The #1 Thing Stopping You from Success

Summary

The GaryVee Audio Experience

Episode: The #1 Thing Stopping You from Success

Host: Gary Vaynerchuk
Guest: Amanda (psychologist, podcast host)
Date: May 1, 2026

---

Episode Overview

This episode focuses on dissecting the single most important barrier to personal and professional success, according to Gary Vee: an individual's own mindset—specifically, self-awareness, self-acceptance, and the willingness to let go of fear and others’ opinions. Through a candid and energetic conversation with Amanda, a psychologist and coach, Gary shares stories from his upbringing, the realities of building businesses, the truths about fame and fulfillment, and actionable advice for listeners, especially women and parents. The tone is authentic, fast-paced, and direct, packed with “real talk” and memorable moments.

---

Key Discussion Points & Insights

1. Authenticity, Consistency, and Self-Parenting

[01:04–04:43]

• Amanda shares her gratitude for Gary’s authenticity and kindness behind the scenes.
• Gary attributes his character to his upbringing:

  "I'm proud of my consistency...It's a compliment to my parenting, the way I was parented." — Gary Vee [02:29]

• Their mutual agreement on authenticity:

  "You will not trick the world eventually. Money, success, notoriety, and fame...is a 100% amplifier and exposer of your truth." — Gary Vee [03:17]

• Not everyone will like you if you’re real; being misunderstood is inevitable:

  "There’s some ways to misunderstand me. Anyone who's consumed me for enough feels that way." — Gary Vee [05:20]

2. The Cost & Power of Authenticity

[05:24–09:14]

• Authenticity as a double-edged sword: it either repels or attracts.

  "It's like the definer of...the ultimate equalizer." — Amanda [06:30]

• Gary on the uncomfortable honesty he shares:

  "One of the reasons people struggle with me is I'm poking their zit...At what age is it appropriate to stop blaming your parents?" — Gary Vee [06:40]

• He focuses on impact, not numbers:

  "I hope three people are changed...today is their day that they take their leap for themselves." — Amanda [08:05]

• Both agree: serve with value even if it's just for one person.

3. Selfless Consistency in the Zero-Audience Days

[08:29–10:04, also throughout]

• Amanda’s story of going “Live” 365 days in a row, even when only one person showed up.
• Gary explains consistent value creation is more important than vanity metrics.

  "I'm not even there for the reality. Everything I want to happen will happen if I continue to provide value. The end." — Gary Vee [09:32]

4. Gary’s Unorthodox Entrepreneurial Journey & Mindset

[10:04–16:20]

• Gary’s story: from stocking shelves for low wages at his father’s liquor store for 20 years to building a $60M family business—all before starting his own "career" at 34.
• Immigrant ethic and gratitude shaped his worldview.
• He warns against regrets from sacrificing all leisure in his youth:

  "The only version of regret that I have...in my late 30s, early 40s, I'm like, Ugh, I blew it." — Gary Vee [16:03]

5. Success, Ambition & the Equation for Achievement

[16:23–19:08]

• Gary’s sandcastle metaphor:

  "I'm gonna build the largest sandcastle at the beach...but it's not about the castle. It was about all day at the beach." — Gary Vee [16:23]

• The KEY insight for success:

  "It's very easy. I have it because I didn't give a shit...I think it's the equation." — Gary Vee [17:10]

• There are two ways “to the tippy top”: confidence/simplicity or insecurity. The former builds lasting happiness; the latter, Darth Vader-like outcomes.

6. Age, Gender, and “Too Late” Myths for Women

[19:08–24:59]

• Amanda details the struggles women, especially in midlife, face with self-belief.
• Gary debunks the myth that men are naturally more confident:

  "Good news, all the guys are like that too...It's not a girl-boy thing. It's a self-esteem thing." — Gary Vee [20:24]

• The real barrier: caring too much what others think, living as if still in high school.

  "When are you ready to not live in high school?...They are not interested in living their most true, happy life...because they're worried about the opinion...often their spouse." — Gary Vee [22:19–23:29]

7. Ageism, Wisdom, and the Value of the Elderly

[24:59–29:29]

• Wisdom of elders is undervalued. Gary recommends everyone spend time with people 70 and older.

  "What they will give you has the deep potential to change the course of your life." — Gary Vee [25:00]

• Shared stories from both about formative experiences with elders.
• Gary:

  "When you're 80...you don’t give a fuck...I’ve been 80 since I was 6.” — Gary Vee [28:40]

8. Regret, History, and Context for Suffering

[29:29–31:28]

• Stories of regret from 85-year-old women center on not taking chances.
• Each generation faces unique challenges, but things generally get better:

  "I'm not depressed because I know it’s better. Of course, it’s not better in every situation...But we spend all our time dwelling and being scared." — Gary Vee [30:58]

9. Fear, Criticism, and Internal Motivation

[31:28–34:09]

• Parents often pass down fear unwittingly.
• Tuning out the opinions of strangers (and loved ones) is critical. Most criticism comes from unhappy people, not the proverbial “freak in the basement.”

10. Entitlement, Family Dynamics, and Candor

[34:09–43:22]

• Deep dive into the entitlement of modern children and the family business experience.
• Gary’s vulnerability: his lifelong struggle with candor; it’s his self-professed “kryptonite.”

  "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." — Gary Vee [39:18]

• His journey to practicing “Kind Candor,” giving clear feedback early and compassionately.

11. Overnight Success, Losing, and Parenting

[43:22–49:55]

• Debunking overnight success (“they’re fucking delusional. There are 8.3 billion people on Earth”).

  "If your beauty standards are someone who has spent $3.7 million on plastic surgery, the fuck are you talking about?" — Gary Vee [44:39]

• Losing and failure should not be demonized:

  "Winning and losing is real...but here’s the secret: Losing is good." — Gary Vee [47:27]

• Overinvolved and ego-driven parents damage kids’ resilience; outcomes aren’t all in parents’ control.

12. The Impact of Mothers (and What Really Matters in Parenting)

[49:55–60:00]

• Amanda asks what made Gary’s mom so impactful.
• Gary’s emotional tribute:

  "It had very little to do with what she said. It had everything to do with what she did...To create a child who has 100% self love and confidence while equally being 100% accountable and self aware. That is a fucking tightrope." — Gary Vee [54:10]

• He calls out the pitfalls of over-coddling versus harshness, advocating for the “middle path.”

13. Identity vs. Strategy in Success

[60:01–62:28]

• Amanda: “If it was only one or the other: strategy or identity, what really makes a person successful?”
• Gary:

  “Definitely not strategy...I have the most direct correlation to financial—but more importantly emotional—success towards self-awareness and self-acceptance.” [60:26, 61:04]

• Why most people fail to execute: lack of inner strength and self-acceptance, not poor strategies.

14. Entrepreneurship & Motherhood: Parallel Journeys

[62:28–62:53]

• Gary:

  “My whole life is shit on, shit on, shit on with the occasional smile. All the moms who are listening understand this.” — [62:22]

---

Notable Quotes & Memorable Moments

• On Success: “I have it because I didn’t give a shit...I think it’s the equation.” — Gary Vee [17:05–17:13]
• On Regret: “You want to mitigate against regret. When you talk to an 85-year-old, they’ll talk about what they regret, not what they did.” — Gary Vee [29:27]
• On Parenting: “It had very little to do with what she said. It had everything to do with what she did.” — Gary Vee [51:10]
• On Candor: “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.” — Gary Vee [39:18]
• On Living for Yourself: “When are you ready to not live in high school?” — Gary Vee [22:19–22:28]
• On Loss and Growth: “Losing is good. If you have a kid that falls in love with losing, very good things will happen.” — Gary Vee [47:36]
• On Maternal Influence: “To create a child who has 100% self love and confidence while equally being 100% accountable and self aware. That is a fucking tightrope.” — Gary Vee [54:10]

---

Timestamps for Important Segments

• [03:17] Fame & money as amplifiers of character
• [09:10] Changing lives one person at a time
• [13:00] Gary describes his grueling two-decade family business grind
• [16:23] Sandcastle metaphor for achievement
• [17:10] The “not caring” equation for success
• [22:19] "When are you ready to not live in high school?"
• [25:00] Wisdom from elders; the value of spending time with those 70+
• [30:58] History and perspective on fear (electricity, AI)
• [39:18] Gary’s lifelong struggle with candor
• [46:38] The dangers of indifference and sixth-place trophies
• [49:55] Parenting and self-worth: the impossible tightrope
• [60:26] Identity/self-awareness vs. strategy for long-term success
• [62:22] Being a founder or a mom: "shit on, shit on...with the occasional smile"

---

Key Takeaways

• Self-awareness, self-acceptance, and authenticity are the true unlocks for success.
• Consistency and value matter far more than chasing followers or external trophies.
• Regret comes not from what you do, but what you are too scared to try.
• Parenting is about modeling and instilling both self-love and accountability, not perfection.
• Letting go of “high school” opinions—family, public, social media—is crucial to living fully.
• Lasting fulfillment comes from helping others, not material gains, popularity, or even your own achievements.
• No matter where you start—from $2/hour in a liquor store to “overnight” fame—the internal journey determines everything.

---

This summary captures the spirit, lessons, and voice of the episode, complete with key quotes and timestamps for quick reference. Whether you’re a first-time listener or a regular GaryVee fan, you’ll find actionable insights and plenty of Gary’s signature straight talk.

Transcript

[Amanda]

When you need to build up your team to handle the growing chaos at work, use Indeed Sponsored Jobs. It gives your job posts the boost it needs to be seen and helps reach people with the right skills, certifications and more. Spend less time searching and more time actually interviewing candidates who check all your boxes. Listeners of this show will get a $75 sponsored job credit@ Indeed.com podcast. That's Indeed.com podcast. Terms and conditions apply.

[Gary Vee]

Need a hiring hero?

[Amanda]

This is a job for Indeed Sponsored

[Gary Vee]

Jobs get business done with the new American Express Graphite Business Cash Unlimited card with unlimited 2% cash back on all eligible purchases, unlimited 5% cash back on flights and prepaid hotels booked through American Express Travel Online and a flexible spending capacity that can grow with your business. You'll have the confidence to keep building. Apply today and earn a welcome offer of $1,500 cash back after you spend $50,000 in qualifying purchases on your new card within the first six months of card membership terms. Apply. Learn more at Go Amex Graphite and this is the GaryVee audio experience.

[Amanda]

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.

[Gary Vee]

I'm beyond happy to.

[Amanda]

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.

[Gary Vee]

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 like my consistency is something I'm incredibly proud of. It's also the thing I do that's

[Amanda]

Easiest just being yourself.

[Gary Vee]

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.

[Amanda]

I think the fact you held onto it. You didn't let all the fame and success.

[Gary Vee]

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.

[Amanda]

So it's an amplifier of the core of you.

[Gary Vee]

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.

[Amanda]

I always believe money is an amplifier, but it's this conversation that's connecting it for me. So would fame be right?

[Gary Vee]

Oh, for sure. Power. Power. A true.

[Amanda]

And what do you do with that power? Right.

[Gary Vee]

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.

[Amanda]

You'll never get over it.

[Gary Vee]

I don't think I will at this point. I'm like, okay, I think so.

[Amanda]

And that's why I think everybody of all ages and walks of life love you so much.

[Gary Vee]

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.

[Amanda]

I agree.

[Gary Vee]

Anybody who's gotten a flash of me, oh, there's. There's some ways to misunderstand me.

[Amanda]

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 for 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.

[Gary Vee]

Yes.

[Amanda]

Or attracts them. It's like the definer of. My producer always says, she's like, you're the ultimate equalizer.

[Gary Vee]

If someone is an exposer.

[Amanda]

Yes. The thing you can't really hide.

[Gary Vee]

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?

[Amanda]

Yeah, it's a great question.

[Gary Vee]

You 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.

[Amanda]

Right, right. And what makes you think I would want to hire you as well? Like that? You haven't worked through that.

[Gary Vee]

Yeah.

[Amanda]

Now, I'm gonna come to you. If you are somebody who is trying to sell a service or a good.

[Gary Vee]

I'm like, oh, and 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 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 set, anyone? But today's the day.

[Amanda]

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.

[Gary Vee]

Yeah.

[Amanda]

And I told you, my kids were telling you, they helped me set up on social media, Got a light, a shitty ring light and 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. 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.

[Gary Vee]

That's why it happened.

[Amanda]

And I didn't quit showing up even when there was a low audience.

[Gary Vee]

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.

[Amanda]

Yes, yes, got it right. Exactly.

[Gary Vee]

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 the. 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.

[Amanda]

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 this?

[Gary Vee]

No, no, I'd love to appease the conversation. Yeah, 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.

[Amanda]

So your friends are going off doing

[Gary Vee]

fun things and you're working 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,

[Amanda]

you could already see things.

[Gary Vee]

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 going to 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 Soviet, 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 by just getting us to America. And then I had this mother that was so uncomfortably great that I'm just cooking with gas of 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 build my dad's business from a 4 million to a $60 million business and. And never made $100,000 a year.

[Amanda]

Oh, my.

[Gary Vee]

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. Oh, 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 know me now, they're like, I was talking about something like, yeah, Gary, 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 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. He. 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.

[Amanda]

Tell me, what are the dynamics there?

[Gary Vee]

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. 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 did

[Amanda]

that come back to represent itself later in life? Ready to soundtrack your summer with Red Bull Summer All Day Play. You choose a playlist that fits your summer vibe the best. Are you a festival fanatic, a deep end dj, a road dog, or. Or a trail mixer? Just add a song to your chosen playlist and put your summer on track. Red Bull Summer All Day Play. Red Bull gives you wings. Visit red bull.com brightsummer ahead to learn more. See you this summer.

[Gary Vee]

Now at McDonald's. A McDouble is $2.50. So you can get your gym gains on or just get lunch for only $2.50. Get more value on the under $3 menu. Limited time only. Prices and participation may vary. Prices may be higher for delivery. The only version of regret that I have, you know, I think regret is a poison. And I'm like wasted energy. And honestly, I'm like, so lucky. Like, it's so minor.

[Amanda]

Yes.

[Gary Vee]

But I can taste it.

[Amanda]

Yes.

[Gary Vee]

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, Ugh, I blew it. You know, like. And that's not in my framework.

[Amanda]

Right.

[Gary Vee]

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?

[Amanda]

No. What about the person who's like. Well, it's easy for you to say, Gary. Cause you have it.

[Gary Vee]

Very easy. I have it because I didn't give a shit.

[Amanda]

Oh, so you think that's part of the equation?

[Gary Vee]

No, no, I think it's the equation.

[Amanda]

Oh, my God, Even better. It's the equation.

[Gary Vee]

It's the. Okay, 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 and 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.

[Amanda]

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?

[Gary Vee]

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.

[Amanda]

Oh, that is such a telltale, isn't it?

[Gary Vee]

I think so.

[Amanda]

And when it's all said and done, how many people are really there for you? Because if you had to 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.

[Gary Vee]

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. Yeah, mazel tov. Knock yourself out.

[Amanda]

Right?

[Gary Vee]

Just not for me, right?

[Amanda]

Not the way you're gonna build it.

[Gary Vee]

No.

[Amanda]

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, course, who are following me, who've hired me, who come up to me on the streets in New York, it's all from the 20s into their 80s.

[Gary Vee]

Yes.

[Amanda]

But I would say a good Mass majority is 35 to 55. Who is probably watching.

[Gary Vee]

I love those ladies.

[Amanda]

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 have 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 until I was. I was just turning 48.

[Gary Vee]

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. Yeah. 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.

[Amanda]

Yes.

[Gary Vee]

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.

[Amanda]

Yes.

[Gary Vee]

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. And I. Cause I hang. I mean, I'm part of a bunch of women groups.

[Amanda]

Yeah.

[Gary Vee]

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. Like these, you know, the girl talk is the funnest for me. Cause I'm half girl. 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 this 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.

[Amanda]

Yes, yes.

[Gary Vee]

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.

[Amanda]

Right.

[Gary Vee]

So what do I say to them? Say a couple things. One, ladies, when are you ready to not live in high school?

[Amanda]

Oh, Gary. Yes, yes.

[Gary Vee]

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 johnnypants49's comment or. The misery loves company people in their life, Often their mother, often their father, often their siblings off in their spouse. There's. So let's talk about the ladies. There's so many women right now that are not willing to jump because they're worried about the impact on their insecure husband.

[Amanda]

Oh, I know that. I deal with this.

[Gary Vee]

I'm sure.

[Amanda]

Oh, I deal with this all the time. All the time.

[Gary Vee]

I'm sure you do.

[Amanda]

It's usually the husband, he's gonna be threatened by me doing something, taking up space that's not paying attention or being

[Gary Vee]

more financially successful than him.

[Amanda]

Oh, that's a big one.

[Gary Vee]

Massive.

[Amanda]

I know. My husband's like, it's the greatest thing in the world. Like, this is a dream come successful. It's 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. It's all real because they are so terrified that nobody cares about a 50, a woman 50 and over speaking in

[Gary Vee]

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.

[Amanda]

I do too.

[Gary Vee]

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 on 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.

[Amanda]

I could not agree with you more.

[Gary Vee]

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.

[Amanda]

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. And in people that age and change. And I don't know why the rest of the world is not seeing it.

[Gary Vee]

I agree.

[Amanda]

It's just some of the most beautiful years of my life were spent.

[Gary Vee]

I would argue, without knowing much about you, that it might be the most significant thing that ever happened to you.

[Amanda]

I really would say it was one of the stamps on my heart that fundamentally changed the woman I am.

[Gary Vee]

Yep.

[Amanda]

And it was talking to people in their 70s, 80s, 90s, and I was on the Alzheimer's wing. And so 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 to like, oh, stuff.

[Gary Vee]

Oh my gosh.

[Amanda]

And the stories they would tell.

[Gary Vee]

Can I tell you a story?

[Amanda]

Yes, please.

[Gary Vee]

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 grand. My great grandparents, my grandmother, my parents, myself. And occasionally because 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.

[Amanda]

Oh, I don't give a fuck at 53.

[Gary Vee]

Me neither.

[Amanda]

I am so uncensored.

[Gary Vee]

I haven't given a fuck for a very long time. And I definitely don't give a fuck. I just turned 50. 50, but you really don't give a fuck at 83. You know what I mean? We will give less fucks at 83. We 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

[Amanda]

on what she regrets?

[Gary Vee]

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 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, you know what I mean? 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.

[Amanda]

Like that of what my grandmothers could never do. Oh my God. Very less than ideal marriages because they had no skill sets. They couldn't.

[Gary Vee]

How about the law?

[Amanda]

I know.

[Gary Vee]

What do we forget about?

[Amanda]

Even get a checking account.

[Gary Vee]

Neither one of them correct.

[Amanda]

Until the year I was born.

[Gary Vee]

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. Yeah, 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.

[Amanda]

No, no, D's and F's actually means you's an F's.

[Gary Vee]

But I was good at history. And I think that one of the things that keeps me happy, like AI.

[Amanda]

Yeah.

[Gary Vee]

I'm not worried about AI because I know the history of electricity. Electricity was demonized and was gonna ruin the world.

[Amanda]

I literally was just talking about this yesterday. I can't believe I use electricity as the example.

[Gary Vee]

So I'm, you know, I'm not depressed because I know it's better. Of course it's not better in every situation.

[Amanda]

It's just how we use things.

[Gary Vee]

It's just we spend all our time dwelling and being scared. And then people have 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.

[Amanda]

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. What are you doing?

[Gary Vee]

Yeah, yeah.

[Amanda]

Why are you talking to the camera? Like strangers are gonna.

[Gary Vee]

Yeah.

[Amanda]

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 telling her mom about, but she. My mom has operated. And I love her so much, but she's operated so much from place of fear.

[Gary Vee]

Of course she has.

[Amanda]

The end. 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 freak.

[Gary Vee]

You have to hear this. And sometimes it's not a freak in the basement, no. But like, no, no.

[Amanda]

They say to me, no, no, no, no.

[Gary Vee]

I think you're right. 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. By the way, I literally did a live today on TikTok and somebody was like, man, you haven't aged well. You really ragamy. 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.

[Amanda]

I know, I know the message means more than the lighting. I remember the. I know. Now my producer's on my ass all the time about lighting.

[Gary Vee]

Yeah, listen, listen, there's.

[Amanda]

I know.

[Gary Vee]

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. 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.

[Amanda]

That's it. That's it.

[Gary Vee]

Like, no shit. You don't say I love you to others. You don't love yourself.

[Amanda]

You can't extend what you don't already have or feel.

[Gary Vee]

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 and realizing he didn't love himself.

[Amanda]

This episode is brought to you by State Farm. You know those friends who support your preference for podcasts over music on road trips? That's the energy State Farm brings to insurance. With over 19,000 local agents, they help you find the coverage that fits your needs so you can spend less time worrying about insurance and more time enjoying the ride. Download the State Farm app or go online@state farm.com like a good neighbor. State Farm is there.

[Gary Vee]

Where is Daredevil?

[Amanda]

I'm right here.

[Gary Vee]

Don't miss the return of Marvel Television's Daredevil Born Again.

[Amanda]

So what's next?

[Gary Vee]

I feel liberated. We're going to take this city back over medicated in an all new season. Now streaming only on Disney plus.

[Amanda]

They're hunting us. It's time we started hunting them.

[Gary Vee]

I can work with them.

[Amanda]

This should be tons of fun.

[Gary Vee]

Marvel Television's Daredevil Born Again now streaming only on Disney plus.

[Amanda]

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 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 ladders, right?

[Gary Vee]

You're asking for something they can't sell you.

[Amanda]

They don't have it. So it wasn't against you. They don't even have it for themselves. They've never carried it. How would you think they would offer it to you?

[Gary Vee]

Because people lack the humility. People lack the detachment.

[Amanda]

Yeah.

[Gary Vee]

People don't realize they're completely self infatuated.

[Amanda]

That's a big one.

[Gary Vee]

I think so.

[Amanda]

It's really. It's the bane of my existence sometimes with some of these people.

[Gary Vee]

Right? Like, like, what do you mean? Your dad? Well, you know, what about your dad, which. What did you do for your dad? How about that? That's a good one. That's one that I haven't even like, really, like pushed enough on. Like, where are we at here, everyone? This is like, yeah, like, like this. This whole concept of like the entitlement of childhood is fascinating.

[Amanda]

All right, let's go. Because I.

[Gary Vee]

Someone birthed. Hold on now I'm getting hyped.

[Amanda]

Yeah, yeah.

[Gary Vee]

Someone fucking birthed you. Yeah. And then you're like, do more. They did enough.

[Amanda]

Yeah. They gave you life.

[Gary Vee]

400 trillion. Do you know this? It's 400 trillion. Current science has it at 400 trillion to 1. The likelihood of becoming a human. Yeah. So let me get this 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?

[Amanda]

Isn't that enough?

[Gary Vee]

That's the. Yeah, this is. We need to change. How about what? By the way, I think this comes natural to me because I talked about it early in the podcast. I thought about what I'm going to do for them at 14, 15, I'm like, I'm better. Instead of what normal kids do. And I say normal. Oh, 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 to spend three hours a day being his therapist while I was building the business, I would have built a hundred million dollar business for him.

[Amanda]

I believe it.

[Gary Vee]

I have a lot of practice in therapy. It's called having my dad.

[Amanda]

I love this. I want to talk about.

[Gary Vee]

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, 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.

[Amanda]

Wow. How beautiful is that? And so beautiful he was able to receive that leadership.

[Gary Vee]

Well, 20 fucking five years later, with all due respect and 700 trillion hours of fighting, you know, But Ish. Because you know, this. It's just a band aid. Ish. It's just. Everybody has a ceiling.

[Amanda]

Yeah.

[Gary Vee]

Let me talk about a vulnerab. Instead of being like, I'm so. Yeah, 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.

[Amanda]

Okay.

[Gary Vee]

I will only ever in my lifetime get to so great at candor.

[Amanda]

Why is that?

[Gary Vee]

Cause it 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.

[Amanda]

Wow. Wow. Is it still plaguing you?

[Gary Vee]

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.

[Amanda]

Okay.

[Gary Vee]

Right.

[Amanda]

Do you think it's something you're gonna be able to work through?

[Gary Vee]

Of course. 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 eight, nine, ten out of most emotional things. 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 Vayner, 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.

[Amanda]

You just told them, like, you sucked.

[Gary Vee]

No, I wish I did. Oh. 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 a. 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, you know, Monday. And then. No, no, no, no. Monday, Friday, be like, johnny, have the best weekend. Good job on this. And Monday. Hey, John, you got two minutes? I'm like, hey, so you probably know Johnny, like, we got. 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 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.

[Amanda]

Okay?

[Gary Vee]

We're going to tell you, but we're going to do it in a very humane, very 360, very thoughtful way. And the intent is that this Candor allows us to fix it.

[Amanda]

So you can stay.

[Gary Vee]

Not set it up to fire you.

[Amanda]

Right, but if, in fact, it is not remedied, then. Yes, exactly.

[Gary Vee]

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 the way I feel about training. Compared to six months, I feel close. Yes, it gets harder.

[Amanda]

Yes.

[Gary Vee]

And then forget about training. Sid. 10 years or Kaylin or Marcus. They're fucking family to me.

[Amanda]

Yeah.

[Gary Vee]

And that's when it gets hard.

[Amanda]

It does. It really, really does. I agree with you.

[Gary Vee]

So that's something I continue to put out publicly 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.

[Amanda]

Enemy. Yeah.

[Gary Vee]

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's still got it in him. It's work.

[Amanda]

Like, you're doing me wrong. You don't really care about this business,

[Gary Vee]

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.

[Amanda]

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. 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.

[Gary Vee]

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.

[Amanda]

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. If it can, considering the large population in the world.

[Gary Vee]

Your husband's very right on this.

[Amanda]

Why do you keep focusing on.

[Gary Vee]

It is hard work if your beauty standards are someone who has spent $3.7 million on plastic surgery. The fuck are you talking about?

[Amanda]

It's so true.

[Gary Vee]

If your 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?

[Amanda]

That's right.

[Gary Vee]

About 800. Let me say it slow, if I may.

[Amanda]

Yes.

[Gary Vee]

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?

[Amanda]

Oh no shit.

[Gary Vee]

No shit. So 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.

[Amanda]

I love that.

[Gary Vee]

That's what I actually think is happening. I think they're wah wah wah to their parents. Cause 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, 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.

[Amanda]

Yeah.

[Gary Vee]

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.

[Amanda]

Yeah.

[Gary Vee]

I didn't do shit. I played Madden Spades. Cee Lo hooked up like, like go.

[Amanda]

Yeah,

[Gary Vee]

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, 6th place trophies has destroyed our society.

[Amanda]

I've heard you say this before. I'm obsessed with this, happy that you say this.

[Gary Vee]

Listen to me, everybody. Winning and losing is real. It's called life. But here's the secret. Losing is good.

[Amanda]

Yes.

[Gary Vee]

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.

[Amanda]

That's right.

[Gary Vee]

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, hey, mom, you don't get it. Everyone's getting famous on TikTok, secretly saying, mom, give me a thousand bucks.

[Amanda]

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.

[Gary Vee]

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.

[Amanda]

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.

[Gary Vee]

Oh, you're so brilliant. Good news.

[Amanda]

I don't need them to be successful for my ego or for. So I can show them.

[Gary Vee]

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.

[Amanda]

That's right.

[Gary Vee]

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.

[Amanda]

That's right.

[Gary Vee]

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.

[Amanda]

Yeah. And there's so much nuance that's out of our control. And what our children choose, DNA is real.

[Gary Vee]

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, I don't understand how we're confused by this. 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.

[Amanda]

Yes.

[Gary Vee]

This is about you, with you, about you and you.

[Amanda]

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. Yes, Regularly about your mom. I would love to. I would just love to know what was it about your mom that made. 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?

[Gary Vee]

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 raise 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.

[Amanda]

Yeah, you saw, she inherited that.

[Gary Vee]

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.

[Amanda]

That is.

[Gary Vee]

I speak from experience because you know, you know this. Because 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, 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 even though they're asking for it at every turn. This is real shit. We got to talk about. This is real shit.

[Amanda]

Yes.

[Gary Vee]

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 luck. 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.

[Amanda]

We create monsters.

[Gary Vee]

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? 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?

[Amanda]

Yeah.

[Gary Vee]

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 in Grandma Esther.

[Amanda]

Oh, yes.

[Gary Vee]

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.

[Amanda]

I agree with you over and over again. And they say there's no real business problems in business, there's only people problems

[Gary Vee]

in business, 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.

[Amanda]

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.

[Gary Vee]

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. Rewards of helping someone get happier. It's the most intoxicating reward. There's no zeros in your bank account. That is better than.

[Amanda]

I agree some.

[Gary Vee]

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?

[Amanda]

That's right.

[Gary Vee]

For what? To buy another vase?

[Amanda]

I Know for what?

[Gary Vee]

We become so Matt. Materialistic. We become so. Ugh.

[Amanda]

And it's so empty in the end. It's so empty. Gary, having you here has been.

[Gary Vee]

Don't leave yet. I have a question. Oh, I'm going out there because I have another minute or two.

[Amanda]

Okay, good.

[Gary Vee]

Real quick because I'm so curious because 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 because we went into a bunch. I know how I can get. Yeah, look, look, look. What didn't we touch on?

[Amanda]

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 to.

[Gary Vee]

I'm sorry, before you do that, I just remembered one thing. Sorry everybody. This is how my brain works.

[Amanda]

I love it. No, we're good.

[Gary Vee]

My mother didn't tell me how to live. She showed me how to live.

[Amanda]

Yeah,

[Gary Vee]

yeah, that's it.

[Amanda]

The role model who doesn't have to say it in the words. It's just by the way they live always.

[Gary Vee]

She'll so I'll give her you. I'll give you mom's one tactic. She hyper glorified things I did that were kind awning a door for an old lady at 8. I talk about a lot. The way I manned up for my sister. Like she would go crazy and like,

[Amanda]

you know, and the character quality pieces.

[Gary Vee]

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.

[Amanda]

Yes.

[Gary Vee]

Too many parents cheer for straight A's in school. Bad my mom cheered for when I was kind to an elderly woman.

[Amanda]

Good quality of the character is what I've cheered for. Grades. That doesn't speak too much for me. No.

[Gary Vee]

All right. So what you were about to say.

[Amanda]

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.

[Gary Vee]

Let's see.

[Amanda]

If it was only one or the other.

[Gary Vee]

Yes.

[Amanda]

Would you say it is strategy or identity, that of the person and the entrepreneur, the per like me, you. What do you think really makes the person really successful? Strategy or their identity?

[Gary Vee]

I would say definitely not strategy. Let me. You know, I'm thinking through identity, but I don't think it's that either.

[Amanda]

I'll say more I.

[Gary Vee]

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 is strategy school.

[Amanda]

Yeah. Yeah.

[Gary Vee]

Like, oh, I'm gonna do this. That's nice. Because by the way, no one. Do you know why most people. Oh, this is good. I'm glad we got this. You know why most people listening have not been able to execute on their strategy?

[Amanda]

Why?

[Gary Vee]

Because they're not good. They're not good.

[Amanda]

Always about in here.

[Gary Vee]

Because you don't have enough energy to get through your strategy if you're not good.

[Amanda]

That's right.

[Gary Vee]

You'll die along the road. So I don't know if identities, the way I'm talking about self awareness and self acceptance.

[Amanda]

It is. It is. That's.

[Gary Vee]

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?

[Amanda]

Well, this is it. And the higher you go, the more shit you deal with, I think, oh, my God.

[Gary Vee]

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? 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.

[Amanda]

Fire. Oh, my God. Just putting out fires all day long.

[Gary Vee]

My whole life is shit on, shit on, shit on, shit on, shit on, shit with the occasional smile.

[Amanda]

This is refreshing to hear as an entrepreneur.

[Gary Vee]

Good.

[Amanda]

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?

[Gary Vee]

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.

[Amanda]

So true.

[Gary Vee]

But that smile's worth everything.

[Amanda]

It is.

[Gary Vee]

It is.

[Amanda]

Gary, thank you so much. This moment was worth everything. Thank you so much for being here, everybody.

[Gary Vee]

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. You can't reason with the sun. Trust us, we've tried. This summer, it's time to put that angry ball of fire on mute. Colombia's Columbia's Omnishade technology is engineered to protect you from the sun's harsh rays that can burn and damage your skin. The sun is relentless, but so is our gear. Level up your [e-mail] to spend more time outside and less time slathering on aloe lotion. You're welcome, Columbia Engineered for whatever. Some follow the noise. Bloomberg follows the money. Because behind every headline is a bottom line, whether it's the funds fueling AI or crypto's trillion dollar swings. There's a money side to every story. And when you see the money side, you understand what others miss. Get the money side of the story. Subscribe [e-mail] journey see you later.