My First Million - How Gary Vee runs 7 businesses

Episode Date: May 19, 2026

Get Sam & Shaan's CEO lessons in one guide: https://clickhubspot.com/ptcw Episode 826: Sam Parr ( https://x.com/theSamParr ) and Shaan Puri ( https://x.com/ShaanVP ) chop it up with Gary Vee.  �� Show Notes:  (0:00) Intro (2:40) Nick Dio, VP of friendships (6:47) How to invest $1M on yourself (10:06) being long term greedy (17:53) Gary breaks down his companies and revenue (21:43) day in the life of Gary v (26:19) breaking down the 15-minute meeting (29:07) eat shit and firefight (31:00) picking projects (32:31) 5-year bets gary is making (34:04) missed fat pitches (38:00) vetting shady people (42:55) Mimetic rivals — Links: • https://vaynersports.com/  • https://www.vaynerwatt.com/ • https://winelibrary.com/  • https://empathywines.com/  • https://resy.com/  • https://vcrgroup.com/ • https://vaynerx.com/ — Check Out Sam's Stuff: • Hampton (joinhampton.com): My community for founders. Average member does $25m/year. Many of the guests are members. Get after it...apply: http://joinhampton.com/mfm — Check Out Shaan's Stuff: • Shaan's weekly email - https://www.shaanpuri.com  • Visit https://www.somewhere.com/mfm to hire worldwide talent like Shaan and get $500 off for being an MFM listener. Hire developers, assistants, marketing pros, sales teams and more for 80% less than US equivalents. • Mercury - Need a bank for your company? Go check out Mercury (mercury.com). Shaan uses it for all of his companies! Mercury is a financial technology company, not an FDIC-insured bank. Banking services provided by Choice Financial Group, Column, N.A., and Evolve Bank & Trust, Members FDIC • I run all my newsletters on Beehiiv and you should too + we're giving away $10k to our favorite newsletter, check it out: beehiiv.com/mfm-challenge My First Million is a HubSpot Original Podcast // Brought to you by HubSpot Media // Production by Arie Desormeaux // Editing by Ezra Bakker Trupiano /

Well, this is going to be one of the highlights that I know from this meeting, this podcast. I love that I said meeting. This feels more like a business meeting. That's why you guys are successful. I feel like I can rule the world. I know I could be what I want to. Gary, let me ask you a hard-hitting question. I've known you now for a few years, a while now.

Do you own a computer? You know what's funny? I did not own a computer for four or five years going into COVID. So what year did you buy your first laptop? I went full phone because I didn't work within Excel or any documentation, and it was all email meetings, social. So I think I stopped having a laptop in 15, went to 19 without one, but I've had one since.

You know those luxury brands where it's like quiet wealth or whatever where there's no label? We found the podcast version of this, which is that the richest guys who come on the pod, They don't know how to use a computer. They're like, assistant sets up a screen. They just show up. We had one guy try to share his screen, and he was like, honestly, he's like, honestly, guys, this is, this is bad. I don't know what, I don't even know what I'm doing.

We go, just clicking Chrome. He goes, what's Chrome? He didn't even know what Google Chrome was. I don't think I have one of those. It's ironic. I would actually, you know, 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? My OpenClaw computer is like the most important thing in my life, right? It's just so fascinating. Wait, what are you doing with OpenClaw, Gary? 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 where 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 crap. 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 an 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, it's just like scaling all my favorite things about humans is definitely step one for me. You just said something about relationships. And you have this guy, Nick Dio. Yeah.

I think you had, I don't know if he's still with you, but this fascinated me. He does these really interesting things. He's like, post these dinners almost like on behalf of Gary. Who is this guy? What is he doing? So 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 BP of relationships.

He literally goes around the world. And in essence, he's been with me for 12 years, start as an intern, grew up in VaynerMedia. 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 KBI, no ROI. Like pay attention.

And Nick, you know me so well. you know, we have so much to give. Just keep her ear to the ground. You know, figure out who's got the right intent. Figure out who's talking shit and not talking shit. Like, who's good? Who's good? Well, let me tell you what it was like from my perspective.

I got a DM from you. And I don't think I, you could have said it. And there's a chance I didn't read it closely. But it said like, hey, I'm going to be in Austin. Do you want to get dinner? Yes. Yeah. I just said yes.

And then I just got sent an invite. And the invite, like I said, it could have said the details. But I show up. And it's like 50 people. It was at a very wealthy person. home, this Microsoft executive's home. And I'm like, hey, where's Gary? They're like, oh,

he's not here, but I'm here. I'm Nick, and I'm hosting it on his behalf. And I meant like... Yours was felt like more of a robad dope? Yeah. No, but I want to give you credit. I don't think I read it. There's a chance I didn't read it, but I get there and I met like... I remember that party, because I was one of the bigger ones.

It was never alluded. Like, I apologize if we didn't word it well, but I remember the context. Like, we weren't trying to trick you to meet Nick. No, I don't think so. And I bet like, I bet this cool dude named Hunter. Do you know Hunter? I think his name's Woodall. He's got one leg and he won in the Paralympics.

He was badass. I met like all these like, it was like this athlete, this Microsoft executive, this person, this person. I met all these cool guys. It was awesome. Which is the easiest way, by the way to spread good karma 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? That's the easiest way to do it. Yeah, that is a, that it was one.

And it was early in Nick's world where I, 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 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 zero 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, 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 transact. And like we do that in a way that I now do feel three, like in the last three years, people are starting to understand Gary and Gary be a little more. Like, because we're doing it at such scale that eventually the truth becomes your actual reputation. I think to add on the surface. Chris, it's like, okay, great.

So this guy hosts dinners, that's cool. Sounds like he's got a mandate to spread good karma and just help people. That's cool. I think this is actually unbelievable. I can't believe you don't talk about this more. This is like, you know when that story came out a few years ago where it said LeBron James spends a million dollars a year on his body? And people went nuts.

And this went everywhere. This is like a global thing. Other athletes turned on to this. And I was thinking about it the other way. I was like, first of all, obviously. This guy is a billion dollar athlete. For him to spend a million dollars a year on his body, that's like, A masseuse, a trainer, a chef, and there's nothing.

He should be spending three, four times that, if anything. Second is, what a great question everybody should ask themselves, who wants to be great? Is what is your equivalent of spending a million dollars a year on your body? And my executive coach, for example, he spent a million dollars getting coaching himself from the best in different disciplines. He would overpay and say, how do I get, how do I go do an immersion with you? I know you usually do once a week, but I want to do immersion because he's like, I want to be the best coach. So I'm going to go learn all the modalities from the best teachers of those modalities. And I just think everybody should ask us.

And what you're doing with Nick, to me is the equivalent of LeBron James spends a million dollars year on his body is Gary spends, Gary spent probably at this point, five million plus, 10 million maybe developing relationships with people who he thinks are doing good things in the world. He wants win in their sales. I have three full-time employees at VaynerX who host influencers that are emerging to walk through the office and meet brand-heel teams to maybe get them brand deals on pure karma. Yeah.

See, that's amazing. And I think that type of investment, it only comes from first principles. 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 minimumly, the hope that something comes back to them. Well, but on the other side of that, it could be like, well, I need to, I'm spending money on

these things. I have bills to pay. 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. Yeah, but what I was going to ask you is, I think that you've always, you, from what I could tell, you've always defaulted to hiring a lot of people. I think that, like, it seems like that's how you like to operate. And also, you've defaulted to doing things that.

don't really make sense on paper, but because you're you, it does appear as though it works out nicely in terms of profit. How do you like justify doing some of these things that don't make any sense financially, knowing that like when VaynerMedia was five or 10 years old and your margins were a bit tighter and you didn't have enough money to go around to do some of these wacky things? And yet it still appears as though you did do them. It's a really good observation. I think the very simplest clean, you know, this is now me respecting the audience because I think I think you have a sharp one. It's because I think most things that are taught in business school are short-sighted and are

tactical versus how humanity actually works and business actually works. 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 O'Hanning 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. We don't charge anything. I pay for this whole event out of pocket. I pay like a quarter million dollars year just to host this event.

And it's like, look, I ask 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 true. And he goes, no, no, no, that's not it. And I was like, oh, shit, what is he about to say? And he goes, it's just the difference between short-term greedy and long-term greedy. He goes, you know, 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. 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 greed is about rainy day human stuff, not money in your bank, it becomes an extreme nuance of that.

What's rainy day human stuff? What does that mean? I probably do everything I'm doing, not to get into a deal in that. nine years, I put a million and make 40 million. More for my daughter has an issue in 19 years in her personal life. And for some reason, Sam's nephew can help her. I'm good enough to take care of my money part. Sometimes it's hard to run a business that way, being nice all the time, because you

have to make difficult decisions, like firing someone if they suck. But you seem like you are a really bad fire. 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 can only talk about your alcoholism when you're, like, feeling like close to fixing it, right? 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 fireer. I was an all-time atrocious fireer. Right?

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 has 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, because 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 of my company were scared because they didn't know where they stood with me because I was unable to do candor. And on Friday, I was like, Sammy, I got the best weekend, And my guy, like, really, I think you guys know me.

I'm a little go lucky that way. I'm like, Sam, he had the best fucking weekend this weekend, right? And you're working for three years. You're like, Gary, like, you too. And then like Monday, I'd be like, Sam, you talk to you in my office. Hey, so, you know, it's been 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 day. And you're like, well, bro. Like, I, like, you've never said anything. Like, and then I would blame you. I'd be like, Sam, you're so delude. Like, could you, then I would talk to Sean? to 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 re-branded. 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've 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 Batford and a lot of great things for, who have really nice careers on the equity of their time with me? Why are they shitting on me? And it was all, and I knew it because I just looked at the eight names. And I was like, these were all sloppy exits. You know what's funny is, have you guys sort of obviously you have? But Jensen Hung, the NVIDIA guy, he has this great line where he's like, I'm not going to fire you.

I'm going to squeeze you so hard that greatness comes out of you. And then interestingly, Dave Portnoy, the founder of Barstool, he had another point where he goes, I never fire anyone. I refuse to fire anyone, but we are going to make you great. Like he says something like that. And I thought that was so fascinating because that's the exact opposite of what I think.

You know, we had Neil Patel on. And Neil was like, I only hire people who have been there, done that. I only hire people who have built this thing already that I want built. And if they can't do it, then I fire them within a week, which is probably honestly the more common attribute of like just hiring people who,

have been there done that. And then if they suck right away, you know, you hear a higher slow, fire fast. 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 because 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 to, 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 five years,

and let me say this to anyone who's struggling with being too nice, you know, or... Because 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. You're like, what, you know? And so for anyone who's struggling... struggling with this, like, there's a better way.

Like, you know, can't, let me say 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 a 50, I'm now in that place where I could be a lot better in 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 worked for me and for my leadership. And it's been a big

step forward in my career. You give a lot of coaching and advice to entrepreneurs around the world. Who do you learn from? So I learn from my mother's by far number one, by a country mile, because almost the far majority of what I do is predicate on the people and emotional intelligence front more than the information. I learned 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. Whose video are you turning the sound on lately when you're

scrolling 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 f***-ex so dialed in. And he would sit here and talk about AI or live shop. Like, he would give you like seven names that 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 meaningfully involved. Which ones are those? Tell us about it. What are we got? Break up down.

Vayner Media, Vayner X, which is 400 million in revenue. I am the day-to-day CEO. And that owns all the other six? No, it owns none of the other six. Next. Vayner Sports. What's VaynerSports doing exactly? Oh, VaynerSports does sports representation.

So we rep Kirk Cousin, Sauce Gardner, Aidan Hutchinson, Bo Bouchet. And NIL stuff too now or just pros? NIL at scale. We have probably 300 college assets. athletes. Okay, so that's doing tens of millions. That's doing tens of millions in revenue. I have ZR 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. We also have K-pons at ETO and five restaurants, and I'm actively involved texting with David Roddell.

It's all the time. So VCR group, tens of millions in revenue as a restaurant group. I have V-Friends. V-Friends is probably the thing I'm most, like, AJ and David. David Rodolitz are one A in the prior two businesses. I am one A in VFriends. VFriends 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. By the way, that is a dark horse 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 fuck with everyone so heavy in 15 years. Wine Library. people will be flabbergasted how involved I still am in the wine business. My best friend runs it. I am definitely one B to my dad and Brandon's 1A,

but I work on it every single day. One that's really under the radar, Vayner Watt. I have a very successful TV production company that's kind of brewing right now called Vayner Watt. We have a bunch of shows that have quietly just sold. So literally on Hulu and ABC and Netflix, like you're going to see Vayner Watt, VaynerWatt pop up.

And then finally, and I'm sure not lost on you guys, the NIL and brand of Gary Vee, I have a full massive team on it, speaking in books and content and NIL deals. Do you have ads or is it monetized via speaking? I did a deal with Stan Stone. I did a deal with Masterclass. 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 probably, I'm writing a new book called The Individual Empire, which talks about the me, the Bartlett's, the Alex Cooper's, the rise of the creator entrepreneur

and the entrepreneur creator as the next Fortune 500 companies and my belief with AI blockchain evolving social, you know, decentralization of Hollywood 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 a me where they can be both. Hey, everyone, really quick. If you're enjoying this episode on CEO stuff,

so delegating, having hard conversations with your team, hiring, then I've got something for you. So the team at HubSpot, they actually went and put together a bunch of best practices that Sean and I use in our own companies. And they put it together in something that's really easy to read and understand.

And so if you want to just save yourself 10 years of headache and heartache, then you should check it out. I wish we had this a long time ago. It would have helped me a lot. But there should be a QR code on your screen that you can scan or a link in the description. So check it out. It's totally free and totally awesome.

You just named like six or seven companies that are doing eight figures that you're like, I'm either the 1A or the 1B. And I think that's awesome because I too wish I had 96 hours a day. And so, you know, walk us through what does the day look like? What's the time blocking look like for this, right? Like what's a day in the life of Gary V to do all this? You know, I wake up at six or seven. There's a workout session every day-ish.

I'm pretty much an 8 to 8.30 to 9 a.m. star 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. 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 intuitive, and that I could convert Ds into Bs 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 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 shit, Vayner Sports needs me. Or shit, Vayner, like, There's all that. But the real reason is because of the 50 people from Ryan Harwood or Kalin or Claude or J.T. Or A.J. and Greg Gensky or David Rodolitz and Connor Hamlet or Andy K. and John and J.T. John Trowman and May and Rips on Beefriends or Brandenke on Wine Library or Eric Wattenberg, Bainer Watt, on that.

And I've got another one coming that I'll announce next year, standalone business. 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 Rezi. You know, like, people forget that I'm the co-founder, an inventor of Rezi, 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 consolation brands in 18 months, just like, you know, everyone's like Gruins.

I'm like, I did that, 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 seven to ten 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. Well, I was listening to your podcast this morning,

and someone asked a question that a lot of content creators ask. They said, I'm doing live shopping and live streaming, but I don't want to do this all the time, and I'm nervous that this all relies on me, and I want to get other content creators. You have listed six or seven businesses doing tens of millions in revenue, and all is started off of you,

and I don't know what percent is run, or you get customers still for each thing because of you, but a lot of it's based on you and your content. Do you get nervous about that, or do you not care? You think I just love this so much that I ain't going anywhere. 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 Haley Bieber where they need a business person to also be around. But then there's also, like, I mean, you guys are like in pot. You know, everyone has different hopes and dreams and say, you've nailed it.

Like, to me, like, I love this shit. Bro, you know, people go and buy a home in the Bahamas and play golf and Baker's Bay and that's their escapism when they need an escape. when I need a break from Vader X, which I do a lot because client services suck shit. I don't go to Aspen. I go to two days off-sides for V-Friends because 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. What's going on to these 15-minute meetings? Because I suspect what you're doing in, 15 minutes has taken most people an hour.

So maybe you have a format. I'm mad at you, bro. You took my shit. I was asked that I was about to say the thing that everyone else is spending an hour on. Bro, this is going to be one of the highlights that I know from this meeting, this podcast, everyone's going to, I love that I said meeting. This feels more like a business meeting. This is why you guys are so successful.

Everyone's going to say yes right now on the treadmill walking the dog in their car on a plane or however they're consuming this. everyone's meetings are twice as long as they need to be if they're a winner and they know it. You got slam poetry snaps for me. And I just went there. I knew it subconsciously. Then it became subconsciously. 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 on you guys, literally nobody really knows, which is wild because I'm Gary V and I'm talking 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, because you've got to have a backup and a backup and a backup, because there's so many variables that can go into these things. So the 15-minute meeting has been gangster for me, game-changing 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. What percentage of those meetings are you making decisions or being informed?

I would say 30% on being informed, 70% I'm making decisions. That's insane. That's hard. The contact switching, that's challenging. You know, it's funny you said that. I've got a bunch of new film people because all my people, this feels incredible,

go on to these incredible things after they film me for a little while and get all these offers or start their own things. And so I constantly have a DRock coming through 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 actually think that sometimes when I say contact switching, we had a guy, one of our friends came on the podcast, and like as we were doing the sound check, he got a text from his daughter saying she didn't get into the college that she wanted to get into, and it screwed him up. Like the rest of the podcast was kind of shaky because he was like, oh, I'm so sorry. I can't stop thinking about my daughter just texting this. I'm so sad for her. I think one, it's, it, 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 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, 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 Bainer X. 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've really gotten to 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 happened in my personal life, similar to the college thing, there's always something. And just like being able to like eat shit and firefight

is like a really strong emotional framework that is hard. What about notification fatigue? I tease Sean all the time. Sean, what's the joke? What's the stereotype if anyone wants to get a hold of you? Do you know what that stereotype is about you, Sean? Called Ben. I don't know. No, you, Sean will not reply. Getting in touch with Sean when you need to, sometimes it's a pain of the butt. With me, I tend to reply, but it wears me out. I get so exhausted because I feel like I want to please these people. Sean's like... The worst part is I go to him and I say, hey, long time, no talk when I think of somebody and I see that actually they have been talking and I haven't.

And I'm like, okay, I shouldn't even send this. Maybe I should just opt up. I would say I'm in between you guys. I try to reply a lot. I use flights quite a bit to catch up. And then if they can't get me, they get to the admins. And the admins have a good sense of my reality.

How do you decide what projects to go into? Because, you know, for the six or whatever you said that are working, obviously maybe a couple didn't work. And then there's hundreds of opportunities you're saying no to. So what's the bar now? What's the box? How do you think about that? My tummy.

Just gut. Yeah. Like, I want to do this and I want to do it with this person. Say that again, Gary. Say it cute. Like what you said tummy. I don't have gut instinct. I got tummy tickles.

You know, there's so much serendipity to it. I'm very comfortable dying on my sword, which is my intuition. I'm very comfortable. Well, have you guys ever came close to bankruptcy or not be able to make payroll? You know, it's funny, but make payroll. Rezi was in trouble. I had to put personal money in that I didn't really have at the time. But nothing I've ever operated as the 1A.

You know, I got trained by a Soviet immigrant father who didn't even, let it know, raising capital, forget it. Debt, forget it. Literally didn't have a credit line. And we were in the liquor business where you had to legally pay your bills on 30-day terms where you went on COD to the whole industry and you couldn't get product.

So I think I got trained so well, you know, always have money in the bank for a rainy day and 30-day terms legally bounded by the alcohol laws of America and no credit line that by the time I went to my own journey full-time, it was in my subconscious of like, well, you always have that money. The end. All right, let's take a quick break, and I got a question for you. When a buyer asks AI for a solution like yours, does your business come up? Most companies have no idea.

And by the time they found out, they've already lost the deal to another company that did. HubSpot has AEO, which helps you show up in the moments when the rag buyers are looking for a company like yours. Before the first click, before they fill in the form, that is the moment HubSpot AEO is built for. Check out HubSpot.com, the agentic customer platform for growing businesses. You meet a lot of people. Who do you think is doing cool shit right now? What are, you know, either businesses that are kind of blown your mind, maybe something that's taking off faster than you would have expected, maybe something totally unrelated to what you do. But, wow, you know, you get exposed to stuff. that the average person doesn't.

Where are you seeing a lot of heat right now? There's so many good areas. I mean, like, you know, I'll answer a question that might bring, I'm trying to think about how to bring the most value to the audience. I'll go to places where people are betting on five years from now, not to create an exit five months from now. So that takes me to people that are really spending time on advanced AI,

like really knowing where the stigma is today, but won't be in five years, right? Like creating an entire agency of virtual people, right? Knowing right now it's a little weird, but let's survive three to five years, and we're going to have the CIA of virtual people. They're all going to be the most famous virtual people, and we own it.

You're in the IP business, not the representation business. That I like. I love everything, and this is my wheelhouse, but I love everyone who sells something to the consumer that realizes what live shopping is doing, in the e-commerce is what e-commerce did to real life. And so what I mean by that is like in six to 10 years, you know, I think e-com now is what, 25, 30% of the market.

Like in six to 10 years, live shopping will actually be 10 to 15% of all commerce. And that is scary big. Did you invest in what not? I did not. I obviously talk about one not all time. It's not an investment. How? How is it possible?

You've been talking about live selling for years. And you'll love this. Any time I've invested. in something that I end up having to talk about a lot, I make a lot of content up front that I'm an investor. So the way you know if I'm an investor in something is I'm saying it a lot early on. Because I never, so, you know what?

I'm sure everyone thinks I did. And by the way, it ran through my table. Like I don't, I wasn't actively investing at the time, which is the answer, Sean, to why I didn't. And I know it crossed my desk, but I never took like a meaningful meeting with Grant, but I'm so happy for him. He started a great job.

I'm happy for the people that invested. I think, Sean, didn't they ask you to invest in the Seed Run? You forgot to reply to the email? No, no, no, no. That was a, that was a, not a, finally one I didn't shoot myself in the foot. Somebody else shot me in the foot. I met with Grant. I was like, I love this.

My last business got acquired by Twitch. I'm amazing. Have I told you how amazing I am? You got to let me invest. The round it, like, just closed. But a lot of times, they'll let you in if they like you. They'll open it up or they'll squeeze you in. He was just like, let me see what I can do.

And I didn't hunt to chase it down, like 10 times more. And I just let it go. And, you know, that's a big miss. I have a great email in my inbox from Joe at Bedibbett and Breakfast. AirBred, yeah, I'm trying to remember, was it? Yeah, airbed and breakfast.com. That's a good one. Do you have any other ones that you haven't talked about?

No, you have Uber, obviously. That's the famous one. Airbnb, but I never saw the email so it doesn't hurt. Oh, Pinterest. I had a guy who was the CSO, the chief strategy offer at Campbell Soup, who was like 60 years old, said, Gary, you got to look at this startup. from Pennsylvania.

That's how he said it. My friend's cousin knows the guy. I'm like, okay. That's like, I got a guy. That's like getting a script for Hollywood in Chicago. You know, I didn't even like contemplate it. Yeah, so that was close. But I got in later through Scott Belski.

What a great investor he is, by the way. He invested in, I think, Uber and Pinterest in the same couple of weeks, both at a $3.5 million dollar evaluation. Both was like $25,000 checks when he had like, like, 75. He told me he had like, he's like, I had 75 grand in personal savings, and I put 25 in each of those companies. Yeah, which it's like eight or nine figures. And by the way, he's better than that even. Like, he's got more wins. And he's an operator. He's one of the best. Yeah, I mean him. I mean, Matt, you know, one of the reasons I'm starting my next thing is a lot of CPGs, magic spoon.

A lot of good brands came to Vayner wanting us to be the people, but we didn't take on those kind of clients, some things I invested in, some I didn't. I want to be better at that. My biggest win that I don't deserve is going to be liquid death. Mike worked at VaynerMedia the day before he started liquid death as a creative. And he sent me an email and said, hey, I'm leaving. Thank you for your time. I learned a lot here. By the way, I'm doing this thing. Would you like to invest? He was a creative. I'm a cliche businessman that thinks creatives aren't business people, right? So I was like, you know, and I didn't know him well enough because we had a big company at that point. Well, he's also saying that he's launching a water company called Liquid Death.

Like that is like a silly thing on paper. You'll appreciate this. The way I think about branding and marketing, it actually fits me more than it doesn't. For me, the way I like stuff. So that wasn't the crazy part. I was kind of agnostic about that part. I thought it could work, but I didn't think it was brilliant. And I definitely didn't think what a lot of people thought, which is it has no chance.

Because on consumer brands, marketing is a stunning variable, especially if the product's a commodity and water is a commodity, right? like water in plastic versus water in a can doesn't really change the variable. In fact, the can is the advantage. So I understood that part. It was more interesting why I invested. It goes back to this nice guy theme a little bit. I just wanted to invest

because I want to support my employees on their own ventures. So I literally did it for that reason only. And, you know, that's going to be a fucking mind. It was first check in. Today's podcast is brought to you by my friends at Mercury. They make the world's best banking product. I think you know this already.

I use Mercury for all of my businesses. I think I have like maybe seven or eight businesses. We use Mercury as our business banking across all of them. And now they actually just launched a personal banking account. So I have my personal account there. I moved off of Wells Fargo and Chase. I'm just all in on Mercury. Why, I like products that are easy to use.

I like products that get me and the problems that I have. So like very easy to make a joint account with my wife. Very easy to spin up virtual cards. One click and I get savings yield. It just has all the stuff that I need in one place. So if you're looking for the best banking product on the market, it's definitely Mercury. I will fistfight anybody who disagrees with me on that.

Go to mercury.com slash personal and learn more. Mercury is a fintech, not an FDIC insured bank. Banking services are provided through Choice Financial Group and column N.A, members, FDIC. You're significantly larger than both of us, but we sort of run in the same world. And there's a lot of scammers and shady people in this, like, content and business world.

Like, I've noticed that as we've gotten bigger, I try to be very careful about who I associate with. Yeah. Being a nice guy, do you struggle to, like, say, I don't want to be around this person. Like they have a background of doing X, Y, and Z. Or they don't, or they have political beliefs that I don't buy into and I don't want to be associated. I'll be on.

And you guys know, as I never talk politics. Political beliefs won't throw me off because I'm very empathetic that people can see the world. I mean, hate or, like, ridiculousness on both the left and rightism, as we know it today. Sure. But like, political beliefs, no. But I don't think they do honorable work. Sure. I've struggled with that.

And also, you know, me being on the speaking circuit for so long, sometimes those, you know, those kind of characters might be at the same place and they want a quick selfie and I don't want to, you know. That's what I'm talking about, yeah. Yeah, and you know this. You know, you're smart. And so I know that question is grounded in, you know that I've avoided a lot of stuff and association.

And that's the reason. Yeah, of course, you never, I mean, there's people, the amount of people that will take a cell, forget about people we know. there are people that are tier 19. People that are trying to do this, they have like four followers and they sell a $4,000 course and they're criminals, right?

They'll take a selfie with me at the airport and then make a post and say that like we had a meeting at the airport to strategize their mastermind. Well, they did when they asked you a question, I guess. It's really, you do have to be conscious of that and you do need to worry about your NIL

and your reputation it is on my mind and now with deep fakes and where this is all going. I think about that stuff all the time because when I think of the Epstein files, because I'm like a huge true crime fan. And so I've seen the Epstein files, like the J-mail, you know, you can like go through his email. I'm like, I always want to be so careful about who I'm speaking with. It kind of freaked me out. Man, I will tell you, and you guys know this, I make a lot of content about my mom.

And like it's just I can't help not say it. Like you just talk and everything that goes to my brain while you were just saying that thing on the Epstein thing. Because I think about that too, I'm like, Who's even mailed me through the years and what? But the thing I can rely on, Sam, is I am not cliche human, meaning I don't say, like, things that are not nice. Like, definitely not in writing, you know, like, you know, and so like, I don't worry about that. Luckily, and in August credit, how I was raised, like, I really believe being the bigger person, being a nice person. You know what's really interesting?

Actually, I want to ask you guys a question. This blows me away. We are fortunate. We've worked hard. We have talent. we're at where we're at, and what that allows us is to spend some time

in private and public settings with other people that have won. The thing that completely rocked me and when it was happening to me in my contemporaries, my era, was how many winners, and I mean winners, they've got the girl,

they've got crazy money, they've got it. We'll actually still spend most of their time shitting on other winners out of envy or I don't even know one. And I'm like, this energy, like, I'm like, what, like, I had to say this to a couple of buddies not too long. I'm like, you guys are a bunch of 14 year old bitches.

I'm like, what are you talking about? You should be happy for X, Y, Z, that they're crushing it. Yeah, he's not the nicest ever, but he's not a piece of shit. And by the way, everything you're shitting on, you guys do the same shit. What is this? Like, you're winning. Like, focused on winning. If you're so actually sad that they won even more than you, and you got feelings.

feelings about it? Why don't you take these three hours of bitching about this person like f*** yenta and go build something? Well, Sean, what percentage of incredibly successful people do you know who you think are good, wonderful people with good attitudes? I think they're good wonderful people with good attitudes, but they're definitely imbalanced in some core way, right? Like, they're not well-rounded, chill-ass, you know, people, right? I think you're unlikely to be extreme winner without some version of an extreme personality. Sure. And, I think that's fair. Hunter S. Thompson said, he said,

there's no reasonable people on the top of Mount Everest. Yeah. Gary, I had a person kind of point this out to me about why this happened. So I don't know if you've ever read the René Gerard, like, Mimetic theories. Like Peter Thiel's really big on this. It's basically the core thing. You'll get this as a consumer

guy, which is that we don't want what we want because we want it. We want it because other people want it. Yeah. For whether it's your luxury bag that you're carrying or I believe in that. In fact, in fact, this is where all my gratitude comes from. Mother and DNA, I want it for my process, not because others want it.

And it makes me feel simple, but it's very clear to me that most are the other way. Yeah. So I think most people have this sort of memetic drive, right? And this is why you see trends and fads catch on because I want to go buy needos right now because all the other kids are buying needos. And I want to say this because other people say this. I want to wear Jordans because they wear Jordan. Right. So that's like a normal thing.

there's another term in that philosophy that's called a memetic rival. And so I was on a, I was on this plane ride and I had this embarrassing moment where I was admitting to somebody. I was like, you know what?

I feel stupid even saying this. But God, it kind of drove me nuts the way this guy was saying that. I was kind of bitching about somebody, which I rarely do, but I was doing it. And I was like,

honestly, I was like, guys, I feel stupid saying this, but like, that shit bothered me. And he goes, you know what? He goes, that person's your memetic rival. I go, what's a memetic rival? Basically, it's like,

I don't know if you saw when Bezos was launching his rocket, and Elon's launching a rocket. And then they had this really passive-aggressive thing. It's in Elon's biography. It's very funny. It's like, congratulations to Jeff on the first suborbital launch. And then Elon landed it. And he's like, congratulations on the first successful landing from only a, you know, two megaton, whatever. It's like they added these little qualifiers.

They started blocking each other because for each other, they're memetic rivals, right? And it's just a very strange thing. You think these are the most secure people on Earth, but we all have a core part of us that has it. It's how you learn to tame it and live with it. It's funny. I literally believe the reverse. I genuinely believe that the far majority of people

get to the top from extreme insecurity. Hey, let me ask you one more question. And you don't have to answer if you don't want to, if it's too private. But with the six or seven businesses that you've named, they're badass. And I'm looking at the people you hired, or I guess they are your co-founders.

they're freaking awesome. And I was looking at some of your partners and your other businesses. In order to get these off the ground, do you have to fund them personally or do you get backers for a lot of these things? Because it's not like I'm reading this deadline article and you have like a list of like five or six people

and they're ballers. And I'm like, those guys aren't cheap. And he's always... Steve Ross, the owner of Dolphins, who's in Vayner Media with me as well. He funded that. He wanted to be a part of that. On the rest, I funded.

That's awesome. Like I was looking at the... I didn't know about that you had a restaurant. And I was looking at that and it looked like a membership club and I looked at the interiors and I was like, no. It was a meaningful build out. Like, no, it's been really cool. Like I'm in a really fun part of my career. I'm actually, I actually just used this platform, this incredible platform.

So thank you for having me. I'm talking a little bit more because I actually want to start talking a little bit more about me, the juggler. To your point earlier, I am proud of what I'm doing. And I, you know, no one really knows, which is wild. And I'm proud of that too, right? That goes to the humility. But now I'm maybe ready for being like, hey, guys, by the way, I'm not a motivational speaker.

Right. Might actually be a weirdly good operator at scale. Well, Sean, Google Fly Fish Club Manhattan or just Fly Fish Club. And please come when you guys are in New York. You'll be blown away. I live here now, Gary. I live on the other side. So like ASAP, email me after this.

Like, ASAP, ASAP, I want you to see it. It's a three-story restaurant with a private posse room. Like, it's real. But more importantly, because you know this, It could also be going out of business tomorrow, meaning it's a, like the business is extremely viable. In fact, Sam, now that you're here, upper west side, if you just go over to GW, which I know is counterintuitive, the restaurant we opened in Bergen County, New Jersey, called Capons Chop House, we now know we're about to open another one in Westchester.

We're about to open 50 of those in high network neighborhoods of the biggest cities in the world. We got the model. We got it. And don't forget, this is the brilliance of what I think. when it's all written, the Vayner X marketing machine impacts all these businesses, right? What's the model?

It says that it's a membership. The model is open up the new version of Ruth's Chris and like the best steakhouse that has the most New York City vibes, just not in New York City, and everyone in bridges and tunnels

of the seven most important places on earth that have high net worth individuals are going to sell the shit out of these places. It's not a new invented model. But it's a member? You have to be a member? Capeons is just a Ruth, Chris Steakhouse 2.0, but we have a very strong, what we do,

to Eugene's credit, to Grutman's credit, to Noah's credit. Those places have, they know, cool, right? There's that nightlife element. We're going 20% less on that and 20% more on food. We think the secret to retention LTB is just execute a food program that is so undeniable, and a little bit of that sizzle, but your steak's got to be right, right, right?

Our strategy is killer chicken parm. It's like, yes, actually, that's kind of what people want. You've gotten into this business genius. He decided to start an agency and a restaurant. The two best businesses on earth. Literally the two worst. And again, this is a great way to end it up, which is like, I'm playing for what makes me feel good,

not just maximizing the dollars. And then on the other side, I'm going to turn V-Friends into Pokemon, and it's going to be one of the most valuable intellectual properties in the world in 20 years, which in an AI world will have an extraordinary amount of value and will be the best kind of business someone can build. Well, we appreciate you, man. You're the shit. Thank you, guys.

Yeah. May well. Wish you well. All right. That's it. That's the pod. I feel like I can rule the world. I know I could be what I want to. I put my all in it like no days off. On a road, let's travel, never look at that.

Hey, let's take a quick break. I want to tell you about a podcast that you could check out. It is called The Science of Scaling by Mark Roberge. He was the founding CRO of HubSpot. And he's a guest lecturer at Harvard Business School. The guy's smart. And he sits down every week with different sales leaders from cool companies like Clavio and Vanta and Open AI.

And he's asking about their strategies, their tactics, and how they're growing their companies as head of sales or chief revenue officer. If you're looking to scale a company up, if you're a CRO or a head of sales that's looking to level up in your career, I think a podcast like this could be great for you. Listen to the science of scaling wherever you get your podcast.