion dollars. I don't remember how much he put in or what he got, but it was staggering. It was like, for his $100,000 investment made $4 million. Or it might even be, it was just staggering. I don't remember the details. I just remember immediately going from print because it was, I think, the journal to computer and Googling, not Ron Cotway,

Googling the term angel investor. Googling it. Ironically, very apropos. And I'm like, huh. And I literally, again, said to myself, I'm going to be an angel investor. I'm going to build up some savings. I had some savings at that point.

and one of the first videos I ever made that wasn't a wine video was called Facebook Should Be Worryed about Twitter because Twitter had just come out I was again fascinated by it and I promised myself after the Ron Conway article that the next time I felt it that I would invest

and the next time I felt it was Twitter and that video went viral Blaine Cook was the first CTO of Twitter Developer. Developer. Thank you. And I met him at South By, because now I'm going to these conferences, and he, Twitter, I don't know if you, were you in the mix? You remember this? I was in the mix, but not. Did you invest in Twitter? Do you remember that Twitter would go down all the time? It was, yeah. Down all the time. It was the hottest app in Silicon Valley, but it was down, down, did not work all the time. They did Ruby on Rails early on. It was complicated. He was getting so much heat. I met him for a taco. at South Buy and he told me he was quitting and selling every share

and did I want any first and I'm really proud of this back to being a good person first I tried to talk mad of it I said I think you're making a huge mistake second I could see he was making an emotional decision and he just went the whole way

and a couple weeks later on emails like do you want to buy it I'm done I'm like playing he's like I'm done and so me Fred Wilson and Kevin Rose if I recall properly bought up all his shares that was my first investment and then a couple of months And he laughed $700 billion and $2 billion on the table.

That's right. Just staggering. And then several months later, because I become friendly with my video went viral, Facebook, Dave Morin asked me to speak at Facebook. Zucks was there. We had dinner that night. We hit it off. We started to get to know each other.

And sister Randy called me one night when I was in Miami at a speaking engagement said, our parents, Mark wanted me to call. our parents are looking to sell some shares, they're going to buy a nice home near us in California because they were still in Connecticut. Would you like to buy some Facebook equity? I said, absolutely. I literally took 80% of my savings and invested in Facebook. Congrats. Thank you. I've never sold a share. I promised myself that night that as long as Mark was the CEO, it never sell. You've invested in over 100 companies. What do you look for when making an angel investment? Early on, I went for the horse. Then I went for the horse. Then I went

for the jockey. Now it requires both. The horse was the idea. The biggest mistake I made as an investor early on as a kid, a kid in my 30s, was I, if I liked the idea, I could see how I could run it to success. I didn't realize I was a good operator yet. Then I learned that that wasn't always working. Then it was about the kid. But even with the best operators, if you're operating a bad idea, that also will work. So now what I look for in angel investing is the jockey and the horse, the operator and the idea. And so what's the best way to pitch you? I read what you're going to say. And what I would give is my answer is very different. What you're going to give is your answer? What's your answer? My answer would be to come in prepared. And if you have to get in the

door and you don't know me, you can create a ridiculous PowerPoint presentation that blows you off of your chair. And I'm good on the preparation. We'll talk about that in a few minutes. But I prepared materials for people that they have to respond, right? Because you know when you open this document, holy shit, did this take 40 hours to prepare or more? This thing's like a Rolls Royce. It's a Ferrari on steroids. And if someone's putting that much work into it, it shows the amount of thought, progress. It's brilliant. I've received a few of those sometimes. A lot of my deals, most of them, 99% will come from people I know. Yeah. Right. And so it's a self-selecting process. Of course. But every now and then I get something ridiculous in the mail. We've never had

invested in a cool deal like that, but we've come very, very close. Interesting. Yeah, mine's the opposite. And this goes back to self-awareness. This goes back to like, you got to know yourself. Like, I always say everything works. Everything works. Like, there's a version of success and happiness that comes in so many different sizes and shapes that it can work. For me, I don't even consume decks. My team knows this. Like, to really prepare for me, I need to have the dialogue. I need to have the feel. Like for me, at this point, to your point, so much comes from word of mouth, different angles. But what really gets me is if somebody says something that I believe in, that I can follow up with a couple of questions, and they can answer it. For example,

what cliche happens to me is I make a big stink on something like this about live shopping. Now I'm going to get pitched. This is real. I was thinking on you were saying that. I said, oh my God. I'm going to get bombarded. Yeah. I won't look at most of those emails. I won't go for the Rolls-Royce deck. I will go for the person that finds me somewhere, or I get a meeting through a person because I want to, if somebody co-signs someone, I'll take that meeting.

But it's not what they say to me. It's my follow-up question. I really tend to invest in things I know. More and more, by the way, as I get older. And so I know what I'm talking about with live shopping. So to me, I enjoy the back and forth. because the other thing I think I do well is push. I push well in dialogue to like real places,

and most people can't answer those real places. You know this. A lot of founders are very good at the surface level conversation, but when you poke and prod, they fold like cheap chairs. What the craziest thing is, you ask someone about, they talk about run rate, run rate doesn't apply to the cash in the bank. So I always ask, what are the gap revenues? You know how many CEOs know what the gap revenues are the last three years?

less than 1%. And for me, the meeting's over, right? I mean, if you don't know your finance as well. And so for me, you're referring to things that are a little bit further along. I do so much early state that to me, it's almost a reverse of, I love you for that. That just, I wish people knew how nerdy I am with business. That just got me so fired up. But that's obviously a little bit of a later stage company in that scenario. For me, because I'm so intuitive of consumer behavior, I get excited about them having to answer pre-revenue, since I do such early stage. real questions about consumer behavior. And I'm so in the traffic.

One of the reasons that Gary V brand still lives and I run the agency is I never want to be away from the dirt. Your visa marketing and day trading attention. And we'll go back to Jab, Jab, Jab, your favorite number five. So talk about that book in particular and what you want to call it. And I know you want to call it something else. So what we did is we actually made you a new book. I'm so hyped.

Here's a new book. Actually, jab, jab, jab, jab, so congratulations on your book. Thank you. I love that. That's awesome. It was supposed to be left hook, by the way. Jab, jab, jab. Jab, jab.

I was good. I was, so this book I wrote because I realized no one understood what was going on with content on the internet. By the time I wrote this 10 years ago, 2014, there wasn't a lot of science around the art of a post. I believe as we sit here today, my friend, that the best social media, organic post, just post on your account, is a more important form of advertising than any television commercial on television today outside of Super Bowl. The individual post. You said the Super Bowl,

which costs $233,000 per second, is the greatest marketing spend on TV. It is. In America. In America. Here's why my newest book, Day Trading Attention, I do believe that I sit at the top of the organization that is the best marketing firm in not wasting a penny on advertising and getting the most for a penny. And that requires a lot. I, Gary, and Vayner X, the holding company, cannot get 130 million Americans, cannot get 130 million Americans to consume a video for 30 seconds for $8 million. But the Super Bowl can. No meta, no Google, no all the other things influencers, TikTok, there's no combination that can get there like the Super Bowl can. The problem is if your video's bad, you just waste it all the money. The creative is always going to

be the variable of success. But buying the attention, yes, in buying the attention, the Super Bowl is the best. Let's talk about ingredients of success. What's more important? Work ethic, talent, or passion? Yes. Look, you know this. I mean, Look, the reason I like work ethic is it feels very controllable. It's like working out. Like, you can get there. Working out came really not natural for me. I didn't do it at all until I was 38.

Like at all. I didn't have a muscle my fucking body. So if I, who despises it to this day, can get to a level of discipline that gets me there, I believe people can do the same professionally. I also believe that it's a lot easier to do that level of work ethic when you're actually passionate about it. So it's a very, the reason I answered the way I did, yes, all three, different for every one of us in here. But of the three, work ethic is controllable. And it's something that I get scared that people try to downplay.

Look, as someone who's unfortunately been tagged with hustle, culture, and things of that nature, I have been consistent. Had Ariana Huffington on the Ask Gary Vee show a decade ago. I believe in sleep. I just think work ethic matters. Not to burning yourself out and being sick. That's stupid. I am worried that people are using health and wellness and mental health and all these great things that are important as weapons to create entitlement or to create

laziness or to justify non-action. and I think it's a mistake. I believe that work ethic is the most important ingredient in success of our success, because as you said, you can control it. I have something called Philo, first and in, last out, and I do a lot of coaching. I know you do as well. I tell every young professional, even mid-professionals, that come to me, hey, I'm not liking my job, whatever.

If you're the first one and the last one out of great things are going to happen to you no matter what. I think that's exactly right, because even if you're in an environment that doesn't reward that, you're going to learn that it doesn't, instead of leaning on excuses, which will empower you to make the tough decision of leaving. I fully agree with you on that. Let's talk about my favorite topic, which is preparation. I'm writing a book called Extreme Preparation. I always want to be the most prepared person in the room. How important has preparation been in your success?

And are there any examples you can give about your extreme preparation leading to something successful in your career? It's my entire life. So my favorite thing And Sid just stepped out But Dustin's here So I want to look at him Dustin actually probably knows It's better than Sid

The thing that baffles All my top executives When they start in my company Is I go into meetings Cold And dominate them They think I do no prep They make me huge decks

And because the way we do our decks They can see I didn't open it I walk into the meeting Brand new client And they are baffled It's one of the best compliments I get. It's so flattering. They are stunned.

It is by far the number one chatter conversation of VPs and above when they first joined a company asking all the other OGs. How the fuck did that just happen? It's because I only am prepared. It's the only thing I do. The reason I can walk into Nike or Smartwater or a T-shirt brand or Lexus or any brand and crush a meeting is because most businesses are not that complicated. I can promise you that what smart water wants is to sell more smart water.

And if they're meeting with me, I'm not talking about supply chain. We're not talking about other things. We're talking about demand creation. So I think preparation is the only thing. The reason I do such narrow things is there are the things that I'm preparing on at all times. The reason I have Vee friends and Wine Library and WineTech.com and Gary Vee is I have to actively work on the craft of marketing and demand creation to feel. like I have any ability to talk to anyone about it. I'm a full practitioner. Of the moment, I can speak about live social shopping right now with the expertise I am because I sold $130,000

worth of clothes on a live stream a week ago. So I think you're on to something very powerful. I would argue that the bad version of it is school and the good version of it is sports. I'm always prepared because I never talk about anything or act on anything or involved in anything that I don't actually do. I think some people study, but they're not about it. And that's where the vulnerability, even with prep work, comes in because when people start poking and prodding, you start going to 301 instead of 101 level preparation. So I think the ultimate preparation is to actually be a practitioner of.

So I love entrepreneurs that are investors. They lipped it. How important is setting goals in our security? And do you believe in writing them down one three, five-year-seven plan, seven-year-prone? I think about this one a lot. So, again, I play it a little looser, as you can tell, than black and white. Obviously, I've had a goal since fourth grade of buying the New York Jets. I'm sure it's had an impact on my success.

Right. There worth $7.3 billion today. And it's moving fast with private equity coming in. Right. You're going to buy them one day? I think so. My intuition now is that as I get older, I'll start to put myself in a position for extreme wealth creation if I want to, but I'll be honest with you, just to be very clear, the chase of it

is the great enjoyment. It's a lot of fun to chase that fucking football team that's pissing me off right now. Anyway, you know, I think people do it different ways. I've learned that I'm not a reader and writer. I'm an audio and visual guy, and so I talk to myself a lot about things I want to accomplish your personal life, professional life. Yeah, I think knowing where you're going is a good idea. But I would argue that the ability to adjust and not be rigid to them is equally, if not slightly more important. If you're going to do this thing in five years, but clearly something's happened, putting your goal on a pedestal when it does not contextualize the truth of your life at the moment you're in right now is a vulnerability.

I think people look at you, they look at me, they look at all these other tech people who have done very, very well. And they say, oh, my God, that person is rich. They have nice things, et cetera, et cetera. And I think everyone wants to be a billionaire. Not everyone, but a lot of people. And I think that's the motivation. So what's your advice? And look straight to the count. I mean, I talk about this until I'm blue in the face. People who are motivated by money are generally not as successful, and they're generally not always happy either. Either, you know, listen, I've read, I think you know this. I talk about this at nausea. Yeah. I'm going to say this to the camera.

I'm extremely deeply empathetic that the response to this for most people is cool, rich guy, but I'd like to find out. Like, fuck you, easy for you to say, I'd like to find out. We have the luxury of spending time with people that have it,

and we know how dark some of their lives are. There is just no correlation in any kind of common sense way of money and happiness. It just doesn't. It's black and fucking white. So what I would say is, God willing, if that's what you want, you are able to earn, not be handed, your way to a place where you have it. And I'm going to tell you right now, when you get there, you will see how right we are, period.

Your dad, at one point, said you're going to be the next Oprah, and a VCon, he wears a hat that said, I'm Gary V's dad. Yes. And he's so proud of you. How does it make you feel? Unbelievable. Other than I wish he wasn't so one-dimensional and spread some of that love to my siblings sometimes, it's unbelievable. And my dad does it very publicly, and my mom does it very quietly, and they both mean the same.

Making my parents proud is probably my strength and my weakness. It's a big currency for me. I really like making them proud. It feels really good. We're at the end of the show, and I always end it with a game called Film of Blank to Excellence. Are ready to play? Ready to play. The biggest lesson I've learned in my life is...

Losing is the thing you should always strive for, because it makes winning a lot easier. My number one professional goal is... To buy the New York Jets. My number one personal goal is... To have everybody that I love show up to my funeral with a very good future. in their stomach about who I was. My biggest regret is... My biggest regret is already realizing that as much as I keep an eye on it,

I want to spend even more time with the people I love. The one piece of advice that I give to my kids is... Be a good human being. On their terms, not how you want to define it. The craziest thing that's happened in my life is... happened in my life is. Fucking a little bit, brother. You know, I am not detached from how miraculous my life has been and silly things like

judging the Miss America contest when that was something I watched with my mom to important stuff like getting an email weekly from someone who says that a piece of my content took them out of not only a dark place, but sometimes the darkest, scariest moment of their life. It was super humbling. You read your own email? Yeah. The funniest thing that's happened in my career is? The funniest thing that's ever happened in my career?

I mean, probably my first appearance on Conan O'Brien, I could not explain to you how going from operating a liquor store to literally being on the hottest late night show in television in 2007, when that was a whole different game than it is today. It was, and it was funny, if you actually watch the clip, It is actually funny, so I think that's the funniest thing that's happened. The best piece of advice I've ever received is... You know, I know you've seen that because you've done your research.

Fuck, man. I'm really glad my dad tightened me. Again, I wasn't going to go sell, like, junk bonds. But I just know that I couldn't be sitting here at the level that I'm at if I didn't fear, like, if I didn't put my reputation on a pedestal. 10 years from now I'm going to be doing Exactly what I'm doing now Waking up and working on what I want to

20 years? Same Are you ever going to retire? No And I mean this Not only am I never going to retire My great preference at this point God willing Is that I'm always operating

Retirement comes as you know in all shapes and sizes People go to consulting People go to full-time investing And I define it as operating I prefer to be operating something for the rest of my life. If you could pick one trait that's led to your success, that trait would be. It's hard because I love traits. I was about to answer humility, which is not very seen in Gary Bee's content.

You got to really know me. Then I was about to say patience because it has been huge. But I'm going to go with tenacity today. I'm fucking tenacious, and it matters. The one trait that is most important to somebody else's success who you don't know is. So the one trait that I deem is most successful to someone else's, like universally, a trait that is a good indicator to success? Yes.

Tenacity, hard work. If you could be one person in the world, who would it be? If I could be someone? If you could meet one person in the world today, who's alive, who would it be? who's alive. This is important because I've never, because the macho man Randy Savage is dead. If I could meet one,

this is a very interesting indicator of me. I am so insular. I'm very curious. It could really be a lot of people. If I could meet one person in the world that is alive, who would it be? You know who I'd like to talk to right now?

Vince McMahon. Did you see him in Netflix? Forget about it. I'm short of the document. I'm only two episodes in. Let me tell you why, Vince. There's so much there. And I'm sure that surprised a lot of people, and I'm very empathetic that there's plenty of there. But the angle in which I would want to talk to him and what I would want to talk to him about

is strictly around character development. I believe that everything I've accomplished in my career will be dwarfed on my execution of V-Friends. I believe that in 30 years when I sit here and do an interview, with somebody as awesome as you. What they're going to want to talk about is to be friends. Nothing of what we talked about. Sure, they'll touch on it.

I believe that Walt Disney and Vince McMahon and Jim Henson are the prominent figures of modern character development. Jim Henson and Walt Disney did it with fictional characters. Vince did it with real human beings, which I think is very fascinating. The other two are dead. So character development. How to get people...

By the way, you know what my fourth one on that list is? David Stern. David Stern understood that Michael Jordan and Larry Bird and Magic Johnson needed to be superheroes, not human beings. That's what sports is. Steph Curry is a superhero for little short kids, not a basketball player. And that's what I'm going to do with my V friends. And that's why Vince in this moment. If you could go back and give your 21-year-old self one piece of advice, it would be,

don't do a single thing different because at 48 and a half, almost 49, you're a very happy person. The one question you wish I'd asked you but didn't is... You know, it's so funny, I don't think in that term, because when I'm sitting in this seat, I think I'm here to bring value for the audience. Thus, I have no feelings towards questions. You know your audience better than I do.

You're awesome. I want to do a shout out to Mike Herman. Yes. So we wouldn't be here but for him today. Yes. I just met him. He's a new parent at our kid's school. He just moved to LA, as you know. Yes. He'd been here five weeks. He shows up and back to school night.

And randomly we started talking to him as we're walking out. And we started talking. He works at Fanatics. I know someone there. Here we are. Here we are. I really appreciate you. Thank you for having me. Thank you.