The #1 Mistake Business Owners Make

In this episode of The GaryVee Audio Experience, I talk about practical optimism, accountability, and focusing on the choices you can control when business or career plans get difficult. I share my perspective on the appeal of in-person experiences, and leading with self-awareness while valuing people. I also discuss finding your own motivation, questioning money as the measure of success, and defining work-life balance around your circumstances. You'll learn about: Practical Optimism And Accountability Creating More Options For Yourself Self-Awareness And People-First Leadership Validation Beyond Financial Success Defining Your Own Work-Life Balance

• 0:00Speaker 00

  I think when people are dealt a bad hand, they go into dwelling, they go into complaining, and worst of all, they go into finger pointing. Sitting in dwelling while you're sitting in Vancouver being like, "I got screwed," doesn't change the outcome. Because when you're a really good entrepreneur, you don't cry about things you can't control. And a good entrepreneur gets a 4 and 7 offsuit in poker and plays their hand. The only thing you're actually in control of is creating the at-bats for yourself and optionality. So I'm saying something pretty important that shouldn't be controversial, which is, feelings are not allowed. This is the Gary Vee Audio Experience.

• 0:41Speaker 01

  You're here with us in Toronto. I write for the Toronto Sun.

• 0:45Speaker 00

  Yes.

• 0:45Speaker 01

  Canadian entrepreneurs are going to be reading about you being here, and I'm sure they'd love to know your take on a couple of things.

• 0:54Speaker 00

  Please.

• 0:54Speaker 01

  One is, Canadian entrepreneurs, they're often described, or Canada in general is often described as being more cautious than Americans. Is that a weakness? Do you see it that way? What advice would you give to a smaller market trying to make it on that bigger stage?

• 1:14Speaker 00

  I mean, look, the US laws, you know, and just the nature of the country's DNA is definitely, please come in, is definitely very conducive to a higher level of energy of risk and entrepreneurial energy. You know, there's no confusion. This is not a subjective opinion. Objectively, I think people know that bigger companies have come out of the US than other places. It's a fairly large, you know, how many Canadians are there?

• 1:47Speaker 01

  Population wise? Yeah, we're at like 36, 38.

• 1:50Speaker 00

  Right, so it's a 10th of, right? So there's that. But then even places around the world that have as many humans that live there as Americans, they are not grounded in capitalism and entrepreneurship the way the American spirit is. And when you see countries like China go from not having that spirit to having that spirit, or if you look at India the last 50 years, which I think has a lot of that spirit, like, yes, do I believe that, you know, American entrepreneurs and businesses have a higher aggressiveness, have a higher level of tolerance? Yes, I think the playing field is conducive for that. Do I equally believe watching Shopify being built from day one to what it is? Or when I think about Sweden and Spotify,

• 2:35Speaker 00

  or maybe people should just start companies with "a-fi" at the end of their name outside the US?

• 2:42Speaker 00

  I have a very clear answer to this. There's not a single A-plus Canadian entrepreneur that should read this and think they can't because they're in Quebec or Calgary or Winnipeg. The greatest thing about entrepreneurship is, even when maybe the tax law or the investing is not conducive to the playing field you're on, if you're actually great, there's no one stopping you. And we've seen unlimited, one of my favorite entrepreneurs of all time, like, let there be no confusion. Garrett Camp, a Canadian, invented Uber. I was in the apartment in London, Paris, excuse me, when Garrett Camp said, including Travis Kalanick, who's known as the Uber guy, was in the room, literally goosebumps right now, said, "I have an idea. What if we had an iPhone app

• 3:27Speaker 00

  where you can press a button and a limousine will pick you up?" So ideas, you know, maybe funding, maybe the general atmosphere, but ideas are not restricted to the US, China, or anywhere else. And so, execution might be a little more challenging, but the best players reading this or listening to this are not being stopped. And do I think they're more cautious? Sure-ish. I know unlimited families and people in America who grow up in academia or corporate DNA whose parents tell them not to start a business. And I get emails and messages from those people constantly. So yes and no is the answer.

• 4:10Speaker 02

  Okay, setbacks, failures, like, big ones, okay? They always talk about resiliency and grit. So give me an example, start with you, Anton. Give me an example of like, one of the biggest setbacks you had and how you almost turned that lemon and made lemonade. Think of this, everyone. You know, let's do the math. We lost $11 million in Tech Deck Live, and then we've grossed over $12 billion in Paw Patrol. Talk about lemons into lemonade. And I'll tell you, Gary, for me, I'm obsessed with there's a gift in every moment. I am so big on this mindset that every time things heat up, whatever, someone gets, you know,

• 4:54Speaker 02

  someone comes through with a problem, the more tense others are, the calmer I am. And you know what I say to myself? I say to myself, either the universe is trying to, there's either a message coming to me, and the more calm I am, the more I get the course correction that needs to happen, or I say to myself, there's going to be a gift in the future, an unexpected gift. For me, there's a gift in every single moment. And the gift from Tech Deck Live was nailing Paw Patrol.

• 5:23Speaker 00

  My biggest mistake in business is so uncomfortably obvious. And it goes down to people and, you know, and offense and defense. There's an old saying I like quite a bit, which is scared money makes no money. I had just bought my first big boy apartment in Manhattan, and I was a little more, I was the least liquid I'd been in a while. And, you know, I'm an immigrant. I was born in the Soviet Union, so like, always having some savings was ideological to me. So when I wrote my first book in 2009, Crush It, I had a friend who was the only person I would let look at it, and he helped me quite a bit and like, refined it. His name was Travis.

• 6:08Speaker 00

  He later became the co-founder and CEO of a company called Uber. When I was writing Crush It, he wasn't working on anything. And then Uber came along. I was actually in the room when Uber was like, first talked about, because it's not Travis's idea. Actually, the person who came up with the idea of Uber is a nice Canadian boy named Garrett Camp, who was also the founder of StumbleUpon. I was literally at Le Web after giving a keynote in a room in a version of Airbnb that was in Paris when he literally said to like, 12 of us, "Hey, I have this idea. Could you imagine with the iPhone, you could press a button and get a limousine?" That was literally what happened.

• 6:53Speaker 00

  Anyway, a few months later, they asked me to invest in Uber. I had been investing very rapidly during that time. Like, if I like, "I like your socks, bro," right? If I met a kid that I liked their socks, I would write a $25,000 check. It was so fucking entrepreneurial and random. But I had just bought this apartment, and I was not liquid. And even though I thought Travis and Garrett were the best, I decided not to invest. And so I passed. They were so close to me and so wanted my help that they came back a couple months later and were like, "Hey, we still want you in. We're doing our angel round." And I passed again.

• 7:36Speaker 00

  If I had written my normal $25,000 check at that round, I would have made somewhere in the range of $540 million on the IPO.

• 7:48Speaker 00

  So that was bad.

• 7:54Speaker 00

  The way I handled, there was no win. I didn't fix that, nothing good happened.

• 7:58Speaker 02

  The lemon didn't turn into a lemonade?

• 8:01Speaker 00

  Here's how I deal with things like that. And I'm a very big believer in this, which is very real to me. Obviously, if I had made that investment, my whole life would have been different, like the butterfly effect, right? Like, things just would have been different. And I basically believe if I made that investment that I would have been in China on business and one night not paying attention when I crossed the road, and a bus would have hit me, and I would actually be dead right now had I not made that mistake. And so I guess the win for me is that I'm alive.

• 8:35Speaker 02

  That's some great lemonade.

• 8:37Speaker 00

  I genuinely on the record believe that. And I don't know if that's a coping mechanism subconsciously. But I really, you know, I think what's important about what you said. That I also in the same way, like when it's the worst, I'm my best. And I believe that there's some sort of entrepreneurial spirit, but I think it's more grounded in something I wish on all of you. Besides health and self-awareness, the number one thing.

• 9:04Speaker 02

  Glad you said self-awareness.

• 9:05Speaker 00

  It's massive. But besides health.

• 9:07Speaker 02

  Most people don't realize what their true self-awareness is.

• 9:10Speaker 00

  I agree.

• 9:10Speaker 02

  You ask a person in this room, they'll say an eight, it's a six and a half.

• 9:13Speaker 00

  I believe that to be true. And maybe a four. Cause I think people are incredibly detached from that trait.

• 9:20Speaker 02

  People do not invest enough time in their.

• 9:22Speaker 00

  But I will say, besides health and self-awareness. The thing I would wish on you most is practical optimism. I think we live at a time where cynicism has exploded. Because of the nature of the world. I believe that most people are no people. And I think that being in the maybe business with a swing towards yes. And I think if you hear what he said about when it's bad, the world is teaching me a lesson, I'm gonna learn, bless you. You know, I'm gonna learn from this. I do not believe that's how most people process. I think when people are dealt a bad hand, they go into dwelling. They go into complaining and worst of all, they go into finger pointing.

• 10:07Speaker 00

  And I think accountability and optimism is disproportionately the trait that leads to, forget about financial success. Deals to the thing that I most care about, which is how do I get stress and anxiety off your chest? And so that's what I do. And so yes, that's a loss of obviously. In my quest to buy the New York Jets, that would have been a good, that would have been a good additive financially. But I'm completely convinced that passing on it was a good thing for me. And I think more people need to choose things like that to allow them to move forward.

• 10:43Speaker 01

  Now, Canadian business owners navigating some unpredictability right now, especially with our southern neighbor.

• 10:52Speaker 00

  Yes.

• 10:52Speaker 01

  You know, trade talks and tariffs.

• 10:54Speaker 00

  Yep.

• 10:55Speaker 01

  What would you prioritize if you were talking to a Canadian entrepreneur over the next six months? What would you stop spending money on if you're, if you're feeling the uncertainty right now about expanding your business? You know, what kind of takeaway should Canadian entrepreneurs be considering?

• 11:13Speaker 00

  Well, whether there's tariffs or not, or geopolitics or not, you know.

• 11:19Speaker 00

  In two and a half years, when Trump's not in office, if there's a different policy. It's still not going to change the reality of entrepreneurship, which is you have to deal with the reality of the business you're in. Meaning you stop spending money on dumb shit, whether there's tariffs or not.

• 11:33Speaker 01

  So that's a common sense approach.

• 11:35Speaker 00

  Yes, because, because when you're, when you're a really good entrepreneur, you don't cry about things you can't control. For example, I, I was born into a, you know, a situation where the family business I got was a liquor business. And the laws, I was right about the internet in the mid nineties. Had my father had any other business, I would have built a much bigger business. But the laws were so not in my favor. Every week I was getting cease and desist and you can't Shapiro anymore. It was a constant flow of adversity. Right? I couldn't cry about it. Hey, I could have went and sold books if I wanted to, and that would have been good because Jeff Bezos did that.

• 12:19Speaker 00

  But I never really cried about it and I did what I could. I want, I knew I was building my father's business, so I wasn't going to go sell something else. And that was the hand I was dealt. And a good entrepreneur gets a four and seven offsuit in poker and plays their hand. To cry about tariffs constantly as a Canadian entrepreneur means that you're a bad entrepreneur.

• 12:40Speaker 01

  Okay, okay.

• 12:42Speaker 00

  It's the truth.

• 12:43Speaker 01

  Okay, I bet that's a controversial take, but it's the truth.

• 12:45Speaker 00

  It's, it's the most common sense approach. Like I, if you're selling, if you're, you know, spin master, like if you're a company. What are you supposed to do? Like, I don't think you can fly to Mar-a-Lago and change the outcome. So like, you know, to the question you asked, what do you stop spending on? You stop spending on dumb stuff, no matter what the temperament is. You know, when you're running a business, if, to your point, if you're cruising and then crap, a politician in the biggest market just fucked up your whole sitch. You have to go into an emergency meeting and say, okay, like when AI got cooking three years ago. I had emergency meetings saying, what do we do for a living here at Vayner? That can be commoditized by it. And I've been prepping for no one wanting to hire us for three years.

• 13:30Speaker 00

  Like, but I didn't know AI was gonna pop up that day when chat GPT went viral, you know, for three, four years ago, like. And just like a Canadian entrepreneur couldn't ever have predicted that Trump's gonna wake up and create tariffs. And again, that's political versus innovation. And so I'm saying something pretty important that shouldn't be controversial, which is feelings are not allowed.

• 13:50Speaker 01

  Yeah.

• 13:51Speaker 00

  Feelings are not allowed.

• 13:52Speaker 01

  It's not about the politics, it's not about the tariffs. No, not at all. It's, it's that feelings may not have place in business. Exactly.

• 13:59Speaker 00

  It in, in, in a dwelling format. You're a human, you're not a robot, but like sitting in dwelling. While you're sitting in Vancouver being like, I got screwed, doesn't change the outcome.

• 14:11Speaker 01

  Right.

• 14:11Speaker 00

  What, you know, and so you have to start going to the places where you're wasting dollars. Whether that's people, whether that's on marketing in the US, if you're selling there and now your product's not viable, you know, it just is. The good thing with this one is unlike AI, AI is not gonna stop, but tariffs can go away. And so ironically, you will write plenty of articles in seven years. On businesses that got even bigger because of it, because they got even sharper during this tough time. That when the tariffs changed, they cooked with gas.

• 14:40Speaker 03

  Hey, um, my name's Lola. I just have a quick question. So my question, just so you know, I was at Twitter during the acquisition, that was hell. Um, I will say that my question is around structural barriers. So I have worked in the tech sector for, for years. And I love everything that you all are saying, but I hear it and I call bullshit.

• 15:08Speaker 00

  On which part?

• 15:09Speaker 03

  On a lot of it.

• 15:11Speaker 00

  Give me one example.

• 15:12Speaker 03

  Um, so for example, the idea that, um, just, um, the idea, sorry, I wrote it down here. So the idea that when you just have self-awareness, um, you champion, um, you champion. Specific things that are good for the company that actually plays out. I've not experienced that. So my question is.

• 15:34Speaker 02

  You're on the wrong, you're on the wrong environment.

• 15:36Speaker 00

  Well, I mean, I think it's fair, like in how many different companies, I think is the next word.

• 15:40Speaker 03

  Three.

• 15:40Speaker 00

  Yeah, I mean, I think that makes a lot of sense to me.

• 15:43Speaker 03

  So for me, it's, it's, it's, the question is, so how do you address it when there's structural barriers? So I'll give you an example. I was having a conversation with someone who's an entrepreneur. And about precisely that, should I go to a smaller company? And he says to me, this is a month ago, this is in Toronto. And he said to me, um, at the end of the day, you're not white, this is verbatim. You're not white, you're, you're young, you're a black woman. I don't think this is gonna work out for you this way. So.

• 16:21Speaker 00

  You mean a smaller company?

• 16:22Speaker 03

  Yeah. So he felt.

• 16:24Speaker 00

  You believe him?

• 16:25Speaker 03

  Well, he felt that, um, some of those opportunities typically go to the friends of the founder. So if there is less funding for people than this, than that, than that, you're probably, he was trying to be helpful.

• 16:40Speaker 00

  Yeah, I just sound like that.

• 16:41Speaker 03

  I'm not, I don't even, he was trying to be super helpful. Um, and I think for me, then the question starts to be what? Cause I think there are other people here that probably face, whether you're a woman or something else, whatever. So what do you do when there are actual structural barriers? Versus, I love it, it's great, students, please do the right thing. He said all the great things and that helped me for the first, I would say at least decade of my career. But I will tell you, you keep hitting a wall and for me, my question is.

• 17:16Speaker 00

  How do you deal with that? My, so a couple of things. All, most of what I was talking about, at least in this talk, had so much to do with like being the person in control. Even my first hand was, you know, I don't want to be at the mercy of anyone, let alone to your point, structural or a boss or things of that nature. So there was a lot of entrepreneurial framework. That's A. B, to your specific situation, and I, I could tell by the way you were telling the story that that gentleman, it sounded like was coming from a good place, right? I'm a very big fan of optionality, right? You know, to me, I'm empathetic to that point of view and all of that has, is grounded in truth, especially the bigger the company it is, right?

• 17:58Speaker 00

  But until like ultimately you're looking for a place where you can grow, you're going to be at the mercy of leadership, right? And whether that's, you know, back to Toronto, whether that's Shopify or things of that nature, they're all going to have different chapters and seasons. I think for you, because it seems like you're progressing really nicely in your career, you're going to have to make a subjective opinion around the leadership. And to your point, the bigger the company is, you might decide on a company that seems right and the next month there might be a reorg and the barriers come in. It is not a question that is so easy to answer. You're completely at the mercy of the serendipity of the humans that are leading the thing. The only thing you can control is more optionality, right?

• 18:43Speaker 00

  That's just the truth of it. There's no one that's going to be able to fix the strengths and shortcomings of an organization. There's only the realities of the leadership that has full control and the life cycle the company's in. The thing that I think you have going for you, that's like a pretty fucking real resume that you're talking about the companies that you're at. You're, you know, and I'm incredibly empathetic to like, you know, all the subjective and subconscious, if not conscious biases that go into everyone making a call. The only thing you're actually in control of is creating the at bats for yourself and optionality. And I think that's the biggest thing you're going to have to focus on because that's the thing you can control. You can't control who the founders are or to your point, the, you know, when Jack Dorsey's running Twitter and the next day you wake up and Elon bought it.

• 19:27Speaker 00

  These are just things that are so above all of our pay grades. I, and you can, to your point, you can get really caught up in the things that you can't control. You know, my biggest hope is for you to like, get the momentum of the things that you can control. Hey everybody, 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.

• 19:51Speaker 01

  So switching to AI. AI promises to help businesses do more with fewer people. What responsibility does an entrepreneur have to their loyal employees whose work could maybe be now found to be automated, redundant? What's your take there on?

• 20:08Speaker 00

  I think that's, I think that's incredibly personal. I can speak for myself. I have taken the approach that I'm willing to make less money because I do value loyal employees. I like it. I'm only into business because of people. I do not think that's the right path for most people.

• 20:25Speaker 01

  Really?

• 20:26Speaker 00

  Yeah, I think most people might not be able to afford the ability to choose altruism. And I'm just so talented that I won't go out of business. I'm just going to make less money. That's the truth.

• 20:38Speaker 01

  Yeah, but I hear you.

• 20:39Speaker 00

  That's the fucking truth. Yeah, and I'm just, I'm also very comfortable with making less and mainly because God forbid, if I lose, I'm okay with it. A lot of people can't handle that. If they lose their business, they go into alcoholism. They go into like really scary places. I like secretly dream about losing everything and starting over on some like weird Rocky six. Like I don't even understand what's going through my body sometimes. I'm being serious with you. So like for me, when I think all of this is silly and it doesn't matter, if I choose people and lose, I'm going to wake up the next morning and be like, that was crazy. Other people are like really in a bad place. And so, you know, bosses are going to do what they're going to do. First of all, anyone who's a publicly traded company

• 21:22Speaker 00

  doesn't have the legal, let alone, you know, kind of ideological framework to even do what I'm saying. They have a fiduciary responsibility to their stockholders legally. They should be firing the shit out of people legally.

• 21:36Speaker 01

  If it's best for the business.

• 21:38Speaker 00

  And most people will do that. My point of view is actually on the other side of the, of the aisle. I think this is not about bosses being altruistic because I'm a one in a million and there's others like me. But the most people will not choose people over profit. What I think needs to happen is the people who have jobs need to go and make sure they're more bulletproof. You know, I even take difference with your sentence. I do not believe that more gets done with less people. I believe that. I actually truly view it this way. I can tell you how I'm running my companies. If you play out the chess moves, I think every one of us has, let's just play it out. We have the power to be way more productive. We could all agree that we are all with what we all do. We could be acting depending on looking at all of us, the impact of three of us or 11 of us.

• 22:23Speaker 00

  Let's just play that. If I'm competing with every other agency, if I fire everyone and go from 2,000 to 100, but those 100 act like 1,000, but another agency keeps their 2,000 and they act like 20,000, I'm going to lose. I, I think people are very confused on how this is all going to play out. The end. I actually think a lot of businesses are going to win by empowering all their people with it and outflanking their competitors while their competitors are penny pinching it. And their competitors are going to be happy about profits in the short term and they're going to wake up and lose business to the people that double down on AI-enabled people. That's my spidey senses. It seems very logical, by the way. In the short term, it makes sense. Oh, here's a quick way to maybe drop some EBITDA. You know, if you're selling your company

• 23:07Speaker 00

  and you're going to get a multiple on your EBITDA, do it. If you're the public CEO and you want the stock price to double because you're going to sell your shares, do it. But if you're playing the marathon of building a business, you're going to get caught.

• 23:19Speaker 01

  And so your, a tip then to employees who might be reading this column is get, get trained.

• 23:27Speaker 00

  Get trained, like, like crying about like AI is going to take my job when the truth is a human using AI is going to take your job. Is like something people have to wrap their head around. The world is 50 trillion times more productive than it was 100 years ago. This is just doing the same thing in a more condensed period of time.

• 23:45Speaker 04

  I'm going to pivot and ask a question that's further down because it picks up on something you said. And I hope it's the right quote that I picked out from you. I think it was a Forbes article, but I loved it. I think you said, extreme AI, extreme analog, don't get caught in the middle.

• 24:00Speaker 00

  Yes.

• 24:01Speaker 04

  Everyone here, I guarantee you, is thinking at some point, hmm, is Gary and then Anton going to tell me what they think about AI? Because that's all we keep hearing about. But your quote really was provocative and I loved it. And so my question is, first of all, how do you think AI is going to change business, people, careers? And then how do you lean into that analog side at the same time? Like your quote suggests?

• 24:25Speaker 00

  I mean, how, to answer you directly, I think it's one of the most significant changes we'll ever see. I think AI is our generation's electricity. So I was a really bad student. Ranked 243 out of 254 in my high school class. But what kept me from the other 11 at the bottom was I was good at history. And I never understood why, but it was the only class I paid attention in. And in hindsight, I realized now later in my life, oh, I used history because probably subconsciously I knew it was going to matter for me in business because I think the past tells you the future. I think AI is going to change every single person's life in here in a pretty profound way to the levels of the internet for the people that are over 45

• 25:09Speaker 00

  and here that really lived a life before the internet and now have lived their life. We could see how different things are. It's a big, big deal. That being said, the quote, and I fully believe this, in extreme AI is the rise of analog. It is very clear what's going on. In fact, the number one startup I'm trying to figure out to invest in is which dumb phone company is going to win. It's so obvious what's happening with how we're going to sporting events, music. It's so obvious what's happening with modern dating. How many people are starting to swipe left against online dating? Like there's a lot going on. The youngsters know it because they can feel it. They definitely know it if they have 14, 15 and 16 year old siblings because they watched them get over technologyed out.

• 25:52Speaker 00

  So they're pushing against it. I'm obsessed with restaurant businesses. I'm obsessed with experiential. I'm obsessed with dumb phones, CD players. I'm trying to start a drive-in movie theater business right now, actually, where not only that, the towers around the radius of the movie theater kill your, your cell service. Like I'm opening a restaurant where you have to put your phone into a locker when you first go into the restaurant. So I'm excited, like I have an open claw that runs my whole life. As a, as a personal brand, I'm posting now 900 pieces of content a day using a 30-person team and AI at scale. My harness and computer, my open claw GROK,

• 26:35Speaker 00

  you know, my Muse, like my infrastructure around AI is like 11 out of 10. I am obsessed with AI. I'm all in. I'm all in. I'm all in because I believe AI will play out the way alcohol and firearms and many other things have played out. I do not believe we do not have will in this room. I believe humans have will. And I think we will know how to handle AI. And I think it is the biggest opportunity for everybody in the room to understand what's actually happening here, which is, are you going to have a subjective, probably politically charged opinion on AI and stay on the sidelines? Or are you going to go all in and understand that if you don't,

• 27:17Speaker 00

  that anyone who's fought modern technology has lost? And so you could be ideological about it, but that's not going to change what China or Russia or Elon do with it. Or you could move in and understand it is the weapon of choice for you. And more importantly, final thought, thank you for the time. Everyone here is going to interact with AI in 10 years at hyperscale 24 hours a day. So you can be your grandma that you made fun of 10 years ago about some other technology and have some weird point of view on it based on some ideology of like where we're at. Or you can deal in reality and realize you're only in control of your actions and what you do.

• 28:00Speaker 00

  And everyone here will be required to interact with AI or you'll have to live on an iceberg somewhere random.

• 28:06Speaker 01

  What's the single most important trait you look for when hiring an executive?

• 28:10Speaker 00

  Humility.

• 28:12Speaker 01

  In an executive?

• 28:13Speaker 00

  Yeah. I need self-awareness. I can do anything with an executive if she or he knows who they are.

• 28:22Speaker 00

  If they're delusional, we're stuck.

• 28:24Speaker 01

  Okay.

• 28:24Speaker 00

  Because inherently, they'll be political if they're delusional. And politics fucks up culture.

• 28:29Speaker 04

  Gary, I want to jam with you on a topic that I'm concerned about. Concerned? I'm really concerned about the decrease in open-hearted leadership, the human leadership and leading with heart. And are you guys being taught enough in business school?

• 28:43Speaker 00

  Let there be no confusion. No business school 30 years ago was talking about fucking heart.

• 28:50Speaker 04

  No, what I'm saying is...

• 28:51Speaker 00

  Oh, I know what you're saying. And I'm gonna say it again. Forty years ago, HBS and fucking McGill and all these fucking places were not teaching like, "Let's be nice."

• 29:03Speaker 00

  Do I think these youngsters are gonna be heart-first, human-based leaders? I don't know. I don't know their parents, and I don't know their environment, and I don't know their DNA. My intuition is that 85% of them will not be, and 15% will be, just like it's always been. The question becomes, what's the temperament of society at the time that they're playing the game? Right? So 20 years ago, when I was talking about the values of being nice, nobody was listening to me. Because the world was just kind of trucking along. Um, today, I think it's swung the other way. Like now, we're, you know, in a lot of pockets, anti-capitalism. You know, the rise of socialistic DNA has grown quite a bit,

• 29:44Speaker 00

  which has created a counter to extreme capitalism, and it's like, no one's in the middle. The value of it's very clear. Like, you know, when you have retention in your organization, the math is very clear. Organizations that have long-tended retention tend to have better margin, more profit. But, as you know, things get corporate. If they, if all these youngsters decide to start small family businesses with 30, 40 people, it's a higher propensity that there'll be more heart in the organization.

• 30:12Speaker 04

  Exactly.

• 30:13Speaker 00

  If they go and build a corporation with 14,000 employees, things tend to get corporate. What's cool, though, is it depends on how much they give up control. My favorite thing about business is it can be remarkably good in culture. It just means that the founder, the monarchs, the gal or the guy that runs it, has to have control. If they don't have control, and the board has control, the stock price has control, the EBITDA has control, because they want to sell the company on a multiple against the EBITDA, they will choose profit. If they do have control, and they are not in that place, and they happen to be a good person, and they care about a balance between profit and people, that will be a great place. It's why monarchies really work until they don't.

• 30:56Speaker 00

  Monarchies are epic until the grandkid nepo comes in and they're a jerk, and then the whole thing falls apart. But I think the best businesses are monarchy, and it completely maps to the leader. You know, the most unhappy person in all my companies is the CFO, because he knows, or she knows, that I'm not maximizing margin. And there's only one reason that happens. Because I choose to do a lot of human things that cost us profit.

• 31:19Speaker 04

  Yeah.

• 31:19Speaker 00

  That's, it's not very cool.

• 31:20Speaker 04

  Glad everyone heard that.

• 31:21Speaker 00

  I don't think the kids are like in some, like, business schools taught nothing about this and continue to teach nothing about this. But who they're gonna be comes down to their environment, their DNA, and their reality. And there was tons of nice people running companies in the 60s, 70s, and 80s, and tons that weren't. And that will continue forever, and I just, you know, but things do get more and more popular. My biggest concern, to be frank with you, is the rise of entrepreneurship popularity. Forty years ago, nobody became an entrepreneur because it was cool. And now, it got cool in the last 25 years. And I worry about that because it's incredibly lonely and you can't hide. You know, you can hide in academia. You can hide when you're an employee. You just blame your boss and say, "I got fired because my boss sucked." Meanwhile, you sucked.

• 32:07Speaker 00

  When you're an entrepreneur and your business fails, you can't point fingers. And that gets very lonely and very challenging. And so, back to self-awareness. The number three at Facebook, and the number seven at Google, and the number 13 at SpaceX, did a lot better than the founder of 99.999999% of companies. I'm hoping that people don't start businesses because they think it's cool where the money is. I hope they start it because it's the only option for them. And if it's not the only option, that they understand that they might be a number two, or a number three, or a number four, and that could be remarkably more lucrative, not only financially, but far more peace of mind.

• 32:43Speaker 04

  Hardest leadership lesson that you have learned?

• 32:46Speaker 00

  Mine was the reverse. Too much culture. In all these nice words I've said, let me warn you if you're like me. I went too far the other way and created nepotism and entitlement. If you follow my content, you probably know that I talk a lot about parenting, and I talk about like, "Don't go too far," and making it, "Don't over-coddle these kids," and all that. I come from a place of knowing how, I made it so yummy and phenomenal in my world and put everything on me. Through therapy, I realized I have superhero syndrome. So like, I just put everything on me. And that was awesome and made everyone super happy, until it went so far that C and D players became entitled and were not making it as good for A players. They started to become frustrated because merit matters. And it was like, talk about a devastating day in my career.

• 33:31Speaker 00

  Like, looking in the mirror and being like, "Oh, crap." Like, because what would happen is when we would have to fire someone, they were pissed. Because on Friday, what's your name, I mean? Ryan. On Friday, I'd be walking out of the office, and I'd go up to Ryan and be like, "Ryan, you're the fucking best. Like, I have the best week. What are you doing this weekend?" And then on Monday, I'd be like, "Ryan, you need to come in." "So Ryan, you know, you stink. We have to fire you." And he'd be like, "What the fuck? Friday, you told me I was the best." So we weren't good at giving candorous feedback. So it was all rainbow and sunshine, and then a stunning firing. And I used to be mad at Ryan and be like, "Why is Ryan mad at me? I held him here for 18 months too long. I was carrying his ass. He sucked. Everyone knows he sucked." But Ryan didn't know he sucked. Which is why he sucked.

• 34:14Speaker 00

  And so, that was a really tough pill for me to swallow. Because it's crazy. Gary Vee, my public content, candor's my strength. I keep it super real on stage and in content. But as an operator, I'm a little bit too much of a lover boy, right? Like, if somebody works for me for like a week, I'm like, "We're family now, right?" Like, I'm very into team. I love it. It seemed like a gift in my 20s and 30s. But as my career advanced, I was like, because I was like, "Why are some people mad at me? Like, why would someone be mad at me? I'm like, the best." You know? And I was like, and I got into a place in my early 40s where I'm like, "I have to be accountable." There's a group of people running around the world that aren't fond of their time with me. And they were all the same. Like, with all due respect to them, they were underperformers that weren't being communicated to,

• 34:59Speaker 00

  weren't given a chance, to their credit, to fix it. Because it's all sunshine and rainbows, and then were baffled by the firing. And so, mine was the reverse culture. It was too much entitlement, too much, however you want to use the words. And we created entitlement at scale. And the organization became bloated. The organization became less effective. And now, we call it internally, in our HR department, we call it kind candor. And it's changed our company. If anyone's running something right now, and this is hitting, kind candor has changed all my companies. I have 4,000 employees across all my companies. Kind, you can't debate kind candor.

• 35:34Speaker 04

  Your book, okay? It's all about embracing what makes us different. Right? We've talked about this a lot, and you've given some examples here. But I want to know, when you stopped trying to change who you were and really leaned into embracing those differences and who, what made you you? Grade nine, I'm at AY Jackson up north, and the English, the English teacher says to my mom, "Anton will never get into university."

• 36:06Speaker 00

  It's good.

• 36:07Speaker 04

  You know? And at that time, I felt underestimated. I, I felt the world was underestimating. I felt like I wasn't enough. And what I didn't realize at that time was...

• 36:19Speaker 00

  I apologize. You felt both of those things? Because they're quite different energies. If you feel underestimated, that's different than feeling insecure. Or did you have both, and they were pulling from opposite directions?

• 36:32Speaker 04

  I think I felt more underestimated.

• 36:34Speaker 00

  Makes sense.

• 36:35Speaker 04

  Yeah.

• 36:37Speaker 00

  Super, I'm sorry to interrupt. That's super important. Because I also, and again, I think a focus group of two is a complete waste of time. But this is something that I've observed for a long period of time and have been fascinated by. All of you, whether you're 60 in this room or 20, you've got to decide what happens when the world tells you something.

• 36:59Speaker 04

  Exactly.

• 36:59Speaker 00

  And you either believe them, or you don't. And I will tell you, the people that don't believe them tend to do quite well. Um, and there's something very real in that. Like, when my teachers told me that I was going to be a, you know, we grew up in a similar era. Kids, you're gonna love this. Teachers in the 80s and 90s, my ninth-grade science teacher told me, "I am a loser and will never amount to anything," directly to my fucking face. I walked back to my desk and I'm like, "I make more money than her now selling baseball cards. How could I possibly be a loser?"

• 37:36Speaker 00

  But, but a lot of people believe parents, people they look up to, or authority.

• 37:43Speaker 04

  I want a follow-up question to something you said. Not this one. But you talked about, you talked about, I didn't have a chip when people told me, like Anton did, "No, no, no, you're not good," etc. So I want to know, because you talked about that school, not really for you. What was that deep motivator for you? If it wasn't people saying in school, "No, no, no." Wasn't it? That clearly wasn't it for you?

• 38:07Speaker 00

  I have no interest in proving any of you wrong, or anybody that said I couldn't. I actually can't hear you. It's what's kept me in a very good place as things have worked for me. I don't believe the accolades either. The admiration, the selfies, the flowers, the love that I get. I don't hear that either. I'm only playing for two things. To make my parents proud, and my own curiosity. I'm just curious how good I am at my game.

• 38:35Speaker 00

  I play for me. You know, you ever see Rocky, the one with Drago, right? This is my favorite thing. It's very subtle in the movie. Like, when Drago loses to Rocky, and he yells at the Russian premier in the crowd, he's saying like, "I'm not in here for country versus country. I'm fighting for me." I'm not playing for anybody in this room, or anybody in the world. A little bit to my parents, because I adore them, admire them, and I think I'm like many human beings, where you want to make your parents proud. Other than that, I'm in my own game for myself. I have no interest in proving anything to anyone in this room or this world. Because why on earth would I? Who the fuck are you?

• 39:20Speaker 00

  Thank you.

• 39:22Speaker 00

  I think it's a very important point. I want more people to challenge themselves of who they're playing for. I believe most people are incredibly insecure because they're looking for validation from everybody but their own selves. I know, the reason I play for my parents is because the way my mother parented me gave me everything I needed, right? I, uh, I, all of my validation, and I mean all of it, comes from who I am as a human being. How nice I am and how I treat people. I do not think you should put anyone who makes money on a pedestal. I mean, it's good. I like being good at entrepreneurship. I'm glad I'm a good businessman. But I think we've lost our way. The concept that you're good at making money

• 40:06Speaker 00

  puts you on any pedestal above another human, I think is fucking ludicrous.

• 40:11Speaker 05

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• 40:40Speaker 00

  It's a skill. I mean, I like it. Like, trust me, my greatest passion is being an entrepreneur and being a businessman and doing more. I love it. I love it. It's my game, no different than someone who loves baking or playing golf or painting or what have you. But the concept that we've gotten to a place in our society where there is basically this binary belief that you're successful because you're good at accumulating dollars is fucking wrong.

• 41:07Speaker 00

  Like, if you're good at making a ton of money, but you're a complete piece of shit, is that good? No. So like, why do we act like that? I, I actually despise most of my friends that make money.

• 41:17Speaker 00

  Not because they made money and fucked billionaires and that bullshit because that's ludicrous, because I don't like the way they treat people. And that is my binary measurement of who a human is.

• 41:26Speaker 01

  Last question. I'm a lawyer, I'm a business owner, I run my own law firm, I'm a mom. So I write a lot about this question or ideal of work-life balance. What does sustainable ambition look like for someone who wants to build a successful company who has all of these different roles in their life?

• 41:46Speaker 00

  Patience. It's a seasons game. I'm just so fascinated by people struggling with that. Like, first, it has to be your work-life balance. No one can aspire to anyone else's. You don't know their circumstances, you don't know their partners, you don't know their kid situation, you don't know. And then, I'm sure you know this because we're not 18 anymore. Like, you're gonna be a different version of yourself after each chapter of the way. And for a lot of people, there's that 20 to 30-year window, depending on how far apart their kids are, where there's children in the home versus children not in the home. And if you have kids at 25, younger side for today's world, and you're 43, 45, 47, when your kids are out of the home, you've got a whole nother 20-year run in front of you

• 42:31Speaker 00

  versus if you go ham on your career and you have kids later and you have kids at 38. Like, this concept that anyone... First of all, the concept that there is an actual blueprint to work-life balance is silly. You know, everyone's work-life balance is defined by themselves. And then, more importantly, when you double-click into it, it's incredibly seasonal, right? And also has a lot to do with how much joy you get out of your job. You know, so some people, people are very confused. Like, I think people think it's a financial thing. I actually think it's a passion thing. Like, I see a lot of people who, like, just are crazy workaholics who don't make a lot of money because they picked a career that doesn't make a lot of money, but they fucking love it. And so they're just working all the time because it's their hobby. Right?

• 43:15Speaker 01

  Yeah, yeah.

• 43:15Speaker 00

  Like, you know, and so like, I just think it's incredibly contextual and I'm very empathetic. I think, I think for me personally, the concept of ever judging anyone's work-life balance or their ambition is just so silly to me. Like, I think the key is to be very in tune with yourself. You know, I think the goal of one's life is to minimize the pressure that's pounding on your chest. And, look, finances come into that because money pressures bother a lot of people. But I also think if they, if they had humility, if they don't make a lot of money, they could live within their means. There's, I mean, I grew up in very dirt situations. I have a lot of friends who are quite solidly happy, who make 60,000 to 80,000 a year. They're living incredibly humbly

• 44:01Speaker 00

  by standards of like big-city life, right? And then I have friends who make fucking $900,000 a year who are stressed financially all the time because they're overly bougie and they don't have savings. Like, so I think, you know, I think keeping up with the Joneses and the rise of materialism has really hurt our collective happiness. That has nothing to do with work-life balance or like, you know, cost of living is up. These are truths, but again, just like what's going on in France right now. Like, you know, one can control their outcome. I grew up in an immigrant family that spent no money on anything my whole childhood. We were super happy. We didn't have shiny things, like, but we had happiness and content and love. And like, I think we've lost our way.

• 44:45Speaker 00

  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.

• 44:54Speaker 06

  Para los grandes, para los chicos, para los bajos y los altos, los pacifistas, los valientes, para los optimistas y los pesimistas, los que valoran lo de adentro. Para los que están lejos, los que no vende lejos, y los que no vende cerca. Para los introvertidos y los extrovertidos, para los que piensan y los que hacen. Para los que nos mostraron el camino. Coca-Cola, para todos. Compra una Coca-Cola en una tienda cerca de usted.

• 45:25Speaker 05

  It's getting chilly outside. But you know what that means?

• 45:31Speaker 05

  It's time to cozy up with Panera Bread. Let's get toasty, cheesy. Oh, hello, broccoli cheddar soup in a bread bowl. How about melty? Okay, Chipotle Chicken Ovo Melt. It's dipping bread and soupy goodness season. Oh yeah, we're so back. It's Panera season. Order now.

• 45:54Speaker 00

  Journey. See you later.