In short
Gary Vaynerchuk argues that the loudest online voices are often mean and insecure, and that the next era (next ~5 years) will reward humility, truth, and kindness. He centers insecurity/fear as the main blocker to action, says regret comes from not trying, and claims reputation is an underpriced asset. He also predicts civility will trend back up, and discusses social commerce/live shopping (e.g., TikTok Shop) as a major opportunity.
Guest backgrounds
Gary Vaynerchuk is an early social-media operator (YouTube, Twitter, TikTok) and runs VaynerMedia, advising major companies. He’s built a large media/content engine and has worked across live shopping. Emma (host) is the interviewer.
Key claims
Insecurity (fear of judgment/failure) stops people; insecurity can start you but can’t sustain you. Confidence is “pure confidence, not ego.” Accountability is “start with yourself,” and modern parenting/trophy culture can increase insecurity. Kind candor + humility enable truthful feedback.
Notable examples
His childhood fears (parents dying), “nice guys finish first” framing, “Kind Candor” feedback approach, and TikTok Shop GMV estimate ($25–$40B).
Written by AI. May contain mistakes. Listen to the episode to check what was said.
Chapters
Tap a time to open that second in VOCultural Shift Towards Kindness
0:46 to 2:32
Discussion on the shift in online culture towards kindness and humility.
“the internet about three years before they're ready to hear it.”
Cultural Shift Towards Kindness
2:33 to 2:52
Discussion on the shift in online culture towards kindness and humility.
“This summer, shop the latest small space solutions at Bob's Discount Furniture.”
Overcoming Insecurity
2:52 to 4:21
Gary Vaynerchuk discusses the role of insecurity in holding people back.
“Well, I'm very, very excited about our conversation.”
Embracing Fear and Risk
4:21 to 7:10
Exploration of fear, taking risks, and the importance of self-awareness.
“There's just a million ways people can get out, but it is always words that start the process of action.”
The Role of Empathy in Success
7:10 to 9:08
Discussion on how empathy helps in dealing with criticism and achieving success.
“And I think the biggest regret is just when you don't try something, right?”
Navigating Accountability and Responsibility
9:08 to 11:16
Insights into the decline of personal accountability in society.
“I like having money for optionality and time, but I don't want stuff.”
Insecurity and Its Impact
11:16 to 14:01
Gary explains the relationship between insecurity and lack of personal responsibility.
“it was a teacher in fourth grade or a classmate or johnnypants47 on Instagram, I just know that if they're saying something bad about me, it's because they're in a bad place.”
Radical Self-Responsibility
14:01 to 17:39
Explore the importance of taking personal responsibility for one's life.
“Is it more fun to think it's the immigrants' faults or billionaires' faults or corporations' faults?”
Navigating Parenting Challenges
17:51 to 19:52
Discussion on the challenges of parenting in today's society.
“of college that bothers you so much that you want to speak on it?”
The Importance of Curiosity
19:52 to 21:04
Understanding how curiosity drives ambition and success.
“Listen, I couldn't agree with you anymore.”
Show all 30 chapters
Creating for the Joy of It
21:04 to 23:01
Reflecting on intrinsic motivation and the joy of creating.
“I watched this kid once build the craziest sandcastle situation I've ever seen in my life.”
Embracing Humility and Kindness
23:01 to 24:19
The role of humility and kindness in personal and professional success.
“But like, I don't, yeah, it's not like I'm cool guy and like, fuck you, two fingers up.”
Cultivating Self-Awareness
24:19 to 28:00
Discussion on the importance of self-awareness and how to achieve it.
“You know, and so if you're a marathon runner, not a sprinter, if you're trying to make a quick bag and get a private plane and go smoke weed on an island and do all this frivolous shit.”
The Importance of Truth and Feedback
28:00 to 29:50
Learn about the significance of truthfulness and kind feedback in professional settings.
“when it's like starting to really happen.”
Candor vs. Brutality in Communication
29:50 to 31:50
Explore the balance between honest feedback and delivering it with kindness.
“I struggled with candor for a long time in my career because I watched people use candor to be a straight dick face.”
Civility and Its Comeback in Society
31:50 to 34:00
Discuss the potential resurgence of civility and decency in modern culture.
“every five, 10, 15, 20 years, whatever it may be.”
Advice for Young Professionals
34:00 to 36:20
Gain insights on how young professionals can navigate their early careers effectively.
“over the next two to four years by being civil.”
The Value of Proximity and Visibility
36:20 to 38:30
Understand the importance of being close to success to learn and grow.
“Lions become better lions by hanging out with lions.”
Overcoming Entitlement in the Workplace
38:30 to 40:30
Learn about the danger of entitlement and the importance of hard work.
“And by the way, if you're such a whiz kid, go do it.”
The Future of E-Commerce and Social Trends
40:30 to 42:00
Explore predictions about the future of commerce and evolving social trends.
“because I've seen you speaking so much about the next trends and you predicted YouTube.”
E-commerce Insights and Predictions
42:00 to 43:15
Gary Vaynerchuk shares his insights on e-commerce trends and the differences in live shopping in the US compared to Asia.
“Y 'all just don't know about it at the level that you think.”
Understanding Consumer Behavior
43:15 to 44:44
Gary discusses the nuances of consumer behavior and how different demographics impact trends.
“Hispanic, and then you go into interest.”
Overcoming Fear in Live Shopping
44:44 to 47:38
A discussion on how fear of judgment can prevent individuals from engaging in live shopping and content creation.
“So there are so many people that listen to this podcast that think, you know, I've got something special.”
Self-Discovery and Empathy
47:38 to 49:56
The conversation focuses on self-discovery and how radical empathy can help individuals overcome judgment from others.
“You would be able to just wash straight over it.”
Adapting to Change and New Opportunities
49:56 to 52:14
Gary emphasizes the importance of adapting to change and recognizing new opportunities in the digital landscape.
“Do you think I got excited three years ago when I'm like, fuck?”
The Role of Parenting in Success
52:14 to 55:00
Gary discusses how parental encouragement shapes children's identities and future success.
“And unless you were in with those people, there was fucking nothing.”
Nice Guys Finish First
55:00 to 56:00
Gary argues that kindness and integrity lead to greater success than cutthroat competition.
“And so I think parents have to be very careful and thoughtful about what they're spending on positive affirmation because a young human will continue to gravitate that for a long time.”
The Need for Civility and Kindness
56:00 to 57:38
Explore the importance of civility and kindness in a chaotic world.
“What they don't know is how much they left on the table because nothing ever came to them because all of us other winners were like, fuck you.”
Choosing Empathy Over Anger
57:38 to 59:20
Learn how to respond to negativity with empathy and understanding.
“Everyone thinks the whole world revolves around them.”
Aspirations and Legacy
59:20 to 1:03:03
Discover Gary Vaynerchuk's professional aspirations and vision for his legacy.
“You know, Michelle Obama says this beautiful thing.”
Transcript
Automatic transcript. May contain errors.0:09So, something I've noticed lately and it's been bothering me. The loudest voices in the room aren't necessarily the smartest ones anymore. They might still get the views, they're getting them by being mean, by tearing other people down and by being the most aggressive person on the timeline. And honestly, I think a lot of us are quietly exhausted by it. My guest today thinks this era is actually about to end. He thinks the next five years are going to belong to people who are kind and have humility, those who have brought reputations worth defending. And he's not saying it because it sounds nice.
0:40He's saying it because he watches what's happening online for a living, and he can see the cracks forming. Gary Vaynerchuk has been telling people what's about to happen on the internet about three years before they're ready to hear it. Social, creators, attention, AI. He was early to YouTube, Twitter, TikTok, and now live shopping, which we get into today. He's been right enough times that the people that write him off the loudest are usually quoting him a year later. He runs VaynerMedia, advises some of the biggest companies in the world, and has built a media empire that employs thousands of people and a content engine that produces hundreds of pieces a week.
1:17Now, I know what some of you are thinking. You've heard Gary on other podcasts. You've seen the clips. But that is not the conversation that I wanted to have. I wanted to sit down with one of the few operators who's actually paying attention to what's coming culturally, not just what's happening and coming commercially. Listen for what he says about insecurity being the engine that gets you started and why it can't be the engine that keeps you running. Listen for what he says about reputation being the most underpriced asset on earth right now. Listen for the line about fear. I think it's the most accurate description of why most of us don't move that I've heard in a long time.
1:52And listen for what he told me he'd do if he was starting from zero today. That's the part you want to write down.
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2:52Gary, welcome to Aspire. Thank you for having me. Well, I'm very, very excited about our conversation. And I feel like with you and I, the more research I did about you, the more similarities that I found you and I had, which is kind of unsurprising, but there's something that you said that really got me. And you said, and I believe this so deeply, you said everyone's got something and every person is carrying some version of hardship, but there's a choice and we all have a choice, whether you weaponize it as an excuse or you use it as a foundation for something, which you and I clearly have in our life.
3:25But I kind of want you to start at this point because I feel like so many people believe the stories that they tell themselves, the realities of the existence that they're born into. And I wanted to ask you what you really believe is the one thing that holds people back the most. Insecurity. You know, at its most basic, fear. It's why so many people weaponize it. It can control people. So I think the number one reason people are held back is they worry about the judgment of others because they're insecure, they're trapped, they're scared to fail in front of others, and they don't have self-belief because it was imposed inside of them through circumstance or someone.
4:07And I'm very motivated by putting out content and talking about it because every day people get unlocked, whether it's through therapy or meditation or a podcast or a friend or the serendipity of meeting a college roommate. There's just a million ways people can get out, but it is always words that start the process of action. But the answer to the question directly is insecurity. So what do you say to people that are living with real fear, like fear that comes from a place of real concern, perhaps that they don't have the circumstances that are best, but they really want to move forward in their life?
4:45Like how have you in your own life been able to do that? You know, I don't really use myself as a comp. You know, I'm the byproduct of an extraordinary mother and really, you know, humble beginnings, which is like the perfect formula for world domination. Yes, it is. You know what I mean? But if you experience fear, you must have it. Oh my God, my sister and I were driving here. We were just laughing that I got all my fear out of the way as a kid. I was ultimately mostly scared about my parents dying. It was a big, real big track in my life. My mom lost her mom at five. My father lost his dad at 15.
5:21So it was a legitimate fear. It was a legitimate fear. It was in the air. Yeah. My mom did almost everything right. But my mom would say things like, you know, if anything happens to us, you got to take care of your sister. And then later, my brother. I did so much fear in my youth and such real important shit that I think by the time I got to 18, I'm like, oh, we're cooking now. Like, I'm not scared of shit. I mean, that's definitely something we've got in common. And I talk about that a lot. I feel like I went through so much stuff that was actually scary. as I've come up in my professional life, stuff that would frighten the life out of somebody like - It's minor leagues.
5:54Losing money. I'm just like, that's not real. That's not actually something to be really scared about. That's right. But one of the things I've heard you talk about a lot is whether or not everyone should be an entrepreneur. I think that what holds people back so much is the fear. So how do you even begin to work through that in your own mind as a person? Whether you should branch out, whether you should be really entrepreneurial when the stories and the fear is really what's holding you back. By having a relationship with what's really important in life. I think a lot of people listening right this second know they want to take some sort of risk, but they are not willing to live less bougie if it doesn't work out.
6:34They're not willing to fly coach instead of front in the first class. It's almost like we've created massive taboo of taking a step back from a materialistic or social status that we're willing to not live our lives on what we want to actually do just to keep up with the Joneses, normally to impress people that we don't even really like. When you wrap up, when you start going to those 80s, 90s, 100s, you're not going to be happy that you didn't take those risks. You're going to regret it. And I think regret is a very devastating energy. We all have regrets. And I think the biggest regret is just when you don't try something, right?
7:18When you actually allow the fear to hold you back. How have you been able, as you've gone through your career, to get more and more comfortable with taking risks? Like, what does that actually look like? You know, I'm just so uncomfortably curious of how good I am at the game. It drives me. Whereas I've been in a place in my life now where I've spent a lot of time with a lot of people that are really at the tippy top. I was stunned when I got there. In what way? I was like, oh shit, they're insecure. I didn't realize that insecurity was the more prevalent fuel to get to the top. I thought, you know, I was such a cocoon of myself and my environment.
7:57I thought it was confidence. I thought, of course, you can get to the top with confidence, right? Because you're strong. What I didn't realize was insecurity gets you there as well. What I didn't know then that I try to talk a lot about now is insecurity gets you there. But it's also the reason you don't stay there, right? Yeah. You and I have been very fortunate to be in enough circles to know like Jesus Christ, some of the people that are the most admired people in the world are struggling. They're genuinely actually insecure. They're no different than others. What I've observed the last 15 years is it's hard to stay at the top of whatever you do through insecurity because you're constantly pulling from a very challenging energy versus what I have, which is I had content before I started, which did not take away any of my ambition.
8:51So what was it that drove you then? I want to make my parents proud. The only other thing I've ever said, which is true, is do you know like on porches, they have that zapper with the light and the bugs all go there and they get zapped? Oh yeah. I'm that bug. What the fuck was I doing when I was seven, knocking on doors in the summer, washing cars? And it wasn't about the money. It's not like I wanted to buy it. I don't even really buy shit. I like having money for optionality and time, but I don't want stuff. So how do you actually figure out? Because I do think that there is a whole audience of people that are listening.
9:26And I really believe that you can be entrepreneurial in a corporate environment, in like a regular job. But how do you figure out if the way that we're talking about entrepreneurialism now, starting a business, being a founder is actually for you or not? Jumping in the pool. Nothing to it but to do it. There's no weird test. There's no bullshit report. Isn't that what's so hard for people to understand though? You just got to do it. Yes, because they're scared to fail. But if you're scared to fail, it's already the first tell that you're not an entrepreneur. I think it's really important to contextualize like how important it is to eclipse fear and to have like moments of failure.
10:05Like I think of all of the sort of biggest moments of almost like lift where I've actually been able to propel myself forward. They've come after something has gone really wrong. Do you have those moments in your life, in your career where you've actually failed and something really great has come out of it? Mine's a little different. And I hope some people can associate with this. I just couldn't hear anything for so long. I'm 50 now. I don't think I've heard anybody else besides myself for four decades. What, you mean in your own head? Yes. You've been able to tune everyone out? Everyone. Shut up.
10:43Including my, even the ultimate, my mother, who's everything to me. How? I'm not sure. Well, because listen, I mean, you have put yourself in situations, you know, you're so huge on social. You have nonstop messaging, rhetoric, criticism, fantastic, you know, critique coming your way. How have you been able to do that? My best guess at this moment in my life is some sort of almost probably not even proper over-indexing on empathy. Please explain that to me. Anytime someone shits on me, whether it was a teacher in fourth grade or a classmate or johnnypants47 on Instagram, I just know that if they're saying something bad about me, it's because they're in a bad place.
11:27And how quickly do you go there? Like immediately as you're getting the shit? Really? And I got there. And I got, again, this is why I think about natural DNA a lot. Yeah, yeah, for sure. You know how there's like tennis players sometimes at 14 in the women's side, they can win Wimbledon at 14? Yeah, totally. That's just natural fucking talent. They put in some work, obviously, since they were six or five, but I think just naturally, and I get this from my mom. My mom also does not give a fuck. So I obviously have that, but like maybe it was the market giving me validation. You know, by the time I was 10 and 11, I was really slinging that lemonade and that shovel and those baseball cards.
12:08Like I was getting so much positive affirmation from the market. Somewhere between fourth and fifth grade, my head just went into some really fucking fantastic place that has been the foundation of my success and joy, which is completely predicated on simplicity, which is like, nothing matters. I'm going to do my thing, be a good person. See ya. So how do you get out of that? How do you give less fucks? Because I do actually believe it's a really important part of being successful that you start to drown out. I think it's the punchline. Right? Yes. Like a hundred percent. Yes. I would say that I've become infinitely more successful the less that I have listened to other people.
12:48And more importantly, and I need to hear, I need people to hear this because a lot of people are listening right now and they're saying to themselves, they're like, I'm successful, but I give a lot of fun. And what I say to them is like, yeah, for now, but I'm telling you, it's going to be hard to keep paddling and staying above water. When you get to that place, you're on the fucking, I don't know, is it the Dead Sea where you can just lay in your float? Like, that's where you try to go. Or maybe, you know, you launch a book and you get a lot of criticism, something like that. Like either or.
13:13You know, you're putting yourself out there, like your journey right now. And as you continue to ascend, it just comes with the territory. It's what the world does. We build up Britney. Then we tear down Britney. And then we want Britney back, bitch. It's just what we do. It's what we do. It's what society does. There's something else I want to talk to you about, which is you've been talking about so much, which is the decline of accountability. And I want to really understand what you think people are getting wrong right now when it comes to responsibility. Because I think it kind of links together with this conversation.
13:43They're believing politicians. Say more. Both the left and the right in every country in the world is selling the same thing. This is fucking you up. and I am going to save you. And you believe that people just eating that up, it comes from a lack of responsibility. Well, let's play it out. Yeah. You're unhappy, your life sucks. Yeah. Is it more fun to think it's the immigrants' faults or billionaires' faults or corporations' faults? Or is it more fun to think it's your fault? I just wrote a book called Start With Yourself. And one of the things I talk about is my upbringing was exactly like that.
14:15I was surrounded by people that blamed everyone for everything. And I watched an Oprah episode and it was about like radical self-responsibility. And I was like, that just sounds better. That just sounds like it makes more sense. Why do we struggle so much with that? And why are people being so swept up? Like, why is there such a lack of responsibility for themselves? Insecurity. You think it all comes back down to insecurity? I believe life is binary. Pure confidence, not ego. Ego is insecurity with makeup on. Confidence, insecurity. Show me where someone sits. I'll tell you everything about their life.
14:51And I believe modern parenting in the last 30 years has, out of good intent, this is a very important part of the sentence, at a very good intent, created more insecurity than historically. And we're feeling the effects of that as well. Why do you talk on this so much though? I find it so interesting because you do, like you come back to this point a lot. I see it. Yeah. Because I'm on the receiving and I'm watching it. I wasn't a kid who had this. I'm not doing any focus group of one. Remember, I've been a public figure for a long time on social and I talk about these things for a long time. I'm on the receiving end of literally millions of direct messages that are private at this point.
15:33And I analyze it. How much of that do you see? An extraordinary amount, especially in the last two years. Now we're taking all those messages and we're putting them into large language models and analyzing sentiment. Ah, so you're actually looking at everything. I used to, on a flight to LA like this, read four hours. And by the way, I still like to do it because I'm a little old school. Every now and again. Yeah, yeah, yeah. I still do it a lot actually. But I have much cleaner data. And so it's very clear to me that stripping competitiveness out of a child, demonizing competitiveness, demonizing merit, like she who's more talented and worked hard and won the soccer match should be treated the same way you and I should be treated, who did dick shit and gossiped on the bench and didn't give a fuck.
16:19What world is that going to play out well? That's why I talk about it because I think it's led to incredible amounts of pain. And it seems so small. By the way, whoever invented it, whoever, whatever woman or man came up with like, let's give everyone a trophy, came from a good place.
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17:50What I'm interested in is that what are you seeing in those children that are coming out of college that bothers you so much that you want to speak on it? That their parents tricked them into thinking like that work ethic and like that real life isn't real. Their expectations got whacked. But I do think it's an important subject to talk about because where we are right now, we really believe that there's so much danger, right? Whether it's social, whether it's society at large, we believe that we are there to protect our children. So you're right. It comes from a really good place. And at the same time, what we're saying is that we're in a market in a time right now where we are actually a little bit unsure of what we're even growing our kids up to do.
18:33You know, what is going to be left for them? So I understand where there's this fear around parenting. So I get it. I think that it's important to talk about like, what can we do? What is the way to behave? Build confidence and confidence can only come from what they do, not what you do for them. It's that simple, right? It's really that simple. It's really that simple. And it's really like, it's that simple and it's fucking hard. Yeah. No, I agree. It's hard because it's hard to dial back, especially when what you're seeing all around you and then you imagine that if you don't do that for your kids, you're somehow letting them down.
19:07So I think it's a really, it's just an important conversation to have. Like, what are you optimizing for? And listen, it's nuanced, right? Parents have become interested in being friends with their children versus being friendly. And that's a nuance. And like, and then every parent comes up with an excuse. We talk like this for five minutes and there's a parent on the treadmill, walking their dog, driving. And they're coming up actively right now with the excuse of why their kid's situation is different. But you don't get it. My son is X or you don't get it. My daughter went through Y. And all of that is like so understandable because I do this, like, you know, it's so easy to talk about it in the abstract.
19:42I'm sitting here on a podcast. So I can talk about it in the macro. When it gets to those little fuckers that you love more than breathing. You're like, it's so hard, but it is the answer. It is the answer. It is the answer. Listen, I couldn't agree with you anymore. What do you see when you look around at your peers, at the people you know have been successful, all the ambitious people in front of you, what has been running underneath their ambition? What is it that those people all have in common? I think a weird one no one talks about is curiosity. I think a lot of my most successful friends I associate with on my artistic side They're just really artists.
20:19They're curious. They're like, what if I did this? Like, there's a really romantic part of it. Yeah. Some of it's silly, like early youth, just like they want stuff. They just want status. That was maybe a bit of me. Yeah, I mean, that's just like normal. It was that simple. Yeah, it's not super complicated. Like they put a specific person on a pedestal and they want to emulate. That'll work too, to a degree. Yeah, I mean. It works to get you so far. Some people come from beautiful places, like wanting to get their mom out. And then I think there's a group of us that are similar to what I said about myself as well, which is like, you don't even know.
20:54You're just seeing the light and you just can't. It's like, you're fucking like, I don't know. Like, I can't help it. Like, this is just what I want to do. I want to create. I'll actually give you a story on this. I was once in Turks and Caicos. I watched this kid once build the craziest sandcastle situation I've ever seen in my life. Worked on it for seven hours. This eight-year-old was a fucking dog. He just built it, built it, built it. I was like just listening to music, watching him for like eight hours. Out of nowhere, like the, you know, out of everywhere, like the day comes to an end and his parents call him to go clean up because they're going to go to dinner at the resort.
21:33I don't remember his name. Johnny, we're going. This kid stands up, takes a good look, no phone, no anything, no bringing anyone over, takes a good look at this masterpiece. and then bashes it to the ground and leaves. Yes, he does. And I swear to God, I looked at that kid and I'm like, that's me. Wow. That's me. I am not doing any of this Gary. You would be flabbergasted how detached I am from the Gary Vee brand, from my professional career, from all of it. Like if I was a musician, I would live in the studio. Yes, I would tour and all that stuff because I'd have to do it for the game. but I'm just in my lab.
22:16This kid was just in his bag on this sandcastle. He didn't need someone to see it. He didn't need everyone to be like, oh my God. He didn't need to take a photo to show everybody. He just built it and that was enough and he tore the whole thing down. I feel like you wear the, I don't care. Like it's a badge of honor. Why is that so important? It's actually different, Emma. It doesn't come from a place of like audacity or I'm right. It comes from a place of simplicity. I care deeply. I just care about myself. I care about me. But in that selfishness, it allows me to be incredibly selfless. It allows me to do such incredible things for my family and the people around me and the people I'm close to and my nonprofits and blah, blah, blah.
23:01But like, I don't, yeah, it's not like I'm cool guy and like, fuck you, two fingers up. And like, I don't give a fuck what you all think. It's really from a much more loving place. It's just, I'm quiet in my little place. I'm out there a lot because I have great joy of the deposits I'm leaving in the world. I feel a sense of responsibility even. You do? Yeah, I do. Because I think a lot of people are putting out dog shit. I think there's a lot of confusion out there. I feel that the worst sentence on earth is nice guys finish last. I think it has been detrimental to society. And I take on the responsibility and the judgment of telling the truth, which is nice guys finish first.
23:42It's very important for you to be nice, right? It is the only thing I care about. Yeah, nothing drives me more crazy when pretty girls are on social media telling all these boys that they want to hook up with that if you're nice, it gives them the ick. It makes it, the whole thing's fucked. It's also not true. Yeah, no, listen, I married a nice guy. I can't even imagine, I can't imagine anything else. And I actually really, when I think about attributes in business, it really befits you to be nice. It's really good for you to be nice. Especially if you're playing long. Well, of course. I mean, what are we trying to be like, you know?
24:17I'm playing long. Yes, you have to. You know, and so if you're a marathon runner, not a sprinter, if you're trying to make a quick bag and get a private plane and go smoke weed on an island and do all this frivolous shit. Yeah, you can be an ass up. Go fast. Yeah. Fuck it. Nice. Knock yourself out. It's not what I'm trying to do. So what do you think the most important attributes are? Because when you, we were talking about like skill, like when you think about curiosity, but what is important? Resilience, tenacity, curiosity, patience, self-awareness is number one. If you don't know yourself, you're finished.
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24:53How do people get to know themselves though? Because I really think those of us that have like a natural inclination to learn more about ourselves, to understand our habits, our patterns, what makes us us. How do you cultivate self-awareness? Because it is one of the most important things. Putting the people around you in a position to tell you the truth without ramification. Yeah, which is harder the more successful you get. Or not. Well, it depends on the type of person you are. I think people are less likely to tell you the truth when you are successful. I had a particular moment this morning where I had an opportunity to tell someone who had been an arsehole that she had been an arsehole in a nice private way, not loud, but it was like, it was important to me to say, you know, she was very confused by something she'd done.
25:39And I was like, no, you were an arsehole. Clearly you care about that person. And that is the only reason, because if I didn't care, I wouldn't care to say anything. I'd be like, go on with your arsehole self. But it is really important. And people find it really hard to do that. Let me say something that I hope helps somebody. Most people have shut down their intuition a long time ago. What that means is most people then also realize that you can trick people by not saying it, by keeping it private, by the reverse, by being a hypocrite and by pointing fingers first. There's a lot of ways to trick.
26:13I would tell the people that are listening, the people you're tricking are not the people that you should be focusing on. while you're tricking the masses, the top 5 % of emotional intelligence and most emotionally intelligent people, you're exposing yourself to them. You're losing with the winning audience, excuse me, and you're winning with the losing audience. And so I would say this, humility is the great superpower of the truly unstoppable. I love losing. I love saying I'm sorry. I love being wrong. And I think that's a common trait for people that are really doing it. Yeah. Like really doing, not optically doing it.
26:57And I would challenge everyone, you're not succeeding by disguising it. You'll only succeed by leaning into it. So I would say self-awareness is garnered with humility, with making the people around you that work for you feel safe. It's crazy what my employees say to me. Well, that's what I want to understand. I think having people around you that will tell the truth is superpower. So how do you cultivate the type of conditions that allow people to tell you the truth? By when someone here says something to you, when someone - Rewarding it, right? Rewarding it. Facts. You're like, thank you for that shit.
27:34Not only thank you in private, like when a police says something - Yeah, in front of everyone. Oh my God. I mean, when Steve Unwin years ago said to me, Gary, you always talk about intent. if you have good intent, even if you make mistakes. Yes. But he said something interesting. He said, well, what if you don't act on me with that intent? And it made me think. I mean, you would have thought Steve won a Nobel Peace Prize. I was telling that story in the office for a month. So I think for you, especially, you know, and you're in this spot right now that a lot of people go through when it's like starting to really happen.
28:04No. That's when you have to almost triple down on facts, triple down on it. And then once one person gets rewarded for it, then everyone else starts to feel safe. But it's funny. I've hired, we're growing very quickly in all my companies. So there's a lot of new blood. And it's really funny watching a new player, especially an experienced executive who's worked in all these other places. Who has censored themselves. Yeah, and sees like a kid's shit on me. And they're like, what are you doing? Now, for everyone who's listening, don't be this person though. One of the big mistakes a lot of kids make in my company, they'll come in and they know this about me and they'll make something.
28:41they want to show that they'll push back, but they're pushing back on some dumb shit. Like you have to make sure the business you're standing on when you're pushing back against the lead player. There's real stuff there. Yeah, you better not. For sure, don't come with some bullshit and put me down. And I will kill you. No, I'm going to murder you. And I'm quick to be like, that was cute. You're trying to show that you're not a yes person. Please explain one more time what the fuck you just said. But I love what you're saying because I think that we have created conditions oftentimes around ourselves where we don't enable people to tell the truth.
29:12And it is something that really hampers people. I actually think again, and I always go back to women because there is an ease in the way that we kind of feel like we have to always give, you know, positive feedback, lift each other up. It's like, you know what? Like it's actually more helpful because women have fewer opportunities, fewer chances to get things right. They're held to insane standards. It's harder for them to raise money. When you lie to women, that's really problematic. Of course. We actually need more truth. You become an enabler of something that isn't right. Yes. And that doesn't mean you're not a girl's girl.
29:46No, it doesn't mean you're not a girl's girl. Quite the opposite. But let there be no confusion. I struggled with candor for a long time in my career because I watched people use candor to be a straight dick face. Facts. Right? People disguise candor to just be horrible. Yes. So we stood up something years ago in my company called Kind Candor. If you give a little sugar to the medicine you're about to give to, a lot of times it lands. Yes. And so like when you told that person, if you're able to be like, hey, listen, before I say anything, I hope you actually understand that I'm deeply coming from love because I think you're a badass bitch.
30:22But in this moment, like every human, I think there was a little, you know, it's how you deliver it. It's all about how you deliver it. Melody Hobson came on this podcast and she spoke about getting really hard feedback in her early career. and she said, I can't remember the, I wish I remembered who she was speaking about, but somebody very incredible. And she said, come on, give it to me, you know, be brutally honest. And he said to her, you know what? I'm going to be honest, but I don't need to be brutal. And I think that that is so important. You can give it to people straight without being a dick.
30:51You can give it to them compassionately, sympathetically, kindly. There's no reason to make it a to-do, but yes, giving real feedback, which was something I do amazing to the ether. but I struggled mightily in my 20s and 30s operating because I cared about the people and I thought it was scaring them if I gave them feedback. Yeah. And I misunderstood for a long time. For a long time. For 20 years. I'm glad to talk to you about that because I think it's such an overlooked point, like just to be truthful and to be honest and how that follows you. Because when you don't have much, you always have your reputation.
31:29Your reputation will follow you around. And there's so much of that that you're in control of. just telling the truth, being honest, being reliable. It comes back to you in ways that you don't even understand. I also think a lot about pendulum swings. Like right now with the explosion of digital, I'm getting very excited about analog. I'm glad you went there because that's what I want to talk to you about. Good. I believe that society pendulum swings every five, 10, 15, 20 years, whatever it may be. Baggy jeans, tight jeans, baggy jeans, right? You know? I know. I know about the jeans. I know you do.
31:58I think we've gone through an era the last 10 years, last seven, where just like morals and ethics and proper just completely went out the window. I think one of the great things of never compromising on your reputation, like trying to be a good person, I actually think we're in the pre-dawn of a very good era for good people. I think we're getting tired. I'm like, can that era just come along? I smell it. I do this for a living. I smell it. I'm starting to see the earliest cracks. What is giving you that feeling? Because I feel like a lot of people will be like, please, good Lord, let that be the truth.
32:35Fatigue of trends. You literally just think it's like being an asshole has just gone full circle. Yeah. Winning while being an asshole has gone full circle. We just kind of went to a place where like civility didn't become cool anymore. And we thought it was cool that everyone was fucking keeping it real and shooting it straight and blah, blah, blah, which then led to the next version, which is saying things that are inappropriate. I actually think it's a trend. I think it's fatigue. Remember, I'd like to think everyone, listen, I was a very bad student, but I was good at history. I'd like to remind everyone the 60s were pretty tumultuous.
33:11Fuck yeah, of course they were. Stay on this thought though for me, Gary, because you are such a thoughtful person. And when you make a prediction like that, it's not coming from nowhere. We are clearly in a moment where decency is completely unraveled. And it doesn't matter if you look politically, economically, through a lens of social, like the very fabric on how, Even day to day. I think we were raised. Even day to day. I travel a lot. When I watch a 80-year-old woman get to the airport gate and I see 19, 20-year-olds just sitting there. Oh, you've got to be fucking kidding me. And I'm like, someone.
33:44Help her. Please, God. Somebody help her. Even down to that level. Yeah. I'm telling you, and I'm glad I have this on wax. I know because I watch what everyone says. I'm telling you, it's starting. The earliest bubbles. I think you will see a lot of people gain popularity over the next two to four years by being civil.
34:16So if you're a graduate now, you're about to graduate and you're thinking about the future, you're thinking about what's happening in AI, what's happening, what's your job, what do you say to young people now to focus on? to reverse engineer what they think they're good at and what they like. When you're 20 or 22, you need to go into the biggest high-risk years of your life. 22 to 30 is high-risk time. But we taught them all to now you've grown, you got to get a job. We completely fucked it up. It's backwards. Yeah. 22 to 30 is insanity. No, it's fuck-around time. It's in a real way. And I don't mean like the way that people think about it, which is like, oh, it's fuck-around time?
34:55I'm not going to do shit. No, don't never do shit. It's what the fuck is your dream? But don't be delusional. Do not mix up passion and delusion. They're two different words. What do you love the most? Because that's going to get you to work as hard as it's going to require to break into something. And then are you actually good at it? That's the kicker. Yeah. Are you good at it? Are you good at it? Are you good at it? And then I'll say another thing. Get as close to the sun as possible. I know for a fact, a ton of young girls desperately want to be you right now. This is happening right now. If she's listening right now, she needs to spam the fuck out of this organization and get in here.
35:37And if she's just back there, literally serving, get as close to the sun. I could not push this more. I feel like you have to get in that room and do whatever the fuck you need to do to just be around it because osmosis is the greatest teacher in the world. You literally are like, boy, me. Is he not? Like, do you know why they're all laughing? Why? Because I say the same shit every day. Like you talk about osmosis. I speak about proximity and visibility. Just like, just go for me. Do, go, Gary. Like, just go. Life is not school. You are not going to learn how to be an entrepreneur by reading an entrepreneur book.
36:17You need to learn by seeing it. it's the jungle out here. Lions become better lions by hanging out with lions. Facts. You know, like the amount of people that leave great organizations where they have proximity to winners for$5 ,000 more somewhere. I mean, I see this all the time. I've been talking about this for a long time. So I get some really fun emails for people that really regret leaving. Oh my God, I was at this company. I felt undervalued for$2 ,000. They went to this other place. Like the learning experience when you're up close to someone doing it, it's called real life. It's how life works.
36:54But can I tell you, I, this is one of the things I like to talk about so much because I really get a lot of shit around this work-life balance thing, like being in the office and proximity. And I don't say it because I believe that people need to like ruin their lives and have no balance. I believe that proximity and visibility, right? The other way around, coming back at you, like you being seen, you being in the right space, you being in the right conversations, people being able to contextualize. Oh, look over there. That's KK. Like he's really good at this thing, this thing, this thing. And look at how KK took that feedback from her.
37:31Wow, he's so gracious. And then put it in his work tomorrow. Look at that great, but he's more senior. Oh, wait a minute. Huh, you can be talented and you can be gracious when someone on paper below you said something. oh, I want to be like that. It's much more detailed than just the black and white. It's the gray. It's the gray. And it's so interesting because I sat in a job that I felt extremely undervalued in, in my early twenties, but I learned so much. My desk was in front of the boss, the owner of the company. And I used to listen to this woman every day. I heard every shit thing that was happening in that company, every conversation I heard how she won business and I was just soaking it all up.
38:11We've lost the art of no one gives a fuck. When you're 24 and you're sitting and you feel undervalued, the power of knowing no one gave a fuck about you was actually a strength. It was. Now, it shouldn't be inappropriate. Back to what you were saying about work-life balance. You're not talking about like burning out and dying. No. But entitlement is a disease. And if you're walking into an organization that you haven't done shit in and you're a child and you think you should be the fucking VP and your thoughts should be like overvalued, that's called audacity and it is not attractive. No. And by the way, if you're such a whiz kid, go do it.
38:49Go do your thing. Like, yeah, yeah, yeah, take your shot. Because by the way, there's unlimited 23-year-olds cooking. Yeah. With social media. There's unlimited 23-year-olds. People say all the time, like, Gary, you don't get it. I'm like, I do get it. There's unlimited 23-year-olds cooking. Do we not know that? This is the greatest era ever for 20-year-olds. You've unlimited opportunity, live shopping, social media, content, vibe coding. If you're 25 and you're not cooking, you suck. But are you ready for that message? You're definitely not when your mom and dad said you're the best and fought all your fights.
39:26And when I say you suck, that's not bad. Because the cool part is you have unlimited time to dominate. Yeah, you do. Unlimited. Yeah, you do. But when you actually internalize what I'm saying and you're like, wait a minute, I saw a TikTok that said, this is the worst generation because the boomers took all the money. Did you not notice the 93 ,000 people you're following that are making a million dollars a year in brand deals that are your age? Which part are you listening to? Which part are you listening to? Whatever you choose to listen to, right? Whatever you choose to put your focus. Emma, life is very simple.
39:58You find what you're looking for. You think the world sucks? Good news. It does. You can find it all day long. Yeah. but you want to think the world's awesome, good news, there's unlimited things to see. You choose. I want you to get back to something that I look at you and think that you have been so brilliant in predicting what is to come. And I love that you talk about the return of civility because that is something that I think is so needed in the world right now. It's coming. And I love that because I think I've always been the Michelle Obama and gone high. So that feels good for me. But talk to me about, because I've seen you speaking so much about the next trends and you predicted YouTube.
40:36You predicted, you know, so many of these like big social movements, how important social commerce was going to be. And now you are nonstop talking about shopping. I'm like, you are obsessed. And I'm like, listen, how have you even become someone that can spot that and see it? And then you can talk to me about what's going to happen. I work. Like how many people listening to this podcast did unlimited research 12 years ago when China was doing the same thing. I have a funny feeling, not many. Not that many. You know, 20 years ago, like why are guys bringing back these weird mustaches? You know, four years ago, back to the jeans, like, whoa, skinny's out.
41:15Like here comes, you know, like why? But when you talk about curiosity as a superpower, you're talking about a deep, like you're going in and in and in, asking questions, taking meetings, because you don't come to those type of assumptions without deep understanding and knowledge. That's right. And then you're applying them and making money from them. And then by the, yes. And then by the way, I'm not predicting, I'm commentating. Let me explain. Please. This year, TikTok shop will probably do between 25 and$40 billion in GMV. That means gross merchandise value. That means everyone in the studio and everyone listening at home, $25 billion worth of stuff is going to sell on TikTok talk shop this year.
41:58I'm not predicting shit. It happened. Y 'all just don't know about it at the level that you think. And I've seen this movie over and over, e-commerce in the 90s. I was right about putting my daddy's liquor store on e-commerce and yapping about e-commerce, not to the world back then, to my circles. But eBay and Amazon had already happened. I was right about social media. Top eight had already happened on MySpace. I knew it was just going to keep building Live shopping happened in Asia a decade ago. Yeah. And it's been happening on whatnot. But it's been slow to take off here, right? Because again, I have brands that are huge on TikTok shops.
42:37And yet live shopping is something that we haven't quite cracked yet. It's early and it's a different skill. It's being good at QVC, not being good at catalogs on the internet. Yeah. That's different. It's a different thing. It's a different thing. Everybody's trying to have a hit podcast. It takes talent. It takes a team. It takes work ethic. It takes serendipity. It takes a lot of shit. Like everything good is hard. Live shopping is good, good. What do you think the next evolution is then? When you look at what's happening in US commerce, is it just that you're looking at China and you're like, okay, whatever's happened there is going to pop off here?
43:10No, because you have to know what Americans do. You need to know what, and then it goes deeper. Then it becomes, what do moms do? What do teenage girls do? Then it's, you break it again. What do black teenage girls do? White teenage girls do? Hispanic, and then you go into interest. What do cool girls, like people, You go, you know, it's very - And on and on and on. And on and on and on. And then you have separation of wealth as a macro financial trend. You start thinking about things I think about, which is like the air wanification of every category. What does that mean? That means$150 suntan lotion.
43:40Yeah. That means$65 band-aids. That means$130 pack of bubblegum. Because you might not be able to afford a private plane and you might not be able to afford a big mansion or a$200 ,000 card. But you might be able to get to a$130 pack of gum and everybody wants that feeling, unfortunately. They're going to use materials to close emotional gaps. So you don't see that changing? It's probably almost my life's work of hoping that can change, but no. We've got deep-rooted human truths that ebb and flow through society, through moments in time and history, I wish they did. So I think about a lot of trends, but live shopping, I think for this audience, this is a big one.
44:32There are many men and women listening right now who dream to be content creators and influencers who are destined to never be, but would actually make hundreds of thousands or million dollars a year being live shopping hosts on TikTok. So let's talk about that for a minute. So there are so many people that listen to this podcast that think, you know, I've got something special. I need to be making more money. How do you, Gary Vee, sit there and say, all right, you know what? I'm going to try something. I heard, I listened to Gary and he said that, you know, this whole online shopping thing is going to take off.
45:08Like, what are the next steps? They literally take out their phone right now and they go to Claude or ChatGPT or Gemini because we live in an AI world. And they literally say, I just listened to Gary Vee on Aspire with Emma talk about live shopping. I'm a 42-year-old stay-at-home mom that likes plants, Bravo television, clean eating, and fashion. I heard something he said, something about what not or something. He also said TikTok shop. How do I set up a TikTok shop account? Give me four examples of people that have gone from zero to meaningfully strong that look like me. Enter. Emma, how do people get into better health?
45:52how do they get into better? How do people get into better physical health? By fucking doing it. Correct. They eat less, they exercise more, they get all the information and they find somebody that they think is like hot and healthy and copy whatever the fuck they're doing. Business, life, everything. It's actually shockingly simple on paper. It's incredibly hard to be disciplined. So let's go back to where we started at the top because what is stopping that 42 year old mother who's sitting at home is fear. She knows that when she goes on TikTok and she's selling a plant in her living room that the other moms in the neighborhood can see it.
46:27And that's that. And she doesn't want to hear like, why are you doing that? Do you and your husband, are you guys having financial trouble? Right? Facts. Facts. Oh, are you, oh, Emma, are you going through a midlife crisis? Like that was so weird what you did. Like you're selling plants on TikTok. I feel so, are you okay? Are you okay? They're scared of the pity of the hurt. I would never do that to the Emma. I would be the friend to be like, girl, I'm proud of you. Let's go. But they fear the pity of the hurt. The only reason her neighbor said that to her, she's not happy with her marriage right now.
47:04Or she's worried about her daughter right now. Or her mom was just diagnosed with cancer and she's scared. People are not living their full life because they fear the pity of the hurt. And if they've really listened to this podcast, and they go back to the top and they listen to what it is that you have in the sense of you just don't give a fuck. And when you hear that critique, you have radical empathy that goes back to why is that person so judgmental about me selling a fucking plant? You would be able to just wash straight over it. If I was that 42-year-old woman and I went outside to get my mail and my neighbor who's my girlfriend came up to me and I'm that 42-year-old woman And she said, I'll call myself Garena.
47:52Garena, are you okay? That was a little weird. I saw what you did on TikTok last night, selling the place. Is everything okay? Is your husband okay financially? Like what's going on? I would literally say to Sally, I'd be like, Sally, I feel so like, are you okay? Why would you say that to me? I'm trying something new. I want to do something. Why are you trying to tear me down? That can only mean that you're not in a great place. Are you guys okay? Yeah. I'd be like, Sally, do me a fucking favor. Get the fuck out of my face. Buy a fucking plant. Support a neighbor. Sally, shut up and buy the fucking clothes.
48:23Tell your mate. Be a girl's girl. Literally. You remember Avon when those ladies would come around to your house? My mom would be like, buy a lipstick. Like, do what you can. But Emma, real quick, I want to go deeper on this because I'm going to change at least one person's life, one of your listeners. TikTok affiliate. You don't need to own the product. You literally go to the affiliate store. You're like, oh, I like that makeup. You apply. if they decide to work with you, they send you a sample. You literally make a video of it. You're off to the races. And if God forbid, for some ungodly reason, that video gets 14 ,000 views and you make$83, I'm watching person after person after person.
48:59This is an e-commerce that you and I did not grow up with. They don't have inventory. And by the way, we are doing that with all of our brands. Of course you are. And it is working unbelievably well. It's crushing. That's affiliate. And then there's the live shopping for the people that have the gift of Gap. And that's crushing if you're talented. Not everyone's fucking Oprah. Sadly. Yeah, agreed. So Gary, before we stop this part, tell me what are the signs and the signals that people should actually be paying attention to when it comes to like the changing of consumer behavior? Like you have obviously honed this over a long time, but what is it that people should actually be paying attention to?
49:35First, do not be a person that romanticizes yesterday over tomorrow. The reason most people don't see what I see is because they don't want it to happen. People hate change, Emma. I do hate change. People are not adaptable. I prefer it. I'm at the top of my craft, Emma. Emma, do you think I want another social? Do you think I got excited three years ago when I'm like, fuck? And sub stacks and beehives. You're like, what? I was killing it on these other platforms. I wish we just still had email. I was the king of email in 97. Seven, I don't get excited when a new thing comes along, but I have a responsibility to be a winner.
50:16And so I adjust to whatever's happening next. And so I think first it starts with that. Next, it's watch people. Emma, almost everyone judges people without watching them. Everything's stigma until it's not. Five minutes ago, if you met someone on online dating, you were like a weird dude in the basement. Now it is the primary source of how people go into relationships. You know, for the woman that's thinking about selling on TikTok shop, your girlfriends are going to make fun of you and they're going to ask you how to do it. That's what's going to happen. So I think it's a couple of things. One, don't be romantic.
50:53Don't demonize the new stuff. Don't put your head in the sand about AI. Always go with maybe instead of no, and then put in the work. Always ask why. Why is everyone going to that restaurant? Why? Why is everyone loving that influencer? Why is that new TV show crushing? Why is that the it girl? Seven years ago, I'm like, oh, here's why these girls like Emma Chamberlain. I just read all the comments. Yeah. You just read it. Exactly. It's the comments. Yeah. If you don't understand. Yeah. And so that's it.
51:33if you were starting from zero today you have no audience you have no nothing no money no audience no reputation no resources what would you do i'd make content on the internet either about things i know if i still had my knowledge yeah i would talk about business i'd be johnny pants magoo and I would talk about business and wine and sports. The greatest equalizer that the world has ever seen is social media. Literally, there's no gatekeeper. Oh, the man is keeping me down. The algorithm doesn't give a fuck. No, it doesn't. The algorithm doesn't give a fuck. And you can only really appreciate that and understand it and all contextualize it because when you came up in the fashion industry, the keys to the kingdom were held by three people, right?
52:14It was like there were a finite amount of hair people and makeup artists and stylists. And that was it. And unless you were in with those people, there was fucking nothing. Gatekeepers. Now it's completely democratized. Completely. Completely. At a scale that is insane. So what do you think that this generation have got going for them that like no other generation has had? Opportunity. Yeah. Again, this is what blows me away. One stupid piece of content that tells you that the boomers took all the opportunity away from the kids makes kids believe the complete opposite of what they see every day, which is unlimited people that look like them winning.
52:48When I was coming up the game, you had to eat shit for 15 years to begin the first phase of opportunity. You should eat a little bit of shit though, no? I'm a big fan of it. I mean, I think so. I love eating. It's how far. I think I'm saying it right now. I believe that adversity and humility are foundational to joy. Foundational to joy. I think that you're absolutely right because what you're talking about is a breeding ground to do the opposite of all the things that we know as foundational to be successful. And there's another thing. kids learn pretty early when their parents are full of shit.
53:20Like it's 8, 10, 12, 13, 15, depending on the kid. When you're telling your 13 year old, you can do anything. And the kid's like, no, I can't. You're starting to lose credibility. Yeah. Stop bullshitting your children. This is why you credit your mom with so much. This entire podcast was brought to you by Tamara Vaynerchuk. I am literally the byproduct. I am the meal that you're like, oh, that's a beautiful meal. She is the woman that picked, gave me the ingredients and then cooked the meal. I am, I literally don't exist, Emma. I am my mother's by-product. I love that. It's true. I hope my son speaks about me like that when he's older.
53:58I do not exist. I'm like, damn right you don't. What is she like? Is she so proud of you, your mom? Yes, but she was proud of me long before, right? Again, I think this is a big thing. I hope this helps parents. I've come to believe that it is really scary how much you become what your parents cheer about. For example, if you're born fortunate and you have pretty privilege and your parents are constantly, your entire youth, talking about how beautiful you are or handsome you are and like your identity becomes that and you're going to be that kind of person that in your 50s and 60s is still glam.
54:31If this is the one I'm very fearful of, if your parents make everything about grades, quietly they're telling you conform to a system that judges you. That's why we have so many employees. And if your mother cheers only about you being a nice boy and opening up doors for women and being kind and being nice to your sister, you end up being a nice boy. That's just the truth. End of. End of. It really is that simple. It's really that simple. Now it's nuanced and there's other things. But like the thing they cheer becomes who you become. And so I think parents have to be very careful and thoughtful about what they're spending on positive affirmation because a young human will continue to gravitate that for a long time.
55:15Gary, if you could change one thing that the next generation believes to be true, specifically about success, what would it be? It is actually my north start that nice guys finish first, not last. And obviously that goes for girls. And that is that, that this concept that you would need to have sharp elbows, that you need to step on people, that it's a dog-eat-dog world, that it's a jungle. These are all true-ish, but the world is abundant. And your reputation is your biggest asset. And everybody gets exposed quietly. This is the thing a lot of winners don't know. There's some people right now that are winning that are not good people that are driving and they're like, wrong, right now.
55:59And they're Beamer, wrong. What they don't know is how much they left on the table because nothing ever came to them because all of us other winners were like, fuck you. They think they won with 6 million. Do you know what's better than 6 million? 60 million. They don't know that they left 54 million on the table. Got it? That is the truth. Yep. That is the truth. Yes. Or I'll be happy if your next prediction comes true. The civility? Yes. That might be for me the single best takeaway that I have heard for a really long time because we are in deep need. It's coming. We're tired. That's why the 60s looked differently in the 70s with disco.
56:40And by the 80s, we were tired. You can't, my friends, you all know this. We can't stay in this sustained anxious state in perpetuity. No, we cannot. We will crack. And what we will do as humans is we'll adapt the other way and we'll start gravitating to simplicity and kindness. It's coming. If you believe that to be true, how do you cultivate that? Because I think what is dragging people down right now and what causes people to act other than civil is that they're bombarded by so much shit and so much drags them down. So how do you actually cultivate that in your life? For the audience, it's be the person you wish everyone was.
57:22Shit is so simple. Be better. Be nicer. When you are hurt, recognize you're insecure. And that's why you're triggered when someone cuts you in line at Starbucks and you lose your fucking mind. That is the great tell that shit's fucked up for you. Be empathetic. Maybe shit's fucked up for them. Everyone thinks the whole world revolves around them. It does not. It sure doesn't. And then for me personally, like the proudest thing professionally that may end up happening to me is that when people look back at this era, Because all the receipts are online. During the hardest 10 years when everyone was shitting on everyone, I shit on no one.
58:01You didn't? Nope. That was choiceful. It's just not who you are. Do you ever feel like shitting on someone? Like Tom Brady and Michael Jordan because I love sports. They hurt my feelings. They fucked you over. They killed you. In sports, I do it a lot. Yeah, yeah. That's different. Correct. It's a fake world. That's not mean. That's right. That's not mean. No, I don't have the audacity to think everyone should see the world. That's the funniest thing, Emma. this concept that everyone should see the world the way you see it. Do you know how insane it is to spend time to go watch someone's video and leave a nasty comment?
58:34You know how fucked up that like - No, that's psychotic. It's actually fully psychotic. You know that. It's like, on what planet was that a good use of three minutes? Yes, but who was your mother? If you don't have anything nice to say, don't fucking say nothing. I'm so pumped that you're excited about this. Oh, no, no, no. You are going to be - Best thing I've ever heard. I can't wait to see - Best thing I've ever heard. I'm like now so hyped to see you in seven years. I'm going to see you somewhere in seven years. Are we going to see me? And you're going to be like, how the fuck? Because we as humans - I'm praying for it.
58:59I'm praying for it. Let me tell you exactly why it's going to happen. We get tired. We're over the energy staff. And by the way, everyone who's listening, who's like, you're delusional, Gary. No, no, I understand most aren't. I'm telling you that I see the cracks that some are at enough scale that I think it's going to pendulum up. I'll be on the other end of that pendulum swing. I'll take it. I want to believe that. And you have the ability to impact. Yes, I would think so. It's like, who do you want to be? You know, Michelle Obama says this beautiful thing. She always says, you know, you're in training for the type of person that you want to be.
59:32And I think that you choose your choice. You choose how you react to the world every single day. I just think it's crazy to go roll in the mud with the other pigs. Totally. I mean, listen, I'm going to start with yourself, girl. It all starts here. You can choose. You're in control. I'm moving you to rapid fire. Let's do it. All right. I'm the worst at rapid fire, by the way. I don't even know how to do it. I'm remarkable at it. Are you? We'll be solid at this. We'll be average that. If you're the worst, then I'm remarkable. What's one habit that's had the biggest impact on your career? Accountability.
1:00:02I think everything is my fault. It is the foundation of my success. And I like it. You are good at rapid fire. What is a business opportunity that you passed on that you regret? Did you have a lot of them? Sure, I missed the email from airbedandbreakfast.com. Begged me to invest. That was bad. I passed on Uber twice. Aye, aye, aye. If I wrote my normal$50 ,000 check, I would have had 500 million. That was bad. That was bad. I mean, I could take up four hours. You're done. You're good. You had me at 500 million. What's the most important thing that you've changed your mind about? That candor is good.
1:00:43I used to think it was bad. I thought it was fear. And now I've realized not giving candor actually creates real fear because then people don't know where they stand with you. I hope people really listen to that one. Is there a book that changed your life? My reading comprehension is non-existent. And yet you're like - I got a text today on the way here five seconds ago. Literally, an hour ago, I got a text coming here. I think she wrote this employee of mine four lines, four sentences. Couldn't get through it. I replied, set up a 15 minute meeting. I have no reading comprehension. I've read less than 10 books.
1:01:16So as a dyslexic person who can completely understand that, and you write a lot, you put out a lot of content, how do you take in information? Because it's very, very clear that you absorb an enormous amount of information. You're undeniably curious to a fault. So what is it like, how do you get your information? Because mine comes at me mostly through books. So where does it come from for you? If I hear something or see something, it's a lock. If I read something, I have no chance. If I drive somewhere one time that's complicated, I will never, ever not be able to do it again. Really? If I see it or I hear it.
1:01:55So I'm constantly, yeah, so I'm killing it, you know? Yeah. But I have to hear it or see it. That's the only way that it goes in. Yeah. What is something that you still aspire to? You know, I still think I'm dramatically under-indexing professionally. I mean, I genuinely believe I'm going to build much bigger companies, much more impact. This VFriends thing is big for me. It's going to be my legacy. You think so? Yeah, I think I'm building a Disney Pokemon, but really a Sesame Street. I feel like I'm more Jim Henson than I realized. I really aspire to build one of the great intellectual properties that brings good.
1:02:34That's why I say Jim Henson, Fraggle Rock, The Muppets, Sesame Street. You're taking me back. Can you imagine? So I've got a lot of professional goals, personal, very little. Like I feel very good where I am with my humanity, but on the field as a player, I've accomplished a lot professionally, but I feel like I've got a whole, whole, like uncomfortably a lot more to give. Wow. All right. We'll be watching this space. Thank you. Amazing. Thank you, Gary. Thanks. Such a pleasure.
1:03:07if you're loving this podcast be sure to click follow on your favorite listening platform while you're there give us a review and a five-star rating and share an episode you loved with a friend we'll be so grateful aspire with emma greed is presented by audycy i'm your host emma greed executive producer ashley mcshan derrick brown and me our executive producers from Odyssey, Leah Reese Dennis, Asha Saluja, Lauren Lagrasso, producer KK Sublime, Stephen Key is our senior producer, sound design and engineering by Bill Shultz, Angela Peluso is our booker, original music by Charles Black, video production by Evan Cox, Kurt Courtney, Andrew Steele, and Carlos Delgado, social media by Olivia Homan, Catherine Bale.
1:03:52Special thanks to Brittany Smith, Sydney Ford, my teams at The Lead Company and WME. Maura Curran, Josephina Francis, Hilary Schuff, Eric Donnelly, Kate Hutchinson-Rose, Tim Meikle, Sean Cherry, and Lauren Vieira. If you have questions for me, you could DM me at Aspire with Emma Greed. Greed is spelled G-R-E-D-E, that's Aspire, A-S-P-I-R-E, with Emma Greed. Or you can submit a question to me on my website, emmagreed.me.
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1:05:02Then around age four, kids transition to the smaller Lego bricks, and suddenly you're watching real structures take shape, real ideas form, and their imagination really take off. They begin with simple stacking, but over time they grow into full-on creators, building worlds, stories, and things you never would have expected. That's the kind of magic of Lego bricks. You're not buying a phase. You're starting a journey. Learn more and start building today with Lego bricks.
From the publisher
Gary Vaynerchuk has spent the last two decades understanding where culture and consumer behavior were headed long before the rest of the world caught up. He was early to YouTube, Twitter, TikTok, creator commerce, and live shopping. But this conversation is about more than algorithms and internet trends.
In this episode, Gary sits down with Emma to talk about the real reason most people stay stuck: fear. Fear of judgment. Fear of failure. Fear of what other people will think if they try something new.
Together, they unpack the insecurity driving modern ambition, why so many successful people are still deeply unhappy, and why Gary believes we are entering a cultural shift where kindness, reputation, and emotional intelligence will matter more than ever.
Gary shares:
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Why most people are living for opinions they don’t even respect
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The hidden insecurity driving high achievement
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Why reputation compounds faster than money
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What social media actually revealed about human behavior
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How parents unintentionally destroy confidence in their kids
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Why proximity and visibility still matter in the AI era
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The business opportunities Gary believes people are still underestimating
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Why “nice guys finish first”
What would change in your life if you stopped making decisions based on other people’s expectations of you? Drop it in the comments — we’re reading. And subscribe to Aspire with Emma Grede so you don’t miss what’s next.
We'd love to hear what you think. Please take this survey to help us make the show better for you: emmagrede.com/survey
