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A
I've always was fascinated by kids that would spend all fucking day building a sandcastle, like, all day. And then their parents are like, jimmy, time for, like, we're going in for dinner. And they would just smash it and that's it. And I kind of feel like I'm like that in life and in business. I'm doing it for the joy of building it. Not for people to take a picture of my sandcastle. Not for you to come over and be like, that's the best sandcastle ever. I'm building the sandcastle for me on this sunny day, quietly by myself. And so that is my life, that is my career, that is my content. And I think that has really, it's why I'm comfortable doing content. I'm not looking for outside validation. It does not give me self esteem, nor does it not give me insecurity. And I'm playing my game. This is the GaryVee audio experience.
B
Gary, I'm incredibly grateful to have you on behind the Wall today. Behind the Wall was started with the goal to shine a light on the people and stories behind music, movies and media. But it was also to inspire every underdog to go for it. And that's how I kind of feel about myself. And it's especially how I feel about you when hearing your story about everything that you've been through. But also, even though I'm excited, I'm also a bit nervous because I'm planning to talk to you and ask you questions about things I've never talked about on camera before. Because I'm really looking for your expertise in things that I don't think are talked about as much when it comes to the creator world. That'll be later.
A
Okay, well, I'm excited
B
for behind the Wall specifically. What I love to do is I always start out and I ask this question. I go for anyone who doesn't know who you are, what's something they know you from? What are some songs they know you from? What are some movies they know you from? Because my goal is to really shine a light, in my opinion, on the people who are more behind the scenes of entertainment. But for you specifically, I think what I want to ask is for anyone who doesn't know who you are, how would you describe yourself and what you've created?
A
I would say I'm probably a very contemporary entrepreneur that has a real heavy overlay of creator. You know, I think I got lucky that I was born at a time that when people look back at history and think about the creator economy, influencers, people that had public profiles through social and Internet, through television and film and music that happen to also be business people. I was really at that forefront. You know, I started a YouTube show called Wine Library TV, reviewing wine in February of 2006. Like, I'm looking at some of the people behind like, how old were you in 2006?
B
10.
A
You know, like when I think about how old were you in 2006?
B
10.
A
Yeah. So like, you know, you know, I got very fortunate that my timing lined up. Where I get to say for everyone who's listening is I was one of the previews of the influencer creator entrepreneur economy. I'm a businessman. An entrepreneur. I run business. Like right a few minutes ago before I walked into here at my global HQ in New York City. I'm in business meetings now. I will do creator type content and then I will go back to business meetings. So I'm an entrepreneur who has a knack for being in things early. You know, I'm an early investor in Facebook and Twitter and Snapchat and I'm the one on the Internet in 2018 that was yelling about get on TikTok. And I'm known for that. Right now I'm talking about live shopping, the QVC of social media that will play out. And so that's what I think people know me as out there.
B
You just said that your first video was posted in 2006 in Wine Library. It's been 20 years since that. Were you ever afraid to put yourself on camera though?
A
No, I'm. I'll go right to the heart of why. No. I was raised by a world class mother. Like a. I wish there was a. Like we were just talking about sports before we went on. Like, I'm very into it. You're not that into it. Music has a hall of fame. Sports have hall of fames. I wish, I wish parenting had a hall of fame. I know why it doesn't. You know, it's very unique. It's different than those things, but man, if there was, my mom would have moonwalked into being a first ballot hall of famer. She. So I was raised by a world class mother who navigated some other things that went in my favor. One, I was born in the Soviet Union, which is actually the reverse of something in your favor. I was born in a very bad place, but I got lucky enough that we got out of there and got to the US early. I was 4 when we were here, really. But my first several years of my childhood we were incredibly poor or lower Lower, lower class. And I got to learn that I had incredible happiness in the home, even though we didn't have stuff. So I knew that happiness did not come from money. And then I just had my own natural genetics and self esteem. And then I grew up in New Jersey in the 80s where, you know, everyone's making fun of everyone at every turn and fighting after school. And so basically this is a long winded way to say to everybody. By the time I got to middle school and high school, and in hindsight, I didn't realize this was happening in a time. At the time, I think I'm looking at like the seven people behind us. Like, I'm just kind of looking at them for human reference. I just know that I wasn't affected by peer pressure and judgment of my fellow classmates the way regular, normal people should. I don't even at some level understand it, but I will tell you that very early in my life, third, fourth grade, I started going into a very weird mental cocoon where I was very emotionally intelligent, naturally hung out with a lot of elderly people, and just got my perspective right way too early. Which then meant I was way too happy. Which then meant by the time I was 30 and already successfully built a huge business for my parents, making a video on YouTube and worrying if people were gonna think it's stupid was the furthest thing from my mind. And that's why, you may know, some people may know here I make so much content around, don't worry what they think. So many people are living their entire lives based on the judgment of strangers they don't even like or don't even know. Definitely don't know. Hence the strangers, you know. So, no, I was not concerned about the judgment. I was not concerned about getting quick success. I was loving the first 50, 60 episodes. Hundred episodes when barely anyone was watching. I. I like building. You know, it's funny, I've said this a couple times publicly. It popped up again right now. I love watching, like, you know that kid? I don't know. Are you this kid? Do you remember you've gone to the beach?
B
Yeah. Yeah.
A
Okay. I don't know. Like, you know, Arizona. I'm not sure what the beach scene is. I don't know. I've always was fascinated by kids that would spend all fucking day building a sandcastle. Like, all day. Like, you know, I'm just laying out, reading my book, whatever, all day. And then their parents are like, jimmy, time for, like, we're going in for dinner. And they would just smash it. And that's it. And I kind of feel like I'm like that in life and in business. I'm doing it for the joy of building it, not for people to take a picture of my sandcastle. Not for you to come over and be like, that's the best sandcastle I've ever. I'm building the sandcastle for me on this sunny day, quietly by myself. And so that is my life, that is my career, that is my content. And I think that has really, it's why I'm comfortable doing content. I'm not looking for outside validation. It does not give me self esteem, nor does it not give me insecurity. And I'm playing my game.
B
You just said that you've been posting for a long time. I know that because I used to listen to the Gary Vee audio experience back in the day when I worked a 9 to 5 job.
A
Thank you.
B
Took pieces of. I used to have to do all the grunt work where I would take pieces of paper that were stapled, I'd have to unstaple them, I'd have to scan them into the system and then I'd have to restaple them. And during that entire time I would listen to a bunch of different things. But also the GaryVee audio experience being like, post on TikTok, post on LinkedIn and I would, I would post three to five times a day for I'd say like three months at the time because I got laid off from my job the day before Thanksgiving and then I got a new job the day before COVID all happened. And so I worked from home and I would work my 9 to 5 job answering calls for financial aid. And then anytime I could, I would work at night creating content and I would do that and I would post content throughout the day so I could get through it. So you have been posting for a very, very long time. But what I find to be really interesting is in order to prepare for behind the Wall, I try to listen to as many interviews as possible and it's really cool listening to all the interviews from back in the day again. One of the things that stood out the most though was your belief in success. You talk about how it comes from who raised you.
A
Yes.
B
And I would love for you to go into more detail because I really connected with both of your parents stories and I would love for you to go into more detail about what you learned from them, how they were raised.
A
Yeah, so my parents have very challenging lives. Both my parents lost a parent very young. My mom lost her mom at 5, and my dad lost his dad at 15. And again, I'm in a room right now in America. There's some diversity in this room. So I don't know if people were born here or their parents were born in another country. But, like, even when friends. Parents, I had lots of immigrant friends, were born in another country, they were not born in the Soviet Union. The only nation in the world that is similar today to the Soviet Union, where I, let alone where my parents lived the first 20 years of their life, is North Korea. The only one. We were born in a place where you were not allowed to leave, AKA jail. Right. So my parents grew up Also in the 50s and 60s in Russia, the Soviet Union, which is more similar to America in the 20s and 30s. So like many of my friends, my parents, I don't remember if my father and mother. I think my mother. But many of their neighbors and relatives did not have a working bathroom in their home. Like, this was like, so now we come to America and it's rough. We're living in Queens in a studio apartment like this with six family members. But for them, it's like, way better. You're in, like, freedom. Like, my grandfather spent 10 years in jail in Russia for nothing. Like, it was just like that. So my parents were basically, by the time I'm four, five, six, conscious. They're just grateful for the opportunity to work their faces off and have no luxuries. I went on one and a half vacations in my entire childhood. It didn't even cross my mind. I didn't even, you know, when you're growing up around, I'm bouncing around here a little bit. One of my friends, dads wore the same pair of pants every day. Like, we grew around, not a lot. We came from less. And, you know, they never complained. Brother. You know, again, my content back then. I'm sure you're busy now, but my content today is probably even more about this. Like, complaining is destroying people. Like, everyone in this room has something that they're concerned about, something that's an adversity, me included. Like, you know, like, you know, fame or popularity or money. Like, it does not take us away from people being sick in your family, you being concerned about things, random events that are challenging. And then the pressures. You know, I have 3,500 employees. I feel a lot of pressure about that. It's people's lives. Tyler Bryce. Just like, it's pressure. Like, everyone's got stuff. But what my parents taught me was to not complain, to be grateful for what they do, they taught me work ethic. My mother never had a baby. I did not have one babysitter or one other person clean our home in my entire life. My mom was home every minute. She did everything. Like just that level of work ethic with the inability to complain just became so culturally foundational. I'm embarrassed to complain now. I would argue our family, you know, like anything, you can take some things too far. I think we didn't learn how to communicate vulnerabilities or some communication things that probably could have been better in hindsight. But man, I wouldn't trade anything for how I was raised. And you know, my dad worked every minute to allow my immigrant mom to stay home. Immigrants, both parents tend to work, you know, my dad worked his face off, you know, but we lived within our means too. Like a lot of people now that have money problems are buying purses and $100 sneakers and buying coffee every day for five bucks a cup. Like we lived humbly even below our means to save money. Saving money was such a North Star. Nobody even talks about that now. There's no talk about saving money, you know. And so I was very fortunate. I was raised by very hardworking, very humble. And then my mother was an angel of sweetness and optimism and hope and deliciousness. And so, you know, I sit here on the shoulders of them. Brother, I'll be honest with you, like all the Gary Vee love on Earth even. Do you know how humbling it is to hear you say what you just said? Like in my job, I was listening to you. It's flattering and yet it almost like passes through me to my parents. Like you said that compliment. I'm like, oh, there's the compliment. See ya. You know, like, I'm very detached from my notoriety and success because I think it's my parents.
B
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B
because you feel they gave you everything you ever needed.
A
I feel like I'm the byproduct. I feel like, like, this podcast, you should take pride in it. You're the arch. You're doing it. I am prideful about my companies, like veefriends. When I build it dialed in dog. Like, when I build the next Disney Pokemon, I'll be like, dang. You know, I'll be proud. And I'll say, like, my parents made me a good person, but I feel like I did it. Me, Gary Vaynerchuk. I am the byproduct of them. Obviously, like, wildly, like, anatomically, they birthed me, but no, no. My mom made this. I am the vase that my mom created. I am the fucking vase that this woman created. And then my father. I talk a lot about my mother, but I will say something. My father did. One very important thing that I think is was the potential missing ingredient. My mom gave me all the things I am. Empathy, kindness. Like, so many things I'm proud of. But, you know, my mom has gift of gab, too. Like, she's a schmooze. Like, she'll schmooze a story. Aka when I was 14 and started working with my dad, my dad thinks an embellishment is like a catastrophic lie. Like, if you were like, my dad was your dad, and now I'll make pretend I'm your dad. Right? How many people listen to your podcast? And if you were like, I don't know, dad, like, 70,000 or 700, I'll just use 700. If it was actually 694, I would make a federal case about it. You're a fucking liar. And he scared the bullshit out of me in 14, 15, 16. Cause I was a salesman. I would try to sell stuff. I'm like, this is the most delicious coffee. I was a kid at 14 trying to sell my lemonade or baseball cards. In hindsight, I have such gift of gab and such charisma that I could have gone down a different path. And I really thank my father for, like, scaring the baloney out of me. Because, you know, I think when people first see me in content, all that charisma, extrovertness, people are like, wait a minute, is this guy for real? I am for real. That is a lot to do with my mother, but I will Say equally. And by the way, if not more, I'm real because of my father. Cause in my early teenage years, he scared the fuck out of me. And by the way, my father is a Soviet dude who never smiled and his eyebrows are naturally in the mean state. So, like, I was like scared of this dude. So, like, when he was like, embellishment is lying. When he was like, your word is your life. I'm like, okay. By the time. And so I got very fortunate, bro. Hey, everybody. Hope you're enjoying the podcast right now. Make sure you follow the podcast. That's why I'm interrupting. Let's keep going on this show, but follow the podcast. It'll make my mom super happy.
B
You just talked about you. You have immense pride for the company you built.
A
Yes.
B
During some of the interviews I watched, you talked about how people often build companies or something from immense confidence or immense insecurity.
A
Yes.
B
And I would love to know your definition of what the difference between the two is.
A
I believe a lot of people reach the top out of being angry at the world. And I'm gonna fucking show you. Because they didn't get the love because their parents didn't set it up. And they're just so mad at everyone and they think they're lesser than that. The only way they know for you to like them is they're gonna make so much money and be so known that you're gonna be forced to like me. And that is a very dark Darth Vader, like the dark side energy. And then I think a smaller group of people get to the top on a pure love train, on some Yoda shit, on some Obi Wan stuff. And you know, I am very grateful that I am in that smaller camp. And when I find others that have gotten to great places or built great things from a love, from an optimism, from a hope, from being good to people, it comes very easy for me to see. And it also comes very easy for me to see when it's the other, that you do not think you're worthy. And so you needed these outside validators, money, a blue check mark, millions of followers, a Beverly Hills home, a BMW, a Rolex. You needed all these other things, things to close those gaps. But let there be no confusion, that's why I love Star Wars. Both the dark side and the Jedi's do get to this pretty extreme place. My point of view, though, is for the people that are listening that have gotten to the top through insecurity. You've got to work through that with therapy and your Own self work because it's not sustainable. There's a reason people get to the top and crash. It's because when you get somewhere because of darkness, when you burned people along the way and stepped on people, when the people around you don't admire you, they fear you. It's not a very nice place and eventually it gets suffocated and burns out.
B
Do you think people who have built from insecurity can change and build from a place of love?
A
I do. It's why I'm so passionate about how I make content. I do believe in therapy. I do believe in changing your inner circle and spending more time. I do believe that listening to a positive voice in a podcast over and over and over and telling you, you can, bro, you can. I think that matters. I think you are the people you're around, and I think it's very important. And I think you can. And here's even a better one. I even think if you've done it wrong and you've done wrong by people for 60 years, and for some reason you're listening to this podcast right now, and you're just like, you know what? I'm tired and this guy's right, that literally tomorrow could be the day you start. For 38 years, I did not take care of my health. I didn't exercise, I didn't eat well. And, like, it was hard at 38 and a half. I always say that, like, I'm a little kid. It was hard at 38 and a half to, like, get more disciplined to start going to the gym. Like, this morning, I didn't want to go. Like, I tried to come up with any excuse that I could tell my trainer, you know, like. But I did it and I thought through it. And I do think that some things come natural to people and other things don't. But I do believe in the human spirit, bro. I believe humans can change, but they have to take big action. I will say this for. For everyone who's listening and in this little room of you youngsters, you gotta pay attention to the people you're around, including your parents, including your siblings, including your plus one. Like, there are people who are. They're not bad people. They're just hurting. So they're trying to take you with them. It's the old misery loves company. It's not like they're bad people. They're just hurting. It's funny. I don't struggle with people that are bad. To me, I have actually a lot of compassion for it. I have empathy for It. But I think a lot of people struggle with it and get caught and they're just like, but, Gary, it's my mom. I'm like, I get it. Like, I'm not telling you never to talk to your mother again. But if you have a mother that all she does is complain about everything and everything's negative and the world sucks, maybe you don't have to talk to her three times a day, maybe once every three days. And you tell her like, mom, like, this is just a little bit too much of this point in my life. I need a little bit of a breather. And she'll go crazy and be mad at you because that's what will happen in that situation. But I think people can change, and I think it's the people you are around and what you listen to. You know this right now. I know I'm on a long winded answer here, but stick with me, everybody. If you go on your news feed and social media right now, there's a lot of negativity to be had. What I don't believe that people realize is there's a lot of positivity to be had too. But we get into these cocoons and we're very good at rubbernecking. Like, why are we looking at that accident where, you know, like, we find ourselves looking there? And I'm hoping people look for more optimism and more joy and more love and more opportunity.
B
Yeah, it's interesting you say that because I feel like a lot of people went down the path of negative type content because it gets engagement. And one of the things that I found that I really loved was to talk about the people who weren't being talked about. So songwriters, at the end of every video, I would say, but why am I telling you this? Because there's so many people who are behind our favorite works of art.
A
Yes.
B
People don't know who they are. Yes, people really connected with that message more than anything.
A
And it's. And you were coming from a place of love. Think about what you're doing. You're like giving flowers to people that normally don't get flowers. That's fucking beautiful. And, like, makes a lot of sense to why it worked.
B
Do you think, though, there's a difference between having insecurity and having competitiveness?
A
Yes, I'm incredibly competitive. Like, I like to win. Like, I'm weird with board games. Me and my brother's only significant fight in our life was over Scattergories. Like, you know, like, no, I think there's a reason there's Two different words.
B
How do you know which place you're at?
A
I. That's a great question. Let me tell you what I subjectively think it is. Competitiveness is fake, meaning it's momentarily right. You and I are playing Uno and I want to rip your face off, like straight up. But then when we're done playing Uno, I want to have a cup of coffee and be like, hey, how do I help your podcast? Insecurity, which often leads to envy and jealousy, is you always want to rip the Pearson's first face off. It's sustained. It's sustained. That's like. That's when people use I'm competitive as an excuse for envy. It's sustained. Like when I play pickup basketball, I want to win. When I make a piece of content, I like it for it to be good. I like my companies to do well. I would say I'm competitive, but the people that make negative content and the theme you're talking about, there's a saying that I love. There's two ways to build the biggest building in town, right? I'm sure you heard that in some of my old videos, because I bring it up a lot. One is what I'm trying to do, just be so good that you're just building the biggest building in town and you're actually happy for other people's solid buildings. Or do what's going on right now, tear down everybody else's building so your little fucking building seems like it's like the biggest.
B
And then if you do build the biggest building, you can bring people with you.
A
Well, that's. I mean, I will tell you, like, that has been the great joy that I didn't know as a kid. I always knew I wanted to be an entrepreneur. I didn't know the impact I could have on others careers. Bryce just started, right, literally day two, five, three, this day, Wednesday. Oh, shit.
B
Alright.
A
Day three. You know, one of the things, even in the interview when I was talking to him, I was like, bro, what's crazy? Cause he's taking the role of like filming me and traveling and obviously drock. Caleb Babin. Some of these people have gone on to like really build huge careers on the equity of being here with me during this time. I even said it to him. I said, hey, even in the first interview, before he's even an employee, I want him to feel safe. I'm like, hey, if you want to come here for a couple years and use it as a stand, like, I'm happy. We'll just communicate about that. That Is a humbling thing that my universe of building what I'm building is actually helping others. Whether that means with T. Walsh. Been for hours. In fact, we just talked the other day. I don't talk to them every day. I got a lot going on. Like, hey, I want you to take the next step. Get closer with me. Whether that means 20 years together, whether that means it's a stepping stone for them. Yeah. I think one of the worst things I see about people building big things is, is they think it's slavery. They think their employees are owed to them. I hate it. I'm so confused by that. I wanna be so good that they want to be with me the whole time. But I also get excited if they're able to use what they've learned or the equity they gained with me to go pop off and do something of their own. What kind of hypocrite would I be if I didn't want them to have their own entrepreneurial things when they go to other companies? I'm like, hey, man, the culture's not gonna be as good. There's a little bit of that. But. But, you know, yeah, man, you're right. Building big buildings and creating collateral impact is a blessing.
B
It's interesting you brought up Tyler.
A
Yes.
B
Tyler and I are in an accountability group for the past three years.
A
Yes.
B
And we've been keeping each other accountable. And he's someone that I often call pretty much every day. And like, before some of my biggest interviews that I've had, I have felt like an imposter. As an example, before talking to one of the songwriters of K Pop Demon Hunters, ej, I felt like an imposter before interviewing Bruce Springsteen and the cast of his. Of the movie that came out with him. I felt like an imposter. I was like. And one of the things, I was having this long conversation, making all these excuses, and eventually got to the point, like, why do I deserve to be up there? And he's often one of the people who comes to me and he's gassing me up. He's helping me. And I guess my question is, when imposter syndrome comes, how do you tackle it?
A
A couple things. One, I think we're living in a world right now where we've created words that are way too heavy for what's actually happening. Like one that I'm super pissed about right now is toxic positivity. I am pissed. I'm gonna get on that. I won't even go into a rant. Cause it might take up all the Time. Like, as if pos I get delusion and selling a bullshit dream. Yes. But like, do you know what imposter syndrome actually means in real life? Like, when OGs like me from decades ago when the word didn't exist, do you know what it was called?
B
I know what you've said in the past, but I would love.
A
I even have a new definition. Cause I know it's a micro, micro insecurity. You're just having a quick moment of insecurity, being like, I can't believe it. Little old me from Arizona is about to interview Bruce. Like, all of us are supposed to have those moments. I pinch myself all the time. Like, I. Especially at this point in my career, I'm getting DMs from like presidents of countries and like the most. Like, I don't even know what the fuck's going on. But I don't think, like, I'm lesser than my brain goes into. Like, well, why not? Like, you know, I don't know. Like, in the narrow things that these people want to talk to me about, I'm passionate or knowledgeable. You are passionate and knowledgeable of what you have. You may not be the most passionate, you may not be the most knowledgeable. You might not be the best interviewer. I don't think, like, you're Larry King, but you're on your way. And you're probably better today than you were before, right? So I would just say that I'm struggling right now because I think youth culture has created words that are just really heavy. Imposter syndrome. Like toxic. Everything's so heavy. And the words we used were just lighter versions. Like, I'm feeling like you would have called Tyler ready. If you and Tyler were my age, you would have called and be like, yo, bro, I'm feeling a little insecure about this interview that feels way lighter than imposter. You know, I think we've made things heavy on some really deep psychological warfare that we're doing to older generations. I don't even want to go into this, but, like, we're making things heavy. Cause we're looking for sympathy. We're looking to continue our over coddling of modern parenting. There's a lot to this. Nonetheless, here's what I would say to you. How do I deal with it? How do I recommend people dealing with it? Take some heat off. Like, what's gonna happen here? You're gonna. Let's say this is the worst. Let's say you're terrible in this. Like, you're bumbling. Let's say you really admired me because you viewed me as someone who really did help your career and you were nervous and it wasn't what I mean. First of all, me as a human, I would feel compassion for that and jump in and try to make it better and hug it. Like, what if I was the reverse of me, Bizarro Gary, and, like, storm down and be like, you stink. Who gives a fuck? You'd be like, fuck Gary Vee and move on with your life. I want to get people to think more about worst case scenario. We've created mountains out of molehill hills. We've created fucking mountains out of molehills. So how do I deal with it? It's just not that important.
B
Every business meeting that you have, every conversation you have, I'm guessing it's a different goal every single time. For example, you just talked about, like, if this is the worst interview I ever do.
A
Yes.
B
One of the things that I always do when I walk into an interview is, like, I want to try to make it, like, the best interview possible, which isn't right.
A
But, you know, you're putting. What I love about that is that means you're putting in work, listening to other podcasts, trying to figure out questions that haven't been on the plane. It's humbling, and I admire it. And for every interview you do humbling for me in this one, you're trying to think of different. Like, I love that. That means you have pride in your work and you're trying. That's great. Good for you. That's amazing. That's admirable if there is. I mean, I try to give the. I'm one of the most compensated, most successful public speakers in the world. Every time I go on stage, I'm like, man, I gotta live up to this hype, you know, like real talk, you know, And I give it my all. And I'm improv. So I'm not. Like, you put in good work. Like, I'm improv. So, like, you're. It's like SNL out there. Like, you don't know. You know, I kind of improv. I mean, here's the reality. I'm talking about things. I know. It's just like this, right? Like, I don't have to think. I just talk about shit. I know. So it's complete impromptu, in that I have no idea what I'm going to talk about now. What I'm good at is, okay, this is the Dentist Academy of the universe. These are 5,000 dentists who want to build their Practice. So my brain goes into, what would I do if I was a dentist? And because what I do for a living is attention, marketing, business building, how to communicate to the world. It fits for everything. It doesn't matter what I walk into. And because I'm still in the traffic and in my craft, I can speak in detail about Substack right now and LinkedIn and podcasting and vlogging and live streaming and what's happening on Kick and Twitch and SoundCloud and Spotify and TikTok and Hive Beehive, which is a competitor to, you know, Substack. I go deep. I know what's going on in threads, threads in detail, Snapchat, Spotlight, their TikTok. Like, I'm a practitioner. I'm good at my craft, so I stay in my lane. But it's improv. Like, the joke. I make the analogy. I make the path. I go. I might go. Do you know how improv I am? There are some times where I actually try to go down a certain path. Like, I'm three minutes behind the curtain. They're like, gary Vee. I'm like, okay, I gotta really talk about live shopping. And then something happens. It happened right now in this interview. These things go on and it's over. It's like everything gets blanked. And I'm just going, but I think that's great that you have that pride.
B
How do you define success for a
A
speech or, like, audience reaction?
B
If you don't get an audience reaction, is it like, what goes on in
A
your mind that I'm disappointed? That, like, you know, like, you know, with my style, I curse a lot, so usually I'll throw a guy out a curse, and it pretty much looks like this. 50% of the time, people are pumped. Like, they don't hear a lot of cursing on stage. They're like, yeah, it's real 30% of the time. No, no, that's not true. 40% of the time, it's like, fine. It's like they know. Especially at this point in my career, they know who I am. But it's like, okay, he's gonna curse a little bit. Five or 10% of time, it's like, ooh, that didn't land. And then I'll, you know, back to improv. I'll, like, start to walk away from it once in a while. Man. I've given maybe over a thousand speeches publicly at this point. I would say maybe two hand, like, maybe 10 times. Remember this one? Talk very vividly in Midtown, where it was an open bar. Late at night while I was giving the keynote and these people wanted to fucking get hammered and hook up. They could give a shit about social media marketing. And it was, like, really hard, and I was, like, really pressing. You know, there's also times where it's well received, but I didn't love it. Like, I feel like, eh, this is all right. That equally feels almost weirdly the same as not nailing it. But, you know, I kind of walk away and try to be better for it the next time. Luckily, that is one of the places where even my worst appearances are like a C. I don't have DNF ability in live speaking.
B
How would you define dnf?
A
I mean, a lot of speeches I've seen, like, people are boring as shit. No one gives a fuck. Everyone's on their phone. People can't wait for the person to get off the stage. They're literally reading from a teleprompter. Like, people are falling asleep, could give a fuck, getting up and getting coffee and taking a piss because they just can't wait for the next speaker.
B
Is it because of how many speeches you've done now and what you know from it, or do you think it's just.
A
It was a natural talent. My first speech, I remember, like, yesterday in Florida. I had never given a speech. I'd never thought about giving a speech. They paid me $5,000. I thought it was like 80 billion. I was stunned. I was getting paid for. I got there, people were giv. I'd barely been to speeches. People had slides. I'm like, oh, shit. I don't slide. So I'm like, yeah, I'm a DNF student. I'll just go up there and do whatever. And it fucking rocked. People. Like, I was like, fucking Elvis. It was over. I was the last speech. People were rushing to the stage. Could I ask you more questions? I back then used to not fly home right away. So I was like, staying in the hotel overnight. We're just gonna work in the hotel and have dinner. I stayed for four hours and talked to every person. And literally that high, I was like, oh, my God. You know, it's funny music. You hear a lot of people. You guys know music better than I do. Like, the first time they picked up a guitar, right? It happens, right? The first time they went to. I'm sure some people, right? You know, like, people have humbly told you, like, no, it's just in me. Athletes we talked about earlier, like, I see LeBron James little videos when he was like five, like, you knew. And so, like, you know, I'm not saying I'm LeBron or some all time musician, but in public speaking, it came really uncomfortably natural.
B
But then again, like, I talk to a lot of artists where, like, there's a lot of things that don't come incredibly natural to them. What are some things that didn't come natural to you?
A
There are still things that don't come natural to me that are essential to running a business. Reading contracts. Do you know that I have no. I might not even own my own businesses. My head of legal, Mark Yudkin, I trust him so much. Everything's a contract. He could literally put a contract in front of me and be like, you give me everything. Yep. Like, no clue. Finance. I'm good with numbers from a common sense standpoint. Like, my 7 times 7 is 49. Like, math comes natural to me in basics, but there's a reason I got D's and F's in like algebra and calculus. And more importantly, I don't want to spend any time balancing the books. I sat through a finance meeting today. I'm actually proud I've gotten to a place where I found a way to enjoy it. But I went years. I mean, I built this company from 0 to 100 million in revenue, and I don't think I looked at finances once. Now I had my brother looking at like, there's reasons not as, but like. And I know how to like, I know common sense. Like, I know how to not run out of money. But finances, legal, these are foundational things to running a business. I'll give you one. I'll be vulnerable. You definitely heard this. Candor. Candor on public. I'm a fucking G podcast stage. I'm Candor. Fucking capes. I'm the fucking superhero of Candor. Real life. Bryson's been here for three days. I already feel less wanting to tell him what he's not good at than three days ago. Cause the second people get into my world, I'm like, let's be friends. Let's be family, let's be like. So Candor was a struggle for me. I've really fixed that in the last five years.
B
How?
A
I went through a lot of every challenge I've had in my personal and professional life. I looked myself in the mirror five years ago and said, I've got a kryptonite. It was hard. This goes back to why I think people can change. I just looked at myself in the mirror. I'm like, why do some former employees not like me? That's insane. I'm the nicest and I love them. I'm like, fuck, it's all the same movie. I was unable to tell them what they were not good at. Instead I'd be like, great to see you have the best day. I would start to build resentment because they sucked or not or under, that's not unfair. Or they under delivered against my subjective right KPIs or objectives I was unable to communicate to them. And then out of left field, they got fired and they were mad at me. They're like, what the fuck? Where the fuck did that come from? And everything bad in my personal life, relationships and professional life was my inability to not be canderous. Building up resentment and then leaving everything for them. But like leaving, right? Or firing. Because I have to like, can't have the company go out of business. I can't let the good people go down with the people that are underperforming. So I just finally looked myself in the mirror after several enough momentum professionally and personally of like. And I just wanted to be better. Like, I'm always self checking myself and I just finally. It was like kind of like blur. First I didn't see it at all in my 20s, then probably in my 30s, I could kind of like start getting a little blurry. You know, it's coming into focus. You know, in my early 40s, I'm like, mmm. And then, you know, some people that were working with me for nine or ten years got really close enough to be like, hey, you do know that like you. I used to call it razzing. I weaponized a word. I'm like, I'm gonna razz you. What I was doing is I was being passive aggressive because I was upset with your performance. But I couldn't tell you so I had to innuendo it. And I'm really happy where I'm at right now. I'm getting more canderous.
B
That's something that I have a bit of a problem with, especially when it comes to more conflict.
A
Yeah, conflict. Well, by nature, if I'm going to tell Tyler right now, like, hey, I think you're working too much on your sidewalk walk. This is not true, by the way. Tyler, don't worry. But like, I know he does them. If I had a cause, he works his face off. But if I was like, oh man, he's like here, but he's really downstairs interviewing emerging rappers. And like I'm paying him. Like before I would like make a joke, like I'd go to the bathroom and be like, go to do a rapper, you know, like, try to, like, do something where I didn't have to write. Like, by nature, if I was gonna come to him, who I am now is I would call him and be like, hey, brother, there's so many good things you're doing. I gotta be honest with you, though. I feel like. Like, you're kind of, like, working on your own thing half the time, and I'm paying you full time. I can now do that in a nice way. But by nature, that's a conflict. So anything that's canderous is gonna touch on conflict. So I get it. Go ahead.
B
Did that take just practice?
A
Yes. It still fucking sucks for me. It's still. Like, I have butterflies in my stomach in the morning when I wake up, when I have to talk to a junior employee and tell them they're not doing well. Me, junior employee, if I'm gonna have to have that convo for whatever reason, maybe I know their parents or something. Like, it's. Yeah, I don't like it, but I've definitely gotten through it. I'm on the other side.
B
It's very popular, at least in current business practices, at least content practices, where often business owners talk about this idea of only working on the things that you love. Only working on the things that you're good at. Do you know, did you not feel that you could have hired someone to be that, like, Candor's bridge for you?
A
I did, but I thought it was. It's not authentic. Because I'm so deep in the culture, I could. By the way, that's what most people do. They have HR to do the dirty work. I'm in the shit too much. I'm in the fabric of this company. I like, know people's like, real lives. I'm like, by the way, that can happen to somebody. I don't know at the. I have 3,000 employees. There's plenty of people I don't know that can happen in that scenario. It's when I'm touching real talk. If Tyler today, this is perfect that he's here and you're connected to him. If Tyler. And you'll watch how he reacts to this. If Tyler got an email from our pet team. People in Experiences team. Because I don't even like calling it hr. Cause I think it's so bad that term. If he got HR and they drilled him, it would be so out of left field. And he would wonder, why did I let that happen without a warning? Cause we're close enough of that. And that would end the trust that him and I have right now. It would change our relationship. So I couldn't do that. That's not the right thing to do. But what I was doing was even worse. What I was doing was worse. I wouldn't let HR do it, but then no one did it. And then what would literally happen is, like, in six months, I'd be like, ty Ta Tai Ty. You know, we're at the end of the road here, man. Like, you know, like, you stink. You know, you're doing all these rap videos, like, right? And the person didn't. And for a long time, I blamed them. I'm like, fuck this person. I fucking had them on my payroll for two extra years while he was doing his rap video. I know I'm on this kick now, but, like. And so I would blame them. I was not accountable. And I could have. And you know what really breaks my heart? I could have fixed it for everyone. That's what. I'm intoxicated now. With kind candor, I've been able to course correct for people, and now they're gonna have great careers. Now I see it as a way I can really help. So that's really changed the paradigm. Before I used to think it was a way to scare people. I thought it'd be like, hey, you gotta shape up. I thought he'd be walking and basically be on LinkedIn an hour later looking for a new job because he was scared that I told him he might be on thin ice. Now I see it very differently. Now I see it as like, he's gonna be happy with me, that I'm giving him an opportunity to address it. We had a major one happen in the the LA office in the last three months. A very senior person. It's shocking, the kind candor from me and other leaders. Like, that person's on the complete other side of the pit. Like, not even the same person. So it's exciting to see the benefits of doing the right thing.
B
You invested in some of the biggest companies ever back in the day. How big of a risk did you take? What are some of those companies and why did you invest in them? Like, what point of your career were you at when that happened?
A
When I invested in Facebook and put $200,000 into it, I had $234,000 in savings, and I was paid under $100,000 from ages of 22 to 34. Even though I built a huge business for my father because it was an immigrant business, and you don't get paid it Was a catastrophic big bet that I did not think was a big bet at all. I was 100% sure that Facebook was going to be monstrous. Not even 99.
B
Why?
A
It already was big. That's it. That's the truth. It's not like I met Mark when he's like, I got an idea. It was a couple years later. It already had tons of users. Every school that went like, here's why. It started in Boston, obviously. My brother, which was lucky for me, was at bu, freshman year of Facebook. So BU got it, like fifth. And my brother's like, yo, there's a new app. Cause we were already into tech a little bit. I was watching library tv. Like every kid in my school's on it within the first hour. I'm like, oh, interesting. You know, So I already kind of knew it from that frame. You know, when you're watching. It was. I already believed in MySpace and knew MySpace well. I was interested in how Facebook was causing the rest. Like, I knew I couldn't be on Facebook. Cause it was just for college kids. I thought that was smart. I know how young I was. Yeah. And I was 30. So I just got out of the era a decade ago of how kids think about things. Like they don't want anybody older on it and how cool culture works. I fully believed in social media already. Even going further back than my space. I don't know if you guys know this. There was a site called Friendster, which was before MySpace, Tumblr. Right after that, I invested in. That was middle school culture. Not even college.
B
Was there any return on Facebook by that point that were like, yes, Tumblr. Like, where's the Vaynermedia started?
A
No, the reason I was. So I invested in Twitter. 43,000. 40,000 into Tumblr at that point. It was one year later. So I had a little more money. Tumblr. I might have invested in Tumblr after I did my first book deal. So I got some money from a book advance off a viral video on YouTube of a keynote speech.
B
What was your first book deal from a viral video?
A
That's right.
B
Did not know that.
A
Yeah, I don't really. I don't say it that way because the truth is, it wasn't even from the viral video. Let me say it a little bit different. Maybe the third speech I gave in my life was that Javits Center. It was called Web Expo. I think it was 2008. And I went on stage and I'll never forget this. I told two people that I was in the green room, I'd never had this feeling in my stomach. It was like a mix between very nervous and very confident. I could feel I was feeling different. And so I said to Jason freed from 37signals, great founder, and Fred Wilson, one of the iconic New York City VCs, I said, I'm about to go on stage and something very good or very bad is about to happen. I could feel it. And I went on there and I was in my, like, Richard Pryor, Eddie Murphy, raw. Like, I was in it. I was 11 out of 10 and I was spitting good shit. Like, all stuff that became true. And by the time I went home, back to the wine store, when I say home, the audience office, like, literally went back home because I was still working in Jersey, even though this was in New York and I was living in New York. I had three different emails from publishers that were in the audience.
B
Wow.
A
I took meetings and I signed a very big deal with HarperCollins. And then I wrote Crush it, which changed the course of my life. This summer, serve up the cookout classics. Heinz ketchup and Kraft singles. Every good burger needs, needs a layer of perfectly melty cheese and thick, rich ketchup. We all know it's not a cookout without Heinz and Kraft. When you need to build up your
B
team to handle the growing chaos at
A
work, use indeed sponsored jobs.
B
It gives your job post the boost it needs to be seen and helps reach people with the right skills, certifications and more. Spend less time searching and more time actually interviewing candidates who check all your boxes. Listeners of this show will get a $75 sponsored job credit@ Indeed.com podcast. That's Indeed.com podcast. Terms and conditions apply. Need a hiring hero. This is a job for Indeed Sponsored jobs. And everyone references Crush it from back in the day.
A
Yeah, Crush It. Like, it's so humbling watching, like the biggest creators and personalities, like just how many people talk about Crush it being the book that, you know, it was a multi week, you know, very successful New York Times best selling book. If you read it now, you would shit like I predicted, right, Matt, you just read it. It's crazy, right? I predict live shopping in basically lays out the entire creator economy. It speaks about this. What's happening. You have to remember, you guys are all youngsters. There was no Internet fame when I went on Conan to do my wine thing in 2007. This is. Look at the goosebumps I'm about to. I don't know if you guys can see this. This is real. What I'm about to tell you. It made the front page of Digg, which was like. That was like Reddit plus TikTok plus Twitter combined made the front page of Digg. Everybody from Perez Hilton, who was one of the only known bloggers when I. Every person on Twitter, I was trending on Twitter. Everybody on the Internet was cheering for me, literally saying things like, gary Vee, do it for us. That's how small the Internet personality community was in 2007. Like, it was a different time. So that book, in fact, when I wrote that book, I took a lot of heat. People said I was a snake oil salesman. I. There was like quotes on the Internet. Things like, this fucking asshole is trying to convince you that you're gonna make $50,000 a year on YouTube. Think about that. I know. I love your guys react. Think about that. So, yeah, I'm very proud of that work. You know, as I get further away from that work and as that work, that book, what I said in it, becomes more and more true, it feels more significant to me in my history, of my career, more today than even three, four years ago. Because y' all will go, now look at that. And like, skim it and be like, Jesus, you know, I was 10. And he was like talking about, like influencers and podcasts and live stream. Like, how. Because it didn't exist yet, by the way, Matt, I know you just read it. I don't say influencer or creator because the term didn't exist, right? It's not reference. Like the term didn't exist, bro. What'd I say? People. Entrepreneurs. Entrepreneurs, yeah.
B
You are very well known for making predictions. In fact, 10 years ago, you did an interview with Larry King that I watched, and he asked you, what social media platform should we pay more attention to? And you said, music ly not even musically at the time. So that what I wanted to. What I wanted to ask for you with that is why did you say musical ly back then? And what platform or thing should we pay more attention to now?
A
Got very lucky, especially Larry King. So cool that. So the answer to your question right now, if you're not paying attention, people should know what substack is. But I would say it's the one that people are not using that a lot of people should be using. I would also say that Snapchat, Spotlight. People use Snapchat. They don't use the TikTok Instagram of Snapchat called Spotlight. I would say there's nothing else. And oftentimes because I've been asked that question for the last 10 years, the answer is nothing. And I would argue the two things I just said are not new. Snapchat's been around forever. There's a nuance within it. And again, substack should be known, but I know a lot of people don't know it, so I hope that helps. If you're a writer and you just heard that, I think I just did something really good for you. So good luck. Go download it. Musically had already happened. Like I'm always, always paying attention and hoping something pops up. Again, like I'm always watching musically, it already happened. An extraordinary amount of 14 year old teenage girls were making videos.
B
Yeah.
A
And boys. But even when I, when Larry, like, look, it was really, really girls. And then in 15 it was boys. Like, it start like I watched it and then I was like, oh, because you know, I am who I am. I knew Facebook started as college kids. So when everybody was saying to me, you're wrong about Musical Ly, it's just teenage girls. And I would tell like 40 year old businessmen you're gonna be on it one day. They're like, what are you talking about? I know how youth can culture drives. It's the tail that wags the dog. I'll tell you why I actually believed in it. It's because of Tumblr. Tumblr was the app I invested in that was based on following things you're interested in, not who you follow. Right. All of you, you guys are the right age. You were into the art you liked or the photos or the skateboarding. You were into a subject, not a person. And I call that the interest graft in my head. People, not social media, interest media. When I saw Musical Ly, I'm like, wait a minute, you don't need followers, you're posting and people that are into dancing or cooking, like the content's finding the audience. And then I became aware of what was going on in Asia and what was going on with TikTok. I'm like, this is it. And then obviously TikTok bought musical ly to continue that process. And here we are.
B
Yeah. A lot of time has passed since you've said that and you've talked about like for content creators to not be emotionally attached to content. But my question is, oftentimes as creators or artists, income can be predicated on views on engagement.
A
Yes.
B
Because of this, would you recommend to build businesses and income outside of views and engagement as creators?
A
Yes, if you're capable. The problem is creators and influencers have become Synonymous with entrepreneur. And it's not true.
B
Interesting.
A
And vice versa. And this is where I think I'm part of a smaller subset. I am both creator and influencer and entrepreneur. I was entrepreneur first. I didn't become creator until I was 30, which is wild to think about. I didn't have the. Even the ability to the point platforms didn't exist. I would love anybody that has 100,000 followers for their get ready with me makeup stuff or skateboarding or video game. I would love for them to be capable to start a business selling skateboard equipment or swag or a coffee that they want to start. Like Emma Chamberlain did. Right. I'd be pumped if people could do that. I just know it's hard. Like 99% of businesses fail. I would love people that can start businesses, people that are selling $15 million of Mittens or of deodorant or of sneaker soles that they invented. I would love for them to be great at content creation because it will drive their business. I'm just aware that both of them are profoundly important skills that are rarefied air. And it's hard to be bothered.
B
You talk about attention being the main asset. Once someone. Actually a lot of creators develop a skill of getting attention using hooks, making content. Once they get attention, what do you think they should do with it? Is it just about continually?
A
That's a great question. My preference is for them to build depth with their audience.
B
Okay, this is great. This is great. How do you build depth with your audience?
A
Talk to them by loving them, by caring about them more than what they give you? I will tell you the biggest reason, almost this is actually profoundly fun to say everybody. The number one reason it's not happening for you. And that's pretty much everyone. Like almost everyone, especially under 25 right now, 22, everyone's taking a stab at trying to be famous. The reason it's not happening for you is everything you put out is in your own self interest. I want to get followers from this. I want to get money from this. I want people to like me because of this. You give absolutely no thought to what's in it for them. I want to look beautiful. I want to seem cool. How does I want to take a picture on my left side because I look more handsome that way. Like everything's about you. I know the reason I got here, every single piece of content from that first wine review. When I sat down and I drank that wine and I sat just like this. I remember it like yesterday. All I thought about was, I'M gonna taste these wines and I'm gonna teach them and tell them the truth. That was the wild thing I did. This is the wildest thing I did, was my. My best friend who was running the business with me, my cousin who was running the business with me, and my father literally thought I lost my mind. Because in episode four or five, I'm tasting a wine that we sell that is literally, literally downstairs, stacked to the ceiling. And I'm like, this wine's crap. It's thin. It's off balance. And like, they saw it. Cause they thought I was doing qvc. But you weren't selling what I. And I, by the way, the first time I thought about it, I thought I was doing qvc. I'm like, oh, let me make videos to sell wine. And something happened. I mean, I'm looking at it right now. That little red button. The first time I'm like, wait a minute. What if I tell them I like this and I don't like it became very real very fast. And I was trained to bring value. My obsession was to make the world, like, enjoy wine more. You know, this. Probably all of you know this wine's funny. Like, if you have a buddy who knows wine, they're like a douchebag about it. Like, oh, you don't know. You don't want to smell it. And I loved wine, but none of my friends did. It actually wasn't the era like. Like, it's crazy. You guys won't even know this. For all of you, There was nobody 20 years ago, under the age of 40, that liked wine. Maybe if you were in a very rich family and it was in the culture, but not normals like us. Like, you know what I mean? It was just like, no way beer. Like, no way. And I wanted kids my age to like wine too. I made the show selfishly at some level. And I wanted to make wine cooler. I wanted to de un douche ify wine. I wanted to give people to try different wines. Cause there were so many different wines to taste. It was all about them, bro. And then when I started talking about business, it was all about them. You can get famous on the Internet. You can start a business. You don't have to hate your nine to, you know. And this was the early stuff. Even before you might have even caught me, it was like, you don't have to find fucking unstable scan and staple. This Internet thing is gonna give us an opportunity. And that is why now, look, some people bring value. Cause they're a fucking smoke show. And People like looking at them, they're hot. Some people are funny as fuck. Some people are super intelligent and it's like nerdy. Some people are really good at reviewing music and we enjoy their perspective on it. Some people can interview like value comes in a lot of different form. But are you about value in giving it or are you looking to extract and you want the riches from it?
B
Even that being the case for longevity purposes, to be in this industry for a long period of time, would you say that storytelling is the most important thing?
A
No, but I think I understand what you're saying. I think it can be one of them. I think storytelling is an important remarkable skill that can keep you very, very relevant. Right? Especially if you can tell net news stories. If you're Steven Spielberg, like, you know, like yes, I would say value. And like value comes in different. Like I can speak for myself. Five years I was just bringing value to America about buying better wines for cheaper prices, making wine fun. You know what was a big one? Having a lot of young kids find something to do with the their father. That was huge. I mean here it is again. The goosebumps. The amount of people that have emailed me in my life. Young women was a big one. Hey, I want to thank you. Your show gave me and my father something we both liked. He was a sports guy, wasn't into it. He was always with my brother. But we connected over wine library tv. And I just want you to know that meant something to me. Like you know, like that was value. Other people like, you know, like got became sommeliers because that was value. I did that for five years. Then I became started talking about business. Gary, right? My value then was do this, make do these ads, set up this account post. It was very detailed, very specific advice. That was three, four years. Then I realized nobody was doing it. Even though I was making all the this content get millions of views. I'm like wait a minute. Insecurity, mind perspective that I started bringing value of like your life can be good now. I get emails and stuff by people that are like, you saved my life, you got me out of alcohol value. Some people love me because I got them to collect Pokemon cards again. Cause I talked about that in 20, 18 and 19. These cards are coming back. That was value. I get emails every day from, from 48 year olds saying you brought joy back into my life. I jumped on it because I thought I could make a couple bucks. Now it's the thing I collect with my son and I have happiness or I started a Card shop. Like people back to music. People email me saying thanks for putting me onto Gunna early. Like that's real emails in my inbox. I had Gunna in the office early on in his career. Like I had a whole range there was. I was doing unsigned hype freshman 15 for like four years of my career. Had unlimited under on the come up artists. People have asked, you know, said like value comes in a lot of different things. I wouldn't say it's storytelling. I think it's bringing value.
B
Do you think you can build depth with the audience through like online platforms that are there? Do you think you should take them off?
A
I prefer to take them off.
B
Where would you put up meetups in person? Irl.
A
Irl. I love IRL zooms. Like group. Like everybody here who's trying to build something should definitely do their next post saying there's a link in my bio to a Google hangout next Thursday. I'm gonna be on from 9 to midnight. Come and hang out with me and ask questions. Everyone should do that. They will build depth. You know this I think because you've done the research. You know I replied to every single tweet I got from 2007-11. Yeah, I built my entire career on depth. In fact, the follow up book to Crush it that I wrote that was also New York Times bestseller was called the thank you Economy. Like good old fashioned 1950s principles. Thank you. You're welcome. Hello, Shake your hand, look in the eye, AKA give a fuck about the other person. Reply to every comment. Do you know how many people are trying to grow brother? And don't even reply to the comments or DMs they get and they have seven of them. We have gotten to such a level of entitlement and selfishness that you have people that are desperately trying to become the next Sydney Sweeney, the next King Bach, the next Marcelo Hernandez. And they get nine comments on their little skit and they don't even say thank you.
B
You've said in the past that every time you post on social you're trying to win.
A
Yes.
B
What does winning mean? Providing value.
A
Yes.
B
How do you so you provide value when you think about the audience and giving them.
A
I'm gonna say it again. I do not even know how to to post something, by the way. I don't post about my private life. You know that like I don't think that's valuable. Here I am on a boat, you know this. I've done well in my life. You guys know this. I don't know if you know who I am, or like, you're not gonna see pictures of me, like, here's my Rolex. You don't see me on the private plane. I'm not trying to flex on anyone. I do not understand anything other than value. I think it's the most tried and true thing that people can do. And I think people should do more of it. And by the way, I'm gonna say this. Cause I'm a little bit too absolutism. It's okay to sell. You're allowed to. First of all, who the fuck am I? I'm not God. You can do whatever the fuck you want. I'm just talking about what is sustain. I'm answering your questions. How do you build? How do you be sustainable? How do you be long term? You bring value. Or you have some hits. I mean, in music, it's wild. You have a good run, you can play on those 13 songs for the rest of your life. Even one, it's epic. That's why I love music. I'm pumped for people. One hit wonders. Can live forever. Like, it's different kind of venues. You gotta have some humility. You used to do, you know, stadiums and now you're like in a lodge. But those 40 people on that one hit will fucking bang it out word for word. And that feels good.
B
You work with a lot of different brands. Have you ever had frustration when brands you work with don't follow your advice?
A
I'm gonna give you some flowers. I'm really proud of you asking that question. That is a question that I've really not been asked a lot. And it's a really funny answer. You ready? I don't think I have a client yet 15 years in that fully listens to my advice.
B
Wow.
A
How about that? One thing that won't make sense to you guys because you live with Gary Vee on the Internet. And this is Gary Vaynerchuk on Madison Avenue with the biggest companies in the world. They still don't fully believe in social media. Still. Yeah. Like you have. You have no, most biggest companies that, you know, Nike spends more on billboards and direct mail than social media. Like the biggest companies, you guys know.
B
That being the case, though, you have never done a sponsorship with social media.
A
That's right.
B
Why?
A
Um, value a little bit. Well, the jab, jab, jab thing is for everyone. I wrote the follow up after thank you Economy. It was called jab, jab, jab, right hook. Give, give, give. And then you can ask like, I'm not scared. Like, I'll give a plug right now. Winetex.com. i want everybody to buy their wine from my dad. I also think Winetex is the best way to buy wine. It's like, really good deals once a day on text. But I. Yeah, I mean, I have not gotten an offer that is lucrative enough. First of all, I would never pitch something I don't believe in.
B
Yeah, yeah.
A
Now, by the way, I don't judge influencers who do. I just am in a place where I don't have to. I can afford to. Not like, I've had plenty of things like, well, give me $500,000 to post this. I'm like, that's toxic. Like, diarrhea stuff. Like, I'm not doing that. Like, you know, so I don't have to comma. I would, like. Let me think of a good one. Captain Crunch cereal. I love Captain Crunch cereal. If Captain Crunch said, hey, we'll give you $3 million and we gotta do something really creative. Not like a post. I'm like, me, like, you know, like something cool. Maybe like a wine event. Pairing Captain Crunch with. With wines. And like, something that got me going. I'm not against it. I just don't look for it. Say no to everything. And I do business in a different way. But, you know, it's funny. You catch me at a time where I am starting to. I am starting to get weird offers where, like, people want me to be, like, in a national commercial and on billboards. And that's kind of funny to me. So I'm like, hoping like, a B2B company, like something boring to you guys, like Adobe or when you're in the. You guys know when you go on an airplane and there's all those. The signage on the. Because I fly so much, I'm like, I do that. I'd be like, hey, it's me. VaynerMedia uses Salesforce. I would do something like that. Something a little dorky. That is really just an inside joke for me, myself and I.
B
You talked about how you didn't do a lot of vacations back in the day.
A
Yes.
B
And me personally. Personally, I took my first ever vacation in seven years. I just got back from it now.
A
Nice. Good for you. Where'd you go?
B
I went to London in Paris with my brother.
A
That's awesome.
B
It was really great. Got to see family out there that I had.
A
Oh, that's awesome. Good for you.
B
That being said, though, a part of me feels like the pole because I had to miss the Oscars. I Had to miss south by Southwest, those types of of things. And like taking vacations and having that like pull and dichotomy. What's your advice on that?
A
I don't struggle with that. I like taking vacations. But to your point, I don't take them when there's like things like that. Like if there's like. I don't take them during like super bowl when that's a business thing for me. I love late August cause the whole world shut down.
B
You work your schedule.
A
I work my schedule. I also have two children. So there's a lot of the school dynamics. There's some of that. But yes, ingestion in general. I don't take vacations when the world is active. I love the last two weeks of the year. Like you know that Christmas, New Year's. I'm obsessed now with the last two weeks of August. Cause America's become a little like Europe and we're kind of like bougie and just chilling those last two weeks. I love a good Thanksgiving week because Americans have gotten soft and we don't even really work on Tuesday or Wednesday, let alone Thursday and Friday. So it's like kind of the world is only really on on that Monday. So I'm like, that's awesome. And actually in fact I just said to myself, you know what, I'm gonna do better next year on the four day weekends. I'm a work on the four day weekends guy, Columbus indigenous or presidents or like I never do that Monday, Tuesday thing. But I want to next year. I want to be able to spend some more time with family on that four day weekend and work it in. I'm working so hard so I effectively so productively most of the year. I want to find more pockets, but I would struggle given that I have so much responsibility to do, to your point, a random week. Because my problem is if I take a random. If I take next week off, do you know what happens in my life? I come back to a disaster. So I'm stressed the whole fucking week that I'm off, that I'm coming back Monday and I'm dead. I missed every day at school. Cause there was. There's nothing to come back to. This is awesome by the way. If I worked somewhere I would take off all the time. But for me, cause I'm at the top and I'm the entrepreneur and I'm the owner and the operator and I have responsibility and I could be on call anytime. Like God forbid something terrible could happen. Like our building could have a Fire in our Thailand office. I'm never really off. I'm in firefighter mode. So what's nice about, let's say the week before Labor Day is when I am off that week. Even if I'm checking it just a little bit, there's only so little that's building up because everybody else is chilling. In fact, if we can all put our hands in right now, 8 billion of us all in the pot, everyone put their hands out that the whole world is on vacation in July, I'd be pumped. Pumped. Fuck it. July and August, I'd be pumped like ready. Three day work weeks, fine by me. It's just that I can't be off when it's on because it's a heavy cost.
B
That makes sense.
A
Yeah.
B
You said something that was really interesting during one of the interviews. You said you're trying to become one of the greatest entrepreneurs of all time. My question is, how do you know when you've done that?
A
I will never know. It'll be subjective. I do not believe making the most money makes you that. I don't think Elon or Bezos or Zucks are that though all of those guys have created profoundly interesting companies. The way I think about that is I'd like to inspire the most positive entrepreneurial behavior of all time. Back to the sandcastle. I would like to create the most entrepreneurs or help the most entrepreneurs and help them from a mental health and lack of anxiety and enjoying entrepreneurship the way I do, comma. I'd also like to build some of the biggest businesses of all time. If I build veefriends into Disney or Pokemon, I'm in the mix, you know, like especially with all the other stuff. So, you know, I want to challenge myself. Like the game how good of a skier am I? How good of a skateboarder am I? How good of a video game player am I? How good at basketball am I? It's that me versus me thing. And then I think I've been a pretty bright voice in entrepreneur. I think I'm unique in the last 15 years of entrepreneurship. I think I do talk about things differently, subtly, and I'm proud of that. And there's others that do too. But I feel happy with the deposit that I've put into the world and I'd like to do more of it. And I think, you know, unfortunately I feel like what I preach is needed even more now than five years ago. And I'd like it to be the other way. I'd like the world to get a little less anxious And a little lighter. But like, I feel a sense of responsibility, of talking about love and hope and optimism. But you know me, accountability. Like, I'm not here to coddle. Like, it's not charity. You know, there's a reason there's something called charity and there's a reason there's something called entrepreneurship. And they're different.
B
I also feel like it's interesting for Veefriend specifically to go the similar route of Pokemon at Disney by cause kids connect with what they are kids. And when they get older, it becomes nostalgia.
A
Yes.
B
And I think that that is incredibly smart because you said, I've always believed that nostalgia is one of the greatest assets of our time. And I think that you've said that in the past and it's very interesting of how you're going about it. And I think once the stories of all these individual characters come across, I
A
think that's where we're gonna connect. That's why the comic. If you're a comic fan or if you're into anime or manga or nerd culture, please, please go to vee friends vefriends.com comics. You'll see how I'm starting to develop it. And by the way, this is a. By the way, back to you liking music. I'm about to tell you the coolest thing that's about to happen in my career. People don't think of me as a creative. Like not an influen. Like I am inherently very creative. Like these comic books, these origin stories. Like I'm a real storyteller. Like really not seen to the world more in my family. Like, I'm excited about it. I think people that are into comics, culture or character development when they read these comics, I think they'll be impressed and I think they'd be stunned of how much of it comes out of here.
B
Speaking of not being seen as a creative, do you have any advice for anyone out there who wants to be a creative?
A
Well, I mean, it's practice. I mean, again, I think self awareness is huge. Like, I think one of the reasons there's so much anxiety in the world is a lot of people want to be what they want to be. Not being self aware of who they are. Like, I also listen, I want to be the quarterback of the New York Jets. Let me very clear. I want to be. I want to be the quarterback of the New York Jets. I am not the quarterback of the New York Jets. Right. And so I think that, you know, if you want to be a creative, let's start with what I grew up with, which is closer to the music stuff. And now we're in the entrepreneurial era. When I was growing up, kids wanted to be rock stars. Yes, they wanted to be rock stars.
B
Bad.
A
And I listened to a lot of bad music in middle school and high school of my buddies who thought they were gonna be fucking Axl Rose. And then hip hop started to really come or die. Dr. Dre or Snoop Dogg.
B
Pop stars.
A
Yeah, yeah, definitely. Pop stars were so big. Michael Jackson, Prince, Madonna. I mean, they were the OGs. And then, you know, into Britney and all the boy bands of the late 90s, you know, and then now what's happening with entrepreneurship and influencers? People want to be an influencer. People want to be, you know, an entrepreneur. Here's what I would say. If you're creative and you're listening and you. You're shy, which means you're potentially insecure about people's judgment about your paintings or your drawings or your music. I don't know. Like fucking Mark Twain. It like, hide behind AI. I don't know. I don't give a fuck. Like, get your shit out. Get your shit out. Create account. That is not even looks like it's. You just post it if you feel so bad. If people think it's dumb or stupid, hide. But fucking get it out. And then you'll unhide once you realize there are people that like it. But if you're delusional in your creativity, listen to the audience. The audience is the only one that's right. Not even you.
B
Do you think there's a point where you're early and the audience may not be the right audience as a foundation? Yeah.
A
That's called conviction and patience. Sure do. I sure do. I think conviction and patience. But I think there are many people that are still putting out rap songs on SoundCloud nine years later, and they still can't break a thousand listens. It's like, hey, man, there is a place. And by the way, if you enjoy doing it as a hobby, that's amazing. But if you're literally telling your boys you're the next Drake, and we all see that, right? You gotta get out of doors. Delusion, you know, optimism is amazing. Delusions of vulnerability.
B
Behind the Wall.
A
That was a good one, right? You like that? That was a bar, right? I agree.
B
Behind the Wall was started with the goal of inspiring every underdog to go for it. As someone who was making videos in their room with an iPhone, recording their laptop screen, made 5,000 videos before having the first Interview or got to interview some of my musical heroes like Ryan Tedder, Coldplay, Benny Blanc.
A
Go.
B
And now having the chance to talk to one of the first people who was like, go post on TikTok is so incredible, and I'm so grateful for this opportunity. I wanted to start something new.
A
Okay, nice.
B
I don't have a name for it yet, but I bought a paver like a brick.
A
And I'm is.
B
I want to start a thing where whenever I get a studio in the future, maybe not maybe just in the home.
A
Yep.
B
For the people that I interview, I want them to, like, leave a quote, like a message, a piece of advice, and then sign it.
A
Thank you. I'm humbled. This is the actual wall. The name of this is the actual wall. Not behind. Fuck, man. This is. I'm actually strong these days. This is heavy.
B
I have Sharpie or.
A
Yes, I'll go Sharpie. See, I'm gonna go with green. That is my color. Oh, this is white. What's going on? What's going on here? Let's go. Okay, no worries. I wrote Always say maybe, something I've been thinking a lot about recently. I believe that the world is now filled with unlimited people that say no to everything. That cynicism is having a very good run. And I hate cynicism. And I think fear and insecurity, judgment and envy and jealousy are leading so many people to know. And I would say to everybody who's listening to this, especially now, I'm getting more of a sense of you. I'm pretty excited about this because I have a sense there's a group of people that listen to this show because of you that were similar to where you used to be or things of that nature. You at some point said maybe, right?
B
Yeah.
A
Yeah, right. There's no way we're sitting here without it. And I would just say that everybody is saying no to things. I'll give a good one, especially looking at some youngsters. Do you know, all of you, all of you were scared to ask someone out or, like, hit on someone or say what's up to someone? And actually, one of those people would have said yes, and that is now lost. And if you would have said maybe and did it, yeah, you'd have some memories of a bunch of rejections, but they would be all offset by the memory of the one yes, saying maybe with the hope of yes versus saying no, which means immediately it's a loss. Saying no is an immediate loss. Saying maybe is just stories over beers when you're old. More importantly, leads to the best yeses of your life. Always say maybe.
B
I love it. Thank you so much, Gary.
A
Thanks for having me. Such a pleasure. Congrats. Thank you everybody. If you enjoyed this podcast, please go back and look at the prior episodes. They're loaded. I appreciate your attention and thanks for being part of this. You can't reason with the sun. Trust us, we've tried. This summer, it's time to put that angry ball of fire on mute. Columbia's Omnishade technology is engineered to protect you from the sun's harsh rays that can burn and damage your skin. The sun is relentless, but so is our gear. Level up your summer@columbia.com to spend more time outside and less time slathering on aloe lotion. You're welcome, Columbia Engineered for Whatever
B
your next chapter in healthcare starts at Carrington College's School of Nursing in Portland. Join us for our open house on Tuesday, January 13th from 4 to 7pm
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Edu Sci Journey. See you later.
Podcast: The GaryVee Audio Experience
Episode: How to Give Value and Win in the Creator Economy
Host: Gary Vaynerchuk
Date: June 22, 2026
This episode features Gary Vaynerchuk in a dynamic conversation about value creation, authenticity, and navigating the evolving landscape of the creator economy. Drawing from his early days as a content creator and his journey as an entrepreneur, Gary explores the critical differences between building from love versus insecurity, the necessity of community and candor, the tension between attention and depth, and actionable strategies for creators and entrepreneurs aiming for long-term impact. The tone is personal, practical, and motivational, with Gary’s signature directness and contagious optimism.
“I’m building the sandcastle for me on this sunny day, quietly by myself. … I’m not looking for outside validation. It does not give me self esteem, nor does it not give me insecurity. And I’m playing my game.” (A, 00:06)
“I am the vase that my mom created. … My father did one very important thing… he scared the bullshit out of me [about honesty], and I really thank my father for that.” (A, 14:50)
“The number one reason it’s not happening for you… is everything you put out is in your own self-interest. … You give absolutely no thought to what’s in it for them.” (A, 55:51)
“When you get somewhere because of darkness, when you burned people along the way and stepped on people, … it’s not sustainable ... eventually it gets suffocated and burns out.” (A, 18:20)
“I do believe in the human spirit, bro. I believe humans can change, but they have to take big action… You gotta pay attention to the people you’re around, including your parents…” (A, 19:29)
“Competitiveness is fake, meaning it’s momentary… Insecurity, which often leads to envy and jealousy, is you always want to rip the person’s face off. It’s sustained.” (A, 23:15)
“Everything bad in my personal life, relationships and professional life, was my inability to not be canderous. Building up resentment and then leaving … but I could have fixed it for everyone.” (A, 37:44–43:39)
“You know how youth culture drives. It’s the tail that wags the dog. … I was always watching… it already happened. An extraordinary amount of 14-year-old teenage girls were making videos.” (A, 53:45)
Advises creators not to tie their income solely to views — entrepreneurship and true business-building are different skills than content creation (54:08–55:28).
“Creators and influencers have become synonymous with entrepreneur. And it’s not true.” (A, 54:17)
Success in attention economy:
“I built my entire career on depth. In fact, the follow up book to Crush it… was called the Thank You Economy.” (A, 62:15)
“I have not gotten an offer that is lucrative enough… I would never pitch something I don’t believe in.” (A, 67:16)
“I would like to create the most entrepreneurs or help the most entrepreneurs and help them from a mental health and lack of anxiety and enjoying entrepreneurship the way I do…” (A, 72:08)
“If you’re creative and you’re shy… get your shit out. Create account… post it. If people think it’s dumb or stupid, hide. But fucking get it out.” (A, 76:07)
Sandcastle Mindset
“I’m building the sandcastle for me… not for people to take a picture of my sandcastle.” (A, 00:00, 06:52)
Love over Darkness
“A smaller group… get to the top on a pure love train, on some Yoda shit, on some Obi Wan stuff.” (A, 17:50)
On Building Others Up
“There’s two ways to build the biggest building in town… be so good… or tear down everybody else’s building so your little fucking building seems like it’s the biggest.” (A, 24:40)
Biggest Reason Creators Don’t Break Out
“Everything you put out is in your own self interest. …You give absolutely no thought to what’s in it for them.” (A, 55:51)
Value as North Star
“I do not understand anything other than value. I think it’s the most tried and true thing that people can do.” (A, 63:58)
Always Say Maybe (His inscription for the show’s "brick wall" legacy project)
“Saying no is an immediate loss. Saying maybe is just stories over beers when you’re old. More importantly, leads to the best yeses of your life. Always say maybe.” (A, 80:19)
This summary distills the wisdom, actionable strategies, and motivational ethos of Gary Vaynerchuk as shared in this episode, providing a comprehensive guide for aspiring creators, entrepreneurs, and anyone navigating the creator economy.