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This is the GaryVee audio experience.
B
Okay. Gary Vee, I am so excited that you said yes. It was really a shot in the dark when my team reached out to you. And so thank you for being so willing to sit down with me today.
A
I'm beyond happy to.
B
Oh, thank you. So what many of you would not know is prior to sitting down, he was so kind and generous to take a couple of moments with two of my adult children and soon to be son in law out in the other room before we started filming. And you were just the minute you walked in, you're so receptive. You were just willing to answer their questions. They're so hungry to learn from you and have been watching you for years. And in that instant when you walked in, the way you responded to them said everything I needed to know about really and truly the character of who everyone sees online. Your goodness is so palpable from the moment you walked in. And that as a mother, I just want to say thank you. I really appreciate you taking the time.
A
Well, it's fun to say that as a mother that that is what my mom gave me. You know, it's like the best, like I could not. Last night I went to an event, very bougie, 18 very bougie guests. And so I was in this private area of a restaurant hotel that came up and the guy was a fan. And again I show up. My consistency is something I'm incredibly proud of. It's also the thing I do that's easiest.
B
Just being yourself.
A
Correct. This is the thing I push everyone on is you will not trick the world eventually. So like it's so. I couldn't comprehend spending my energy trying to put in the acting skills, the memorization. And the gentleman was very gracious to me and he's like, you know, it's nice to see that you are what you are already a couple people that have come in tonight are not. And I was explaining to him that, you know, that's a compliment to my parenting, the way I was parent. That's not a compliment to me. What you just said is not a compliment to me. You know, I think the fact you.
B
Held onto it, you didn't let all the fame and success.
A
Well, you know what's funny? I don't think fame and success changes you. I really do think it exposes you. I think it accelerates who you actually are.
B
So it's an amplifier of the core of you.
A
I don't know if there's anything that's more obvious to me. I don't know if there's anything more obvious to me than that. Money, success, notoriety, and fame is a 100% amplifier and exposer of your truth. I'm fortunate now that I've lived the life I've lived, and especially the last 15 years, where I've literally discovered so many kids before they became uber famous. Knew them from day one because of the world I've lived in the last 15 years. Social media. Logan, Paul, Jake, Paul, Charlie D'. Amelio. Fame is money. It's just. It's. And then even taking it, I'm just. As I'm talking, I'm thinking, like, Mark Zuckerberg and Ev Williams, like, the Travis from Uber. Like, money is just an exposer. Fame's an exposer.
B
I always believe money is an amplifier, but it's this conversation that's connecting it for me. So would fame be right?
A
Oh, for sure. Power. Power. A true.
B
And what do you do with that power?
A
Correct. Yeah. And so for. What just happened with the kids is like, you know what's amazing? And we were talking right before we went online. I talked about what ends up happening when humility joins the orchestra, you know? Do you want to hear the real answer? I still can't believe that those three kids look at me that way. I really can't. It's just very true. I will never. I just.
B
You'll never get over it.
A
I don't think I will at this point. I'm like, okay, I think so.
B
And that's why I think everybody of all ages and walks of life love you so much.
A
Well, not everyone does. I actually think what's unique about me is I have a. You know, I'm a funny communicator. Right. There's plenty of people listening right now, like, ugh, I'm being serious. There's plenty of people listening right now that are like, ugh, why'd she bring him on? Because in the world we now live in, in this fragmented world, me cursing about something aggressive might have triggered when people were like, oh, males that are. You know. I'm very empathetic to the misunderstanding of me. Anyone who's consumed me for enough feels that way.
B
I agree.
A
Anybody who's gotten a flash of me, oh, there's. There's some ways to misunderstand me.
B
Absolutely. And I think that the reason, probably why I was also compelled to have you come on and have this conversation is because I can sense, as a psychologist, I can sense that you are saying it how it is. You are not filtering yourself. You are Very authentic in who you present yourself to be and what you think is important, the message you want to convey. And I find the relatability in that because as a midlife woman in a space where coming out of private practice, going online only five years ago, and having this like hyper growth and hyper success and other women in the space, like, where did you come from? And almost like this, who are you? Kind of. And being picked apart in many ways from my ideology, my philosophy. I say things that are often very uncomfortable, that are my truth and my lived experience with all the clients I've worked with and just my philosophy and belief system about women, humanity, relationships. And it can be controversial at times. But I'll tell you what, when that, whether the camera is rolling or off, similar to you, I am the same through and through and through. And I think that authenticity is what either repels people or attracts them. It's like the definer of my producer always says, she's like, you're the ultimate equalizer if someone is an exposer. Yes. The thing you can't really hide.
A
No. One of the reasons people struggle with me is I'm poking their zit. Like when I say, hey, hey, at what age is it appropriate to stop blaming your parents when I ask that question?
B
Yeah, but it's a great question, you.
A
Know, if you're a 42 year old who just got done shitting on your mom and dad and saying that's why it's all not working out. That doesn't feel good when I show up in your feed with that.
B
Right, right. And what makes you think I would want to hire you as well like that? You haven't worked through that.
A
Yeah.
B
Now I'm gonna come to you if you are somebody who is trying to sell a service or a good.
A
I'm like, oh, and you'll, you'll appreciate this. It's really funny. It's almost like we're switching places. I actually don't even think of it through a commerce or capitalistic or business. Most of the way I see the world is not through the lens of my great love affair with business. It's actually, it's actually through pure humanity. I'm not even thinking what. When I make a piece of content. When I'm poking at that issue of like, what could this mean for business? I'm just thinking, man, I really hope that when I post this video, three people. This is literally my mindset. Three of the 4 million people that are about to watch this are finally ready to tip. They've Heard me say, maybe me this before you in one on one, anyone. But today's the day.
B
Yes, in my way, they're going to receive it. And I love this philosophy. Not how many views did this get that naturally happens, but the mindset going in is, I hope three people are changed. I hope three people hear this and today is their day that they take their leap for themselves. It's the same idea. When I started my 365 days of Facebook Live, which I think you'd appreciate, consistency, Gary, I had no following. I had 200 people. Yeah, I told you, my kids were telling you. They helped me set up all social media. Got a light, A shitty ring light, put it up. I put my thing in a cradle and I was like, hi. And I just started talking to the camera and I stayed on for 365 days straight. And in the beginning, sometimes there was one person in the waiting room, and while I'm talking, they were gone. And then I kept saying, okay, Amanda, if one person shows up, this is the equivalent. If they came and knocked on your front door, would you slam the door and say, oh, let me know when there's about 20 more of you out there. Then I'll actually let you in. You wouldn't speak to the one person. And guess what? Maybe one person will watch it tomorrow. Speak to the person you know who needs to hear this. And what happened next with these pills?
A
Well, that's. That's why it happened.
B
And I didn't quit showing up even when there was a low audience.
A
Let's break down what you just said. I'm not gonna do this for the selfish things that I might get out of this. I'm gonna do this upfront for the selfless thing that might create the selfish thing that I might want.
B
Yes, yes, got it right.
A
That's why, by the way, I never worried, nor to this day worry about my. Ah. In fact, fancy friends that have lots of followers like me always ask me why I don't archive low performing posts. Because I have no interest in the perception. I'm not. I'm not even there for the reality. Meaning everything I want to happen will happen if I continue to provide value. The end. And so, yes, that's why it worked for you.
B
I love that so much. Tell me this. What would you say now is the difference between when you first got started and what you believed about ambition and success and maybe it was very little that you even understood or knew back then and where you are now? Is there something that has really changed that you say, gosh, if I could go back and talk to that younger version of me, I would tell him.
A
That, no, no, I'd love to appease the conversation. I'd love to show the humility or the journey or the scars of a life. Is there anything about ambition and success that is different? I'm sure something subtle. Maybe I can sit here for a few minutes and think. The real answer is absolutely not. Predominantly because. So a lot of people really don't actually genuinely know my story. From 14 years old to 22, I worked at my father's liquor store for two to five dollars an hour, every weekend, every vacation, every break, all of them.
B
So your friends are going off doing fun things, and you're working.
A
Starting in early high school. We're talking early high school. I'm not talking about after College. I'm talking 14 years old. Saturday, Sunday, liquor store, Easter break, liquor store. First day of summer vacation to Labor Day. Monday, liquor store. And I at first hated it. And then by year two, when I realized people collected wine because I loved collecting, I made it my own. And at 15 or 16, dad, please don't get mad. This is just. I want to be very honest. At 15 or 16, I was like, oh, I'm a much better businessman than my dad, which was very weird. At 15 and 16, 14, you know.
B
You could already see things.
A
And I'm not saying again, if you knew me real well. I wasn't saying it like, it was just with. I didn't even say it out loud. I was just saying it to myself, which very quickly got into, I'm gonna help my parents, because I was already there. This goes back to the point of the foundation of my childhood. And, like, I can help them. I already was aware that by being so. I'm a Soviet immigrant, everyone. I was born in the Soviet Union. I was already in a place where I was so grateful for what my parents had done, I. By just getting us to America. And then I had this mother that was so uncomfortably great that I'm just cooking with gas. I'm like, I need to give back. I would argue so, you know, I work in this liquor store. Then when I'm 22, I'm getting paid 35, 40, 50,000 a year. I built my dad's business from a 4 million to a $60 million business and never made $100,000 a year.
B
Oh, my God.
A
I started my career at 34 years old. And by the way, just for everyone to really hear it, from 22 to 34. And I worked 100 hours a week. We were in retail. So it was Monday through Saturday, 8am to 10pm no lunch break. And then occasional Sundays, 12 to 5. But I had to watch the jets, you know, in the fall and winter. And then the holidays. Call it the week before Thanksgiving until New Year's day. You're talking 15 times. 120. I mean, like, real labor. It was funny. I was on TikTok Live the other day. Everybody, the people that are know me now, they're like, I was talking about something like, yeah, Gary, have you. But have you ever done manual labor? And I, like, almost burst out of laughter. I'm like, I've done only male. I mean, I have a massively substantial QL issue on my back. All I did was child labor and manual labor from 14 to 34, and real stuff. I'm talking, you know, pallets and hand trucks and carrying boxes that weighed as much as me. Anyway, from 22 to 34, I was conscious that I was building my dad's business for him. A lot of people, when they try to rag on me, they're like, he's not like us. His dad gave him a liquor store. I'm like, no, he didn't. My father owns the family business right now. In fact, if I was lucky enough to not have a father that had a liquor store and just randomly worked in a liquor store and took that liquor store from 3 to 60 million in revenue, I would have made a million dollars a year as an executive. So I think for immigrants, they get it. The family business dynamic is wild. And sometimes when you're the kid and you're the real driver of the business, you're super fucked.
B
Tell me, what were the dynamics there?
A
Yeah. In the early 30s, you know, after I got married, my first marriage, like, there was. I was like, wait a minute. I have to worry, you know, from 22 to 29, I was just doing it for my dad. I didn't give a shit about anything but build, wine, library, right? I didn't give a shit about anything. I gave up my entire 20s, which was a massive vulnerability. Back to balance. Not having any leisure or any fun in your whole childhood is bad. Like, no question. As I got into my 40s and, you know, how does it come back.
B
To represent itself later in life?
A
The only version of regret that I have, you know, I think regret is a poison. And I'm like, wasted energy. Ugh. And honestly, I'm like, so lucky. Like, it's so minor, but I can taste it.
B
Yes.
A
You know, like, you know, I'll use alcohol. I'm not an alcoholic. But I have a glass of wine every Thursday night. But even that glass of wine is maybe not productive. And so in my late 30s, early 40s, I'm like, I blew it. You know, like. And that's not in my framework.
B
Right.
A
Yeah. I'm trying to really break it down. So, anyway, back to your original question. Success and ambition has only been one thing for me. I'm gonna build the largest sandcastle at the beach. And at the end of the day, when my parents call me to eat, I'm gonna break it down. Cause it's not about the castle. It was about all day at the beach, building the castle, the experience. That's it. I could care less about every trophy I have. All of them could give a shit about Gary Vee. 50 million followers, my bank account, my notoriety could give a shit. No.
B
What about the person who's like, well, it's easy for you to say, Gary, because you have it.
A
Very easy. I have it because I didn't give a shit.
B
Oh, so you think that's part of the equation?
A
No, no, I think it's the equation.
B
Oh, my God. Even better. It's the equation.
A
It's the equa. It is now. There's. Now for me, let me. To everyone's credit, on the counter, there are two ways to get to the tippy top. Extreme confidence and simplicity. Extreme insecurity. There's a difference, though, right? Once you get there, sustaining it. When you got there through darkness, you become Darth Vader and you lose.
B
That is so important for people to hear this. This is one of the questions I wanted to ask you. So it leads into. So getting there, getting to the tippy top of the mountain, and you've arrived. There are two different ways to get there, but one, it will be hard to hold. So you've acquired, acquired, acquired. But how do you actually hold and continue?
A
And how we define hold. Hold could be. One could say, gary, you're wrong. I can point to examples of people who. I always say, there's two ways to build the biggest building in town. One is to just have the talent to build the biggest building. Two is to tear down everybody else's building. And one could say, gary, you're wrong. I'm going to point to 10 examples. Right now. They're thinking it of people that got there through extreme narcissism and insecurity and stay there. I ask them and challenge them. What is the definition of maintaining it? I would argue eight People showing up to that funeral is the ultimate loss.
B
Oh, that is such a telltale, isn't it?
A
I think so.
B
And when it's all said and done, how many people are really there for you? Because if you had to come cut so many people and step on so many people to get there, is that actually success? And for some people, they would be like, absolutely, I just want to be there by myself.
A
And great news, they're allowed. I am, by the way. You want to hear something more extreme? Even though I'm passionately in disagreement, I have no judgment.
B
Yeah.
A
Mazel tov. Knock yourself out.
B
Right.
A
Just not for me.
B
Right? Not the way you're going to build it.
A
No.
B
So let me ask you this. A lot of my listeners are the women. You know, I wouldn't even say I have women in their 20s, of course, who are following me, who've hired me, who come up to me on the streets in New York all the way from the 20s into their 80s.
A
Yes.
B
But I would say a good mass majority is 35 to 55, who's probably watching.
A
I love those ladies.
B
These are the women who primarily hire me and come to me and they're like, I feel like I missed the boat. Of course I feel like I missed it. I have all this entrepreneurial energy and spirit. I've got all these ideas. I've helped some of these women take the most unbelievable ideas and believe in themselves enough to turn it into a physical product, a service of good love, whatever it is. But it takes so much to get the women to a place of belief that it is not too late. What do you say in your own language to those women who are like, ah, shit, I'm 45. I'm 48. I mean, I didn't start Gary online till I was. I was just turning 48.
A
Yeah, I get it. Couple fun things first. This is going to be the most fun thing to say. Good news, all the guys are like that too.
B
Yeah.
A
I just want to start with that. I find I have so many women friends, good friends, startup founders, I back, you know this. Anybody in our society today that is not a white male will have energy towards. Yeah, but I'm not a white male.
B
Yes.
A
So I. So many of the women that are my homies, I love to remind them because I'm a white male and I skew 70% male audience. And I love to start with step one. What do I say to all of them? Good news, all the guys are the same too. There's this misconception like, ah, Cause I hang. I mean, I'm part of a bunch of women groups.
B
Yeah.
A
And this goes a lot to like my mom being my hero. I have a lot of like, interesting points of view on this issue anyway. Nonetheless, I love to like. They're like, but guys, you know, cliche me hanging out with 10 women over dinner. Ready? This is real life in my life or on Zoom or what have you. But the guys, they like, guys will never be scared to like these. You know, the girl talk is the funnest for me. Cause I'm half girl. Like, they're like, you know, these idiot guys who don't know anything are quick to be like, stand up and we're holding back and we know the stuff. I'm like, it's not true. They're like, what do you mean? I'm like, I have 13 guys around me in my biggest companies right now who are scared to speak up and they know the answers. It's not a girl boy thing. It's a self esteem thing. It's a delusion thing. Sometimes. Sometimes the guy or the girl. By the way, I know I have women in my company right now posturing that don't know what the fuck they're talking about. They're in delusion. Other women in my company, very senior, six, seven figure. We're talking real people that are posturing and are coming from confidence. So again, it's back to the thing we just talked about. It's either just so you know who's jumping. The confident and the delusional.
B
Yes, yes.
A
And the sex, the race, the gender, the age. That's not the correlation. It's how they grew up, family dynamics, childhood, nature, nurture, and many other variables. So what do I say to them? Say a couple things. One, ladies, when are you ready to not live in high school?
B
Oh, Gary. Yes, yes.
A
Almost every woman right now, 35 to 55. But also anyone who's listening that's 35 and under and 55 and older, and any dude that's listening all have the same thing going on in this issue, which is they are not interested in living their most true happy life. They are not interested in mitigating regret later because they're worried about the opinion of either literally the general public that they don't Even know Johnny Johnnypants49's comment or. The misery loves company people in their life, often their mother, often their father, often their sibling, often their spouse. Let's talk about the ladies. There are so many women right now that are not willing to jump because they're worried about the impact on their insecure husband.
B
Oh, I know that. I deal with this.
A
I'm sure.
B
Oh, I deal with this all sure, all the time.
A
I'm sure you do.
B
It's usually the husband, he's gonna be threatened by me doing something, taking up space that's not paying attention to him.
A
Or being more financially successful than him.
B
Oh, that's a big one.
A
Massive.
B
I know. My husband's like, it's the. It's the greatest thing in the world. Like, this is a dream come true success. And all these like, wow. The other one is what I. I spoke in Amsterdam at mindvalley event a couple of months ago and I had so many women come up to me the next. That evening. There was like an after party and they said, I went back to my hotel room and because of you, I turned my camera on and I finally spoke. And it's all real because they are so terrified that nobody cares about. About a woman 50 and over speaking.
A
In a camera, which is insane. I mean, that's insane to me. In fact, I have some good news to Everybody who's over 70 listening or watching. I actually think we're getting close to the. You know, I think the world is pendulum swings always.
B
I do too.
A
I think we've just lived through the rise of youth culture, everybody, right? Technology, plastic surgery, biohacking, 70 year olds who look 25. Like, I actually think we're dangerously close and I cannot wait. And in fact, I think this is like life smiling down at me. I predict in 20 years, when I turn 70, it's gonna be the era of the 70 year old. I think wisdom. I think one of the great missteps in society is that only 40, 50 years ago we put grandparents on a pedestal for their wisdom and now we make fun of them for their lack of technical understanding. I think this is a grave misstep.
B
I could not agree with you more.
A
In fact, let me give you a left field one. Everyone. I could not recommend you spending time with someone over 70 who is not your family member. Go get some time. You want to do something for your soul, everyone. You want to do something selfish that will look selfless? Go donate 5 hours to a retirement home. Go donate 5 hours of your time. See if your local retirement home will call, literally Google ChatGPT retirement homes around me, call, say, will you allow me to come and give 10 hours of public service, help wash dishes, talk. If you are lucky enough for them to say yes, because I don't know how it would Work with some of them when you go, when you're lucky enough to get 15 minutes to sit down to somebody who's 90, news alert. They will all be thrilled because there's a lot of loneliness. What they will give you, forget about what you are giving to them, which will be a lot, by the way. What they will give you has the deep potential to change the course of your life. Hey everybody. Hope you're enjoying the podcast right now. Make sure you follow the podcast. That's why I'm interrupting. Let's keep going on this show, but follow the podcast. It'll make my mom super happy.
B
Gary, I am covered in chills. Do you know in college I worked in a retirement community. That was my job. I worked in a nursing home. It is fundamentally. I could cry right now. It's fundamentally why I am aging naturally. Because there's so much wisdom and so much beauty in people that age and change and I don't know why the rest of the world is not seeing it.
A
I agree.
B
It's just some of the most beautiful years of my life were spent.
A
I would argue, without knowing much about you, that it might be the most significant thing that ever happened to you.
B
I really would say it was one of the stamps on my heart that fundamentally changed the woman I am.
A
Yep.
B
And it was talking to people in their 70s, 80s, 90s, and I was on the Alzheimer's wing. And so I was, I was often with the loved one who would come to see them. The husband who would come after dinner, the wife who would come.
A
Tough stuff. Oh my gosh.
B
And the stories they would tell.
A
Can I tell you a story?
B
Yes, please.
A
When I immigrated to America, we were poor. We had $300 to the family. We lived in the studio apartment. The size roughly, actually it's usually, I always say bigger than what? It's really interesting. Roughly around the size eight deep. Eight family members. My great great grandparents, my great grandparents, my grandmother, my parents, myself, and occasionally. Cause you know, immigrant life, like a cousin would come through for a few minutes. You know, my mom was pregnant, which was a bad thing because the first thing the American side of the family said when we got here, distant relatives were like, do not have another child. My sister comes immediately. So my mom is with her. I am spending most of my fourth and fifth years on earth with my great grandfather. My great grandfather grabs me in the morning and we go outside and I go and sit and hang out all day with 80 year old men, first name basis, speaking Russian, talking to them and pretty much in Hindsight, I've been hanging out with old men and women since I would argue that I myself have been 80 since I was 6. And that's why I think it's working. Because when you're 80 and you all know this, who are listening, the coolest part about becoming 80 and 90 is you don't give a fuck.
B
Oh, I don't give a fuck at 53.
A
Me neither.
B
I am so uncensored.
A
I have been giving a fuck for a very long time and I definitely don't give a fuck. I just turned 50. But you really don't give a fuck at 83. You know what I mean? We will give less fucks at 83. We're pretty much don't give a fuck. But there's even more to go. I think this theme we're talking about is very important. So what would I tell the 35 to 55 year old that if you hung out with an 85 year old, that's not your grandmother. No baggage, no dynamic. What you would learn is you want to mitigate against regret. Because when you talk to an 85 year old, they will talk about, you know, what is great about 85 year old women. I do this a lot, by the way. You know my favorite, favorite thing that an 85 year old woman will touch.
B
On what she regrets?
A
The boy she didn't marry. Oh, big one for that crib. Because they're part of the. I don't believe the. I don't believe your. I don't believe this Gen will have that right. They're part of an old school era where like their parents made them the first boy that liked them. The war, there's some crazy shit.
B
That's right.
A
You know what I mean?
B
That's right.
A
And then for a lot of women of that generation, it's the thing that so many women of your generation, and definitely the younger generation, you have had more professional opportunities. You know, they really, you talk to those women like this is what I always remind people, they're like, it's so bad now. I'm like, it's better than it's ever been.
B
What my grandmothers could never do. And they both had very less than ideal marriages because they had no skill set. They couldn't make their own money.
A
How about the law? I know, what do we forget about?
B
We didn't even get a checking account. Neither one of them.
A
Correct.
B
Until the year I was.
A
These psycho grandfathers of ours fucking held our grandmothers like, I don't think people, people do. You know what's funny. I was a very poor student. Very poor. D's and F's, which is wild for an immigrant. D's and F's. People, when I say it out loud, they think C's and B's. No, no, D's and F's.
B
I actually mean D's and F's.
A
But I was good at history and I think that one of the things that keeps me happy, like AI.
B
Yeah.
A
I'm not worried about AI because I know the history of electricity. Electricity was demonized and was gonna ruin the world.
B
I literally was just talking about this yesterday. I can't believe it. I use electricity as the example.
A
So I'm, you know, I'm not depressed because I know it's better. Of course, it's not better in every situation.
B
It's just how we use things.
A
It's just we spend all our time dwelling and being scared. And then people figured out that fear is a weapon. So you have politicians, parents, bosses, weaponizing fear. And then there's a few of us out here trying to sell hope and love, practical optimism. I'll tell you what's worse than being scared is being entitled.
B
Oh, and I want to talk about that, about the next generation. But before we do that, I want to talk about the fear. What I see a lot of people doing is they're absorbing the fear of either. The reason a lot of women don't go do the thing is they're either absorbing the fear of a mother, a father. My mom, when I started going online, she's like, this is dangerous.
A
Yeah.
B
Why are you talking to the camera? Like strangers are gonna.
A
Yeah.
B
And now she's like, you don't have your address list to do. And I mean, of course there's some common sense things that she's about, but she. My mom has operated and I love her so much, but she's operated so.
A
Much of her from place of fear. Of course she has to the end.
B
And think I live now as the 102 year old version of me. I think about her, I keep her in my mind's eye when I get there and I'm taking my final breath and the door of my life is closing. I don't want to have a damn regret not to tell all the people how much I love them all of the time. Not to do the thing or say the thing. Because Billy John, 2367, who's in his mom's like basement telling me, go away, grandma, nobody cares about what you're saying. I could give a shit about that, like, I am not gonna base my life and my decisions in this wild heart on some.
A
You have to hear this. And sometimes it's not a freak in the basement.
B
No. But, like, no, no, no, no, no, no, no.
A
I think you're right. What? I actually want people to be a little more thoughtful on this. I say freak in the basement all the time, too. I'm not picking on that. It's almost never a freak in a basement. It's just an unhappy person that's trying to tear someone else down to get a little solace for a second. And often it's a guy sitting in a corporate boardroom or on a plane right now, or a lady. Like, by the way, I literally did a live today on TikTok and somebody was like, man, you have an age. Well, you really rag on me. And I literally picked up the phone and I went to the light and I said, do I look better? And everyone's like, holy crap. Cause I looked way better. And I was like, I don't even care enough to get my lighting right.
B
I know, I know. The message means more than the lighting. I remember that. I know. Now my producer's on my ass all the time about my.
A
Yeah, yeah, listen, listen. There's, you know, like, it's not a bad thing to do, but again, yeah, I mean, listen, I think that had a lot to do with what you did early on. I think you've been thinking about your 102nd birthday the same way I think about it all. I. You know, I don't know if you noticed, when I walked in, when I hung up on the phone, I said, I love you. That was to my best friend Brandon, who runs the wine store. I say I love you to everyone. Like, why not? Cause I do. Cause why wouldn't I? And everyone who just responded in their heads to, like, what do you mean, friends. I love everyone for real, by the way, because ultimately I love myself.
B
That's it. That's it.
A
Like, no shit. You don't say I love you to others. You don't love yourself.
B
You can't extend what you don't already have or feel.
A
Of course, instead of being mad at your dad who never said, I love you, and using that as a 48 year excuse, how about showing compassion to your dad in realizing he didn't love himself?
B
Yes. Oh, my gosh, Gary, I feel like we are. You're the male version, I'm the female version of you. This is literally what I tell my clients who. I use the analogy of going to Home Depot, right? You keep going to Home Depot every day and you're asking, where's the milk? And they're like, oh, we don't sell milk here. But the store down the street does. You come back every day, Ma', am, I'm so sorry. We've never sold milk here, but we have paintbrushes and light ladders, right?
A
You're asking for something they can't sell you.
B
They don't have it. So it wasn't against you. They don't even have it for themselves. They've never carried it well.
A
This.
B
You think they would offer it to.
A
You because people lack the humility. People lack the detachment.
B
Yeah.
A
People don't realize they're completely self infatuated.
B
That's a big one.
A
I think so.
B
It's. It's really. It's the bane of my existence sometimes with some of these people.
A
Right? Like, like, what do you mean? Your dad? What about your dad? What did you do for your dad? How about that? That's a good one. That's one that I haven't even really pushed enough on. Where we at here, everyone?
B
This is like a creative relationship.
A
Yeah. This whole concept of the entitlement of childhood is fascinating.
B
All right, let's go with it. Because I.
A
Someone birthed. Hold on now I'm getting hyped.
B
Yeah.
A
Yeah. Someone fucking birthed you. Yeah. And then you're like, do more. They did enough. Yeah.
B
They gave you life.
A
400 trillion. Do you know this? It's 400. Current science has it at 400 trillion to one. The likelihood of becoming a human. Yeah. So let me get it straight. So someone that contributed. We're using dad here, the person that contributed the sperm that you became to create a 400 trillion to one Lotto ticket. You want something else, right?
B
Isn't that enough?
A
That's the. Yeah, this is. We need to change. How about what? By the way, I think it's. I think this comes natural to me because it's. I talked about it early in the podcast. I thought about what I'm gonna do for them at 14, 15. I'm like, I'm better. Instead of what normal kids do. And I say normal. Ooh, I'm gonna go out and do my own thing. Right. And by the way, my dad didn't make it fun either. I love my dad, but like, my dad's not my mom. Not only did I build it, I. By the way, you know why I'm good at therapy? I was my dad's therapist from 15 to fucking 40 to today to yesterday, I moonlighted. People give me a lot of credit for the business I built for my dad. I'm like, if I didn't spend three hours a day being his therapist while I was building the business, I would have built $100 million business for him.
B
I believe it.
A
I have a lot of practice in therapy. It's called having my dad.
B
I love this. I want to talk about.
A
But by the way, I'm sorry. I apologize, because I've never said this, actually. Something just popped in my head. I don't think I've ever. I don't recall ever saying. I think watching my dad's transformation over those 25 years is actually why I have so much fuel to do what I do publicly. I mean, I am so happy. One of the great things that happened in my life is watching my father evolve. My father told me that the employees were our enemy. The day I started for him. He told me to keep an eye on them because they're gonna try to steal. They're the enemy. And I taught my dad that. They're the family. Wow.
B
How beautiful is that? And so beautiful that he was able to receive that leadership.
A
Well, 20 fucking five years later, with all due respect and 700 trillion hours of fighting.
B
Yeah, yeah.
A
You know, but Ish. Because, you know, this. It's just a band aid. Ish. It's just. Everybody has a ceiling. Let me talk about a vulnerability. Instead of being like, I'm so. Yeah, let me give. Let me give you my vulnerability. I. This is gonna blow you away. Because as a public figure, it's my strength, but in private, it was my weakness.
B
Okay.
A
I will only ever in my lifetime get to. So great at candor.
B
Why is that?
A
Because it's really. Doesn't come natural to me. My mother struggles with it, and that was my North Star. I got her DNA. I got parented by her. I acted on it for the majority of my life. And for most of my life, I thought it was my strength until I realized it was my kryptonite. Every bad thing that has ever happened in my life, in my life is 100% attributable to my inability to be canderous with the people I like the most.
B
Wow. Wow. Is it still plaguing you?
A
I would say that the fact that I can say this out loud and the fact of who I am, I would say not plaguing me now, it's annoying me.
B
Okay.
A
Right.
B
Do you think it's something you're gonna be able to work through?
A
Of course.
B
Yeah.
A
I mean, I've gone from. In a world where I was really gifted with the DNA, the circumstance, and the mother, the architect, that allowed me to be an 8, 9, 10 out of most emotional things. Yeah, I was a fucking two in candor, maybe a zero. And then I started, for example, there was a Facebook group that was started of former employees at Boehner, where 12 of them were just ragging on me and people I gave a lot of heart to. But they weren't wrong. They were upset on how they got fired.
B
Oh, you just told them, like, you sucked.
A
No, I wish I did.
B
Oh.
A
I told them on Friday that they are the best. And on Monday, I told them they were fired. Got it. I wasn't able to give them the critical feedback, and the way I thought I was rewarding them was letting them be able to work there for another two, three years. So I thought I was giving them, like, you know, I would blame them back then, in my 20s and 30s, I'm like, how do you not, Johnny? How do you not see it? You stink. I'm a fucking. I'm the best. I'm, like, still paying you, and you stink. Yeah, but I didn't say that to Johnny. I said to myself. And then finally, I would tip over. And Friday, I'm like, johnny, good job on that thing. I'll see you Monday. And then. No, no, no, no. Monday, Friday, I'd be like, johnny, have the best weekend. Good job on this. And Monday, be like, hey, Johnny, you got two minutes? I'm like, hey, so you probably know Johnny, like, we gotta let you go. And Johnny's like, what the fuck are you talking about? I had to eat that. I have to own that publicly. And that sucks. Because you know what really sucks? Saying you're sorry to Johnny sucks. Cause Johnny sucked. I did pay him for three years, and he did nothing, you know? Right. But I also did the wrong thing because I lacked the critical feedback, and I rebranded it. I branded it Kind Candor to myself, and I scale it in my companies. We're about Kind Candor.
B
Okay?
A
We're gonna tell you, but we're gonna do it in a very humane, very 360, very thoughtful way. And the intent is that this Candor allows us to fix it so you can stay. Not set it up to fire you.
B
Right, but if, in fact, it is not remedied, then. Yes, exactly.
A
So that's it? That's that little rant on my little, you know, enough of razzing my dad for his shortcomings. My shortcoming. Is which really blew people away when I started talking about it. Because Gary Vee is a candor king. Because right now I'm talking to the world. It's very different than talking to people. That and the way I feel about training, compared to six months, I feel close.
B
Yes.
A
It like, you know, it gets harder.
B
Yes.
A
And then Forget about training Sid 10 years or Kaylin or Marcus. They're fucking family to me.
B
Yeah.
A
And that's when it gets hard.
B
It does. It really, really does. I agree with you.
A
So that's something I continue to put out public to suffocate myself to get better at it. But it will be a forever work in progress. Hence, yes, my father is much better at seeing an employee as family than the enemy. But deep down, my dad's probably walking through the liquor store right now, saw some employee get on a quick phone call and want to fire the shit out of them. He still got it in him. It's work.
B
Like, you're doing me wrong. You're not. You don't really care about this business.
A
Which I keep reminding him of. Dad, nobody should care about your business. You want them to care as much as you give them half the business.
B
There you go. It's so true. It's so true. Let me ask you this. So to the listeners or to the youth who are in there, I'm either fresh out of high school, fresh out of college, and every friend I know is becoming an overnight millionaire. Everybody is successful. They did two TikTok videos. They went viral. So there's this sense, I gather, that they believe everyone's an overnight success and that it's easy to come by. Fame and fortune are easy to come by. What do you say to those? There's like this sense of it's easy. And if I try three videos and they don't go viral, I quit first.
A
That they're fucking delusional. We have become infatuated at looking at 150 people and forgetting that, for example, there are 8.3 billion people on earth.
B
My husband says this all the time. He's like, the fact you even know their name tells me that's how few there are, considering the large population in the world.
A
Your husband's very right on this.
B
Why do you keep focusing on. It is hard work if your beauty.
A
Standards are someone who has spent $3.7 million on plastic surgery. The fuck are you talking about? It's so true if you're financial, Gary. But what about Elon and Zucks? I'm like, what about 830 million people on Earth do not have access to clean water.
B
That's right.
A
How about 800? Let me say it slow, if I may.
B
Yes.
A
As a proud board member of charity water. 830 million, almost 3x the US population does not have the ability to get to clean water within four hours. Within four hours. 830 million people cannot get to this. What are you crying about?
B
Oh no. Shit.
A
Look, I think the kids are using that as an excuse. I agree to say to their parents so that their parents give them money to do dumb shit. I love that. That's what I actually think is happening. I think they're wah wah wah to their parents because we are living in a generation where parents demonized losing too much. So one of the reasons we Talked about my POV on college 15 years ago and the nuance within there, which is, and I'll say it again for some mom or dad that's listening, I do believe it is crazy for a child in 2025, 2026 to go to college if they are highly creative or entrepreneurial. Not if they're trying to get a legal career. Not if they're right and they are collecting massive debt.
B
Yeah.
A
If you're creative and entrepreneurial and mommy and daddy are going to pay for your college, go have a four year vacation. I did.
B
Yeah.
A
I didn't do shit. I played Madden spades. CeeLo hooked up like, like go. Yeah, but if you're collecting debt, you're out of your goddamn mind. Same to this one. If you're a parent that tells your kid, if you have a six year old right now and your six year old just played a game of basketball and he or she came off the court and they're crying and you said, honey, stop crying. It's just a game. You're a fucking asshole. And let me tell you why you're a fucking asshole. You got lucky that you have a child who was gifted with the DNA to care. And you are starting the process of teaching them indifference. And if you know what indifference leads to, you're gonna get very serious with me here. Friends, six place trophies has destroyed our society.
B
I've heard you say this before. I'm obsessed with this, happy that you say this.
A
Listen to me everybody. Winning and losing is real. It's called life. But here's the secret. Losing is good.
B
Yes.
A
If you have a kid that falls in love with losing, very good things will happen. I fell in love with losing, which is why I'm not scared of anything.
B
That's right.
A
So we Demonized losing. We told our kids, it doesn't matter. We told our kids, you're gonna get a trophy, too. We told them, it doesn't matter. It made them scared of losing. So what the fuck do you think happens when they become 22 and go out to the real, actual world? No shit. They're saying to you, eh, mom, you don't get it. Everyone's getting famous on TikTok, secretly saying, mom, give me a thousand bucks.
B
Yes, yes, exactly. And I'm so terrified to go out and try something and look foolish. Like, look foolish for who? I don't even understand what we're talking about.
A
And now let's get deep. Mom and dad give them a thousand bucks. Because mom and dad are also scared of the judgment of their friends to see if Johnny sucks or not.
B
That's right. And it's so important I've never become overly attached to my kids outcomes. Who they become in the world is who they become. They're their own unique individual.
A
You're so brilliant. Good news.
B
I don't need them to be successful for my ego or first, so I can show them.
A
You also understand that you don't have full control, this ego of parents. As if, like, I do not judge people based on their kids, ever. There's something called DNA.
B
That's right.
A
I mean, we had a tragic event happen in pop culture just now. Right? Like, is that how we judge those parents? I sure don't. There's so many variables.
B
That's right.
A
I can tell you right now, my parents have three children. They're all different. I have two children. They're gonna be different. I have five nieces and nephews. They're all gonna be. Everyone's different.
B
Yeah. And there's so much nuance that's out of our control. And what our children choose, DNA is real.
A
Like, you have a distant cousin that was a loser and the DNA got in there. It's not you. In fact, the grandparents are a big factor if you really look at it. It's a lot easier to understand someone on their four grandparents than their two parents. A lot of times you can really see it clearer. I've got a little more data there. Now. I can see it because you look at the parents, you're like, where the fuck did that come from? Ah, Granddad was a fucking lunatic. You know, was a silly character. Like, you look at parents, you're like, where did that sense of humor come from? Grandma was a fucking gag. So, like. Like, I don't understand how we're confused by this. And. And I don't know, like, man, we are just way too detached to the outside and we got to get really insular real fast.
B
Yes.
A
This is about you, with you, about you and you.
B
Always, always, as we round this out, Gary, and the fact that this is called things your mother never told you, and you speak so highly regularly about your mom. I would love to. I would just love to know what was it about your mom that makes her so for mothers? Because there's a lot of mothers who are listening to this. What do you think the impact that was so special that she had on your life? What was that?
A
I'm gonna really fight it here, man. God, I'm a really good communicator. I was really gifted, you know. I will be forever known because of my gift of gab, Wordsman Smith, my sheer ability to speak from my heart. I will never in my life be able to give you the answer to this question. It's so much bigger than the capacity of my communication. First of all, let me start with something that I think everyone should hear. It had very little to do with what she said. It had everything to do with what she did. I watched my mom, my dad, worked his fucking face off. We were immigrant immigrants. I didn't fucking see my father until I was 14 and started working there because he worked so much that he would wake up before I woke up and he would come home after I went to sleep. My father and I slept in the same roof every fucking day of my childhood. Except for six days when my mom and sister and I went to the Holiday Inn in Orlando and ran out of money, by the way, three days into the trip, on our only vacation that I took as a child. People really do not know where I come from. I watched her, raised three children with a husband that was never around, with not a single babysitter in my life, without a single human that cleaned that house outside of her. With three children that didn't do shit and she did it all. I've never done laundry in my life. I had to find girlfriends in college to help. She had a mother in law, my father's mother, who would come to our house my entire childhood on May 3rd, her birthday, and leave on September 10th, my dad's birthday, and spend every minute in that home shitting on my mom, bringing negativity, shitting on my dad, shitting on her. And you know what's so funny? I don't even have a problem with my grandmother because I knew my great grandmother and that's what she did, yeah.
B
You saw, she inherited that.
A
She was the emotional foundation of every single human being in her life. My mother lost her mother at 5. She grew up in the Soviet Union. Her bathroom was outside. Her father then went to jail when she was 9 for 10 years because he was Jewish in the Soviet Union. All with a smile and positivity. Every single day of her whole life, she told me that I was the greatest and fucking grounded the living shit out of me at every turn when I wasn't. My greatest pure accountability yet. Zero dent in my self worth. Pure. Do you understand? You are a mother. To walk a tightrope, to create a child who has 100% self love and confidence while equally being 100% accountable and self aware, that is a fucking tightrope.
B
That is. I speak from experience. That is a tightrope.
A
Because you know, you know this. Cause if you want to make your kid, you know, you know, you grew up in the parenting generation. I'm in the parenting generation where you're like, you instill confidence. You could be anything. No, you can't. Parents, no one can be everything if you tell your kid you can be everything. Let me tell you how it plays out. This might help everybody to know where I stand. The reason I have my opinions is because they're not my opinions. I am in the receiving end for now over 15 years, over 10 years. I'm now on the receiving end for over 10 years of over 50,000 direct messages a week, predominantly from 15 to 35 year olds. Let me give you the news alert of the outcome of telling your kids over and over that they can be anything. They think you're full of shit. Your kids think you're full of shit. When you tell them they can be anything. When you look the other way, when they suck, when you go yell at a teacher to give them an A. Yeah, how about this one? When they're 25 and you pay for their shit, they think that you think they're a loser. And even though they're asking for it at every turn, this is real shit we got to talk about.
B
That's right.
A
This is real shit.
B
Yes.
A
People love to blame social media for all the problems. This is not social media. This is misguided empire first world problems of modern parenting that overcorrected to the parenting we were parented with. Daddy gave me no love, so I'm gonna give disproportionate love when the answer was the middle. You want the middle. But you went over here and that's why we have kids that are zoo animals.
B
We create monsters.
A
And by the way, I have no judgment on the kids. I'm empathetic. Now at some point, when the kid is now 30, and I'm like, yo, when are we doing this? Is it 30? Is it 37? Is it 42? Is it 18? When are you allowed to become a grown up? Is my big debate to everyone. I love this, by the way. My grandmother was shitting on my great grandmother in her 60s. I'm like, Grandma, when are you gonna be grown? Yeah, when are you gonna stop dwelling?
B
Yeah.
A
My dad lost his dad at 15. My grandmother said she was a widow eight times a day, every day of her life, as if she was the only widow on earth. And I deeply love my grandmother. I love my grandmother Esther. My sister's so pissed at me right now, listening to this because she loves Grandma Esther more than I love Grandma Esther because she sees herself and Grandma Esther.
B
Oh, yes.
A
These are real things. And this is the. For everybody who's listening, these are the conversations because all of us are looking at the thing and not the root cause.
B
I agree with you over and over. And. And they say there's no real business problems in business. There's only people problems.
A
There's only people problems. And this is real stuff. And you know what's crazy? Here's why I'm so motivated. If one person got pushed into the corner by the last 15 minutes of my rant and was like, it's so worth it. No, no, no. If one person's like, ugh, fuck him. He's right. If this is the moment, they're like, fuck it. I'm going thumbs in instead of fingers out. Well, this was a good use of my time.
B
That's right. It was so. That's what I mean, it was so worth it. It was so worth the time spent if somebody decides I'm going in on it.
A
I mean, I'm sure this is what was intoxicated. I know for fact that if I didn't have an entrepreneurial DNA bone in my body, that I would have been a guidance counselor, a therapist. Like, this is so rewarding. When you were. This is why my mom does it too. Like, why she was the person in her world. The reward of helping someone get happier.
B
Oh, my God.
A
Is the most intoxicating reward. There's no zeros in your bank account. That is better than.
B
I agree.
A
I mean, I have people come up to me whispering in my ear at events that I took them from the brinks of suicide. What? Check do you think exists that's gonna make me feel better.
B
That's right.
A
For what? To buy another vase?
B
I know.
A
For what. We become so materialistic. We become so. Ugh.
B
And it's so empty in the end. It's so empty. Gary, having you here has been.
A
Don't leave yet. I have a question. Oh, I have going in there because I have another minute or two.
B
Okay, good.
A
Real quick. Cause I'm so curious. Cause I've been so excited. This has been so fun. What didn't we touch on that you did want to touch on before we got here. Cause we went into a bunch. I know how I can get. Yeah. Look, look, look. What didn't we touch on?
B
What didn't we touch on was. Well, I think that you've touched on this because of your personality. So I didn't even get to it. But let me ask you this one thing that I have here is when it comes.
A
I'm sorry. Before you do that. Yeah. I just remember one thing. Sorry everybody. This is how my brain works. I love it.
B
Now we're good.
A
My mother didn't tell me how to live. She showed me how to live.
B
Yeah. Yeah.
A
That's it.
B
The role model who doesn't have to say it in the words. It's just by the way they live always.
A
She also. I'll give you mom's one tactic. She hyper glorified things I did that were kind aw. Opening a door for an old lady at 8 I talk about a lot the way I manned up for my sister. She would go crazy and like the character quality pieces. Uh huh. You know. And you know this. We're all. I can see everybody behind the cameras tonight. We react to what our parents are cheering for. Yes. Too many parents cheer for straight A's in school. Bad.
B
That's right.
A
My mom cheered for when I was kind to an elderly woman.
B
Good quality of the character is what I've cheered for grades I'm. That doesn't speak too much for me.
A
No. All right. So what you were about to say.
B
So if you were to pick and I know you're gonna say, well both. It depends. Sometimes I think I know what your answer is to this but I'm curious. Let's see if it was only one or the other.
A
Yes.
B
Would you say it is strategy or identity that of the person and the entrepreneur like me. You. What do you think really makes the person really successful? Strategy or their identity?
A
I would say definitely not strategy. Let me. You know I'm thinking through identity. But I Don't think it's that either.
B
I'll say more.
A
I. In my observation of success, and maybe this is how you define identity. I would say that I have the most direct correlation to financial, but more importantly emotional success towards self awareness and self acceptance. And that might be identity. It's definitely not strategy. No, strategy is school. Yeah, like, oh, I'm gonna do that. That's nice. No, no, because by the way, no one. Do you know why most people. Oh, this is good. I'm glad we got this. Do you know why most people listening have not been able to execute on their strategy?
B
Why?
A
Because they're not good. They're not good.
B
Always about in here.
A
Because you don't have enough energy to get through your strategy. If you're not good.
B
That's right.
A
You'll die along the road. So I don't know if identities, the way I'm talking about self awareness and self acceptance.
B
It is. It is. That's.
A
Then I would say, then it's definitely in the way you're framing it. Then I would say it's identity. How do you put yourself in a position to have the least friction day to day, to be in your most true self, to be able to be adaptable and emotionally strong enough to deal with the unlimited shit want must deal with to actually get to the top?
B
Well, this is it. And the higher you go, the more shit you deal with, I think.
A
Oh, my God. I know it's not politically correct to quote Diddy, but like, in the words of Diddy and Biggie, more money, more problems. Like the way you go. I mean, I. Do you know what. Do you know what I write out for occupation? Literally when I have to fill out a form? Occupation. Do you know what I write? No, what? Firefighter.
B
Oh, my God. Just putting out fires all day long.
A
My whole life is shit on, shit on, shit on, shit on, shit on, shit with the occasional smile.
B
This is refreshing to hear as an entrepreneur.
A
Good.
B
The bigger things get, the more fires I feel like I'm putting out. And there are moments where I question, are we doing something wrong that I'm putting out more fires or is this a result of the growth we're having?
A
By the way, you know who most understands this? All the moms that are listening. The fuck is being a mom honestly? Shit on, shit on, shit on, shit on, shit with the occasional smile.
B
So true.
A
But that smile's worth everything. It is, it is.
B
Gary, thank you so much. This moment was worth everything. Thank you so much for being here, everybody.
A
If you enjoyed this podcast. Please go back and look at the prior episodes. They're loaded. I appreciate your attention and thanks for being part of this journey. See you later.
Date: January 14, 2026
Host: Gary Vaynerchuk (GaryVee)
Guest Host/Interviewer: Amanda (implied from context)
This episode centers on what truly hinders people's success, especially focusing on authenticity, self-awareness, the dangers of regret, and the myths around ambition, age, and overnight success. Gary and Amanda dive into candid reflections about self-limiting beliefs, the role of upbringing, societal expectations, and the importance of identity over strategy in achieving meaning and success. The discussion is loaded with not just business advice, but deep psychological and philosophical insights relevant to anyone seeking positive change, regardless of age or background.
"You will not trick the world eventually." (01:29, Gary)
“Money, success, notoriety, and fame is a 100% amplifier and exposer of your truth.” (02:17, Gary)
“When I make a piece of content... I’m just thinking, man, I really hope that when I post this video, three people... are finally ready to tip.” (06:16, Gary)
“Speak to the person you know who needs to hear this.” (07:05, Amanda)
“I have no interest in the perception. I’m not even there for the reality. Meaning everything I want to happen will happen if I continue to provide value. The end.” (08:31, Gary)
"From 14 years old to 22, I worked at my father’s liquor store for two to five dollars an hour, every weekend, every vacation." (09:24, Gary)
“The only version of regret that I have… I can taste it.” (14:08, Gary)
“I’m gonna build the largest sandcastle at the beach…and at the end of the day, when my parents call me to eat, I’m gonna break it down. Cause it’s not about the castle. It was about all day at the beach, building the castle, the experience. That’s it.” (14:41, Gary)
“Good news, all the guys are like that too…It’s not a girl boy thing. It’s a self-esteem thing.” (18:17, Gary)
“There are so many women right now that are not willing to jump because they’re worried about the impact on their insecure husband.” (21:46, Gary)
“I predict in 20 years, when I turn 70, it’s gonna be the era of the 70 year old.” (22:38, Gary)
“Go donate 5 hours to a retirement home...what they will give you has the deep potential to change the course of your life.” (23:18, Gary)
“Instead of being mad at your dad who never said, I love you…and using that as a 48 year excuse, how about showing compassion to your dad in realizing he didn’t love himself?” (32:32, Gary)
“Every bad thing that has ever happened in my life is 100% attributable to my inability to be canderous with the people I like the most.” (37:10, Gary)
“We have become infatuated at looking at 150 people and forgetting that…there are 8.3 billion people on earth.” (41:39, Gary)
“My mother didn't tell me how to live. She showed me how to live." (56:29, Gary)
“To walk a tightrope, to create a child who has 100% self-love and confidence while equally being 100% accountable and self-aware, that is a fucking tightrope.” (51:30, Gary)
“I would say definitely not strategy...I would say that I have the most direct correlation to financial, but more importantly emotional success towards self-awareness and self-acceptance...It’s definitely not strategy.” (57:47-58:46, Gary)
“Do you know what I write out for occupation?...Firefighter. My whole life is shit on, shit on, shit on, shit on, shit with the occasional smile.” (59:40, Gary)
“All the moms that are listening. The fuck is being a mom honestly? Shit on, shit on, shit on, shit on, shit with the occasional smile. But that smile’s worth everything.” (60:00, Gary)
On Authenticity and Fame:
“Fame and success don’t change you, they expose you.” (02:07, Gary)
On Regret:
“The only version of regret that I have… I can taste it.” (14:08, Gary)
On Gender and Entrepreneurship:
“There’s this misconception like, ah, guys… will never be scared to… stand up. It's not true… It's a self-esteem thing.” (19:06, Gary)
On Parenting:
"My mother didn’t tell me how to live. She showed me how to live." (56:29, Gary)
“To create a child who has 100% self-love and confidence while equally being 100% accountable and self-aware, that is a fucking tightrope.” (51:30, Gary)
On the Value of Age:
“We’re getting close…to the era of the 70-year-old. I think wisdom…is life smiling down at me.” (22:38, Gary)
On Success Equation:
“You think that’s part of the equation? No, no, I think it’s the equation.” (15:26, Gary, on not caring about trophies)
On Candor:
“Every bad thing that has happened in my life is...attributable to my inability to be canderous with the people I like the most.” (37:10, Gary)
On Losing:
“If you have a kid that falls in love with losing, very good things will happen. I fell in love with losing, which is why I'm not scared of anything.” (44:57, Gary)
On Identity Over Strategy:
“It’s definitely not strategy… It’s identity—how do you put yourself in a position…to be your most true self, to be adaptable and emotionally strong enough to deal with...to actually get to the top?” (58:46, Gary)
Concluding Wisdom:
“The reward of helping someone get happier is the most intoxicating reward. There’s no zeros in your bank account...that’s better than that.” (55:25, Gary)