Being a Great Operator Is My Biggest Vulnerability | Gary Vaynerchuk

The Entrepreneur DNA

Gary Vaynerchuk discusses the transition from being a hands-on operator to managing a massive holding company empire. He breaks down the str

Key takeaways

• Gary Vaynerchuk identifies his strength as an operator as a primary vulnerability to scaling his business.
• VaynerX serves as a holding company for entities such as VaynerMedia, VaynerSports, and VaynerWatt.

Main topics

• Business scaling and operations
• Social media algorithm trends

Notable quotes

Me being such a great operator is my biggest fault.

Conclusion

The episode provides a masterclass in navigating the complexities of s

Transcript preview

Speaker 2 (0:00) For many of us, going further isn't a choice. It's a feeling we can't ignore. Because ambition has a way of outgrowing where it began. Turning dreams into direction. Every journey brings us closer to the life we imagine. So, where will your journey take you? Etihad. Beyond Borders. Who Speaker 4 (0:30) does Gary Vee go to for advice? No one. I had to come to a hard realization in 2024. I mean, financially brutal realization. That I'm not an operator. Speaker 3 (0:41) Me being such a great operator is my biggest fault. Speaker 4 (0:44) Gary Vaynerchuk. One of the world's leading marketing experts. Entrepreneur and bestseller. A New York Times bestselling author. Speaker 1 (0:50) And is one of the loudest voices on the internet. Speaker 4 (0:53) Gary Vaynerchuk has been telling people what's about to happen on the internet about three years before they're ready to hear it. Speaker 3 (1:00) Here's a data point that's not subjective, it's objective. There are more millionaires in their 20s right now than ever before. So everyone crying in Gen Z that we don't have opportunities. What about your contemporaries who are crushing it on social? The way I think about business is employees first, customers second, me third. Speaker 4 (1:16) Is Gary Vee happy? Speaker 3 (1:19) I... Speaker 4 (1:21) So why is social media no longer social? I think it's just voyeuristic at this point. Well, Speaker 3 (1:26) it's not social because the term of social meant your social graph. Yeah. Speaker 4 (1:31) Your Speaker 3 (1:31) people would follow you. Speaker 4 (1:33) Okay. It Speaker 3 (1:33) was always voyeuristic. Yeah. Like it was always, it's always been the same. The reason it's interest media now is the algorithms benefit good content, not people with followers. Speaker 4 (1:44) Which should Speaker 3 (1:45) make everyone listening intoxicated. Because now, no more, that's right, no more excuses of like, oh, I missed it, Gary, you've been doing it for just 20 years, I'll never be like you. You sure will. Alex Earl was unknown three years ago. Speaker 4 (1:59) Break this a little down for me. This is my own curiosity. VaynerSports, VaynerMedia, VaynerX, like. Speaker 3 (2:07) VaynerX is a holding company. Holding company, okay. Where VaynerMedia, so VaynerX is marketing. is a production media creative marketing company. Within it is VaynerMedia, The Crown Jewel, two other junior, but soon to be equal VaynerMedia's, Chuck Media, which used to be known as Sasha Group, I rebranded it, so now my whole last name is in there, VaynerChuck, Chuck Media, and Tamara Group, which is named after my mom, and then Gallery. which is a publishing, our purewow.com, Covator, and then the speaking bureau, Vayner Speaker. So that's VaynerX. Speaker 4 (2:44) Outside Speaker 3 (2:44) of VaynerX is VaynerSports because my minority investing partner in VaynerX is Steven Ross, the owner of Dolphins, Speaker 4 (2:52) and Speaker 3 (2:53) he can't own any piece of a sports agency by NFL rules. So AJ and I had to put VaynerSports outside of VaynerX. Then there's VaynerWatt. which is something I've just started talking about, which is a three-year-old TV production company with my partner Eric Wattenberg, so VaynerWatt. So you'll start watching Netflix, Hulu, Amazon shows in the next year or two and in the beginning see that logo, VaynerWatt, so we'll be spending more time in Hollywood. The restaurant group, the wine store, the alternative sports investment. I was on CNBC last week. My wiffle ball. Ownership, we just won a World Series. Pickleball, thank you. Pickleball, Unrivaled, the three-on-three women's basketball league, the sailing league. Speaker 4 (3:39) Like, Speaker 3 (3:39) we're, me and AJ are building a very big portfolio of alternative sports investments. So pretty active in that. My personal brand, you know, the content and all that is an entity in itself. Of Speaker 4 (3:52) course. Do you actually have it, like, as a true entity? Speaker 3 (3:55) No. I have a personal LLC, which it might interact with at times. So Speaker 4 (4:02) quite Speaker 3 (4:03) a Speaker 4 (4:03) bit of stuff, all Speaker 3 (4:04) of which I'm very active in. And so I'm definitely – I go on this rant early on not for bravado but more to – create permission for the entrepreneurs that are listening who want to do more than one business in a world where a lot of the entrepreneurs we look up to tell you to focus on one. I Speaker 4 (4:27) was going to ask, how do you do all that? Because I would sit here. So I run kind of a consulting team for businesses, small businesses. I would tell most people to say, like, if you don't get focused, you're going to screw the pooch here. Speaker 3 (4:42) I think there's a little bit of Bo Jackson, Deion Sanders in me. Speaker 4 (4:46) I Speaker 3 (4:46) just think I'm actually capable of doing more than one thing. Speaker 2 (4:49) Like, Speaker 3 (4:49) just the truth. So there is a level of like, and by the way, on the record, it has nothing to do with me. My mom and dad had sex at the right second and gave me DNA that allowed me to. So I do think that's true. And just like Bo and Deion, like, it's hard to do that. It's rare. So I do think it's rare for someone to be able to meaningfully run. Every business I just mentioned, every one of them does over eight figures in revenue. These are all 10, all of that. And we didn't even get into VFriends. Do Speaker 4 (5:19) you understand what that is? I do, I do, I Speaker 3 (5:21) do. That is wild. But I also don't think it makes me special. What I think is special about what I'm doing and why I'm intoxicated of still doing podcasts like this is I'm not trying to maximize dollars. Speaker 4 (5:36) Explain that. Speaker 3 (5:37) Well, I'm not so sold that all these eight businesses are actually maximizing my financial upside. Speaker 4 (5:43) Okay. Speaker 3 (5:44) I think back to your advice, I think if I want 100, we didn't even mention VFriends, which is getting a ton of my attention. It's my Pokemon Marvel Disney business. I Speaker 4 (5:52) mean, it is so cool. This is for my daughter, by the way. I have a five-year-old. One Speaker 3 (5:56) of my favorite things about VFriends is it's a massive girl dad brand. Two of the five hottest. characters in our universe is fearless fairy and ambitious angel and so anyway i'm i believe if i went a hundred percent of v friends or a hundred percent of vader x or a hundred percent of vayner sports or a hundred percent of vcr group or vayner what or wine library that that there's a chance i would make more money and Speaker 4 (6:22) you don't care not because you don't care about money because you just have more passion and other You would rather do... Speaker 3 (6:28) Yeah, I got D's and F's in school because I... Speaker 3 (6:33) So I've never done anything about money. From 22 to 34, I gave 100 hours a week to my parents. Left with nothing. You know, sometimes people try to razz me in comments with all the content. Speaker 4 (6:45) And Speaker 3 (6:46) they're like, don't listen to him. He inherited his family's wine business. Not only did I not inherit it, I built it. I currently do not own any of it. My father owns all of it. And I gave up my greatest youth years. Speaker 4 (7:01) Yeah. You said you exited at 34, 35. At 34, I Speaker 3 (7:05) left. I definitely didn't exit shit. I left the business and started VaynerMedia and started it in a conference room smaller than this little studio we're in with my brother and three of his friends because I had no money. Speaker 3 (7:20) Right. And so. And Speaker 4 (7:21) so you should go start a business with no money. How Speaker 3 (7:23) old Speaker 4 (7:23) are you? Forty five. Right. Speaker 3 (7:25) Think about thirty four years old, not having a literally not having any money, like did not have enough money to pay a lease for a couple thousand dollars a month. Because what had happened was I did save up a lot of money, even though I was making sixty five, seventy five, eighty thousand a year when I was twenty five, twenty nine, thirty. Sure. Speaker 4 (7:45) I Speaker 3 (7:46) was living a twenty four thousand dollar a year lifestyle. I had a shitty apartment by the liquor store and did nothing. So when you don't do anything and you don't spend any money, you can save. And right before I started VaynerMedia, I had invested all my savings into Facebook and Twitter. Speaker 4 (8:02) You literally went for the moon. Moonshot. I'm going for it. Speaker 3 (8:06) Going for it. By the way, it was $200,000. It wasn't like it was a billion. Speaker 4 (8:11) It's everything you have. But Speaker 3 (8:12) it was everything I had, to your point. And I was 33 and I had resentment built up because I built up a $50 million business for my dad and he wasn't paying me anything. And his answer was, you'll inherit this when I die. And I'm like, dad, we're 22 years apart. You have great genetics. Like, I'm going to be fucking 74 when I inherit this shit. So that's why I had to leave because I wasn't in control. Speaker 4 (8:35) But I was okay with Speaker 3 (8:37) that because I knew what I was doing from 20 to 30. From 22 to 30, I had no problems. From 30 to 33, it was starting to build up of like, fuck, I'm getting fucked here a little bit. You Speaker 4 (8:46) did have a little bit of that. Yeah, Speaker 3 (8:48) I don't. I've Speaker 4 (8:49) studied you as much as anybody. You don't talk about that a lot. No, because I don't Speaker 3 (8:53) want Speaker 4 (8:53) to paint my father in the wrong picture. Of course. Because I don't think Speaker 3 (8:56) it was so Speaker 4 (8:56) much his Speaker 3 (8:57) fault. I think every immigrant that's listening that grew up with a gas station or a deli knows in immigrant families, not American families. The mindset is you give it all to the business and you inherit it when you're old. So I don't think my dad was trying to fuck me, Speaker 2 (9:12) but Speaker 3 (9:12) I definitely started feeling some sort of way. The business was doing 3.8 million when I started running it. Now I'm working 120 hours a week every day. Speaker 4 (9:22) Did you and your dad have this conversation where you said, dad, I'm getting frustrated? Speaker 3 (9:26) Me and my dad fought Speaker 4 (9:27) tirelessly. We Speaker 3 (9:29) had many arguments about not really that part. That started to happen. Speaker 4 (9:35) Later at Speaker 3 (9:36) 30. Speaker 4 (9:36) Okay What Speaker 3 (9:37) we fought about was just like how we treated our employees how to run the business like day-to-day shit But yeah from Speaker 1 (9:42) 30 to 34 Speaker 3 (9:43) there was a four-year build-up of me being like Fuck him and AJ was also coming. My brother's 11 years younger to me. Speaker 4 (9:50) Okay At Speaker 3 (9:51) this point he's 19 when I'm 30 he's going to college and he's like I'm not fucking working for dad Speaker 4 (9:57) I was gonna say were you like bro, you got to get in here. I'm out Speaker 3 (10:00) No, I wasn't mad. It was like I thought when he was 14, bro, get in here. We're going to do this. Speaker 4 (10:04) Oh, OK. Speaker 3 (10:05) Bro was smarter than me. Bro at 15 at 15 was like, bro, I'm never going to fucking work for dad. So I knew in the back of my head for a while, like, oh, shit, if I want to be in business with my brother, it's going to be have to be outside of my library. But anyway, going to the point. I've made no decisions on maximizing finances. And if my financial team was sitting here, they'd be like, yeah, he's an idiot. Like he doesn't maximize against taxes. He doesn't do safe shit like real estate and S &P. Like I'm just living for joy. Speaker 4 (10:34) I'm Speaker 3 (10:35) not scared of going backwards. I'm not scared of the judgment of the entrepreneurial community if I lose it all. Speaker 4 (10:42) No kidding. Speaker 3 (10:43) Real talk, brother. We don't know each other like that. I'm telling you. Look at Train's body language. Like I. Speaker 3 (10:49) All the propaganda I put out every day of not listening to anyone, it's real to me. Like, okay, like what? Like, I'm not living for the cheering in the comments section. I'm wildly humbled by the way you started this podcast. Like, the warmth is like real. Like my goat, are you kidding me? Like, look, I'm literally even getting Speaker 4 (11:09) goosebumps. Speaker 1 (11:10) Like, that's Speaker 3 (11:11) insane. You're my goat, Speaker 4 (11:12) bro. Speaker 3 (11:12) But I'd be okay with disappointing you by like losing everything. Because I'd hope you'd learn from whatever the fuck I did to go to that. By the way. Does that make sense? I view myself as a proxy to the game. Sure. Selflessly to the game that gave me so much more than the selfish things the game can give to me. Speaker 4 (11:31) Yeah. Speaker 3 (11:31) Okay. I'm not in the game of entrepreneurship for a yacht. You know this about me. I've never posted anything bougie. Speaker 4 (11:38) Never. Ever. Like to the point of like. Come on, buy her something nice. Yeah, because Speaker 3 (11:44) for me, nice is I already bought it,