Leap Academy with Ilana Golan - GaryVee: The Mindset That Took Me from Zero to Multi-Million-Dollar Success | E115

Episode Date: July 8, 2025

Being scrappy wasn’t just a choice for Gary ‘Vee’ Vaynerchuk; it was his only way forward. After years of growing his family’s wine business, he was left with nothing of his own. With no money to rent an office or hire employees, Gary leveraged his grit, relationships, and opportunities to launch VaynerMedia. Overcoming the financial, mental, and emotional hurdles of entrepreneurship, he built his company into a multi-million-dollar media empire. In this episode, Gary joins Ilana to reveal the mindset and strategies you need to overcome obstacles and build your own multi-million-dollar business. Gary Vaynerchuk, famously known as GaryVee, is a serial entrepreneur, chairman of VaynerX, CEO of VaynerMedia and VeeFriends, and a six-time New York Times bestselling author. Recognized as one of the most forward-thinking minds in business, culture, and the internet, Gary helps brands stay ahead by spotting trends early. In this episode, Ilana and Gary will discuss: (00:00) Introduction  (01:40) VaynerMedia's Scrappy Beginnings (06:56) Why Businesses Fail Financially (10:01) Navigating Tough Business Days (17:21) The Risk of Over-Transparency in Leadership (19:44) Dealing with Failure and Public Ridicule (22:10) GaryVee’s Dream of Owning the New York Jets (26:06) The Role of DNA and Accountability in Success (28:35) Finding Joy in Entrepreneurship (31:02) How to Build a Personal Brand as an Employee (32:30) Empowering Employees with Honest Feedback (34:27) Embracing Change and Executing Relentlessly Gary Vaynerchuk, famously known as GaryVee, is a serial entrepreneur, chairman of VaynerX, CEO of VaynerMedia and VeeFriends, and a six-time New York Times bestselling author. He is a prolific angel investor with early investments in companies like Facebook, Twitter, Tumblr, Venmo, Snapchat, Coinbase, and Uber. Recognized as one of the most forward-thinking minds in business, culture, and the internet, Gary helps brands stay ahead by spotting trends early. Connect with Gary: Gary’s Website: garyvaynerchuk.com  Gary’s LinkedIn: linkedin.com/in/garyvaynerchuk  Resources Mentioned: Gary’s Book, Day Trading Attention: How to Actually Build Brand and Sales in the New Social Media World: https://www.amazon.com/Day-Trading-Attention-Actually-Social/dp/0063317591  GaryVee: From Earning $2 an Hour to Running a $350M Digital Empire: https://podcasts.apple.com/us/podcast/garyvee-from-earning-%242-an-hour-to-running-a/id1701718200?i=1000689595539  Leap Academy: Ready to make the LEAP in your career? There is a NEW way for professionals to Advance Their Careers & Make 5-6 figures of EXTRA INCOME in Record Time. Check out our free training today at leapacademy.com/training

Wow, this show is going to be incredible. So buckle up and I'm sure you're going to enjoy it. But before we get started, I want to ask you for a favor. See, it's really, really important for me to help millions of people elevate their career, fast-track to leadership, land dream roles, jump to entrepreneurship or create portfolio careers. And this podcast is all about enabling this for millions of people to see a map of what it actually takes for big leaders to reach success.

So subscribe and download so you never miss it. Plus, it really, really helps me continue to bring amazing guests. Okay? So let's dive in. We have over coddled inconvenience. People that try to make money to go on a beach and drink margaritas are always the people that do not make money. Gary Vee is back for a second episode.

This time around, he's taking us on a journey of building VaynerMedia into a multi-million dollar digital empire. You know, I think adversity is the foundation of success. I was the oldest, responsibility was my truth immediately. My life was not fucking fancy. I couldn't afford rent for my company, nor could I afford paying anyone. And I literally hustled my way into opportunities.

I do not believe you're allowed to love entrepreneurship for just the good stuff. If you really love this game, you have to be in a position where you're willing to lose. And if you lose, you must take 100% of the blame. I believe that most companies and most people are unhappy and lose because they don't. Gary Vee is back for a second episode. This time around, he's taking us on a journey of building VaynerMedia into a multi-million dollar digital empire. Gary Vee, for those who missed it, he's an entrepreneur, author, speaker, internet personality,

with over 44 million followers. In the first episode with him, we talk about his childhood, his family, and his career, how he got to where he is today. Now let's dive in. Gary, first of all, thanks for bringing us for the second time. Of course, it's lovely to have you. I'm really, really excited because I actually want to

focus him on how he actually started VaynerMedia. And I'm excited about it because a lot of our listeners are trying to figure out what's next in your career. You want more impact, you want entrepreneurship, or you want to figure out how to jump on to the leadership, but you're not quite sure what it's gonna look like. And Gary, you've done all of this. So I wanna take you back to probably somewhere around,

I don't know, 2009 and create a little bit of a blueprint, like a map for people. Because at that point, you already built the wine business. You already understood the internet is a big thing. You already built Wine Library, right, to what it is. And I think it went from what, 30 million to 60 million? 3 million to 60 million, or three million to 60 million. But now you have this decision, you're seeing something that maybe more companies will need this.

But a lot of people see things, but they don't jump. Can you take me to what made that decision? Take me to that time in your life. You know, I think adversity is the foundation of success. And I had accomplished my first goal in life, time in your life? I think adversity is the foundation of success. I had accomplished my first goal in life, which was to build a big business for my family. What I had not anticipated is, of 18 and really 22 to 34, spending 70, 80, 90, 100, 110 hours a week, every week,

for a decade to build a very large business for my father, who was a young man, I was 34, he was 56, and I didn't have any money, and I was starting to resent my father and I had just gotten married and I needed to start a family. And I had a brother who was 11 years younger to me that was graduating college who looked to me as someone who he wanted to do something with. So I had a lot of life events going on and I had skills and I had vision.

I did see that social media was going to eat up the skills and I had vision. I did see that social media was gonna eat up the world and become a major part of society, let alone marketing. You did. That I did, but I had no money. And so what I saw was an opportunity to build this agency and what had happened was I was just willing to be scrappy. And I was willing to be scrappy at 34,

which is why I struggle with so many people not willing to be scrappy at 22. And what I mean by scrappy was my life was not fucking fancy. Like, I don't know what else to say. Like, I paid my rent, I didn't take lavish vacations, I didn't have stuff, and I literally hustled my way into opportunities like the following. Ironically, just a couple hours ago,

I did a podcast for my friends Cass and Mike Lazaro. We're gonna see them in two hours. Amazing. So they were just here. Shoveling shit. Is their new book, and that's what we were talking about. I started VaynerMedia in the conference room of their company Buddy Media in 2009.

So I couldn't afford rent for my company nor could I afford paying anyone. So our first three employees were interns, all friends of my brother, but because it was spring of 09, the economy had just collapsed in 08, so all his friends that had jobs lined up lost them. So they were also scrapping.

And then I had a customer from Wine Library, who I'd known for a long time, who was in marketing. He had his own sampling company and they had a project and he was like, this social media thing, can I use that? I was like, yeah. So they paid us a couple bucks to help. And in those couple bucks, I'm talking $30,000, I used that money to get us going.

And I'm talking get us going like the money we paid for gas to go down to Campbell's for a meeting or, and what I did have though, was I had a little bit of reputation. I was known a little bit because the Twitter thing was coming and I started making content about marketing. And that content led to opportunities. Now, for everyone who's listening,

the way that social media works now is if you have no reputation and you have no followers, you can make one smart video right now about how AI tools work for marketing and that video can lead to your customers. That's what happened to me. And so that's who we were. We were a company that knew something was about to happen

and was using that medium to actually attract opportunity. So take me there. So you're basically asking Mike and Cass for their office, which is very bold and very, very scary. And very honestly, because I want to tell the story in truth, Mike and I met because an employee of his was fascinated by my content.

And we hit it off at our meeting he offered. Wow. Because he's such a mensch. And that's pretty incredible because they're not in a big spot by then. They have a small office. And at that point, they're giving you their... There's half the size of this, the context.

Okay. So that's your office when you get started. Now you decide if I'm not mistaken, not to raise capital. Correct. And we're in Leap Academy decided not to raise capital. But at that point, there's some money fears. Whatever you bring in, that is the salary. So take me to those moments. Did you have moments of, oh my God, I don't have salary this month? Or take me there a little bit to the beginning. I believe that most companies and most people are unhappy and lose because they don't think in terms of saving money.

The reason we worked was every time we got money, including that first $30,000, we spent only 15,000 of it. I wasn't hiring ahead of our capacity. I didn't care how long it would take me to build this company. I wasn't in a rush. So how did it go? I think that first year we did well.

We did like three or $400,000 and that was enough to cover my $180,000 in overhead and whatever T&E, travel and expenses and computers or just like stuff. But like we did not pay rent for the first 18 months of the company. We stayed there for six months and then there was a coworking space down in DeBrosa Street by the Holland Tunnel

called Sunshine Suites. They had this weird little non-office office and they wanted marketing and we bartered us marketing the space for room in this fake office. So by keeping my expenses down, the reason I never feared it is pretty quickly, we had months worth of runway, plus I still had some savings personally

and I was willing to dip into it. It's interesting because I'm sure you see it as you grow, the problems just change. It's not less problems. The problems are more expensive. Yeah, little children, little problems, big children, big problems. No, the problems are bigger.

And more scary because there's a lot more to lose also. Yeah, I think, little problems, big children, big problems. Like, no, the problems are bigger. And more scary because there's a lot more to lose also. Yeah, I think for some people, I would tell you that I believe the definition of a purebred entrepreneur is having a much better relationship with that fear than most humans. I'm really okay with losing it all. Oof, that scares me right now. Look, I prefer it not to happen.

I don't want it to happen. I don't do behaviors that would make it happen. But if it happened, it would feel as though it was because I deserved it. And you can build something great again. I think that's what you're saying. But not even that. Yes, I am saying that. But let me say something more important. I do not believe you're allowed to love entrepreneurship for just the good stuff.

If you really love this game, you have to be in a position where you're willing to lose and if you lose, you must take 100% of the blame. If I was to lose everything or get really hurt financially, that would be my fault and I'm willing to die on that sword. I'm willing to have the humility and the shame and the pain because I chose this course. But it's also really, really painful. So take me to the first time, and I assume there is a first time where you're like, oh my God, can I make this? Can I pay the rent? I mean, there's things that pile up.

There's lawsuits and people and complaints and whatever, like when you grow. Is there a moment where you're like, oh shit, this is hard? Not on the P&L part. Again, I'm too immigrant. I do not do things that could put me out of business. I think the things that probably have hurt

in growing a corporation is frivolous lawsuits have hurt. Being a good person and having good intent and just watching people use California or New York law. Oh God, we have this now. We're like, I want to kill someone right now. You could see how you reacted. You could see everybody how she reacted. When you're really not trying to do the wrong thing and people are basically scamming you by using law. And I don't mind to be scammed when you're being scammed by the concept of you're not a good person,

like the company, you know, like. But if you're actually trying to change the world and do good things, that sucks. Again, I don't mind if someone scammed me. I much, much more painful when someone scams you by saying you did something wrong, that they are just using a legal loophole. Like the sad part about America

is the way lawsuits work in this country. Like the amount of times my lawyer is like, I'd like to just settle this. I'm like, absolutely not. I don't care about the money. I am not letting someone create false claims and we will lose money on this because that's not nice. I don't care about the money.

So that hurts when people are doing those kinds of things. You know, look, it's lonely being at the top. I'm not an 11 out of 10 passionate for the way this day's going today. Oh, so we need to fix that. No, that's good. But you know what's funny? like me at an eight or nine feels like a zero.

That's how much I love what I do. But I can feel I'm at an eight or nine today. And I fully believe it's the weather by the way. Truly actually. Which is like really weird to me. I'm like starting to realize why people move to Florida. Like I'm like, oh I get it. Like I, but it was really interesting. I'm like, oh, I get it.

But it was really interesting. I've been thinking about it all morning. It's 1.23 p.m. right now. And there's days like this where I'm like, man, what would I be doing if I didn't have all these responsibilities? I thought about this literally today. I think when you're building something, every day has the potential to be hard,

even when there's nothing crazy going on. There's nothing out of the ordinary going on today. There's 13 fires that are going on, but they're all micro fire. I would say like twos and threes, which is small out of to 10. And yet I find myself like can't wait to it being seven o'clock tonight,

because then I'm gonna go to the Knicks game with my son and my brother, my two buddies. And I know myself, it's not the game that I'm yearning for. Usually having something like that actually makes the work day much more enjoyable, but I think this is important talk to everybody in the audience, which is what I think the game's about

is me getting through today. Having the tenacity, the grit, and most importantly, the ability to stomach uncomfortable days, I know what I'm feeling today is the thing that spirals people into negative places. I can feel it. My ability to contain it, notice the numbers I'm using, I'm using them very specifically. My eight or nine out of 10 is what people would consider a one or zero. I'm depressed today.

I'm anxious today. I'm depressed today, I'm anxious today, I'm unhappy today. I'm trying to think through every day as a human and a public figure who communicates things with the hope that it brings value to people of how to get people into a place of getting comfortable with not being comfortable. Your question. The answer is potentially every day. The answer to your question of tell me a time,

maybe every day if I do not do certain things, we will run out of money and it will go out of business. So how do you wake up in the morning and how do you know? The same way that a parent wakes up every day knowing that they're a mom and dad forever. Have you ever seen an 80 year old parent and a 60 year old like in public? It's fascinating.

Like you're still a mom and dad forever. The same way that somebody much less fortunate than me, how do I do it? By perspective. Even people woke up this morning and lost a loved one last night. Many. Do you know how crazy that is?

Like I say these things because I wanna really get people to think like, thousands of people in the last four hours since this tough weather day for me, thousands of people have had the most catastrophic thing that could happen to them in the world happen, the death of someone in their inner circle. So I really struggle with, yeah, I'm having a challenging day, but this is what I think has led to a very big issue in our society. We have over coddled inconvenience.

We have weaponized things like a tough day into things that we just need to be stronger. How do I deal with it? By knowing I have no choice. So let's go there for a second, because entrepreneurship is very, very hard. And there are going to be moments, if you will, that are not bad weather, but they feel like near-death experience.

They might not be, but they feel very real. Take us to one. I've never had that. You never have? I don't want to bullshit you because I don't care enough. I don't care about my businesses enough. I want to be very, very transparent with you. I only believe that truth brings the most value to an audience.

I have never felt anywhere close to that when it's come to business. What about layoffs? Because they can hurt. That crushes me. See? But that doesn't feel like a near, you know what I mean?

I want to be. I get it, I get what you're saying. The hardest thing for me definitely has been the interpersonal things and my lack of candor has, in my early part of my career and the dominant part of my career, has actually led it to be way more challenging. It's amazing.

For 20 years of my career, by not being able to tell employees that they're not doing a good job along the way, led to the firing being very hard. Now, because the company is doing a much better job with critical feedback, it is shocking to me how much more comfortable I am with people getting fired. I didn't realize this, I couldn't see it.

Now I feel like we're doing enough of the right thing by people that we're not surprising them. Before I thought I was doing the right thing by not scaring them day to day, but in essence the ultimate thing was happening which is I was surprising people. That's been a huge wake up call for me. I think the interpersonal stuff is, I'll be honest with you, what's even harder than that is I get from HR every day notes if somebody has lost a family member or is dealing with

something traumatic. A miscarriage, a house burning down. notes if somebody has lost a family member or is dealing with something traumatic. A miscarriage, a house burning down, that's tough. We call it pet people experience esteem instead of HR because I didn't realize HR had a bad brand so I don't want to call it HR at Vayner. I told the pet team the other day, I'm like, I might stop getting these

because it's just fucking depressing. Johnny's like, Johnny Thompson's aunt died, Ricky Thompson had a car accident, Sally Magoo had a miscarriage, it's like, fuck! You know, like, the human part has weight, especially when you're an empath. So yeah, that's been challenging. If you're feeling stuck, underpaid or unappreciated, or you're simply ready to take your career

and life to the next level, I have the perfect solution for you. We have a program that helps you fast-track and leap your reputation and career. Become the best version of yourself. Get the dream role you deserve, move up to leadership, jump to entrepreneurship, or even build a portfolio career. This program helps hundreds a year, and it will help you gain the income, influence, and impact that will transform the second part of your life. Watch our free training today at leapacademy.com

slash free hyphen training. The link is in the show notes. Now back to the show. Talk to me for a second about the balance between being transparent with your company or with the people around you and actually freaking them out if there is a fear. There's a real balance to it. That line from Jack in that movie, you can't handle the truth, is the number one truth to employees. Employees talk about wanting transparency.

It's not true. It took me some time to find that out by the way. Most of my friends that are overly transparent, I was saying that to them 20 years ago, there was that whole movement of transparency, especially coming out of Silicon Valley. I'm like, this is not real. That's true.

In the same way that companies can't take political stances. I mean, that was so humorous the last five to seven years. Like, there's not a single issue in the country right now that 50% of my employees don't see it one way and 50% see it the other way. So, and by the way, my company is not a human being. I'm a human being, I have political views, but my company is not required to put out a statement

on every rally or Supreme Court judgment. What are we talking about? So, transparency is very laughable. People are completely full of shit on this issue. We want transparency that's convenient or feels good to us. Or if we want to get to the part that nobody wants to actually say out loud, you want transparency because you want to cast judgment on others. I noticed that people that call for transparency are really also very big on privacy

and don't want their shit out there. I try to find a balance and I do think there's balance. I also don't think holding everything and not telling your company what's going on is a problem. But I think about it all the time. And I think my leadership team has learned a lot from me on this issue because I do think a lot of them over the last five to seven years when corporations got socially more liberal, they wanted me over coddling and over transparency in places where I think

ultimately they've learned that it was great that we didn't. In a place where we're very good at over coddling and we're very good at being overly transparent. There's lines in the sand that if you cross you actually create much more damage. That makes sense. That's interesting because I did come from the Silicon Valley, be transparent, be transparent, but then everybody freaks out.

I'm like, where did you go? Yeah, I learned my way. But talk to me a little bit about some of the ways that our listeners, if they're going through hard moments, looking for jobs, getting rejections, debating what's next, how can they motivate themselves? I get 100% of my motivation from gratitude. When you were asking that question, I was going through my brain of like, what do I do?

I really want to give good answers here. What do I do in times of trouble, in times of pushing through? And I always just go to gratitude. It's why I was able to answer to you why I don't fear on the business stuff. I go so basic on the health and wellness. Notice my analogies. I can't be upset because look what happened

in the last four hours, people lost love. I go there, that's all I've got. Health over everything. None of this matters. If I lost all my money and had unlimited ridicule as a public figure for not being as good at business as I thought I was, I wouldn't care. How does it not hurt you? How do you create a thicker skin?

By realizing that anyone who, let's say it all crashes and burns. Let's use you. Oh, and burns. Let's use you. Oh, darn it. Let's use you in my crashing and burning. Okay, no, I can crash and burn for you. No, no, no, I'm with you. Let's use it. You wake up in 16 weeks and you read headlines, Gary Vee has gone bankrupt, all the companies went to zero,

he over leveraged himself, all this stuff. My intuition, in the limited way that I know you, is that your first move of action would not be to go to Twitter and be like, ha ha ha, Gary Vee, I knew it. No, I'm like, let's partner, dude, I have some ways to make money, let's go. You understand? Yeah. How do I deal with it?

I have so much empathy and compassion and sympathy for humans that would go on the internet to cheer on my grief. Their lives are in such a bad place. That is true. That I can't conjure up the feelings to be upset for myself in a world where I know even if I went to zero, I would never do that to someone else.

I'm too grateful that my mom built me this way. I'm too grateful that I don't have that poison, that envy, that jealousy as a currency through my life because I do not value the opinions of losing players. That's why. Let's talk for a second about your mom, because I think that is a big motivator for you, for the dream of buying the debts. Talk to me a little bit about that. Making my parents proud is my North Star.

No question about it. It's very obvious to me at this point in my life. I love them so much. I'm so grateful for them. They sacrificed so much to start our family journey in this country. My mom did a remarkable job parenting me. My father worked so many hours so that my mom could stay home and parent me at a time where we had nothing.

And I've lived my life giving back to them. And then after that felt fulfilled and I needed to do something else, I've lived my life trying to make them proud. And it seems like it's still there. Like, so talk to me about Jets specifically, because you also have a beautiful story about it. I mean, the Jets, the story for everyone who doesn't know is,

I'm a huge New York Jets fan. I fell in love with them as a child in the suburbs of New Jersey. New Jersey is right across the river here. I wanted a Jets jersey. We couldn't afford it. My mom knitted me one. Somewhere around fourth or fifth grade, I created this fantasy of I was going to be such a good businessman that I was going to be a person that went from not being

able to own a Jets jersey to owning the entire team. And it has been a great, fun, ambitious goal of mine my whole career to buy the New York Jets. And if things go well here for the next 20 years, I think I'll put myself in a position to take a stab at it, and it's kept me busy, right? But honestly, I think it's important for me to clarify this for my biggest fans. I couldn't be more detached from that as well. Like if God forbid, and I'll use God forbid, somebody else buys them, not me,

then I'll try to buy the Knicks. Like it's not that serious, but it has been a goal, and I'd like to do it. I'm trying to do it. And yeah, I think it is a very emotional thing to me and definitely started from a place of a mother's love. Which is so special because I think there's something about the vision of putting that knitted shirt.

So I still have this little sweater and a fireproof glass box and I wanna put it in the stadium, and I wanna plaque to say, from not being able to afford a jersey to buying the whole team. I like inspiring people because I get inspired. I think having something to look up to

and things of that nature, I think is really important for people. You talked about earlier, what drives you, what drives people. I think we're all driven by different things. But I think many of us as human beings are motivated and driven by people that achieve certain things. And I'd like to be that for someone.

I truly believe it's inspiring, but I think it's also inspiring to see somebody that is not afraid to speak a vision slash a dream because you almost speak it to reality. And again, you're detached. If it's not gonna happen, it's not gonna happen, but you're not afraid to speak it up. And I think a lot of us are afraid to speak our dreams because what if they're not gonna happen?

I mean, I'm an incredibly successful human being, but for, I have spoken it so up that most of my fans will think I failed if I don't achieve a 0.0000001% crazy thing of buying the New York Jets. But this goes back to judgment. I believe that the currency of my life and the currency that I see in other happy people

is the ability to live within their cocoon of their life, have good intent for others, and be able to deal with bad intent from others. Ooh. The reason I do all these things is I'm invincible. You know that, right? Yes, and I'm trying to attract some of that. Give it to me.

How do you build that feeling of being? Look, I take very little credit for it, if any. Luck of the draw, DNA wise. Like, DNA is the thing. DNA is real. Like, I'm sorry, it is what it is. Some people have great hair. Some people are athletes.

I was born a certain way. I then was born that way from a human who ended up being my mother, who was that way, who then also formed me. Not only did I take my mother's attributes, she then molded me. My sister is three and a half years younger than me. I watched my mother mold her very similar to me.

She didn't have the same DNA, different outcomes, different circumstances. We had different life circumstances. I was the oldest, responsibility was my truth immediately. My sister was coddled by me and my mom. Like life. So how did I become that way? A lot of it had nothing to do with me.

Now, what I would say is, at some point we all grow up. For everyone who's listening, who's like, my dad was a narcissist and my mom was insecure, like screw you, Gary. At some point you become 18. At some point you, Gary. At some point you become 18. At some point you become 20. At some point you become 22. If my mother was sitting here, she would say,

you're being too humble. That's all nice and dandy. But then these are the things you did in your late teens, 20s, 30s that were built on that foundation, but you did them different than I did. You pushed against me on this, you did this, and these outcomes happen because of it. My biggest question to everybody is

when do you stop blaming your parents? When are all of you gonna grow up? What's the right age to say, this is what my parents have done wrong, but I can go to therapy, I can start working out, I can start reading different things, I can start surrounding myself with different people? I, when is that?

Is that 16, is that 18, Is that 22? Is that 25? Is it 30? Well, if it's not getting you closer to your goals, it's completely irrelevant. And the only goal should be peace of mind. The only goal that everyone here who's watching should get to is living a life where you do not have stress on your chest.

And that is achievable. Here's why. The wrong stress, because you have a lot of stress. Correct, but my stress is really... But it also makes you happy. Correct, that's like playing sports. There's three seconds left and you're losing by one and you're nervous, but you're also excited

to take the last shot. All my stress, to your point, is good stress. There are people really, really anxious out there and it is completely framed up by a lack of accountability and a lack of perspective. People can change and I spend time thinking about that. But let's talk for a second because I think it is important because there are people that are building companies and the mental stress or the mental anxiety is taking them down.

Because their identity is wrapped up in the success of that business. I do not view myself as Gary Vee, the entrepreneur. I view myself as Gary Vaynerchuk, the nice human being. In my soul, my validation to myself, the way I judge myself, because we all judge ourselves, is do the people that know me think I'm a good human being? Yes, and you still decided to be the nice human being that doesn't sit on the beach all day drinking margaritas.

Because I love the game. Because I don't know what else I would do. You know, like. Sit on the beach and drink margaritas. Yeah, not, by the way, I know that people want to do that. That sounds, when you. I would go nuts, but I'm just. You just took the words out of my,

like when you just said that the second time, I would die if someone said to me that I am forced, some weird genie landed right here right now and said, Gary, I'm taking your hand, everybody will be fine. Everything will be fine. I am taking you to a beach and you are going to live there and eat well and exercise and shit, I would die. I would say, fuck you.

I don't want to do that. I do not want to do that. To me, I'm a builder. You know how some kids sit and build Legos for nine hours? I don't want to do that, but I understand those fuckers. I'm like, I do a version of that. It's called this. I'm a creator. I'm a communicator. I'm of that. It's called this. I'm a creator.

I'm a communicator. I'm an operator. This is my joy. I could not imagine working for someone. I could not imagine not doing anything. People that try to make money to go on a beach and drink margaritas are always the people that do not make money.

I wanna take you somewhere a little different. You spoke about Communicator. We are very aligned on personal branding. Obviously, you took it to a whole different level, and we literally try to teach people how to create their personal brand and how to elevate their careers through that, and how to create portfolio careers like multiple streams of income, which I believe is a future work.

But I think it's important for our listeners, one of the dilemmas that they're going through is if they're right now working for an employer, they wanna balance this correctly to not- Which is fair. Nudge them in the wrong way, which is very fair. What is the right way for people to still build their personal brand,

but without ruining something or risking their own career? By dealing in reality, which is the real answer to this question. If your company does not allow it, I mean, you can quit, but like, I don't like to talk in fantasy. Like if your job's policy is you cannot make professional content

because you're an employee of this company, which is a lot of companies, not because some companies are bad, some companies have heavy regulation. Some companies don't want their employees gaining leverage and going to other places. Then that's that. But I still think for those people, you can still make a personal brand around your interests. So if you're a financial advisor at a company that has a strict policy, you can make content around skiing, wine, and golfing, which lead to interests of the kind of high net worth

individuals you're looking to get. So there's a lot of hacks. And then I think for everybody else who has freedom, the way you do it is you don't tell secrets from the company. Like, I get these emails, they're like, Gary, I can make content, but I'm scared because what if I get fired? I'm like, then don't post information

you're not allowed to talk about. Like, you know, like talk in theory. I talk a lot in theory. I talk in a lot of analogies. I say things like my client, not Pepsi told me to, you know, like, so I think it's about being smart and drawing within the lines that you've been given. Well, a lot of our listeners are also right now

at the executive level, at the C-suite. If you're speaking to them, how should they help their teams and empower them to grow? Are you talking about growing in overall or are you talking about growing in the concept of personal brand building? Their personal brand, but also leadership and growing personally within the company.

Best way to get an employee to grow in your company is with honesty. By telling them what you honestly think about what they're good and not good at. And finding balance. I think everything is purple. Not red, not blue. You know, if you tell your employee

everything that they're great at, but you don't give them critical feedback like I did, that created that problem for me. If you're like my dad and everything, you'd never talk to an employee unless you were yelling at them and telling them what you're doing wrong. Well, that didn't work for him,

which is why my career went the other way and I overreacted the other way. The place that's awesome is the middle. Kindly, gracefully giving critical feedback and helping people understand the game that they're playing. What's the politics of the organization? What's the skill set?

Things of that nature. And also really knowing when to give roses. And really, I think giving roses is very important and positive reinforcement. And if those executives want their teams to allow a little bit of personal branding, but without obviously crossing the line. How would you coach these executives to say, this is something that your teams can do, maybe this is-

Resources, bringing in speakers, buy my last book, Day Trading Attention and give it to all your employees, signing up for your stuff, like resources. Putting them in a position to succeed, putting them on third base. So maybe last words for our listeners, again, they all want more, they want,

and again, more is different, right? We just talked about it, right? For some people, it is, you know, more impact. Some of it is legacy, some of it is generation well, some of it is making a difference. Like it's good looking. Can I say something on that? Yes, please.

And also allowing yourself the grace to realize you're allowed to change what you're going for. Exactly. That earlier thing that I said, the people that want margaritas on the beach are the ones that don't get it. A lot of people on the other side said, you're wrong, Gary.

My friend Don worked for 30 years, made a lot of money, retired and drank margaritas. That's not what I was saying. What I was saying is, if Don had wanted margaritas on the beach when he was in his 20s, like so many people want to do in retirement, he would have never gotten there.

Don wanted to hustle, and then Don at 59 was like, you know what, I'm good. Do not underestimate one day me waking up and just telling the world I'm good and I'm going into that phase. I'm also equally say out loud all the time that it is 100% that I'm gonna die at my desk at 93. And let me tell you why.

I know I have the capacity for both. I equally in my body have the ability to do this forever. But you know, look, back to my parents. When my parents pass, it's gonna happen, unfortunately, and please God they should pass before me. That's the life cycle I don't know how I'm gonna feel I might be affected by that given how close I am with them I don't know what's gonna happen in the world. I know losing my mom changed my life. Of course it does It's one of the most important chapters in a human's journey. The death of your parents and the birth of your children,

if those things happen in your life, are the things. Everything else becomes incredibly secondary outside finding the love of your life. I mean, you're talking about like, there's levels to this game. So I guess what I wanna say on this part to everyone that's listening is you're allowed. Give yourself the grace to change your mind.

You were going for money, good for you. You're allowed. That's something people do. Oh, you made some and you scratched that itch and you realized you got a divorce because of it because you were too money hungry and you didn't give enough time to your spouse and now you fell in love a second time.

Well, maybe this time around, it's okay that you got, everybody's putting themselves in these boxes as if we've signed in blood of who am I? I'm fucking different tomorrow than yesterday. Life is in phases. And that's the beauty for us, as you start to live another decade, another decade, that truth becomes even more clear, right?

And by giving us grace to change our mind, we don't box ourselves in. Do you know? Please. But here's what I love. Because once you decide on the phase that you're in, all that we're saying is that be intentional, strategic about it.

Because stop fighting what society thinks, what other people thinks. Decide that this is your phase. You want to make money? Great. You want to make impact? Great. You want to grow your career in titles?

Great. Whatever it is, you want balance? Great. You want to make impact? Great. You want to grow your career in titles? Great Whatever it is you want balance whatever drink margaritas But just decide and start being intentional and strategic about it and execute That part I see a lot of people making great plans being pretty intentional This goes back to like being in the gym The part in that rant that you just made that I loved where I see so much breaking down is people do not have the grit to execute against their ambitions. Stop being full of shit is what I'm basically saying.

Like, I just think that people are wildly entitled. When I hear your energy, I'm like, you must know that you are signing up for hard. Nothing feels better than when you accomplish something that was hard for you. There's nothing that feels better than when you prove something to yourself. Nothing.

I think we need to start talking more about tenacity and perseverance and grit. It is really a lost conversation. The most important one though. It's really important. People. The most important one though. It's really important. Like people are unhappy because of that being eliminated from the equation, I'm telling you, that's what's happening.

Gary, you're amazing as always. Thank you. And I can still talk to you. Like I feel like we just started, but this is so cool. Thank you for bringing us to your home. Thank you for being here again. Thank you for bringing us to your home and everything. Thank you for being here again. Thank you. I hope you enjoyed this as much as I did. If you did, please share it with friends.

Now also if you're feeling stuck or simply want more from your own career, watch this 30 minute free training at leapacademy.com slash training. That's leapacademy.com slash training. See you in the next episode of the Leap Academy with Ilana Golanshchuk.