What Every Entrepreneur Must Hear w/ Gary Vee

17 Sep 2025 · 21 min

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Podcast Episode Summary: The $100M Entrepreneur Podcast with Gary Vaynerchuk

Podcast Overview Title: The $100M Entrepreneur Podcast Host: Brad Sugars, founder of ActionCOACH Description: A platform where business leaders learn strategies for scaling and transforming their companies, featuring insights from global entrepreneurs and business experts.

Episode Details Episode Title: What Every Entrepreneur Must Hear w/ Gary Vee Description: A deep dive conversation with Gary Vaynerchuk focusing on brand, attention, and leadership, especially in the context of AI advancements.

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Key Themes and Discussions

  1. Resilience in Entrepreneurship
  2. Definition of Resilience: For entrepreneurs, resilience is akin to oxygen; it is essential for survival in business.
  3. Importance: Every person in the audience exemplifies resilience by the mere act of being in business, which is a testament to their adaptability.
  1. Building a Brand vs. Competing on Price
  2. Brand Building: Gary emphasizes that establishing a brand is more important than competing solely on price. A strong brand creates loyalty and customer trust.
  3. Social Media as a Growth Lever: Creative use of social media can drive growth with minimal financial investment. Gary suggests producing 20-30 pieces of content daily to build brand awareness effectively.
  1. Adaptability in Business
  2. Adapting to Market Changes: Entrepreneurs must remain adaptable, especially in the face of changes brought by AI and technology. Companies must be proactive rather than reactive.
  3. SEO and AI: Gary discusses the evolving landscape of search and discovery, emphasizing the need for businesses to be top of mind for consumers, particularly in a new AI-driven environment.
  1. Content Creation in the Digital Age
  2. Content Strategy: Producing a high volume of content is necessary to maintain visibility and relevance. Gary mentions that brands should not just rely on personal fame but instead focus on making their business a household name.
  3. Privacy vs. Public Persona: Gary maintains a clear boundary between his personal life and business persona, advocating that entrepreneurs can create successful brands without exposing their personal lives.
  1. Charging What You're Worth
  2. Pricing Strategy: Entrepreneurs are encouraged to ask for more in terms of pricing and not be disheartened by rejections. The market will ultimately dictate value.
  3. Learning Through Experience: Gary shares personal anecdotes on his pricing journey, illustrating the importance of understanding market dynamics and adjusting accordingly.
  1. The Role of Coaching
  2. Value of Coaching: Gary acknowledges the importance of coaching in business, noting that while he never had a business coach, others attribute their success to coaching.
  3. Self-Reflection: Entrepreneurs should be open to feedback and self-improvement, recognizing their blind spots.
  1. Passion for Entrepreneurship
  2. Entrepreneurial Spirit: Gary expresses admiration for entrepreneurs who are driven by passion rather than material success. The journey of entrepreneurship carries its own value and personal fulfillment.
  1. Innovative Projects and Social Responsibility
  2. VeeFriends Initiative: Gary introduces his new project aimed at educating kids about entrepreneurship, emphasizing that not every child should pursue a traditional university education.
  3. Real-World Learning: Highlighting the importance of experiential learning over formal education, he shares how his daughter is gaining valuable skills through real-life opportunities.

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Key Takeaways

  • Resilience and Adaptability: Crucial traits for business owners in a rapidly changing environment.
  • Brand Building Over Pricing: Focus on creating a recognizable brand to foster customer loyalty and retention.
  • Content is King: Regularly producing high-quality content is essential for maintaining a competitive edge.
  • Know Your Worth: Understand the market dynamics when setting prices, and don’t hesitate to adjust based on feedback.
  • Coaching and Self-Improvement: Value of external perspectives in business and the importance of self-awareness for leaders.

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Conclusion This episode of The $100M Entrepreneur Podcast with Gary Vaynerchuk offers invaluable insights for entrepreneurs navigating the complexities of branding, pricing, resilience, and the influence of technology in business. With practical advice and personal anecdotes, Gary encourages business leaders to think strategically and act decisively in their entrepreneurial journeys.

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Transcript

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0:28Everybody in here is looking to build a brand business, the word resilience. How do you see resilience for us as business people and business owners? Well, first of all, thank you for having me at this great conference. I don't know if you noticed, it was very important for me to say what I said up front. I love this audience. I've been in corporate Fortune 500 land for a while. This is my favorite crew because how do I think about resilience for this crew? Like oxygen. That's all they know. The greatest thing about entrepreneurship and owning your business is you have no choice. You have no choice.

1:04If they're here, every single person here is actually delivering on a level of resilience that is not found in society because if they weren't, they'd be out of business and they wouldn't be here. It is my great admiration that I have for all of you because all of you know what I know and I've known it since I was 20 years old. The buck stops with you. if you aren't resilient, if you're not adaptable, this is what I'm talking about. That was my whole talk. The entire talk I just gave is strictly about adaptability. I know that they're about to feel pressure for the optionality of their employees.

1:42So I'm trying to get them to care about their employees a little bit more because that's going to create more retention. I know that the biggest way to grow their business by a country mile with no money is social media creative. But when it comes to resilience, That's my great admiration of this room. That's all they know. Otherwise, they go out of business. So you ended off saying Google AdWords dying. How do we get found on ChatGPT today? How does ChatGPT bring us business? So for the people that are most advanced here, there is ways to do SEO on ChatGPT. And good news, this is why I'm yelling at you for social media.

2:21ChatGPT and whoever else wins, whether they win or somebody else, whoever the Google is or the Facebook is of the AI era, I have good news for you. They're gonna be very happy to take your money. When you type in, I need a plumber, they'll take your money. What I'm more scared about is the companies that are building the best tech, I'm not sure they're gonna be as gracious as Google and wanna give away the business. When someone types in, I'm looking to buy a new home in Bristol, I'm not so sold that chat GPT is going to send you to a real estate agent. I think they're going to send you to their real estate agent.

3:00I think we're going into a very dangerous era of big tech where they're going to be like, fuck the nickels that come along with advertising. We're going to take the whole funnel. Yeah. Google started free chat GPT started with money. You got to sign up. You got to pay right from the beginning. And that's because the tech was so expensive in the processing, but we all know this, all tech starts off expensive and gets cheaper. Remember the cell phones that look like this? They were like$2 ,000 in the 90s, right? Now, you know, they go down and down and down in price. And I think we've seen with, you know, all the deep seek and all that stuff, like there'll be free versions of this.

3:38I'm more worried that we have to build a brand because when I, I don't want to be at the mercy of people like this going to ChatGPT and say, hey, ChatGPT, I've got an entrepreneurial question. Let me ask you this. I want them to be like, hey, ChatGPT, what would Gary Vee think about this? I'm out here trying to build brand. Got it. Got it? Brand. Not, hey, ChatGPT, hey, Alexa, send me a pizza. No, no, no. Hey, Alexa, send me a pizza hut. Send me Domino's. Everybody in here is looking to build a brand because if you do not build a brand, you will become a commodity. Ah, so I'm going to steal a little bit of Gary's time for my own personal reasons here, but I think it'll...

4:30I've built the biggest business coaching company in the world, 1 ,000 offices, 84 countries, $2.5 billion in sales. I still don't want to be famous. my company should be a lot more famous than it is the people we help the way we help them father of five i always worry about that how did you yeah because you know your dad you got all of that well by the way uh the opening of who doesn't know me let me do the verse how many people here would consider solid fans or have good knowledge of me or follow me carefully raise your hands. So one more time, raise them high. What all these people, brother, will tell you is they don't even know what my kids look like.

5:20I have a 15 and 12 year old. The people that just raised their hands, you include, I'm the most private public person on earth. I don't share my life. I'm exactly like you. I have no interest in people being in my life. My family is sacred. My personal life is sacred. Again, a lot of people just raised their hand. And if you're at a table with them, you can ask them right now, is that true? I put out an ungodly amount of content, but it is not about my puppy or my fiance or my kids. I keep my personal life private. I put out content about business. That's number one. Number two, you still don't even have to do that.

5:59You can make your business famous. To your point, you still don't even have to become the face we're famous, but you need your business to do a much better job in being a brand and build a brand. Nobody knows who Johnny Coca-Cola is. Coca-Cola markets. You don't know the IBM CEO or founder. You know, IBM, right? You don't know, you know, Salesforce, Mark Bedioff is pretty known. Way more people know Salesforce than know Mark. So you just need to make the business market data. your business needs to put out 20 to 30 pieces of content a day throughout social. You don't have to, and you can do occasional stuff.

6:41The clip from this can be clipped and used. And so I think there's ways to do it. Do you see? Yeah. I think, I think from a logical standpoint, I can get all that, but being a little more esoteric at heart, I know that there's a way that if I don't want to do it, it doesn't matter how much content I put out. If in my heart, I don't want that to boom. It's not going to boom. Brother, I don't like anything. I just know what I have. By the way, I hate working out and eating well. I hate it. But I do it because it's right. I don't give a shit about your feelings, brother. I care about your business.

7:24You don't have to do it. You have to hire someone to do it.

7:31All right. You've all heard the advice. Makes sense, right? Oh, it makes a lot of sense. I don't know if... It's also a bit of the Australian in me. I watch other guys. I won't name them, but I'm not the guy that stands up there going, look at me in my freaking jet. God, if you're that rich, you shouldn't be showing photos in your private jet. By the way, I'm that rich? And there's zero photos of me in a private jet. Yeah. I'm with you. Huh? I'm not a douchebag either. Oh, some of them are. It kills me. At the highest levels. If I do any of that, all my Australian buddies call me up. What? Dude, what was that shit you just put?

8:11Why on earth would you do that? I don't know. Some days I read Gary Vee books and it tells me to just keep putting out content. Yes. You're exactly right. But it doesn't say put out douchebag content. Again, if you're really looking at how I do it, I do none of that. I don't even have a piece of jewelry on. I think the shirt's like nine bucks. Like that's, to your point, some people sell the lifestyle, other people live it. I'm a confusion to a lot of people. Thank you. I'm a confusion to a lot of people. When people come and visit me at VaynerMedia and see 2 ,000 employees, half the people that just raised their hands think I'm a motivational speaker.

8:51I run businesses. You do as well. I admire that. I think that's the content you put out. By the way, just so you know, unlike a lot of other people to your point, all the advice I just gave for the last 45 minutes, I do that. Everything I just talked to you about, just so you know, in a world of many speakers that talk about shit they don't do, everything I just told you about, one-on-one time with employees at scale. Content every day. at scale. I'm gonna show you something. This is my WhatsApp. This is where my team and I make the content. That is me. That is me writing the copy to the content that I put out.

9:34This is me with my team. I wrote the copy. I'm still writing the copy on my social media posts. I'm in the fucking trenches. I'm in the dirt. I'm in the dirt more than most of you. Get to do the bits though that you love still. You don't have to do the bits you don't love as much anymore. This is what I'm trying to tell you. This is why I'm doing this little shtick. You don't have to do the content on social. I don't do the contracts of my company. I've signed 45 ,000 contracts probably in the last five years. I've read none of them. I'm being dead fucking serious. But I have Mark Yutkin, who's my brother.

10:15Not my actual brother, but he's been with me now for 20 years. That's it. Fucking figure it out. Uh-huh.

10:28But I am certain someone's going to play that clip back to me every fucking year for the next, like, forever. You know, I'll tell you why I'm passionate about it. I love you for it. I love that you don't want to do what I also don't think is good, which is you're tricking kids and thinking Lambos and watches. That's not what this is about. Why I admire so much about the people in this room is a lot of them are not doing it for the Lambo and the private jet. They're doing it because this is who we are. We're fucking business people. We're entrepreneurs.

11:02So, business question. Charging more. Charging what you're worth. Being the top of the tree. Not trying to be the competing on price people. Thoughts? Always. until the market says go fuck yourself. Right? Like the concept of not constantly trying to get more money for what you do is crazy. Why wouldn't you? Because the market is the market. When you're like, I mean, this is how speaking worked. The first time I did a speaking gig 15 years ago, I get this email. They're like, would you like to give a speech? I'm like, that sounds cool. It was like, I was running a wine store at the time, but I was starting the internet thing, right?

11:39They're like, you want to come and give a talk? So I'm like, yeah. I'm like, yes, I'm in. They're like, it's in Florida and whatever. I just thought he was excited to get asked to speak. He then replies. He's like, how much do you charge? I'm like, fuck, you can charge for this shit? My first ever gig, Robert Kiyosaki took me to Hawaii. I was a 20-year-old kid. And he goes, what's your speaking fee? I said, what's yours? He said this much. I said, same as mine. Mine was pretty funny. So now I get the email from this guy. It's like 2006. six he's like he's like um what's your fee now i'm like sitting there looking at this email and you know remember you know this was pre you know laptops and cell phones like big monitor i'm looking at this thing and i'm like okay because i'm no dope back to the answer i'm giving to everyone here i'm like i gotta come up with the biggest fucking number i could ever imagine to give a speech and I reply I'm like five thousand dollars the guy replies in two seconds to that email he's like done I'm like fuck and the way I got to my price was I kept going and then the market told me you're not that guy yet Gary right when I got to that 25k number at that point in my career they were like that's it because every time i said 30 35 40 it was no we're gonna go in a different direction and i was like respect the one thing i love about this conversation is this is a this is a humbling fun process don't be insecure about this don't be scared to ask but when they tell you you know don't be offended by it just keep asking for more the market will tell you what you're worth where people get this screwed up brother is they're like um I know my worth.

13:25I'm worth more. I'm like, no, you're not. Nobody's paying you. But you need to ask for more as often as possible and don't stop. The other mistake people make is they get excited about what I just said. They get motivated. Whatever they charge, and the next time they charge more, the first person says no and they go right back. You need 10 no's, 7 no's before you've really figured out your price. The first time someone said no to me at 30K, I'm like, you know, because then another no, then another no. And then I had to look myself in the mirror one day and be like, okay, you're a 25K speaker now.

13:57And obviously that's evolved. Well, yeah, I know how much it's evolved. Quite well, in fact. Thank you, sir. But this goes back to why I want you to build more brand. I want you to be in a place where you can fill out 10 times this many people without needing to use keynote speakers. Like brand is brand is brand. And it doesn't have to be you. How would I do it? Well, the more content - Just put out more content. That's right. Because then you're going to have more - And bigger. That's right. And more people are going to be your fans. And then this becomes double the size because they're there to see you, which gives you more leverage to not have to get a top, top.

14:32It's the game. Yeah. It's the game. Actually, speaking of, so we've been in business coaching now for 31 years. Your thoughts on coaching, having a coach? I'm a huge fan of that concept. I think it all depends. like for example in business I never had a coach because it was my god-given gift and I learned more by losing so to me my brain does not process how to be great at business from a coach because I need to taste it I need the L's but many far more successful business people than me a hundred percent attribute their success from coaching I need it everywhere else in my life whether it's therapy, whether it's personal training, whether like, so I'm incredibly bullish of someone looking from the outside in.

15:24By the way, I would benefit from business coaching financially. I just like scraping my knee and banging my elbow in business so much that I keep it away, but it is not lost on me. There are many things in my own game that, and I could see it. You know, you all know this, right? You could see the flaws in everybody in your family, but you can't see your flaw. You know what mom and dad and your siblings and your spouse suck at, but you can't see yours. If I had a coach, for example, let me be very vulnerable, my kryptonite, which is crazy. Some people are going to laugh right now. My kryptonite in business has been candor.

16:05Gary V on stage is very good at candor. Gary Vaynerchuk, the human being, is so into the stuff I told you about employees. I get into family vibes with my employees. Like, you know those lover boys that like fall in love at first sight? That you know, like, I'm like that in business. You like work for me for like a week. I'm like, we're fucking, we're this, you know. I can't help it. I'm just very team, very family. But what that created was the more I liked you, the harder it was for me to tell you the truth about what I thought you were as an employee, which led to me working around it. I would always be very like giving on the way out.

16:47I would have to get years of resentment before I finally had the courage to fire you. And then I gave you a huge severance and you haven't done shit for two years. And now I'm giving you a huge severance. And the worst part of all, you're then mad at me because I never told you. And I surprised you because on Thursday, I'm like, Brad, you're fucking the best. I'm the best weekend. And on Monday, I'm like, hey, Monday, come in and come. Like, and you're the fucking best. Literally Thursday, you're the fucking best. I fucking love you. Hey, by the way, Monday, come in. You come in Monday, I'm like, Brad, we're gonna let you go.

17:12what yeah and so candor was my kryptonite and it took me 20 years and i would tell you as i sit here today in a world where i'm a 10 out of 10 and a 9 out of 10 and so many things in business i'm on a good day i'm still a five and a six out of a very important trait of a leader and i work on it every day if i had a coach i think that would have been addressed much earlier yeah uh Fun thing. The Jets. The New York Jets. Not that fun lately. No, no. Very fun. How many people here are proper football fans that are diehards of their team? Raise your hand. What about of any sport? Who here is a diehard fan of a sport?

17:57Raise your hands. So here's the weird thing about me, and this is why I'm such a good entrepreneur. I love my New York Jets, my American football team, so much. they have not won a championship since january 12th 1969 they fucking suck but i like that part see oh the scrape the knees and the new york jets it makes sense got it i i grew up a new york yankees fan yeah when they won my first championship with them in 1996 I never watched another game Really? Really I actually make fun of all the fans Of very successful teams I feel like you get your self esteem From their victories But you're not doing shit I love the pain I love the grind I love the hardship I love when people make fun of me about the Jets I love that shit I'd love you to help us out With our foundation at some point because we educate kids for free to leave school and be an entrepreneur.

19:07And because, yeah, in, that's in. You'll email me. In fact, I might've mentioned it earlier. Actually, I don't think I brought this up. If I may for a second. Yeah. The thing I'm actually working on right now in my career is the thing I'm most excited about that I've ever done. I've started something called VeeFriends, VeeFriends, VeeFriends.com, especially if you have somebody under 10 in your life, you should go look at it. It is my Pokemon. It is my Disney. It is my Marvel. And it's 250 characters, patient panda, you know, accountable aunt, competitive clown. And it is strictly built to help along with the parenting that is so challenging in today's world.

19:55and a lot of it is targeting the kids that should not go to university and should be entrepreneurs. There's plenty of kids that should go to school. They're built like that. But we got into this place in the last 40 years that everyone should go to university and college, which is insanity. And in America, it's a real problem. Because at least in most parts of the rest of the world, the government pays for it. In America, these kids are going into massive debt to get a piece of cake. My eldest daughter, 350 grand to go to college. My ROI on that? Negative 350. Of course. 100%. It's a joke for half of the time.

20:31But I put her to work with my great friends. You guys all know the Irwin family. Australia Zoo, Steve Irwin, Crocodile Hunter. She goes and works with Terry and Bindi and Robert. She's getting the best lessons in life working for real entrepreneurs, real planet savers. She's working with them. Robert, she's a photographer. Robert's taking her under his wing, teaching her photography. Like, that's better than me. And that's why I'm smiling because the creative set should never go to university. It's not built for that. It's built to make workers.

21:06I'm going to turn it back over to Rachel and they're going to take your questions now for Gary. Thank you. I'll see you in a minute. Cheers. Let's clap it up for the man. Thank you.

From the publisher

In this episode of The $100M Entrepreneur Podcast, Brad Sugars sits down with Gary Vaynerchuk for a candid conversation about brand, attention, and leadership in the age of AI.

Gary explains why building a brand beats competing on price, why social media creative is still the most efficient growth lever, and how to scale to twenty to thirty pieces of content a day without turning your feed into a lifestyle show. Together, they dig into resilience as the default setting for real owners, caring more about your team to drive retention, and the shift in search and discovery that makes it essential to be the name people ask for directly. Gary also shares how he keeps family life private while publishing at scale, how to charge what you are worth and let the market set the ceiling, and where coaching, candor, and accountability fit for leaders.

If you are ready to protect your margins, grow attention, and lead with clarity, this episode is a must-listen.

Don't forget to subscribe so you can always know when a brand new episode is being released. 

About Brad Sugars
Internationally known as one of the most influential entrepreneurs, Brad Sugars is a bestselling author, keynote speaker, and the #1 business coach in the world. Over the course of his 30-year career as an entrepreneur, Brad has become the CEO of 9+ companies and is the owner of the multimillion-dollar franchise ActionCOACH®. As a husband and father of five, Brad is equally as passionate about his family as he is about business. That’s why, Brad is a strong advocate for building a business that works without you – so you can spend more time doing what really matters to you. Over the years of starting, scaling and selling many businesses, Brad has earned his fair share of scars. Being an entrepreneur is not an easy road. But if you can learn from those who have gone before you, it becomes a lot easier than going at it alone.
Please click here to learn more about Brad Sugars: https://bradsugars.com/

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