Gary Vee
Appearances
Creating Confidence with Heather Monahan
The Secret to Feeling Confident Walking Into Any Room with Gary Vee
And if you listen to your kids, they're going to give you insights to what the future can be. 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.
Creating Confidence with Heather Monahan
The Secret to Feeling Confident Walking Into Any Room with Gary Vee
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.
Creating Confidence with Heather Monahan
The Secret to Feeling Confident Walking Into Any Room with Gary Vee
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.
Creating Confidence with Heather Monahan
The Secret to Feeling Confident Walking Into Any Room with Gary Vee
She did it. Do you understand? It sucks. What people don't know is everything about me because I don't share everything like I just shared with you. The reality is I've seen it up close and personal. I know the extreme positivity. I know extreme negativity.
Creating Confidence with Heather Monahan
The Secret to Feeling Confident Walking Into Any Room with Gary Vee
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 and lived in Soviet Russia. She was a widow with a 15 year old. She had shit. She had a tough life. She was a child in World War II. I don't judge her. But I also understand what it is.
Creating Confidence with Heather Monahan
The Secret to Feeling Confident Walking Into Any Room with Gary Vee
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 coming of age and my mother. So I'm grateful. How did your dad and your mom get together?
Creating Confidence with Heather Monahan
The Secret to Feeling Confident Walking Into Any Room with Gary Vee
Sometimes opposites attract. 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.
Creating Confidence with Heather Monahan
The Secret to Feeling Confident Walking Into Any Room with Gary Vee
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. Has crazy work ethic. Let me tell you what I mean by that.
Creating Confidence with Heather Monahan
The Secret to Feeling Confident Walking Into Any Room with Gary Vee
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 life.
Creating Confidence with Heather Monahan
The Secret to Feeling Confident Walking Into Any Room with Gary Vee
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.
Creating Confidence with Heather Monahan
The Secret to Feeling Confident Walking Into Any Room with Gary Vee
at five and lost her dad for 10 years to jail when she was a teenager and like, who raised her. 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, my mom and I went on two family vacations, like my mom never complained a day in her life
Creating Confidence with Heather Monahan
The Secret to Feeling Confident Walking Into Any Room with Gary Vee
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 not compared to most or just in the mix. My mom's the most positive. like amazing, like I'm a byproduct of her. So what do you think that is, a choice?
Creating Confidence with Heather Monahan
The Secret to Feeling Confident Walking Into Any Room with Gary Vee
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 chemicals are real. I think chemicals are real. Look, this has been figured out long before us, like DNA and environment is real. DNA is... Crapshoot. Environment gets into an interesting game, right?
Creating Confidence with Heather Monahan
The Secret to Feeling Confident Walking Into Any Room with Gary Vee
It's also a crapshoot, you don't pick your parents, but what you decide to listen to and whom becomes a very interesting debate to me. You know, 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.
Creating Confidence with Heather Monahan
The Secret to Feeling Confident Walking Into Any Room with Gary Vee
Because a lot of people don't have the luxury of having family that is cheering for 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.
Creating Confidence with Heather Monahan
The Secret to Feeling Confident Walking Into Any Room with Gary Vee
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 cosine 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.
Creating Confidence with Heather Monahan
The Secret to Feeling Confident Walking Into Any Room with Gary Vee
No.
Creating Confidence with Heather Monahan
The Secret to Feeling Confident Walking Into Any Room with Gary Vee
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? I have a reason. Not the company, them. The company. I care about them.
Creating Confidence with Heather Monahan
The Secret to Feeling Confident Walking Into Any Room with Gary Vee
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?
Creating Confidence with Heather Monahan
The Secret to Feeling Confident Walking Into Any Room with Gary Vee
Because 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?
Creating Confidence with Heather Monahan
The Secret to Feeling Confident Walking Into Any Room with Gary Vee
My people are getting offered all sorts, especially for Team Gary Vee, these two characters, they just have options and that makes me happy. Kenny just left the team. He got a great gig in California.
Creating Confidence with Heather Monahan
The Secret to Feeling Confident Walking Into Any Room with Gary Vee
Now, I think it's super great here that people are naive about and I think that 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 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?
Creating Confidence with Heather Monahan
The Secret to Feeling Confident Walking Into Any Room with Gary Vee
My parents, my circumstance. And what's below me is my employees. They're feeling all the benefits of it.
Creating Confidence with Heather Monahan
The Secret to Feeling Confident Walking Into Any Room with Gary Vee
Yeah, and it's very... Look, this is a very... I know a lot of people are listening right now who have never heard of me, so this is going to 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.
Creating Confidence with Heather Monahan
The Secret to Feeling Confident Walking Into Any Room with Gary Vee
You know? Hashtag goals. 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.
Creating Confidence with Heather Monahan
The Secret to Feeling Confident Walking Into Any Room with Gary Vee
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.
Creating Confidence with Heather Monahan
The Secret to Feeling Confident Walking Into Any Room with Gary Vee
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, it didn't seem possible. There was no podcasts.
Creating Confidence with Heather Monahan
The Secret to Feeling Confident Walking Into Any Room with Gary Vee
There was no Instagram. You're preaching, sister. 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.
Creating Confidence with Heather Monahan
The Secret to Feeling Confident Walking Into Any Room with Gary Vee
I believe you, and I'm saying that to everybody who's listening. 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 when I'm underestimated. I love it. I love it. I have a chip on my shoulder.
Creating Confidence with Heather Monahan
The Secret to Feeling Confident Walking Into Any Room with Gary Vee
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 of people and they're going to think I could pull it off. Empathy wines may fail. We have a lot of headaches. That's going to be shocking to everybody.
Creating Confidence with Heather Monahan
The Secret to Feeling Confident Walking Into Any Room with Gary Vee
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. I don't know. I don't know what to tell you.
Creating Confidence with Heather Monahan
The Secret to Feeling Confident Walking Into Any Room with Gary Vee
I'm not scared of that loss.
Creating Confidence with Heather Monahan
The Secret to Feeling Confident Walking Into Any Room with Gary Vee
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 entrepreneur, 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.
Creating Confidence with Heather Monahan
The Secret to Feeling Confident Walking Into Any Room with Gary Vee
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.
Creating Confidence with Heather Monahan
The Secret to Feeling Confident Walking Into Any Room with Gary Vee
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 were 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 he 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.
Creating Confidence with Heather Monahan
The Secret to Feeling Confident Walking Into Any Room with Gary Vee
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 be real dark? I've only lived in dark. I've only lived in the unknown.
Creating Confidence with Heather Monahan
The Secret to Feeling Confident Walking Into Any Room with Gary Vee
Everybody thinks that.
Creating Confidence with Heather Monahan
The Secret to Feeling Confident Walking Into Any Room with Gary Vee
What's hard is not doing something that is true to you. And so, I want to 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.
Creating Confidence with Heather Monahan
The Secret to Feeling Confident Walking Into Any Room with Gary Vee
Thank you so much.
Creating Confidence with Heather Monahan
The Secret to Feeling Confident Walking Into Any Room with Gary Vee
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. It has to be. And my big thing is cars and diamonds and wine and sneakers and homes and planes and tickets to big events. Please don't make that your aspiration.
Creating Confidence with Heather Monahan
The Secret to Feeling Confident Walking Into Any Room with Gary Vee
It's fine if you want to. Knock yourself out. But 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.
Creating Confidence with Heather Monahan
The Secret to Feeling Confident Walking Into Any Room with Gary Vee
If we did this podcast 11 years ago, following 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.
Creating Confidence with Heather Monahan
The Secret to Feeling Confident Walking Into Any Room with Gary Vee
When I say that now, everybody knows that you can be an esports star, and not only can you live your passion, you can be rich and famous being ninja. I'm familiar.
Creating Confidence with Heather Monahan
The Secret to Feeling Confident Walking Into Any Room with Gary Vee
So what happens is... That's my concern. My concern is that everybody listening right now, follow your passion, do your thing.
Creating Confidence with Heather Monahan
The Secret to Feeling Confident Walking Into Any Room with Gary Vee
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.
Creating Confidence with Heather Monahan
The Secret to Feeling Confident Walking Into Any Room with Gary Vee
bookies, the mafia, Las Vegas. That's where 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 the pedestal similar to the stock trader or similar to a professor. Or let me give an example that's already happened. If you walked into your parents' house in 1987 and said, dad, I wanna be a chef.
Creating Confidence with Heather Monahan
The Secret to Feeling Confident Walking Into Any Room with Gary Vee
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.
Creating Confidence with Heather Monahan
The Secret to Feeling Confident Walking Into Any Room with Gary Vee
And if you listen to your kids, they're going to give you insights to what the future can be. 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.
Creating Confidence with Heather Monahan
The Secret to Feeling Confident Walking Into Any Room with Gary Vee
Trying to give Dee some micro content for my Instagram. 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. You know, when I said to my dad, I want to 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.
Creating Confidence with Heather Monahan
The Secret to Feeling Confident Walking Into Any Room with Gary Vee
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.
Creating Confidence with Heather Monahan
The Secret to Feeling Confident Walking Into Any Room with Gary Vee
So he's, you know, 43 years old and has never in his life used a computer. So for him, to judge me deciding to launch a .com, I ended up being historically correct. I also luckily had an incredible father who at that point saw what I did in a 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.
Creating Confidence with Heather Monahan
The Secret to Feeling Confident Walking Into Any Room with Gary Vee
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. 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 anyway, man, I'm really excited we're talking about this.
Creating Confidence with Heather Monahan
The Secret to Feeling Confident Walking Into Any Room with Gary Vee
I think we just helped a lot of parents. I really mean that. And hearing that you have an 11 year old, he's more right than you are. Now, the key to this whole thing was, it's funny that I brought up 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 esports star or an Instagram celebrity is work ethic.
Creating Confidence with Heather Monahan
The Secret to Feeling Confident Walking Into Any Room with Gary Vee
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 gonna Harvard big shot? That means you're gonna have to work. You might as well start now.
Creating Confidence with Heather Monahan
The Secret to Feeling Confident Walking Into Any Room with Gary Vee
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.
Creating Confidence with Heather Monahan
The Secret to Feeling Confident Walking Into Any Room with Gary Vee
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 the 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.
Creating Confidence with Heather Monahan
The Secret to Feeling Confident Walking Into Any Room with Gary Vee
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?
Creating Confidence with Heather Monahan
The Secret to Feeling Confident Walking Into Any Room with Gary Vee
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?
Creating Confidence with Heather Monahan
The Secret to Feeling Confident Walking Into Any Room with Gary Vee
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. 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.
Creating Confidence with Heather Monahan
The Secret to Feeling Confident Walking Into Any Room with Gary Vee
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.
Creating Confidence with Heather Monahan
The Secret to Feeling Confident Walking Into Any Room with Gary Vee
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.
Creating Confidence with Heather Monahan
The Secret to Feeling Confident Walking Into Any Room with Gary Vee
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. It's a really interesting insight. That is really powerful.
Creating Confidence with Heather Monahan
The Secret to Feeling Confident Walking Into Any Room with Gary Vee
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.
Creating Confidence with Heather Monahan
The Secret to Feeling Confident Walking Into Any Room with Gary Vee
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?
Creating Confidence with Heather Monahan
The Secret to Feeling Confident Walking Into Any Room with Gary Vee
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.
Creating Confidence with Heather Monahan
The Secret to Feeling Confident Walking Into Any Room with Gary Vee
One of the reasons I'm improv, one of the reasons, I mean, look, we're doing this podcast, you can see I'm like trying to run the company seconds before we sit down, I'm like trying to be cordial, I felt bad because I have fires going on right now, but you're like 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'm like, I don't want to be that, right?
Creating Confidence with Heather Monahan
The Secret to Feeling Confident Walking Into Any Room with Gary Vee
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 he was pretty. But now somebody said ugly.
Creating Confidence with Heather Monahan
The Secret to Feeling Confident Walking Into Any Room with Gary Vee
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?
Creating Confidence with Heather Monahan
The Secret to Feeling Confident Walking Into Any Room with Gary Vee
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 person caricature of myself, I never want to be resistant to feedback, so even though I don't value the opinion, I listen.
Creating Confidence with Heather Monahan
The Secret to Feeling Confident Walking Into Any Room with Gary Vee
It may not penetrate my soul or my behavior, but I listen and I always try to calibrate it against of 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.
Creating Confidence with Heather Monahan
The Secret to Feeling Confident Walking Into Any Room with Gary Vee
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, 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
Creating Confidence with Heather Monahan
The Secret to Feeling Confident Walking Into Any Room with Gary Vee
for the other person, again, everybody who's listening, if you've literally stopped posting because somebody said you're ugly or stupid, you have to understand that that person's in a bad place. We have to start talking about that. It takes energy to muster up watching something and then leaving a bad comment. Could you imagine if that was your life? No, it's very sad.
Creating Confidence with Heather Monahan
The Secret to Feeling Confident Walking Into Any Room with Gary Vee
Like I've never done that in my life once. No. Never.
Creating Confidence with Heather Monahan
The Secret to Feeling Confident Walking Into Any Room with Gary Vee
The only version of me that's like that is sports me. I just said I've never done that and I actually just thought of something that almost happened yesterday.
Creating Confidence with Heather Monahan
The Secret to Feeling Confident Walking Into Any Room with Gary Vee
But like, 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.
Creating Confidence with Heather Monahan
The Secret to Feeling Confident Walking Into Any Room with Gary Vee
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.
Creating Confidence with Heather Monahan
The Secret to Feeling Confident Walking Into Any Room with Gary Vee
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 want to pull down the Patriots and the Celtics, I'm like, ooh, that's sports. That's a different arena. That's right. 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.
Creating Confidence with Heather Monahan
The Secret to Feeling Confident Walking Into Any Room with Gary Vee
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.
Creating Confidence with Heather Monahan
The Secret to Feeling Confident Walking Into Any Room with Gary Vee
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 like, 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.
Creating Confidence with Heather Monahan
The Secret to Feeling Confident Walking Into Any Room with Gary Vee
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, like there's systematic issues. But like, everybody's got problems. Having too much is a problem.
Creating Confidence with Heather Monahan
The Secret to Feeling Confident Walking Into Any Room with Gary Vee
I've been talking, 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 on their shoulder and with the new internet, nobody's stopping them.
Creating Confidence with Heather Monahan
The Secret to Feeling Confident Walking Into Any Room with Gary Vee
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? They're 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?
Creating Confidence with Heather Monahan
The Secret to Feeling Confident Walking Into Any Room with Gary Vee
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 an immigrant, you give your family the money. I just think the money's a problem. That's shocking. You know, it's shocking for it even to come out of my own lips.
Creating Confidence with Heather Monahan
The Secret to Feeling Confident Walking Into Any Room with Gary Vee
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 Buffet 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 that. Which then leads to uncomfort.
Creating Confidence with Heather Monahan
The Secret to Feeling Confident Walking Into Any Room with Gary Vee
Exactly. 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 got to listen.
Creating Confidence with Heather Monahan
The Secret to Feeling Confident Walking Into Any Room with Gary Vee
So I'm just going to 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 going to want to climb my mountain and be bigger than me and one kid's going to want to 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.
Creating Confidence with Heather Monahan
The Secret to Feeling Confident Walking Into Any Room with Gary Vee
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?
Creating Confidence with Heather Monahan
The Secret to Feeling Confident Walking Into Any Room with Gary Vee
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.
Creating Confidence with Heather Monahan
The Secret to Feeling Confident Walking Into Any Room with Gary Vee
You want to be on my show? Yeah. It's done.
Creating Confidence with Heather Monahan
The Secret to Feeling Confident Walking Into Any Room with Gary Vee
I've never experienced skydiving because I'm like I don't like that and I don't want to do that. 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 and 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.
Creating Confidence with Heather Monahan
The Secret to Feeling Confident Walking Into Any Room with Gary Vee
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.
Creating Confidence with Heather Monahan
The Secret to Feeling Confident Walking Into Any Room with Gary Vee
No Addy, just Gratty. It's really funny about that, and thank you for noticing that. I posted it yesterday. It is remarkable that so much of what everybody aspires to get from meditation, from medicine, from self-health, from all these things that 99.999999% of people are trying to get to this place through these things. My mother...
Creating Confidence with Heather Monahan
The Secret to Feeling Confident Walking Into Any Room with Gary Vee
and my circumstances and my DNA and my father and my sister and my circumstances and DNA and so I'm so grateful for this zone I'm in I'm really, really confident. I really am.
Creating Confidence with Heather Monahan
The Secret to Feeling Confident Walking Into Any Room with Gary Vee
Yes.
Creating Confidence with Heather Monahan
The Secret to Feeling Confident Walking Into Any Room with Gary Vee
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 never complained. Never. Like, just don't have that gear. Can you start working with children more, please? Listen, what do you think I'm up to, right?
Creating Confidence with Heather Monahan
The Secret to Feeling Confident Walking Into Any Room with Gary Vee
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 form some of their opinions. I really am.
Creating Confidence with Heather Monahan
The Secret to Feeling Confident Walking Into Any Room with Gary Vee
A woman the other day tweeted yesterday, 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.
Creating Confidence with Heather Monahan
The Secret to Feeling Confident Walking Into Any Room with Gary Vee
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.
Creating Confidence with Heather Monahan
The Secret to Feeling Confident Walking Into Any Room with Gary Vee
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 wanna 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.
Creating Confidence with Heather Monahan
The Secret to Feeling Confident Walking Into Any Room with Gary Vee
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 what's the decision making process? That is an unbelievable conversation.
Creating Confidence with Heather Monahan
The Secret to Feeling Confident Walking Into Any Room with Gary Vee
We have a whole generation of parents shitting on millennials, but they're the ones who raised that entitlement. 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.
Creating Confidence with Heather Monahan
The Secret to Feeling Confident Walking Into Any Room with Gary Vee
She said, you weren't good enough.
Creating Confidence with Heather Monahan
The Secret to Feeling Confident Walking Into Any Room with Gary Vee
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.
Creating Confidence with Heather Monahan
The Secret to Feeling Confident Walking Into Any Room with Gary Vee
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. Sure.
Creating Confidence with Heather Monahan
The Secret to Feeling Confident Walking Into Any Room with Gary Vee
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, 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.
Creating Confidence with Heather Monahan
The Secret to Feeling Confident Walking Into Any Room with Gary Vee
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're 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.
Creating Confidence with Heather Monahan
The Secret to Feeling Confident Walking Into Any Room with Gary Vee
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.
Creating Confidence with Heather Monahan
The Secret to Feeling Confident Walking Into Any Room with Gary Vee
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 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.
Creating Confidence with Heather Monahan
The Secret to Feeling Confident Walking Into Any Room with Gary Vee
They've decided entrepreneurship is cool, their kid's getting Fs, 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...
Creating Confidence with Heather Monahan
The Secret to Feeling Confident Walking Into Any Room with Gary Vee
Back to like the 6th 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.
Creating Confidence with Heather Monahan
The Secret to Feeling Confident Walking Into Any Room with Gary Vee
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.
Creating Confidence with Heather Monahan
The Secret to Feeling Confident Walking Into Any Room with Gary Vee
But immediately my place doesn't go into I'm confident, fuck you. My place goes to, man. God, 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.
Creating Confidence with Heather Monahan
The Secret to Feeling Confident Walking Into Any Room with Gary Vee
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 want to give you something. Thank you.