What It Really Takes to Build and Lead a Company in 2026 l The CEO Series with William Salvi

0:00Podcast nation, before I get you into today's podcast, big announcement. as you probably heard at this point because I had John from Stan on the show I'm an investor advisor to an incredible startup called Stan Stan.store I'm sending you right now to GaryVee.com GaryVee.com slash Stan go check this out we've done a GaryVee Stan Store challenge which actually has a weekly call with me this is built for everyone who's been affected honestly by my overall content the tech stack all these features and the minimal costs per month that Stand Store has built is really the tool that was needed for this world that I envisioned when I wrote Crush It, when I wrote Crushing It and this overall thing I'm thinking a lot about lately which is the individual empire, right?

0:48This creator entrepreneur slash entrepreneur creator economy that I think is gonna eat up the oxygen very honestly, the thing that so many of you want in your life and the reason so many of you are not there yet is you've got the strategy for me, you've got the ambition within yourself but you don't have the tools for you to fully maximize it and I believe you can find that at Stan store Stan dot store but specifically I want you to sign up for it through my challenge because I want to get access with you and plus there's a bunch of cool things so if you want to go see those cool things go to GaryVee.com slash Stan S-T-A-N now to the podcast this is the Gary Vee audio experience the levels of giving a shit of what anyone thinks of me.

1:33It doesn't really penetrate very high. I'm really not playing for anyone else. Enjoy eating shit. I know something about business. Business is not education. Business is not the political system. Business is not parenting. Business is, if you over coddle and you over entitle, you go out of business and everyone gets fired. Do you think there will be almost like an adverse effect of all this generative AI stuff? No, no. Because I think it's like actually fundamental. What matters to you the most? Who I am when nobody sees me. Who are you when no one sees you? A really nice boy. In real life, I will lay my body on the street for an old lady in the middle of the street to cross.

2:14In competition, I would punch that lady in the face. There's a lot of entrepreneur bros. They're preaching business practices, and then they sell you some bullshit corps. I think they are a negative for the business community. Selling something you do not believe in is always bullshit. Everybody plays it different. This is how I play it. I have always and to this moment Respect when people do not like what I do in hindsight may be a good thing It's always a good thing when you're fucking talented When you are a true entrepreneur and it's your baby, it's fucking real The only thing I believe more than the sun will come up tomorrow is that winners fucking win All right, we're in New York City.

2:53It is one of my favorite cities in the entire world It's second to Chicago because that's my favorite city in the world, but we're at Hudson Yards. It's this beautiful area with whatever the hell that building is, but it's great. I love looking at it. We're going to be talking to Gary Vaynerchuk, the chairman of VaynerX and the CEO of VaynerMedia. He is a business personality. He's one of the OGs of YouTube. Quite literally, he started a wine show on YouTube in 2006, and now he's become a business titan. We're going to be talking to him, all things media, all about the dynamics of his business.

3:27And of course, his collectibles, sports, and he's got a lot of predictions on everything in business and in life. My name is William Salvey, and this is the CEO Series, where we have real conversations with real CEOs. And don't forget to subscribe to our YouTube channel, Executive House. It is the best content on executives. We get people like Gary Vee, CEOs of Fortune 500 companies, CEOs of startups, all different types of executives, subscribe. Let's go talk to Gary. Get 30 interns, start interacting with your community, and you make much more ROI. You want to do something cool? Let's zoom in over here.

4:02We have 125 people watching me on newsfeed. How many of you read the newspaper every day? Go. No, no, no, no, no. Hell no, no, no, no. Yes, yes, no, no. When they start embracing social media marketing, it's really going to explode. All right. We're with the CEO of VaynerMedia and the chairman of VaynerX, Gary Vaynerchuk. Gary, thanks for joining us. Thanks for having me. Awesome. Well, I'm actually interested because unlike most CEOs that we've interviewed, it's like hard to find out what exactly you do and how many entities you own and operate with. So I'm interested, like, tell me a little bit about all the companies that you work on and basically your day to day.

4:39Yeah. So VaynerX, which is the holding company where VaynerMedia and five or six other marketing service production companies sit under is no question my primary. You know, it's a 2 ,000 person global company. We're in HQ here in New York, but, you know, hundreds of people in LA and in London, Amsterdam, Singapore, Tokyo, Mexico City. So it's a very large marketing organization. You know, probably the pioneer in social media marketing for Fortune 500 companies on the back of what I did for my dad's liquor store and my personal brand. We started this in 2009 with my brother. The other main, main, main thing I work on is VFriends.

5:20My Pokemon, Marvel, Disney-like intellectual property started as digital collectibles and NFTs, trading cards, comic books, Squishmallows. Are you into that stuff or are you into the tech? I'm into both. Yeah, because I just played Pokemon first gen again. Yes. I was like a child on my phone. Yeah, it was great. I mean, do you know Pokemon's worth$100 billion? Yes, isn't it the most valuable IP right now? It's like, that is a profound number. Yeah. Like worth more than multiple, multiple, multiple sports teams. So very fascinated by intellectual property businesses, accelerated by the AI world.

5:57I think IP and copyright are one of the few places you can feel comfortable in this incredible disruption. The other places where I put energy are VaynerSports. So VaynerSports is a very large sports agency that my brother AJ is the co-CEO of. I'm the chairman, I'm pretty active in that. You know, recruiting players, signing athletes. Vayner Sports is within striking distance now of becoming one of the major players in sports representation and marketing. The two other businesses that I have my thumbprint on pretty significantly is the VCR Group, which is a restaurant hospitality business. Fly Fish Club, which is our big win down in downtown, but seven or eight other restaurants, mainly in Vegas and New York.

6:45VaynerWatt, which is with Eric Wattenberg, and Nima Vand is a key player in that company, that's a TV production company, where that will start hitting a lot of people's radars because we've sold a bunch of shows, and as those shows start to show up on Netflix and Hulu and other places, and that VaynerWatt logo comes in the beginning, I know I'll get some tweets and emails like, what's this? And then, let's call a spade a spade, you know this, most of the world thinks I'm an influencer. I'm Gary Vee, and I day trade attention. I think I'm a positive entrepreneur. Some may think of me as a creator.

7:20Many people just only know me as Gary Vee. But Gary Vaynerchuk is the active chairman and CEO of VaynerX and of VeeFriends. But I think the greatest title that I hold is nice guy. That's how I... And a motivational speaker. Yeah. So do you ever get sick of that if someone sees you on the street or they start talking to you? I'm flattered. Like I'm humbled by people getting value out of the words I speak. How often are you filming content? I'm just getting back into it actually. From 2015 to 2019, I filmed every minute for four years of my life. Then COVID came and I never really got back on the saddle because I've been really right here.

8:01I've been less Gary Vee for the last four years than I've - Do you miss it? enough that I think October 1st, I'm coming back. Yeah. We all know you, or a lot of people know you as the personality, the personal brand is very strong, but on the side of it, you have this very strong brand of VaynerMedia and VaynerX. How did you actually build and scale the business while also leveraging the personal brand? By doing both well, to your point. It wasn't like my personal brand. In fact, my personal brand was a detriment early on for Vayner. How so? Well, the corporate world in 2013, 14, 15 was - They weren't used to something like this.

8:43They weren't used to something like this, especially someone cursed. I mean, do you know how many companies, literally Fortune 500 companies, that were ready to hire VaynerMedia and then a board member or CEO - Saw some shit that you had. Saw some shit that I said with three curses in two seconds and they're like, fuck that. Do you still get it or now they've transcended it? I think culture has changed. Yeah. Right, like the things that I kind of was ahead on, cursing, dressing down, they've become the norm. Do CEOs need to be more, just more themselves? I think so. Like back to your audience and what this is about.

9:19I think so, but I'm empathetic. Oh, by the way, you think you hate CEOs? Good news, they have bosses. It's called the board. You know, I'm empathetic. Like I sit on boards, I know boards, I am getting courted for boards, and board people that are on the boards of the biggest companies in the world are often in their 60s, 70s, and 80s. And I, by the way, I have always, and to this moment, respect when people do not like what I do. The reason CEOs are not themselves is they're scared to get fired. Which makes them, maybe they're not as effective as they need to be, because if they were super effective, then they'd be more willing to.

10:00And if they were super duper effective, maybe they would have their own business and have no ability for someone to fire them. The only reason I'm fully the way I am is because no one has say. It's a blessing. Like I have complete freedom. Like I will never, ever, ever run a business where people have say. I'd rather not have a business. Just put in work and enjoy that. Enjoy eating shit and dirt and bleeding and the grind and don't give a fuck about what anybody else thinks. Have four jobs. Fucking Wendy's, Walmart, your side hustle worked. Okay, so in less than eight years, when I'm a millionaire by 25, I'll come shake your hand.

10:38I promise you that statement itself made me 100 % guarantee that you won't.

10:51So we've talked to a lot of CEOs And I would say a lot of them seem to, a fair amount of the larger company CEOs seem to have more of a mask on. And I think CEOs need to be a little bit more authentic. I think you're very forward with that. Do you think there's a little too much out of business leadership where they're just trying to chase profits versus preaching like passion and go after what you're good at? Yeah, I mean, I think there's a couple of things there. The reason I'm smiling is actually not passion versus cash. It's that most CEOs of big companies are not entrepreneurs. Most of the people you've interviewed are executives.

11:26The boredom in which runs through my body when I jam with some of the biggest CEOs in the world is extraordinary, not because they're bad or not smart. Some of them have 50 times more skills than me in 50 important areas, but they are not inherently creative, risk tolerant, playing outside the lines, seeing in color. I have a question about being a CEO generally. Please. And CEOs also generally. Yes. I think they are viewed negatively. One of the reasons, big company CEOs. One of the reasons why we do this show is because there are a lot of CEOs out there that do things with integrity. They have good cultures.

12:07They run good companies. They're performers as well. Yes. It's the headlines of the 17 CEOs who get such massive salaries, who are dick faces, get all of youth culture to believe there's something wrong in that and they're horrible tyrants. I think that that is just as lazy as saying all Mexican people do this or all women do that or all Italians do this. So mainstream media, which then leads to social media, has overly focused on the 0.01 % of CEOs and 99 % of CEOs are running midsize and small size companies. And even the large CEOs, there's a lot of people who are incredibly noble and wonderful.

12:51I want to run this place wildly positive and good and I feel great about the culture we have. But at the same token, if I let it get too far to any side, it breaks. And if it breaks, we go out of business. Yeah, and then more people suffer. Yeah, and listen, you're talking to someone who disproportionately his kryptonite and disproportionately the F on his report card as a CEO, entrepreneur, and business owner has been his inability to fire people. For a lot of you, this is gonna be a really tough next three, four, five months because it's gonna be the first time that you're ever going to have to fire someone, lay them off, be heavily compassionate, understand the score.

13:32The reality is that if there's layoffs, they're starting. It's gonna be harder to get another job. People are going to be struggling out there. And the most you can do is be gracious and as kind as you can be. So laying off 800 people, that is not like people don't do that for ha ha ha for fun. Every single CEO in the world is sitting around right now and saying, if I don't tighten up and get AI put in place, a company I'm competing with will do that. They will beat me and I'm going to lay off 8 ,000 people, not 800 people. To get philosophical here, have we gone a little off with the business world and business leadership where it's growth at all costs and profit and that's all you must do?

14:17Do you think that's... I think we're in the... No, I actually think we're in the nicest place we've ever been. Do you know what 1984 looked like? I think culture has become so ridiculously entitled and soft and we cry about ludicrous things. at the same token to your point, I do not believe fear is the useful weapon of choice to get things done. So I think both can be true. Yeah, because you're pretty positive in your messages. I'm incredibly positive, but I also deeply believe that entitlement has become a disease. What's the way out? The way out is consequences. See, the reason I don't worry about it is I know one thing about business.

15:00Business is not education system business is not the political system business is not parenting business is not all these other things businesses if you over coddle and you over entitle you go out of business and everyone gets fired i now run in circles where it's a players hanging out with a players right these fucking a players are just a bunch of fucking sixth grade girls i'm stunned by how how many titans that everyone here looks up to that seemingly look like gangsters on podcasts and the internet, how many of them are ravaged with envy and jealousy of some other guy or gal that's making a couple more bucks.

15:39And at these dinners where people get into fucking talking shit about other winners, I am the most consistent voice. I let it go for a little while, and then somewhere in about 20 to 30 minutes in, I will always find my opening. I'm like, yo, just real quick, Like you talking shit is not going to stop that person. And in fact, all you're really doing is you're looking like an inferior player. The only thing I believe more than the sun will come up tomorrow is that winners fucking win. Number one, it's hard to research a person like Gary just because of how much content he has on himself on the internet.

16:17It's like, what do you choose? He also says quite a lot. So I don't know what to specifically research or talk about because he talks about a lot of things. He has, I wouldn't call them hot takes, but he's got takes on a lot of different things. And he's a trendsetter, I would say, versus a trend follower. Hence his YouTube show in 2006. Hence his getting into personal branding and utilizing his personal brand for his business. But I don't think people quite realize how big his companies are. I mean, they're doing they have 2000 employees globally, multiple office locations in Tokyo and Chicago and London.

16:54They're doing hundreds of millions of dollars in revenue. And then on top of that, that's just VaynerMedia. He's got a lot of different companies that he does. And it's really astonishing to see his energy level and how he utilizes his personal brand, how these companies, some are in the thick of it and thriving. Others are getting started and he makes so much content. I mean, Gary Vee is a dynamic business person. We have a couple of fun segments. One of them is the most Googled questions. I chose... I love it.

17:34How did Gary Vee become rich? I guess ultimately two things. he even though he made$65 ,000 a year through his 20s on average he lived a $28 ,000 a year life which meant he had after about 9-10 years somewhere in the ballpark of 80 to 150 thousand dollars in savings and when he saw the moment to invest in Twitter and Facebook he did what is Gary Vee do I think that's a fun question because I do think that I'm a renaissance man I I think I'm a preview not the anomaly I think there will be many more businessmen and women like me because they're gonna realize go for your joy not for your money how did Gary Vee build the wine library from three to 60 million underpriced attention the in detail launching a website as one of the first five websites for a liquor store in the country first five stores to do email marketing first store to buy Google AdWords on the word wine and all the big terms and then finally the first person to start a wine video show is Gary Vee going to buy the Jets will Gary Vee buy the New York Jets no one knows Gary Vee will try very hard for the rest of his life to pull it off and Gary Vee will be unbelievably content with the effort against it because the joy of chasing it has been and will continue to be a lot of fun.

19:02You'd be a good owner. I would be a great owner. You'd be a good owner. I'd be a great owner because I think being a great owner is picking good people and empowering the fuck out of them.

19:18Tell me about what's behind you. Give me some of this. This is a lot of wine, you got jerseys. Yes, this is probably in a lot of ways a good reflection of like how I see the world and what I'm interested in. A lot of VFriends stuff right now. This is really fun. You know what's really cool about this? This is how I think about VFriends. I think it's cool that you two, in 16 years, over dinner, will be like, man, we were fucking there. We really didn't take note of VFriends. We didn't appreciate what Gary was, and he said that he was doing it. There's this almost subconscious disbelief that I'm getting from the world of like what I'm telling them I'm actually gonna do.

20:05They think it's all just a game. A bunch of toys, lifeless trinkets. Ha! Little do they know, it's so much more than that. Sorry, quickly describe it if you could. VFriends is an intellectual property business. It is literally no different than Pokemon, Marvel. And you're eventually going to start doing live trading, shopping, everything. Literally everything you can imagine. I mean, I'm doing it already. But think even bigger. There will be a VFriends amusement park in your lifetime. There will be a VFriends on ice touring circus or ice capades. There will be feature films like VFriends in movie theaters.

20:56It is an incredibly prolific part of my career. These vending machines, there's hundreds and hundreds and hundreds of these vending machines around the country in stores. I cannot wait for your 11 month old when she's five to be wearing VFriends pajamas, reading VFriends books. We have an incredible kids book that's crushing, a YouTube kids channel that's crushing. I am desperately trying to build the next Pokemon Marvel Disney. IP. IP. Yeah.

21:43What's been the highest growth sector of your business, subsidiary of your business? VaynerMedia. VaynerMedia. VaynerMedia is ripping hot. Are your main competitors Edelman, Leo Burnett, like those types of companies or is it different? But those companies are so grounded in yesterday with all due respect that social first is eating up. Traditional PR, Edelman, social first is eating up. I mean, who wants to spend that kind of money on a television commercial? What are your thoughts on like traditional communications with specifically with like C-Suite? Because we have strong opinions about this.

22:20I think it's shit. We think it's shit too. We think that we're going to be the winner of it. We think that, we think if you win on social and on crisis, like actual crisis, because they were going to care about that. So there's a little bit of a traditional, but pitching editors and hoping the Wall Street Journal, getting on CNBC, like that's like, no. Do you want to scale your company to a point where it just keeps growing in size? Or do you have a point where you're like, I don't need it to get that big. I think that would take away from what I'm doing day to day. No, we're long past that. Yeah, okay.

22:54Like we're now in growth in perpetuity. I'd like to build a private equity firm on top of the agency. So my belief is that everything is going to be commoditized in the world except the ability to communicate. That's how much I believe in communication and attention. I am building a communications infrastructure that can actually bring attention and successful marketing to any politician, any B2B business, any B2C business, any aspect of anything in the world. I want to be the emperor and I want to be in control of the Death Star and whatever I point it to, I can take this ecosystem and point it towards that and then thus rendering that dramatically more successful, dramatically more known, dramatically more capable of getting attention and conversion and sales.

23:54And so that is kind of the real secret master plan of Vayner is to build that infrastructure and that capability. Because I believe that that is the ultimate leverage in the world we now live in. We like to preach authenticity. And when you're a business leader, it's really important to be yourself. And it will do wonders for you as a business leader. I believe that. he walks the walk and talks the talk. And he's clearly like he's, you could argue that he's too authentic because he is just exactly who he is. It was great talking with him on camera and off camera. It's exactly who he is that you see on the videos that you've watched of Gary V.

24:39But I can't stress this enough. He's not just a personality. He's got a lot of great businesses and trend setting businesses that I think he's not only onto something because the proof is in the pudding, but he's done a lot of great things within his own company. And it seems like he's got all the energy in the world to keep going. When my life was 85 human beings in New Jersey that were the big wigs of the liquor and wine business in New Jersey. And I was telling them in 1995, 1996, that I'm going to launch a website, this internet thing on the worldwide web. and I'm gonna build one of the biggest wine stores in the country, I could see on their faces, like, okay, kid.

25:26Cool, yeah. Like, in fact, when I launched winelibrary.com and it cost like$10 ,000 to make the site, which was like a billion dollars for us as a small business at the time, a lot of my dad's contemporaries who cared about my dad because they watched him go - They were like protective of this decision. Correct. They were like, hey, man, correct. Yeah. They're like, open a second store. That's how you build it, right? When I started Wine Library, my best friend Brandon and my father, after the first episode, are like, what are you doing? Like, because I had never not worked on the business, so now I'm taking an hour to make the video, and then I was spending all my hours at night replying to all the comments.

26:06Something I really understood, in hindsight, was that attention was the most important asset. I kind of understood money my whole life. I was like, money's fake, meaning America could keep printing it. The asset in the world, how do you make it bigger? You get more attention. How do you get more attention? You dominate social media. The end. Social media is currently not being utilized enough in your eyes by many, many people. By almost every human, including me on earth, and I produce 40 pieces of content a day. What's something that instead of saying like, oh, social media is untapped or AI is gonna explode, what's a prediction you have for the market and media?

26:46I love experiential. like events, physical. Like the rise of digital creates the opportunity. Like I think all of us are yearning for more real life stuff. So I'm very, very bullish on experiential. Do you think there will be almost like an adverse effect of all this generative AI stuff where people are like, you know what? I'm actually interested in that. No, no, because I think it's like actually fundamental, but I do think there's an opening for real life to be like a good side dish. I think the AI, the digital, that is now the main course. Yeah, it's here. It's here. But the amuse-bouche, the appetizers, the side dish, the dessert, there's cool stuff there.