The $460M business empire Gary Vee built while you were watching his content

Uh, you know what's funny? I did not own a computer uh for four or five years. It going into co.

I went full phone because I didn't work within Excel or any documentation and it was all email, meetings, social. So, I I think I stopped having a laptop in '15, went to '19 without one, but I've had one since.

It's ironic. I would actually argue it's so crazy to think of evolution. So, I went through those four years. It was the best like not having a laptop at the airport. Like it was the best and now it's completely the opposite, right? Like my OpenClaw computer is like the most important thing in my life, right? It's just so fascinating.

I mean, lots of things. I think with OpenClaw specifically, I'm using it as a capture all for all information. What's been really fascinating even with three admins and chief of staff and all this I'm still like I never got there like some of my friends were their chief of staff is with them in every meeting so there'd be like so much context lost right like in a meeting so much opportunity missed so one of the first things I've done with OpenClaw is it might even happen here I might literally take a photo of this screen sent to my OpenClaw on text it's mainly for CRM for me right now relationship prep and then what's so amazing right? Is once it understands my relationship graph now I'm just building you know logic and agents on top of it to like keep me updated on when things are happening like even sending you guys a email automatically in two years saying congrats on a trillion downloads because it knows I know you knows that was a milestone for you and I do want to you know say what's hey good job you know like like it's just like scaling all my favorite things about humans is definitely step one for me.

So I'll I'll tell everybody who's listening. This is actually a pretty This will be good. This is going to be good for your crew. Nick Dio is the VP of relationships. He literally goes around the world and in essence, he's been with me for 12 years. Started as an intern, grew up in Vayner Media. I trust him to represent me to some degree because I can't be everywhere. And about two, three years ago, I realized my favorite thing about business is people. It's probably why I ended up having an agency with 3,000 people when that's not the best business model. It's why I make so much content. I just like the people part. And Nick just became another version of that which is like I can't be everywhere. And who's got a better job than Nick? go around the world and listen carefully if there's something we could do something for someone for karma, right? Like no KPI, no ROI, like like pay attention. And Nick, you know me so well. You, you know, we have so much to give. Just keep your ear to the ground. You know, figure out who's got the right intent. Figure out who's talking [__] and not talking [__] Like, who's good? Who's good?

Which is the easiest way by the way to spread good karma and good and like you know add value is just hey let me just connect you with 10 other awesome people versus what can I do for you, right? Is that's the easiest way to do it. Yeah, that is a that was one and it was early in Nick's world where I wanted him to get a broader like understanding of different people that were in the you know what's tough about things for busy people that like you know relationships is you just can't scale you're a human right and so like I end up with like these unlimited business acquaintances that I wish I could take to the next step and Nick helps me scale that a little bit by decoding a little bit because I trust his intuition. He's been with me a long time. grew up with me and he represents me well and he's smart and and and I trust him. So then when he hits me and says, "Hey, this person really needs a new marketing person." Like this is how when I'm long gone, I think good stories will come out. Like this is a true example. Hey, this kid's got a good DTC brand. It's gone from 0 to 20 million. We're not an investor in the company. I have no vested interest. They just lost their head of marketing. He was like over dinner talking in a group of 12 like he's stressed and worried and then three weeks earlier one of my best people at Vayner came to me you know uh after eight years and said I don't want to do agency anymore and like literally just putting that person in that company and everyone wins and literally I don't have a dollar in the company literally nothing literally no transaction and like we do that in a way that I I now do feel three like in the last three years people are starting to understand Gary and Gary Vee a little more like cuz we're doing it such scale that eventually the truth becomes your actual reputation.

I have three full-time employees at Vayner X who host influencers that are emerging to walk through the office and meet brand deal teams to maybe get them brand deals on pure karma.

Doing good things for people is literally the highest ROI and lowest risk thing. And most people think it's the highest risk thing because when they're doing something good, they're not doing something good. They're doing something calculated with the expectation or at least minimally the hope that something comes back to them.

That's Sam, to your point, I didn't do this the first 30 years of my career. Like, I got to a place where I could afford investing in that.

It's a really good observation. I think the very simplest clean, you know, this is now me respecting the audience because I think you have a sharp one. It's because I think most things that are taught in business school are shortsighted and are tactical versus how humanity actually works and business actually works. Like if you're and and then I would also say that I am inherently a marathon runner. So I train for marathons in a world where most of my contemporaries on paper are sprinters. Alexis Ohanian was at one of our events and he checked me in the best way possible. We were talking about how yeah we wanted to get this great group together. There's, you know, we don't charge anything. I pay for this whole event out of pocket. I pay like a quarter million dollar a year just to host this event. And it's like, look, I asked nothing in return, which it's all about, you know, just having a really, and everybody's like this. We're all like a generous crew. And he goes, no, no, no, that's not it. And I was like, oh [__] what is he what is he about to say? And he goes he goes, it's just the difference between short-term greedy and long-term greedy. He goes, you know, I'm he was in the first YC batch and he goes, one of the beautiful things about Silicon Valley is you learn the virtue of long-term long-term greedy people. And he goes, it's not a bad thing. It's everybody obviously wants their interest, but when it's long-term greedy, you're going to play a totally different game than short-term greedy.

That's exactly right. And I would tell you my nuance that I do see in some others, which is why I gravitate towards them, is And then if your long-term greed is about rainy day human stuff, not money in your bank, it becomes an extreme nuance of that.

I literally wrote a book because I was so bad at it. I hid it. But it was called 12 and a Half. And in the book, the 13th principle was a half. And it was called Candor. And I spoke about my journey. And I was only ready, Sam, to write about it. You know, you can only talk about your alcoholism when you're like feeling like you're close to fixing it, right? Like, and and by the way, back to like alcoholism or what I was dealing with, which was you're incredibly wrong, Sam. I wasn't a bad firer. I was an all-time atrocious firer. Right? I And I didn't see it. Right? All of us currently the three of us and we're proud of ourselves in certain areas and know we can do but currently by far the biggest problem the three of us have is something we can't see. I used to think of it as my ultimate strength Sam. And it had so many beautiful effects. It led to so much good. But it actually ended up leading to the worst of the worst. meaning, you know, I've been really managing people since I was 18 years old, right? But the liquor store for real. Like truly, like this 18-year-old child is the boss, you know, cuz he's the boss's son in this liquor store. And all the way up to where I am now. And so I used to think my greatest strength was eliminating fear. I had superhero syndrome, right? Like I can take care of everything. I got it. And I had this day in my early 40s, which led me to writing the book, where I realized I thought everybody was rolling with me with lack of fear, but that many in my company were scared because they didn't know where they stood with me cuz I was unable to do candor. And on Friday, I was like, Sammy can have the best weekend, my guy. Like, have like really I think you guys know me. I'm a little go-lucky that way. I'm like, Sammy, you have the best weekend this weekend, right? And you're working for me for three years. Like, all right, Gary. Like, you too. And then like Monday, I'd be like, "Sam, need to talk to you in my office real quick." Hey, so you know, it's going to be your last day. And by the way, I've been sitting on this for a year and a half. Back to your point, Sam. Right. And today's your last Hey. And you're like, "What, bro?" Like I like you've never said any like And then I would blame you. I'd be like, "Sam, you're you're so del like can you?" And then I would talk to Sean be like, "Sean, could you believe Sam? Like everyone in the company knows Sam sucked for the last 18 months. I was giving him a gift for the last year of charity and he's mad at me." I was coming up with that excuse. So my candor was at a zero. I rebranded. So I have this real watershed moment where a group of former Vayner employees like were in a Facebook group like not talking nicely about me. And these were people I really had a lot of continue ironically like you know it's funny that person also over time realizes what they did. So there was like a lot of them I reconciled with in a great way but it was really hurtful but I knew I had to be accountable. I'm like, why are these people who are all lovely people who I really went to bat for, did a lot of great things for, who have really nice careers on the equity of their time with me, why are they [__] on me? And it was all and I knew it cuz I just looked at the eight names and I was like, these were all sloppy exits.

I bleed into both those categories, by the way. And then have a third element, which is I'm the cliche girl that wants to date the bad boy cuz I'm going to fix him, right? So, if I didn't have entrepreneurial DNA, I would 100% be a therapist, guidance counselor, or a coach, right? like and so I allowed both in my investing and in my operating too much in my 20s through mid-40s too much of my nonprofit therapy DNA into my day-to-day I've been able to clean it up in the last 5 years and let me say this to anyone who's struggling with being too nice you know or cuz it was never that I was scared to not be liked it was that I thought I could fix it, that I would squeeze it, that I would make it, but through love, not like trashing you, like what, you know, and and so for anyone who's struggling with this, like there's a better way, like, you know, can't let me say it this way. As long as you're delivering things with candor, all of it becomes dramatically more palpable. I was not. I was holding it all in. That became the vulnerability. And I'm really glad as I've gotten to 50, I'm now in that place where I could be a lot better. And it and it's showed up in the business results. I've been a dramatically better CEO the last three, four years where I've cleaned up my candor. I rebranded it into kind candor. It became the ethos of our company because I think candor a lot of times is used as an excuse to be a dick face and suppress people and so we had to put that word kind in front of it and it's uh it's worked for me and for my leadership and it's been a big step forward in my career.

So I learned from my mother's by far number one by a country mile because almost the far majority of what I do is predicated on the people and emotional intelligence front more than the information. I learn through social media at scale, right? just like just consuming content at scale from random people that are farming carrots in Idaho to someone going deep cut on what they're doing with Claude Code to pontificate and it's truly like I am a product of this era like whose video are you are you turning the sound on uh lately you know when you're scroll on Instagram honestly like I you know I'm pissed right now because I want to my favorite thing is to give flowers and the truth is it's so weird Sam like my brother for example would answer this epic. He's got his ex so dialed in and he would sit here and talk about AI or live shop. Like he would give you like seven names and he'd be like so good and I'm so shitty because the answer is I have seven active businesses that are doing more than eight figures a year in revenue where I am meaning involved.

I'll break them down. Vayner Media, VaynerX, which is 400 million in revenue. I am the day-to-day CEO.

No, it own it owns none of the other six. Next.

Vayner Sports.

Oh, Vayner Sports does sports representation. So, we rep Kirk Cousins, Sauce Gardner, Aidan Hutchinson, Bo Bichette,

NIL at scale. We have probably 300 college athletes.

That's doing tens of millions in revenue. I have VCR Group which is a restaurant group which is if you remember famously I had that NFT restaurant news alert everyone it's crushing it's called Flyfish Club uh we also have Kons and Eto and five restaurants and and I'm actively involved texting with David Roditz all the time so VCR Group tens of millions in revenue as a restaurant group I have VeeFriends is probably the thing I'm most like AJ and David Roditz are 1A in the prior two businesses I am on a in VeeFriends. VeeFriends is going to do minimally 20 million in revenue this year in licensing and selling comic books and coins and trading cards. I'm building a true brand. Like it that by the way that has a darkhorse chance to be really one of my greatest roses because all the ashes of the NFT era that I'm going to get to the other side and be Marvel and Pokemon is going to with everyone so heavy in 15 years. Wine Library. People would be flabbergasted how involved I still am in the wine business. My best friend runs it. I am definitely 1B to my dad and Brandon's 1A, but I work on it every single day. One that's really under the radar, VaynerWatt. I have a very successful TV production company that's kind of brewing right now called VaynerWatt. We have a bunch of shows that have quietly just sold. So you like literally on Hulu and ABC and Netflix, like you're going to see VaynerWatt, VaynerWatt pop up. And then finally, and I'm sure not lost on you guys, the the NIL and brand of Gary Vee. I have a full massive team on it, speaking in books and content and NIL.

I did a deal with Stan Store. I did a deal with MasterClass. I'm starting to let I'm starting to be open to Gary Vee. I don't do like a brand deal. I'll look at seven and eight figure NIL deals where it's really integrated. potentially me doing a little consulting as well. But I think you guys are pro I'm writing a new book called The Individual Empire which talks about the me the Bartletts the Alex Coopers the the the rise of the creator entrepreneur and the entrepreneur creator as the next Fortune 500 companies and my belief with AI blockchain evolving social deeper you know decentralization of Hollywood and and Madison Avenue and Wall Street that the biggest companies in the world are human-based organizations where the human either has a partner that could operate or they're of me where they can be both.

You know, I wake up at 6:00 or 7. There's a workout session every dayish. I'm pretty much an 8 to 8:30 to 8 to 9:00 am start point done between 8 and 10 p.m. depending on the day, but there's not a single break. No lunch, no anything. Every minute's booked. 60% of the meetings are 15 minutes. And again, let's get to the point here, right? Let's get to the point here. This is 30 years of building equity. And my secret weapon was hiring people. And again, you guys, again, this is fun talking to you than let's say a net new podcast where I've interacted a little bit with you guys. I had this feeling that I was going to be able to have a lot of really good A and B players around me that would stay with me, that could do bigger things, could do things on their own, but that the relationship and that they would believe in me and that they would say, you know, in 15 years, I might actually make more money being Gary's number 13 versus me my own number. I just had this intuition and that I could convert D's into B's and C's into B's. I just had this feeling that my superpower was the human relationship side. And so the reason I can do this, so yes, I work a lot and yes, I'm I'm uncomfortably efficient with my time. And yes, I'm on a boat which has seven holes and I put my finger in the one that needs it most for every parent that knows you're only as happy as your most unhappy child. And so my ebbs and flows of like, oh [__] Vayner Sports needs me, or oh [__] Vayner, like there's all that, but the real reason is because of the 50 people from Ryan Harwood or Kalin or Claude or JT or AJ and Greg Gensky or David Roditz and Connor Hland or Andy Kay and John and JT John Troutman and May and Rips on VeeFriends or Brandon Warick on Wine Library or Eric Watenberg VaynerWatt on that. And I've got another one coming that I'll announce next year, standalone business. Uh, and it's somebody who's worked for me for 11 years who's going to be my co-founder. And I had the experience with Resy. You know, like people forget that I'm the co-founder and inventor of Resy, but I had Ben Leventhal be the 1A, I was the 1B, and that was a hefty nine figure exit. And I had Empathy Wines, two former interns of mine who worked for me for 11 years, and we started Empathy Wines, and in 18 months sold it for a almost nine figure hefty eight figure deal to Constellation Brands in 18 months. Just like, you know, everyone's like Gruins. I'm like, I did that. Not not to 1.2 billion, but it's because when I do things on a net new business, the person is my family member. It's family business. We know everything about each other. It's 7 to 10 years.

Before we decided to do X, Y, and Z, they roll differently than a lot of people trying it with net new people they hire randomly.

Not only is that true, Sam, I think I'm the preview. This is what's going to happen. This is what is happening. Like, if you look at the derivatives of all the people that are like kind of that crew right now, what do you think is happening? And then of course there's Kylie Jenner and Hailey Bieber where they need a business person to also be in round. But then there's also like, I mean you guys are like in PO it, you know, everyone has different hopes and dreams and Sam, you've nailed it. Like to me, like I love this [__] bro. You know, people go and buy a home in the Bahamas and that's and play golf and that in Bakers Bay and that's their escapism when they need an escape. When I need a break from VaynerX, which I do a lot cuz client services suck [__], I don't go to Aspen. I go to two days offsites for VeeFriends cuz it fills my soul and I do the comic stories of my characters, you know? Or I go to a half day at Wine Library and talk to Brandon because he's my best friend since I was 14 and I need it for my soul, but then we also fix the business.

I'm mad at you, bro. You took my [__]. I was... You asked. I was about to say the thing that everyone else is spending an hour on.

You got slam poetry snaps for me.

And I just went there. I knew it subconsciously. Then it became just, you know, then years went on and it became conscious and then I executed. I have this huge pride of how underrated as a businessman I am because what I just dropped on you guys literally nobody really knows which is wild because I'm Gary Vee and I'm talking to all the time and I think I got there on the 15-minute meeting and the family business vibes of my partners in crimes and the top and by the way it's not just one person like every company requires three or four family members for it to really work the way it works for me cuz you got to have a backup and a backup and a backup cuz there's so many variables that can go into these things. So, the 15-minute meeting has been gangster for me, gamechanging for me. I do think I'm getting three days of work in one day. This is all happening at a time where I'm spending more, I mean more time with my family than ever. You know, I have teenage kids. I have a wife. It's just like you can be so much more efficient if you have remarkable people around you and you're obsessed with not wasting time to fill the slot.

I would say 30% I'm being informed, 70% I'm making decisions.

It's funny you said that. I've got a bunch of new film people because all my people look, this feels incredible, go on to these incredible things after they film me for a little while and get all these offers or start doing things. And so I constantly have a D-Rock coming through, you know, every year or two. The number one thing, Sam, every single new admin and every single new person that films me says is they do not understand the switching. I think I clearly DNA, I wonder if growing up in retail where you're just switching like everything's just always on. I don't know.

I think one, it's... I've come to learn it's unique to do that. Two, now you're really talking about it. That has definitely been... even that has definitely been something that I got from my mother, which is being able to carry in the moment adversity and negativity and still show up. Like I think a lot about that as a leader. Like I get a lot of bad news every day. One, I'm psycho and I'm in the HR of all my companies and now we have so many goddamn employees. Every day someone's dad is sick. It's just like I want to know if somebody in my company is going through tough stuff. And then there's just when you're in client services. We went 16 months without losing a client at VaynerX. We're ripping hot, right? And then recently in the last 60 days, we've lost two. And the first one was not surprising. Second one was a little bit. And I was walking right into another thing and I was just like, it's funny you say that. I was like, man, I really got into that because I was pissed and like I wanted to fix it, but I knew I had to show up for this thing and this thing and this thing. And then not to mention all the things that happen in my personal life similar to the college thing. There's always something just like being able to like eat [__] and firefight is like a really strong emotional framework that is hard.