Why Humility is the #1 Skill a CEO Can Have

9 Feb 2026 · 46 min · 27 chapters

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In short

Podcast Summary: The GaryVee Audio Experience

Episode Title

Why Humility is the #1 Skill a CEO Can Have

Overview In this episode, Gary Vaynerchuk discusses the vital role of humility for CEOs, presenting it as the greatest skill one can possess. He emphasizes authenticity, sharing his personal experiences and philosophies, especially relating to the balance between community-focused ventures and larger brand monetization strategies. Additionally, he provides insights into succeeding on platforms like TikTok Live and encourages listeners to embrace their unique selves.

Key Learnings

  1. The True Meaning of Authenticity
  2. Authenticity involves being your "full self."
  3. Originality stems from genuine self-expression.
  1. Mastering TikTok Live
  2. TikTok Live operates by continuously presenting your content to viewers, unlike other platforms.
  3. Engagement is crucial; adapting your approach can yield better results.
  1. Monetization Strategies: Boulders vs. Pebbles
  2. Boulders: Focus on large brands and significant deals.
  3. Pebbles: Community-driven products or services.
  4. The current market might favor community products for growth and connection.
  1. Importance of Humility
  2. Enables a CEO to remain grounded and not overly swayed by both praise and criticism.
  3. Helps maintain a focus on self-improvement rather than public perception.
  1. Leveraging Scale
  2. Finding the right balance between personal involvement and delegation is crucial for growth.
  3. Investing in relationships and community can lead to expansion and opportunities.

Discussion Highlights

  • Building Sandcastles: Gary shares a metaphor about watching children build sandcastles, paralleling his enjoyment in building businesses without attachment to the outcome.
  • Coaching and Consulting: Gary advises on maintaining hands-on experiences while operating at scale, suggesting options like creating thematic content that keeps the essence of real experiences without disclosing identities.
  • Social Media Engagement: He recounts his own return to social media after a long break and the transformation in his content strategy to meet market demand.
  • Importance of Personal Connection: He stresses that personal connections in business can lead to greater opportunities and community strength.

Personal Stories and Insights

  • Gary shares anecdotes about his teaching background and evolving business strategies.
  • He reflects on the importance of humility in both personal and professional life.
  • Throughout the episode, he engages with listeners, providing real-time advice and fostering a collaborative environment.

Conclusion The episode encapsulates the essence of humility as a foundational skill for leadership, coupled with actionable advice on branding, community engagement, and the evolving landscape of social media. Gary encourages listeners to embrace their authentic selves and pursue their unique paths without fear of judgment.

Call to Action Listeners are encouraged to reflect on their own humility within their professional journeys, consider their monetization strategies, and actively engage with their communities to foster growth.

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*For more insights and discussions, tune into The GaryVee Audio Experience and follow the podcast for updates.*

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Chapters

Tap a time to open that second in VO

Building Immaculate Sandcastles

0:38 to 2:48

Gary discusses the metaphor of building sandcastles as a reflection of ambition and self-definition.

“So my question for you is I'm also a teacher and a parent and I just gave my 30-day notice for my teaching job.”

The Importance of Hands-On Experience

2:48 to 5:26

A dialogue about the value of hands-on experience in teaching and coaching.

“You can just go get a job in Kansas City.”

Navigating Business Opportunities

5:26 to 8:16

Gary gives advice on how to capitalize on business opportunities while maintaining authenticity.

“So we launched a$99 guide and in the stand challenge we made 145K.”

The Shift to Social Media

8:16 to 11:03

Discussion on the transition to social media and opportunities in mobile editing.

“So like I haven't gone live in 100 years and then I was doing a final push.”

Building a Personal Brand

11:03 to 13:40

A conversation about personal branding and the challenges of standing out in a crowded space.

“That's very important because whether, you know, I know for sure my personality is my whole life.”

Navigating Content Strategy

14:01 to 14:42

Learn the importance of balancing value and sales in content creation.

“Do you think that that's still a smart move?”

Sophie’s Journey with Endometriosis

14:43 to 16:49

Discover Sophie’s inspiring journey from illness to building a health brand.

“I was like, no, no, you have to give, give value.”

Building a Women’s Health Brand

16:50 to 17:48

Explore the creation of Found and its mission in women’s health.

“I've started a women's health brand called Found.”

Hiring Strategies and Growth

17:49 to 19:49

Understand the importance of strategic hiring and delegation in business.

“Because that's something I've been thinking about.”

Scaling a Real Estate Business

19:50 to 21:08

Learn how to leverage social media for scaling a real estate business.

“And so they looked at me and was like, what are you doing?”
Show all 27 chapters

Dealing with Burnout

21:09 to 22:46

Discuss the challenges of burnout and the importance of hiring help.

“understand if you keep tuning it allows you to do that.”

Investing Back into Business

22:47 to 25:06

Explore the principles of reinvesting profits for long-term success.

“The fact that you can answer the question?”

The Drive for Curiosity and Growth

25:07 to 28:00

Understand the intrinsic motivation behind building an empire in business.

“like we know what the financial, like I know the financial journey I went through, but I was like, man, it felt like we were way more poor than we should have been.”

Curiosity and Personal Growth

28:00 to 29:08

Explore the importance of curiosity in personal and professional development.

“I'm wildly curious how big I can make it.”

Building Impressive Sandcastles

29:08 to 30:25

Gary shares an analogy about building sandcastles to illustrate detachment from success.

“like when I vacation I want to be off the grid, do nothing, nothing, because I go so hard.”

Control and Faith

30:25 to 31:18

Discussing the balance of control over one's life and the role of faith.

“Because I feel like I'm still struggling with so much of, I'm still trying to figure out who I am.”

The Power of Humility in Leadership

31:18 to 32:26

Understanding how humility allows leaders to detach from external judgments.

“I don't think that's how God is cooking.”

The Value of Building Relationships

32:26 to 33:40

Exploring the importance of relationships and intimacy in partnerships.

“The second you detach from that, everything changes.”

Challenges in Marriage and Business

33:40 to 34:46

Discussing the intersecting challenges of marriage and entrepreneurship.

“It's all filmed, everything's broken down, they can cast it to their TV, have a little date night in the living room kind of thing.”

Navigating Entrepreneurial Decisions

34:46 to 35:51

Gary reflects on his entrepreneurial journey and the importance of partnership.

“My brain has made every, like literally, I don't know, John, I'm very into this.”

Building and Leading a Team

35:51 to 37:03

Insights on how to effectively build and lead a team as an entrepreneur.

“because just a tiny bit more about my story before the question with it is I was a very young entrepreneur.”

The Importance of Empathy in Leadership

37:03 to 38:01

Discussing the significance of empathy for effective leadership.

“I need to find my crew like Jenna does, yeah.”

Understanding Effective Coaching

38:01 to 40:59

Examining the relationship between being a practitioner and a coach.

“In fact, you'll get some really cool people, right?”

Long-Term Brand Building Strategies

40:59 to 42:00

Gary shares principles for building a lasting brand in business.

“In order and then you know yourself, you're hiring your complement, right?”

Embracing Authenticity and Growth

42:00 to 43:06

Learn how authenticity and self-acceptance contribute to personal growth.

“that come very easy, top of mind with that question.”

The Importance of Content Volume

43:06 to 44:18

Discover why focusing on content volume is crucial for social media success.

“That being said, to continue the viral trend, would the advice that you gave me for my question be the one that you think should be the payoff for the video?”

The Future of Social Media and Content Creation

44:18 to 45:48

Understand the evolving landscape of social media and its implications for creators.

“There's awareness being known and social networks are free.”
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Transcript

Automatic transcript. May contain errors.

0:00There's a thing I want to paint to you. It's my favorite one. I would watch a kid, 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, like dinner. Like we're gonna go eat dinner. Spent eight hours building this immaculate thing. He would just look at it and be like, 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 of it defines me.

0:29because I have my definition somewhere else. My definition is if people think I'm a good guy. This is the Gary Vee Audio Experience. So my question for you is I'm 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? Essentially, yes. Yeah, 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 and I love getting my hands in there. And I do one-to-one consulting as well and I coach people with kid videos but I'm worried about getting that hands-on experience still to keep myself fresh and also potentially use as content but then it's other people's children and so how that would work.

1:14Well, 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 with 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. You could even say there was a child. I do that now, but I mean like working with a parent physically, 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 or two people or 10 people just so you can taste it.

1:58It could be content for you and it's a good give back. Or it could be a business. 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, somebody, 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'm always 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 it.

2:40They'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 a summer camp business. I don't fucking know. You can do anything. Like an in-person summer camp. 100%, you might love that.

3:14Yes. You like that one, right? I do a lot, yes. Isn't that good? Yes, I do. I like it. You like that? Give me some, that was a good one. Yeah. I appreciate it, thank you. You're welcome. Yeah, I mean, that's why I used that college analogy. You're golden. I get why you value, by the way, I value it. It's why my agency crushes because of Gary Vee. 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.

3:47It'll make my mom super happy. Yeah, for me, I had deleted 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 thought, I just knew I had to do it. I don't know why. You just sensed it? I just sensed it. 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 relate anymore. Like I was missing out literally. Yeah, by the way, that's my big argument to like where the world, like everybody trying to protect their kids from technology.

4:22I'm like by the time these five-year-olds are 18, we're gonna be in VR and AR glasses. Like technology's coming in deeper, not like, but nonetheless, go ahead. Yeah, and I had an agency in Switzerland doing website designs, branding, so I kind of had to. I got it, got it. You're from a business standpoint, now I understand. Yes, and just my husband and I, we had it together and he was absolutely against social media just for himself. So I had to do it. And I did it and I saw that there was a big opportunity for mobile editing. mobile editing yeah because um people just love the way that i edit up my videos yes um and i sense that it was was a market for it yes um and people were actually commenting under every single video not about the content of the video but they added it they added that's okay there's a market for it um then i started a page called mobile editing club where i wanted to teach that yep and then the whole ai wave came yes like okay wait a second let me just try that yes i did try it and it just blew up.

5:18I had like 12 or 15 ,000 comments underneath it and I was like, okay, I think there's opportunity there. Yes. And all of them wanted to like know how I did it. Yep. So we launched a$99 guide and in the stand challenge we made 145K. So we were top of the year. So that was really cool. And now we've even crossed six figures a month. Wow. A month. A month, yeah. And now we're at a point. John got excited. And you were first too. Yeah, yeah, yeah.

5:53Go ahead. But at the same time, we got more than 1 ,000 project inquiries that we could not handle because at the moment it was just like my husband and I. And we were like now at the point where we have project requests from like big brands that could bring a lot of credibility. at the same time we have the opportunity to launch more projects sorry more yeah more products I would I understand by the way as you can imagine I've lived a chapter of that I think you just have to I obviously decided I'm going to monetize the boulders at VaynerX versus the pebbles of my community I don't think there's a right or wrong I think everyone just has to play their game you know I have monetized the pebbles through books or collectibles or wine.

6:43So I got to a place where I did both. You will, if this keeps going and you keep doing a good job, you will do both. My intuition is, you may know this because you had an agency, I want you to build more leverage with the pebbles for a little bit longer. The boulders are always there. Does that make sense? Yeah, it's like time sensitive at the moment. Correct. Everybody wants to learn it. You can always go to the boulders. Does that make sense? Yeah, absolutely. So in this exact moment with very little details, but enough to make me, usually you can hear, I'm like optionality, you can go hard.

7:18I like optionality. I don't think, back to parenting, right? I don't think they're, you know? But I will say in this one, I think tripling down on the little pebbles, because your profile will get bigger. Yeah. Right? We're just an instant run right now. Correct. There's all the others. And you'll just, my intuition is that the pebbles are the right way to go. But if you're in the mood to take one big client, because you and your husband want to. Again, it's not a binary black and white, but my intuition is more pebbles. Okay, and then there's like life events. People want to have life events.

7:49Makes sense. So it's kind of like, Yeah, look, I mean, look, I would argue my biggest challenge professionally is that I'm crippled by opportunity. And I'm crippled by real opportunity. You know, I would say that you make choices. You know, and then you live with them. As long as you're good at making choices that in hindsight were mistakes, as long as you can be that strong, then you're golden. Yeah. Okay. All right? Amazing. Thank you so much. You're welcome. Of course. Thank you. Congrats. The TikTok live question. So like I haven't gone live in 100 years and then I was doing a final push. And I'm glad you said that.

8:30Like some of you have probably tried live. Like live wasn't good for a long time. Yeah. Instagram live, you go on, they ping your followers and then and your number, whatever your number is, 100, and then a second later it's 12. I'm 1 ,000 and then it's like 150. TikTok's the reverse. It just keeps giving you people that don't know you. It just keeps, what else do we want? Is it quality? Ish. Is the algorithm - Ish, ish. You heard her. People's sale to me is a micro commitment, so why not put them into a group where they - Ish. No, I'm sold on that. I'm just saying, is their algorithm like YouTube's is so good at fighting the right person?

9:05Ish. Ish. But it's a real fire, but it's good. People are interested, they'll just swipe by for like a millisecond and then they stop. They're like, oh, you said the right word at the right second that they stop. Yeah, it's a whole science. It's QVC. The reason they used to pull people after one show is like, you didn't sell enough. But here you don't get kicked off. You just keep refining. Come. So my question is pretty much pertaining to in a space where people are just obsessed with education. I coach UGC creators to build personal brands to attract brand deals. And there's a lot of information out there.

9:35and everyone's obsessed with education. If any of them want jobs, you should, like I'm being dead serious, you should talk to Sid. Like we are just constantly hiring people here often with just enough UGC experience that we can teach them. I literally have a community of over 200 people and a mentorship for the 150 and they would love that. Connect. Like this for all of you to know. Let's do it. We're just hiring constantly. A lot of people like know pretty quickly they're like, okay, I can really do this by myself or this is awesome, I'm good but I need to go work somewhere for a couple years to get better.

10:03Like we're that place. Yes. Anyway. My community is called Six Figures After Five and I built it because I built my business in the end of five. But then I eventually changed the meaning when I quit my job which was only six months ago. Or seven, eight months ago now. And I changed the meaning to pretty much anyone, a parent, a student or whatever. Even a five year old. There you go, even a five year old. I'm good at commercials. From that logic, I want to know, I try to give different value. and this competition just forced me to just be myself. I'm like, if I'm aggressive, too aggressive for you, then I'm not your person, but if I'm aggressive, then I'm not.

10:40How many people here, when they first came across me, I'd like to think you like me now, but first came across me, did not love it. Oh, I was obsessed with you. Yeah, there you go. If you say the delivery. Yeah, by the way, you'll appreciate this. Whether it's the delivery, whether it's a word, whether it was the cursing, whether I was a white dude, like everything's allowed. It's a very binary question. Some of my best friends are white. I got it. But you know what I mean, right? That's very important. That's very important because whether, you know, I know for sure my personality is my whole life.

11:13I've moved multiple times. It is full obsession or full fuck you. But I am who I am. The fuck you, especially like when I moved to schools or if you knew me, like give me three hours. The fuck you goes, wait a minute. You know, like because I am who I am. Online, I don't get that luxury. so that fuck you can stay for a while until I pop up in the algorithm with the right piece of content or when someone that you trust really knows and you're like, are you crazy? Do you know this? And then it's like, oh, wait a minute. So you need to be you all the way. Oh, so yeah, I am now. I know. More or less.

11:45More. But that. So even more. No, no, that. Yes. Whatever is, honestly, I mean it. Whatever is still left, know that that's the thing that has the most upside. By the way, I apologize because I'm just helping everyone. Go look at the first 80 episodes of Wine Library TV. I was so scared that all the people that were buying hundreds of thousands of dollars of wine from me at the time would watch one of these videos and see that I was silly. So the first 80 of Wine, literally you gotta go look at this on YouTube. The first 80 episodes of Wine Library TV, I'm chill. I'm like very straight. And then like out of nowhere, like episode 84, it's who you know.

12:25And literally the second I did that first episode of Who You Know was the rest of my life. And by the way, what you saw from 180 was me. Just, I was, you know, just had my foot, you know? And like, you clearly put more on, and I'm just saying, whatever's left. And that's what I do on the lives, honestly, more or less. And sounds like the lives are going well for you. So weird. So that's my other question, or my question, but literally in a space where there's so much education available how and people are talking about the same topics over and over again. They want to hear it from you. Well, they're collecting education.

13:04How do you get them to actually. By yelling at them more. So, okay, so I just have to keep doing what I'm doing. Correct. Yes, because I didn't know it was going to be the sixth one for her when I went. Yeah. Love, Raz, joke, passive aggressive, direct to their face like you fucking suck. Like give up on them, make them come back. When you're obsessed like I am, to get people there, you're not in control. You're only in control of your effort and your ability to have different moves. Yeah. So I'll just keep it pushing then. I've been pushing for 20 years. No, that makes complete sense. My key for you is all the way.

13:44Because I think there's a little bit left and I think it's the real thing. Give that some thought. I will, I have one little tidbit. So right now, I push a lot of testimonial type of content because my students are like talking and whatnot. Yeah, of course. Do you think that that's still a smart move? Will people get exhausted? People will get exhausted and I think people over time, if you go just, if you're too much of that content, it's just... Oh, it's not. It's just like once in a while. Oh, then you're golden. I would say it's like food. Everything's good a little bit. You know? If you were 90, 80, 70 % testimonial, it would feel too salesy, but a little sprinkle of the testimonial, it's pretty good.

14:29Really good value. Can you put like a little bit like testimonial? Yeah, yeah, yeah, yeah. I would say that's why I wrote Jab, Jab, Jab, Right Hook. Jab, Jab, Jab, Right Hook started writing for all of you in the world that were just selling in every post. I was like, no, no, you have to give, give value. You know who ended up helping the most? The people that were scared to throw the right hook. The people that thought selling was yucky. That's who it ended up helping the most. So yes, you should. Hi. Hi, nice to meet you. I'm Sophie. Hi. How are you? Thank you. How are you? Good, good. So my kind of stand journey is pretty, well, I say new, it's been like a year and a half, two years now.

15:06But I have something called endometriosis. It's a condition that, yeah, 10 % of women have it. It's crazy. And I was like bed bound 50 % of the month. It was awful. Wow. And so I had like all of these great jobs with Procter & Gamble and Amazon. So I was super capable. but like the pain was just horrendous 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 kind of 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 vlogging it so to your point earlier about like documentation I didn't have a business I was just vlogging 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 was like in the gym on a stay master being like how do I sell digital products because I don't understand technology at all yeah and then Coco Mocha a TikTOPian youtuber made a video about Stan it was like people sell them on there so I did it and I went from making like a thousand pounds a month to the point where I was like gonna have to go back to my old job and we made a hundred thousand in our first month just from auto DMs on 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, I'm like, John, SOS.

16:20And again, like you were saying with Gary, like text me back every single time. And then because of all of those sales, I was able to publish this book. Amazing. Which I would love to give to you. Thank you. So it's called the Anti-Inflammatory 30 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 it. Yes, loves. She will love that. Yes. But my whole thing now is like, I'm so lucky and grateful that I've found the answers for myself. And I want to help other people find those too.

16:50I've 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, you come to Found. Yep. So we have. Like the not was for weddings. Yes. Got it. Exactly. Okay. Understood. Keep going. 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 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.

17:30What would be your key hires? What don't you like to do? Yeah, all of the operations. I remember we were talking about this when you were in London. I love the creative. I love the talking. You need a COO. 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.

18:08I want to give you equity. Sally and Johnny are like, what the fuck? You're the best. because they just signed up for a job. No, I would not do a co-founder. Okay, so CEO first. Okay, interesting. If you're pop committed to the content and you're pop committed to the content everywhere, everywhere, then the next thing in parallel is the hiring because you're starting to hit scale 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 if you're a woman trying to help women, this is the best time.

18:46My ultimate goal is that we have clinics that people can come to and retreats to have transformational experiences. Well, the good news is you know this is coming. Yeah. Right? The education's getting up. I know it because Mona's 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, there's significant investment that you need into it. I want you to keep growing your top line revenue in your business so that you have more leverage when you decide to raise capital. Got it? What's that? I said 100%.

19:23Everybody 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 gonna 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?

19:55Sure, of course 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. Tell me what you're doing. I need to know and so I started One-to-one launch my course on Stan. This is like two 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. How much? So that course started out at like$2 ,500. And then I've just raised my prices since. Again, I just want to, there's certain people here that need to hear what I'm about to say.

20:29In real estate, there's a saying. It takes as much effort to sell a$25 million home as it does a million dollar 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.

21:07like 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. Go ahead. So true. Yeah like for the stand 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 is 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 transition into that i'm also big on my family big on faith love traveling and like documenting and all these things so i struggle with his conversation of like build the personal brand also having the business in my content because i'm 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.

22:18Anyway all this to be said. You do mix. I do mix it in very much so and I know that's why a lot of people find me because they relate to me on something else 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. You just cracked. Complete burnout. Makes sense. And it was. Why did that happen? Because I didn't hire leverage. Yes. 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.

22:51It's so good. It's so good. It's so good. It's like, it's, I'm telling you, a lot of people, like one of the, actually, I don't give my dad enough flowers for this. My dad, there was always things in my me and my siblings of like dad loves the liquor store more than us dad loved the liquor store more than he loved himself I grew up watching someone putting everything back into the business so it just became my culture I mean I ran this company Vayner got it this is where it's cause a lot of us that come into it are like ooh now I got the money now let's go buy a new bouncy for the kids and a new car and employees Yes.

23:35We did that, but we invested it in real estate opportunities. Makes sense. But not the business. Correct. And so I burned out on that. Makes so much sense. But now I have something to show for the money because we invested all of it. That's good. And so that's great. But now it's like, yeah, now I'm restarting. And I, well, I relaunched everything in the spring of this last year. And so slow. I'm like, I can speak to any person who's relaunching and selling and not getting anything. And I'm like, you just, it just takes time. Now I have a flourishing business again. We've been hitting a couple of six figure months again.

24:09And I'm like, so. You're on the cusp of being back. Yeah, cusp of being back. But like something feels off. Yes. You're, you're doing the same pattern. I know. And I did, I did bring someone in. I did finally bring someone in. But it might not be right. I know. I know. I know. No, I know that's the answer. Of course it's the answer. You hit it though. That'd be like me saying to everyone, you have to make a pasta dish. You're like, okay, I gotta make a pasta dish. But if it doesn't taste good, like we defeated the, you have to make a delicious pasta dish. You have to hire the right employees. Yeah.

24:44And you have to learn how to become a better boss. Yep. Yeah. Yeah. And who you, how you're raised plays such a big role in this. You don't say. My parents were tightwads and like, you pull the money in. Of course. Right. Notice how I even preempted that by saying my dad loved the store more than him and gave the money all to the store. We always are like, man, you know, like we know what the financial, like I know the financial journey I went through, but I was like, man, it felt like we were way more poor than we should have been. And I was like, oh, right. My dad actually didn't take any money.

25:21It was all going back to business. And right, my mom is very cheap. and never bought us anything. Like that's it. You know, like that was our life. You know? Is there, this is maybe a more practical question, but is there like a percentage that you look at? Like, oh, if your business is making 500 ,000 or a million, like you should spend this much on, what is it? As much as humanly possible. Okay. Based on who I am, I'm trying to build an empire. Okay. You may not want to build an empire. Thus meaning you can take more for you to buy an umbrella or a Big Mac or another car. but the answer is the answer I gave you.

Read the full transcript

25:56Jenna, right now you're running like a 95 % profit margin business. I know. So you get this. And I don't have a mortgage anymore. My expenses are lower. It depends on the growth level. Let's say anywhere between 10 to 30 % profit margins. So that's as large at scale as this, like billions of dollars. You guys have to recognize the difference between y 'all's profit margins. You can afford to spend 5, 10 % of your... You'll love this. Do you know who hates me most in this entire building? I'll walk you over. He's over there. he's the CFO the chief financial officer do you spend too much money or why does he I'm just yes but not on dumb shit like hey Sid go take everybody out and eat dinner in fact I'm too tight on that it's on more people more investment in the company like because we're going to live next year and I want to live next year back to what I said to you earlier when I had a bad year over invested against we were slow now I have a little bit of understanding of how that happened and why and like the more you put back in and you know what you're gonna love?

26:53I can already tell, you're emotional. Like me. I'm emotional. I'm very emotional. You're gonna love having the right employees. I love Sid crazy stupid. I love Sid. It's really, really real. You're gonna love it. Once you get your crew, you're gonna have a family business. You're gonna have three new best friends. The only friends I have are people that work for me. They're the only friends I have. I hired my students. You're going to love this. You're now judging it based on what happened. It's the wrong hire right now. But when you get the right to, I can see it already. I can see it. I'm good at this.

27:33You're going to have four employees. It's going to be a fucking sisterhood. You guys are going to fucking cook. I can't wait. Thank you so much. You're welcome.

27:45You're going to love it. I'm telling you, you're going to love it. It's going to be your social circle. Yeah. You said you want to build an empire. Yes. What is the why behind that? Can I just ask because - I got a real, I actually figured, ready? I actually have my answer. I'm wildly curious. I'm wildly curious how big I can make it. Nothing else. Straight curiosity. I'm just wondering. It's like, you know, it's so funny. Back to health and wellness, never interested in how far I can run, how much I can lift. And I look at it and other people, I'm like, that's crazy, that's stupid. But in this, it's the only thing I'm interested in.

28:24In terms of scaling? Yeah, just curious how good I am at the game. Because I know the results are the truth. Like, if I don't get it to where I think I can get it, I wasn't good enough. That's sick. Yeah, I think so too. I think so. Like, when I finally had my, because I've thought about it for a while, I'm like, is this, you know, because for a while, I'm like, is this insecurity? Like truly, everyone's in your own field and I knew it wasn't because of everything you kind of know about me. I'm like, is it delusional self-esteem? That was a big thesis for a little while. I'm like, no, this is my fucking game.

28:59Honestly, when the Kobe story started to come out about how the day after surgery just desperately wanted to be in the gym and start practicing, I'm like, I get you. And then I've got another analogy. I really, it's my favorite one. I like beach vacations. like when I vacation I want to be off the grid, do nothing, nothing, because I go so hard. I started going on those nicer vacations at a point in my life and there's this thing I want to paint to you. Yeah, I'll be able to get this on. There's a thing I want to paint to you. I would watch a kid, like cliche, Turks and Caicos. I would just lay on the beach from 9 a.m.

29:40to 7 p.m., right? And just listen to music and think and draw in the sand and that's how I liked it. but once in a while there'd be a kid or two kids and they would build an immaculate sandcastle all day and then about 5.30, 5.45, like this is just, I saw this, this happened like two or three times and it finally clicked for me. Like the parents would call, they'd be like, Johnny, let's go, like dinner, like 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, 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.

30:18I'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 so much of, I'm still trying to figure out who I am. None of it defines me. Because I have my definition somewhere else. Because it's a game like you said, right? My definition is if people think I'm a good guy. Was that 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.

30:56Because I'm not in control. Got it? I'm in full fucking control. Do you believe God is in control? Yeah, to some degree I do. God, I believe in God. Yeah, destiny. I believe in serendipity. I believe in shit happens. like I'm not sure God's like sitting up there like I'm gonna put a chicken bone in that throat and they're gonna die. I'm not sure like that's how God, I don't think 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 with that sentence.

31:34When you can tune them all out. my greatest skill set by far is humility it's not obvious but like i and it and it's easy for you know it's funny thing to say 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 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.

32:18I can't take your judgments, your praise, or your shitting on me to the field. I gotta play the game. The second you detach from that, everything changes. You know? You have nothing to prove to no one. Most of all, not yourself.

32:41Yeah. 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. Yeah. That is what I do. That's so good. Thank you. Good for you, okay. Yeah, and I started with stand too. I was so grateful when 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 Stan you know paired with social media gave me the opportunity to 100 % revolution so I've had what do you sell so slow dancing one-on-one date night course and there are a couple of other ones but then I also choreographed first dances for people that yeah which is really really fun and so now over 8 ,000 people have ditched the the Hug and Waddle through the Slow Dancing 101.

33:35So 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, they can cast it to their TV, have a little date night in the living room kind of thing. So I am looking to expand, I'm gonna do like a six month container, you were talking about implementation of like helping couples actually just work on intimacy and play in the relationship. You just took, like, because that's the first proc. You're doing something very important. And I think there's some real building blocks.

34:07Yes, 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 their marriage. Like my glute med, literally, by the way, I'm just very fascinated by this.

34:44It has literally not functioned for 30 years of my life. My brain has made every, like literally, I don't know, John, I'm very into this. My QL and my ad doctor have done all the work for what everyone else here has their meat for. It's literally not connected. That is happening in marriages. Why I'm using that analogy? They can't see it. And you're doing a little amuse-bouche with what you're doing. I think you could have something that's 30 ,000 a month. For sure. For a person. 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?

35:34Like 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 because I'm going to lose half my wealth like real shit 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.

36:06Okay. 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 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 stake decision. I realized that was the biggest decision I was going to make in my life is who am I waking up with every morning?

36:38Of course. What kind of 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 type B entrepreneur. I'm also a vampire. I like to operate on night shifts. That's when my best work is done. Me too. But that doesn't really work with building out a team. Not true. Not true. Oh really? Okay, I would love to hear how I can be there for my team if I'm a bat. Hire vampires. Okay. Oh, I love that. Yeah. I'm a night owl too. Yeah, yeah. I need to find my crew like Jenna does, yeah. Yeah. Yeah. Higher vampires.

37:22Yeah. That's it. Okay. I don't know if you guys know, there's 8.3 billion people on earth. Yeah. There's other levels. Yeah. 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, and 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. That's it, you know, because I'm just a fucking fat kid with cake. You know, I just want to do every business, you know? Like, hire night owls. Okay, yeah, that makes a lot of sense.

38:05In 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, like, you know what I mean? 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. To yourself or to others? Yep. Both hands, yeah. 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 rendering something else to fall, that started with me being that person.

38:53So 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 12.59. 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, yes. That nailed it for you, right? Yes, absolutely. You're doing certain things where you're a bad boss. You're so young. I mean, I did so many things poorly. I mean, this is where I'm the best. Candor. I've said it a lot that candor as an actual boss continues to be a struggle. Because then it becomes, I'm very good at being passive aggressive with sweetness.

39:29I, in fact, I rebranded it to razzing. First, I didn't even know I was being passive aggressive. Then when I realized it, I'm like, no, let's keep it called razzing because that sounds better. You know, like you go through these journeys. We're all just human. But that's yours. Question is, do you believe that you have to do what it is that you're coaching in order to teach the people that you teach? That's a great fucking question. Let me tell you why. You know where I first think about it? Football. Yeah, yeah. Like, you know, like, some of the best coaches of all time didn't play the sport.

40:01So I'm like, fuck. Because I'm such a, I mean, my whole pride is I'm the fucking best practitioner. And then thus, I only talk about shit I know. So my answer is I do not think that is required, but I think it is really epic when you do do and have gone through and do know. When people talk about parenting and they don't have a child, I'm like, okay. You know what I mean? Like, you know? So that would be my answer. Yeah, because I tell people, like, I'm a coach that still plays the game and I think that they like that. I mean, it's why I'm completely unstoppable. You're in the field. When I'm hiring a COO, what am I looking for?

40:42What are the key things? You know, I think it starts with a list of the things, like you're in a great spot because you're deep. So you can first write down a list of things that you think need to get done way better or at all. And then that becomes the fucking interview process. Got it? It's like what do you know is not happening well or could be done that's not done yet? In order and then you know yourself, you're hiring your complement, right? Right? You're hiring your complement. Like what do you know? And you're further along. That's why I'm confident that's your answer. Because you're a little bit deeper in your business.

41:17It's a little bit more at scale. You know. And by the way, I have three admins and two chiefs of staff. That's clearly someone who knows that organization is the furthest and not interesting. Like think about how much I've quadrupled down on the thing. It's not even one person at the scale I'm at now. Because I'm like, I don't want anything to fall with my time. And it's a lot going on. I need to keep throwing more resources at it. Gary, how do we build our brand for longevity and not hoping to just provide like a hot moment if you're doing very well? And this could very well be our job for a long time.

41:55Yeah, I think, you know, I've had a lot of longevity and it's been based on two principles for sure that come very easy, top of mind with that question. One is the more you just continue to lean into yourself you're not playing a role. You didn't have like a good role that like crushed on TV and then like you got a different role. Right? When you're you, it's you. Two, I think it goes back to something we talked about early which is like just by not judging yourself. Like Gary Vee has had moments when he's been ripping hot and other moments when he's not been as hot and like my ability to be just as uncomfortable in both is gonna matter.

42:30That's why. Not judging yourself. You know, that 2024 year at VaynerX did not cripple me and excited me weirdly. Okay, I got two for you. Dylan keeps trying to... Yeah, Dylan, get it here. No worries. No, the boys are out in this giant... Go ahead. No, I hear you sometimes talk about leveraging certain opportunities for content. Yes. So I wanted to do that today. Okay. I have a very viral format on my YouTube channel. It gets hundreds of thousands of views every time. I reverse engineer what a successful person did to grow on social media. So I almost wanted a permission slip from you. Yes. That's cool to do.

43:02I had it planned. I was gonna do like Gary V reveals how to grow on social media. Yeah. That being said, to continue the viral trend, would the advice that you gave me for my question be the one that you think should be the payoff for the video? Basically volume, focused volume, not just volume, focused volume. Would that be the advice that you think I could end that with? I think you could, yeah, for sure. If I have your permission. Yeah, you could definitely do it. No problem at all. So knowing that I have the three different companies. Yes. Like if I wanted to be undeniable on social, what should I be doing in the next 90 days?

43:34First of all, understanding that it's just like a forever, this is a marathon. So the 90 days in my mind is, there's no payoff on the other side. It's the beginning of doing the fundamentals that will get you there. Look, I believe in volume. I believe in it the most. Anything that can put everyone here in a place to make more content is important. Highly important. Wildly important. The most important. Because it's going to go away. I have really bad news. It's going to go away. Let me explain. This is the only reason this is happening. This is the distribution. This is, that TV, those were the famous people.

44:15You had to go home and watch them. Bill Cosby, Michael Jackson, right? Madonna. There's awareness being known and social networks are free. You know how insane that is? But this is coming. it's actually coming. And I don't know what's gonna happen. Let me give you an example. If Meta wins,

44:43I don't know what they're gonna do. If Apple also was Facebook, would TikTok ever happen? Follow me here. This is coming.

45:03I 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 brand? Your person. Very hard. The end. Right? Real talk. It's coming. And I don't know. I don't know what it's gonna be.

45:53Will 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

From the publisher

 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 Authenticity

  • How to Master the TikTok Live Algorithm

  • The Boulders vs. Pebbles Monetization Strategy

  • Why My Greatest Skill is Humility

  • How to Get the Right Leverage for Scale


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