#80 The Biggest Bets I Made — And How They Paid Off: Gary Vee

9 Jul 2025 · 1 h 21 min · 25 chapters

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In short

Gary Vee (Gary Vaynerchuk) discusses his biggest bets and how they paid off, how he evaluates founders, and what it takes to build and scale businesses long-term. He also covers merchandising/content strategy, community management, and why outside validation and “flexing” undermine sustainable success. He shares AI-related predictions (including that many people’s grandchildren may marry AI robots).

Guests (and hosts)

Cody Sanchez hosts. Gary Vaynerchuk is the guest; he’s a multiple New York Times bestselling entrepreneur/investor with nine-figure businesses and decades of social media trend prediction. He describes investing early in Facebook, Twitter, Tumblr, and later backing companies like Uber, Snapchat, and Coinbase.

Key claims

Scale comes from “10, 80, 10” (deep involvement early, disappear in the middle, return to close). Winners focus on “dirt and clouds” (execution and feeling). Most people chase trends for validation, not love. Parents shouldn’t bankroll adult children (after ~22) because it signals lack of belief. Community management (replying to DMs/comments) is “scale the unscalable.”

Notable examples

His early investment wins/losses (Yo Bongo → Tinder as a missed founder analysis). “Dollar rack” merchandising at baseball card shows. Abandoned-cart tracking in early ecommerce. Replying to everyone on Twitter (2007–2011) as a growth tactic.

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Chapters

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Episode Discussion

0:00 to 14:00
“This episode is brought to you by Google Chrome.”

Materialism and Parenting Struggles

14:00 to 19:15

Gary Vee discusses the complexities of modern parenting and societal pressures regarding materialism.

“So, you know what people struggle with everything I say.”

Materialism and Parenting Struggles

19:18 to 19:41

Gary Vee discusses the complexities of modern parenting and societal pressures regarding materialism.

“It can help you with practically anything on the web, like restoring a vintage motorcycle from a 50-page restoration block, or finally break down that long article you've had open for weeks.”

Early Business Lessons from Childhood

20:10 to 28:00

Gary shares insights from his childhood entrepreneurial experiences and how they shaped his work ethic.

“Like, thank God for me, I loved my parents so much.”

The 10-80-10 Framework for Business Success

28:00 to 30:00

Gary Vee discusses the importance of focusing on key aspects of business management with his 10-80-10 framework.

“I think the dirt and the clouds are the only interesting parts of the game.”

Young Entrepreneurs and Validation

30:00 to 32:20

Gary Vee reflects on the challenges faced by young entrepreneurs in seeking external validation and the importance of self-awareness.

“What do you think that young entrepreneurs are sleeping on right now?”

The Journey of Building a Business

32:20 to 34:20

Gary shares his personal journey of building VaynerMedia and the importance of patience and passion in entrepreneurship.

“And my gym, my eating discipline, my doing things around the house, these are fully procrastinations.”

The Realities of Entrepreneurship

34:20 to 36:40

Gary discusses the harsh realities and statistics of entrepreneurial success compared to societal expectations.

“It's like Vayner3, VaynerSports, VaynerRSC, VFriends, which I think is a different entity.”

Challenges of Modern Parenting and Education Systems

36:40 to 42:00

Gary critiques modern parenting and educational systems, discussing how they affect children’s preparedness for the real world.

“Well, yeah, there, you know, this most people, this was a real wake up call for me when entrepreneurship got cool in like the mid two tens, like 2010, 11, 12, 13, everyone started running towards it.”

The Merit of Sports vs. Business

42:00 to 45:20

Explore the differences between success in sports and business, emphasizing meritocracy.

“I have a 15, 12-year-old, 16 now, and 12-year-old, like, growing up in this last 7 to 10 years, parents want to go on the field and kick the ball for their kid.”
Show all 25 chapters

Building Brands from the Ground Up

45:20 to 48:20

Gary Vee discusses strategies for building brands and businesses from humble beginnings.

“And so with your current knowledge today, I'm curious, like, let's say you had to go back, back to your wine days, almost.”

The Importance of Content Creation

48:20 to 51:00

Learn why content creation is essential for small businesses and personal branding.

“traffic to your business, average receipt size is to run, if you're a local business that people come to, is to run 10 mile radius Facebook ads.”

The Importance of Content Creation

51:01 to 51:51

Learn why content creation is essential for small businesses and personal branding.

“Remember, just make sure that you're always executing and they are spending their time calling you things.”

The Importance of Content Creation

51:54 to 52:11

Learn why content creation is essential for small businesses and personal branding.

“It can help you with practically anything on the web.”

Dealing with Haters and Competitors

52:47 to 56:00

Discuss strategies for managing criticism and competition in business.

“I was just about to say, you know, we're starting to get to know each other.”

The Importance of Competition and Passion

56:00 to 58:07

Learn why competition and passion are vital for personal and societal success.

“Teaching a young kid nothing matters is a dangerous game.”

Finding Great Talent in Business

58:07 to 1:00:06

Discover strategies for identifying and evaluating talent in a digital landscape.

“But the number one of the biggest questions I get asked by business owners in our portfolio is how do you find great talent?”

Live Social Shopping Trends

1:00:30 to 1:02:36

Explore the growing trend of live social shopping and its impact on commerce.

“It's just 10 years later because shit changed.”

The Future of AI and Commerce

1:02:36 to 1:09:57

Understand the transformative potential of AI and its future implications for society.

“Like, you know, like people love an excuse, right?”

The Rise of AI in Daily Life

1:10:00 to 1:11:12

Learn how AI is revolutionizing shopping and decision-making.

“And I spend a lot of time prompt engineering, you know, just if you don't know what that means, Google it or AI it.”

Harnessing AI for Personal Growth

1:11:12 to 1:11:55

Discover practical ways to integrate AI into your daily routine.

“AI is answering that question for me so that I can go look at those apps and understand what's happening.”

Investing in AI: Caution and Context

1:11:55 to 1:13:10

Understand the risks and rapid changes in AI investment.

“The reason I haven't yet is every week, you think you just invested in the best X and a week later, somebody crushes that.”

The Future of Human-Robot Interaction

1:13:10 to 1:14:48

Explore the implications of developing emotional connections with AI.

“It makes me, uh, it makes me understand that this is how it's always been.”

The Evolution of Humanity and Technology

1:14:48 to 1:17:05

Discuss how technology alters human behavior and societal norms.

“Like 40, 50 year old men and women like you and I.”

Embracing Technological Change

1:17:05 to 1:17:52

Reflect on society's resistance to new technologies throughout history.

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Transcript

Automatic transcript. May contain errors.

0:01This episode is brought to you by Google Chrome. You think you know a browser, but Gemini and Chrome, that's new. It can help you with practically anything on the web, like restoring a vintage motorcycle from a 50-page restoration block, or finally break down that long article you've had open for weeks. Gemini and Chrome is here for it. Ready to make anything online make sense? There's no place like Chrome. Check responses set up required. Compatibility and availability varies 18+. I think the dirt and the clouds are the only interesting parts of the game. If you don't know Gary Vaynerchuk, well, you've probably been living under a rock.

0:33He has a multiple New York Times bestseller. He has multiple nine-figure businesses. People ask me how I scale Vayner. 10, 80, 10. I open and close. So the truth is you need to be an absolute freak of nature. You have to have outlier behavior. Do you know how fucking hard it is to make a million dollars a year? How do you know what characteristics a great founder has? Very early on in my career, I was unstoppable. Facebook, Twitter, and Tumblr were my first three investments in my life. I went on pure intuition. What are your craziest predictions when it comes to AI? My craziest prediction is that most people's grandchildren will marry an AI robot.

1:05I had an epiphany. I was like, fuck. Welcome to the Big Deal Podcast. I'm Cody Sanchez. And today we have a man who is not only able to predict the social media trends of today, he's been doing it for the past 30 years. He's got an audience of millions every single day listening to him about how do I go viral? How do I build big businesses? What is going to happen in the future? And today we get into stuff that he's never talked about before. But what I think is most interesting about what we talk about today is he's going to make some predictions on what's going to happen with AI for all of us.

1:42He is going to tell us the secret place to find underpriced attention. So how do we get more money into our businesses by double tapping on this? And he's also going to hit you with what I consider to be like, I don't know, an adrenaline shot level of intensity about why to keep going, how to keep going when things get hard and what it takes to be a business owner that survives over the long term. Gary Vee is somebody who's become a friend of mine over the past year. And listening to him talk about things I've never heard him speak about before on the Internet was really a true pleasure. So I hope you guys have as much fun as this one.

2:18I'm going to listen back to it because I want to build businesses as big as this man did. Without further ado, Gary V. Because when I was looking at your investment, Rolodex, holy hell, you have invested in some giant company. I don't think people know half the things about you fully on the internet, but like Facebook, Twitter, Tumblr, Uber, Snapchat, Coinbase. I mean, I could go on and on and on. So how do you smell like a founder that's going to win? How do you know what characteristics a great founder or CEO has? Very early on in my career when I didn't consider myself an investor, I was unstoppable.

2:50Facebook, Twitter, and Tumblr were my first reinvestments of my life. I only judged what I smelled. I went on pure intuition about the human and the thesis. I wanted to like the idea. And they were far enough along. I wasn't an angel round. They were a little further, more an A or pre-A. Then I thought I was a hero because I was red hot. and I started to like read TechCrunch and spend time in Silicon Valley and I got caught in an era, a three-year era where I invested in just the idea and I thought if I, what I didn't realize at the time, what I was doing is, oh, this is a good idea and I knew how to run it.

3:33I put myself into the CEO chair, started spending less time analyzing the person, went through an era of ideas and I lost. I invested in a company called Yo Bongo that basically became like basically two years later an app called Tinder came out and was Yo Bongo I loved Yo Bongo but the kid was a young kid and I didn't spend enough time analyzing his stomach, his merit and this was the explosion of like smart kids and engineers becoming founders and Sean is an animal the founder of Tinder and so I I, but Sean, that was like two years later, Elliot, I think that's what his name was, like, I didn't analyze him.

4:18So what has worked for me? What has worked for me now when I try to think about it, I think about do I like the jockey and the horse, right? This hat that I'm wearing, Seguilman Stables, right? Max and Caro, you know, they're a couple and they're a team. I love them. They're gangsters. They've got it. and I, in the world of Kith and Rude and Palace and Jerry, fear of God, I understand the business of when you're the hottest up and coming fashion brand, it's a business. You know what I mean? You can get to a nine figure exit from a LVMH or da, da, da. So, you know, I'm looking for the jockey and the horse.

5:05Now the jockey being the entrepreneur, the horse being the business. I need to like both and understand both. So say I'm sitting across from you and like, you're either going to hire me or invest in my company. What are you, what are you asking me to tell if you like me or not, or want to take a bet on me? Usually here's how it goes. I'll go with, Hey Cody, start late. So nice to meet you. I'm so excited about this. Tell me everything. Literally. That's what I will say. Tell me everything is kind of a goat. It's not like my go-to question. It's just what I happen to think. It's what I happen to mean.

5:35Tell me everything like as much as you want to tell me either about yourself or the business go I listen carefully and then my series of questions is predicated on what I listen to I'm counter punching the reality of what I heard I don't have a go-to other than I need as much context as possible from you right now about you or it I'm 49 have been pretty much successful in anything I've I've run and have had plenty of winning and losing an investment I can listen and know where I want to go sometimes after that code it's over like even off the rip right like it's over because you know at this point I have such a public life too like I can feel when someone's pandering to like well Gary I love the hustle and the grit and I love flipping you know I can tell when someone's trying to game me and then even if they're trying to game me I won't even like that doesn't eliminate him.

6:27That's just a data point. Right. Again, because I'm now 49, 22. So for 27 years, for 27 straight years, every day of my life, I have had to be responsible to make payroll with no funding. 27. Like I'm a real actual operator. And so it's very easy for me to ask questions. You know, how fast can you tell? Sometimes immediately. It's like, you know, like many of us listening know what love at first sight feels like, right? Or crush at first sight, everybody knows, uh, or like immediately knowing I'm incredibly intuitive. My emotional intelligence is disproportionately my go-to. Uh, so I can tell right away.

7:19I can't tell right away if I'm going to hire someone or invest or if someone's a genius, I can tell right away the things I'm feeling like this is potentially someone remarkable. I can always tell when someone's just an average C player right away. You know what I mean? Pretty quickly. But again, C players for my businesses when I hire, I love a good C because I think we have a system to get people to Bs and I think Bs are great. Interesting. So you are okay with B and C players. Let's talk about that actually i think most companies when you're at scale need plenty of b and c players a players are always looking to find that though then because it's like you don't want to have a a culturally toxic no that i mean what's the difference by the way i think my five posts ago on instagram is give me an a plus personality and a c player because c personality is death on a rival C let alone DNF and there are plenty of those people no I'm talking about like you know brain power you know like like firepower right like not everyone's the sharpest fucking most you know like like it's just real life um work ethic you know work ethic you can't really tell in an interview I feel like work ethic's one that you can see more play out and then you decide I just think that we in my companies care to level people up and we continue to get better at it and that's really working for us at scale so I have a lot of retention um but yeah I think I think I'm looking for firepower intellectual firepower personality traits um I'm trying to poke at like self-awareness I look for humility I'll give you one that is always uh let down hey Cody I'm super excited about this you know you're going to come in and be at a VP level at Vayner which is a big role like you're actually like I think the VP director role at my company is really running the companies above the SVPs and the C-suite you know we're in an interview I'm saying that and I'm like code real talk like don't bullshit I'll say like this hey real talk don't bullshit me because I'm going to find out anyway and I want you to be here a long time and I want you to win here give me one of your shortcomings in your career when people go to Gary sometimes I care too much and I like that I'm like it's over you know what I mean like give me something real please you know what I mean like it's why too hard it's like why when I realized you know five to seven years ago that lack of candor which is crazy because Gary B's candor is off the charts but Gary Vaynerchuk the executive when I realized lack of candor I struggled giving critical feedback yeah and then the firings would be sloppy because of that because people would be surprised when I really had that moment in the mirror with myself what am I maybe 49 maybe 42 43 44 when I had that moment literally the next day I started putting it out publicly that's when I wrote 12 and a half because I want I literally wrote an entire book because I wanted to put out there my shortcoming of candor.

10:32Which people probably like almost don't believe because. Correct. Because my strength is candor as a public figure talking about things. But Gary Vee and Gary Vaynerchuk, I'm the same. I think, you know, one of the things I always smile about is when people work for me or get to know me, they're like, it's so cool that you're. I'm the same, but it's a different context. Yeah. You know what I mean? like I'm talking to the blank world right now versus someone who's worked for me for three years here's where my bleeding heart becomes a vulnerability you stink at Vayner for the last six months it's now a problem you've been there for five years you've given it all you've always really given it all it's a problem we're leveling up it's a problem people around you are fucking pissed you're not good enough you're getting paid more than people that are better than you underneath you it becomes a problem but I know because I'm so HR oriented but I know that your dad has cancer.

11:25And I know that you just broke up with your boyfriend and I'm struggling to fucking fire you. I don't know what else to tell you. It's fucking hard. The end. I don't know what else to say. Never feels good. It doesn't. But, but I think also, you know, one of the cool things about you is, um, you are so big. You've been around for so long publicly that also the tough part is sometimes, you know, that's the person that's coming in and firing you, or that's the person that's giving you the critical feedback. It's like this extra fucking layer on top of everything else. You'll appreciate this. I love you for that.

11:58You're right. For some, at 22, at 26, at 29, at 31, at 34 in the wine store, when nobody on earth knew who I was, it was my biggest weakness. Yeah. Interesting. So still always the same. I just, I just, there was a level of confidence slash potentially ego. I always thought I could make it better. Like I definitely, definitely would have been the girl that would have went after like fucked up dudes because I thought I could make them better. I would have definitely been that girl. A hundred thousand percent. I know it. Like I'm gonna fix him? Yeah, and not like in a fucked up way, in an optimistic way.

12:32Not in a like, I'm a psycho. In a, you know, and the problem for me is I have. My problem in a lot of ways is there are many people within my organizations, startups, friend groups, boards I'm on, because I'm so into guidance counselor, coach, therapist energy. And I have such a yin and yang because of the emotional intelligence, but because of the operational and because of like just wanting to kind of do to the world what my mom did for me. I've been successful at it. I'm just like names are running through my head right now where like people started off at like a three emotionally and are at an eight strictly because I put my fucking hand on their shoulder.

13:17Every teacher, therapist, coach, guidance counselor knows what I'm saying right now. And you know how rewarding that is? Like I've changed the course of this human being's life. I'm doing that with content to the world, let alone imagine someone I can put my hand on their shoulder. So it becomes intoxicating in like, it feels good to help other people for certain people. I know many people don't feel the way I feel, but for me, it feels good. I like it. It feels like the right thing to do. What is the opposite of that? What is like the advice that you keep having to repeat that you know people need to listen to and they just don't all every single by the way every single thing i say patience like insecurity don't keep up with the joneses fuck materialism eat shit like it's both the left and the right struggle with me and like me right because because in one side i'm like compassion and all the feelings and everyone's like ah on the other side i'm like kill every fucker it's all competent like like because it is purple because life is purple the reason there's so much tenseness right now is the world the youth the elderly the left the right the 40s that every generation z x y boomers alpha we're fighting for it's red or it's blue i'm like motherfuckers it's purple you fucking idiots.

14:41You fucking idiots. It's fucking purple. How the fuck don't you understand that? So, you know what people struggle with everything I say. You know, when I tell parents that you got to stop giving your kids money after they're 22, every 20, every parent right now listening, who's got a 27 year old on the payroll doesn't like getting poked like that. But I'm in the receiving end of all this fucking depression DMS from 28 year olds that are on the payroll. because parents don't realize if you're paying for your kid when they're a grown adult, you're telling your kid you don't believe in them through your actions, not your words.

15:19They know they're a loser. Yeah, that shit hurts, you know? So what do the parents say to you when you say that? Like, what's their excuse for continuing to do that? You know, in the most private conversations, it's it's just service level justifying you know like oh you don't know my son like he had this issue I'm like everyone had issues do you understand every person in the 80s in New Jersey got bullied every single kid I grew up with got bullied the popular ones like we've started making these words so big I told somebody yesterday don't use the word anxious you're not you're inconvenienced you know like like we've now just gotten so deep into this shit this is why so many people are struggling we've given them permission to not do and fight and fix oh that's i've never said it that way we have given people with all these big words do you know what imposter syndrome is It's called insecurity We've just given it makeup Nobody's like yo I'm insecure Nobody says that code But so many people are like Man I have imposter syndrome Makeup Got it?

16:46The definition Literally the definition of imposter syndrome Is slang for I'm deeply insecure But nobody comes around And says I'm insecure But everybody I have anxiety People say they have depression when they don't. And that fucks up for people that actually do. I feel bad for the people that actually do. It's a great point. And it's confused everybody. Everybody, like, do you know how bad I feel for all the people that own big businesses? Who, like, every person's like, I need a mental health day. And they're, like, starting to cancel mental health days. And meanwhile, of the hundred people that are abusing it because they just want to play video games are doing fucking nothing.

17:27Because I live that life. do you know how many sick days I had from 1982 to 1994 a million I tried to get out of school every day and boy when 5th grade Gary found out that legally they had to send you home if you went to the nurse and weren't refusing to go back well I fucking cooked I mean that was everything to me that discovery I don't know if I've ever been happier in my life in 5th grade somehow I don't want to bullshit I don't remember how but I learned that you could actually will your, you could just stick in. If the nurse said, go back to class, you're like, I don't feel well, that if you kept going, they had to send you home?

18:07I mean, I didn't, so I - Did you share immigrant parents beat your ass for that? Well, it's funny. This is why I put my mom on a super pedestal. My mom knew that getting A's in school was not going to lead to my success and happiness. And she did something most parents weren't willing to do and are still not willing to do. And she didn't give a fuck fuck what everybody thought about my D's and F's. Got it? She knew me. But is that because somewhere else you were showing her obsession? Of course, of course. Because if you were a parent that just was like D's and F's, fuck off, that would be. She's the same lady that looked at me on my 14th birthday and said, you know how you suck at school?

18:45I'm like, yeah. She's like, now you work. I was 14. 14 code. I like her. Like I worked every weekend, every summer. My last childhood moments, like childhood, ends in eighth grade. There was no fun in high school for me. There was no, like, I worked because I had to pay the consequences of not working in the classroom. Thank God for me, work was my nirvana. This episode is brought to you by Google Chrome. You think you know a browser, but Gemini and Chrome, that's new. It can help you with practically anything on the web, like restoring a vintage motorcycle from a 50-page restoration block, or finally break down that long article you've had open for weeks.

19:29Gemini and Chrome is here for it. Ready to make anything online make sense? There's no place like Chrome. Check responses set up required, compatibility and availability varies 18+. Hey Chicago, class it up with Crocs. You know back to school is coming in fast. So why wait to find your new fave footwear? Step into a local Crocs store and step into your new look. Try it. Style it. Make it yours. Because the right pair doesn't just show up. It shows off. First day fits, handled. Walk out ready for whatever's next. Visit your nearest Croc store today. Like, thank God for me, I loved my parents so much.

20:13Thank God for me, I knew, I knew as a teenager that I had it. Because I was doing baseball card shows at 11 and 12 and grown men. You know, this is why I love, like, that's where I was getting validation from. In school, I was getting D's and F's and grownups were telling me I was going to be a loser. Teachers in the 80s didn't fuck around. I had teachers like Dr. DiBella in Martin Luther King Elementary School in 1987 said I was going to be a fucking loser. Makes you feel any better. My math teacher told me Helen Keller would have a better shot of winning an archery contest than I would have been in finance.

20:50Oh, my God. 100%. But God, what great fuel. Honestly. Oh, man. Pretty thankful. Yeah. But then I was doing baseball card shows at 13, making$800, while the grown-up to the left and right at my table were making$300 because it was a crappy show. And my mom picks me up at Sunday night to, like, pack up and drive me home. And I've got two 30-, 40-, 50-year-old men telling my mom, like, your son's a genius because I was doing all sorts of weird shit that nobody else was doing. And so, yeah, I mean, I just, that was. Like what? Like the dollar rack, like I was, I was selling like 50, 60, 70 cent and dollar,$20,$30 cards that you can't move those cards.

21:32But because I merchandise them as a dollar rack with a huge sign, everybody just stopped by and bought cards. My friend, my friend, Brandon Warnicke, who's still run in my life. We met at 14. We did baseball card shows. He runs the wine library. I talked to him every day. He's one of the few humans on earth. I talked to every day. I mean, he was baffled by the dollar rack when I put it out. He was like, that's not going to work. And then like three hours later, there's not a card left in the dollar rack. Merchandising matters. Explain what that is to somebody who doesn't know what merchandising is.

22:03How a human sees it on the other side. When you walk into like, you know how like some of you like, it's very simple. It's like, think about the best way to describe merchandising is to describe to everybody their home. Some of us, like me, are comfortable in slobbery. You know, crap on the floor, room doesn't smell. I mean, I was a fucking cliche dude, right? Like laundry on the ground, like room smells like shit, like things everywhere, like who gives a fuck? Like don't even do laundry. Like where to sit in my teenage, oh my God, such a dude. Other people can't even fall asleep in their apartment, in their like room, unless the fucking scent is perfect.

22:43Everything's perfect. Like good. So like, like how something shows up for you. I get excited walking up to a garage sale where shit's all over the place. But let me take a different angle on it. So that's the setting. Now imagine like why are you grabbing something when you buy? Like I always ask myself after I do it, why did I just pick that up? It's on the end cap. It's at the register. That sign, the presentation. By the way, merchandising is the fashion industry. You know, like presentability. but like what compels someone to grab an item? That's always what I thought about. The sign, the positioning, the location within the store, the eyesight level.

23:30Do you understand that retailers like think, like I think like a retailer, like what's at eye level is what sells. Bottom shelf doesn't sell. When I used to get mad at a supplier if we didn't have like good negotiations or like they weren't supporting us, I took their most important products and put it on the bottom shelf. Merchandising. You know, I obsessed when I was 15. I used, when I was six, 15, 16, I was allowed to go upstairs. Before that I was downstairs in the warehouse. And when I was at the register bagging for the cashier, which is what I was doing. And then I became a cashier at 16.

24:04I could see how people walk based on where my dad's registers were. I could see people walk in and we were slow. We're still local store at that point. I would watch every customer. They'd walk in. what do they grab why so it's presentation how your tables laid out how it's it's why i was good at ui and ux when the internet came along all the designers in 97 98 99 2000 were like yo you're really good at this because i thought like a consumer like why would they click that button what about below the fucking scroll what about this checkout i literally had you know uh empty cart or like uh lapse card or or whatever it was called what the hell is it abandoned carts i I remember going to my developer in 2000 being like, can we see who didn't check out?

24:52Like, I like, it was like, you got to understand this is early internet. Yeah. It didn't exist. Like, because you're thinking in the store, Hey, that guy's walking out. Like, sir, did you not find something? That's what you would do. That's exactly what I would do. So I was like, is there an internet? Wait a minute. There's no internet version of this. I'm like, Eric Kastner, big shout out to him. Eric, can you see in the code? Like, I don't even know what to call it. The code, the server, who the, we used such funny words back then. He's like, yeah, we started emailing people that had abandoned carts and fucking crushed.

25:21So like, you know. Merchandising is, it's so funny because the other day I went to, this was two days ago, I went to the Harry Potter store here. And the reason why, same thing you said, who's better at merchandising in the fucking world than the entertainment space? And I think arguably Harry Potter, probably one of the best of our lifetimes, right? One of the incredible IPs that we saw birthed. Exactly. And when you walk into that store, it's always packed. Packed. And it is huge margin. It's incredibly well designed. And like they rotate merch, but what I've kind of noticed is they don't rotate it that much.

25:55Yeah. Like it's not like they always have to have some new - Are you a huge Harry Potter fan? I'm a big Harry Potter fan, but I'm not crazy about it. You're not crazy, but you're very solid. Yeah. Nice. And so watching that taught me a lot about, okay, well, if we're ever going to do merch, how do we do this right? How do I make every person who comes in, they have those little greeters, you know, Sam Walton. I loved that. He was like looking to cut costs but also put a greeter in front because he realized, oh, it makes people feel different too. Like they're special for coming in the store. To that point, I do that too.

26:26I don't like the middle. So I would say what I see with a greeter at Walmart is not playing in the middle. It's like price, convenience all the way here on the right. But then spend on things that others don't spend on because it changes the context of the relationship. I always talk about scale the unscalable. Actually, here's a tidbit. I believe one of the great misses right now for all of the characters like you and I and everybody else that's aspiring to like win on content and brand is community management. I really do believe that way more people need to DM everyone back. You and I do not have that bandwidth.

27:06But I'm telling you right now, if you're just kind of getting into your early stages and you have like 10 ,000 followers, and you're posting and you're getting 14 comments, you're getting 13 DMs a day, reply to all of them. Scale the unscalable. That's how I built Gary Vee, by the way. Content and replying to everyone on Twitter from 2007 to 2011. You kind of still do it on scale, because I remember when I came and spoke at... Beacon? Beacon. I came and spoke. That's normal. I'll go speak at people's events. It's an amazing event. I had a great time. Very seldom does the head of the entire event ask to get my phone number and text me direct.

27:45That's really actually not that scale. I mean, how many speakers did you have there? Hundreds. Yeah. Not to mention that's not your only event. Not to mention you're doing these all over the world. That's actually not even that scalable for you. Yep. And so it seems like there's different levels to the game, but you still do the unscalable even at the highest level of the game. I think the dirt and the clouds are the only interesting parts of the game. That's good. Yeah, and so even in my own organization people ask me how I scale vayner and I say 10 80 10 and they're like What does that mean?

28:14I go when we're doing important shit. I tell the team I have to be involved in the first 10 % because i'm molding it Then I disappear And then you need to come back to me to close it. I open and close The middle is the problem And winners and people aspiring to build big things spend way too much time in the middle meetings I've famously internally and a little bit externally obsessed with 15 minute meetings I had an epiphany I was like fuck I crushed the dirt The 15 minute meeting I'm fucking up the clouds I have a lot of one hour meetings that are actually three hour meetings I've done more off sites Two three day off sites this year We're only we're not even halfway through Than I've done in the last 10 And it's been monumental I had this epiphany in November December of last year I'm like wait a minute I've got the 15 minute meeting down, but you know, this is about like feeling your feelings.

29:09I could feel that a lot of important meetings that were an hour weren't getting wrapped up. So now I'm doing a lot more two and three hour meetings and even two and three day off sites, 10, 80, 10. That's a great framework because otherwise it does seem too much and you can get stuck in micromanagement forever. You're like, I'm trying to build a business. Gary and Cody, you said do that. And I need to have my hands on everything and I need to care about the dirt, but you can't all the time. Oh my God. I would argue for your audience, like the SMB audience, like the mainstream audience, the number one reason they lose is they spend all their time in the 80.

29:40That's why my dad got small, didn't go as big as he could. He needed, he wanted to know everything, wanted to touch everything. Many small business entrepreneurs are just trying to be solopreneurs. They don't realize it. They're scared of stealing and security, someone getting better at it and leaving. There's all these millions of different things that people worried about. 10, 80, 10. What do you think that young entrepreneurs are sleeping on right now? So many different things. You know, you know this. We've had the luxury of living just a little bit. We're still pretty young in the scheme of things.

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30:13But like, you know, I had so many, you know, when I talk about my career, my life, I always think it's an homage to my parents and my circumstance. And so I had a lot of things figured out at 23, right? I, my mom really actually built self-esteem. You know, I continue to believe that most people get successful because of insecurity. And there's a rare breed that gets there through confidence. And I'm so grateful that I'm in that small group. But I see it in others. But that's not me. That's how I was raised. And just the circumstance of being born in the Soviet Union and Jersey boy in the 80s and a million other things that are not me.

30:55I think a lot about the youth, to your point. and there's just a lot. I think, first of all, both men and women, I think we throw it on men, but I see it in a lot of young women, we want to get validation from the masses. It was always a vulnerability pre-social media, pre-internet to want validation from the outside. But the outside in 1974 and 1983 was the Joneses, a.k.a. your neighbors. That was like maybe your church, Maybe you're like neighbor. Like it was tight. Maybe the people in the office, it was small. You know, there's an extraordinary amount of wanting to show that you're successful going on.

31:37So I think one thing that a lot of the youth is struggling with is an extreme need for the Lambos, the watches, the followers, the cash, the trophies, the accolades, just so much outside validation. I think there's a lot of lack of self-awareness. I think that in general, that's a human thing. But meaning, I think a lot of people chase the trend, you know, whether it's, you know, cannabis or NFTs or crypto or flipping or, you know, listen, I'm curious about a lot of trends. But I think a lot of people are like, this is I'm going to do this because this is where I can make my millions. you know so I think I believe that one of the great ways to actually be successful is to truly know the things you like because you'll work that hard like I don't think I could ever work as hard as I did if I didn't enjoy it I couldn't mustard it up it's why I don't you know back we were talking right before we started the gym this morning was a grind yeah like to me it was like I really didn't want to.

32:41I really don't want to. And my gym, my eating discipline, my doing things around the house, these are fully procrastinations. These are laziness. This is avoidism. This is non-accountability. This is like, look, a bird over there, run away. I do the reverse and more because it's my love. I do the reverse and playing basketball. I like it. I'm like, should definitely not be playing. I like it. I go out of my way. I was just saying to you, my back was hurting all week. And I played last night. That was like crazy. So I think if you love what you do, you will do the things that actually are required to be successful, which is persevere through the daily shit.

33:23Right. It's hard to beat. So I think those two things really stand out to me. And then the things, you know, like I always laugh when I'm about to say it because I know some people are like Gary. But like I do struggle with an obsession to try to teach these kids about patience. You know, I literally punted my 20s and early 30s because I was obsessed with building a business for my parents. But I truly had nothing at 34. Truly, actually. Like when I started VaynerMedia, my biggest company, we started it in a conference room the size of this podcast studio in another company's conference room because I couldn't pay rent.

34:01How big is it now? Now it's 2 ,000 plus people, 350 million a year revenue. you. Not valuation. Oh, you run a profitable business that actually makes money. Shocking. So, you know, it's a big business. And that's only one of yours. Like how many, I was looking it up today. It's like Vayner3, VaynerSports, VaynerRSC, VFriends, which I think is a different entity. How many like Vayners you got? There's VaynerX, the holding company that holds like, that holds like seven or eight of the, that's the marketing agency holding company. Outside of it is VaynerSports because that's a separate business. That's me and my brother.

34:42My brother runs that with Greg Genski. That's becoming a pretty big business. We rep over 100 athletes, might even be close to 200 now. A newer one is VaynerWatt, W-A-T-T for Eric Wattenberg. That's a TV production company. Our first shows are gonna start hitting the air here in the fall. And like that's starting to move and groove. VFriends is the other biggest business I run. That's my Marvel Pokemon. It's an intellectual property. I do actually believe in my 80s. That's what I will be known for more than anything else I've done. And probably nobody understands that right now, right? Like when you launch it, they thought, oh, this quick little NFT thing.

35:18Yeah, I mean most people don't understand me and Vayner. Most people don't know VaynerX. Most people when they just heard 350 million, like when people come to Vayner, they're like often they're like what is this i'm like this is my company they're like most people think i'm a motivational speaker or a content creator which is fine i mean i'm not overly worried about it um vcr group i have a very substantial restaurant group that's going very well we have that fly fish club which was also an nft membership it's just there yeah it's really going well it was beautiful thank you yeah it's crushing which is good because that was very high risk, high reward.

35:54You open up that kind of eight figure build out and the restaurant business is not nice. It's the hits business. Yeah. You should hate them. It's a terrible restaurants and sports agencies, bad businesses, passion though. Chef Capon, Chef Connor, David Rodolitz, my three partners in that business. This is their life. My brother punted a lot of money because he just wants to be a sports agent, you know? And now he's starting after 10 year itch of like, hi, what else? You know, so I think it ebbs and flows. So anyway, long winded, I think I wish kids were like, no, no, I really love sailing. Let me start a business around sailing, whether it's content creation, let me go work for someone who's in the sailing business for five years, learn and figure out like that move.

36:37Like when people hear me say this, they're like, but Gary, how do I do that? I'm like, why don't you go work for somebody in comedy in, you know, the fashion, like everyone has just decided like I can start a business and most people are not talented enough in their teens or twenties to build a viable business just yet. Yeah. You know, the thing is miserable. Well, yeah, there, you know, this most people, this was a real wake up call for me when entrepreneurship got cool in like the mid two tens, like 2010, 11, 12, 13, everyone started running towards it. And I had always been there. I didn't realize how hard it was for people that weren't natural born.

37:22But then it made sense to me because I was a really poor student. And like, I just think some people know how to do school. I wasn't one of those people. And I'm like, Oh, this is this is going to be hard for these people. Because, you know, it's because unlike school, like I never did homework and failed every test. and the system pushed me through. My school system didn't want people to stay back. They were going for a blue ribbon. They just pushed me through. I literally sit here today, no fucking bullshit. In my four years of high school, I never opened a book, never did homework, never studied for a test, never did a book report, never did a project.

38:01And they just pushed me through. Which I'm not sure that's good or bad. Yeah. I mean, it's, it's probably neither, but in business entrepreneurship the land of business merit there's no pushing through like if I did that same thing in business I'd be out of business very quickly and back at a job and so yeah yeah I saw this stat today actually it was on on Twitter and uh it was because you always talk about how hard it is yeah you know and so there was this tweet today that was like read this if you're not as rich as you want. And it was the odds of making it that in the US, one in 1 ,000 make over a million in a year, one in 11 ,000 over 10 million, one in 35 ,000 over 20 million.

38:49And so the truth is, if you want to make it, you need to be an absolute freak of nature. Basically, you have to have outlier behavior. And I was curious what you think and how hard it actually is, because you're oftentimes telling all of us, it's going to be harder than you think. when we, I'm 49, when the number went from, when I was a kid, the number was, if I could make 100 ,000 a year. I grew up in lower middle class, middle class, kind of like vibes, more lower middle class. 100K seemed, I mean, I myself, with, you know, I'm 15 years old, I'm gonna buy the Jets one day, but there was another part of my brain that was like, man, the only time I was pumped, professionally, financially, was when I broke the 100 ,000 barrier in a year.

39:30No other time. No other time. When that number for the masses became a million versus a hundred thousand, shit got ugly. Like, just like, do you know how fucking hard it is to make a million dollars a year? Like, really, actually? And the problem for someone like you and I, if we've gotten there and we spend all our time around people that have gotten there, it doesn't feel rare. one of the you know one of the great things that has always happened in my career is I grew again because of where I grew up I always thought about the other so one of the first offices I opened for VaynerMedia was Chattanooga Tennessee not LA not San Francisco not Tokyo not London and one of the reasons I did that was I always wanted to be grounded to everything up down left right you when you go to Chattanooga Tennessee if you make a million dollars a year you're fucking on a And by the way, Chattanooga has a wealthy area, old Coke money.

40:25There's some great entrepreneurs there. And it's nice. Yeah, it is. Clean, honestly. I like Chattanooga. But look, I think that it's incredibly hard, and I don't know why people think it's easy. And I do know why people think it's easy. In the 80s, there was Lifestyle Rich and Famous. In the 90s, there was like, you know, the crib show on MTV Cribs. now 24 7 people are looking at propaganda in their feeds of watches and vacations and and I say because I keep hearing everyone wanting to blame Instagram and wanting to blame social media I say stop consuming it you know like if you're motivated by a grape I don't believe that most people are motivated by it I think most people get jealous and envious get insecure get And so I think it's super hard because, again, overcoddling parenthood in the last 40 years.

41:19School is bullshit system. Government's bullshit system. Most systems are bullshit. The only two systems that aren't like the most not bullshit system in the world is sports. When little Ricky goes on the field and he's nine, if he sucks at basketball or soccer, like it's exposed. No matter how much daddy and mommy want to make up some excuses or right. Used to be. Yeah, I mean, parents are really getting their hands and shit, but still, they'll go and fight a teacher. Like, parents in the 80s didn't, when you got a C, your mom and dad didn't go to school and fight a teacher and try to get a B.

41:55They do that now. But even though the, I mean, I'm in this circles, I have a 15, 12-year-old, 16 now, and 12-year-old, like, growing up in this last 7 to 10 years, parents want to go on the field and kick the ball for their kid. people want to go do something but they can't and then thus the kid gets exposed sports is the most merit the next closest is business the reason i say it's not the same as you you know this people are like i'm a three-time exiting founder i'm like you raised 10 million dollars and sold it for 200 000 you're a fucking loser you know what i mean so people can bullshit a little bit in business.

42:33There's, you know, there is a, but it's, but it's 80 % to sports, you know, and I guess in hindsight, I was attracted to merit my whole life because those are my two passions. I love a, I love a game where you know who wins and loses because it tells you if you're good or not. That's right. So do you think like when you see that stuff online, I'm not a big showy person, don't get me wrong. And I, I like nice shit. Like everyone's allowed. Totally. But I don't really, I think it's almost an immediate red flag. When I see somebody showing the Gucci Fendi Prada, the fast cars and the private planes, I immediately go, I don't know if you really had that.

43:08Do you got to flex it? What do you think? Like if you're talking to a young person, you're saying don't fucking follow people that do that. Yeah. You know, listen, I've taken some lumps from a lot of contemporaries who get mad that I talk about this because so many of them are in it. Um, look, I think that first of all it's so funny where my chemicals just went one of the great things and it's funny because I pontificate and share and ponder online 24-7 first of all just to set the ground rules I do not have the audacity to think that I'm right about anything anything let alone everything for me I'm in your camp a little bit But it's because I think a lot of people do that to funnel people into them, to monetize them.

43:58So I think about that a lot. And again, I think it's doing real damage. Like when I post every morning, every evening, I genuinely post from the lens, deeply from the lens of why would someone give a fuck about this post? Why is this good for them? And I do believe a lot of people on the other side of this podcast are not growing because almost every post is about what's in it for me. I want people to buy my course, my book, my collectible, my, you know, you know, and so I believe that the flashy stuff is inherently selfish, not selfless. and so but look I mean people are allowed like you know people are allowed to share like I get it again a lot of people grew up insecure and wanted these things and they're proud and they want to share it my big thing is that people that have over indexed on that move I have found over the last 20 years tend to struggle to stay on top tend to be less happy um so it's not only that the audience that's consuming the Lambo or the watch that I'm worried about, but I'm even worried about the person that's sharing it.

45:14I'm worried that they won't be able to sustain it. It's a great, great move. I want to talk to you a little bit about building big companies. You've built a ton. And so with your current knowledge today, I'm curious, like, let's say you had to go back, back to your wine days, almost. Let's say you owned a laundromat because I'm into those things. So let's say you own one laundromat and you had to start your entire empire from one laundromat today. Like what would you do? What would be the playbook? Content. Yeah, you know, because, you know, you and I are part of a breed that admires a single laundromat owner.

45:52And I think you have really done a good job of tapping into something that I think is black and white, which, you know, we talked about the last time we hung like this whole, whether you call it micro P or just practical business. obviously Main Street is the way you think about it. I think there's a huge opportunity for a lot of those people to build a brand. In fact, that's what I did. I built my brand. I am that person. I didn't even own the business. It was my dad's business. I was the person who built it. But my original content as Gary Vee, after five years or during the five years of doing the wine show, my original first ever thoughts about business and life and perspectives were literally out of a liquor store, one store, and I built my brand.

46:40I could have easily, if that's what I wanted, opened up 10 more stores, did micro M &A, and I would have built a very substantial franchise or independently owned multi-unit business, which would be worth a lot of money and in today's environment would be a very attractive PE acquisition as every small business is going to get consolidated, it feels like these days. So I really, the number one thing I would do is get into content for two reasons. One, if you're capable building your personal brand, I do believe is a moat. I've always believed that it was the moat. I've talked about it for 15 years that it's the moat.

47:20It is the one true asset that doesn't get commoditized, even in the AI world. You still have your IP. It's your copyright. It's you. Two, if you learn to be a content creator, the other thing that worked with me, and this was hand in hand, and this is what I want for this person, is you start getting good at running ads and doing content for your business too. So in my brain, what I'm dreaming up right now is Sally's building up her. She's like, I did this. This is how I bootstrapped it or how I inherited it or whatever's real. Here's what I'm doing. Here's my day-to-day troubles. here's how I think about it oh my god coins when when people stopped having change on them we had to put in these you know uh swipe your credit card or you know like you know just like the the battle stories of that business but also what she will learn in the story that I'm telling is she'll learn what really every and by the way I know a lot of small businesses listen so let me give it to you very straight disproportionately the biggest opportunity to grow your business traffic to your business, average receipt size is to run, if you're a local business that people come to, is to run 10 mile radius Facebook ads.

48:31And so Sally, in this journey of building up Sally, the laundromat entrepreneur, would also start to learn how to be good at these things, which she would then be able to use to run ads to her business, which is advertising matters. It's always mattered and it will always matter. And so content. You know what's so interesting too? In your story, I remember looking back at those old videos of you in your wine business. And today everybody wants to have a set, right? We're on a borrowed set. This one isn't mine, but they want to have this fancy set. But you know what the sickest set is today? You're actually a laundromat.

49:07I think so. Because it's show, don't tell. It's like, no, no, I own this. There's no fluorescent lights here. Watch me do this. You don't think I own it? Look, I'm right here. I believe the best studio in the world is the world. I tell my clients, which are mainly Fortune 500 companies, I'm like, look, let's make content at stores, in parking lots, at festivals. I genuinely believe that. I've always believed that. I was honestly the Pied Piper in 2009, 10, 11, 12 of no production value. Wine Library TV didn't even have a mic. No lighting. No lighting, no mic. Literally whatever the camera picked up.

49:44And so, yeah, I agree with you. I think that Storys Studio is a big idea. It's a good framework. Yeah, I think so. Storys Studio is something that I've really championed more privately than publicly. So I'm glad we're getting to pontificate about this. And I think that's right. Yeah. And it means you don't have to have a bunch of money because I'm all about the great equalizer. Like yesterday, my husband and I were kind of laughing in New York because New York is such an equalizer city in some ways. In the best way. Yeah, so I could drive like a fancy black car, which sometimes I do. And guess what?

50:16If you hoof it or if you subway it, you're faster than me. And so like that's a cool equalizer that doesn't exist in a lot of other places. And so I think this is a good example for content. Like the best performing ads for a lot of our businesses are exactly what you said. It's like it's a window cleaner cleaning a window and then it reveals a price. Like that's it. there's no production. And so production often, often again, is disguising insecurity. A lot of people talk about production. If you listen carefully, it's just an excuse to not do. Anyone who says I can't afford it is full of shit.

50:56It's called an iPhone. You all have one. the end nothing else zero i did it for fucking a half a decade a 239 camera from best buy was the only thing i used nothing else nothing such a good point you know another thing that i really like about you is um you kind of said it earlier you're like i take some i've taken some punches on the internet and you have this tweet that i was coming back on which is first they'll call you stupid, then they'll call you lucky. Remember, just make sure that you're always executing and they are spending their time calling you things. And I loved that line. How do you deal with haters?

51:38Easily. I, um, with compassion, with empathy, you know, I couldn't comprehend living a life where I spend time trying to tear someone down. This episode is brought to you by Google Chrome. You think you know a browser, But Gemini and Chrome? That's new. It can help you with practically anything on the web. Like restoring a vintage motorcycle from a 50-page restoration block. Or finally break down that long article you've had open for weeks. Gemini and Chrome is here for it. Ready to make anything online make sense? There's no place like Chrome. Check responses set up required. Compatibility and availability varies 18+.

52:17Hey Chicago, class it up with Crocs. You know back to school is coming in fast. So why wait to find your new fave footwear? Step into a local Croc store and step into your new look. Try it. Style it. Make it yours. Because the right pair doesn't just show up. It shows off. First day fits handled. Walk out ready for whatever's next. Visit your nearest Croc store today. Ever? Ever. I was just about to say, you know, we're starting to get to know each other. I think it's one thing in these settings I think the thing you would find interesting and this is going to make sense to you because I assume I'm assuming circles and things you've run in as you've built your career the thing that blew me away growing up in the game was that A players in private settings would spend a lot of time shitting on other A players it blew my mind I remember it was happening to me when Scooter Braun, Maverick Carter some of these people in business were starting to do really well.

53:22And I'd be at these things. I knew both of them well. So it's probably why it triggered for me when people would be jealous or envious and they themselves sometimes more successful. I was like, this is weird. This is interesting. Let me take note of this. Oh, insecurity. Oh, like, you know, wow, they don't realize that the world is a butt. Like I was fascinated. I just, and I understand it because the one place I'm not me is sports fandom. and my level of envy and jealousy of Michael Jordan and Tom Brady and Bulls fans in that era and Patriot fans is like anger, like almost like the most extreme Republican or Democrat feeling about the other side.

54:02So I can tap into the emotion that is jealousy and envy. And, you know, because I don't feel in control as a fan. But as real life human, I feel fully in control and I couldn't comprehend the idea of deploying jealousy or envy against someone else. So how do I deal with haters? Compassion. I mean, they're just not in a good place. Like there's no other way to say it. Like, could you comprehend spending your time tearing down and so many people do it and you're like, I just couldn't, why would I deploy that energy? you know if I believe something stinks or someone stinks my immediate reaction is to just walk away in perpetuity I want to save my energy and time I got shit to do trying to win out here that I remember that tweet I remember that era when I was thinking about it I always wanted to be an athlete but it wasn't in the cards um being a publicly known businessman with you know opinions left, right, up, down.

55:06I'm like, oh shit, I got to taste it. Like, you know, everyone it's like, you know, it's like hot takes, you know? And so, and I think about it being an athlete, which is if you're an athlete, you know, just got done with this great Knicks playoff run, but it ended unfortunately just a hair too short. But when you're on the court and they're booing you, if you actually take that in, it's very hard to perform. If you take it in and you get excited, that's how I take it like it's the way I deal with it is 90 % indifference and compassion like I'm like who gives a fuck comma man just wish Ricky pants 49 lived a life where he didn't have to like be mad at me because I know I'm triggering insecurities for him and 10 % of like gangster I'm gonna slice your throat like all right motherfucker keep talking like oh really like you think I've made it now let me build disney in front of your face with v friends and you're really gonna fucking be angry at 80 so there's a little bit of that but only but only 10 which is i'm like very grateful for maybe 20 depends depends on the day i like being competitive i enjoy being competitive in fact one of my great angers in the world is eighth place trophies one of my great angers in the world is when two passive parents get lucky enough to birth a competitive kid probably took after grandma and then they tell that kid like this game that they're crying about doesn't matter it only matters winning and losing is incredibly imperative to the human race nothing is good out of balance of course people like gary winning and losing like is it okay to like hurt people to win no no it's not okay but is it okay to completely eliminate merit and competitiveness and winning and losing no no that leads to let me say it slow suicide this is what people don't understand when you start to not care about anything, you get into a very dark place.

57:00Teaching a young kid nothing matters is a dangerous game. Or sports don't matter, but getting A's matter. You start teaching them fake shit. Yeah. I mean, I think also going back and realizing that nihilism is real. And, you know, some of the greats have talked about the fact that the most horrible thing you can do to an individual is to take away passion in some way, shape or form. It's black and white to me. Yeah. Yeah. As someone who's like fueled by it, I can, you know, like we're animals, like I can smell it when someone has it and I can smell it only two versions I can smell. I can't smell the middle.

57:40Interesting. But with passion, I can smell the two opposites. I can smell when someone's got it. Yeah. Which is why I've associated, invested and been around a lot of people who went on to become enormous and I can smell when someone doesn't have it at all, which is why I fucking wake up every morning putting out content to get them out of their darkness. So we've told them that content matters. Yes. We've told them that if you're running a small business, you should think about building up your brand. We've talked a little bit about IP, like all of this talks about content. But the number one of the biggest questions I get asked by business owners in our portfolio is how do you find great talent?

58:14How do you find the person to help you with social media by realizing you need to be the person that first understands it a little bit how do you judge something you don't know if i went into a surgery surgery right now heart surgery and i needed to judge what's going on we have a problem it's called i have no idea what the fuck is going on everybody who's listening when you own a business it is hard when you own a business you have to be adaptable. When you own a business, you have to deal with the shit. I know that you don't like it. You may even have an ideological disagreement with social media.

58:53You must be the person that learns it a little bit so that you can judge the talent. It's not about finding the talent. It's that everybody gave the job to their 20 year old niece because they thought like, oh, you're a kid, you get it. The problem is the 20 year old niece and nephew use social media to fucking hook up, not to build a big business. So, you know, my answer, and I talk to a lot of these businesses as well, is you have to spend 50 to 100 hours educating yourself and then doing. You can't read about pushups to get the results. You have to read and watch videos and listen. I even made it easier for you.

59:33GaryVee.com slash attention. I literally took my last book, which is 20 fucking dollars. I'm like, you can't afford 20 bucks? How about this? A 44-page free deck to tell you exactly what to do. But I recommend the book. Thank you. I gave day trading attention to all of my social team. Thank you. Yeah, well, again, you said thank you, but I said no, thank you. No, I get it. Because it's actually super. It's why I believe in books. I'm like, I cannot believe I charge hundreds of thousands of dollars to clients for consulting, and this$20 fucking book is like pretty much there. Yeah, 100. Well, and, you know, to be fair, why wouldn't I steal your 27 years doing this?

1:00:11And more importantly, my actual living the thesis of the book. It's not my only 30 years of working. It's my last 12 to 18 months. Yeah, that was different. You know what I mean? Like, that's what's so interesting about the books I write. I don't write evergreen books. Day trading attention is just a follow up to jab, jab, jab, right hook. Yeah, you're right. It's just 10 years later because shit changed. All I want to do, I'm incredibly obsessed with the contemporary. I want to be obsessed with the history to understand the contemporary. And then I just want to be of today. There was this great line, actually, when I was coming up with a bio on you that I was reading to Kate that is, I think, perfect for you.

1:00:51And it was about the fact that you are pathologically practical about where eyeballs were moving. That is so true. You're pathological. Like you are obsessed. And I think that's what it takes to win. I guess I want to close out with two questions here. One of them is, you know, you've mastered these underpriced attention platforms at varying times. You talk about it in all of your books. At any given time, there's an underpriced platform. So let's give the people the non-Evergreen. What is that today? Where is the underpriced attention today? Live social shopping. If you sell anything, and this is huge for your crew.

1:01:30If you sell anything You know that's not Like a physical thing Not a service VaynerMedia doesn't do this I can't do this with VaynerMedia We don't sell a physical thing If you sell a physical thing Which a lot of you do Every one of you Has to learn everything you can About TikTok, shop and whatnot W-H-A-T-N-O-T Those are the two leaders right now I expect Meta, Google, Twitter Everybody to get into this game Live social shopping is the underpriced attention. There are a ton of creators right now who will never get millions of followers and make millions of dollars, but if they switch to being someone that sells something on social instead of making lifestyle content, they will make millions of dollars.

1:02:15So smart. I forced Mike to do a garage sale. Mike did a garage sale on Whatnot this Saturday and made 700 bucks? Yeah. now I know you sold some trading cards and stuff like that but you also because I heard you were going to do just trading cards I'm like no no no I need you to like sell some random shit in the house give me one example of something that was literally sitting collecting dust in your apartment and you sold for how much

1:02:47right do we include shipping and handling yeah you charge the like I love this every time I do garage sales and everything I'm like what about the shipping like you charge shipping What about the eBay fee? I'm like, everything has a cost. Like, you know, like people love an excuse, right? People look for the why not. I literally think garage sales and flea markets are gonna happen in live social shopping. It's not just someone who starts a beauty brand. Or like those storage units. Kate, we're doing your storage unit. She has one here that she's had for two years. Right, she's paying monthly fee.

1:03:18She's paying 25 bucks a month. We should just do it live on YouTube. Not YouTube, because they don't have that yet. well that's so i want to turn it into a youtube video but do it live on whatnot or tiktok you can make a youtube video because that's great because that's content but live the qvcification of social media is here yeah listen to these stats 30 what some this is a stat i'm always a little weird with stats but this is real china is fully here china's got obviously one of the biggest economies in the world live social shopping in china now by the most conservative estimates represents 30 % of all e-commerce in China.

1:03:58Get the fuck out. A half a trillion dollar economy of live shopping in China that is bigger than almost every nation's economy. In the US, I just had the CEO of QVC. He put out this stat that I'm going to try to validate this week, but it feels right ish. He's like, we're already at 6 % on live shopping in the U S and no one's even seeing it yet. What's that? Do we know what that is compared to what QVC used to be? Cause it was like a lot than nothing then now growing. QVC has always been a ton and it's not a lot. It was still doing an ungodly amount of business. There's something about the behavior.

1:04:42You're almost like paying for the entertainment. You're like tipping the host. You're like part of the community. I have this concept called commerce attainment. So ready, how about this? You're a hairdresser right now listening and you sell shampoos and other shit, soaps and all the fucking shit in your place, right? You can go live on whatnot right now. At the bottom of the screen is like this$12 shampoo and you could just buy it while you're teaching people how to use the shampoo on a customer, this is real. Tea with Gary Vee, which I really did really well during COVID, I've brought back, I love doing Q &A.

1:05:21On Tea with Gary Vee, I now do it on Whatnot, not on Instagram Live. I do it on all my socials, but I drive to Whatnot. I drink out of a VFriends mug, and the mug is pinned at the bottom of the screen, and while I'm doing the show, people are buying the mug. Get out. Commerce-tainment. I'm not even selling in that format It's just subliminal right there Yeah or I'll make a reference I'm like hey you like my mug It's a mini commercial It's not even a commercial And you just like experimenting That's part of your thing You just never stop experimenting Yes after it's been validated I have a trillion dollar stuff Sells in China Now we have those functionalities It's going to happen here It's happening here TikTok shop is insane You for your portfolio must deeply understand TikTok shop So live social shopping is one of them Within social I'm a big fan for people that are obsessed with TikTok On Snapchat spotlight So Snapchat spotlight is much smaller But it's their TikTok right It's in their UI And there's a fuckload of 15 to 30 year olds in it But here's the good part Supply and demand of attention Like I talked about in day trading there's a lot of kids on it they spend a lot less time on it than they do on tiktok when i say kids i say 15 to 30 so if you sell to 15 to 30 but nobody's but the supply is low nobody's posting on there so i i'm very hot on snapchat spotlight um substack i think is really really interesting i'm about to delve in irl streaming so twitch you got to check out beehive i'm an investor in it so obviously very biased.

1:07:05I will absolutely do that. And they're here. I've never met faster builders. We invest in a lot of companies and shout out Tyler Denk. He's an absolute psychopath. He's like what you talked about. Speed. I think he's going to eat Snapchat's, Substacks lunch. I love it. Good for them. Yeah. Yeah. Look, and it's not even, you know this, you're too smart for this. I don't think Beehive is going to eat Substacks lunch. I think it's an and not an or. Yeah. Do you know what I mean? Yeah. Like, like there's too big, it's too big of a dressable market. Yeah. Very true. Uber Lyft. That's true. Like when I was like, Oh, Lyft, cause I was an early investor in Uber.

1:07:37I was like, Oh fuck Lyft's going to do well. But I wasn't like, I want multiple to do well. Yeah. I mean, look, I like when you're on it, like I don't want the Patriots bills and dolphins to do well. Like I don't mind competition. I just know it is. Yeah. Do you know what I mean? Yeah. But if you have a few, then you grow the market share entirely. Yeah. But both of those companies are going into a trend that's happened. Yeah. Like medium was, I was an investor medium, which was Ev Williams, who's an iconic entrepreneur, co-founder of Twitter, and before that, ODO, and blogger before that, one of the first blogging platforms.

1:08:13Subscription, Patreon, OnlyFans, and then the social sites are going to start. You can already see some of the moves they're doing, like, fuck all these other places. We've got all the audience. We're going to monetize. So there's a lot to it. But these are things I'm looking at every day. Let's end on, on AI. So, uh, what's going to, what are your craziest predictions when it comes to AI? Well, I've gone pretty viral lately because I, my craziest prediction is that most people's grandchildren will marry an AI robot. Fuck my life. Some of them will, not everyone's going to, but I think this is the biggest thing we've seen since the internet.

1:08:49Um, it's that big. It's when the internet came along, my thesis when I was a kid was, oh, this is like, like I bet my life on it. And the bet was, this is the biggest transformation ever. And like, everybody will be on the internet. And when I tell you when I said that in 95, six or seven, people laughed, laughed. When people are like, when they talk about AI, I don't think they realize it's oxygen. Like when I get excited about the blockchain, NFTs, Bitcoin, that is a big deal when I get excited about social media that was a very big deal email google search these are big deals this is a level above this is internet and AI meaning I view AI as almost boring to talk about because is it fun to talk about the internet as a foundation like no we talk about the things on top of it to me AI is now like omnipresent it's a reality of life and there's a real decade of recalibration, reckoning, disruption, opportunity.

1:09:56I'm baffled at anyone who's not spending an hour a day learning about AI and using AI. I couldn't imagine. And I spend a lot of time prompt engineering, you know, just if you don't know what that means, Google it or AI it. And that's what's so funny. Like even Googling it, I noticed I said to somebody the other day, I'm like, AI it, like go Gemini it, go Perplexity, go Gronk it, go OpenAI, you know, ChatGPT it. Like, it's like, it's huge. And it's like the wildest predictions are the internet of things, it thinking for you, it ordering it. Like, I think all of shopping will be done by agents for you based on your behaviors.

1:10:35Like, it will know better that you wanted that outfit than you knew. Facebook already knows me better than my husband with my shopping preferences. I mean, most days know things better than husbands know. But we're a bunch of idiots. I think that it is very clear to me that we are going into a transformative half century where AI will be like the piping of this reality. Piping, railroads, infrastructure, oxygen, whatever you want to call it. This is the biggest thing that's happened in a long time. Let's give people a couple things to do on that. Somebody's listening They're like alright fuck it Gary told me to do AI What does do AI daily In order to get better at it look like Inside of Twitter X Using Gronk Perplexity Or Google Gemini Or probably the one ChatGPT is so strong And so easy and common for people Download it and use it every day Like and then use it Like here's how I use AI Hey AI Like hey This is what I do actually Almost every week what are the five AI apps that popped in the last week that I should pay attention to?

1:11:46AI is answering that question for me so that I can go look at those apps and understand what's happening. Also, real quick, because I know a lot of smart investors listen here, be very careful in investing in AI. The reason I haven't yet is every week, you think you just invested in the best X and a week later, somebody crushes that. The speed, you want to talk about speed? The speed in which these apps are getting updated and better is profound. It is the first time that I am annoyingly an evangelist for tech that is not something I've invested in or own. Like I won't shut up about like whisper flow.

1:12:22Fuck the keyboard. The keyboard's gone. You just, you know, yeah, you just voice text and it's perfect from now on. I mean, that's wild. What about what about what about the fact that nobody has to learn a language anymore? Everyone's going to have ear pods that like you're going to talk to somebody. They're going to be speaking Spanish and you'll hear it as English and you're going to speak English and they'll hear the Spanish and Portuguese and Korean. Like there's profound things coming, but the wildest one is we're going to fall in love with these, you know, AIs. And then we're going to put that in love AI into robot bodies.

1:12:53And those robot bodies are going to go from looking like RoboCop to looking like, you know, Megan Fox. Sydney Sweeney. And you know, that Megan Fox movie is a preview. Yeah. Does that make you sad? No, it doesn't. No, No, no. It makes me, uh, it makes me understand that this is how it's always been. You know, like cavemen were different than you and I were. Supposedly we were apes, right? So like, does it make our apes mad that we like, like, you know, like shit changes. Like I look, I'm not like people are always like, Gary, that's gross. Or like, you need Jesus. I was like, I'm like, look, I'm not advocating for it.

1:13:33Yeah. You're just predicting. In fact, I'm like advocating for simplicity. I think it's, I'm sad for people that wear gold chains and fucking like take pictures in private planes. So like I love when people are like, this is sad. I'm like, you're sad. You know, like this is what's brewing. This is what could happen. You're asking for a prediction. I'm guessing, but it fucking feels like it's coming. I think you're, sadly, I think you're right. I do think it's a little sad, but that is every generation. But by the way, I go back to this. We're in charge. like if you think it's sad as a human one day like you can parent and grandparent your kid into like understanding the value of a human versus a robot right the problem is like is that like we have to get more comfortable with being uncomfortable the reason the robots are trending in my opinion long term is we want everything perfect it's exactly why you know But by the way, like, are we like, are we robots?

1:14:37Like, let me explain. Ozempic vanity hair extensions, boob jobs, fucking testosterone, HGA, like makeup, like, you know, like people can argue we're sad. We become very, very, very visual. Like 40, 50 year old men and women like you and I. Two generations ago do not look like the way we look. and those people can say we're sad. Why do we have to alter ourselves? What's plastic surgery? What's Botox? You know? Gary's gonna be like this in 10 years maybe? I'm probably not but I don't judge people that are. I just judge when they say something sad when they're doing the sad thing. I remember in the 80s when boob, like I was a kid but I remember when everybody frowned on someone who had a boob job.

1:15:27And now they're everywhere.

1:15:31you know what I mean it's true and so and so like I don't know is lip filler like sad to a woman from 1949 it sure is they think you're fucking sad zoom out huh so just because you think a robot said like like it's just gonna keep doing shit and I get what people are gonna say in the comments like yeah but that's still a human being I'm like okay like I don't know like okay I had a I hired an AI specialist who's so amazing. You walk into my office. The first time I meet the guy in person because we were interviewing him on a project basis. Anyway, he's sitting in the front area of my office. He's got a hoodie on.

1:16:09He's got those, what are those things called? VR glasses. VR glasses. And he's just fucking maestroing in front. And I'm taking a little video because it's funny. His name's Chadwick. He's brilliant. And his entire job is to see where AI can play in our companies. But I started talking to him about this idea. And he pushed me really hard on our humans' robots. He goes, should they be able to vote? Immediate reaction, fuck, no, they shouldn't be able to vote. He goes, okay, what about a human with a fake leg? What about a human with two robotic legs? What about a human with a neurotransplant in their head?

1:16:39Where does it become a human instead of a robot? And I was like, poof. Yeah, and by the way, it might not even be right. Like, meaning like, it could be the end of the human race. And I'm like, okay. Like, I don't, do you think I want that? but my intuition is that my grandkids will be gone by the time that happens and like you don't get to control the future like what is this audate this is where this is where the whole politics thing has gotten me crazy like we've gotten to this era where people have the audacity to think the world should be how they see it i have passionate points of view we just spent fucking an hour on it i don't think i'm right and i don't think it should be the way i see it like I just most of all you can't stop it you know technology is undefeated by the way as I sign off electricity demonized when it came out actually the word demonized when electricity was invented people did not put it in their home and still chose lanterns and candles because the word on the street was electricity had demons in it we're scared of new shit And Gary V, you're the man.

1:17:53Thank you for being here today. Thank you.

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From the publisher

In a world drowning in noise, the ability to capture and monetize attention isn't just a skill—it's the entire damn game. That’s why today, we’ve got Gary Vaynerchuk… the man who doesn’t just predict digital trends, he makes them. For over two decades, from transforming a local liquor store into an e-commerce pioneer to building VaynerMedia into a global powerhouse, he’s made foundational bets on giants like Facebook and Twitter before most even had accounts. He’s a multiple New York Times bestselling author, commands a daily global audience in the tens of millions, and has built a multi-industry empire by showing entrepreneurs how to turn overlooked attention into undeniable results and lasting legacy.

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