From Family Business → Building Million-Dollar Companies (and What's Next with AI)

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 I was an all-American football player, was the youngest coach in the country at Arizona State.

1:35And when I got fired at Arizona State, I got a couple months of doing nothing. And I was listening to Gary, we had all the experience every day. And was hearing you talk about TikTok, decided, hey, I have all this experience in football. I should start making TikToks. Started it three years ago. And it has grown into something kind of big. So if it wasn't for that and hearing you talk about it, I wouldn't be here doing media. So I'm excited to have you on. Well, I'm thrilled to be a small part of your journey, and I'm thrilled to be on. I appreciate it. I want to start with this. We're at VaynerMedia headquarters, VaynerX headquarters.

2:05Just think about how much you've built in your career. What's the most defining moment of that journey so far? Is there one moment that you said, that wouldn't happen, we wouldn't be here? There's a lot of those. When I think about defining moments, thank you so much, I don't think of it from a standpoint of like, oh, like this day that I just, this moment, when I went on YouTube and started of the wine show when Google bought YouTube for$1.7 billion, which at the time, to give you all context, would feel like a$500 billion exit today. Like just to give you inflation, just like no one could believe this number.

2:41I remember promising myself, that was a defining moment, even though it kind of didn't involve me at all. I promised myself that the next time I would see something big, that I would invest in it, not just use it. Because I was right about email, I was right about dot com, I was right about search. I was right about YouTube, MySpace. And so I saw Twitter and I invested in it. And I would say that in a lot of ways that moment was defining. But I would say that that's kind of like my fake answer, meaning that's the right kind of answer in the context that I think you asked it. I think the defining moment probably for me in my career was calling my mom in college freshman year and crying to her that I didn't wanna go into, since I was 14 I said I'm gonna go into the family business and blow it up.

3:36And then at my freshman year of college, I had this, I've never really shared this story, so I'm giving you some alpha. I kinda had this moment where I was like, damn, I know I can do my own thing, like am I willing to pay this sacrifice because it's not going to be my own thing. And even at that age, even though I've always been confident, there was a part of me that said, well, will people be like, even though I know I'm going to build this business for my dad, but I never get to get my own credit. You know what I mean? And so that conversation, I think, when you asked it, popped in my head.

4:11I have a very unique career. I spent every day of my life from 22 to 34 building a huge business for my dad and left it with nothing. That's weird. like I don't see that story out there I see a lot of immigrants just stay in their family business and eventually inherit it so you know there's a lot of moments like you know showing up on Dignation when that was like the biggest internet show in 2007 put me on the Twitter map the Conan O 'Brien appearance I was kind of one of the first internet people to make it to like television AJ walking into my office and saying he's quitting when I always thought he would be the one that would run this and I would go on to do something, you know, which led to VaynerSports, you know.

4:52I mean, there's so many, brother. When you were in your family liquor business, did you know that when you left to start your own business it was going to be an agency that whole time or you were gonna be in the media space or that came from your kind of exposure? I had no idea when I would leave. You know, probably 1 % of me didn't even know if I would leave. I knew my brother was growing up in a manner where he did not have the same level of relationship with my dad. I knew that he didn't want to be in the business. I knew I wanted to be in business with him. He was 11 years younger. So 29 was, you know, watershed moment, and then ultimately 33, like really, because that's when he was actually done with school.

5:35That's when we started Vayner. No, I didn't know what it would be. Like, I just, I mean, I never even thought I would be known. you know unlike being an athlete where like you when you're like when you were growing up being this great athlete you knew there was a potential that if you achieved your dreams that you would be known I wanted to be a businessman in the 80s and 90s none of them were known the world was so different for the kids under 35 you can't even comprehend what like life was pre-internet everything was 100 % different like in a way that you can't understand like in a way that AI is about to teach all of you Like in 15 years you'll be like, how did we live in a world without AI?

6:15So no, I had no clue what I was gonna do. But I really didn't think about it again after that phone call when I was 18 until I was about 28 when I had my first marriage and I was like, oh I'm a grown up now and I have another family to take care of and I realized I had no value. Meaning when I went to go get an apartment, they were like, yeah we're not giving you a loan. I'm like, but I built my library from three to 60 million. They're like, that's nice. Your dad owns that. You own nothing. And that was like a, that was a watershed moment where I was like, fuck, you know, I was so obsessed, brother.

6:52You know, like the athletes that actually make it to the league, there's an obsession. I was obsessed with building a business for my parents. Nothing else mattered. Not my life, not my, I'm being serious, not like friends, not like my own joy. I got into this really cool place where I just super appreciated what my parents had done for me and I thought I was super talented and I believe in the shit that I pumped all you kids. I believe in patience. I didn't think if I gave up my 20s that I was ruined. I took a lot of judgment. My high school buddies coming to the liquor store when I was 25 and like, you work for your dad?

7:31They're all making some money. They're all starting to make a little money. They're all kind of looking down at me like I'm the help at my dad's store. but I had like a real vision and a real game plan. When you think about the first couple years of VaynerMedia when you and AJ started it, what's the biggest lesson you learned during that time? That I was unstoppable. I'm being dead serious. The first two years I was barely involved in the business and we did 1.7 million in revenue and the first year I ran it we did 11 and the next year we did 27. I'd done it at Wine Library but to do it again I was like okay.

8:05Like honestly, I know that's like a weird answer and I kind of keep it humble, but like I feel comfortable giving you the truth. What did I learn in the first couple years? That I was that guy. That like whatever the fuck I was gonna do, it was always gonna work. I knew nothing about advertising industry. I knew everything about advertising, but not about the industry, not about Madison Avenue. That is no question. Those first couple years, especially 2011, 12, when I became the CEO, instead of like still doing Wine Library, still starting to build Gary Vee and working with AJ, I, that was it.

8:38I was like, you know, like anything, when you do something great or good, when you do it a second time, you're like, okay, this is not luck, this is not serendipity. And now I was doing it starting it from scratch. You know, so even that level of doubt, like can I do it from zero to three, was put to bed. What was the process like of getting those first few major clients at Vayner? Were you like hand-to-hand combat? Yeah, hand-to-hand combat. Yes. I had customers from Wine Library who were buying expensive wine. I'm like, you're rich. Do you have marketing needs? It was kind of like that. I was already known for marketing Wine Library.

9:14The way I became liquor store industry famous was I was the most progressive marketer. I had the first website. I did email first. I did YouTube show. So just hand-to-hand combat serendipity, relationships, drinking wine, networking, emailing people, straight hustle grind. If you could go back right now and give yourself advice on those first couple years, knowing what you know now, what would it be? It's a more macro answer. I would tell myself that what you've done poorly at Wine Library is what you're going to do poorly at Vayner. And the sooner you fix it, you'll be better. And that is you need to be able to deliver bad news to employees you like.

9:53I was not candorous enough in the first 20 years of my career. What would end up happening is people would be surprised when they got fired. My greatest joy, the thing I'm most proud of is that I'm big on eliminating fear. It's like why we have such a good culture. People aren't that scared. But having that day when I realized that people not knowing if they were gonna get fired at the senior levels actually led to fear was one of the most humbling days of my life. Truly, brother. Like one of the most humbling days of my life where I was like, fuck, you take so much pride in this and one of your flaws in your personality is actually creating this.

10:30So I would tell that person, get your candor game up. You're great at candor as Gary Vee. I shoot it straight as fuck in this environment on stage. Every piece of content all of you have seen, I fucking crush. In real life, Gary Vaynerchuk, if he likes you, which I like everybody, the more you've been around, I struggle with that. How'd you change it? How'd you become more candorous? You just started being more honest. Professionally and personally, I realized that candor was leading to all the things that made me sad and all my unhappiness and all my negativity and all the things that weren't working for me and I decided to fucking change it.

11:05Like the same way I decided to change my health. At 38 I was like, okay, this is gonna lead to like death and like, you know, like let's get to the gym and let's eat better and that doesn't come natural to me nor does being candorous but I put in the reps and I work and I practice and by the way, I put myself on blast. I put it out on here. You know, what I'm doing right now is suffocating me. You know? Yeah, it's even no choice. You gotta do it. Yeah, I think a big way to change everything in your life is to tell everybody around you and anybody that's willing to listen your shortcomings. That will put you in the corner in a real way.

11:43As far as the business operation here at VaynerX, I'm fascinated by how you've structured everything, how you have, you know, we walk through here and you have every kind of, every wing of this place is a different entity or a different business operation. can you give me the breakdown of VaynerX, the businesses underneath it, and kind of how you decide what falls under VaynerX, what falls outside of VaynerX, the holding co, like VaynerSports, from what I understand, right? And VaynerWatt, which is a TV production company. VaynerSports was necessity. The only investor and partner I have in VaynerX is Steven Ross.

12:13He owns the Miami Dolphins. When you own a football team, you can't own a piece of an agency. So VaynerSports would have been inside of VaynerX had it not been that situation. Under VaynerX is VaynerMedia, which is the mothership. Then there's something called Gallery Media Group, which owns PureWow.com, which is a women's, and Covetor, which is like women's lifestyle magazines on the internet experiential agency. Stuff work in there, but it's a publisher. Kind of like Condé Nast, Hearst, just smaller. VaynerSpeakers, our speaking bureau sits under there. VaynerCommerce, which is an e-commerce specialty agency.

12:52the Sasha Group which is an agency that originally why it's named after my father Sasha was intended to service small businesses now it's just become another VaynerMedia in fact I'm contemplating a name change it's become another VaynerMedia so VaynerCommerce the Sasha Group and then there's Tingley Lane which is a barter media company where like you take assets and you turn into media Iva Nosadam which is Madison Ave spelled backwards which is a thank you which is a production company They all sit under VaynerX. Then there's Vayner Sports and VaynerWatt, which is a TV production company, where Steven actually, Ross, is my partner in it because we blend a little bit, but it's not in, because Eric Wattenberg needed equity, it sits outside.

13:36Then there's the VCR group, you know, my great club downtown, the Fly Fish Club and Little Maven and Ito and all our restaurants, so that's a restaurant group. I'm the V in VCR that sits outside of VaynerX. V Friends sits outside of VaynerX, My pickleball team, the fives, is another big part of my life. In Major League Pickleball, that sits out of it. And then all my investing sits out of it. So when you think about a new business vertical, you have kind of spun up a different business for that underneath the Holy Coat. As opposed to kind of just keeping all under the VaynerMedia brain. Yeah, I think there's times.

14:09And I debate it all the time. Should I consolidate in? Should I spin out? There's just times where things make sense sitting in. We had an innovation company called Vayner3. We did NFT work, blockchain, AI, but we spun that back into Sasha and VaynerMedia because we thought it was core. Yeah, I mean, I think different times, sometimes it's because of executives. If you have somebody super talented that you think can run something, that's what Vayner3 was with Avery, who's our CMO now. So, you know, I hate Bill Belichick so much, so I hate using this analogy, but I remember when Bill Belichick took wide receiver Troy Brown and converted him late, late, late in his career to play some plays in the secondary, I just remember thinking like, fuck, that's so smart.

14:58You know what I mean? Like, if you can, why not? And so I do that with executives. Like, I definitely do not textbook stuff by reverse engineering. I assume in that scenario, Troy Brown showed Bill things in practice or in film work that he could do it. I look at the same way. Like, If I think someone could do it, I'm willing to contemplate it even though the world doesn't think that's the way you do it. One of the things I'm curious about, you mentioned the executive piece. One of the biggest roles you have is hiring, is identifying talent, right? Yeah. What's the best hire you've made in the last couple years?

15:33That's a great question. What's the best hire I've made in the last couple years? I can tell you that the best restructure I've done is putting JT, John Turana, and Marcus Krizak, my former chief of staff, to run international. I made a real switch to create president roles inside of VaynerMedia. That has really worked. I elevated Kaylin McNamara from account to new business, and now she's our chief business officer. I think Avery into the CMO role has been very effective instead of running LATAM. So I've made a lot of switches that I'm really happy with. hires, net new. Grace, our creative lead in Canada, good hire for sure.

16:22Jessie, her boss, who runs the Canadian office, good hire. Casey, she runs Australia, good hire. Oh, Victoria, my head admin, was a great hire. Really has shaped up that universe for me in a great way. What do you look for when you're hiring people? What tells you ahead of time that I think they're gonna be a good fit. A mix of like, do I think they're nice? Like I really struggle with people that are overly political. I look for my intuition on, are they nice? Are they confident? Because if you're insecure, many people are nice, but they're insecure, which then creates political behavior. Are they capable?

17:04Like do I subjectively guessing think they're capable of doing the job? Do I believe they have a solid work ethic? I don't expect people to work like me, but if you're jonesing in your seat at 4.30 and can't wait to punch out at 5, that's not it. Do they understand if they get in here, it could be the beginning of a 40-year career in 10 different companies and that I create lanes from. I was a DNF student. I was a kid from the muck. I don't even know. Do you know I have no clue what college any of my employees have gone to? Outside of their big sports, I know Ross went to LSU because he fucking wears an LSU jacket every day, but like if you told me give me$43 trillion to tell me right now where Mike went to college I have no did you go to college?

17:46Yeah like no clue no clue so I'm not really looking at resume shit I'm looking at the conversation and do I feel good about them. To be able to do a lot of different things it sounds like you've built some really unique like admin support to handle I mean even just scheduling this where assistants and chief of staffs and different people that support it what's that look like? It's a pretty big operation. Yeah I have three three full-time admins, or two full-time admins, and two chief of staffs, one's the head of the admins, and then Hannah, so I have four full-time people just on my logistics.

18:21Yeah, I mean, it's four full-time people who like really work, no nine to five life. So yeah, and then we're using AI more and more to be more efficient, every minute counts. When people talk about Gary Vee, I feel like you're synonymous with hustle culture and grinding and sacrificing to get where you want. But as you've gotten older, what have you learned about balance and the impact it has on you? You know, it's funny, honestly, if you go read, if you go look at my content in 2009, 10, 11, 12, I think people like when I scream about that stuff. But I don't know, there's a lot of people that make fun of me of being too foofy.

19:01I don't know, I've been balanced. I don't know, I've slept seven, eight hours a night my whole career. I check the fuck out anytime I feel like I want to. I take seven weeks of vacation. I just go super hard when I'm awake. And by the way, who gets to decide balance? Me? You? God? Who's in charge of balance? Actually, here's a good question. No bullshit. How old are you? Third. And you're single? Girlfriend. Girlfriend. No children. No children. Real talk for fun because I think this will be helpful for your audience. What do you feel balance is for you, work-wise, at this point in your life? I want you to define balance in hours of working in a week.

19:44I'd say if I can be 50, 60 hours a week. Yep. I'd say if I can be done working at like 7 o 'clock. Nice. And when do you start? 9 a.m.? Yeah. And that's five days a week. Yeah. Right? I think 9 to 7, Monday through Thursday for sure. I don't know how you deal with your Friday. like if that gets a five versus a seven. Yeah, right, life events with a girlfriend. Like, I don't know. I mean, that feels, to me, that feels light. For me, by the chemicals in my body. Not ultra light, just a tad light for me. By the way, for a lot of people watching, that felt too much. They're like, what are you doing?

20:27Like, you're gonna regret that you're, you know, they think you should be nine to five. Maybe even nine to five Monday through Thursday. I don't think I'm right I definitely don't think they're right I think you're right for you and I think that's awesome I don't know like who gets to decide does your girlfriend think you're balanced or does she think you work a little too much she knows I work a lot but understands I think the difference too is like to me that is what I would identify as balanced but I'm in a phase in my life where I don't need to be balanced right now I'm building no shit why do you think I feel it's light that's my point of view but I don't think I get to be right on you.

21:03I don't think I'm like, like I also don't know you well enough to know how big your ambitions are. How big are your ambitions? Pretty big. Meaning, give me something. I want to build a 100 plus million dollar media company. Nine to seven Monday through Friday might be a hair light. Are you super checked out on the weekends or are you in it? No, I'm working more than that. I would say that's what I would identify as me being balanced. I am not balanced. Respect, respect. I'm saying that if I wanted to be balanced, I'd be nine to seven but I'm working weekends, I'm working. Heard. Heard. Makes sense.

21:34You're trying to build a hundred million dollar thing. Fuck man, I respect that. Got it. Note now, I would say, it's funny, you and I are similar. I would say Monday through Friday, nine to seven is balanced to me too. Like to me, that's like the kind of like watermark if you're like trying to be like upper middle class of the world. I don't mean upper, like just like if you want to build something, if you're doing something, like as an employee where you've got like a, you're a country club person and you have a second home and you have a pool. Work is like a thing. But by the way, I'm also very big believer that the people that go nine to four, like the French movement, like I actually, people are stunned when I talk about this in detail.

22:15I'm like, good for you. You don't think I can feel in my body what it would feel like to be a nine to four guy with a one hour lunch and like enjoy the shit out of that? Like I was lazy at school. I like didn't do shit in college. Like I know what the leisure life feels like. It's good. I just like what I do too much. Like, you know, to me this is playing a sport every day, right? It's like playing a game. So yeah, for me, I agree. But I don't think a lot of people would agree with us that nine to seven, Monday through Friday is balanced. I think they think, I think most people think nine to five.

22:49And to be frank, I think with post-COVID, a lot of people even think a half day Friday in there, a work from home where you're actually working three hours. and by the way again I will say this I just want incredible clarity good for them the only thing that I say to a lot of them is like when you go to the gym if you do a real workout for an hour proper seven days a week including in those seven days two days or stretching like the right shit and I go to the gym and I lally gag three days a week we shouldn't have the same muscles and that's how work is so if you're gonna go go for leisure, shut your fucking mouth about what you feel like you're entitled to because that's just how life works.

23:34And I know a lot of people were mommied and dadied real nice, but that's not it. I'm a big believer in life. Life's all about momentum, especially in business. I'm a big momentum guy too. And once you have momentum, you have everything to keep it, and as soon as you lose it, you gotta get it back as fast as possible. Are there any moments where you've lost momentum? I got to get it back. I lost momentum at 28 because I think I went through a period where I fell in love and, I mean, this was in work. I mean, in life, it was great. Falling in love, that's great. But I was starting to build a little resentment towards my dad.

24:08Right? Because as you can imagine, as I started to become into another relationship with like, I'm going to build my own family, kind of all that, you know, I built a business from three to 60 million and made nothing. Nothing. Nothing. And I worked 100 hours a week, actually. You know, 9 to 10, Monday through Saturday, 12 to 5 Sunday. Real talk. So you can imagine when people are like, I'm like, okay. You know, like, I feel like I lost momentum on the Gary Vee brand last year. I was so head down building VaynerX and VeeFriends. In fact, why I'm even doing this is I'm starting to get back out there.

24:43So that's been fun. Like, I like losing momentum. Because I like the restart. I don't beat myself up when I've been like eating well and working out well. and then have a bad four months, I'm not like, oh, I fucking blew it. Four years for, like, people do that shit. I'm like, no, no, no. Like, I can get this back. And I like that challenge. I feel like I see and feel a direct correlation between when I'm popping off the most on content, the business things, the opportunities, the money-making opportunities, they start to just come out. Well, why the fuck do you think I've been yelling about it for 15 years?

25:17But when you say you love false momentum on the Gary Vee brand, do you feel the impact of that on other businesses? No, because there's a different version of Gary Vee. There's the operator. Right? So like in a lot of ways, I feel the momentum of it because I was head down making the businesses sound, staffing, restructure I just met, right? So yeah, by the way, I do feel it. Like less speaking opportunities. Like if I'm, like anybody who's out of the attention graph is gonna have less things. I feel it. I feel it. But it's, you know, so easy to get back if you're good at it. Again, like a great app, like I don't love the gym, but like someone who's actually in shape and like always like, again, you live, actually you've probably gone through this journey in a real way between 22 and 30.