The Secret to Feeling Confident Walking Into Any Room with Gary Vee

29:15I'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 right now, Trotty, you know, 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 entrepreneur. My friends, I couldn't agree more with you need to go chase your passion, all those things that we just talked about.

29:55This 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 DRock'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.

30:32You'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 become 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 have thought your life was hell that you had to work. Everybody thinks that. It sounds so hard. 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 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 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 beat making$297 ,000 hating it.

32:12Absolutely. 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, 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. When I say that now, everybody knows that you can be an e-sports star and not only can you live your passion, you can be rich and famous being ninja. I'm familiar.

32:43My 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.

33:20That'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 going to be put on a 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 want to be a chef, your dad would have been like, you're going to 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.

33:58Still pretty cool. 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 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.

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37:47That's really, really powerful. Dropping knowledge, Gary. Trying to give D some micro content for my Instagram. You know, but this is, I really like how I articulated that. 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. 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 dot com, I ended up being historically correct.

38:27I 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. 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. No one saw that. Nobody understood that. So anyway, man, I'm really excited we're talking about this.

39:03I 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 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.

39:41You're not going to Harvard big shot? That means you're going to have to work. You might as well start now. So if your kid tells you that they're not going to follow the school system and they're not going to 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 the next Mark Zuckerberg. Mark Zuckerberg sold CDs.

40:11Mark 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 now we're going to high school we've had a very adult conversation that you're not going to maybe go to college or you're not a great student okay in between your summer from 8th to 9th 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.

41:22Now you're going to Walmart. Suffocating that is the key to practical parenting instead of ideological parenting. Right. And that is the framework of my optimism. Wow. And confidence. And confidence. Because what happens is that kid gets real life. And so what's going to happen is Sarah is either going to 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.

42:09Validating 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.

42:43He 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 we like the praise though we like the praise and I think people 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 it 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 the 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 lot of people who are selling spam, selling bullshit products and services.

44:16And 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 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.

44:59But 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, 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, you have to understand that that person's in a bad place.

45:43We have to start talking about that. 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. 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 only version of me that's like that is sports me. Like I just said, 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.

46:15And 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 like tweet and be like, now what, Dick? Because I hate Paul Pierce because I'm a Knicks fan. the only again back to I mentioned my grandmother because I have a version of me where I'm sad as a Nixon 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 and the fact that that's how everybody actually is acting right now about politics and life and social media.

47:04That'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 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.

47:43I 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 everybody's got problems. Having too much is a problem. Sure, it can be. I've been talking more. Not only do I think it can be, if you actually hear what I said earlier, the BMW story, like 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. I think it's the rich kids or the overspoiled kids that are in deep, deep, deep, deep shit.

48:21They're soft. What about your kids? They're going to 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 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 you even to come out of my own lips.

48:54But 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 that. That is comfortable, wow. Which then leads to uncomfort. 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.

49:29But 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.

50:08I 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 a 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 got to 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 and 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.

50:47I would love to share that message with your audience on your show. You want to be on my show? Yeah. It's done. You are the man. Thank you. You're welcome. As a mother, I appreciate it 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 Vee and how does that happen? So I want to share with you some of the things that I do.

51:23First, 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 Vee was December 15th, 2016. I wrote this big note about, I love the process of what you're doing. My hashtag is BossinHeels. 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.

52:03I 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 reach out, Gary, my new book came out.

52:47It's a bestseller. I was just on the James Altucher 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, day 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 V. The way that I ultimately got to him this time was I decided what I'm doing is not working.

53:26I 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.

54:11Well, 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's 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 you saw in the video portion, Trouty sat in on the interview portion with Gary V 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.

54:50What 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 V. 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.

55:32I can't take the job like this. I phoned 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 your 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.

56:14You 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 know, 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.

56:49So 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 to drive value for them. However, the current offer will not work as it stands and you want to 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 want to also ask that person, hey, would it help you if I speak to anyone else?

57:26Do 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.

58:01She said, this package isn't going to work for me and I want to work with you. And the good news is, is that they came back and I'll 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 you know you're in the right place.

58:40I couldn't be more excited for what you're going to hear. 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.