Why Humility is the #1 Skill a CEO Can Have episode artwork

EPISODE · Feb 9, 2026 · 46 MIN

Why Humility is the #1 Skill a CEO Can Have

from The GaryVee Audio Experience · host Gary Vaynerchuk

 In this episode, I reveal why the greatest skill to have as a CEO is humility. I share my philosophy on authenticity, explaining that being your "full self" is the only path to true originality. I coach several successful entrepreneurs who are hitting scale, advising them on whether to monetize "boulders" (big brands) or "pebbles" (community products). Plus, I share my secret for succeeding on TikTok Live and explain why my greatest skill is humility.You’ll learn about:The True Meaning of AuthenticityHow to Master the TikTok Live AlgorithmThe Boulders vs. Pebbles Monetization StrategyWhy My Greatest Skill is HumilityHow to Get the Right Leverage for Scale

In this episode, I reveal why the greatest skill to have as a CEO is humility. I share my philosophy on authenticity, explaining that being your "full self" is the only path to true originality. I coach several successful entrepreneurs who are hitting scale, advising them on whether to monetize "boulders" (big brands) or "pebbles" (community products). Plus, I share my secret for succeeding on TikTok Live and explain why my greatest skill is humility.You’ll learn about:The True Meaning of AuthenticityHow to Master the TikTok Live AlgorithmThe Boulders vs. Pebbles Monetization StrategyWhy My Greatest Skill is HumilityHow to Get the Right Leverage for Scale

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This thing I want to paint to you. It's my favorite one. I would watch a kid, like two kids, and they would build an immaculate sandcastle all day. And then about 5:30, 5:45, the parents would call and be like, Johnny, let's go out, like dinner.

Like, we're gonna go eat dinner. But eight hours building this immaculate thing, he would just look at it and be like, pshh, and run and smile. And I'm like, that's me. I just wanna see how big I can build it.

And then, I actually don't give a fuck about it. Just curious how good I am at the game. I'm wildly curious how big I can make it. Nothing else.

None. None of it defines me because I have my definition somewhere else. My definition is if people think I'm a good guy. This is the GaryVee Audio Experience.

So, my question for you is, I am also a teacher and a parent, and I just gave my 30-day notice for my teaching job. Wow. I love what I do. Is that because of this all?

Uh, essentially, yes. It makes sense. Yes. But what worries me is about, I think that I'm so good at what I do because I'm in the dirt, and I love coaching people.

Uh-huh. And I love getting my hands in there. Uh-huh. And I do one-to-one consulting as well, and I coach people with kid videos.

But like, I'm worried about getting that hands-on experience still to keep myself fresh and also potentially use this content, but then it's other people's children, and so how that would work. Well, I mean, you can go generic. I talk about a lot of business meetings where I try to mask who I actually talk to. Right?

So, you can go thematics. You don't need to be like, little Ricky Magoo on 42nd Maple Street, son of John. Right? You could be like, there was this little boy.

Yes. You could even say there was a child. That's what I do that now, but I mean like, working with a parent physically. Like, I like, like that aspect is what I'm worried about not having.

Well, so do physical stuff. You could create, for example, if you're saying you feel different physically than you do virtually in what you're doing, you could create a non-profit component where people apply to work with you physically once a quarter for two people or 10 people, just so you can taste it. It could be content for you, and it's a good give back. Or it could be a business.

Right. Right. Yeah. Listen, people will fly in for you.

This goes back to your worth. Like, you know, like, a lot of us didn't think somebody would pay $1,000 to talk to us for an hour. The next step is, wait, right, somebody would fly in and spend three days with me. So like, you can replicate that in a different way.

It's kind of like everyone's argument with me in college. I was bashing on college. Especially if you're collecting debt and you're creative or entrepreneurial. And people are like, yeah, parents are really, really shook when I take up.

They're like, yeah, Gary, but what about the experience of, like, being around people and leaving home? I'm like, go to Europe. You don't need to. Like, you can replicate growing up at 18 to 22, not by getting into $100,000 in debt.

Right. You can just go get a job in Kansas City. You can go to Norway. Like, you can grow up.

You don't have to be a teacher to be in the trenches. Right. You can replicate it in a different way. You understand?

Yes. You can do boot camps. You can do something. You can do a summer camp business.

I don't fucking know. You can do anything. Like an in-person summer camp. 100%.

You might love that. Yes. You like that one, right? I do love that.

Yeah. Isn't that good? Yes, I do. You like that?

Give me something. That was a good one. Yeah. Yeah, I mean, that's why I use that college analogy.

You're golden. I get why you value it. By the way, I value it. It's why my agency crushes because of GaryVee.

I'm the most practitioner of the craft. But you can replicate it. Okay. Thank you, Gary.

I hope you're enjoying the podcast right now. Make sure you follow the podcast. That's why I'm interrupting. Let's keep going on this show.

But follow the podcast. It'll make my mom super happy. Yeah, for me, I had Instagram for four years completely. No social media at all.

And then I decided I will start posting two times a day for two years straight. Why? Because I felt, I just knew I had to do it. I don't know why.

You just sensed it. I just sensed it. And um. It was hovering in your head for a long time or somebody said something somewhere and you just went.

I just went because I heard it like everywhere and I was just like feeling like I cannot, I cannot relate anymore. Got it. Got it. Yeah.

By the way, that's my big argument to like where the world, like everybody trying to protect their kids from technology. I'm like, by the time these five-year-olds are 18, we're gonna be in VR and AR glasses. Like, you know, like technology's coming in deeper, not like, but nonetheless, go ahead. Yeah, and I had agencies in Switzerland, um doing website designs, branding, so I kind of had to.

I got it. Got it. You're from a business hand. Now I understand.

Yes. Yes. And I, just my husband and I, we had it together. And he was absolutely against social media, just for himself.

Um, so I had to do it. And I did it and I saw that there was a big opportunity for mobile editing. Mobile editing. Mobile editing.

Yeah. Because um, people just love the way that I edited my videos. Yes. Um, and I sensed that it was a, was a market for it.

Yes. Um, and people were actually commenting under every single video, not about the content of the video, but how I edited it. Got it. Got it.

Yes. Um, but what worries me is about, I think that I'm so good at what I do because I'm in the dirt and I love coaching people. Uh-huh. And I love getting my hands in there.

Uh-huh. And I do one-to-one consulting as well, and I coach people with, Yep. Kid videos, but like, I'm worried about getting that hands-on experience still to keep myself fresh and also potentially use this content, but then it's other people's children. And so how that would work.

Well, I mean, you can go generic. I talk about a lot of business meetings where I try to mask who I actually talk to. Right? So you can go thematics.

You don't need to be like little Ricky Magoo on 42nd Maple Street, son of John, right? You could be like, there was this little boy. Yes. You could even say there was a child.

That's what I do that now, but I mean like working like with a parent physically. Like I like, like that aspect is what I'm worried about not having. Well, so do physical stuff. You could create, for example, if you're saying you feel different physically than you do virtually in what you're doing, you could create a nonprofit component where people apply to work with you physically once a quarter for two people or 10 people, just so you can taste it.

It could be content for you. And it's a good give back. Or it could be a business. Right.

Right. Yeah. Listen, people will fly in for you. This goes back to your worth.

Like, you know, like a lot of us didn't think somebody would pay $1,000 to talk to us for an hour. The next step is, wait, some, right, somebody would fly in and spend three days with me. So like, you can, you can replicate that in a different way. It's kind of like everyone's argument with me in college.

I was bashing on college, especially if you're collecting debt and you're creative or entrepreneurial. And people are like, yeah, parents are really, really shook when I take up. They're like, yeah, Gary, but what about the experience of like being around people and leaving home? I'm like, go to Europe.

You don't need to. Like you can replicate growing up at 18 to 22, not by getting into $100,000 in debt. Right. You can just go get a job in Kansas City.

You can go to Norway. Like you can grow up. You don't have to be a teacher to be in the trenches. Right.

You can replicate it in a different way. You understand? Yes. You can do boot camps.

You can do something. You can do a summer camp business. I don't fucking know. You can do anything.

Like an in-person summer camp. 100%. You might love that. Yes.

You like that one, right? I do love that. Yeah. See?

Isn't that good? Yes, I do. I like it. You like that?

Give me some. That was a good one. Yeah. You're welcome.

That's why I use that college analogy. You're golden. I get why you value it. By the way, I value it.

It's why my agency crushes because of GaryVee. I'm the most practitioner of the craft, but you can replicate it. Okay. Thank you, Gary.

I Yeah, so my kind of stand journey is pretty... Well, I say it's been like a year and a half, two years now. But I have something called endometriosis. It's a condition.

Yeah, I know it. Yeah, 10% of women have it. It's crazy. And I was like bedbound 50% of the month.

It was awful. Wow. And so I had all these great jobs with Procter & Gamble and Amazon. So I was super capable, but like the pain was just horrendous.

I'm sorry. And I was like, other people do social media. Why can't I give it a go? Because I had a hobby blog educating people on my journey, but not giving anything else.

Right. So decided to train to be a women's health practitioner. Learned about this crazy protocol and just started blogging it. So to your point earlier about documentation, I didn't have a business.

I was just blogging like day one, day two, day three. And it blew up. And then in all my comments, they were like, Please can you make a guide? So I made a guide.

It was like in the gym on a Stairmaster being like, How do I sell digital products because I don't understand technology at all. And then Kokomoa, a TikToker and YouTuber, made a video about Stan and was like, People sell on there. So I did it. And I went from making like a thousand pounds a month to the point where I was like, I'm gonna have to go back to my old job.

And we made a hundred thousand in our first month. Just from auto DMs and like one guide that was like 25 pounds, which is insane. So John reached out on Instagram and has like since changed my life because anytime I need help with my channel. That's the worst.

And he, again, like he was saying with Gary, like test me back every single time. And then because of all of those sales, I was able to publish this book, which I was gonna give to you. Amazing. Thank you.

So it's called the Anti-Inflammatory Day-to-Day Reset. Because of the auto DMs on Stan, it's the number one Sunday times bestseller, which is like insane. And it's just because of the auto DMs as well. And I know that you said your wife is like really into health.

Yes, loves. She will love that. Yes. And but my, my whole thing now is like, I'm so lucky and grateful that I found the answers for myself.

Yes. And I want to help other people find those too. I got it. So I started a women's health brand called Found.

And the whole point of it is to be the home of women's health. So if you ever have any questions about periods, menopause, whatever it is, you come to Found. Yep. So we have.

Like the knot was for weddings. Yes. Got it. Okay.

Understood. Keep going. So at the moment, we have guides. We've just launched a membership and we're going to launch a course, which is like a course version of the book.

If you were in my shoes, what would the next 12 months be? Aside from content, because I know that like content is absolute king, but aside from content. Surrounding yourself with talented people and paying them to do things that you don't like to do. What would be your key hires?

Like what are the MVPs? What don't you like to do? Yeah, all of it. Like operations.

I remember we were talking about this when you were in London. Like I love the creative. I love the talking to people. So you need a CLO.

You need an operating head. Yeah. And you think that would be sufficient over getting like a co-founder? Yes.

Because that's something I've been thinking about. You can get a co-founder second. Okay. No, you know, you don't marry the first person that you think you want to date.

You date them. You could get a head of operations and you may be like, oh my God, Johnny. Oh my God, Sally. You've been so profound to me.

I want to give you equity. Sally and Johnny are like, what the fuck? You're the best. We'll do it.

Because they just signed up for a job. No, I would not do a co-founder. Okay, so CEO first. Mm-hmm.

Okay, interesting. If you're pop committed to the content and you're pop committed to the content everywhere. Everywhere. Yeah.

Then the next thing in parallel is the hiring because you're starting to hit scale. Yeah. Of people that you really want to be in the trenches with doing jobs that you don't want to do. Okay.

And then my second question, my last one. We talked about how like if you're a woman trying to help women, this is like the best time. My ultimate goal is that we have clinics that people can come to and retreats to have like transformation experiences. Well, the good news is, you know this is coming.

Yeah. Right. The education is getting up. I know it because Mona is so deep in all the different things.

So that's good. It's going to happen. You just want to be a part of it. Yeah, exactly.

When it comes to some of that, it's like significant investment that you need to do it. I want you to keep growing your top line revenue and your business so that you have more leverage when you decide to raise capital. Okay. Got it.

What's that? Yeah. Everybody thinks, everybody wants to raise capital early because they don't have the capital. We now live in a world, especially with something like Stan, where you can make money.

The more money you can make, the more leverage you have for when you raise capital. The end. So I started real estate agent. My college professor was like, you're going to be an amazing real estate agent.

I went into that and I did great. I had two babies under two. And I'm like, there's no way I'm going out and cold calling and knocking on doors. I'm going to do one-to-many approach.

I got started in Idaho where no one was making content. And so they looked at me and was like, what are you doing? I was like, you're selling houses on Instagram and you don't have to leave and you're the top producer in our market. And I'm like, yeah, I am.

Like, tell me what you're doing. I need to know. And so I started one-to-one, launched my course on Stan. This is like now three years ago.

And it blows up. And I'm like making the six figures every month. And it's just crazy. I'm like, I can't even keep up with what's happening.

How much was it? All high ticket. So that course started out at like $2,500 and then I just raised my prices. Again, I just want to, there's certain people here that need to hear about this thing.

In real estate, there's a saying. It takes as much effort to sell a $25 million home as it does a $1 million home. Exactly. You heard me multiple times on the weeks of like, higher, higher.

You may be thinking, well, mine's not selling that well at lower. But I'm saying, if you've been listening, recontextualize it to the four-week challenge for Valentine's. Keep tuning. Keep tuning.

You understand? There's a lot more in this room. You might feel good. I feel like anxiety because I'm like, there's a lot more in a lot of you.

Tuning. Recontextualize. Make it, whether it's a digital product or an access to you or a group or a sauce dinner. Like, keep tuning.

But most of all, understand if you keep tuning, it allows you to do that. Right? LVMH is, you know, Louis Vuitton bags is better than Kate Spade's bags as a business, right? The average price, but it's a bag.

Right. Yeah. Like for this challenge, I probably sold a third of what a lot of y'all sold, but my price point was just a lot higher. So anyway, all that to be said, I take off, end up not completely leaving real estate, but obviously this becomes my full-time thing.

Everyone and their mom wants to know how do you stand and how to use it. And so now my DMs of how do you sell on real estate on Instagram are becoming, Jenna, let me pay you to teach me what you're doing. I want to do it. Makes sense.

And so I transitioned into that. I'm also big on my family, big on faith. Love traveling and like documenting all these things. So I struggle with his conversation of like build a personal brand also having the business in my content because I'm like, I want to talk about, like we do flips and we do so many fun things with like our life and our kids and homeschooling and all this stuff.

And then it's like, and also I have this business to run that requires like a lot of my time and content on that same page. Anyway, all this to be said. You do mix. I do mix it in very much.

I know that's why a lot of people find me because of course people are late to me on other things. Of course. But the part that I'm struggling with the most is one year ago today at the top of my career making hundreds of thousands of dollars a month, I step away. I shut the whole thing down overnight.

Why? Burnout. Makes sense. And it was...

Why did that happen? Because I didn't hire leverage. It's because I did it myself. Isn't that awesome?

The fact that you can answer the question. Is that bad or good? No, it's so good. It's so good.

It's so good. It's so good. It's like, I'm telling you a lot of people Johnny, let's go eat dinner. We're gonna go eat dinner.

And this motherfucker spent eight hours building this immaculate thing and he would just look at it and be like, pshh, and run and smile. And I'm like, that's me. I just want to see how big I can build it. And then I actually don't give a fuck about it.

I'm very detached from my career. I'm fully detached. I could give a fuck about Gary Vee. - How did you get to the place where it doesn't define you?

Because I feel like I'm still struggling with like so much of... Like I'm still trying to figure out... - None of it defies me, because I have my definition somewhere else. My definition is if people think I'm a good guy.

- Was it always the case? - Yeah, in hindsight. I didn't know it was always the case. - Have you ever worried?

- About what? Anything? - Yeah, I worry about everything. - I worry about nothing besides health.

Because I'm not in control. Got it? I'm in full fucking control. - Do you think God is in control?

- Yeah, to some degree I do. God, I believe in God. So yeah, destiny. I believe in serendipity.

I believe in like shit happens. Like, I'm not sure God's like sitting up there like, I'm going to put a chicken bone in that throat and they're gonna die. I'm not sure that's how God is cooking. So I believe in enough things that know that I'm not in control.

But everything else, we're all in control. And this is what I want for you badly. Now I'm starting to understand you a little bit with that sentence. When you can tune them all out.

My greatest skill set by far is humility. It's not obvious, but like, and it's easy. You know, it's funny when you think I'm humble, right? But like, I know it because I don't hear all of you when you say I'm the best.

Which allows me to not hear you when you say I'm the worst. I can't hear it. I'm in the arena. I'm in the arena.

You're the stands. We're all in the stands for each other. You're all in your arena and we're all the fans. And we're like, you can't score.

You're good. We should trade you to another team. We're the fans. You're the only one in the arena.

I'm in the fucking arena. I can't take your judgments, your praise, or your shitting on me to the field. I got to play the game. The second you detach from that, everything changes.

You have nothing to prove to no one. Most of all, not yourself. Yeah. My stand journey actually goes back about three years or so.

I basically help couples ditch the hug and waddle and learn how to slow dance. That's incredible. That is what I do. That's so good.

Thank you. Good for you. Okay. And I started with stand to I was so grateful.

And I found it because I was teaching in person. I've been teaching ballroom dancing since I was 16. And then I got this idea that I wanted to bring about a slow dancing revolution because I was starting to learn all the benefits of learning how to dance. And I was just seeing what it was doing for these couples in front of me.

And so I loved that stand paired with social media gave me the opportunity to slow dancing revolution. So I've had over slow dancing one-on-one date night course. And there are a couple of other ones, but then I also choreographed for stances for people that, yeah, which is really, really fun. And so now over 8,000 people have ditched the hug and waddle through the slow dancing one-on-one.

So it's all digital products or there is some virtual components. There's a little bit of virtual when it comes to the first dance choreography, but not on like the date night courses. It's all filmed. Everything's broken down.

You can cast it to their TV, have a little date night in the living room kind of thing. So I'm, I am looking to expand. I'm going to do like a six month container. You were talking about implementation of like helping couples actually just work on intimacy and play.

Yeah. Cause that's the first product. Like you're doing something very important. And I think there's some real building blocks.

Yes, for sure. That gets into like the value of salvaging of marriage is very high emotionally and for some people financially real talk though. Like there's a lot of people who are in a marriage that they're struggling with and the only reason they're staying in it is financially. So they would love the opportunity, especially a lot of people, the more money that's being made is actually the more they're staying in it, which means they could pay a lot of money for someone that could actually unlock certain parts of the marriage.

Like my glute me, literally, by the way, I'm just very fascinated by this. It is literally not functioned for 30 years of my life. My brain has made every, like literally my, I don't know John, I'm very into this. My QL, my QL and my adductor have done all the work for what everyone else here has their meet for.

It's literally not connected. That is happening in marriages. There's, and you can, why I'm using that analogy, they can't see it. And you're doing a little, a moose boosh with what you're doing.

I think you could have something that's 30,000 a month for a person there. I'm telling you, I'm around a lot of wealthy people. There are people that would pay $90,000 for three months to get a lot of access to you if they went through the whole funnel, right? Right?

Like that's because it's worth it for them. Like again, either through like the way they put marriage on a pedestal emotionally or just very practical, like I don't want to get a divorce. Cause I'm gonna lose half my wealth. Like real shit.

If there's something very there. Anyway, nonetheless, I'm grateful. No, it's very validating because just a tiny bit more about my story before the question with it is I was a very young entrepreneur. Like I started my company when I was 18 and then I went through a startup incubator at Georgia tech.

I have a different startup that I work on. That's building on a platform to connect in-person instructors with people. Okay. But it was interesting because like my first relationship was a three-year relationship.

I thought it was my person fell apart horribly and very publicly. I have over a million followers across all platforms. And it was like a huge, oh my gosh, I'm a fraud. Like I'm, right, right, right.

I'm teaching you. Right, right, right. And so it was interesting because I was lucky enough a couple of years later to meet my now amazing husband who dances with me and really helps with the business, which is phenomenal. And so now, you know, that was the biggest mistake to say, I realized that was the biggest decision I was gonna make in my life too.

Am I waking up with every morning person is this. And so I'm really excited to build out that container. Well, as I'm doing that, I am expanding my team and I'm finding like, I'm a pretty tight B entrepreneur. I'm also a vampire.

I like to operate on night shifts. That's when my best work is done, but it doesn't really work with building out a team. So what are some, oh really? Okay.

I would love to like hear how I can be there for my team. If I'm a bat, hire vampires. Okay. Yeah.

Yeah. I'm not that person, but I will never ding Sid for something that's based on me being that person that he had to adjust to that. Thus running something else to fall. That started with me being that person.

So as long as I don't have the hypocrisy and the loss of trust by being like, Hey man. And he's like, fuck you, bro. You changed it at 1259. And I felt like, of course, the thing, like you got it.

Like, don't make up bullshit out of your own insecurity that you're that person. Got it? Okay. That's it.

I don't know if you guys know this. There are 8.3 billion people on earth. Like we do this. We do this.

By the way, everything is maybe the worst thing that is stopping all of you is the default to no. The worst. Everything is maybe. And if you get really epic, because I think I'm epic at this game, it's maybe with a desperate want for it to be yes.

I've actually had to get better at maybe and no, because I'm just a fucking fat kid with cake. You know, I just want to do every business, you know, like, like hire night owls. Okay. Yeah.

That makes a lot of sense. In fact, you'll get some really cool people, right? Like night owls will allow you to get a stay at home dad that like would have never been able to get a different type. Like, like, you know what I mean?

Like, like you're just gonna get different types of people. Yeah, for sure. And in terms of kind of showing up for them, like if I'm pretty type B and I'm like all over the place, what is the best way, like a baseline skill I need to have to be a good leader to be empathetic that you're that person. Yep.

I'm that person, but I will never ding Sid for something that's based on me being that person that he had to adjust to that. Thus running something else to fall. That started with me being that person. So as long as I don't have the hypocrisy and the loss of trust by being like, Hey man.

And he's like, fuck you, bro. You changed it at 1259. I do not... This is the gold rush of attention.

It is not guaranteed. It had never existed before where normal people like us had access to the entire world for zero dollars except the effort it took us to make content. It had never happened before. Advertising was expensive, and Hollywood decided if you were on TV and there was only three channels, then 13, then 36, then a little bit more.

This is not guaranteed. So if I'm right, how hard do you think you should go the next five to seven years to build your business? You're a person. Very hard.

The end. Right. Real talk. It's coming.

And I don't know. I don't know what it's going to be. Will the social apps be in there and we're just scrolling through? I don't know.

I have a funny feeling it won't be exactly the same. Yeah. I mean, so that's it. I gotta run.

I apologize. Thank you, everyone. Thank you. Great to see you all.

Hey, everybody, if you enjoyed this podcast, please go back and look at the prior episodes. They're loaded. I appreciate your attention and thanks for being part of this journey. See you later.

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How long is this episode of The GaryVee Audio Experience?

This episode is 46 minutes long.

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This episode was published on February 9, 2026.

What is this episode about?

 In this episode, I reveal why the greatest skill to have as a CEO is humility. I share my philosophy on authenticity, explaining that being your "full self" is the only path to true originality. I coach several successful entrepreneurs who are...

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