Gary Vaynerchuk is New York Times bestselling author, entrepreneur, investor, and public speaker. He sits down with Chris Van Vliet at West Coast Creative Studio in Hollywood, CA to discuss how wrestling influenced his videos, where his pro wrestling fandom began, why Bret Hart is a better businessman than you, why he believes Macho Man Randy Savage is underrated as a wrestler, wanting to buy the New York Jets, and more!
I’ve always been a fan, but when I found out that you liked wrestling. It was like that scene from Step Brothers. ‘Did we just become best friends?’
“It’s real. Anytime you have a passion. I mean, if I literally see someone wearing a Jets hat or a hoodie, it happened the other day in the city. It’s scary how the instant connection is there, and if I saw someone wearing a 1980s retro Roddy Roddy Piper T-shirt, I would get fired up too. It’s just the way the world works.”
Where does it go back to for you? When did you start to become a wrestling fan?
“I mean, I’m 50, so I was fully caught up. Hogan beating Sheik in Madison Square Garden, that’s a very early memory. WrestleMania 2 was something I was excited for, knew it was coming. Underneath that, it gets a little blurry of where I sat with WrestleMania 1. I was super aware, like the whole Cyndi Lauper MTV interaction, so I would say, anyone of my age, you know, I was an immigrant. Ironically, a very big father figure to me was my dad’s uncle, but the way my dad and grandma, and like the way our family worked, he was only eight years younger than his uncle, and I’m eight years younger than his son. He passed away, but a very big influence in my life was a gentleman by the name of Misha Shiffrin. Because my dad worked all the time, would go to my games and was a very big part of my childhood. He watched wrestling when we first came to America and thought it was real, and thought it was epic. But I don’t really remember that; that was more through the stories he told me, and my mom told me, but I’m definitely an 84-85, in that era. I remember when Macho Man beat Tito Santana for the Intercontinental title, that was massive for me. I remember when he came to the WWF. I will reference it as WWF quite a bit in here, but I’ll try to be politically correct with E.”
Who was your guy growing up?
“Macho Man, I very much like the underdog. Macho Man was huge for me. The way they entered him into the WWF was all the managers wanted him, right? Then he said, ‘My manager is Elizabeth,’ and she comes out. I was getting to the age where I’m like, oh, that’s a pretty girl.”
“I grew up a four sport fan, Rangers, Knicks, Yankees, Jets, and I didn’t win my first championship into 94. I was 18, senior high school, when the Rangers won the cup. The reason I was okay with that was Macho Man winning the tournament for the heavyweight title was the biggest thing of my childhood. That was my first championship, so I was huge Macho Man over everyone, even when he was a bad guy. When he beat Tito Santana for the title, that was massive for me. I was like all proud in school, that was my guy. So it was weird. It was a bad guy when he first came, but there was just his charisma. The way they brought him into the WWF, that was an incredible era of how Mr. Perfect, or Razor Ramon, and obviously before that, Macho Man, and everybody, Billy Jack Haynes. I remember Bad News Brown. What Vince had in that era of introducing someone for weeks before they got into the ring, by the time Macho Man wrestled, the first match I ever saw him wrestle, I was already hook, line, and sinker.”
What do you think it is about pro wrestling that makes people such fanatics of it?
“Oh, it’s storytelling. It’s why people love movies, it’s why people love cartoons, it’s why people love Spider-Man and Superman and Mickey Mouse and The Care Bears. It is the human storytelling. To me, it’s the framework of sports, meaning I think Vince McMahon is much more similar to David Stern and Dana White than people realize. The only difference is, and he’s close to Walt Disney and Jim Henson, like he blended characters and humans in a way that good sports [do]. Steph Curry for my son, he’s a hero, like a little guy, he can do it, Caitlin Clark. Athletes when they’re at the apex, Jordan. They’re superheroes, and wrestlers are superheroes, you know. There’s like maybe the greatest superhero of my life, of my childhood, was Hulk Hogan. He was everyone’s superhero, and so they’re superheroes, their stories, their soap operas, which novels, story arcs are perfect, and you know this, that everybody listening to this podcast, when they’re good, there’s nothing better, and when they’re bad, you’re just waiting for them to get good.”
How much of what you do and the way you speak now is inspired by the wrestling you saw growing up?
“Clearly, you’ve done your homework, because I’ve said this out loud. I really do believe that one of the reasons I popped as a content creator is because early in my career, when I was starting to speak on stages, I was an internet personality. This is very early, I’m talking 2007-2010, they would ask me to cut a promo, like, “Hey, I’m gonna be in Montreal speaking…’ I didn’t even know I was doing it, but every time I would submit them, they’re like, ‘That’s amazing.’ Finally, three years later, might have been Drock, when I first started really filming, he’s like, “You like, he’s like, he would have the embrace, you know, this, we do this now, it’s like, hey, you got to make this thing, you’re gonna be in St. Louis on there, and it would literally be like, this ‘Thursday night at the Civic Center, I’m gonna take you down!’ There was an element of like me doing a promo cut. I know that Macho Man and Richard Pryor are deeply ingrained into how I do public speaking and internet videos, very influential.”
When you were doing a lot of the rant-style videos, those to me felt like a heel promo?
“100%. To me, you don’t even realize it when it’s happening, and then you realize it, and then you’re almost trying to not be a caricature of yourself. But yeah, my early content is incredibly inspired by wrestling content.”
You put out a video titled Why Bret Hart is a better businessman than you. Why is Bret Hart a better businessman than someone?
“If I recall that article, and that moment, the excellence of execution. Execution to me, is everything. So many of you right now that are watching, you’re really creative, you have ideas, and you see other people, ‘Oh I had that idea.’ That’s nice, but you’ve got to actually do it. Everybody watching here, regardless. I know Bret’s popularity, or people’s point of view on Bret these days is kind of a little more mixed, but I’m a huge fan. My sister was a huge fan of Bret Hart. She thought he was super cute in those days. We watched a lot of wrestling. He was unbelievable in the ring. We all know that. There’s no one, no matter if you like Bret or the sh*t he talks about these days, everyone knows exactly what kind of wrestler he was, and I think that’s business too. For what you do for a living, you know wrestling, a lot of people know wrestling, you have the gift of gab, a lot of people have gift of gab. Being disciplined, Tuesday, Thursday, Friday with [Ask CVV], the team set up. It’s all f*cking execution. So I wanted to write that article because I’m always looking for ways to integrate wrestling if I can, and I do think people underestimate that execution is the punchline. All the best ideas in the world have never been executed because the human that came up with it was unable to execute it.”
When we’re talking about execution, what do you think it is that keeps people from doing it? Is it they’re comfortable where they are? Is it fear of the unknown?
“We could sit here for an hour and bring up the other ones. There’s so much to it. The people fear judgment, so it’s easier to stand on the sidelines and say everyone sucks then going on the field and sucking, and having people tell you you suck. There’s their childhood. They just, you know, sometimes people are trained their whole life to be comfortable, and like it’s hard to get uncomfortable, right? Self-awareness. I wish I was a wrestler, but some people don’t have the skill sets, you don’t have the athletic ability or the mobility. There’s just a million things that go into it. I think a lot of it is grounded in insecurity. I think a lot of it’s grounded in a poor perspective. I think a lot of stuff I talk about, whether it’s patience or accountability, is grounded in these things that I think about, but there’s a million different reasons why someone doesn’t get in, but most of them are grounded in excuses, you know, podcasting, you put in the work, there’s a lot of people watching this show right now that actually know more about wrestling than you do.”
You just turned 50 last year. How did that milestone change you, if at all?
“Didn’t change me at all. Meant absolutely nothing. I’d love to make up something for you and your viewers. It was a complete non-event emotionally. I can’t even come up with something small. I don’t love my birthday. It’s really weird. It’s actually the thing that I have not figured out about myself in a world where I love being known and love to be about my stuff and me and this stuff. I get very weird about my birthday. I can’t wait for it to be over. I used to think it was because I was getting older, because I love life so much, and this and that. There’s something that feels very unearned about the attention of your birthday, that is the latest theory I have, which is I don’t feel like I earned anything, so why are we like doing anything about it. I don’t know what it is. It’s always. It’s been going on now for 15 years or so. No, I live my life every day with gratitude, brother.”
I feel like me and you together here is throwing a lot of positivity out there, but I’ve heard you talk about it as practical positivity, and I love that it’s not just positivity for the sake of positivity, toxic positivity.
“You know the toxic avenger? That real f*cking weird guy with the green face and his eyes up here. I’m like, I’ll look like that if that’s who I am. I’m all about toxic positivity. I mean, it is such a ludicrous [thing]. Anyone who weaponizes that word is called toxically cynical. Why can you be toxic positivity, but when you’re a cynical dark person, you’re keeping it real? Yeah, I don’t buy it. I’m fine with it. Throw it at me. The world is dramatically better when you’re optimistic and positive.”
You went all in on social media and YouTube way before anybody saw it really happening. What made you make that decision?
“Back to extreme empathy. I have a very good read on what people are gonna do before they know it. That’s what I’m good at. It’s because I put in the work to pay attention, and it comes natural to me. Some people can sing, some people can throw a baseball, some people can cook. I can understand consumer trends, and then I put in work. It’s not like I just sit there and like I do the reading, I do the research, I pay attention, and it was very obvious to me that YouTube was gonna hit. I just kind of knew, like it wasn’t complicated, even though there was no video platform on the internet. People watched unlimited television. I was like, what’s the f*cking difference? It’s just video. So I’m very good at understanding things that are historically true. Substack, Hannah’s here in the background, like she was early on. People always ask me, Gary, why do you write books? You’re such a digital guy, I’m like, because people read them.”
What’s been your best investment ever?
“Facebook.”
How early were you in on Facebook?
“Early, I mean, probably two years before [it got big]. I mean, not in the angel round, but I invested in oh seven. It was years before it went public. I haven’t sold a share, still to this day.”
Do you still have aspirations to buy the Jets one day?
“Forever, I mean, it’s been there forever.”
Is that just the pie-in-the-sky goal that seems unachievable, so you’ll just keep shooting at it?
“Later in my life, you know, at the time when I started thinking about it, when I was a young kid, it was silly. I don’t even know where it really came from. I don’t know how I thought it. Then my 20s and 30s, owning a sports team wasn’t what it is today, like the numbers were still achievable-ish. In the last 15 years, 10 years. It’s really changed. It’s become like the most sought after thing.”
Does the owner of the Jets know that you want to buy the Jets?
“Yeah.”
Have you guys talked?
“No, because I’m not in a position to buy it, and I think I wouldn’t embarrass myself to have that conversation. I’ll have it when I really can do it, and the Johnson family has no interest in selling, it seems, which is good for me, because I need way more time to amass the wealth to get there. So that’s where we’re at.”
We’ve talked about a few of your videos that went viral, you’ve had many of them. Do you think that one piece of content has the ability to change someone’s life slash career?
“Of course, that’s what the whole world’s about. You know, there’s seven of us in this room, and there’ll be millions that watch us over the next 50 years. Every one of us have been affected by someone else’s words. “
I’ve heard you say that one sentence from a podcast can change somebody’s life.
“I’m literally looking at the five people behind the camera now, whether it was your grandfather, grandmother, father, mother, brother, sister, best friend, or someone you admire. Every one of you right now, everyone who’s watching can recall something right now that was said that had an impact on them. What did Gandhi or Martin Luther King, what did these people do? It was words, brother, f*cking words matter because you change someone’s perspective. Whether pro or con.”
Who is on your wrestling Mount Rushmore?
“I think the Mount Rushmore of wrestling is Ric Flair, Hulk Hogan, Andre the Giant, and I gotta give one to the Attitude Era. Believe it or not, I’m gonna go with The Undertaker. I know Rock and Austin and Bret Hart and Michaels… But I think I don’t think people understand. Andre the Giant carried wrestling through the 70s. Remember it was regional, and when he would go. I just think he’s just all time. I’m devastated when I watch a lot of clips where people do their Mount Rushmore. Andre should be in every one, and Hogan changed everything.”
Who do you think is an underrated wrestler?
“Macho Man Randy Savage. I’ll tell you why, because as a wrestler, I will say right now that if you do not think that Ricky “The Dragon” Steamboat Macho Man Randy Savage, WrestleMania III is not a top 2,3,4, match of all time, I have bad news for you, and this is just with love, you do not know what the f*ck wrestling is about. I really believe it.”
What is Gary Vee grateful for?
“The health of my family.”
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