Insight with Chris Van Vliet - Gary Vaynerchuk Is A Huge WWE Fan! Macho Man, Jake "The Snake", Bret Hart, Wrestling Collectibles

Episode Date: June 2, 2026

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! Please support our sponsors: HELIX SLEEP: Flash sale! Go to https://helixsleep.com/cvv for 27% off sitewide! COZY EARTH: Go to https://cozyearth.com/CVV for up to 20% off! BEAM: Go to https://shopbeam.com/INSIGHT and use code INSIGHT for up to 40% off Beam’s Dream Powder DELETEME: Use the code INSIGHT to get 20% off your DeleteMe plan at https://joindeleteme.com/INSIGHT FACTOR: Get 50% off your first box, plus Free Breakfast for 1 Year with the code INSIGHT50OFF at https://factormeals.com/INSIGHT50OFF PURE PLANK: The future of core fitness! Use the code CVV to save 10% on Pure Plank designed by Adam Copeland & Christian: https://gopureplank.com/cvv SEAT GEEK: Use my code for 10% off your next SeatGeek order*: https://seatgeek.onelink.me/RrnK/CVV Sponsored by SeatGeek. *Restrictions apply. Max $20 discount NORDVPN: Exclusive deal! https://nordvpn.com/cvv Try it risk-free now with a 30-day money-back guarantee! PRIZEPICKS: Download the PrizePicks app today and use code INSIGHT to get $50 bonus credit in lineups after you play your first $5 lineup! For more information about Chris and INSIGHT go to: https://chrisvanvliet.com If you have ever enjoyed any of these episodes, could I ask you to please consider leaving a short review on Apple Podcast or Spotify? It takes less than a minute and makes a huge difference in helping to spread the word about the show and also to convince some hard-to-get guests. Follow CVV on social media: Instagram: instagram.com/ChrisVanVliet Twitter: twitter.com/ChrisVanVliet Facebook: facebook.com/ChrisVanVliet YouTube: youtube.com/ChrisVanVliet TikTok: tiktok.com/@Chris.VanVliet Learn more about your ad choices. Visit podcastchoices.com/adchoices

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free of charge. BetMGEMGEMP operates pursuant to an operating agreement with Eye Gaming Ontario. Thank you so much for coming in. Thanks for having me. I've always been a fan, but when I found out that you liked wrestling, it was like that scene from stepbrothers. Did we just become best friends? Yep.

It's real. Anytime you have like a passion. I mean, if I literally see someone wearing a Jets hat or like hoodie, it happened the other day in the city, it's scary how the instant connection is. And if I saw someone wearing a 1980s retro Roddy Rowdy Piper t-shirt, I would get fired up too. It's just the way the world works. I saw a guy wearing a rock shirt recently and I said, where'd you get this? shirt from. It doesn't matter where you got that shirt from. Did he do that? No, I did it to him and he's like,

ah, you got me, you got me. Where does it go back to for you? When did you start to become a wrestling fan? I'm actually trying to think about it. I mean, I'm 50, so I was fully caught up like, you know, Hogan beating Sheik and Madison Square Garden. That's a very early memory. I was, 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 Sydney Lopper MTV interaction. So I would say, you know, anyone of my age, you know, I was an immigrant. I was, you know, ironically, a very big father figure to me was my dad's uncle, but the way my dad and grandma, like, the way our family worked, he was, he was only eight years younger than his

uncle, and I'm eight years younger than, uh, than his son. He passed away, but a very very, big influence in my life was a gentleman by the name of Misha Schifrin, who like, 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 like 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, everyone. Fair enough. Quite a bit in here, but I'll try to be politically correct with E. But yeah, it was really 84, 85, you know, I don't really remember 83. Like, I watched old stuff, old VHS tapes later,

but wrestling first hit when I was nine or ten. Who was your guy growing up? Macho man. I was very, I very much like the underdust. macho man was huge for me. The way they entered him into the WWF was like all the managers wanted him, right? And then he said,

and my manager's Elizabeth, and she comes out and like I was getting the age where I'm like, oh, that's a pretty girl. I love her. Everyone can do a macho man. Yeah, everyone can do a macho man. And so macho man was my guy. When, like, I grew up by four sport fan,

Rangers, Knicks, Yankees, Jets. And I didn't win my first championship into 94 when I was 18, senior high school when the Rangers won the cup. And 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, you know, the way they brought him into the WWF, that was an incredible era of how Mr. Perfect or Razoramon and obviously before that macho man and everybody, Billy Jack Hayes, I remember Bad News Brown, like 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 hookline and sinker. It was the beauty of the vignettes back then. Yeah. Like, I'm sure you remember the Mr. Perfect vignettes. Well, that's why I referenced it, right? Like that, there's nothing like that. That was the apex, but Razor Moon was big too.

I was like, who's this guy, you know? But Macho Man was kind of, it was, you know, the whole, like, you know, I'll never forget that interview you did with, by the pool side with Meenji. And he's like, there's a plane going plane. I'm not on it, Meenji. Like, it was just a different, he was a superhero to me. And obviously that was pre-internet, 36 channels if you were bougie and had cable. And I watched a lot of, like, those late.

night show. I don't remember if it was on TNT or USA, Vince McMahon interviewing. Yeah. I remember Wachar Man's interview there. So I was a huge Macho man guy. And I never, ever, ever had another one that was close. I was very into Y2J. I was into Jericho. Um, that probably would be the closest in that attitude era kind of, but he was like a two to Macho Man's 10. Machu Man, was my number one guy forever. And then Jericho's still doing it. I know. It's crazy. Still doing it. He's amazing. This spring, denim gets a softer, lighter update. Introducing Old Navy's drapey denim wide leg, a new fit that moves with you.

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You know, 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, you know. And 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, you know, Steph Curry for my son, he's a hero, like a little guy he can do it. Caitlin Clark,

there's, you know, like athletes when they're at the apex, Jordan, we were talking about your Jordan's on the way here. You said you'll never wear Jordans. I never have. Because I'm a Knicks fan. Um, 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, um, they're superheroes, their stories, they're, they're, they're soap operas, which, novellos, they're like, they're like story arcs are perfect. And you know this and everybody listening to this podcast. When they're good, there's nothing better. Yes. And when they're bad, you're just.

just waiting for them to get good. Yeah. Right? That's why there's been different eras of wrestling. I feel like I was so inspired growing up, like in those formidable years, especially in high school, by like the promos I saw, the characters I saw on TV. Like I was coming into being a teenager during the attitude era. Yeah.

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, like, when I, early in my career, when I was starting to speak on stages, you know, I was an internet personality. So, like, this is very early. I'm talking 2007, 8, 9, 10.

And they would ask me to cut a promo. Like, you know, they'd be like, hey, I'm going to be in Montreal speaking. And like, as, like, I didn't even know I was doing it. But every time I would submit them, they're like, that's amazing, this and that. And then finally, like, three years later, it might have been DRock when I first started really filming.

He's like, you could, like, He would have the bull embrace. You know this. We do this now. It's like, hey, you got to make this thing. You're going to be in St. Louis. And it would literally be like, this Thursday night at the Civic Center. I'm going to 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 and very influential. I think any great speaker is like taking people on this journey, right? It's the lows of the lows. the highs at the highs when you get excited. That's a wrestling promo. I'm very affected by wrestling promos.

I mean, I, you know, I, it was, it might have been, I might have liked the promos more than the matches. It was so big. When you were doing a lot of the rant style videos, those to me felt like a heel promo. A hundred percent. Yeah. Yeah.

And to me, like, you don't even realize it when it's happening. And then you realize it. And then you're like, then you're almost trying. and not be a character ship yourself. But yeah, those are, my early content is incredibly inspired by wrestling content. You put out a video titled, Why Brett Hart is a better businessman than you?

Yes. Why is Brett Hart a better businessman than someone? You know, if I recall that article in that moment, you know, the excellence of execution. Execution to me is everything. You know, so many of you right now that are watching, you're really creative, you have ideas. You know, like,

and you see other people like, oh, I had that idea. Like, that's nice, but, like, you've got to actually do it. And, you know, everybody watching here, regardless, you know, I know Brett's popularity or, like, people's point of view on Brett, you know, these days is kind of like a little more mixed, but I'm a huge fan. My sister was a huge fan of Brett Hart. She thought it was super cute in those days.

We watched a lot of wrestling. My sister's behind the camera, everyone. And, and, and, and he was unbelievable. in the ring. We all know that. There's no one, no matter if you like bread or the shit he talks about these days, everyone knows exactly what kind of wrestler he was. And I think that's business too. Like, for what you do for a living, you know wrestling. A lot of people know wrestling. You have gift of gab. A lot of people have gift of gab. Being disciplined, Tuesday, Thursday, Friday the ask, team set up. Like, it's all fucking execution. And 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's the punchline. The best ideas in the world have never been executed because the human that came up with it was unable to execute it. So two things on that. One, you can go back and watch any Brett Hart match versus anybody. And you're like, damn, that's a great match that holds up to this day. They put everyone on.

So good. He was during the time when he was in the 80s when he was tag. team champion, a lot of the untelibized shows like they would use Brett. If Vince thought he had something visually, like all the wrestlers we make fun of because they weren't great wrestlers.

Ultimate Warrior. Hogan. Like, you know, the early kids that Vince tried to put on in the 80s, how shows untelevised, he would use Brett. You know how good of a wrestler you have to be to make someone else that doesn't know how to look

know how to wrestle look good in front of everyone. That is an incredible skill. He's in a Mount Rushmore, in my opinion, just on that, if you care about not your emotions, but like the craft. And I feel that way about entrepreneurship. A lot of people have a lot of opinions about entrepreneurship. A lot of people think they can do it, which I think is great.

Everyone should try, in my opinion, to see if you are or you aren't. But when you get in the depths of entrepreneurship, the reason I root for a lot of entrepreneurs in a world where I think a lot of people have envy, and jealousy is I know how hard it is. And I know that like this concept of deploying luck, like, oh, they got lucky.

You might get serendipitous. Timing might be on your side. But when people use lucky, that means they're weaponizing and trying to take things away from you. You know, back to wrestling, Terry Taylor could have picked Mr. Perfect. He had first choice.

He chose Red Rooster. What a reference. You're like, listen, I'm going to impress your craft. Friends, I don't know what you think about me, whether you like me, don't like me, but one thing you're going to leave this podcast with is like, oh, fuck, Gary knows way more about wrestling than I thought he did. Terry Taylor had first pick.

He decided to be Red Rooster. If he picks Mr. Perfect, maybe we talk about him today different. We all know Terry Taylor was a great wrestler. Is that luck? Is that intuition? That's just serendipity. It's how life works out. But I hate when people weaponize luck to make themselves feel better and try to shit on someone

who's put in a lot of work, which I admire. And so that's how I feel about Brett. Obviously, Brett had the luxury of growing up in a family that was very deep in wrestling culture. And so at a young age, you know, while Hogan was playing music in his teenage years, Brett was spending his thousandth hour in the ring. Of course, he's going to be a better wrestler.

I don't know. I think about those things a lot, and execution matters to me. So the second point on that, when we're talking about execution, what do you think it is that keeps people from doing? 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 than going on the field and sucking and having people tell you you suck. The man in the arena. There's their childhood.

They just, you know, like sometimes people are trained their whole life to be comfortable and like it's hard to get uncomfortable. right? Self-awareness. Some people, like, look, I, you know, I really wish I was a professional. I wish I was a wrestler. Like, you know, like, but like some people don't have the skill sets. You don't have the athletic ability or the mobility or like, you know, like 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, like, there's a lot of people watching this show right now that actually know more about wrestling than you do. It exists. For sure. But you've put in the work, and like, so there's the outcome, you know,

and you've put in the work to educate. I'm sure when you really got even more serious, you became more educated about wrestling. At night, you recently, research things. Like, I just think a lot of people also don't want it. You know, like, and I actually am going to throw you a curveball right now. I don't think people should be judged based on their ambition.

I think people should be judged on the authenticity, meaning if you just want simplicity, if you don't want it, if you think a better life is simple, which, first of all, you're going to find someone who is ambitious agreeing with you. I think more people should live more simple lives. I think a lot of people put themselves in a rat race that they shouldn't be a part of and they're trying to go up to social norms. I always think about the stay-at-home father.

I just wonder how many people in their soul, right, this second, want to be a stay-at-home father, but they don't think they can because we as society look down on that. Or someone who wants to live in a really, really, really rural town and have a low-cost life and enjoy their 5 p.m. to 9 p.m. They want to literally play softball after work. Go to the bar, softball, and then watch wrestling and shoot the shit with their buddies.

And that's, like, good. And I think that those people should feel more comfortable in their skin. I don't know. I just think self-awareness, I think a lot of people don't go in because they don't want to go in because they can't deal with the heat or they don't want to deal with the heat because the heat's not worth it. And I respect all of that, but that's the answer. I think there's a lot of people that try it.

They make a video or they make a podcast or they post a video on YouTube and it gets seven views. And then the next video gets eight. And then the next video after that gets four and they go, well, this isn't for me. Well, a lot of people want to roll in the mud of like I tried, but I couldn't. And they want your sympathy. They're addicted to sympathy. A lot of people live their lives to, paint a picture that they tried, but the system's fucked.

So see and like take care of me financially, emotionally. And you know, that's a, that's a really tough place to be. And I'm empathetic to that, but yeah, a lot of people are not willing to put in the work. I don't understand how people think, you know, it could be so easy. You know, I always use, you're in good shape. Like, I look at a lot of people, you know, a lot of people, you know, a lot of, of real estate agents and physical and, personal trainers.

Thank you. And personal trainers were two of the groups that first started popping up when I was making my content in 2006, 7,89. They were quick to jump in. And I was always fascinated by the personal trainers because they would email me and be like, eh, like, I made four videos and nothing happened.

I was like, Dick, aren't you making content that says if you do four pushups, you're not going to get fucking muscles? Like, if anyone should understand, that this is fucking work and what is required, it's you. You're out there, you know, but then, like, you know,

people are disciplined in some arenas and not in others, and we're all like that, and I'm not disciplined with what I eat, and I'm incredibly disciplined in how I work, and so everyone's different. But I remember you made a shift where, like,

your appearance and, like, working out and eating better, like, it was a shift for it. It was a huge shift. I, like, I was, I mean, I, this one's, something I remember vividly. I was flying back from Houston after a speech. I was 38 and a half. I always liked to say half because I'm like six.

Six and a half. I was 38 and a half. I had my head on the pillow. My back has always been bothering me this then. I was like, I had plenty of fat in my, and I was just like, this can't be good. Like, this is not going to work out. And I decided I wanted to get healthier.

And I decided, before our plane took off, I decided at 40, I'm going to get serious. I think I had a breakthrough. I was like, you know what, if I hire someone full time, and I was at a point in my life where I could afford that now, I'm like, I think that might work. I feel like I'm very accountable to others, not to myself. And I won't want to let my trainer down.

And I was right, that was the insight, the breakthrough. And then halfway through the flight, I'm like, why am I waiting to 40? I'll start at 39. It was like, you know, May, June, it was around this time. I was like, my birthday's November. I'm like, I'm going to start.

And by the time I landed, I was like, that's stupid. I'll start now, and I called Mike Vacanti, who is currently my trainer, who I had like 35 sessions with. He was the last person I tried to work out with. We had like 35 book sessions that I paid for, and I showed up to like three. And I called him and said, hey, and he was busy and I knew he was doing well. So I didn't think of it was him. I was like, hey, do you know a kid like you that can like get rid of all their clients, travel with me and like work for me just on me? And he's like, what about me? And I'm like, you will? He's like, yeah. We met and he was my trainer for three years, transformed my life. Then Jordan Sye came in, worked with me for two, three years, and then Mike came back.

And so like, for the last 12 years, I've had the same two trainers full time. And it's transformed my life and fixed my so many things, my QL issues, my, you know, soft tissue. And I have so much more strength. And I'm really grateful that I, and by the way, going through that, addressing something that doesn't come natural to me. Like yesterday, when I was in Springfield, Massachusetts for my son's basketball tournament, waking up early to go in the gym,

like, I'd rather somebody come and rake my eyes out. That's how much I didn't want to do it. But the fact that I've gotten into a place of my life where I, like, fought through and was disciplined enough to do the right thing, that's what makes me think people can do anything. Because there are very few things that I thought I would be able to accomplish in my life

that didn't come natural to me, at the bottom of that list would have been working out every day, but I've done it, and it makes me feel that other people can break through their hardest challenge to do. You just turned 50 last year. Yes. How did that milestone change you, if at all? Didn't change me at all.

It meant absolutely nothing. I love that. Yeah, I'd love to make up something for you and your viewers. It, like, was a complete non-event emotionally. Yeah, I don't really, you know, I can't even come up with something small. yeah it was do you live your life in that way where like every day is another day or like every birthday's just you know it's another year i don't love my birthday it's really weird it's it's actually the thing that i have not figured out about myself in a world where i like love being known and love to be about my stuff and me and this stuff i get very weird about my birthday i like can't wait for it to be over like um and 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 like, I don't feel like I earned anything,

so why are we like doing anything about it? I don't know, 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. Me too. Like, real talk. I love life.

Like, I really worry about myself in my older age. Like, I am concerned, I think about it quite a bit in the scheme of things of like, am I just so happy because I have so much life in front of me? And like when I'm 90, will I be like, fuck? Like, will I get sad? Like, I don't know. I hope not.

And I maybe I'm talking it out to prepare myself. But like, I love life so much that, you know, whether it's my birthday or not my birthday, it's like a great day and I'm grateful for it. And, you know, I'm pretty joyful. Do you have a number in mind that you want to hope that you get to? Age? Yeah.

100. That's it? I'd like more because I know modern medicine and all that, but like, if you put a contract down that I can get it, if I sign it, I would sign it. But I do think by the time I'm 150 years that everyone who's listening has no idea how good of life quality people that can afford it, which I'll be one of, 100 can be. It's one of the reasons I started working out. One of the most interesting data points to me is life expectancy based on how strong

your legs are and your glutes and everything because so many people fall in their 70s, 80s, and 90s. And so, like, I mean, no one wants to do a leg day less than me. And by the way, I'm so grateful that both my trainers kept me on the leg day thing the whole time because, like,

you're pretty bulky. Like, do you have shitty legs or are you doing too? No, they're not. All right. Like, the weirdest guy in the gym is the guy who's, like, super top heavy with, like, no legs. Chicken legs, yeah.

Yeah. But, um, uh, I would take 100. I expect like 80 to 90 to be high quality. Obviously, you have no control over like diseases and different things that nature. But like, especially with AI now, like, we're really starting to figure out how to like attack a lot of things. And I'm incredibly optimistic. And I am curious with all the advancements.

Like, am I part of the last generation that doesn't live to 150 or 200? Because we're getting close, which is, I'm going to be really pissed. I'm going to be super pissed if I'm like 94 and it's like breaking news. Everyone can live to 200 if you're under 70. I've actually been thinking about writing a movie about this. This is real, by the way. I've been thinking about this movie plot

where the world announces that if you're under a certain age, you can live forever. And the story is basically about the people that are older than that number, revolting. And like this really cool movie, but I'll work on it later. Well, they say motion is lotion. And it's like you move and you're always like, you're moving your mind, you're always doing things, right?

I feel like you'll be completely fine. Yeah, and then I'm also fine with knowing that, like, you can't control it, right? So many people are like, oh, I got to do this and this and this. And they think that's going to, and then like we know of unlimited people who've done everything, right? And unfortunately, the way their cells were structured, XYC happens, and it's unfortunate. I'm at peace with anything, but I have incredible hope and optimism to enjoy it because, man, I think life is really, really good. and I'm very aware that many don't,

but I don't do the things that those people do, which is they get caught up in listening to people that peddle negativity and hate. There's two words that always, you always come back to. Gratitude's a huge one. That's a massive one for me as well. Empathy is another one.

Which one of those do you think is your superpower? I think empathy more. Gratitude keeps me happy, but if you ask superpower, when you walk into any room and you can feel what other people are feeling, and I mean all of them. And then it almost becomes like,

you know what they're actually thinking? Like, do you know the reason I believe in, like, psychics and other random shit is because I know I have something. You know, like, when you have extreme emotional intelligence, I don't think, like, I'm the greatest person gifted with the most weird traits. But I can tell you right now,

in fact, I hate doing podcasts because I always interrupt people. And it's just because I really know what someone's going to say. Like, it's this weird thing. And so I would say empathy because I do think, it's a very special gift.

And empathy is different than compassion and sympathy. Some people are incredibly compassionate. You know, they feel compassion for someone else. They feel for you. They're like, oh, I'm so sad that happened to you,

but they can't feel you. When you can feel you become a good showman, you become a good salesman. Of course I'm good at sales. I know what to say to sell you. And I mean if you just walked up right now and looked at my baseball cards

at 15 years old, within a second or two, I know what to say to you. Where's that come from? Fuck me. You know? I have no idea. Wow.

But it is really special. It's also, you know, it's funny. In my older age, it made me feel even better about myself because I was like at some point probably my 30s or maybe 40s, but I think 30s. I was like, wait a minute. I'm such a good person. I have this gift that could fucking be really bad. I could like really do bad shit.

I could like trick all of you into doing bad. Like I could really build a fucked up cult and make everyone drink bad. Kool-Aid. And so, you know, I'm very grateful that I have it, and I'm grateful that I was gifted good intent, and I feel like I know what to do with it, and that's my day to day to day. 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, right? Oh, my God. It's so mad when people get, like, triggered by my positive. Toxic positivity. I've heard it thrown around. I'm like, fine. Yes. Give it to me.

I'm the toxic. You know the toxic avenger, that real fucking 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. Like, I'm all about toxic positivity.

I mean, it is such a ludicrous. Anyone who weaponizes that word is called toxicly cynical. Like, why can you be toxic positivity? But when you're cynical, dark person, you're keeping it real. Yeah, I don't buy it. I'm fine with it.

Throw it at me. Like, I don't even know. The world is dramatically better when you're optimistic and positive. But you're practical about it. And I think that that's what makes it work. Yes, I don't think, like, hey, everyone, just sit on your fucking ass and cross your fingers and, like, just hope for millions of dollars and it will drop it. Like, of course you have to be practical. There's nothing happens without action.

But, yeah, you know, I choose to be practically optimistic about everything. I believe in it. And it's not a focus group of one. I, for a living, watch the world. And I can tell you it's not super complicated. That like the people that go through that lens, I always say this, in life you find what you're looking for. If I decided to look for negativity,

I can sit here right now and rattle off unlimited things. You know why? Because there's unlimited news and social media content about everything to get negative in the world. My question is, are you looking for positivity? Yeah. You know, like, if you're choosing to watch podcasts around extreme politics to the left and right, I have good news for you.

You're going to be scared and unhappy. If you watch something that talks about the missing link and Bad News Brown, you know, and the Rock and Roll Express, like, you'll smile and think back to your nostalgia and you'll be in a good mood. This is that Tony Robbins thing he talks about where it's like, look around the room. Tell me all the green things that you see, right? Look at all the green things. Close your eyes. Now tell me all the blue things you saw.

Yeah, of course. Life is what you're looking for. Yeah. And like if you're looking for negativity that was in your DNA, that was in your parenting, that was in your circumstances, that was in the luck of the draw, but you're able to get out of it. And I think once you become accountable and realize you're capable, like I always ask this, I'm like, at what age are you now a grown-up? Like, at what age is it no longer everyone else's fault? Is it 18? Is it 22?

Is it 25? Is it 30? is it 35, is it four, like at what age? Because it's got to be some age, I think. What's funny because, yeah, just you legally become an adult at 18, but you're like, I haven't figured anything out. Yeah, I mean, like at 18,

you could literally go to a foreign country and fight a war, but like we have unlimited 35-year-olds running around spending 100% of their time prying about mommy and daddy, you know? And I get it. And like some people have some incredibly challenging circumstances. The problem is, like, everyone else has problems too.

And so, like, you know, what are you trying to do? Like, too many people want to just lay in their mud. They want to re-up their mud. They want to re-up their mud. You know, and I get it because people were hurt and they didn't have the emotional strength. It's just like, you know, I was not raised, nor did I have the DNA to go to the gym.

and I really, really worked at it mentally for eight years before it finally tipped and it became a habit. And that's a lightweight, not important thing. But for many people, I would say this. If anyone in the world figured out your circumstance, then you can to. If anyone with a drug infested father and a mom that ran away on the second day got to a place where they worked through it and got to a productive, solid place, well, you can too in that extremely challenging circumstance.

And I don't know why someone wouldn't choose hope. I don't understand why. Let me just stay in this dark place in perpetuity. And I know why, because it's hard. It's fucking hard. But like everything good is hard. Yeah. Everything good is hard.

Yeah. You went all in on social media and YouTube way before anybody saw it really happening. What made you make that decision? I'm, you know, back to extreme empathy. have a very good read on what people are going to do before they know it. It's what I'm good at. Yeah, you're really good at reading trends. It's because I put in the work to pay attention and it comes natural to me.

You know, some people can sing. Some people can throw a baseball. Some people can cook. Like, I can understand consumer trends and then I put in work. Like, it's not like, again, 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 going to have.

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 fucking difference? It's just video. And so I'm very good at understanding things that are historically true. That substack, Hannah's here in the background, like, she was early on it. Like, of course, it was like, people read the, people always ask me, Gary, why do you write books? You're such a digital guy.

I'm like, because people read them. Is it interesting that you write books, but don't read books? Yeah, I mean, you know, there's some of the best head coaches of all time didn't play the sport. Like, I don't think I need to read books to be able to write books that are commercially successful. But I'm saying the inverse of that, it's amazing that you've written so many books that have inspired so many people. And you're like, I'm just not really a reader. Well, because I don't have reading comprehension. Like when you completely waste your time reading anything, I mean, Hanako from the Befriend's team just texted me something.

It was three sentences. I was walking with my sister just now, and I was like, I don't understand. I called her. And I was laughing because I thought about it while I was calling him. Like 99.9% of people would understand this and what's like. And in fact, it saves, reading saves people a lot of time. You know, I have to call a lot of five-minute meetings because I don't understand what you wrote in this paragraph. You know, like, it's just not how my brain works and I'm comfortable with that.

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That was easy. I started my YouTube channel, my first YouTube channel in 2007. Because I was working on TV. I was interviewing some of the biggest stars on the planet. And I'm like, man, unless you're watching TV in this city on this day, at this exact time, you're never going to see my interview with whoever it is. So I'm behind my boss's back. I created a YouTube channel under some other like name.

And I started posting my interviews on there because I'm like, if you're a fan of this celebrity, this actor, this band, you're going to want to find out about all these things they said in this interview. Sure. And that was early, early in the days of YouTube. YouTube was obvious to me. It took off so quickly. I remember when it sold $1.7 billion.

And people were like, that's way too much money. That's crazy. For everybody who's listening, now everyone's a billionaire. That was like me saying that something just sold for $78 trillion. It was such a big number. And really, that sale changed my career because I read all about it. In one of the articles that said angel investor, Ron Conway, was set to make X, Y, Z amount of money. I had never heard that term.

I googled what an angel investor was and decided that day in the liquor store that I was going to become an angel investor. and within a year, I invested in Facebook, Twitter, and Tumblr. Wow. So the YouTube sale to, was, YouTube was massive in my career. Not only did it change the course of my life with Wine Library TV, but its sale to Google. And the articles written about it were the inspiration to why I wanted to become an investor. And I think the stat now is like, whatever it's sold for it, they now make in like four days or something. Oh, yeah.

It's like, it's one of the great acquisitions of all time. What's been your best investment ever? Facebook. Like how early were you in on Facebook? Early. I mean, probably two years before it's, I mean, not in the angel round, but I invested in 2007. It was years before it went public.

Wow. And I never sold a share. Still to this day? Still to this day. Wow. I promised myself when I invested in it that I would hold on to it until Mark was no longer there. Because I just knew he would, the thing I knew about Mark early on was a skill that I have, which

is he would adapt to the consumer behavior. And he's absolutely proven that to be true. And that was a very good hypothesis of mine. A lot of my friends who were early at Facebook, it opened at $42 a share. When you work at a company, everybody, pre-IPO, you can't sell your stock for the first six months usually. The six-month mark of Facebook,

the stock went down from $42 to $19. Many of my friends sold at $19 because they were all in their 20s and 30s and they had a lot more than I had. They were employees. even though I invested. But I mean, it's $600 a share now. It's 30x.

And when you sold, you know, $50 million worth of stock, you know, and it changed your life as a 30 year old. That was amazing. Yeah. Except now it's, you know,

15 years later. And you're like, wait, that's $1.5 billion. It starts to get really scary when you think about it. You said you were a fan of four New York teams growing up,

Jets, Rangers, Yankees, and Nicks. Yes. And I heard you say that you stopped being a Rangers fan after they won the cup in 1994. That's correct. And then you stopped being a Yankees fan in 96

after they won the World Series. That is also true. I know you were a hardcore Jets fan. Yes. If the Jets somehow get good, will you stop being a Jets fan if they win the Super Bowl? Well, before we go to the Jets,

the second we're filming this is the Monday after the NICs have found out they're playing Cleveland. So the NICs are about to play Cleveland in the Eastern Conference finals. There's a really nice chance that the NICS will win this series. Did you see Danhausen curse them, then uncursed them?

This is a big reason why the Knicks are winning. Yes, I did see that. Stanhausen. You know, and I do think the Spurs are the only team that can beat the... I currently sit and think the Thunder would be too tough of a matchup for the Knicks and the finals. But I think the Spurs match up well with them, and I think Knicks match up well with the Spurs. Plus, game three of the NBA Finals, for some unknown reason, I am going to San Antonio for a public speech, and it's the first time I'll ever be in San Antonio, which is a...

interesting, which now I've decided, and by the way, that's game three of the NBA finals, which means the Spurs would be playing the Knicks in New York, and I'd be missing the game. I've now decided that's a sign and that the Spurs are going to stun the thunder, and the Knicks are going to make it. So, the

Jets are on a planet by themselves. Okay. Because they're a different thing for me. The answer is, I don't know, and because football's on Sundays and only 17 games, probably soon to be 18, my intuition, if I'm answering honestly, is that I would continue to root for them and be in it

with a very different energy. Look, I'm a Browns fan. Yes, hard. So, yes, just as hard as being a Jets fan. The Nix is the interesting one, and I would really like to find out here in the next six weeks. Do you still have aspirations to buy the Jets one day?

Forever. I mean, it's been there forever. It's been... And is that just the pie in the sky goal that seems unachievable, so you'll just keep shooting at it? It may never have. I think 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. As I, you know, and then in my 20s and 30s, it was, 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. Yeah, it's like a status. Yeah, which has made it challenging because they've gotten much more expensive.

You know, it's kind of like, you know how little kids have like a favorite doll or blanket and they're like, they'll like take it to college? I think at some level with my entrepreneurial journey, like this like little, I'm going to buy the Jets is almost like that little baby blanket. Like it's been part of this whole journey with me when I was selling baseball cards. I was like, one day I'm going to open all 100 baseball. baseball card stores and buy the jet. Like, it's just, it's a very warm, personal, meaningful thing to me.

And it's obviously changed in culture. When I used to say it, it didn't seem like a big deal. Like, yeah, it was a lot of money, but it was like, oh, that's interesting. Now it's different in culture, but it's not different to me. 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. you know, 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. And so that's where we're at. You posted a video recently on social media that I loved so much. And it's this woman coming up to you saying, I know one day I'm going to be somebody. You said, please, look at my face.

You're somebody now. Yeah. Why do you think that hits so hard? It's something I believe in so much, and I believe it hits so hard because the world is really confused right now. We have never been more materialistic. We have never been more status symbol.

We have never been more, how many followers you have, how much money you have, what things you have to justify who you are. We've never been more detached from simplicity. You know? And I just, I'm really sad about that. And I want to be a beacon of changing the conversation. I'm aware that I'm successful and things of that nature,

but it's not my identity. It's not how I get my validation. I like being a good entrepreneur, but I don't think it's what makes me me. And, you know, it was a very simple interaction. She actually snuck out. It was really funny where that was filmed. It's what's fun about vlogging.

She snuck out. Like, it was giving a talk. I was just about to go in the car. She snuck out. And the bodyguards wanted to stop her. I was like, no, no, let her come. And we had this moment. And I knew it when it happened.

Like, I got in the car. I'm like, oh, that might be good. Because I felt it. But it was very natural. And it's what I believe. And I think it hits so hard because it's the truth. And right now everyone's confused. Instead of people taking their validation from the amount of followers that they have

or the amount of money they make or the house they live in or the car they drive. should that validation be coming from being a great father, being a great friend, being a great mother, being, you know, whatever it happens to be, is that where people should be looking? All of those sounded great. Being a nice neighbor contributing to another human being, I mean, we can sit here for an hour and bring up a million things that we all think are good attributes of a human being. Yes, to any of the things you said and many others.

You had another one that hit because I'm a fairly new father. Yeah, congrats. Thank you. My daughter is three. My son is about a year and a half. And this woman was talking to you about how do you shield your kids from the dangers of the internet? Yes. And you said the number one most important thing is you got to build their self-esteem.

Yes. How do you do that? You know, I think everyone's different. You know, I have two children. They're different. I'm one of three. We're all different. And, you know, I think there's, it's a very nuanced question,

but I can tell you, let's first go to the first part. Parents try to focus on the sink, not the well. You can't be there with your kids every time. You're not going to be at that party where people pull out cocaine for the first time. You're not going to be there where their drunk buddy is like, I'll drive and you need them to step up and say no. You can't be there when everyone's jumping off a cliff, you know, on a trip, and it's kind of dangerous.

and like they decide yes or no. Like you can't be there. You know, you know, like this whole world we live in now, like, you know, I can't get over to the fact that there are like 27-year-old men walking around earth that have their parents following them on the phone. And you have moms like calling 27-year-old men on Wednesday night being like, honey, you should go back home. Why are you out?

Like, you can't parent forever. And so the only thing you can do is instill the characteristics that will allow them to make good decisions. So what I was telling that woman, it was in Romania, I'll remember that moment forever, too. I was like, listen, you can block their phone, and you know this. You were a teenager once. When we're all teenagers, anything our parents tell us we can't makes you want it more. Yeah.

Right? And so, you know, I knew unlimited kids from my high school and then in college who were really the byproduct of strict parents, and they literally went to college. and within the first 30 days, fucking did drugs, alcohol, and hoard it up like no one's fucking business because it was all suppressed. And then you had parents and my sister and I didn't grow up with this or my brother.

Like, my parent, mom was very like, no alcohol, this or that. But then we had friends that we would always marvel about it where like they would like let their kids drink senior year of high school as long as it was in your home. And a lot of, I watched a lot of those kids

have much better relationships with alcohol and things of that nature. And so you got to find a fine line but I think it is simplicity. I think it is real. You know, I think one thing that parents should watch out for is shaming anything. You know, like, I think that becomes something

you want to pay attention to. I also think what you're cheering for amongst your kid. Like, if the number one thing you're clapping for and giving trophies to your kids for is getting straight A's, I have bad news. That's a fucking bad formula. because you're telling your child to conform to a subjective machine every three months, which is why so many people go into companies and just work for their review.

Like you've got to be more well-rounded than one-dimensional. If you only cheer for your kid, the only thing you tell your kid, the only thing you tell your kid about positive reinforcement is how good they are at a sport. And then they eventually, you know, like 99.999% of people do not make it to the NBA. well, what does that kid left with? So I think it's important to think about what you cheer, what you shame. And I think the other thing is

I think you've got to tell your kids the truth. You know, like there's an age where your child starts to know that you're full of shit. And I think you have to be very thoughtful about that. And that comes to mind. But listen, it's the hardest job on earth.

Everybody, everybody, everybody. No matter how I talk about this all time, how much I admire my mom, I can rattle off things she didn't do. Like every kid is going to play Monday morning quarterback with their parents. You just want to get them into a place where they're strong enough to be accountable

and say, okay, my mom and dad did this wrong. I'm going to do better. And then you want to find balance because I think right now we have a parenting generation that overcorrected for what their parents did and went too far the other route. And it's like, listen, it's really hard to find the middle. 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. That's everyone's life. 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. You know what's saying that is?

Yeah. That's why I keep yapping. I've heard you say that like one sentence from a podcast. boom can change somebody's life. I'm literally looking at the five people behind the camera right now. Whether it was your grandfather, grandmother, father, mother, brother, sister,

best friend, or someone you admire. Every one of you right now can recall, everyone who's watching can recall something right now that was said that had an impact on that. Why do, what did Gandhi or Martin Luther King or any of the, like, you know, like, what are these people that?

It was words, brother. Fucking words matter. because you change someone's perspective. By the way, whether pro or con, this is why words are dangerous too. There are a lot of people, right now, we're in a time in society where unfortunately a lot of people's lives

are going to be much shittier because they decided to believe someone who's spewing hate. Their whole life will be shittier. Like if they grew up 40 years earlier and nobody was talking that jargon, they would have lived a different life. But right now they're sitting in their head

mad at someone they've never met because someone put something in their mind that they believed. So I just choose to go the other side and try to make it positive because life is positive if you decide it's positive. What was the sentence that changed your life? You know, that's a good question. I would say, I want to really give this a real thought. You know, I'm going to give you a real answer, and it's blurry because it was reinforced.

But my mother early on in my life, and again, I probably am saying this because my sister's here with me. She rarely travels with me. but like I very much remember as a child my mom telling me like I was responsible for my sister. Like that, you know, it was just very, very early. Like my mom was instilling a lot of things into me like you're the example. You're in charge of something happens. How much older are you than her? Three and a half years.

And it happened at a very young age. And listen, my mom was the byproduct of very, very challenging circumstances. And I've said this publicly now for a while. I've come to realize my childhood was shaped by my fear that my parents were going to die. My mom lost her mom at five. My dad lost his dad at 15. And it was a, it was a, it was the soundtrack of my youth. I was scared of it.

You know, there was one time, you know, I'm so glad smartphones exist. I really wish I grew up in that era because I know how everyone shits on it. Let me tell you right now, for all the shitting on smartphones, the most tremendous, one of the most traumatic events of my life was when I was babysitting my brother and sister when I was probably 13 or 4, probably 14, maybe 15, but 14, I think. And my mom went somewhere

and there was a massive accident on the highway that made her super late. And I forced my sister to go on the porch with me and pray. I don't know why we had to do it outside. But like, think about that level of fear. That is not a normal child's thinking. Maybe if your mom's,

like an hour late and whatever, but like I really thought it was over. And like, it was just such a current. In fact, I think my life is grounded on gratitude in my adulthood because I made it to 18 and they were both there and they're still here, thank God. And, um, but yes, I would say the conversations I have with my mother when I was six, seven, eight, nine of like, you're the oldest. You're the, you know, shaped me quite a bit. I'm going to bring it back around to wrestling here.

Thank God. You were a WrestleMania 35. Yes. I was at WrestleMania 35. Yes. It was like the longest WrestleMania ever. Which WrestleMania have you been to? The first WrestleMania I went to, and I need everybody right now because it's a wrestling crew to go back.

If you have this footage, I went to the, what's the WrestleMania that Mike Tyson in Boston? You know what number that is? We had a Austin? It was 19, I think. So that was the first WrestleMania I went to. Yeah, take a look. Yeah, let's just, we have all. It was in Boston.

It was in 1998. WrestleMania 14. Thank you. So that's the first WrestleMania. During the dumpster tag team match, iconic. Everybody, if you go to the dumpster tag team match, this is the era of like everyone has a sign. It's in Boston.

The Jets just stole Curtis Martin from the Patriots. And I get a Curtis Martin Jets jersey and I bring it to the arena. And I had a sign that said Jets, like a Jets side. And during the Dubster match, I walked down and I hang it up there. and I'm literally in WrestleMania with my jet sign in the aisle. Please someone clip that and post it on social. I like to have it. Troy will be all over this.

So that was the first WrestleMania I've been to. Then I was one at the Meadowlands in 18 or 19, right? And then I was in Philly. That's 35. 40. Yep. And then. WrestleMania 40 was amazing.

Oh my gosh. Like that's going to be the benchmark for people who are relatively new wrestling fans. And they got to see WrestleMania 40 when they're two. three, four, five years into being a wrestling fan, they're going to think that every wrestling mania needs to be that good. They should. I think I've been to three or four. I wish I'd been to more, but like I tend to work and I'm busy.

But I, um, WrestleMania 4 is like my life. It's one of the best days in my life. When macho man wins that title, it's like, even right now, the chemicals are going through my body. Like, when Hogan

and, you know, I, you know, it was right around. around the time where I kind of like was like, okay, this is like fakeish maybe. Like, you know, you're still in that. You know, this is a long time ago. I could feel he was going to win it, which also reared its head the next year where I feared he was going to lose it to Hogan and WrestleMania 5. I'm still mad at Hogan for that.

May he rest in peace. Matureman's the one person I regret not meeting in my life. Wow. Yeah, when he died, I was that. I felt like I was going to meet anyone and everyone. ever wanted to. I was believed in myself. I knew my life was going to be a certain way. That one really hurt. That one really hurt. He was such a big deal for me. Who's on your wrestling, Mount Rushmore?

Damn, I should have been more prepared for this. This is such a cliche question. I don't know how this wasn't in my mouth. Macho man. Mine or who I think the four most important wrestlers are all the time. It's yours. You're the one sitting across from my, my, my Mount Rushmore. I'm going to go with the Mount Rushmore because I don't even know if I, I don't really I'm pretty funny. Like, I love macho man, and I gave Y2K some, you know,

like, Jay, excuse me, I gave Jericho some love. But like after that, it's, like, I love the British Bulldogs. Like, the British Bulldogs as a tag team

was very big for me. My Mount Rushmore is Barry Harowitz, Steve Lombardi. You're going with all the jobbers. Iron Mike Sharp. Enhancement guys. Those guys deserve a lot of credit. They built up the guys.

Absolutely. I would say, um... Brooklyn Brawler was a fantastic guest on my show. I'm sure. So good. He's awesome. Um, I think the Mount Rushmore of wrestling is Rick Flair,

Hulk Hogan, Andre the Giant, and I gotta give one to the attitude era. I will go with, believe it or not, I'm gonna go with The Undertaker, actually. I know Rock and Austin and Brett Hart and Michaels,

but I think those, I don't think people understand Andre the giant carried wrestling through the 70s. Because he was the attraction. Yeah, and remember it was regional and when he would go, like, I just think he's just all time.

I mean, he just, I'm devastated and I watch a lot of clips where people do their Mount Rushmore. Andre should be in everyone. And Hogan changed everything. Yeah. Like you could... He made a mainstream in the 80s. Yeah. And then Flair,

when you say Flair, you're also giving love to Michaels and Brett Hart and Ricky Steembo. He was a great wrestler. And then obviously pop culture and like, you know, I mean, the guy literally used to cut promos and be like, we're going to be in Atlanta. Like, he would literally cut wrestling promos to tell all the groupie girls where they were going to be that night. Like, we're going to be in Atlanta tonight at 830.

And literally. And when I was growing up, WCW, you know, NWA, like, that was grown up. shit, whereas WWF was for the kids. So, like, as I was getting older, 12, 13, I'm like, ooh, that's a little, you know. And then, so I don't know how Andre and Hogan, and again, I love Macho Man 10,000 times more than both of them combined, but I don't know if we're actually going to do the actual debate of Mount Rushmore,

how you can't understand that those two have to be there. And then, Flair, look, Harley Race, I think it's, like, really lost in history. like what a massively important champion he was and then it becomes regional right like if you grew up in Texas and you don't say one of the Von Erics you're a bad person and then if you grew up right

and if you're from the Midwest and Minnesota if you don't immediately say right heart's the greatest and he deserves it and like and Gagne's you know and that whole you know but

and then I start thinking about weird things like you know like Gorilla Monsoon like let me give you some Now I'm just getting nerdy. Like our generation, Gorilla Monsoon was the announcer, Ross, all these guys now.

But like Gorilla Monsoon was him and Jesse Ventora and McMahon would get in there. By the way, when I got older and it was like, fucking what a genius Vince McMahon is. Not only would he create the league,

but then he was the announcer so he could tell you what the fuck you needed to think. He was narrate. I told my brother AJ when we started Vayner Media. He's like, literally he asked me. He's like, any advice?

I'll never forget. It was day one. Even though we hung out every day and work together. It was kind of day one of our company. And he said, any advice in marketing? And I said, just tell America what to think and it will work, which has really been weird to see play out in politics. But it's what Vince did. He's like, this guy's really scary. I'm like, oh, this guy's really scary. And that's what he wanted us to think. Yeah. But there's, you know, superstar Billy Graham, Bruno, that whole crew, Ivan Kohloff, you know, then you go into

WCW, you go to the sting. And there's just some really big people that there's just some really big people that deserve a lot of credit and it's so fun to debate this. But Andre and Hogan, I don't know how you don't have them. And I would say flare's right there. And then I think it gets blurry. So many people younger than me are going to go Austin and The Rock. And the reason I put Undertaker in there is I think Undertaker's continuity. Undertaker is the bridge. Yeah. Right. Tuesday in Texas, right? Tuesday in Texas with Hogan all the way through being like so important during the attitude era and then even post, right? You know, Undertaker's there and Tuesday in Texas with Hogan

and he's there after Austin and Rock. Yeah. And I think that longevity and at the level and then even like losing the Lesnar and wrestling, like he did everything right. He's there till the Boneyard match in 2020. WrestleMania 36.

You know, yeah, he's there through all of the important areas. I think that, I think that Undertaker, I actually think, well, you know, I think about this a lot. Politicians, businessmen and women, people in pop culture, entrepreneurs, I actually think I live my life this way.

I think some people get even more flowers after they're gone and get more understood. I think Undertaker will continue over time, get more and more credit. Because when someone's watching this long after we're gone and they haven't seen anyone, because we're all recency bias. Yeah. Like for me, it's my guys. Like, I think Big John Stud matters. That's because nostalgia is a hell of a drug.

Yeah, and you also saw it. I got to see Big John Studd move around the ring when he was still healthy. As a massive dude, you know, that to me is like the way that your era saw Big Show and like, how does that guy be so athletic? I mean, Big Show fucking did a drop kick off the top room. I think that's crazy to me, how athletic. But like, you get to, you know, this is back to the basketball argument. The amount of kids that argue Magic and Bird and Michael Jordan and Will Chamberlain and

but never watch them play and watch some highlights. Everybody looks great in their highlights. What about in their day-to-day mundane? And so, I don't know, I think Undertaker is going to get a lot of love as, like, time goes on. You go to Hawaii in your head all the time, but when you're actually ready to go, there's Expedia. Flights, hotels, vacation homes, cars,

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Find out more at Cadillac Canada.ca. Luxury sales claim based on S&P Global Mobility Canadian New Vehicle Total Registrations for calendar year 2025 for the Cadillac definition of luxury. Who do you think is a completely underrated wrestler? Wrestler? Yeah. 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 3 is not a top 2, 3 match of all time. I have bad news for you. And this is just with love, you do not know what the fuck wrestling's about. I really believe this.

It's hard to argue with that. That's such a good match, way ahead of its time. Macho man was, do you know how I think he is more charismatic than Brett Hart? You know, I think about Sean Michaels as Macho Man a lot, like a modern macho man, like, as a wrestler, you know? He said that he was inspired, the stuff he wore to the ring was inspired by macho man. I didn't know that. It's funny, just being a fan, but not as deep as like some of people watching or you.

Like, I feel Sean Michaels a lot in in Macho Man, because it's a great wrestler and a great showman. Brett was a different, Brett was cool and like his promos were a certain way. Macho Man could like, Macho Man became famous, right? Like, Slim Jim commercials. He would do the Arsenio Hall.

Like, he was famous. And he was a technically strong wrestler. And he could work as a baby face. He could work great as a heel. But to end, that's just me giving macho man flowers. Let me give me some good ones. I think. I do think

Kurt Henning is underrated. Crazy to think he never won a title on a major company or world title on a major company.

He was very underrated. Yeah. I think, um, um, you know, you know who I think was underrated?

I think big boss man was underrated. I think like, like there were some heels that came along that really mattered. I was a big fan of Bad News Brown.

Um, Abdullah the butcher. Yeah. I think Abdullah the butcher deserves more credit for what he represented, similar to Andre. He was traveling. Rick Rood. I think Rick Rood's underrated. Yeah.

I think Rick Rood, first of all, his physique was so ahead of its time. Yes. And just the way he healed, when he used to have like those tights with the faces, I think. And he was really, really strong down in, you know, when he was wrestling Ultimate Warrior, when the Ultimate Warrior was Dingo Warrior prior to them both coming. DiBiasey. I think Ted is a little bit underrated in a real way. Davey Boy Smith.

Oh, so good. I think he doesn't have the flowers he deserves for. I mean, the British Bulldogs was such an important tag team. You know, so some of those guys stand out. I thought Orndorf deserves a little more credit. He was really instrumental in those early days. Yeah. Again, physique, pile driver, executed it well.

You know, that's a tough move. People get hurt, as you know, from that move. And I thought he did that well. You know, some people. Some good ones. What's your all-time favorite match? I already said it, no question. I mean, even though it devastating,

I cried like a baby. I still hate George the Animal Steel. I still hate George the Animal Steal. And he had a green tongue, and I'm a huge Shetman. So I liked them right away because he had a green tongue of that associated. What a great wrestler he was, by the way.

So good. And his longevity, you know? That's my favorite match. I would also say that Wait, which one? WrestleMania 3. Steamboat, you know, that is the match. You know who I liked a lot?

It's a little blurry for me because it was my brother's era. And AJ had a funny one. He's 11 years younger to me. You're 43? Yeah. He's 39, and he was into it early because of me.

So he was like, before the attitude era, he was in that middle thing. Sure, there were some rough years there. Duke the dumpster Drozy and Haku. The repo man. The repo man. Who was demolition, right? Who was also, uh, yeah, yeah.

Um, um, and Tantanka. Yeah. And like, they tried all these weird guys, you know, um. Well, super character based, right? Super character based. And then WCW. Because Doink was so big. Right.

Doink the clown. Then WCW started doing some stuff that was a little more reality base in the NWO. and I think WWF went, oh. Well, NWO, as you know, was a story plot from Japan. Yes. And that was just a good, you know, Bishop, who I love, just did a great job of taking something that worked elsewhere and made it his own. That is the greatest storyline of our last 50 years.

Oh, it's so good. Also, no one expected Hogan, even though it was like, whose side has he on? As he was walking out, it's like, what do you mean whose side is he on? Yeah, Hogan, you know, the documentary, Sheds some light on this recently. Like, Hogan felt the heat. He knew it was time.

Like, makes sense. It always happens. By the way, it's how I root for things. Like, I love a good underdog. Golden State Warrior sucked when I was a kid. So when they were coming up with Steph and Clay, I was rooting for them. Yeah.

By the time they won their second championship, I was rooting fully against them. You know, it's just kind of like how, when you don't care, you'll always gravitate towards the underdog. Yeah. I feel like that's happened in your career? People were rooting for you,

and then you became popular, famous. I'm sure. That people went, huh, hmm. Yeah, yeah, I mean,

I think, I don't know if I can relate anymore. Yeah, and I think, I think that's right. I think there's some truth to that.

You know, I mean, I think it's just natural, right? Like, we always love a good Britney's back bitch, right?

Like, we'll build up Britney, then we'll tear her down, and then we just can't wait for Britney to come back. It's the general public will do that. We, in America, we will cheer for the rise,

and then when it gets Taylor Swift, right? Like, everyone cheered, then it gets to the white humor like fuck that tear down and then after a little while we're like no no no bring it back i mean it's just what we do in pop culture boy bands yeah we love the back street boys then we're like they're corny and now we're like yay they're back you know like it's just what we do in society so yeah i think the more notoriety the no more awareness fame you have that comes along with the territory you know like people love their band when no one knows it then the band gets big and then they shit on it like you know oh well i knew green day when they were playing a thousand people and they're

now that they're playing stadiums, like, fuck you. Like, it's just what we do. Can we talk more nerd wrestling stuff? Yeah, you have a lot of wrestling. We haven't talked about Jake the Snake Roberts yet. Oh, sure. The missing link. I've got, like, spitting the killer con.

Like, I got some stuff that I want to get off my chest here. You have a lot of great wrestling collectibles that we see in the background in your office. A lot of L. Jan. You've got the winged eagle cut in half. Why is it cut in half? There was a, what is the name of their channel? A really great YouTube channel. A father and son will it cut?

Oh, they're looking on the inside of things, right? Yeah, yeah. For the best. They did that for me. Oh. Yeah, yeah. Do you have a wrestling piece of memorabilia or collectible that you're super proud of? I just bought it.

Okay. I just bought a, so LJNs are my favorite collectible. Maybe period. That's a huge. And I mean, I'm a huge sports card guy, but like maybe my favorite thing. And again, probably because my sister's here, like she knows we had this one holiday where our brother was about to be born. And our mom was very frugal. We were immigrants, but this one holiday, she just went ham and we got everything.

She got like the Barbie stuff. I got the wrestling stuff. And we always think about it. And, but in general, the LJN wrestling figure is everything to me. Like, it is everything to me. I just bought. So I don't know if you know this. In the LJNs, when you bought them, it came with a poster.

Yeah. And it's just like, you know, my sister might not even know this because I would lose things immediately when I would get a new toy. the second Star Wars was my first love when I would get a Star Wars action figure the lightsaber I would literally lose it within two hours within two hours I had to go to my mom's kitchen and be like

mom do you have toothpicks because I had to use the toothpick as the lightsaber same with the wrestling figures that poster would be gone in a second but the wrestling figures came with posters and I don't know if you know them I remember yeah it was very like drawn a certain way anyway

on heritage auctions a few weeks ago the original art, like the art that made the posters went up for sale, and I bought a bunch, Mr. Fuji. Oh, wow. Who I loved, I loved Mr. Fuji. I'm thinking about becoming a wrestling manager.

Is that right? Yeah, it's on my mind, by the way, just to pivot hard. I'm thinking that I need to hit up Triple H and, like, I think I should have one stint as a manager. Okay. Maybe next time WrestleMania is in New York. I think I'm ready to do it.

I think I should be Logan Paul. Paul's manager and maybe turn him good. He's still heal, right? Oh, yeah. People hate Logan Paul. Hate the character of Logan Paul. He's got to have an era where he turns good. Since I discovered him and social media,

I think it's a perfect plot. You discovered Logan Paul? That's right. I'm being dead serious. Logan Paul's first. Listen, Logan was going to get discovered. That's a good line to say as a wrestling manager. No, I'm very aware.

I discover Logan Paul and I'm going to flip him. You know? I'm going to bring him back to the good. died. I knew him long before the fame. Yeah, his first marketing campaigns were with VaynerMedia. Oh, wow. Because truth be told, Jerome Jarre, who was a Vine celebrity himself, discovered Logan, put him in front of me, and I said, this kid's got it.

And we put him in a Sour Patch Kids campaign. We did a contest called for Virgin Mobile, finding the next Vine star. And he was the winner. But, um, I, I, I, I bought these original drawings of the LJN posters, and I'm just besides myself happy. I have a bunch of black cards. I have a ton of Hasbro, green cards,

one, two, three kid, aka Lightning Kid. Yeah. What about, I know you're deep into sports cards. Do you have any wrestling sports cards? Yeah, I have, I have, I have, I have Andre's rookie, which is the hand cut, 1978 black and white. Yes.

I have one of the only PSA 10 Rick Flair rookies. Oh, the 1982. I've got Macho Man 85 tops, rookie. I got Hogan. I think I have a Hogan PSA 9, 82. Oh, wow. I have a bunch of the rocks, the bumblebee rock. Oh, the University of Miami football card.

The perforated edges. Bumblebee tuna fish. Yes. Bumblebee tuna fish. And there's a story behind that. My buddy Jamil loves to tell this because he's a Miami guy. It rained that day. So you got the entire team in this like perforated thing.

It rained that. a bunch of mussel got fucked up. But I think a lot of people were just using it as like protection from the rain. I don't know that story. That's crazy. So that's why there's even less of the Bumbley cards. I have a serious wrestling cart collection. And, um, and, and, and I've, I have some weird stuff like stickers, like a lot of fun

stuff. I also love, like, Nikita Kohloff, the fan, you know, I love the free birds. And like, I've picked up a bunch of member of me. I've been thinking about starting to collect old wrestling bags, because I used to really love those. Simon Krausers on Oak Tree Road in Edison. And that's how I learned, you know, before ESPN started to air other wrestling, the AWA and the Texas League stuff. The only way I even knew other wrestlers existed outside of WWF was the magazines.

Sure. You know, like, who's Dr. Death, Steve Williams? You know, like, I was like, who's that guy? And like the Blade Runners, the Ultimate Warrior and Sting were tag team champions, I think in the UWF as the Blade Runners. Yes. Like, like, I had a lot of wrestling knowledge. Back then. And you still do.

Like, so you mentioned Jake the Sake Roberts. What a promo. Bro. I was so scared of that snake. I'm still scared of that snake. Damien. Damien scared the fuck at me. And when the earthquake sat on Damien and killed Damien,

it's still one of the great wrestling movies. I loved earthquake and typhoon, the natural disasters. Do you remember when Damien legitimately bit macho man? That's right. And there was blood coming out of, his arm. That era, you know what I remember that I rarely see people talk about is on Saturday night's main event when Orndorf and Hogan both jumped out of the ring and landed at the same

time and they called it a tie. Do you know this? That was a week. Saturday night's main event, like, again, I wish the kids understood what the world was like pre-internet. Pre-internet, there was so limited information and stuff, everything was a big event. Yeah. I saw something online the other day

that said like 1985 was like the best year ever like for pop culture and maybe it was Bill Simmons they just rattled off it. It was like Ghostbusters. Back to the future. And I was listening. I was like, man, that's right.

And I was 10. It would be like Rustinia 2. I would tell you V friends. I'm pretty sure the reason I created V friends is how I affected I was that I grew up in this iconic 80s pop culture IP. But like Saturday at Spain event you understand.

With no internet and no phone, you didn't know shit was happening. Yeah. You'd just be watching TV and they'd be like, this week, Saturday it's made about it. I'm like,

this, like you'd be stunned and pumped and you try to stay up late because you were young and it was like, aired late instead of SNL. But that Hogan-Orndorf match, I'll never forget

because I thought Orndorff won, which was like stunning, but they both landed at the same time. I'll never forget that. And then you would wait to get to school on Monday morning. And talk all about it. Yes.

And you would, would find your best friend who also loved wrestling. You'd be like, can you believe what happened? First now, my son, him and I were watching Rhonda Rousey, went in 17 seconds on Netflix. And he's talking to a friend about it in a second. So there's no holding on to it. There's no that anticipation of, like,

talking about it on the bus. Like, yeah, I mean, those things are romantic to us, but I'll say this to everyone who's romanticizing. Technology always goes forward. Today, what kid, like, one day my son's going to be like, remember when it was just texting, not going into, to a time machine and showing, like, like, it's going to keep advancing. Yeah.

You know? Yeah, and I say this all the time. Nostalgia is a hell of a drug. But I think that recency bias also plays a big factor into all of us. Oh, it's why everyone's Mount Rushmore's are broken. I'm kidding. I'm kidding everyone. But it is true.

Like, like, if you're of my era and then, like, I learned wrestling, you know, I'm rapping about some wrestling here. I learned a lot of my wrestling. There was a, Liz, I don't know if you know this. There was a guy who lived by Michael Gorellick. like on the other side, he must have only been 10 or 15 years older than us. He was probably

in his 20s, but he felt like he was 80 years old. But he was the one that taught me a lot about wrestling. He would wash his car and we were just riding our bikes. He told me about Koloff dropping the knee on Bruno Samartino, Madison Square Garden and winning the title. And again, there's no internet. There's no...

Like, you know, it was just like... And for him, he's... If he's still alive, I hope you are, and he's watching this, he's like, he's like, what are you talking about? Bruno's on the... Because even though I'm going old school, I can't go back to Bruno or further...

Or, you know, you go back far enough. Like, you know, um, you go into like, buddy Rogers. You go into like, you can go very old school. Right?

Um, and then there's like dusty roads. And there's just like a lot of people to mention. It's hard to pick four. I have loved talking wrestling with you. And I want to be super respectful of your time. This has been amazing. Gratitude is such a huge thing for you and you.

your life. It's a massive thing for me in my life. I wake up every day, say out loud, three things I'm grateful for. Do the same thing. My wife and I do it before we go to bed. It's the last question I ask everybody at the end of every episode. So Gary, what are three things you're grateful for right now? I'm only grateful for the health of my family. Like, I do not comprehend anything else to be grateful for. Like, meaning I keep it so basic. I just want the people I love to be healthy. Like, I, you know, I can be grateful for a million things,

but they all feel frivolous. And that level of simplicity is really real. I'm also grateful that the Knicks are in the Eastern Conference finals. I'm really happy about that. By the time this airs, they may be in the NBA finals.

That would be, when is this airing? Maybe like two-ish weeks. Okay, good, they may be. Honestly, that has been the framework of my life. Like, I think it's important to go lower than that for fun. Yeah. But if you're asking the truth, it's really hard for me to get excited about much outside of that. And I would say in that quiet, in that understanding, all the highlights, all the low lights,

all the fancy things, all the com things, they're just all so secondary. I've not been able to live my life for a very long time now in any other way than thinking, okay, this thing or that thing. How much does it really matter if XYZ is happening, which is ultimately somebody in my family, not in a good spot health-wise. So I'm only grateful for that. It's the only thing worth being grateful for. And for me, with me,

everybody else can do what they do. But for me, it's how I see it. I love that. I also want to thank you because, randomly, for absolutely no reason. For a very specific reason. You DM'd me on December 8th, 2022. Keep going, CVV.

That's it. Can I tell you why I did that? This has been maybe the coolest chapter of my professional career. Probably around that time, maybe a couple years earlier. I'm like, oh my God, if I take one sec... So I'm consuming content. Sure.

If I see something I like, if I take one second and DM this person, they're going to think it's cool. That was super... You know, that's not how I ever saw my life playing out. You know, I was just wanted to be a businessman. I never knew that people would know who I was. I wrote an article about this called the Ricky Henderson rule. Ricky Henderson, when I was 10 years old,

I went to a Yankee game, and I thought he winked at me, and it meant everything to me. I've now come to realize he probably winked at a girl in the crowd, but I was sitting next to. But, I mean, here I am. Forty years later, I can feel the way I felt when I thought Ricky Henderson winked at me. To feel that for you when you got, do you remember? Yeah, I remember. It felt good. By the way.

Did Gary Vee? Back to wrestling. When the rock followed me, that meant something to me. Like, I know what it feels like, and so I want to scale positivity. And I don't do it frivolously. I want to do it for things that I think of someone's emerging, someone's doing something interesting. I think people need, you know, I know it might be a,

I know the game's hard too. I know what people do when they make content, when it's not an easy game, it's so easy to quit. You know, you talked about the cliche one. One video seven, nine, ten, almost everyone does that. Yeah. Do you know how many get somewhere and then still get, give up, get to 150,000 followers, but then they get stale for six months, and for some reason

they stop and they never get back on. So I know that, I don't know what is happening with you on the other side when I say that, or to the thousands that I've sent that message to. But I know the outcome can't be bad. You know, either they needed it as an extra boost to keep going, or they think it's super cool, or even if they don't think I'm cool, it's just nice. Like, even if it doesn't carry a lot of weight with them, who doesn't want to hear like you're doing a good job? Yeah, the rock always says this quote that I love. It's nice to be important, but it's more important to be nice.

Yeah, I mean, that's very real. I believe in that the most. It's a great quote. So good. Gary Vee. Thank you so much, brother. Thanks for having me. Appreciate you.

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