Creating Confidence with Heather Monahan - The Secret to Feeling Confident Walking Into Any Room with Gary Vee

Episode Date: May 6, 2025

Want to know how the most unapologetically confident think? I’m bringing back my episode with the one and only, Gary Vee. He shares incredible insights about chasing your dreams, why success isn't about money but about happiness, and how to stay true to yourself in a world full of noise. We talk parenting, entrepreneurship, and how to turn your passion into your purpose - with zero excuses. If you're ready to be inspired, challenged, and motivated to level up your life, this episode is going to light a fire under you that you won't forget!  In This Episode You Will Learn Why most parents are raising entitled kids (and how to actually set them up for success.) Gary’s formula for leadership, personal growth, and emotional freedom. What to do when your passion doesn’t match traditional success. How to negotiate your salary with confidence. Resources + Links Sign up for a one-dollar-per-month trial period at shopify.com/monahan Download the CFO’s Guide to AI and Machine Learning at NetSuite.com/MONAHAN. Want to do more and spend less like Uber, 8x8, and Databricks Mosaic? Take a free test drive of OCI at oracle.com/MONAHAN. Get 10% off your first Mitopure order at timeline.com/CONFIDENCE. Get 15% off your first order when you use code CONFIDENCE15 at checkout at jennikayne.com. Call my digital clone at 201-897-2553!  Visit heathermonahan.com Sign up for my mailing list: heathermonahan.com/mailing-list/  Overcome Your Villains is Available NOW! Order here: https://overcomeyourvillains.com  If you haven't yet, get my first book Confidence Creator Follow Heather on Instagram & LinkedIn Gary on Instragrm: @garyvee

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Go to bellvatal.com, code BV15, that's bellvatal.com. This is going to change everything. I think it's really important to highlight this. We're all coming at something from our past experience. What we can stop in that moment and do instead is come at it from what our future may be and look to see what it may be and open our minds to thinking differently.

And if you listen to your kids, they're gonna give you insights to what the future can be. Absolutely. And this is a very powerful parenting tip. Every parent is judging their kids based on yesterday, but your kids are living in today, which is a better indicator of tomorrow. I'm on this journey with me.

Each week when you join me, we are going to chase down our goals, overcome adversity, and set you up for a better tomorrow. That's the notion of it. I'm ready for my close-up. Tell me, have you been enjoying these new bonus confidence classics episodes we've been dropping on you every week? We've literally hundreds of episodes for you to listen to, so these bonuses are a great

way to help you find the ones you may have already missed. I hope you love this one as much as I do. Welcome back, everyone. I'm so excited. This is my first show and I go big or go home. So my first guest, I'm so excited to introduce you. You already know him, you know him and love him. It's Gary Vee and a brief bio for anyone who might not know. I hate the one Trouty sent me so I'm gonna go off

what I think. He's the chairman of VaynerX, he's co-founder of Empathy Wines, which we're so excited about. Co-founder of VaynerMedia. He's an international best known for his speaking, his writing, best-selling author, five New York Times best-selling books.

He is a social media phenomenon and mentor to millions and overall badass. So I'm so glad to have this time with you today. Thank you. Thank you so much. Yeah. All right. So I want to start today.

You know, this is interesting because I'm looking at the show around how do we create confidence for ourselves and others and diving into some of the hard times in life and how we bounce back from them. Just so you know, I reached out to your team and I said, guys, your team's amazing, by the way, and I said, guys, I need your help. Help me dig into his past, and let's find some times he struggled with confidence. That must've been hard.

No, you're gonna love this one. This has happened to no one. Heather, we spoke to his family, we spoke to all employees. There aren't any times this man has struggled with confidence, is that true? employees, there aren't any times this man has struggled with confidence, is that true? You know, I would say outside of the sixth to like 10th grade window around singularly like,

am I starting to like girls and do I have the confidence to like ask them out is really the only even resemblance of anything, here's what I've done, and this is super interesting, where you just took me with that question. One of the things I'm most proud of is I talk about only things I know. One of the reasons I'm improv, one of the reasons,

I mean look, we're doing this podcast, you can see I'm trying to run the company seconds before we sit down, I'm trying to be cordial, I felt bad because I have fires going on right now. But you're sitting here, we had a few minutes before we started this, and I'm like, shit, let me put this down. I wanted to be nice, I don't want to be that, right?

But I can go on in a second, because I will only talk about what I know. It's the same answer to what I'm about to tell you. I have basically only done things that I love and I'm good at, so it's super hard for me to lack confidence when I'm disproportionately passionate and disproportionately capable of the thing that I'm doing at all times.

Plus then I'm also really, really good with people and don't overvalue their opinions. And so, look, everybody has struggled with confidence, but like, one of the reasons in that investigative reporting that it's been tough is I've, no question, I've now come realize I'm a little bit of a unique kind of dude and I think there's strengths and weaknesses in that.

You know, like I've never experienced skydiving because I'm like I don't like that and I don't wanna do that. Like you know, there's a lot of things that are limited about me. But it's also the reason that that was the answer and I think the overarching answer, I just touched on it is,

one thing I can tell you is you will be hard pressed to go through life and find many people as deeply insular as I am. I am remarkably incapable of getting too high on people's positive feedback or too low on, I'm just in this deeply weird zone of like, it is what it is, I have super good intent, I have zero expectation of others,

I have no entitlement that I deserve anything, I am just in this very interesting mind zone that I am so grateful for now that I've come to realize it as I've lived and been about. No Addy, just Grady. It was, you know, it's really funny about that and thank you for noticing that. I posted it yesterday.

Like, it is remarkable that so much of what everybody aspires to get from meditation, from medicine, from self-health, like from all these things that 99.999999% of people are trying to get to this place through these things, my mother and my circumstances and my DNA and my father and my sister and my circumstances and DNA and my father and my sister, my circumstances and DNA, and so I'm so grateful for this zone I'm in,

I'm really, really confident. I really am. Have you always felt that grateful? Yes. Wow, that's amazing. Let me rephrase. I always, I didn't know the word was grateful. I always was like, I was super in love with my mother.

You know, like, because I knew something good was going on. I was super, I, I, never complained. Never. Like, just don't have that gear. Can you start working with children more, please? I, listen, what do you think I'm up to, right?

Like, so much of what drives me today is the fact that there is an enormous amount of 13, 14, 15, 16 year olds that think I'm cool because of Instagram, and I am secretly so grateful for the opportunity to like form some of their opinions. Absolutely. I really am.

A woman the other day tweeted yesterday that she took a screenshot of a text message with her and her son, and she said, finally, finally, finally, somebody's penetrated my son, and I can't tell you how good it made me feel. The overarching theme to me is more than the gratitude, is that you're leading this purpose-driven passion life,

which so many people do not live in. So many people go to work to chase a paycheck, or because this is what my parents told me to do, or you know, so how did it end up? Was it by chance that your dad started the wine library, and you ended up just loving wine, and sales was there? How did those dots connect? They started in fourth grade, I believe,

when I decided consciously, off of intuition and feelings, that I didn't believe in school. And that I knew, think about how young you are. You know, hang on a second, this is frustrating as a mother because I'm an 11 year old and I'm all about you encouraging these kids not to complain. However, it's dicey when you start saying, I wanted to get out of school

and school's not for everyone. It's dicey if you hold the institution of school being on a pedestal. And I think that's fine. I want none of my opinions to be anyone else's opinion. I want to share my opinions that I've lived or I've observed very closely and want to talk about them.

I get 10,000 DMs a week from children 13 to 20 saying things that they would never tell their parents. And so when I say things about, hey parents, you're buying your daughter a BMW because she's begging for it, but she's telling me behind the scenes that I hate my parents for making my life so easy. Now that kid's talking out of both sides of their mouth,

but they're a 15 year old. And so like what's the decision making process? That is an unbelievable conversation. We have a whole generation of parents shitting on millennials, but they're the ones who raised that entitlement. You know, I think of it as enormous self-esteem building in parallel with radical candor and lack of entitlement.

And that's what I think my mom did. She told me I was the best, but when I went 0 for 4 in a little league game, she didn't blame the umpire or my coach. She said you weren't good enough. It's leadership by example, I mean that's all it is. You know, but it's very rare in our society today because parents want to build self-esteem,

but what they actually did was build entitlement. And kids got soft. And we're collectively soft because we didn't pay the piper and have a recession in 2009. Everything is materialistic. We all care to keep up with the Joneses. Everybody's valuing everybody's opinions. Opinions are flying heavier

and more black and white than ever because of social media. And we've gotten into this massive cocoon of everybody's listening to every voice but their own. And then when some people tell me, well Gary, my voice says I suck, I'm like that's not your voice, you've taken on the voice of someone else.

Lady Gaga said something yesterday on social because she crushed the Met Gala and she said something like, I once had a boyfriend who told me I would never be famous, that I would never win a Grammy, then nobody, did you see this? And she said, and I replied to him by saying, one day after we're broken up,

you're not gonna be able to go to the deli without hearing my name or seeing my face. She put it out into the universe, she owned it, and I showed that to my kid, that's so funny, you just brought that quote up. And I just so understand that. I was told by the system, by my report card, by the friends, parents, by my teachers,

by everybody that I would be a failure. D's and F's, you were gonna be a failure in life. The only voice I listened to was my own. Instilled by your mom. Correct. Through self-esteem, I'll never forget it. Opening a door for an elderly woman when I was eight years old at a McDonald's,

I can see it now. Oak Tree Road, Bradley's, Edison, New Jersey, 1983, maybe 84, before November, opening a door for a woman, sunny day, and my mom went off as if I won a Nobel Peace Prize. She instilled positive reinforcement around a very good behavior. My mom also punished me on every report card. She punished me consistently through high school.

No Nintendo, no TV, no phone, no friends, no going out, all the way through my senior year of high school. Even though I was proving to her that I was capable, sports cards, helping my dad's business, she held me accountable. I was still a her that I was capable, sports cards, helping my dad's business, she held me accountable. I was still a student and I was failing at school and thus you should pay the price.

That accountability mattered. A lot of moms and dads are overacting the other way. They decided entrepreneurship is cool, their kid's getting F's and they're like, hey, you're gonna be an entrepreneur but what I'm worried about is they're creating entitlement. And so this tightrope of self-esteem building while being accountable is remarkably difficult.

And then, back to the sixth to 10th grade of like, I like girls, but I'm scared to ask them out because I don't want rejection. I also didn't conform to peer pressure, ever. And that was because I just couldn't hear anybody else's voice. I couldn't hear anybody else's voice but my own. Well, there's no way you would have been able

to get to where you are today, specifically from the social media standpoint, where there are so many haters, there's so much negativity and attack online that you developing this authentic confidence has got to be one of the reasons why you could get here. You know where it comes from also? Balancing it with empathy.

Let me give you my perspective on when I read something that says, well, you're a crackhead, Gary, or you're a charlatan, or you're lucky, or your daddy gave it to you, when they don't know the story of what I actually did at Wine Library. All those things penetrate first level hurt. You know, nobody wants to hear it.

But immediately my place doesn't go into, I'm confident, fuck you, my place goes to, man, thank you God for not letting me live a life where I would actually take the time to spend and consume somebody's content. I don't even consume anybody's content to begin with, let alone consume with the interest to tear that person down. You have to be so unhappy inside

to wanna manifest tearing somebody else down. And I, listen, I don't like talking about this, but this is your first episode and I wanna give you something. Thank you. I meet a different guest each week. I don't know what to tell you. Confidence clear.

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Awaken the strength, power, and resilience already in you with the first and only supplement clinically proven to rejuvenate health at the cellular level. Timeline is offering 10% off your first order of Mitopure. Go to timeline.com slash confidence. That's T-I-M-E-L-I-N-E.com slash confidence. I ask you to try to find your passion. My grandma was remarkably negative. You know, she has dementia now, she's been in essence gone for five to seven years,

but she's been gone to me for 25 years because she was the singular most negative person I'd ever come across in my life. And the reason I checked out from her at 16, 17, 18, whenever I did, was because she spent 100% of her time tearing down other people. My father, my mother. It's your father's mother.

Yes, my aunt, my sister. She's your father's mother. Yes, my aunt, my sister. She tried to do it to me, but I was like so in a, like you know, she gave up on tearing me down I think at some level, because she could sense that I didn't give a fuck. You know, but nonetheless, I'm disproportionately optimistic and positive, but I live, my grandma spent her whole summer with us.

Every summer. So how would you create boundaries to protect yourself from someone like that? I couldn't hear her. But other people can. How did your sister do it then? She did it. Do you understand?

That stinks. It sucks. And so like, what people don't know is everything about me. Cause I don't share everything like I just shared with you. And the reality is like, I've seen it up close and personal. I know the extreme positivity, I know extreme negativity. Not only was she a disproportionately negative person, she lived her adult life until she was my age right now, 43,

before she moved to America. You know, and like lived in Soviet Russia. She was a widow with a 15 year old. Like she had shit. She had tough life. She like was widow with a 15 year old. Like she had shit. She had tough life. She was a child in World War II. I don't judge her.

But I also understand what it is. And I understand why my dad is the way he is because that was his framework mother. His environment was the Soviet Union and that mother. Mine was America and the coming of age and my mother. So I'm grateful. How did your dad and your mom get together? Because they sound really different.

Sometimes opposites attract. And you know, and my dad is amazing in a lot of ways. But he will look at the world negative. My dad starts with no. I start with yes. That's a very different way to see the world. Are they proud of you now, your dad, specifically? My dad and I are outrageously close.

And my dad, you know, just because he starts with no, or just because he had a negative mom and because he's negative, doesn't mean there's so many, I mean my dad is ridiculously loyal, outrageously proud. No, you know what I, let me tell you what I mean, my dad. Please, please. I wanna do a better job with this question. When I wrote my first book,

some people in my family were upset. They don't like hearing about inside your life because it was inside our life in the past. You know what's funny? I think my parents, well first of all, my mom, I've literally made her out, like my mom loves her.

Oh, she worshiped you. Well she worshiped me from the get. She lost her mother at five. Her dad went to jail when she was a kid, like for 10 years. She had a tough life too. Way tougher than my grandmother. Wow, interesting.

Thus as you can imagine, it's very hard for me to accept people blaming their childhood when my mother lost her mother at five and lost her dad for 10 years to jail when she was a teenager and like, who raised her? Came a stepmother who wasn't thrilled about it because she was just devastated

from losing her new husband to jail. And then she came to America and was poor and she worked every day of her life, went on zero vac, my mom and I went on two family vacations, like my mom never complained a day in her life. Her life is shit compared to 99.999% of people that come to me with complaints. It's hard for me to get going to accept your complaints

when that's my mom's life and it's right in my face. Forget about my life, which had its hardships, but like not compared to most, or just in the mix. You know, like, my mom's the most positive, like amazing, like I'm a byproduct of her. So what do you think that is, a choice? DNA is big. Chemicals that were put in her,

because she didn't decide at five years old to be like, fuck it, I'll face this disaster. I think chemical's real. I think chemicals are real. Look, this has been figured out long before us, like DNA and environment is real. DNA is crap shoot. Environment gets into an interesting game.

It's also crap shoot, you don't pick your parents, but what you decide to listen to and whom becomes a very interesting debate to me. One of the things that I'm very proud of is I am the practical positive reinforcement in a lot of people's ears right now, and I take that very seriously, and it really makes me happy,

because a lot of people don't have the luxury of having family that is cheering them. You know, most people have family that's booing for them. Misery loves company. Most people want to tear down everybody else's building to make theirs feel bigger. You know, it's very rare to have pure, practical positivity being pumped into the ecosystem, hence why all the attention I have,

and easy for me not to get high on my supply, because as you can tell by this conversation, I view that as a cosign to my parents and my circumstance. I'm not special, my parents are special, my circumstances were special. I'm just living out the circumstances. Do you ever get afraid, and this is kind of off topic, but I'm thinking about you being special,

first of all I think everyone's special, right? So in their own unique way. They are. However, you've created this real strong forward-facing personal brand first. I think of Gary Vee first before VaynerMedia, right? Question. Of course.

You and everybody else. Before Empathy Wine. You and everybody else. So do you ever get worried from a business perspective, am I so big that what if I get knocked off by a bus tomorrow what happens to the company? No.

What does happen? It folds. Or they rally and decide to keep it afloat in the honor of their fallen leader. You never think of that. No, because it's a silly thing to think about. It's interesting to me. It's an ideology.

First of all, it's selfish. Like, I'm dead. Why would you want to set your people and your teams up for success? Not the company, them. F*** the company. I care about them. Do you know what happens to Dustin?

He writes a blog post and does his story of what he remembers about Gary this one time he said this thing to me, posted on LinkedIn, and 400,000 people asked him to be on their personal brand team. This is where I'm unbelievably selfless. I don't care about my company. I care about the human.

You like it? Crazy, right? It's shocking. I've about the human. You like it? Crazy right? It's shocking. I've been in corporate America my entire career into the last year and a half and I will tell you, I have never once seen a chairman or a CEO come from business at that perspective and I think that's unbelievable.

Cause I actually think it's also practical, not just altruistic. I've died. I'm not gonna care. I don't know. I literally don't know what's happening. It's over. It's a wrap.

What I've done is I've built such a progressive, forward-facing personal brand that the collateral on my employees is remarkable. Do you know what's going on right now? My people are getting offered all sorts, like especially for Team Gary V, these two characters, like they just have options and that makes me happy. Kenny just left the team.

He got a great gig in California. Now, I think it's super great here that people are naive about and I think that, you know, I'm a uniquely kind of interesting character and I make it look a lot easier than it is and that will either play out or not for Kenny but he's now family and I think I've done, that's what the best part of what I'm doing is.

I'm just in the middle, right? I just established to you what's above me, right? My parents, my circumstance and what's below me is my employees, they're feeling all the benefits of it. It's so interesting because I'm just seeing right now your brand is just pulling people towards you, people wanting to be a part of this. You're constantly recruiting,

but not from a fake standpoint, from just a true organic showing the world who you are. It's genius. Yeah, and it's very, look, this is a very, I know a lot of people are listening right now have never heard of me, so this is gonna come across pretty aggressive, so I'm hedging, so please bear with me. I hope you see the purely good part of this,

not the narcissistic part, but my ambitions are remarkably high. Like I wake up every morning trying to have a statue made of me. You know? You know? And here's why it's worthy of a laugh and why I had to hedge it.

One could see that and be like ugh. Like what is that? I see it as if that is actually your framework, the only way you do that as a human that is not an athlete or a politician is you have to be disproportionately one of the great, nice humans of all time. I'm trying.

I think I was gifted something. It'd be like, if you're LeBron, you don't wake up in the morning at 13 when you realize, oh my God, I could literally be one of the greatest basketball players of all time. You don't kind of then run away from that and say, I'm gonna be a painter. Sometimes people do, Gary, that's the thing,

and that's what's important about this show and about your content is letting people know your job is to chase your passion. Your job is, even though it's scary, even though it's hard, even though everyone's telling you not to do it, even though the money's not there yet, go anyways. Look, you're preaching. I think that one of the manifestations of my work

that I'm most proud of is if somebody goes and reads Crush It, which I wrote in 2008 and came out in 2009, we're talking about a decade now, I mean, not only do I fully believe in what you just said because it was the manifesto, I also ended up being right because in 2008 didn't seem possible.

There was no podcasts, there was no Instagram. You're preaching, sister. Like, here's why. If you never get anywhere close to my level of notoriety or financial rewards, you will be just as happy as me in the process of chasing the practical passion. Don't worry, I'm getting there. I believe you, and I'm saying that

to everybody who's listening. You know, like, I was as happy as I am right now in the basement of my dad's liquor store packing boxes. You truly were. I'm gonna really fuck with you right now. You ready for this? Ready. Happier.

I love the process, and I love when nobody knows who I am, and ready for this? Ready. Happier. I love the process. And I love when nobody knows who I am. And when I'm underestimated. I love it, I love it. I have a chip on my shoulder. I'm an underdog. I like being underestimated. The thing that is most difficult in my life right now

is that I'm overestimated now. That's interesting. Uh-huh, now I've crossed the chasm where I could say anything to a certain group I've crossed the chasm where I can say anything to a certain group of people and they're gonna think I can pull it off. Empathy Wines may fail, we have a lot of headaches. That's gonna be shocking to everybody.

I weirdly want it to happen. Trouty does not. Trouty doesn't because, and he shouldn't because this is his first big at bat, he's disproportionately tied into it. I'm not. I don't want the loss, I don't want the Scarlet Letter, but boy, one of the great ways for people

to understand the true me is for me to have a loss in a wine business of all things. Right. I don't know, I don't know to tell you, I'm not scared of that loss. You're so unique that way in that, as I mentioned before, I had a very successful career in corporate America.

I became very comfortable, it was safe. I could see it was linear and you just keep getting promoted and the money's coming in and it's very comfy. I've had to learn in the last year and a half to take the leap into the unknown. There's total darkness and this is good for you and what you're doing there's total darkness, and this is good for you and what you're doing right now Tradi, starting this new company,

you have to just keep moving forward and it's scary. And where you love that scary is what I'm hearing, I don't, because I'm so used to loving the comfort. It's really, it can be really hard. Purebred entrepreneurship. This is some, you really hit me in my heart because you articulated it so well from the other perspective.

This is why I hate so many people going into entrepreneurship. My friends, I couldn't agree more with you need to go chase your passion, all those things that we just talked about. This is what led me to self-awareness. Please make sure you're hearing both of us very clearly. You chasing your passion doesn't mean you can't be a number four. Your passion, your happiest place might be the number four

for a leader that you blindly believe in for the next 63 years. I'm not sure D-Rock's ever gonna leave now, whereas two years ago and two of his teammates who are in the trenches with him are like, hmm, that might be true. They both just shook their head because I think that might play out.

And it may not and tomorrow we could walk in, that's fine. But where I'm going with that is self-awareness. You're right, I love the dark. I started when I was nine. You're in fourth grade. Of course you're supposed to go through school. It's also 1983, 84, 85. There is no entrepreneurship.

College is the only way to win in our society, right? You want it to have real dark? I've only lived in dark. I've only lived in the unknown. In a weird way, that was an amazing gift that you were given, although I went the other way. At that time, I would've thought your life was hell that you had to work it.

Yeah. Everybody thinks that. It sounds so hard. What's hard is not doing something that is true to you. And so I wanna really redefine success. I really, really do. I really, like this is my new thing, which is like, okay, wait a minute, right.

Everybody starts with a north star. If I, through my sheer will and gifts, can start a true movement of conversation that success needs to be happy and calm, not rich and famous, boy, could I really be good when I do finally get hit by a bus. Like, that has to be the ROI.

Like it has to be. And like my big thing is like cars and diamonds and wine and like sneakers and homes and planes and tickets to big events like please don't make that your aspirations. Fine if you want to like knock yourself out but like please understand that making $88,000 a year, loving it will always, always be making 297 hating it.

And we don't have that conversation in our culture just yet. And when people just heard follow your passion, where they get stuck, let me give you an example. If we did this podcast 11 years ago, follow your passion and the other person on the other line says, well my passion is to play video games.

There was nothing for him or her to see that they could make enough money to live in society around playing video games. When I say that now, everybody knows that you can be an e-sport star and not only can you live your passion, you can be rich and famous being ninja. I'm familiar, my 11 year old tells me every day.

So what happens is, that's my concern. My concern is that everybody listening right now, follow your passion, do your thing. If that thing is knitting, or if that thing is sports gambling, which would be highly not acceptable right now by most parents of 11 year olds, though the math behind it is very similar to poker

and all this other stuff, and I do believe that moms and dads all across the world right now have 11 year olds whose number one passion is sports betting, and they look down on it because what they look on was the past, bookies, the mafia, Las Vegas. We're all coming from our past. And I always look at the future, that's my knack. So what I see is that the sports better

is gonna be put on a pedestal similar to the stock trader or similar to a professor. Or, let me give you an example, it's already happened. If you walked into your parents' house in 1987 and said, dad, I wanna be a chef. Your dad would have been like, you're gonna be a cook in a restaurant, you loser. But what would have happened is you could have gone on

to become a famous chef, which is what culture was 10 years ago. It's not as cool today to be a famous chef as it was 10 years ago. But it's still pretty cool, and it's crazy compared to 1985 where your parents would have thought you were a cook. Well what you just taught me,

and I think it's really important to highlight this, we're all coming at something from our past experience. What we can stop in that moment and do instead is come at it from what our future may be and look to see what it may be. And open our minds to thinking differently. And if you listen to your kids, they're gonna give you insights to what the it may be and open our minds to thinking differently. And if you listen to your kids, they're gonna give you insights

to what the future can be. Absolutely. And this is a very powerful parenting tip. Every parent is judging their kids based on yesterday, but your kids are living in today, which is a better indicator of tomorrow. Attention renters, if you haven't heard of BILT, you're about to thank me. Earn your favorite airline miles and hotel points through BILT just by paying your rent on time. Let me explain.

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You know, but this is, I really like how I articulated that. Like that makes a lot of sense to me. And that has been the benefit. When I said to my dad, I wanna open a dot com in 1996, my dad had never been on a computer at that point. I'm being serious right now. Had never physically used a computer at that point. So he's 43 years old and has never in his life

used a computer. So for him to judge me deciding to launch a dot com, I ended up being historically correct. I also luckily had an incredible father who at that point saw what I did in the liquor store from 14 to 21 and saw that I worked hard and I wasn't an idiot and I paid my dues and he gave me my opportunity to do that, right?

A lot of kids go into their family business and expect their parents to let them do something but they didn't put in the seven years that I put in. You know, people are always like, Gary, how'd you convince your dad to let you do those radical things? By working my face off from 14 to 22 by the time I was 20. Nobody understood that.

So, you know, that's, so anyway, man, I'm really excited we're talking about this. I think we just helped a lot of parents. I really mean that. And hearing that you have an 11 year old, like he's more right than you are. Now, the key to this whole thing was, it's funny that I brought 14 to 22. The key if your son wants to be a professional

sports gambler or a sports card flipper or a sneaker flipper or an e-sports star or an Instagram celebrity is work ethic. This is where parents often make the mistake in reverse. When I turned 14, I was a bad student, I was already a baseball card entrepreneur, my mom and dad looked at me and said, you now work in the liquor store every day.

You're not going to Harvard, big shot? That means you're gonna have to work. You might as well start now. So, if your kid tells you that they're not gonna follow the school system and they're not gonna be in the NBA, they might not be able to be on three basketball teams. You may have to cut them to one because you want them to still have a balanced life, but they better work.

Parents are not putting kids into the working system early enough. So now you have a kid that's getting D's and F's, but he's telling you, mom, don't worry, I'm gonna be next Mark Zuckerberg. Mark Zuckerberg sold CDs. Mark Zuckerberg built apps when he was a kid. There's a second part of this conversation

that's not being talked about. I've never talked about it. I'm pumped for putting this on film as well. If you're gonna let your kid be an entrepreneur and that's the path, I want that kid to actually work. So what job do you want these kids to get? Either a business that actually makes money that they're doing by themselves, that's fine.

Get a joint account, show me Ricky. Not ideas, ideas. Execution, you got a business this summer? You're a DNF student going into ninth grade and now we're going to high school? We've had a very adult conversation that you're not gonna maybe go to college or you're not a great student?

Okay, in between your summer from eighth to ninth grade, instead of slacking off and getting ready for high school, you either A, go work at Walmart so you can get dirt under your nails because that's the future of your life. Ooh, no kid wants to do that. Or you better start flipping on eBay or StockX or show me that your Instagram account

around Magic the Gathering or around fashion makes money. So I'll give you June but if on 4th of July you can't show me a bank account that has $2,000 in it because you sold ads on your Instagram, now you're going to Walmart. Suffocating that is the key to practical parenting, instead of ideological parenting, and that is the framework of my optimism.

And confidence. And confidence. Because what happens is that kid gets real life and so what's gonna happen is Sarah is either gonna sell $480 worth of slime, which the market is gonna give her positive reinforcement. Not her friends saying that she looks pretty, the market buying $480, that becomes,

that's what was my positive reinforcement. I didn't need my teachers or my friends or the system. When I did a baseball card show and I sold $2,000 worth of cards, the market was telling me I was good. Validating you. Validation. Yes.

The market. No individual human. You didn't need anyone to do it. The market. Look, I'm literally getting, look at these goosebumps. I am too. It's a really interesting insight. That is really powerful.

It's why nobody's opinion ever mattered to me, but everybody's collective opinion matters to me. My reputation matters to me. Just not Dustin's singular point of view. And Dustin's matters to me because he knows me better than you do and now you matter more to me than you did 30 minutes ago. But RickyPants49, who leaves a comment on Insta,

he just knows what he sees on Insta. He doesn't know me. Your closest friends and relatives don't know you. Nobody actually ever fully knows you. So why are you letting somebody's anonymous comments dictate how you feel about yourself? That's so important. I get so much feedback from people

that haters crush their confidence and they really struggle to overcome them. They value other people's opinions. You know what else it does? People are like Gary, you're so humble. I don't value other people's opinions. So when people come in and say you walk on water, I'm like cool.

No really, it goes both ways, right? A lot of people talk about the trolls or the haters. You know, when you kind of cross the chasm and now you're getting macro ridiculous. And I think that's where people's vulnerabilities are. They love the praise, so now they're validating other people's singular opinion, but then whoops! What just happened?

You know, pretty goes to ugly really fast. And now you're caught because you loved him when it was pretty, but now somebody said ugly. So really it's taking those compliments off the pedestal and saying we're even all the time, we're all equal all the time and whether the comment's positive or negative, I'm not gonna let it affect me. And I would tell you if you said push comes to shove, Gary,

which one do you hear more? I have empathy for the negative feedback because I want to continue to evolve and I don't want to just say it's a hater. You know how many people say somebody's a hater or a troll but that person's actually right? No, I never thought about that. So I see a lot of people who are selling spam,

selling bullshit products and services. And when somebody leaves a comment that says you're a snake oil salesman, they're like hater, nah. Nah, you're saying that these goji berries cure cancer because you have an MLM and you're trying to sell people into it, they're right, you're wrong. So I never want to become that caricature of myself.

I never want to be resistant to feedback. So even though I don't value the opinion, I listen, it may not I don't value the opinion, I listen. It may not penetrate my soul or my behavior, but I listen and I always try to calibrate it again so like, do not become delusional, do not become a caricature of yourself. Got it?

It's very easy to get caught up when you have as much positive reinforcement as I have, but I try to keep myself very much in the zone. I like that idea of really, instead of thriving off of the compliments, thriving off of the positive feedback, let it come in, accept it, listen to it, like I said, listen to everything that's out there,

but don't allow it to affect you. Listen, I'm more likely to really be thoughtful about a troll comment than smell the roses. I really am. And I think that level of, you know, if you're gonna have confidence, you need to balance it with humility. That's where it gets really going.

And then you sprinkle a little empathy for the other person. Again, everybody who's listening, if you've literally stopped posting because somebody said you're ugly or stupid, like you have to understand that that person's in a bad place. We have to start talking about that. Like it takes energy to muster up watching something

and then leaving a bad comment. Think about how miserable, could you imagine if that was your life? No, it's very sad. Like I've never done that in my life once. No. Never. But you're right, it's all about them.

It's not about the person that's receiving the comment. The old version of me that's like that is sports me. Like I just said, I've never done that and I actually just thought of something that almost happened yesterday. Yesterday, the Milwaukee Bucks beat the Celtics. You might be a Celtics girl since you're from up there. And it goes to three to one, the series,

and I wanted to tweet at Paul Pierce, who after game one when the Celtics won said the series was over and the Bucks were finished, I wanted to tweet and be like, now what, dick? Because I hate Paul Pierce. Because I'm a Knicks fan. Again, back to how I mentioned my grandmother, because I have a version of me where I'm sad

as a Knicks and Jets fan, and I wanna pull down the Patriots and the Celtics, I'm like, ooh, that's sports. That's a different arena. That's light, but I really feel it, but that's sports. Wait a minute, that's how people actually live life. If my real life was Jets fan Gary, I would be devastated.

And the fact that that's how everybody actually is acting right now about politics and life and social media, that's why I understand be devastated. And the fact that that's how everybody actually is acting right now about politics and life and social media, that's why I understand certain things. I'm self aware that I am envious of other teams being successful. I'm sad that my team is not winning. I don't feel in control. One of the biggest reasons I tell everybody

you're fully in control is because I believe it. I believe I'm fully in control. Makes my life happy. I am not in control of the New reasons I tell everybody you're fully in control is because I believe it. I believe I'm fully in control. Makes my life happy. I am not in control of the New York Jets. Why do you think I want to buy them? That misery, I want to get into control. If I own them, then I am in control. And so that's how people live their lives.

They feel like the government's in control. They feel like their spouse is in control. Their boss, their corporation, the system. I don't believe that. I believe you can be very, that doesn't mean that women don't face more difficult things than men. That doesn't mean minorities don't feel,

there's systematic issues. But like, everybody's got problems. Having too much is a problem. I've been talking more, not only do I think it can be, if you actually hear what I said earlier, the BMW story, I spend way more time on the entitled rich kids than I do on the poor kids. I think the poor kids have it good

because they have a chip under their shoulder and with the new internet, nobody's stopping them. I think it's the rich kids or the over spoiled kids that are in deep, deep, deep, deep shit. They're soft. What about your kids? Gonna be soft. I mean it, I'm not joking.

But what can you do then to address that? I'm gonna do the thing I'm gonna do, which is I'm gonna cut them financially off, completely. Oh my gosh. Completely. Are you serious? I feel like I'm going down an inevitable path of giving away all my wealth to charity.

I really believe that. Which is wild, because 10 years ago I would have laughed you out of the room if you told me I'm going down an inevitable path of giving away all my wealth to charity. I really believe that. Which is wild, because 10 years ago I would have laughed you out of the room if you told me I'm an immigrant you put your family to money. I just think the money's a problem. That's shocking. You know it's shocking for you

even to come out of my own lips. But this is what happens when you live something. This is why I love talking about things I know instead of judging things I don't. I judged Bill Gates and Warren Buffett 15 years ago when I first heard it. But that's because I hadn't lived it yet. Now I realize, oh my God, if my kids know

that they have a parachute at all turns, they can't live a life of happiness. Which then leads to uncomfort. But I have to watch them because they're still young. For example, it's uncomfortable to me because I would never want anything I achieved to be hedged that it wasn't done by me. But that's me, not everybody's like that.

Some people love the idea of being third generation wealthy and just enjoy. I have too much pride and love of the process. Some don't like it. So you've gotta listen. So I'm just gonna be thoughtful and woke and open to all these things with my kids and we'll see. I have no idea.

Most likely one of the kids is gonna wanna climb my mountain and be bigger than me and one kid's gonna wanna give away all the money in Africa and all of that's fine. I will not judge my children on how they react to their circumstance and DNA. I will not. I have no interest in my kids being entrepreneurs.

I have no interest in my kids being competitive. I have no interest in my kids being like me. I have interest in one singular thing. Can they have as much peace of mind and happiness as I do? That's what it's all about. 100%. That's the real confidence all about. 100%. That's the real confidence.

It sure is. So I can't wrap up this show, Gary, without coming in hot. Anytime I'm scared of doing something, I have to do it. So I gotta ask you something. Go ahead. So I listen to your podcast all the time. Yes.

My career was all about coming from nothing and smashing through the glass ceilings, getting to the C-suite, being a cheap revenue officer, responsible for hundreds of millions of dollars, then getting fired and rebooting and starting my own company. I would love to share that message with your audience on your show.

You wanna be on my show? Yeah. It's done. You are the man. Thank you. You're welcome. As a mother, I appreciate a lot too. Thank you. I hope that you love Gary Vee as much as I did. I'm so excited

that we got to spend this time together and spend it with him learning how he creates his confidence. Definitely different than most of the stories that I've heard. So so appreciate you guys being here. One of the things that people have asked me is how do I get to a Gary V and how does that happen? So I want to share with you some of the things that I do. First starting with was looking at Instagram yesterday because Gary Vee was posting about me. What's so interesting is in the DMs where it shows up that someone mentioned you, I start scrolling up and you need to know this. Ready? The first time I reached out and sent a DM to Gary V was December 15th,

2016. I wrote this big note about, I love the process of what you're doing. My hashtag is Boston Heels. I'm providing the same level of transparency and success from the female side. Could we please collaborate and bring more value to your audience? Blah, blah, blah. Okay. So that was December 15th, 2016. I did hear back. I told him that I lived in Miami. He said that he's never in Miami. I said, but I come to New York.

I can meet you anytime. Crickets, nothing. Heard nothing back. Okay. Then April of 2017, I reached out. Crickets, nothing back. April of 2018, I reached out. and this was a good one, I like this one. I said Gary I'm so excited that people are buying my book and buying

yours too. I feel like I'm in great company and I sent him a picture that I got off Amazon that said people that buy Crushing It are buying Confidence Creator. That's cool. I thought that was really relevant. Crickets. Nothing. Okay. May 31st last year, I reached out, Gary, my new book came out. It's a best seller. I was just on the James L. Tuchers show discussing it. I would love to bring your audience these tips, blah, blah, blah. Crickets. June. Gary, every time I look at Amazon, my book says people are buying it with your book. I can't believe this. It means we're meant to work together. Crickets.

And then all of a sudden yesterday, I'm working with Gary V. So this is a long process. And you know, when things don't come together quickly, this is over a three year time period that I've been reaching out and trying to work with Gary Vee, the way that I ultimately got to him this time was I decided what I'm doing is not working. I need a new strategy. So I reevaluated and I was clear that going to directly to him, even though that's my goal, it wasn't working. I needed to find someone that was in his space that I could get to. So I Googled his name and then I clicked news and I saw that he had just formed a new company, Empathy Wines, and that he had a partner, John Troutman.

So I thought, maybe I can get to Trouty. And I went on LinkedIn, I connected to him, I messaged him, and ultimately everybody has a need and a want, and if you can fill that need or want, you can potentially get what your need or want is. And Trouty was really clear with me that he needs to move cases of wine. Well, I have a background in the wine business. I have a 20-year track record of driving hundreds of millions of dollars of revenue and I know

there's one thing that I know and that sales so that I could help him. He said well if you can move cases of wine for me I can get you to Gary Vee. So I made a deal directly with Trouty who was amazing and actually as you saw or hopefully saw in the video portion Trouty sat in on the interview portion with Gary Vee with me. He's an amazing guy. So the point or takeaway here is that when you can't get to the person you're trying to get to, take a step back and look at other ways to connect those dots. What other way, what other person can you find? And remember, I've been working on this basically for three years since

2016. That was the first time I reached out to Gary Vee. But the key is I never gave up and you should never give up too. So I'm dying to answer all of your questions. I actually had a question that came in yesterday that I wanted to share and this is with someone that I've known for a while and has been on this journey with me and reached out to me to say, hey, Heather, I just got this new job. I was so excited. And today they presented me with my letter of agreement to sign and the compensation was not near where I thought it was going to be.

I can't take the job like this. I phone the woman who's in charge to speak to her, but I'm feeling very nervous. I want the job. I love the job, but I'm scared to counter, what do you think? She also put, I'm rereading part five and six of her book, Confidence Creator, I thought it would help, which was really cool.

So here's the thing, in any situation, there's a value exchange, but the bottom line is this, people will pay you what you are worth. That is facts. So you need to know your worth, know what works for you, and you need to stand firm in it in a very kind, calm, positive way. There's no room for emotion in business. You need to take emotion out of it.

Getting upset, crying, yelling, feeling angry or hurt, that means you're taking it personally. This is business. We don't know that person's situation. Maybe they were told there's a cap on what they can pay, but now it's on you. This is where the negotiation begins. What is the value proposition that you're bringing to the employer? How is that going to make them money? Doesn't mean that you don't just have to be a salesperson to know you're helping a company

grow. Your goal is to show the company how you're delivering value and increasing their value and net worth. So you want to frame up your conversation in that way in a really positive way that you're so excited to go to work there that you can't imagine how successful that you're going to be as a team. Here's how you're going gonna drive value for them. However, the current offer will not work as it stands and you wanna work through a way and a solution

to get you guys to where you need to be. Oftentimes, you might be working with an HR director or a head of one department and they don't have any more funds, but maybe by going to the president of the company, you can access more funds. So you wanna also ask that person, hey, would it help you if I speak to anyone else? Is there, do you have, you know, if you're having budgeting issues, would you like me

to come in again and meet with some other people so that you could potentially access more funds and bring this together so it works for both of us? I know you and I can find a way together. You know, really believing in yourself, believe in finding a solution and be collaborative and positive with that person Oftentimes you will see that they may need your help or they just need to make another phone call and ask for additional funds So the good news is I heard back today and this woman did go ahead and she claimed her ground she said this isn't this package isn't gonna work for me and I want to work with you. And the good news is that they came back, and I'll read this to you.

She told me she will ask for more money. She will fight for me for more money. And she thanked me for my honesty and told me she has a lot of respect for me for making the call and putting it out there. So congratulations, putting it out there and owning your thoughts, your value, others will respect that and that's when for what you're gonna fear Start learning and growing

Inevitably something will happen No one succeeds alone You don't stop and look around once in a while You could miss it I'm on this journey with me