How Gary Vee Predicts The Next Facebook (Every Time)

All right, we got Gary Vee in the house. Everybody knows Gary Vee because he's all over Twitter and Instagram and LinkedIn, and he's invested in Twitter and Slack and Facebook before they IPO'd. Gary's fun. We brought him on and our goal was let's ask him a bunch of questions that we're genuinely curious about, like which of those investments actually paid off the most. And it was a very, very surprising number, I thought. We asked him about the mindset and what he noticed hanging out with people like Zuck or Logan Paul or different, different characters like that. So enjoy this episode with Gary Vee.

It's a good one.

Gary, what's going on, man? How are you? I think Sean saw something recently that you'd posted that I thought everyone knew about you. Sean, what was that thing? The report card?

Most podcasts start with an intro. We start with a little ball busting. So I have here Gary's high school report card, which you tweeted out, to be fair. So I'm not, I'm not putting it out there you didn't already do. But I thought this is kind of amazing. So you tweeted out a picture of your high school report card. I'm just gonna read off a few, uh, few of your achievements. Gary got a, a C in ceramics, a D in English, an F in German. Uh, PE, you got an A. That's the only A you have on this report card, I think. Uh, algebra, D. This one's kind of amazing. Speech, which like you are known for speech. You got a D. Driver's ed, D. Gary, you were, what a turnaround. What a turnaround. What's your reaction when you see this?

That a lot of data in the world is dirty. It's fake data. And I think school grades are just not a tremendous indicator of what's gonna happen. The speech one is crazy. The report card I tweeted out was the recap of all 4 years of high school. So little fun facts to build on top of what you just said. I got an F in all 4 marking periods of German 1 freshman year. I retook it sophomore year. I got a D in the first marking period and then proceeded to get all Fs. Failed language my freshman and sophomore year. And in the state of New Jersey in 1994, if you did not pass 2 years of language, you could not graduate high school. So I walked into junior year high school. And took Spanish 1 with all these 9th graders as a junior. And I had the pressure on and luckily I got Mrs., Senora Kennedy saw something in me and forced me through the system. Otherwise it was over for me. But yeah, I mean the speech one really stands out to your point, Sean, right? Like to think that I got a D in speech, which was give a speech in class, right? Which I did well. It's just that I, you know, I told my mom, my mom and I talked about this this weekend. I literally did not open a book in 4 years of high school and did zero homework. Like, you know, they would have, everyone who's listening went through school, I think, like they would assign a book report and like, it's not that I did it poorly. It's that I didn't do it. Just like, didn't ever. I literally, in 4 years of high school, did zero homework. Zero. Like, I, Something happened where I just knew that, you know, at that point, high school, I was already working in my dad's liquor store and selling a lot of baseball cards at shows and just kind of, and it was, look, this is pre-internet. The world was different. I grew up in an immigrant family. We lived in like, we just moved to like rural New Jersey. When I tell you we lived in our own little 4 or 5 person cocoon, my family, we really did. It was very, very, very in hindsight, deeply immigrant. You know what I mean? Like we didn't have like Ameri— like my parents didn't have American parent friends. Like my mom wasn't friends with any of my high school friends' parents. Like my mom asked me about what I'm doing for college February of my senior year. I was like, mom, it's over. I'm not going to college. She lost her mind and forced me to like go. And I got like a postcard in the mail from Mount Ida College, filled it out. And that's literally how I went to college. Like, so, you know, I think if If I was growing up today, my intuition is that it would've been okay for me not to go to college and it would've just all been handled differently. And honestly, I think my teachers would've said to me, like, I have a bright future instead of saying what they did back then, which was you're a loser, you're going to be a garbage man. That was the big thing, Sean, Sam, in the '90s, your teachers would tell you you're going to be a garbage man, which I think is really crazy because actually it's a very good living with a high pay— it has a high pay scale.

Our friend just started a garbage business and he's doing like $300 grand a year of income.

Joke's on you, Miss Kennedy.

Yeah.

Um, one of the things we do is always just, what are you excited about? Like, what products are you seeing? What people are you seeing? What cool stories are you seeing that are kind of— that you're genuinely excited about?

Have you guys seen Break the Web?

No, what's that?

Dude, they got a great tagline. So it's, uh, breaktheweb.co, the internet's official scoreboard.

This app's got my attention. Trending topics on Twitter was so big for me back in the day when it was desktop only. Break the Web is an app, like, it's just what's trending right now. And it seems like the underlining tech is pretty damn strong. Like, you know how everybody loves to throw around AI or this and that, and you're like, if you're smart, you're like, this is just a collection of APIs or anything like This one's a little bit better. And like, I don't know, I've put on my home screen, which is not something I've done in a long time.

Why?

Why do I like it?

Well, yeah, I mean, it's like, I'm looking at it now and you just showed it to me. It was all the news stuff. I don't really pay attention to, I don't like your, yours. I saw the word Gaza, Trump, and like 5 other words where they're important, but like, I don't, I'm not going to like read like news.

First of all, great observation, brother. For me as well, like honestly. Something that's on my mind is everyone needs to consume less news 'cause all it does is push fear and negativity and like, it's just so scary, like how fucked up that is. So it's funny, same brother. I don't really click into that stuff. So right now it's brand new. And when I met with the founders, I only met with them for like 10 or 15 minutes. I asked them real quick, I'm like, can we get this categorized out? And they're like, yeah, that's on the roadmap. Like I just want, I need pop culture and consumer trends. So like to me, I'm like, when I look at Madonna fan, I'm like, what is that? You know, Madonna mistakenly scolded a fan. Again, right now what's interesting though is that it's a great indication of where we are in society. Like back to when Twitter trending topics, it was less political and it was really valuable. Like the reason I like it or the potential of it And obviously we're in election season, so now this will get eaten up, to your point, Sam, on this stuff. But it is an indication of the pulse. Like, I'm always looking for what's the indication of the pulse of what people give a fuck about.

Dude, so these guys, so it looks like it only has 90 reviews. Oddly, both of these guys used to work at a bakery. The CEO worked at Pete's Coffee. The other guy used to work at Specialties Cafe and Bakery. So they're both, uh, lovers of baked goods. They decided to launch this. It's 3 years old though, but it's not popular yet. What do you, so what do you, what's your prediction? This thing's going to be huge?

There's no prediction. Back to shooting the shit. To your point, Sean, I'm not overly like, oh, Break the Web is going to be the best. The concept of date. So I have a new book coming out soon this year, right? I finally feel like I've synthesized what I actually do, like long form Twitter. I think literally have a meeting today where I'm gonna post my 100 most successful YouTube videos on Twitter here over the course of the next couple months. Try to stagger it a little bit because it's just very clear that Twitter is pushing video. It's gonna push it, right?

I, I don't know if that's gonna work. I think they're, I agree, I agree they're pushing it, but I just don't find myself using it that way.

Yeah, that's a great call, Sam. Like what I know is that I'm, I never have an interest in guessing if something's gonna work. I have an interest in executing on anything that might work and then dealing with the ramifications of the upside.

I guess when you can test for cheaper than it almost costs to guess, right? Like it's not expensive to take your best YouTube videos and have somebody repost. That's an easy way to learn because, you know, you talk about day trading attention, right? All trading is mispriced assets.

That's right. And I would, and I would argue that attention is the most mispriced asset right now that most impacts everyone.

All right, everyone, really quick. If you've heard this podcast before, you know that Sean and I think that the most important skill set you need in business is copywriting. And so what we did was we went through all of the podcasts that we've done. It's like 500 of them, and we found all the best copywriting tips, our resources, our frameworks, our templates. We aggregated all of them into one simple document so you can skim it all and get everything that we've ever talked about with copywriting. It's in the link below. It's awesome. Check it out.

So why is— why is that?

There is nobody that will ever listen to this that doesn't need attention as a currency to achieve what's in their stomach. Whether they want to raise money for their PTA, be president of the United States, get more listeners to their podcast, sell their sneakers. They're the only asset class that I think is universal is attention. Even a parent trying to home parent two children need their kids to listen to them to be able to get the message across. The currency of listening is, or consuming is profound. And we're living through the mass fragmentation of that, right? If you think about, let's use parenting, was a lot easier to get your kids to listen when in 1954, 80% of families sat down and had dinner together and for like an hour and a half and you did it, right? And like, so those parents were able to message in a very interesting way. Whereas now they still can, we have technology, you can send a text or a Sam and Shawn clip to your kids to get them to think of something. But there's also so much supply, right? With the demand side being the same, there's only so many hours in a day. Now the human brain, I think, has capacity to keep a lot more information than we think. Nonetheless, for me, more narrowly, as someone who loves business and loves, you know, to think about it, you know, it doesn't matter what you're selling and it doesn't even matter What you're saying until you first get their attention and then everything is about what you're saying.

Right.

What, what's interesting to me is I think of it in the acronym I use internally at VaynerX, VaynerMedia is PAC, platforms and culture.

Right.

And so Break the Web plays in culture, right? Like there's two different currencies that I think about constantly or two different frameworks. One is platforms. What is, what are the top 25 platforms that have people's attention doing? What do they care about? From Snap to Pinterest to LinkedIn to YouTube, even within themselves, YouTube Shorts differently than YouTube. This collective of like 15, 20 places, right? That really have quote unquote the attention. What are they up to? How do their algorithms work? What are their features doing? And I think about them on a day-to-day basis, right? And then, and then I think about culture. Like what is the slang? What is, what is the things of interest, the people of interest? Right. And then it becomes a framework of like what's overpriced and underpriced execution. So, for example, I think Super Bowl is the most underpriced media in the world. It's very hard to get 130 million people to watch 30 seconds of a video and actually want to and pay attention to it. Right. So that $7-8 million vig, I think, is great. The problem is the creative is the variable of success, right? So the media might be a great deal. But if your 30-second video is forgettable or stinks, or you overpaid for making it, right? Verizon paid Beyoncé to be in that commercial. If they paid her $500,000, I think they stole her. If they paid $40 million, I think they overpaid for her. I don't know what the number is. My guess is it's somewhere in between. But that is basically how my brain works and how I think about communication and marketing and brand building and perception changing and just the whole world. It's how I think about the world.

Have you guys seen, let me tell, let me ask if you guys have seen this in terms of cool shit. So, uh, Perplexity is awesome. Um, but they have this new thing with, I didn't see them talk about it a lot. It's called perplexity.ai/podcast. They've come out with a daily podcast that's 5 to 10 minutes long that's written by Perplexity and it has beautiful background music and they've got this British guy. Have you ever seen those like Planet Earth videos where it's like, now we see the mother cheetah going through the— Yeah, they've got this voice that sounds exactly like him. Reading like the script and it sounds awesome. The voice is powered by this thing called, uh, ElevenLabs. Dude, I went to ElevenLabs, Sean. I uploaded a ton of our voice and I was like, fuck it. Let's just see if I can make a podcast. It's way better. It's like, it's the best thing I've ever heard. Have you guys seen, they've come out with this podcast and see the voices?

If you ever want to see Sam speak Hindi, ElevenLabs made a clip. They just translated the podcast, auto-dubbed it using AI in Hindi. And it's phenomenal, by the way.

It's something we've been working on for about a year. Like, I'm— I think next year is the full year where like every single thing I do, every video, every language, like we're there, dude. I haven't seen Sam. I haven't seen the podcast, but I just took note. Like, I can't wait to listen to it.

Like, it's so good. And they've not made a big— this has not been like a big hoopla. They haven't done— I randomly came across it. I was listening to it. I'm like, I'm going to listen to this every day. This is great. It's David Attenborough telling me about like the news. It sounds awesome. Uh, which language, which language you going to do? Should we do Hindi? Is that the one?

I'm doing everything.

Like, yeah, if you're going to do one, you might as well do all. Yeah.

It's just like, I just think that I also think like everyone's going to go after the big one. Like, for example, I get excited about Portuguese. I'm like, fuck it. Everyone's going to go to Mandarin and Hindi and like the big number, you know, I'm like, I'm just going to own Portugal and Brazil. Like, you know, just like, but, but that's tongue in cheek. I think the reality is over the next 3 years, all of it's going to go down in cost so much. That it won't even like the, the us in 7 years are going to laugh that we ever had it just in one language.

If they won't even understand, they're like, dude, have you ever seen that talk that this guy Alex Schultz gave about Facebook's growth? He was the, he was the top Facebook growth guy. Like early on, he was when they created the growth team was him, Chamath, and the guy, I think Javier, who now runs it. And he's like, he put a chart up and it was a, it was a YC talk. And he puts a chart up on the screen. There's a bunch of dots. He's like, you know, all these dots are feature releases. And you could see one dot where everything starts growing right after that. He goes, anyone want to take a guess what that dot is? People in the audience like photos, photo tagging. It's when you release mobile. What is it? We don't know. And he's like, language translation, local language translation. He goes, the biggest growth driver in Facebook's growth, bar none, was when we localized the service, which he's like, was not easy. They actually, I don't know if you know this, Facebook had to do like a Wikipedia thing. 'cause there was, you know, there's 186 countries that they had to deal with. And so they were like, we need users to basically retranslate the site for their local region. And they incentivized people to do that. And that's how they mass translated overnight. No other social network did this and it took off. So that was the first time I heard about this. The second was when we did our basketball camp with MrBeast, which Gary, I invited you to, you gotta come next time. MrBeast, basically we host a basketball camp at his house and he did this presentation. He's like, He's like, here's one thing I'm doing that nobody else is really doing, which is every video I do, I now created channels in Portuguese and everywhere else.

He told me, Jimmy told me that whole thing several years ago.

Like such a good bet.

By the way, tell me about this basketball camp because I'm playing basketball tomorrow at 6:00 AM. Like, this is how much I love it. I'm 48.

Like, you'll fit right in. We got, there's plenty of wheelchairs and ice and bags of ice.

Dude, it's nice.

I'm great, but I'm a '90s Knicks fan, so no easy layups. Is that politically correct in this basketball camp?

Yeah, yeah, you can hack your heart away. It's all good. Actually, I wonder if you do anything like this. So we do this thing where it's called Camp MFM, it's My First Million MFM. So we were like, we like the idea of getting together. When you go to a conference, you end up having a good time. If you go speak somewhere, you end up having a good time. But there's kind of this dread in my stomach of like, fuck, yet another conference. I just don't want to do the boring I just, I guess, have a resistance of doing the same thing everyone else is doing in general. And so we were like, how do we get the benefits of going and networking without ever calling it networking or a conference or anything else? And so we created basically an adult summer camp. It was like, what if for a weekend we just rented a house? And in this case, we actually just stay at MrBeast's house now because he ended up wanting to come. And so we go to his house and then we bring in a trainer from the NBA. He treats us like we're washed up NBA players, basically puts us through their program. And we just play ball all day.

When is it?

One just happened, but it was big. It was like the founder of Airbnb, MrBeast, all these guys.

Joe's the best. Joe, I have an email from Joe that says, Gary, we're fans. We want you to look at our company. And it was joe@airbedandbreakfast.com. And I never saw it, you know, or maybe I did and just like, but I look at that email. I have it on a separate laptop and I look at it once in a while just to like, I love it. I like, this is actually a fun segue back to chopping it up. If it was just us three and everyone's just this, where we're going, where do you guys sit on losing? So we just talked about basketball. So I was just thinking about me going to this basketball thing and like my favorite thing in basketball in pickup is to lose the first game. It is my favorite. And I talked about this on Steve Bartlett's podcast a couple a billion fucking emails about this. There's something that just like the blood in my head, like everything transforms in my chemicals and then everything in life, like everything stops. And the only thing that matters to me in the world is that we have to win game 2.

That's so funny you said that. When we did the camp, the same thing happened. The very first game, I'm trying to be the host of the event, so I'm like, okay, yeah, yeah, you guys play, I'll sit out first. No problem. We get in, I'm like, I'm passing the ball. I'm like, oh, that's Joe Gebbia. Let me not. Let him drive. I'm not going to try to hurt the founder of Airbnb or MrBeast. Oh, that was cool, man. You know, I see someone taking a video. I'm like, that's cool. That's going to be a cool clip. That's going to go viral. Then I'm like, wait, fuck that. I'm in the clip. He's scoring on me. And I was like, he's no longer MrBeast. That's Jimmy and that's Joe. And now we're competing to win. And then the whole event got a lot more fun when it equalized.

Correct.

Everybody, all the job titles dropped and it's basically who's here to win, who's here to play. And that's when it got real.

It's why I love entrepreneurship. Where I was, where I'm going with this is that email like excites me. You know, like I'm like, yeah, eat it, Gary.

Like, dude, that one would have been a bigger one for you than Uber too.

No, it wouldn't have. Maybe, but no, because I was the, they both probably, believe it or not, this is how much startups were back then. They both would have been priced between $4 and $8 million.

That's crazy, right?

I know, bro. I got into Tumblr's B round. B, Series B, not angel, not seed, not Series A. I got into Tumblr Series B. This is actually it right here. This is my Twitter, Tumblr, Facebook stock. I got into Tumblr Series B at a $14 million valuation.

That's like, you know, pre-seed now.

That was literally 2007 or '08, right? We're only talking 16 years ago. So like you guys are young dudes, so think 16 years ahead. How old will you be in 16 years, Sean?

Dude, I don't even want to know. 52, 50?

I don't know.

Sam?

How old am I?

Great. Honestly, no bullshit. I don't know if you guys hang out with like 60, 70, 80-year-old business people. Like I do a lot of that because it's the best. I mean, to me, the two extremes are the best, right? Hang out with the 17-year-olds that are like shitting, listening right now, shitting on all of us saying these fuckers are going to, Wait till they see what I'm going to do. And then 73-year-olds who are like, just like the amount of 60s, of 60s, forget her, I think is like literally children, 70 and 80, 70 and 80 to me, just, it's stunning to me how many 73, 75, 77-year-old businessmen and women I know that go at it because they love it. It's still what they do. And it gets me excited because at 48, it's like, man, I'm still like, I'm in halftime, right? Like I'm in, Like, you know, I get excited about that.

I wanted to ask you about that. So I think you and I kind of have similar backgrounds where it was like raised around like, like kind of a rough crowd every once in a while.

Yes.

And still kind of have a little bit of that where like I enjoy like doing like hoodrat shit every once in a while.

Same.

And Gary, Sam's nickname on the pod is Hose Water because he's just no water fountains, baby. Just drink it straight out the hose. So he's Sam Hose Water Parr.

Dude, I loved— man, hose water was the best.

It's the best, dude. Summer hose water.

I drank out of the hose literally from 1982 to 1989.

Dude, I peed in the backyard more than I peed in the toilet. Oh, 100%. Yeah, they used to call me Look Ma, No Hands, like every day. So listen, I had a question. So you— so look, we're all three probably a little bit similar where it's like we kind of like did a bunch of scrappy stuff and now Gary, you're older and a little further along in your career in terms of success than we are, but we've both done some interesting, or we've all done interesting things where we're able to hang out with some of these guys who are like legitimate billionaires. I'm sure you're, I don't know if you are or not, but you're in that ballpark. And I see with Michael Rubin and whatever, you, you know, you hang out with some of the shot callers of the world. What do you think is the difference between the store owner who's doing like, you know, a retail guy doing half a million or a million dollars a year? The $10 million a year business, the $100 million net worth person, and the billion dollar net worth person. Do they all have similar-ish mindsets? Just maybe luck or industry? They picked the right, a different industry.

Yeah. Two things. It's, it's 12:34. I still don't know why 11:11 has everyone's attention and 12:34 doesn't. The 1, 2, 3, 4 is just so cool.

Should we make a wish real quick?

I don't know if we should make a wish, but we should start a trend and try to make 12:34 matter for entrepreneurs. That's a really fucking fun question, Sam. My brain, as you were asking it, goes immediately—

Focused on 1, 2, 3, 4.

Well, yeah, I just have to look over and see it. I always thought about 1234. I've always thought it was interesting that it has no pop culture relevance. I believe the first thing that goes through my mind on this question is risk tolerance and fear. Right? So I think it's fear.

I just had an idea. 1234. I got it. I get it. I want, I gotta use it. 12:34 should be where you shoot your shot.

I love that.

When you see 12:34, that's when you gotta send that text. You gotta send the tweet. You gotta send the email right there. That, that's, that's the idea for 12:34. We can make this a thing.

Can you get somebody to register like 12:34.org? Like, I feel like, you know, um, I don't want these hustler kids, like the 13-year-old me would listen to this and immediately register 12:34, uh,.com. Um, I think it's fear. I think about my dad a lot. My dad, I think it's how people view their ability to go backwards. So I think there's something very scary about my chemicals. And Sam, I've always felt this in you as well. It's funny that you brought it up. I don't know if you, I don't know you well enough to know this, and I'm not even sure you're going to believe me when I say it, but I do think you have a good shot of understanding what I'm about to say. My favorite Rocky is Rocky VI when he goes back to Philly with nothing. Yeah. Sean, there's something so weird in me and it's almost like, am I sandbagging myself? Like I'm going to be very vulnerable here. Like I don't view it as like I'm cool. I actually view it as I'm potentially flawed, right? Like there's something in me that romanticizes being okay with it all falling down. I'm back in Queens in a $400 a month apartment. The entire internet is like, see, he was fucking overrated. I told you. All the people that love me, all the friends they have that don't love me are like, see, your fucking guy was a loser. He fucked it up. He sucks. I don't know why I like that, but I believe, Sam, to answer your question, it's something to do with that chemical. I believe the people that, I think you brought up some good stuff. I think a lot about if my dad had a supermarket instead of a liquor store, I would've taken that to way bigger heights. 'Cause liquor was, you couldn't ship it.

And sure. You know, like that's like the luck component.

Yeah. There's a ton of serendipity. Like honestly, I think a lot about if my dad didn't want me to work in his store, I would've went to, 'cause I fell in love with tech, I might've went to California and who the fuck knows what I've, I'd created in '95, '96, '97, like could have had one of those Mark Cuban moments. So I think about that or, you know, like I think when you can sell, when you can— for all the— everyone who's listening and if you have kids like this, if you can sell, you're in the game, right? Like if you can sell, you'll never be like zero, right? And so what do you got here? Is 1234.com available?

No, dude, 1234 is owned by like a telecom.

Yeah, that's what I figured. That's impossible. I like the one, like the 137. Yeah, do that.

Are you kidding me?

Dude, I love that.

That was so dope. I'm so pumped about this, bro.

The funny thing, by the way, Ben, my guy, he texted us a screenshot of GoDaddy. It's 1234.org, $15,000. He just said, pull the trigger, question mark.

No, no, don't pull that one. Yeah, actually, this is a good one. I never think you should overpay for names because I think names are made.

Dude, I agree. I agree.

Right, Sam?

But do you know who disagrees? Fucking, uh, Dharmesh. Dharmesh at, um—

I know.

Dude, I've been with him multiple times. So Dharmesh, uh, founded HubSpot, which bought my company. And I've gotten close with him. He's like, he's like, dude, I bought chat.com or chat.com today. I'm like, why? He goes, because it was available.

I was like, what are you going to do with it?

He's like, I'm not sure, but I'm going to figure something out. But I paid 8 figures for it.

Yeah, look. He's smart. He knows like that, you know, look, as long as dot-com, I mean, to me, the scary thing for, let me, let me take a step back, not go too fast. He's smart enough to know he could probably flip that because it's a very, very, very big deal. On the flip side, there is a little concern for me of what happens when this no longer becomes the remote control of our society. right? Like I'm very fascinated by 20 years from now. Talk about 16 years ago on Tumblr, 16 years from now, if you told me that 16 years from now we live in a predominant VR world, I would be like, maybe, like I can see that possibility, right? You could see that it's pushing in a direction. I don't think it's gonna end up being these Apple Pro, you know, Google Glass, Snap, the Facebook thing. Quest. My intuition is that it's going to have to be much more lightweight, but I never underestimate the human being. I'm positive somebody's going to make the contact lenses that work like this, and then we're off to the races. Because now, back to the way I think about day trading attention, this no longer houses the attention. Now it's housed here. Whoever controls that paradigm wins big. And then all of a sudden, does.com even matter in that? Is that how the UI/UX works? Because.com didn't matter at all in 1990.

Dude, that's how I feel about SEO businesses right now with, with, well, that's exactly right. If it's ChatGPT and, and Google's just trying to give you the answer.

So that's, that's why VaynerMedia never did search. When I started the company 14 years ago, everyone's like, what the fuck? Why don't you do search? And I was like, first of all, I thought if I built a very big company, I'd be able to M&A search if I wanted to add it, right? It was already established. I grew up on search the decade, the 15 years before. And so Here's a good one for the kids. If you're building towards the future, if you're capable, remember that you can always buy the current. And that's how I thought about search. I was gonna master social in '09, and I felt like social was gonna eat up search anyway. And I think it's starting to happen now. Like, search is in a weird spot. Like, Google's in a weird spot. Like, in, in, well, it's in a great spot in some ways, but Yeah, I think search is definitely a different world. Like if your business, I actually spoke to somebody Thursday who is really getting hurt because he was one-dimensional on search. And I, you know, that's such a fear of mine that if you sell your stuff via email, via your podcast, via social media content, via search, you must develop into a Swiss Army knife because if you're just a fork, If you're just one-dimensional, you're gonna get caught.

Hey Gary, let me ask you about that. You, you were saying a second ago, you're like, I'm not afraid to go back.

Yes.

Do you, so like the way that I run my personal finances is I've got like, my safety net. So I've got this like account that has enough money that I'm good forever.

Same.

And, and so that's in Vanguard and bonds. And it says like, I've never touched that. And then anything, anything above that amount, I'll bet it and I'll start new shit. So you're talking about like, you don't mind going back, but it sounds like that's not exactly how you run your finances. So do you have like a safety net and then anything above that you're like, dude, bet it, bet it, bet it. Or do you just use profits from Vayner to make these bets? How do you, how does that work?

Yes. I have, I'm going to be uncomfortably transparent. My, I'm very fortunate. So my zero is $1 million, but that's it. That's it, Sam.

Wait, so you only keep $1 million in your, like, liquid portfolio? That's your safety net?

No, no, no. I have, I have other things, like I have money in all sorts of places, but I have this one place that has $1 million and literally everything else is in play.

Wow.

Now, Sean, I want to paint a very clear picture here because I don't want to create hyperbole. I haven't bet everything on everything, but if I ever feel the way I felt about Facebook in 2007 when I put I had $236,000 in savings. I put $200,000 into Facebook. Right? If that ever happens again, like, I'm willing to bet very large because that feeling, similar to the feeling I felt about the internet when I saw it in '95, similar to the feeling that I felt about Friendster, MySpace, that little like, oh, the internet's changing. I look for those moments. And again, I'm willing to go big. But to your point, Sam, it's not like I'll go to zero, zero. A million dollars is a lot, a lot of money. And especially if you're capable. If you're capable, I don't know, I feel very confident.

And your reputation.

Yeah, correct. I also think about face-off, where you change. I have these very deep, Sean, it goes back to wanting to win the basketball game. Like, I think it's more, I think the worst thing for my love of entrepreneurship that's happened is what Sam just said. I no longer can do it without anyone knowing. It's a whole different game. It was so fun when people didn't know.

What you're saying reminds me of, uh, well, two things. I think it's super interesting that your answer to what's the difference you've seen in the mindset and the psychology was who's willing to go backwards. And almost what you said was you almost kind of crave— there's like a romantic idea about going back, which I like a lot. I resonate with that a lot. It's almost like there's TV shows I wish I could go watch again for the first time in the same way. Like, there's no greater feeling than going from not making it to making it. Once you've made it and you try to make more, it doesn't have the same thrill, adventure, satisfaction, self-respect.

You know, you have to almost go into different games. Like, I I worry about that. Like, I don't, let me rephrase, I don't worry about it, but I sense that there's a day where I actually, I talk a lot about never retiring and dying at my desk. And then there's an equal part of me that realizes that I'm very wired in a way where I just might wake up at 79 and be like, you know what? Like, I'm done. I'm just going to focus on my grandchild's, like, Like I just, I don't know. I have like, I think we're all very, like, I think we underestimate how long life is. You know, I think we underestimate our capacity to make hard decisions to different directions that we can't see along the way. Then there's back to luck. And, you know, I mean, look, we've lived through a lot of prosperity. Everyone, the three of us have gotten very fortunate of where we live during what era. Right? Like there's a lot going on in the world. Like, you know, there was people in the Roaring Twenties talking shit like this over dinner and then, you know, a very challenging 30 years punched them in the face. Right? Right. It all seemed so great in 1927. America was on its way. It's going to be awesome. And then, you know, a massive world war and atomic bomb and Korea and Vietnam and social unrest. And so you know, all these things are like fun to think about. It's like fun to like romanticize about the future. But I will say this, I'm actually going to ask you guys this. What do you think your personal relationship is with gratitude versus taking for granted?

I changed on that once I actually sold my company and was financially free. And then like 2 weeks after the sale of the company, The CEO got into a life-threatening accident and I was like, oh, that could have ruined my deal. And like, like everything, like this all could have been ruined. And then I like hit like some threshold. I'm like, dude, I did not work any harder than anyone else who else, like who have done similar things, but failed. This is 100% luck. And I'm so grateful that I like, it just has worked in my way in many ways. I feel like I, I am the luckiest guy around and. It just seems like I'm so gracious for the luck that I have. It's, it's kind of, it's changed more to where I've just been gifted this and I, I'm so lucky and I'm thankful.

Good for you, Sam. Sean, where are you at with it?

I have a different, uh, so to me, I'm like, all right, I think people make a mistake. They're grateful in the macro. So if you say to somebody, you're like, what are you grateful for? Almost everybody, uh, my family, my health. And to me, this is the, I'm not saying they're wrong. Obviously those are great things, but it's sort of like when a company says our values are integrity. And excellence. It's true but not useful. It basically has me— leaves no register. And so I try— my focus is how do you be grateful in the micro? Meaning, can I be— if I'm in an elevator, can I find something in that moment? Can I get a rep, a practice rep of gratitude in that? Because that actually shifts me when I can take a breath, be grateful for the fresh air. I can look at something my kid is doing and how silly they are. And just in that moment, find something. And if I could do that, you know, 10, 15 times a day, that is, you know, uh, like the antidote, you know?

Yeah. I think that's how micro and macro and micro work together. I really do think of it as being alive. Like, just thank you for that. I'm not— that I didn't die last night, right? Like, I— and I, to your point, I think when your macro is that, I think you're actually— I think I love what you said. You're just talking about applying.

Yeah, that's how I apply it.

Exactly.

Right. That's my relationship with it.

Yeah, that's right. But like, if you're getting to that place, that's how I live. I'm like, like, literally, like, it's like a nice sunny day in New York today, and I'm just like, yeah, that's awesome. You know, like, like, just choosing positivity. Like, I think people have been so sucked into, like, focusing on what they don't have or what, what's not going well.

Naval has an amazing definition of happiness, by the way. I don't know if you've ever heard this. He goes, happiness is what you feel when you don't feel like anything's missing in your life. Right? People think happiness is something you got to achieve, something you got to go create, something you got to get. It's like, you know, you think you need to accumulate things to have happiness. And he's like, actually, it's just when you're not focused on what's missing.

Well, that's right. I think, I think simplicity is just so fucking, fuck, man. It's so right.

But you don't, your, your, your life is not simplistic. Uh, I mean, I don't, I don't know what your personal life is like. I don't know if you have multiple homes and what you own, but your professional life is not simplistic.

I'll tell you why it's simplistic. I'm not attached to my professional success or who I am. I'm in a very weird place with my winning and losing and my Gary Vee of it all. I care so much, but it's a game. My professional life is a game. I don't want to be unhappy. I fight for happiness too much, and I think it is in the simplicity. You're right. The day-to-day is chaotic. There's meeting after meeting after meeting after meeting. But I like it. I like juggling 17 balls and I'm not upset about the 13 that fell on the ground and broke. And more importantly, I'm not worried about the people who are watching me juggle boo when the ball breaks. That I think is massive.

Yeah.

But when Theo Von makes fun of you, it's pretty hilarious.

That is like the ultimate, like, because I love Theo. Like, like to me, back to like where we came from, Sam, I'm like, my God, like I've gotten to a place where someone as epic as Theo Vaughn or any other comedian, Tim Dillon, like I love these guys. I'm always fascinated when people struggle with a comedian razzing. Like, I think it's like, you've, that's like such flattery.

Yeah, that was awesome. It was awesome. I saw that. I was like, oh, the guy I look up to, he's, uh, he's crossed over to mainstream. It's awesome. Um, Sean, what were you going to say?

Well, I want to ask two questions. One, Uh, you showed those stock certificates on the wall. Speaking of winning, uh, I saw, okay, you invested in Twitter in '09, Slack pre-IPO. I think the Liquid Death guy used to work with you, work for you.

Yeah, literally worked at VaynerMedia the day before he started Liquid Death.

Facebook pre-IPO. I'm curious, what was, what investment was the best investment for you? What paid off in terms of, you've made a bunch of bets, right? And that, those are the winners.

Facebook. I haven't sold one share yet.

Oh shit.

That's insane.

But that goes back to— that goes back—

insanely good.

Yeah. That, that goes back to jockey over horse. I tell all my friends like who get into investing, I'm like, man, they're like, what have you learned? I'm like, what I've learned is when I only invested in the person, when I'm, when I, I've hit this new state where like I'm really trying to be obsessed with the person and the idea. And if either one isn't like an A+, then I'm like, eh, right?

You said and or or?

And, right?

Okay. Jump the and the horse.

That's right. But if I or it, fully person, not idea.

What year did you do that? Did you do that deal?

Facebook? I thought 2007.

Oh my God. So, I mean, I don't even know what that— you'd be up 400 times. I don't know. I mean, a lot.

A lot.

100x at least. I want to get your rapid take because I know you've— one of the things we do on this pod is we kind of, we love anecdotes and also little insights on people that we think are wired in an interesting way. Maybe not even the way we want to be wired, right? Like Elon's really interesting. We don't think he's perfect. We think there's a bunch of things he does that are cringe. We think there's a bunch of things he does that are epic. So I'm curious, you've bumped into or have studied or have an opinion on any of these people. So I want to go rapid fire. See if you have something, Give us, give us like either an opinion or story.

So yeah. So is this from outside observation or if I met them inside observation?

Either one. Or if you have nothing, you could say pass. I don't have anything on that. All right. So first one I want to do is Zuck. You've talked about Facebook and the jockey. Give me Zuck.

Dude, I think he's uncomfortably underrated. Like he's the only person that I met back in '07. Like in this era now, I think it's getting more obvious, but he understood attention. He literally tried to buy Twitter. He bought Instagram. He bought WhatsApp. He tried to buy Snap. He just understood attention was the only asset. And he's so nice. He's a nice kid. Like he's just a very simple, nice kid. I'm happy with the way things are going for him a little bit right now. Like people can see how like doofy he is. Like you see him like in the corner of the UFC thing and you're like, this is just a nerdy kid who's like, you know what I mean? He doesn't give a fuck. Now, people will think it's because he's got a trillion, but like, it's just, he's just like a dentist's son from Connecticut. Like, he's just a fucking nerd with no bad intent who fucking spent his childhood coding, which put him in a position, right? He put in the hours. I'm a fan, man. I think he's a very good operator. And the reason I've never sold a share of Facebook is I've been committed for a long time in this in my own mind, which was I'll never sell until he's gone.

Logan Paul.

So do you know that Logan Paul was starting to emerge very little on Vine when VaynerMedia for Virgin Mobile did a campaign called Finding the Next Vine Star?

You guys kind of discovered him, right? Like when he was, I think he had like 15,000 or 18,000 followers at the time.

It was crazy. And full, by the way, full disclosure, Jerome Jarre, who was one of the 10 most followed people on Mine, who was my partner, Jerome and I launched the first influencer agency called GrapeStory back in '13. He was the one who said, you know, he let me pick from 3 people. I think all 3 of them got big. But I think Logan is, you know, he grew up in the limelight, right? You think about like what happened in Japan or all this stuff. Like, it's tough. These kids are, you think about child stars when we grew up. We all knew that like child stars would be fucked up, right? And now I think like everyone's going through that. The limelight is hard. So I think Logan is well-intended. I think he's very entrepreneurial, like very entrepreneurial. And I've always thought of him as like a Marky Mark or a Fresh Prince or The Rock, meaning I always watched him from afar. And as I got to know him a little bit, I was like, okay, this kid is Logan Paul today, just like Marky Mark was Marky Mark before he was Mark Wahlberg, just like the Fresh Prince of Bel-Air, you know, what Will Smith was before he was Will Smith. I've always thought that Logan would cross over and he has obviously with WWE in a lot of ways. And I think that will continue. Like if you told me Logan is like an action star and it's like at the, like the way John Cena was at the Academy Awards last night, like Is Logan doing that in 15 years? I'm like, that makes sense to me. That's how he's wired.

Sam, he's only 28. He's, he's only 28 years old. The dude basically like, you know, when he's 14 or whatever, like, won. He won in the social media game.

Now he—

and then think about the pivots, right? Both him and Jake. But the thing about the pivots, now he's got Impaulsives. He's got the podcast where he's super chill. It's the opposite of crazy Vine prankster guy. He pivoted to like He's the guy asking questions. He's inquisitive. He's curious. He's got like, you know, the popular podcast goes WWE, becomes a champion in WWE, creates Prime, which is going to make him a billionaire by the time he's 28, 29 years old now, because Prime is probably going to be worth tens of billions. You know, they did, I think, $2 billion in sales last year.

I mean, I'm in this world like Prime is definitely like a 2 depending on the time they decide to trade it. It's 2, 3, 4, 5, 6, 7 $7 billion.

That high? $7 billion?

I understand.

I talked to MrBeast and he was like, $20 billion is where Prime is going.

Like, that would be very, very— I mean, that's like, look, I never underestimate Jimmy's foresight because he's great. I've known him a long time. But just being in M&A at CPG levels, my intuition is that they won't be patient enough to get to that big of a number. Right?

Like, well, the beauty is they're not operating. The other guys are.

They got the other guys operating. Yeah, they're pretty young too, though.

Yeah. And more importantly, shit, like I said, shit changes. Like everything's hahaha until it's actually in front of you. It's all kicks and giggles and we're going to 20 until you fly to Atlanta and Coca-Cola actually offers you 5.9 and you've got to sit there as KSI and Logan and those guys and say, okay, if we say yes, because you know what they're going to say, you guys are like this. So you're going to really understand what I'm about to say. You know what they're going to say? They're going to say, huh, we can do this right now. And then in 24 months, start a new thing, a shampoo or a deodorant and sell it to Dove. Like, so I think it's, it'll be interesting to see how long they hold their breath. And don't forget one bad year. You guys know this, how businesses work. One bad year takes a lot of leverage off the table in a negotiation. And so, you know, they'll be thoughtful about that because no matter what you are, once you saturate distribution and don't forget, they're selling on something that's more like Supreme, right? They're selling on cool.

Cool.

Yeah.

Right. Kids are buying it literally to drink it for the status symbol, like a fashion brand. And that can only last so long. Z Cavaricci's were only cool for so long.

Those are the fucking Z Cavaricci's. That's the point. Me and you have no fucking clue what that is.

Sam, that Z Cavaricci reference was for all the Jersey boys that grew up in the late '80s, early '90s. People will Google it. They were the hottest jeans, pants. If you didn't wear your Steve Cabaretti jeans, you were nothing. I didn't have them, by the way. I was having a great life, but they were fucking it.

He's compared Prime to JNCO jeans. What were you going to say, Sean?

Well, I asked you a bunch of names that are basically names that people know. I'm curious, who do you think is dope? Who are you learning from and who are you kind of admiring? Who do you admire? Who do you learn from? Who are you inspired by? Because, okay, a lot of people are inspired by Gary Vee. Um, who's Gary Vee inspired by?

That's a great question. I'm a little weird on this one, but I'm glad I brought up, uh, Break the Web. I'm like inspired by the collective more than an individual.

The field.

Yeah, I love the field, brother. I, I, I just like, I spend almost all of my time on the collective, so I don't even have the allocation of time. I also am very inspired by the following person. Show me the person that's currently living through massive adversity. Like somebody's listen, I'll tell you somebody who's 10 times more inspiring to me than I think I am or deserve to be to others. Show me the kid that's listening right now whose father passed away from a stroke. He's 16. He's got 3 younger siblings and his mom has to now work 2 jobs and he's holding it down for the fam. Right? He's literally a sophomore in high school and he's basically the father figure now for 3 siblings. He had to quit the fucking football team because he's also like, like, I, I'm the son of 2 parents who lost a parent before they were 15. And it drew, and back to gratitude, I think I got really fucked up by being scared that my parents were going to die my whole childhood, but it kind of converted into this gratitude framework that's insane. It makes me unstoppable. You know? And so, yeah, for me it's less Bezos or Elon or, you know, Oprah or anything. It's much more like someone none of us know that is really in it.

That bodega owner energy.

That stuff I grew up with and I fuck with it. But that person I think has it lucky back to earlier, our simplicity, like owning your own little business, living within your means, like that's fucking kind of chill. It could be really epic. It doesn't put you on like this podcast, but it's like a great life in a lot of ways. And I see it a lot. I lived it, what, building my dad's business from 22 to 34. I not that person, the one that's like, back to your point, Sam, the spin of the wheel really created real adversity. I'll say it again, and not a peep of complaining. There's a very small group of kids that get that. And they just convert into leader instead of woe is me or rebelling. I admire that level of tenacity and grit and accountability and fucking like, fuck it. Like, this is— I got this. This is— it's on me. I gotta put this shit on my shoulders. I'm gonna do this for my 3 siblings. Like, I admire the fuck out of that kid.

I had a— I wrote down a quote, uh, when I was doing the research for this that I think is, is exactly what you're talking about. You go, Forget rags to riches. Some people are just rags to rags just so that their kids have a shot at rags to riches. And I respect the shit out of that. I love that quote.

Yeah, man. Thank you for finding that. I really, man, I'm really affected by that. Like Sam really hit it on the head. Like I hate the word luck because I think that people weaponize it against people that have worked really hard. But I, but I believe in serendipity and luck quite a bit because it's just the way, like I was born in the Soviet Union. Like I got lucky to get out of there when I did. If I didn't, I would've come to this country in 1991 when it fell. I would've been 16, 17. I'd sound like Ivan Drago on these podcasts. I like, it would've been all different. And you know, I just, I just really do admire people who, I really do think entitlement and lack of accountability has become a disease in first world countries in 2024. And I just really admire people who play the other way.

We appreciate you doing this, man. You got Day Trading Attention coming out, I think, on May 21st, right?

That sounds right.

You're the man. We appreciate you hanging out.

Thanks for coming on, man.

I got to jump to this board meeting. I appreciate it.

All right. Take care. See ya.

Love you guys. Good luck.