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I am so excited to share my debut book with you all. Start With Yourself which is available now. You might have seen the headlines, you might have seen the social, but this book is exactly what I intended. A conversation that will make you think and it's a blueprint for anyone who wants success without the toxic positivity. Start With Yourself is about self leadership because wherever I go, women ask me how I got to where I am. But what you really want to know is is how you can get there. So I'm doing what I do best, sharing and never gatekeeping what's works for me in the hope that you can borrow from a philosophy that has served me so well. The truth is I'm not an expert. I've just lived it. I've made the mistakes, I've had the failures and I've learned what actually works. It takes a lot. It takes the most. And this book is for anyone who's tired of feeling like a passenger in their own life. It's about taking responsibility for your thinking, managing your emotions and getting clear on your ideas and then knowing your your next step. It's about picking yourself up after failure, being accountable, but also forgiving yourself, pushing for wins and never ever apologizing for your ambition. It's also about challenging the rules that you've been told There is no perfect time. Balance isn't the goal, alignment is, and there's nothing wrong with you wanting more. I'm precisely sure that the reason I've been so successful is so I can share it with you. Start with yourself. My debut book is available now. Visit emmagree.com to purchase the book. Also available on Amazon, your favorite audio platforms, and all good bookshops. So 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 gonna belong to people who are kind and have humility. Those who bought reputations worth defending. And he's not saying it because it sounds nice. He's saying it cause 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. Now 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. And listen for what he told me he'd do if he was starting from zero today. That's the part you'll want to write down when your day starts early and doesn't slow down. The things that tend to fall off are the things your body actually needs. The vitamins, the gut support, the basics that keep everything running. I felt that, especially this spring with the book tour. Eight cities, different time zones, never the same morning twice. It's the kind of stretch where it would be easy to let your routine slip, but AG1 is the habit I've stayed consistent with through all of it. It's a daily health drink with prebiotics, probiotics, superfoods and antioxidants all in one step. Just one scoop with 8 ounces of water every morning and you're done. Their next gen formula delivers 75 plus ingredients backed by four clinical trials. It's shown to feel the common nutrient gaps and support your gut health. What I like about it is the simplicity. So even on the road, I know I've taken care of the basics. This is the one thing that covers a lot of ground without adding complexity to my day. AG1 has over 50,000 verified five star reviews and comes with a 90 day money back guarantee. Visit drinkag1.com aspire to get a free AG1 flavor sampler and a bottle of vitamin D3K2 in your AG1 welcome kit when you first subscribe. A $72 value. That's drinkag1.com aspire drinkag1.com Aspire Insurance isn't
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A
Gary welcome to Aspire.
B
Thank you for having me.
A
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 the foundation for something which you and I clearly have in our life. But I kind of wanted 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.
B
You know, at its most basic, Fear. It's why so many people weaponize it. They 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. And you know, I'm very motivated by putting out content and talking about it because every day people get unlocked, whether 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 your question directly is insecurity.
A
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? Like, how have you in your own life, been able to do that?
B
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. Shut up.
A
Yes, it is.
B
You know what I mean?
A
If you experience fear, you must have it. So.
B
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 5. My father lost his dad at 15.
A
So it was a legitimate fear for me.
B
It was a legitimate fear. It was in the air.
A
Yeah.
B
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.
A
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 minor leagues, losing money. I'm just like, that's not real. Like, that's not actually something to be really scared about.
B
That's right.
A
But one of the things I've heard you talk about a lot is whether or not everyone should be an entrepreneur. I think 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
B
a relationship with people, 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. They'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 hundreds, oh, yeah, 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.
A
We all have regrets, and I think the biggest regret is just when you don't try something right. When 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?
B
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.
A
In what way?
B
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. I thought it was confidence. I thought, of course, you 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?
A
Yeah.
B
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 over 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.
A
So what was it that drove you then?
B
Wanted 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? 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.
A
So how do you actually figure out. Because I do think that there is a whole audience of people that are listening and I really believe that you can be entrepreneurial in a corporate environment in like a regular job. But how do you figure out if there's a. 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.
B
There's no weird test, there's no bullshit report.
A
Isn't that what's so hard for people to understand though? You just got to do it?
B
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.
A
I think it's really important to contextualize how important it is to eclipse fear and to have like moments of failure. Like 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?
B
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.
A
What, you mean in your own head?
B
Yes.
A
You've been able to tune everyone out.
B
Everyone, including my. Even the ultimate, my mother, who's everything to me.
A
How?
B
I'm not sure.
A
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?
B
My best guess at this moment in my life is some sort of almost probably not even proper over indexing on empathy.
A
Please explain that to me.
B
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.
A
And how quickly do you go there? Like, immediately as you're getting the shit, really.
B
And I got there.
A
Oh, that takes training.
B
And I got. Again, this is why I think about natural DNA a lot. Yeah.
A
Yeah, for sure.
B
You know how there's, like tennis players sometimes at 14, in the women's side, they can win Wimbledon at 14. 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 maybe it was the market giving me validation. By the time I was 10 and 11, I was really slinging that lemonade and that shovel and those baseball cards. 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 gonna do my thing, be a good person. See ya.
A
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 down. I think it's the punchline, right? Yes, like 100%, yes. I would say that I've become infinitely more successful the less that I have listened to other people.
B
But 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 funds. 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?
A
Like, totally.
B
That's where you try to go.
A
Or maybe, you know, you launch a book and you get a lot of criticism, something like that. Like, either.
B
Or, you 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 Brittany back, bitch.
A
Like, it's just what we do.
B
It's what we do. It's what Society does.
A
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, like, 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.
B
They'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.
A
And you believe that people just eating that up. It comes from a lack of responsibility.
B
Well, let's play it out.
A
Yeah.
B
You're unhappy. Your life sucks.
A
Yeah.
B
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?
A
I just wrote a book called Start with Yourself. And one of the things I talk about is my upbringing was exactly like that. I was surrounded by 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, though? And why are people being so swept up? Like, why is there such a lack of responsibility for ourselves?
B
Insecurity.
A
You think it all comes back down to insecurity?
B
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. And I believe modern parenting in the last 30 years has out of good intent. This is a very important part of the sentence. Out of very good intent created more insecurity than historically. And we're feeling the effects of that as well.
A
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.
B
I see it.
A
Yeah.
B
Because I'm on the receiving end. 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. And I analyze it.
A
How much of that do you say?
B
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 sentiments.
A
So you're actually looking at everything.
B
And I used to on a flight to LA like this, read, pour out. And by the way, I still like to do it because I'm a little old school.
A
Every now and then I'm like, yeah, yeah, yeah, yeah.
B
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. What world is that gonna 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.
A
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B
That their parents tricked them into thinking like that work ethic and like that real life isn't real. Their expectations got whacked.
A
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 and a time right now where we are actually a little bit unsure of what we're even growing our kids up to. Do you know, what is gonna 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?
B
Build confidence. And confidence can only come from what
A
they do, not what you do for them.
B
Got it.
A
It's that simple, right?
B
It's really that simple.
A
It's really that simple.
B
And it's really like. It's that simple and it's fucking hard.
A
Yeah, 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 kid, you're somehow letting them down. So I think it's a really. It's just an important conversation to have. Like, what are you optimizing for?
B
And listen, it's nuance, right? Parents have become interested in being friends with their children versus being friendly, and that's a nuance. 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. Cause I do this. It's so easy to talk about it in the abstract. I'm sitting here on a podcast, so I could talk about in the macro, when it gets to those little fuckers that you love more than real, it's so hard. But it is the answer.
A
It is the answer.
B
It is the answer.
A
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 has in common?
B
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. They're Curious. They're like, what if I did this? Like, there's a really romantic part of it.
A
Yeah.
B
Some bit silly. Like early youth. Just like, they want stuff. They just want status.
A
That was maybe a bit of me.
B
Yeah. I mean, that's just like normal.
A
It was that simple.
B
Yeah. It's not super complicated. Like, they put a specific person on a pedestal and they want to emulate.
A
That'll work too, to a degree. Yeah. I mean, it works to get you so far.
B
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. You'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 nowhere, out of everywhere. Like, the day comes to an end and his parents call him to go clean up. Cause they're gonna go to dinner at the resort. John, I 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. Garrett, 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. Cause I'd have to do it for the game. But I'm just in my lab. This 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.
A
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 an important.
B
It's actually different, Emma. It doesn't come from a place of, like, audacity or. 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. But, 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. Cause I have great joy of the deposits I'm leaving in the world. I feel a sense of responsibility even.
A
You do?
B
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.
A
It's very important for you to be nice. Right?
B
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 the whole thing's fucked. It's also not true.
A
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.
B
It's really good. If you're to be nice, you're fit for playing long.
A
Well, of course. I mean, what are we trying to be like?
B
I'm playing long.
A
Yes, you have to.
B
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. Go fast. Yeah, fuck it. Nice. Knock yourself out. It's not what I'm trying to do.
A
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?
B
Resilience. Tenacity, curiosity, patience, self awareness is number one. If you don't know yourself, you're finished.
A
How 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.
B
Putting the people around you in a position to tell you the truth without ramification.
A
Yeah. Which is harder, the more successful you get or not? Well, it depends on the type of person you are. Correct. 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 asshole that she had been an asshole in a nice, private way. Not loud, but it was like. It was important to me to say she was very confused by something she'd done. And I was like, no, you were an asshole.
B
Clearly you care about that person.
A
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 ass ourself. But it is really important, and people find it really hard to do that.
B
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. I 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 it, not optically doing it. And 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.
A
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?
B
By when someone here says something to you, when someone rewarding it.
A
Right. You explain, you should thank you for that shit.
B
Not only thank you in private, like when employees says something.
A
Yeah. In front of everyone.
B
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.
A
Yes.
B
But he said something interesting. He said, well, what if you don't act on any of 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. 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 is sensitive.
A
Yeah.
B
And sees, like a kid shit on me. And they're like, what are you doing now? For everyone who's listening, don't be this person. No. 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. They want to show that they'll push back, but they're pushing back on some dumb shit. You have to make sure the business you're standing on when you're pushing back against the lead player, there's real stuff. Yeah. You better not for sure.
A
Don't come with some push and I
B
will kill you now.
A
I'm going to murder you.
B
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.
A
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. And 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 positive feedback Lift each other up. It's like, you know what? 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.
B
Of course.
A
We actually need more tricks.
B
You become an enabler of something that isn't right.
A
Yes.
B
And that doesn't mean you're not a girl's girl.
A
No, it doesn't mean you're not a girl's girl. Quite the opposite.
B
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.
A
Yes.
B
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.
A
Yes.
B
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 am deeply coming from love, because I think you're a badass bitch. But in this moment, like every human, I think there was a little. You know, it's how you deliver it.
A
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 gonna be honest, but I don't need to be brutal.
B
Correct.
A
And I think that that is so important. You can give it to people straight without being a dick.
B
You 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.
A
Yeah.
B
And I misunderstood for a long time.
A
For a long time.
B
For 20 years.
A
I'm glad to talk to you about that because I think it is such a. 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. Your 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 understand.
B
I also think a lot about pendulum swings. Like right now with the explosion of digital, I'm getting very excited about analog.
A
Glad you went there, cause that's what I want to talk to you about.
B
Good. I believe that society pendulum swings every 5, 10, 15, 20 years, whatever it may be. Baggy jeans, tight jeans. Baggy jeans, right. You know I know about the jeans. I know you do. I think we've gone through an era of 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.
A
I'm like, can that era just come?
B
I smell it. I do this for a living. I smell it. I'm starting to see the earliest cracks.
A
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.
B
But fatigue of trends, you literally just
A
think it's being an asshole has just gone full circle. Winning while being an arsel was unful circle.
B
We just kind of went, 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.
A
Fuck yeah, of course I am. Stay on this fault 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 we were raised, even day to day.
B
I travel a lot. When I watch a 80 year old woman get to the airport gate and I see 1920 year olds just sitting
A
there, oh you gotta be fucking kidding me. And I'm like, someone help out, like
B
please God, somebody else. 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.
A
There's a particular kind of fantasy that gets built into a wardrobe. When you put on the right outfit for a moment. You don't just look different, you move differently. You carry yourself like the person you're supposed to be getting dressed to be. That's something I've always believed about clothes. They're not just decoration. They're a small daily act of actually becoming the brands and the designers that understand that are the ones who actually change how people see themselves. Not by selling them a trend, but by giving them a piece that lets them step into a version of their own life that feels a little more elevated and a little more intentional. That's what makes Macy's new collab worth talking about. On 34th is Macy's own private brand known for wearable city inspired pieces. What's really exciting is that they've just teamed up with the Molly Rogers. She's an Emmy winning costume designer behind some of the most iconic fashion forward New York TV looks of the last few decades. She created what now feels like quintessential New York style. The kind of wardrobe you saw on TV that made you want to invent your entire closet overnight. For this collection, she reimagined some of the most unforgettable looks from her career and translated them into pieces. You can actually wear real life clothes with a costume designer's eye behind them. What's interesting about a great costume designer is that they're not designing for trends, they're actually designing for character. They're answering the question of who someone is before they even speak. And that's a real craft and those details are where it really comes alive. Pockets. You don't expect prints with personality, small touches that make you feel like you're wearing something with a story. That is what I love about a collaboration done well. It's not just access to a name, it's access to a point of view. A piece of someone's creative vision that you can carry into your own life. And given the kind of summer that most of us have coming up, events and trips and the moments you want to feel like the best version of yourself walking in. This is exactly the kind of collection that earns its place in a wardrobe shop. The collection now at Macy's or in store. Beauty and longevity have been linked in the Wellness conversation for years. But what's interesting is that the formulations are getting much sharper. Peak just launched a great example with their new Carrara marine collagen. Built around the idea that what's happening underneath matters more than what you see on the surface. What stands out to me is the formula. It combines type 1 marine collagen that supports radiant skin with rare type 2 collagen for deeper structural support. They've also added biotin and pearl powder to support the skin and hair and nails. It's clinically shown to support skin elasticity and joint agility in as little as two weeks. And it's the only collagen clinically proven to support healthy cellular aging, which is a level of formulation you just don't usually see in this category. This is a smarter way to think about collagen built for how your body holds up over time with the surface benefits as a bonus. Peak is offering 15% off plus free gifts for the launch. So it's a great time to try it while it's it's brand new@peaklife.com aspire that's P I Q U A life.com aspire. So if you're a graduate, 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
B
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 gotta get a job. We completely fucked it up. It's backwards. Yeah, 22, 30 is insanity.
A
No, it's fuck around time.
B
And 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. I'm not gonna dunk.
A
Never do shit.
B
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 gonna get you to work as hard as it's gonna require to break into something and then are you actually good at it?
A
That's the kicker. Yeah. And are you good at it?
B
Are you good at it?
A
Are you good at it?
B
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. And 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.
A
You literally are like, boy, me, is he not? Do you know why they're all laughing?
B
Why?
A
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. Go, Gary. Just go.
B
Life is not school. You are not gonna learn how to be an entrepreneur by reading an entrepreneur book. You. We 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.
A
But can I tell you, this is one of the things that 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 ruin their lives and have no balance. I believe that proximity and visibility, the other way around, coming back at you, you being seen, you being in the right space, you being in 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.
B
And look at that.
A
You have to do that in real life.
B
Look at how KK took that feedback from her. Wow, he's so gracious.
A
And then put it in his work tomorrow.
B
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. Yeah. It's much more detailed than just the black and white. It's the gray.
A
It's the gray. And it's so interesting. Cause I sat in a job that I felt extremely undervalued in in my early 20s. 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.
B
We'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.
A
No.
B
And by the way, if you're such a whiz kid, go do it.
A
Go do your thing. Yeah, yeah, take your shot.
B
Because by the way, there's unlimited 23 year olds cooking with social media. There's unlimited 23 year old 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? Yes, this is the greatest era ever for 20 year olds. You have 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, and when I say you suck, that's not bad. Because the cool part is you have unlimited time to dominate.
A
Yeah, you do.
B
Unlimited.
A
Yeah, you do.
B
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. Cause 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?
A
Which part are you listening to? Well, whatever you choose to listen to. Right, Whatever you choose.
B
Like your focus, Emma. Life is very simple. You find what you're looking for you think the world sucks. Good news. You find it all day long. Yeah, but you wanna think the world's awesome good news. There's unlimited things to see. You choose.
A
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. Cause that is something that I think is so needed in the world right now. And I love that. Cause I think I've always been the Michelle Obama and gone high. So that feels good for talk to me about. Because I've seen you speaking so much about the next trends and you predicted YouTube, you predicted, you know, so many of these, like big social movements, how important social commerce was going to be. And now you are non stop 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.
B
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.
A
Not that many.
B
You know, 20 years ago, like, why are guys bringing back these weird mustaches? You know, four years ago, back to the jeans, like, uh oh, skinny's out. Like here comes the. You know, like why? Why?
A
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 de understanding and knowledge.
B
That's right.
A
And then you're applying them and making money from them.
B
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 gonna sell on TikTok Shop this year. I'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 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. You know, I was right about social media. Like top eight, top eight had already happened on MySpace. I knew it was just gonna keep building. Live shopping happened in Asia a decade ago and it's been happening on whatnot.
A
But it's been slow to take off here. Right? Because again, I have brands that are huge on TikTok shops. And yet live shopping is something that we haven't quite cracked yet.
B
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.
A
It's a different thing.
B
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.
A
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
B
off here because you have to know what Americans do. You need to know what.
A
But.
B
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 know, it's very, no, no, no, no. 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 wannification of every category. What does that mean? That means $150 suntan lotion. That means $65 band aids. That means $130 pack of bubble gum 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.
A
So you don't see that changing.
B
It's probably almost my life's work of hoping that can change. But no, we've got deep rooted human truths that, you know, ebb and flow through society through moments in time in 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. There 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.
A
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.
B
Yes.
A
How do you, Gary Vee, sit there and say, all right, you know what, I'm gonna try something. I heard, I listened to Gary and he said that, you know, this whole online shopping thing's gonna take off. Like, what are the next steps?
B
They literally take out their phone right now and they go to Claude or ChatGPT or Gemini. Cause 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 whatnot 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?
A
How do they get into better health?
B
How do people get into better physical health?
A
By fucking doing it.
B
Correct.
A
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.
B
Business, life, everything. It's actually shockingly simple. On paper, it's incredibly hard to be disciplined.
A
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.
B
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, and 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?
A
Facts, facts.
B
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?
A
Are you okay?
B
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 is she's not happy with her marriage right now, or 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.
A
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.
B
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 Garina. Garina, 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, it'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?
A
Yeah. I'd be like, sally, do me a favor, get the fuck out of my face. Buy a fucking pants support Sally, shut
B
up and buy the fucking club.
A
Tell your mate.
B
Be a girl's girl.
A
Come on, Sally, you remember Avon. When those ladies will come around to your house, my mom would be like, buy a lipstick. Like, get, do what you can.
B
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
A
make a video of it, you're off to the races.
B
And if, God forbid, for some ungodly reason that video gets 14,000 views and you make $83 there, I'm watching person after person after person. This is an E commerce that you and I did not grow up with. They don't have inventory.
A
No. And by the way, we are doing that with all of our brands. Of course you are working.
B
It's crushing.
A
Unbelievably. Well, it's crushing. Crushing.
B
That's affiliate. And then they're 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.
A
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? You have obviously honed this over a long time, but what is it that people should actually be paying attention to?
B
First, 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.
A
They do hate change.
B
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. End Substack Beehive.
A
You're like, what?
B
Like.
A
I'm like, I was killing it on these other platforms.
B
I wish we just still had email. I was the king of email in 97. I don't get excited when a new thing comes along, but I have a responsibility to be a winner. And 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.
A
Yeah.
B
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 gonna make fun of you, and then they're gonna ask you how to do it. That's what's gonna happen. So I think it's a couple things. One, don't be romantic. Don'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?
A
Why?
B
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.
A
Yeah, you just read exactly. What can you say? Yeah. If you don't understand.
B
Yeah, you know, and so that's it.
A
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B
This episode is brought to you by
A
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B
book to screen favorites you've already read twice off campus.
A
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Your next obsession is waiting.
A
Watch only on Prime. If 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?
B
I'd make content on the Internet either about things I know, if I still had my knowledge. I would talk about. 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.
A
No, it doesn't. The algorithm doesn't give a fuck. And you can only really appreciate that and understand it. And I'll contextualize it because when you came up in the fashion industry, the key to the kingdom were held by three people, right? It 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. Now it's completely democratized.
B
Completely.
A
Completely.
B
At a scale that is insane.
A
So what do you think that this generation have got going for them? That like no other generation has had opportunity? Yeah.
B
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. When I was coming up the game you had to eat shit for 15 years to begin the first phase of opportunity.
A
You should eat a little bit of shit, though.
B
No, I'm a big fan of.
A
I mean, I think so.
B
I love eating Tunisol. I think I'm saying it right now. I believe that adversity and humility are foundational to joy. Foundational to joy.
A
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.
B
And there's another thing. Kids learn pretty early when their parents are full of shit. Like 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.
A
Yeah.
B
Stop bullshitting your children.
A
This is why you credit your mom with so much.
B
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 at my. I am my mother's byproduct.
A
I love that it's true. I know my son speaks about me like that when he's older. I do not exist. I'm like, damn right you don't. What is she like? Is she so proud of you, your mom?
B
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 gonna be that kind of person that in her 50s and 60s, still glam. 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.
A
End of, end of. It really is that simple.
B
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.
A
Gary, if you could change one thing that the next generation believes to be true, specifically about success, what would it be?
B
It is actually my North Star 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 jun 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 like wrong right now in their Beamer wrong. What they don't know is how much they left on the table. Because nothing ever came to them. Cause 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.
A
That is the truth. Yep. That is the truth.
B
Yes.
A
Or I'll be happy if your next prediction comes true.
B
The civility.
A
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.
B
It's coming. We're tired. That's why the 60s looked differently in the 70s with disco. And 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.
A
No, we cannot.
B
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.
A
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 like so much drags them down. So how do you actually cultivate that
B
in your life for the audience? It's be the person you wish. Everyone. This shit 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. Be empathetic, maybe shit's fucked up for them. Everyone thinks the whole world revolves around them.
A
It does not.
B
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. Cause all the receipts are online. During the hardest 10 years when everyone was shitting on everyone. I shit on.
A
No, you didn't. Nope. That was choice for. It's just not who you are. Do you ever feel like shitting on
B
someone like Tom Brady and Michael Jordan? Because I love sports. So they hurt my feelings because they beat my feelings.
A
They killed you in sports.
B
I do it a lot.
A
Yeah. Yeah. That's different.
B
Correct. It's a fake word.
A
That's not me.
B
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? You know how fucked up that. Like.
A
No, that's psychotic. It's actually fully psychotic. You know that?
B
It's like, on what planet was that a good use of three minutes?
A
Who was your mother? If you don't have anything nice to say, don't fucking say nothing.
B
I'm so pumped that you're excited about this. Oh, no, no, no, no.
A
It's the best thing. Best thing I've ever heard.
B
I can't wait to see best thing I've ever heard. I'm like, now so hyped to see you in seven. I'm gonna see you somewhere in seven.
A
Are we gonna say, man.
B
And you're gonna be like, how the fuck. Because we.
A
I'm praying for it.
B
I'm praying for it. Let me tell you exactly why it's gonna happen. We get tired.
A
We're over the end of the.
B
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 gonna pendulum up.
A
I'll be on the other end of that pendulum swing. I'll take it. I wanna believe that.
B
And you have the ability to impact.
A
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. And I think that you choose your choice. You choose how you react to the world every single day.
B
I just think it's crazy to go roll in the mud with the other pigs.
A
Totally. I mean, listen, I'm gonna start with yourself, girl. It all starts here. You can choose.
B
You're in control.
A
I'm moving you to rapid fire.
B
Let's do it.
A
All right. I'm the worst at rapid fire, by the way. I don't even know how to do it.
B
I'm remarkable at it.
A
So we do all you.
B
We'll be solid at this. We'll be average. That if you're the worst, then I'm remarkable.
A
What's one habit that's had the biggest impact on your career?
B
Accountability. I think everything is my fault. It is the foundation of my success and I like it.
A
You are good at rapid fire. What is a business opportunity that you passed on that you were to going well? Did you have loads of them?
B
Sure. I missed the email from airbedandbreakfast.com that begged me to invest. That was bad. I passed on Uber twice. If I wrote my normal $50,000 check, I would have had 500 million. That was bad.
A
That was bad.
B
I mean, there's. I mean, there's. I could take up four hours.
A
You're done. You're good.
B
Yes.
A
You had me at 500 million. What's the most important thing that you've changed your mind about?
B
That candor is good. I 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.
A
I hope people really listen to that one. Is there a book that changed your life?
B
My reading comprehension is non existent.
A
And yet you're like, I got a
B
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 for four lines, four sentences.
A
Couldn't get through it.
B
I replied, set up a 15 minute meeting. I have no reading comprehension. I've read less than 10 books.
A
So 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? Cause 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? Cause mine comes at me mostly through books. So where does it come from? For you.
B
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.
A
Really.
B
If I see it or I hear it. So I'm constantly. Yeah. So I'm killing it, you know.
A
Yeah.
B
But I have to hear it or see it.
A
That's the only way that it goes in.
B
Yeah.
A
What is something that you still aspire to?
B
You know, I still think I'm dramatically under indexing professionally. I mean it. I genuinely believe I'm gonna build much bigger companies, much more impact. This Vee Friends thing is big for me. It's gonna be my legacy.
A
You think so?
B
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. That's why I say Jim Henson, Fraggle Rock, the Muppets, Sesame.
A
Sesame street was insane. Can you imagine?
B
So I've got a lot of professional goals. Personal, very little. Like. I feel very good at 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.
A
Wow. All right, we'll be watching this face.
B
Thank you.
A
Amazing. Thank you, Gary.
B
Thanks, Sim.
A
Such a pleasure. If 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 Griffin. Emma Greed is presented by Audacy. I'm your host, emma greed, Ashley McShan, Derrick Brown and me. Our executive producers from Audacy. Leah Rees, Dennis, Asha Saludja, Lauren LeGrasso Producer, KK Sublime. Stephen Key is our senior producer. Sound design and engineering by Bill Schultz. Angela Peluso is our booker. Original music by Charles Black. Video production by Evan Gladstone Cox, Kirk Courtney, Andrew Steele and Carlos Delgado. Social media by Olivia Homan, Katherine Bale. Special 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 Meekol, Sean Cherry and Lauren Vieira. If you have questions for me, you could DM me @aspirewithemagree. 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. Emma Greed me.
In this episode, Emma Grede sits down with Gary Vaynerchuk ("Gary Vee"), digital media pioneer, entrepreneur, and CEO of VaynerMedia. Together, they delve into the upcoming shift in culture: why kindness, humility, and radical truth will soon become the key attributes for personal and professional success. They explore topics such as overcoming fear and insecurity, the importance of reputation, building self-awareness, the future of business and digital culture, and how the next generation can best prepare themselves in a rapidly changing world.
Insecurity is the root: Gary asserts that insecurity, especially the fear of judgment, is the main thing that holds people back.
Fear as fuel, but not forever: Fear and insecurity can drive initial ambition but are unsustainable sources of motivation.
Handling criticism: Gary attributes his resilience against criticism to a natural empathy; negative comments reflect more on the critic’s state than on him.
Self-worth and market validation: Early entrepreneurial validation gave Gary confidence to drown out negativity.
Self-awareness as superpower: Knowing oneself, and creating conditions where others can speak honestly to you, is fundamental.
The role of humility:
Kind Candor: Gary introduces the idea of "kind candor"—truthful feedback delivered with genuine care.
The next big thing is live shopping and social commerce: Gary explains how shifts seen previously in China are about to boom in the U.S., especially via TikTok Shop.
Don’t romanticize the past:
| Timestamp | Content | |---------------|------------------------------------------------------------------------------------------| | 05:45 | Emma & Gary discuss fear and insecurity as root barriers | | 09:10 | The taboo of taking lifestyle “steps back” and the role of regret | | 12:33 | Entrepreneurship: How to know if it's for you | | 14:05 | Gary's radical empathy and armor against criticism | | 16:33 | The decline of accountability and rise of blame in society | | 21:49 | Parenting for confidence and resilience | | 26:25 | Debunking "nice guys finish last" | | 27:46 | Self-awareness as critical to leadership | | 29:12 | Humility as a superpower and approach to feedback/candor | | 35:28 | The coming pendulum swing to kindness and civility | | 40:27 | Gary's advice for people in their 20s: take risks, pursue proximity, avoid delusion | | 47:34 | Live shopping/social commerce as the next business wave | | 52:21 | Overcoming fear of public failure and the “pity of the hurt” | | 55:37 | Adapting to change; not romanticizing the past | | 59:21 | Starting from zero today—the democratization of opportunity through social media | | 62:33 | How parental praise shapes identity | | 63:03 | Reputational assets and long-term winning |
Gary closes with his core belief that being good, decent, and kind is actually the most sensible and sustainable route to real success. Emma notes her hope that his forecasted pendulum swing toward civility comes true, emphasizing the need for optimism and action in our everyday interactions.
Emma [67:15]:
"You’re in training for the type of person that you want to be. ... You can choose. You’re in control."
Gary [64:55]:
"Be the person you wish everyone was. This shit is so simple. Be better. Be nicer."