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Gary Vaynerchuk
CEO; Chairman of VaynerX, VaynerMedia

Gary Vaynerchuk: Why Truth, Humility, and Kindness Will Become Your Next Superpower

📅 May 26, 2026 Emma Grede and GaryVee 71 MIN 99614 VIEWS 433 SEGMENTS · 2 SPEAKERS
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 peop...

Questions asked in this interview

12
  1. 2:42What's the most important thing that you've changed your mind about?
  2. 9:05So what was it that drove you then?
  3. 10:51What do you mean? In your own head?
  4. 12:45Because I do actually believe it's a really important part of being successful that you start to drown out the noise, right?
  5. 19:43What I'm interested in is like 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?
  6. 21:48What is it that those people all have in common?
  7. 29:22So, how do you cultivate the type of conditions that allow people to tell you the truth?
  8. 40:25Like, do you know why they're all laughing?
  9. 48:42So you don't see that changing?
  10. 54:02Like, you have obviously honed this over a long time, but what is it that people should actually be paying attention to?
  11. 1:03:01Gary, if you could change one thing that the next generation believes to be true, specifically about success, what would it be?
  12. 1:07:46What's one habit that's had the biggest impact on your career?
Emma Grede 0:00 ↗
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 5 years are going to belong to people who are kind and have humility, those who want reputations worth defending. And he's not saying it because it sounds nice. He'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 3 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 were starting from zero today. That's the part you want to write down.
I feel that the worst sentence on earth is nice guys finish last. Gary Vaynerchuk has been telling people what's about to happen on the internet for years before they're ready to hear it.
Gary Vaynerchuk 1:59 ↗
Social media changed no one. Social media exposed everyone. The reason most people don't see what I see is because they don't want it to happen.
Emma Grede 2:07 ↗
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. We are clearly in a moment where decency is completely unraveled.
Gary Vaynerchuk 2:22 ↗
I didn't realize then insecurity was the more prevalent fuel to get to the top. We've lost the art of not giving a damn.
Emma Grede 2:30 ↗
He was early to YouTube, Twitter, TikTok, and now he can see the cracks forming.
Gary Vaynerchuk 2:34 ↗
I actually think we're in the pre-dawn of a very good era for good people. And your reputation is your biggest asset.
Emma Grede 2:42 ↗
Oh, I'll be happy if your next prediction comes true. What's the most important thing that you've changed your mind about?
Gary, welcome to Aspire.
Gary Vaynerchuk 2:58 ↗
Thank you for having me.
Emma Grede 2:59 ↗
Well, I'm very, very excited about our conversation. And I feel like with you and I, there are actually 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 kind of, you know, 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.
Gary Vaynerchuk 3:47 ↗
Insecurity, 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 and 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 the question directly is insecurity.
Emma Grede 4:41 ↗
So what do you say to people that are living with real fear, like fear that comes from a place of, you know, real concern perhaps that, you know, they don't have the circumstances that are best, but they really want to, they really want to move forward in their life? Like how have you in your own life been able to do that?
Gary Vaynerchuk 4:59 ↗
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.
Emma Grede 5:13 ↗
Yes, it is.
Gary Vaynerchuk 5:14 ↗
You know what I mean?
Emma Grede 5:14 ↗
You experienced fear. You must have at some point.
Gary Vaynerchuk 5:16 ↗
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.
Emma Grede 5:24 ↗
Yeah.
Gary Vaynerchuk 5:25 ↗
It was a big, real big thread in my life. My mom lost her mom at five. My father lost his dad at 15.
Emma Grede 5:33 ↗
So it was a legitimate fear.
Gary Vaynerchuk 5:34 ↗
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 stuff that I think by the time I got to 18, I'm like, 'Oh, we're cooking now.' Like, I'm not scared of anything.
Emma Grede 5:54 ↗
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 losing money. I'm just like, that's not real. Like that's not actually something to be really scared about.
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?
Gary Vaynerchuk 6:31 ↗
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. 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, 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.
Emma Grede 7:26 ↗
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?
Gary Vaynerchuk 7:41 ↗
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.
Emma Grede 7:56 ↗
In what way?
Gary Vaynerchuk 7:57 ↗
I was like, 'Oh, 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 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.
Emma Grede 8:30 ↗
Yeah.
Gary Vaynerchuk 8:30 ↗
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've had content before I started which did not take away any of my ambition.
Emma Grede 9:05 ↗
So what was it that drove you then?
Gary Vaynerchuk 9:07 ↗
I want to make my parents proud. And 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.
Emma Grede 9:18 ↗
Oh yeah.
Gary Vaynerchuk 9:18 ↗
I'm that bug. What the hell 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. I don't even really buy stuff. I like having money for optionality and time, but I don't want stuff.
Emma Grede 9:34 ↗
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 the way that we're talking about entrepreneurialism now, starting a business, being a founder, is actually for you or not?
Gary Vaynerchuk 9:54 ↗
Jumping in the pool.
Emma Grede 9:56 ↗
Nothing to it but to do it.
Gary Vaynerchuk 9:57 ↗
There's no weird test. There's no report.
Emma Grede 10:01 ↗
Isn't that what's so hard for people to understand though? You just got to do it.
Gary Vaynerchuk 10:05 ↗
Yes. Because they're scared to fail.
Emma Grede 10:06 ↗
Mhm.
Gary Vaynerchuk 10:07 ↗
But if you're scared to fail, it's already the first tell that you're not an entrepreneur.
Emma Grede 10:11 ↗
I think it's really important to contextualize like 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?
Gary Vaynerchuk 10:37 ↗
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.
Emma Grede 10:51 ↗
What do you mean? In your own head?
Gary Vaynerchuk 10:53 ↗
Yes.
Emma Grede 10:54 ↗
You've been able to tune everyone out?
Gary Vaynerchuk 10:56 ↗
Everyone, including even the ultimate, my mother, who's everything to me. How? I'm not sure.
Emma Grede 11:02 ↗
Well, because listen, I mean you have put yourself in situations, you know you're so huge on social, you have non-stop messaging, rhetoric, you know, criticism, you know, fantastic, you know, critique coming your way. How have you been able to do that?
Gary Vaynerchuk 11:18 ↗
My best guess at this moment in my life is some sort of almost probably not even proper over-indexing on empathy.
Emma Grede 11:29 ↗
Please explain that to me.
Gary Vaynerchuk 11:31 ↗
Anytime someone shits on me, whether it was a teacher in fourth grade or a classmate or Johnny Pants 47 on Instagram, I just know that if they're saying something bad about me, it's because they're in a bad place.
Emma Grede 11:44 ↗
And how quickly do you go there? Like immediately as you're getting the shit really.
Gary Vaynerchuk 11:49 ↗
And I got there, it takes training. And again, this is why I think about natural DNA a lot.
Emma Grede 11:55 ↗
Yeah. Yeah, for sure.
Gary Vaynerchuk 11:56 ↗
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 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 shit. 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. Like, I was getting so much positive affirmation from the market. Somewhere between fourth and fifth grade, my head just went into some really 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 you.
Emma Grede 12:45 ↗
So, how do you get out of that? How do you give less of a damn? Because I do actually believe it's a really important part of being successful that you start to drown out the noise, right? Like 100%.
Gary Vaynerchuk 12:59 ↗
Yes, I would say that I've become infinitely more successful the less that I have listened to other people.
And more importantly, and 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 fucks.' 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 Dead Sea where you can just lay and you're floating? 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. 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 Britney back. Like, it's just what we do. It's what we do. It's what society does.
Emma Grede 13:47 ↗
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.
Gary Vaynerchuk 14:00 ↗
They're believing politicians.
Emma Grede 14:02 ↗
Say more.
Gary Vaynerchuk 14:03 ↗
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.
Emma Grede 14:11 ↗
And you believe that people are just eating that up.
Gary Vaynerchuk 14:13 ↗
It comes from a lack of responsibility. Well, let's play it out.
Emma Grede 14:16 ↗
Yeah.
Gary Vaynerchuk 14:16 ↗
You're unhappy. Your life sucks.
Emma Grede 14:18 ↗
Yeah.
Gary Vaynerchuk 14:19 ↗
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?
Emma Grede 14:27 ↗
Well, I mean, listen, 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 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 though? And why are people being so swept up? Like why is there such a lack of responsibility for ourselves?
You think it all comes back down to insecurity?
Gary Vaynerchuk 14:56 ↗
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.
Emma Grede 15:29 ↗
Why do you talk on this so much though? I find it so interesting because you do like you come back to this point. I see it.
Gary Vaynerchuk 15:36 ↗
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.
Emma Grede 15:57 ↗
How much of that do you see?
Gary Vaynerchuk 15:59 ↗
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.
Emma Grede 16:06 ↗
Ah, so you're actually looking at everything.
Gary Vaynerchuk 16:10 ↗
I used to on a flight to LA like this read four and by the way I still like to do it because I'm a little old. 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 and gossiped on the bench and didn't give a shit. What 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, whatever woman or man came up with like let's give everyone a trophy came from a good place.
Emma Grede 17:01 ↗
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 how you can get there.
So, I'm doing what I do best, sharing and never gatekeeping what's worked 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 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 emgrede.com to purchase the book. Also available on Amazon, your favorite audio platforms, and all good bookshops.
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What I'm interested in is like 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?
Gary Vaynerchuk 19:52 ↗
That their parents tricked them into thinking like that work ethic and like that real life isn't real. Their expectations got whacked.
Emma Grede 20:01 ↗
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, you know, we're in a market and a time right now where we are actually a little bit unsure of what we're even, you know, growing our kids up to do, you know, what is going to be left for them. So I understand where there is 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?
Gary Vaynerchuk 20:41 ↗
Build confidence. And confidence can only come from what they do, not what you do for them.
Emma Grede 20:46 ↗
Got it.
Gary Vaynerchuk 20:47 ↗
It's that simple, right?
Emma Grede 20:48 ↗
It's really that simple.
Gary Vaynerchuk 20:48 ↗
It's really that simple.
And it's really like it's that simple and it's fucking hard.
Emma Grede 20:53 ↗
Yeah. No, like 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?
Gary Vaynerchuk 21:07 ↗
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 because I do this like, you know, it's so easy to talk about it in the abstract.
I'm sitting here on a podcast so I could talk about it in the macro. When it gets to those little ones that you love more than breathing, you like it's so hard but it is the answer.
Emma Grede 21:48 ↗
It is the answer. It is the answer. I 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?
Gary Vaynerchuk 22:04 ↗
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.
Emma Grede 22:21 ↗
Yeah.
Gary Vaynerchuk 22:22 ↗
Some of it silly like early youth just like they want stuff. They just want status.
Emma Grede 22:27 ↗
That was maybe a bit of me.
Gary Vaynerchuk 22:28 ↗
Yeah. I mean that's just like normal.
Emma Grede 22:29 ↗
It was that simple.
Gary Vaynerchuk 22:31 ↗
Yeah, it's not super complicated. Like they put a specific person on a pedestal and they want to emulate.
Emma Grede 22:37 ↗
Um.
Gary Vaynerchuk 22:37 ↗
That'll work too to a degree.
Emma Grede 22:39 ↗
Yeah, I mean it works to get you so far.
Gary Vaynerchuk 22:41 ↗
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 like I don't know. Like I can't help it. Like this is just what I want to do. I want to create.
It's Alex can give you a story on this. I was once in Turks and Caicos. I watched this kid once build the craziest sand castle situation I've ever seen in my life. Worked on it for 7 hours. This 8-year-old was a 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 I don't know out of everywhere like the day comes to an end and his parents call him to go clean up because 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.
Emma Grede 23:50 ↗
Wow.
Gary Vaynerchuk 23:51 ↗
That's me. I am not doing any of this Gary. You would be flabbergasted how detached I am from the GaryVee brand for 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.
This kid was just in his bag on this sand castle. 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.
Emma Grede 24:28 ↗
I feel like you wear the 'I don't care' like it's a badge of honor. Why is that so important?
Gary Vaynerchuk 24:36 ↗
It's actually different, Emma. It doesn't come from a place of like audacity or I'm it's 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 because I have great joy of the deposits I'm leaving in the world. I feel a sense of responsibility even on what I'm 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. It'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 shit. It's also not true.
Emma Grede 25:59 ↗
Yeah. No, I listen, I married a nice guy. I can't even imagine. I can't imagine anything else like and I actually really when when I think about attributes in business, it really benefits you to be nice. It's really good if you're especially if you're playing long.
Gary Vaynerchuk 26:15 ↗
Well, of course. I mean, we're trying to be like I'm playing long.
Emma Grede 26:18 ↗
Yes, you have to.
Gary Vaynerchuk 26:19 ↗
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 like do all this frivolous shit go fast. Fuck it. Nice. Knock yourself out. It's not what I'm trying to do.
Emma Grede 26:33 ↗
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?
Gary Vaynerchuk 26:42 ↗
Resilience, tenacity, curiosity, patience, you know, self-awareness is number one. If you don't know yourself, you're finished.
Emma Grede 26:55 ↗
How do people get to know themselves, though? Because I really think that that is true. And there's 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.
Gary Vaynerchuk 27:13 ↗
Putting the people around you in a position to tell you the truth without ramification.
Emma Grede 27:18 ↗
Yeah. Which is harder the more successful you get.
Gary Vaynerchuk 27:21 ↗
Or not.
Emma Grede 27:22 ↗
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 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, you know, she was very confused by something she'd done and I was like, 'No, you were an asshole.'
Gary Vaynerchuk 27:44 ↗
Clearly, you care about that person.
Emma Grede 27:45 ↗
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 self.' But it is really important and people find it really hard to do that.
Gary Vaynerchuk 27:55 ↗
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, you know, 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.
Emma Grede 28:57 ↗
And I think that's a common trait for people that are really doing it.
Gary Vaynerchuk 29:01 ↗
Yeah.
Emma Grede 29:02 ↗
Like really doing, not optically doing it.
Gary Vaynerchuk 29:05 ↗
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.
Emma Grede 29:22 ↗
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?
Gary Vaynerchuk 29:34 ↗
By when someone here says something to you, when someone rewarding it, right? You should thank you for that shit.
Emma Grede 29:42 ↗
Not only thank you in private like when an employee says something to me.
Gary Vaynerchuk 29:44 ↗
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.' 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.
Emma Grede 30:05 ↗
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.
Gary Vaynerchuk 30:12 ↗
Yeah.
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 a 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 who sense of themselves. Yeah. And sees like a kid pushing back on me and they're like, 'What are you doing?'
Now, for everyone who's listening, don't be this person. Now, 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. Yeah. Like you have to make sure the business you're standing on when you're pushing back against the lead player.
Emma Grede 30:58 ↗
There's real stuff there.
Gary Vaynerchuk 30:59 ↗
Yeah. You better not. Don't come with some and I will kill you. I'm going to murder you. I'm like that's very And I'm quick to be like that was cute. You're trying to show that you're not a yes person.
Emma Grede 31:08 ↗
Please explain one more time what the fuck you just said.
I love what you're saying because I think that we have created conditions often times 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, you know, positive feedback, lift each other up where 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. We actually need more truth. You become an enabler of something that isn't right.
Gary Vaynerchuk 31:52 ↗
Yes.
Emma Grede 31:52 ↗
And that doesn't mean you're not a girl's girl.
Gary Vaynerchuk 31:54 ↗
No, it doesn't mean you're not a girl's girl. Quite the opposite.
Emma Grede 31:57 ↗
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.
Gary Vaynerchuk 32:05 ↗
Facts.
Emma Grede 32:05 ↗
Right? People disguise candor to just be horrible.
Gary Vaynerchuk 32:09 ↗
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, a lot of times it lands.
Emma Grede 32:18 ↗
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.' But in this moment, like every human, I think there was a little, you know, it's how you deliver it.
Gary Vaynerchuk 32:35 ↗
It's all about how you deliver it.
Emma Grede 32:36 ↗
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.
Gary Vaynerchuk 32:59 ↗
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.
Emma Grede 33:22 ↗
And I misunderstood.
Gary Vaynerchuk 33:23 ↗
For a long time.
Emma Grede 33:24 ↗
For a long time.
Gary Vaynerchuk 33:24 ↗
For 20 years.
Emma Grede 33:26 ↗
I'm glad to talk to you about that because I think it is 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.
Gary Vaynerchuk 33:48 ↗
I also think a lot about pendulum swings. Like right now with the explosion of digital, I'm getting very excited about analog.
Emma Grede 33:53 ↗
Glad you went there because that's what I want to talk to you about.
Gary Vaynerchuk 33:56 ↗
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.
Emma Grede 34:05 ↗
I know about the jeans.
Gary Vaynerchuk 34:06 ↗
I know you do. I 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.
Emma Grede 34:35 ↗
I'm like, can that era just come?
Gary Vaynerchuk 34:37 ↗
I smell it. I do this for a living. I smell it. I'm starting to see the earliest cracks.
Emma Grede 34:41 ↗
What is giving you that feeling? Because I feel like a lot of people would be like, 'Please, good lord, let that be the truth.' But
Gary Vaynerchuk 34:47 ↗
Fatigue of trends. Like you literally just think it's being an asshole has just gone full circle. Winning while being an asshole has gone full circle.
Emma Grede 34:55 ↗
We just kind of went Yeah. 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 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. And
Gary Vaynerchuk 35:11 ↗
I actually think it's a trend. I think it's fatigue. Remember, I'd like to think everyone, you listen, I was a very bad student, but I was good at history. I'd like to remind everyone the 60s were pretty tumultuous.
Emma Grede 35:24 ↗
Fuck yeah, of course they were.
Gary Vaynerchuk 35:25 ↗
Like, stay on this foot though for me, Emma, because you are such a
Emma Grede 35:29 ↗
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 of how we raise...
Gary Vaynerchuk 35:44 ↗
Day to day. Even day to day, I travel a lot. When I watch an 80-year-old woman get to the airport gate and I see 19, 20-year-olds just sitting there, you got to be kidding me. And I'm like, someone please, God, even down to that level.
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.
Emma Grede 36:18 ↗
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So 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?
Gary Vaynerchuk 38:55 ↗
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.
Emma Grede 39:15 ↗
Yeah.
Gary Vaynerchuk 39:15 ↗
22 to 30 is insanity.
Emma Grede 39:17 ↗
No, it's fuck-around time.
Gary Vaynerchuk 39:18 ↗
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 going to do shit. I'm just going to 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?
Emma Grede 39:44 ↗
That's the kicker.
Gary Vaynerchuk 39:45 ↗
Yeah. And are you good at it?
Emma Grede 39:47 ↗
Are you good at it?
Gary Vaynerchuk 39:48 ↗
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.
Emma Grede 40:25 ↗
You literally are like, boy, me. Is he not? Like, do you know why they're all laughing?
Gary Vaynerchuk 40:29 ↗
Why?
Emma Grede 40:29 ↗
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.
Gary Vaynerchuk 40:40 ↗
Life is not school. You are not going to learn how to be an entrepreneur by reading an entrepreneur book. You need to learn by seeing it. It's the jungle out here. Lions become better lions by hanging out with lions.

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APA

Vaynerchuk, G. (2026, May 26). Gary Vaynerchuk: Why Truth, Humility, and Kindness Will Become Your Next Superpower [Interview transcript]. Emma Grede and GaryVee. CEOInterviews.AI. https://ceointerviews.ai/interview/3153050/

MLA

Gary Vaynerchuk. "Gary Vaynerchuk: Why Truth, Humility, and Kindness Will Become Your Next Superpower." Emma Grede and GaryVee, 26 May. 2026. Transcript, CEOInterviews.AI, https://ceointerviews.ai/interview/3153050/.

BibTeX
@misc{vaynerchuk2026_3153050,
  author       = {Gary Vaynerchuk},
  title        = {Gary Vaynerchuk: Why Truth, Humility, and Kindness Will Become Your Next Superpower},
  howpublished = {Interview transcript, Emma Grede and GaryVee. CEOInterviews.AI},
  year         = {2026},
  month        = {may},
  url          = {https://ceointerviews.ai/interview/3153050/},
  note         = {Speaker-attributed transcript with timestamps}
}