Nice Guys Finish First: How to Maximize Joy Over Money

Summary

The GaryVee Audio Experience

Episode: Nice Guys Finish First: How to Maximize Joy Over Money

Date: March 17, 2026
Host: Gary Vaynerchuk
Guest/Interviewer: (Unnamed, possibly a media professional and peer)

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Episode Overview

This episode of The GaryVee Audio Experience explores Gary Vaynerchuk’s core belief that “nice guys finish first,” challenging the common notion that business is inherently cutthroat. Gary discusses his personal journey as an entrepreneur raised in an immigrant family, how he’s balanced ferocious competitiveness with kindness, and why maximizing joy—rather than money or external validation—is his metric for success. The conversation spans reflections on upbringing and resilience, the power of candor and empathy, advice for thriving in changing times, and thoughts on self-esteem, forgiveness, and practical optimism.

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Key Discussion Points & Insights

1. Contradictions: Aggression vs. Kindness in Business

• Competitiveness in Context:
  Gary draws a parallel between sports and business, explaining that while he’s fiercely competitive (“slitting throats”), it’s always fair play and never truly personal.

  “That is within the context of fairly playing in business. That's an important word.” — Gary, 01:58

• Kindness as Strength:
  Gary attributes his kindness to both personal disposition (nature) and his mother’s nurturing, arguing it’s foundational to long-term success and legacy.

  “Nice guys finish first. To your point, like thank you.” — Gary, 03:47

2. How We Keep Score: Rethinking Success

• Materialism and Social Metrics:
  Gary critiques the societal obsession with followers, wealth, and possessions as measurements of achievement.

  “One of the great issues we have in society right now is how we keep score.” — Gary, 03:48

• Process over Fruits:
  He insists he builds businesses for the joy and creativity involved—not as a means to acquire more “stuff.”

3. Upbringing, Resilience, and “Growing Up Early”

• Immigrant Experience:
  Gary reflects on his formative years in a crowded Queens apartment, linking early maturity to adversity and responsibility—not just immigration.

  “I’m fascinated by growing up early and I’m fascinated by growing up late.” — Gary, 04:44

• The Perils of Over-Coddling:
  He observes contemporary “late adulthood,” where young adults are insulated by their parents, contrasting it to the resilience born of adversity.

  “We have grown men and women being treated like children…that’s an issue.” — Gary, 05:26

4. Reflection, Pattern Recognition, and the Role of History

• Historic Lens on Innovation:
  Gary relies on “historical pattern recognition” to forecast trends and remain unfazed by new technologies.

  “I use history as an incredible beacon to understand nothing's different and everything's different.” — Gary, 09:46 & 00:00

• Optimism over Fear:
  He leads with optimism, seeing change (like AI) as a natural progression in human development.

5. Resilience, Self-Esteem, and Parenting

• Gifting Resilience:
  The hosts discuss the difficulty of passing down resilience that was forged in hardship, especially while raising children in more comfortable circumstances.

  “I worry about their resilience because it's a hard thing to pass down.” — Interviewer, 08:24 “You can't fake it. That's right.” — Gary, 08:29

• Self-Esteem at the Core:
  Gary believes that much of success—and willingness to take risks—comes down to self-worth and insecurity.

  “We could talk for the next hour…I promise you. The chess moves, it's all gonna go down to a very binary game. Where do you sit on your self worth?” — Gary, 17:02

6. Fear of Change, Authenticity, and Content Creation

• Just Start, No Perfection Needed:
  Gary advises aspiring creators to ignore perfectionism and external judgment, using authenticity and self-awareness to guide content strategies.

  “Content creation comes in many forms…volume of content is not subjective, but the quality is.” — Gary, 55:59

7. Candor, Empathy, and Leadership Growth

• Candor as Kryptonite:
  Gary admits candor was his leadership blindspot—he long avoided giving difficult feedback out of fear of making people feel bad.

  “Your inability to be canderous, which is wild…my candor's unstoppable…but when I start to have feelings…that started…me not being well at giving you candor.” — Gary, 23:32

• Evolving from Radical Candor to ‘Kind Candor’:
  He now practices and teaches a more compassionate, direct style of feedback, seeing it as both a muscle and an essential leadership tool.

  “I called it 12 and a half [leadership habits] because I said, every leader has haves. And my have is candor.…I’m gonna rebrand it…Kind Candor.” — Gary, 24:54

8. Family Business, Prioritization, and Maximizing Joy

• Navigating Family Dynamics:
  Insights into working with his brother and father, handling equity, and value creation—with candor and compassion.

• Why ‘Joy’ Is the KPI:
  Gary juggles many ventures (restaurants, sports, media, etc.), but prioritizes joy and learning over singular financial maximization.

  “I am trying to maximize joy…If I wanted to maximize money, someone’s argument of like, you should prioritize would hold more weight with me.” — Gary, 37:54–38:04

9. Forgiveness, Accountability, and Letting Go

• Forgiveness as Emotional Unclogging:
  Gary advocates for forgiving others—and oneself—as the key to personal growth and emotional freedom.

  “Forgiveness is the answer to the quiz that many people are struggling with right now.” — Gary, 40:22

• Modern Loneliness & Parenting:
  He challenges the idea that technology causes loneliness, pointing instead to changing parenting styles, self-esteem, and lack of accountability.

  “I believe the self esteem issue is why people are lonely… That is the big conversation.” — Gary, 46:35

10. Practical Optimism and Taking Responsibility

• Practical Optimism Over Doom:
  He criticizes the allure of negativity and calls for optimistic, actionable attitudes—even referencing historical overreactions to new technologies.

  “If you think it’s all ruined and it's all wrapping up…why are you going to your job?” — Gary, 51:14

• Taking Ownership:
  Gary urges adults to stop blaming their parents and take charge of their own growth after a certain age.

  “At what age is it appropriate…to stop blaming your parents for everything in your life and realizing you are now a grown up…and you can do actions to mitigate the pain you’re feeling?” — Gary, 52:29

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Notable Quotes & Memorable Moments

• On Building Without Needing Stuff:

  “I don’t build businesses to buy a third home or a golf course or a private jet.” — Gary, 04:04

• On Candor as a Leadership Lesson:

  “Your inability to be canderous…your kryptonite.” — Gary, 23:32

• On Loneliness and Technology:

  “It’s very easy to not be lonely in today’s world because of technology. And it's very easy to be lonely in today's world because of technology. I don’t think technology is the driver…” — Gary, 45:28

• On Forgiveness:

  “Forgiveness is underrated. I wish more people…would pick up the phone and call their mom…or go to the mirror and say, it's okay.” — Gary, 40:41

• On Maximizing Joy:

  “I am trying to maximize joy.” — Gary, 38:02

• On Passing on Uber:

  “That $50,000 check would have been $540 million. So that one didn’t work out.” — Gary, 54:01

• On Content Creation:

  “Content creation comes in many forms. …be self aware of what medium you like and then understand that volume of content is not subjective, but the quality is.” — Gary, 55:59

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Important Timestamps

• “Nice guys finish first” context: 03:47
• How Gary defines keeping score: 03:48–04:04
• Reflections on growing up as an immigrant: 04:41–06:32
• The pitfalls of over-coddling young adults: 05:26–06:32
• How self-esteem affects all outcomes: 17:02–17:31
• On giving feedback & growing as a leader: 22:44–26:56
• On juggling multiple businesses and prioritization: 36:48–38:04
• The vital role of forgiveness: 40:21–41:55
• How tech influences loneliness: 45:27–47:02
• Advice for a pivot or for new grads: 55:16–55:55
• On content creation strategy: 55:59–56:39
• Emotional story of the hand-knit Jets jersey: 57:14–58:56

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Practical Takeaways & Advice

• Don’t let “contradictions” in personality or ambition limit you; embrace both fierce competitiveness and deep kindness.
• Reflect often and use history as a guide for dealing with change: “Nothing’s different and everything’s different.”
• Prioritize self-awareness and authenticity, especially when producing or sharing work in public—perfection is less important than presence and courage.
• Develop candor as a muscle; “kind candor” can be both supporting and constructive leadership.
• Focus on maximizing joy and learning rather than chasing external validation or pure profit.
• Forgiveness—towards both others and oneself—is pivotal to emotional clarity and growth.
• Take accountability: at a certain age, stop blaming your upbringing and take ownership of your path.
• Embrace change and practical optimism; history shows we always adapt and move forward.

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Final Notes

This episode is an engaging, vulnerable deep dive into the philosophies and experiences that shape Gary Vaynerchuk’s approach to business, relationships, leadership, and life. Practical wisdom is intertwined with stories from his upbringing, mistakes and pivots, and ongoing mission to maximize joy—making it a must-listen (or read) for anyone seeking meaning or motivation beyond the traditional chase for success.

Transcript

[Gary Vaynerchuk]

Social media was very easy for me to understand. It was cable television. It was. The television was shit on when it was invented. The radio is primary. AI is scary. No, it's not. It's the same thing we did with electricity. Like, I use history as an incredible beacon to understand nothing's different and everything's different. But I think people lead with fear and I lead with optimism and history. And I reflect both internally about my journey, but also externally about the human journey. And that becomes the data points that I make decisions on. This is the GaryVee audio experience.

[Interviewer (possibly a female media professional or podcaster)]

I am so excited to have you here. I know that the audience is going to be particularly excited. You and I met when you were at the early days of starting VaynerMedia.

[Gary Vaynerchuk]

Yes.

[Interviewer (possibly a female media professional or podcaster)]

And while I was not a client, and I think this is an important thing, when I called you when New York was having a difficult time and we pulled together to try and help the city and said, gary, we need your help. Will you give us a PR team to help with the moment for Broadway? Without hesitation you said yes. And so, you know, that's a rare thing because it was not a transaction, it was just a relationship. And you didn't have to say yes because it's not like I'd been a paying client of yours for years to come. And I think it's such an interesting story about you because you're a man of contradictions, which, by the way, I would say many of us are. If we were really honest, we would all be much more honest about our contradictions and our messy parts than we tend to present. So I think about. Because, as you know, I mentioned when you first walked in, I did a lot of research. Yes, and you have a lot of lessons that you share. You know, interestingly, when you walked in, you said, it's all about the audience for me. And I always say when somebody asks me to speak, how can I be useful? Because what's the point otherwise? Yes, you talk a lot about, you know, wanting to win and slitting throats, but at the same time, you also talk about kindness and relationships. And you just did a book for kids, 4 year olds. What is that contradiction about for you?

[Gary Vaynerchuk]

I don't see this contradiction because to your point, everything needs context. I view business when I do business, and I was just yapping with your lovely hubby about trading cards. I view it as sports. And I think when we all watch sports, we know that there are players, both in women's and men's sports, that are incredibly fierce when they're on the field, like throw an elbow and you know, a tooth comes out and they spit it. I'm just a very different player when I'm talking about slitting throats or things of that nature. Being hyperbolizing about like being competitive. That is within the context of fairly playing in business. That's an important word.

[Interviewer (possibly a female media professional or podcaster)]

Before I said, well, I wasn't thinking you were gonna come here.

[Gary Vaynerchuk]

Yeah, yeah, of course not. And then again, you know, as a, as a big sports fan, I'm very frustrated when my team loses a game and they went so hard and then the game's over and everyone takes off their helmet in this scenario and they're hugging and how's your wife Karen? And they were just beating the crap out of each other 30 seconds ago. I think that's who I am. I think in business I'm competitive. I'd like to win. I want to build an empire. I have great ambition. I enjoy it. I am probably frustrated. I didn't have the physical talents to be an athlete. I get such joy out of pickup basketball. I just turned 50. I'll play pickup basketball as much as I can. I like competition. A board game sends me into a frenzy. It's in me. But that is wildly overridden by the other fortunate DNA traits I have, which is I'm a nice guy. And not only am I a nice guy, chemically, I got very double fortunate. I have an all time mother that took those ingredients and knew exactly how to cook it predominately. Cause I got so many of them from her. And so yeah, I think nice guys finish first. To your point, like thank you.

[Interviewer (possibly a female media professional or podcaster)]

You actually think that.

[Gary Vaynerchuk]

I know that because I know it because I'm not a child. I also don't score things the same way I think society does. I think one of the great issues we have in society right now is how we keep score. I think we continue, unfortunately to go down the path of materialistic things, followers, bank accounts stuff, how many rooms in a home. And I just don't see life that way. To your point of contradiction. I want to build these things, but I want to build them for the sake of building them, not from the fruits that come out of them. You know, I don't build businesses to buy a third home or a golf course or a private jet.

[Interviewer (possibly a female media professional or podcaster)]

But you were a kid, so like me, you were an immigrant.

[Gary Vaynerchuk]

Yes.

[Interviewer (possibly a female media professional or podcaster)]

And you were a kid who came here not speaking English, living in a house in a small apartment with lots of people. Not easy.

[Gary Vaynerchuk]

Studio in Queens. Eight, like real tight, right.

[Interviewer (possibly a female media professional or podcaster)]

Okay. So you definitely had to figure out how to be nice to get along.

[Gary Vaynerchuk]

Well, it's really funny. Like, you know, my great grandmother and my grandmother, they were sharp cookies. You know, niceness was an incredibly unique energy that my mom was bringing to my surroundings and my great grandfather on my dad's side. But you know, I was very young, I was four, five, six in those environments. Those environments didn't necessarily form my niceness. Those environments. I think it's really interesting. I think one thing I'm spending a lot of time on. I know I'm ranting here, but it's where I'm going with this conversation. I'm fascinated by growing up early and I'm fascinated by growing up late.

[Interviewer (possibly a female media professional or podcaster)]

What does that mean?

[Gary Vaynerchuk]

I think we have a growing up late issue in society right now. I think too many parents are treating their 27 year olds like they're 2.7 years old. We have a real angst in society right now. We have grown men and women being treated like children by their parents in a way that we've never had historically. And that's predominantly because we're a mature empire in the West.

[Interviewer (possibly a female media professional or podcaster)]

It's kind of a privilege.

[Gary Vaynerchuk]

It's a massive privilege. But it's, you know, even wealthy families of the 70s and 80s did not have this kind of like minutiae payroll that we now have. Like again, at scale, you have 25 year olds running around this city who have their parents subsidizing much of their life and have an app on their phone to track them. We have a late adulthood thing going on. That's an issue. And I'm fascinated by early adulthood. You know, I was raised by parents who lost a parent very young. So my mom lost her mom at 5 and my dad lost his dad at 15. They became grown and they lived in the USSR and they immigrated to America at 20. They were grown early. I was grown early.

[Interviewer (possibly a female media professional or podcaster)]

I was grown early.

[Gary Vaynerchuk]

I get it. People with immigrant stuff. I actually think it's a grown early thing. Cause there's a lot of people that are not born in another country that grow up with very little and have different outcomes. I think it's a grown early thing. And a lot of immigrants grow up with nothing and do not have success. And I think it's a grown early thing. It's an over coddling thing. It's an adversity. But you know, the kindness wasn't formed in those early Queen's days. The kindness were formed from the womb. My cocoon of my life was my mother and My mother is pure kindness, but accountability, I got that from her purely. 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. They'll make my mom super happy.

[Interviewer (possibly a female media professional or podcaster)]

So, you know, it's interesting. It's interesting. So you're recently 50?

[Gary Vaynerchuk]

Yes.

[Interviewer (possibly a female media professional or podcaster)]

I think, you know, with age comes this look back. Right. I mean, for so much of my career when I was CMO and trying to survive these crazy sample jobs one after the other.

[Gary Vaynerchuk]

Yes.

[Interviewer (possibly a female media professional or podcaster)]

Which I know, you know, is not easy.

[Gary Vaynerchuk]

No.

[Interviewer (possibly a female media professional or podcaster)]

You know, you're just in the hustle.

[Gary Vaynerchuk]

Yes.

[Interviewer (possibly a female media professional or podcaster)]

But there are moments where you reflect and you look back. And I had some of those opportunities more recently, one when I had to give a TED Talk. You know, things where you have to reflect back to. To your point to try and be useful to the people who may take the time to listen when you do that. Which it sounds like you're doing more of now.

[Gary Vaynerchuk]

No.

[Interviewer (possibly a female media professional or podcaster)]

Well, you're a parent. Hold on.

[Gary Vaynerchuk]

Sure. But go ahead. Go ahead.

[Interviewer (possibly a female media professional or podcaster)]

I'm gonna go somewhere else.

[Gary Vaynerchuk]

Go ahead.

[Interviewer (possibly a female media professional or podcaster)]

You're a parent. And, you know, one of the things I think about, Right. As somebody who became a parent is, yeah, I grew up fast, and that definitely was part of how I learned to be resilient. I didn't want my kids to have some, you know, I didn't want my kid to have to survive revolution, you know, lose their father, blah, blah, blah, in order to be resilient.

[Gary Vaynerchuk]

Of course.

[Interviewer (possibly a female media professional or podcaster)]

And I worry about their resilience because it's a hard thing to pass down. Right. Because it was a circumstance.

[Gary Vaynerchuk]

You can't fake it. That's right.

[Interviewer (possibly a female media professional or podcaster)]

Right. So do you worry about that for your own kids?

[Gary Vaynerchuk]

A couple things. My no was not that I'm not reflective. My no was I've been reflective my whole life.

[Interviewer (possibly a female media professional or podcaster)]

Ah, interesting.

[Gary Vaynerchuk]

It was a different no.

[Interviewer (possibly a female media professional or podcaster)]

Oh, that's much better. Because I definitely was not reflective my whole life.

[Gary Vaynerchuk]

It's funny, I think a lot back to my great grandfather being a big factor in my life for that one year when we first immigrated, unfortunately, passed away right after. But I spent almost all my time with either my mother, but my mother was just about to have another baby, and we had my sister pretty early, which was having another child when we first got here was definitely not probably the most strategic. But we're so glad we did because my sister's such a core part of my life. But I spent a ton of time with my Great grandfather and he spent all his time with other 80 year old immigrants from the old country. And I don't know if it's DNA, I don't know if it's nature, nurture, but I've been 80 my whole life. I've been reflective. I was a terrible student, but I was great at history. Cause I was. I would argue that all of the accolades I get as a businessman about seeing around corners, early investor and all these things has a lot to do with historical pattern recognition. I lack fear.

[Interviewer (possibly a female media professional or podcaster)]

What does that mean, historical pattern recognition?

[Gary Vaynerchuk]

Social media was very easy for me to understand. It was cable television. The television was shit on when it was invented. The radio is primary. AI is scary. No, it's not. It's the same thing we did with electricity. Like I use history as an incredible beacon to understand nothing's different and everything's different. But I think people lead with fear and I lead with optimism and history. And I reflect both internally about my journey, but also externally about the human journey. And that becomes the data points that I make decisions on.

[Interviewer (possibly a female media professional or podcaster)]

There's so many things to unpack in that conversation. Just in that one statement. It's interesting because we have parallels and then yet we're obviously different. Of course, you know, I also, like, you didn't have that sort of fear partly, I think, because when you have to survive, you don't have the luxury of fear to be put on.

[Gary Vaynerchuk]

You also are living it. And you know what the downside is? You know, when you're born into something that's remarkable, you're confused of what bad is, you know, I don't fear to go to zero because I grew up in an environment where we didn't have much, but we had love. And like. So I knew that money wasn't gonna be the. Like. I was taught very early that money's not taught by words, by actions. I had a unbelievable childhood. We had little. My mom was also cheap on top of everything else. So even as we were starting to make it and become middle class, it felt like what I was like back to reflection at like 35. I called my sister one day. I'm like, wait a minute. We were a little bit better than we thought. It just that mom didn't buy us anything, you know, it was just that kind of life. Nonetheless, of course, my friend, we know, we know it's not that scary. Like in the great words of the song, like, all you need is love is kind of very uncomfortably real. I surely don't need stuff I do not need outside Validation.

[Interviewer (possibly a female media professional or podcaster)]

Is that really true?

[Gary Vaynerchuk]

It is really true. And you know what's fun? It's fun for me because I get this sometimes I'll get like a fourth grade classmate who will listen to this, who I haven't talked to literally sometimes in 30, 40 years. And all of them, all of the people that knew me before you all knew me, love this moment because they know, and I definitely know, as you asked, that I know that people don't believe me. I know that people believe that the things that come out of my mouth today is because they think I got here and now it's easy for me to choose love or be chill or this. I know I got here because I believe that stuff.

[Interviewer (possibly a female media professional or podcaster)]

No, I watched an interview of you yesterday. It wasn't really an interview. You were on stage talking about your new children's book, and I was really fascinated by the fact that you thought you wanted to talk to four year olds.

[Gary Vaynerchuk]

Yes, we'll get to that.

[Interviewer (possibly a female media professional or podcaster)]

Okay, There's Crush it and then there's like teaching children empathy.

[Gary Vaynerchuk]

Yes.

[Interviewer (possibly a female media professional or podcaster)]

And at the end of that, they opened up the mic and people came up and asked questions. And there were people who knew you from many, from your wine business to different things. But one woman did what often happens, which is she stood up and sort of gave a little soliloquy about her background and then was like, I really want a job. And your graciousness and accepting her resume in front of a whole audience was actually very remarkable. So, I mean, I don't think you can manufacture that. Right. So I understand that. But at the same time, you know, one of the things that happens when you, like, get the things you might not have had. And let's put love aside, because I also feel like I was fortunate and that I had a very loving childhood. There was sort of a sense that you could do anything Right. In my home, despite all the other things, you do still age. And I think a lot of people with age and human nature, they're not. We don't like change humans. Right. And you actually thrive in change.

[Gary Vaynerchuk]

I love change. God, I love it. I'm practical. How can you not like change? It's the most true thing that will happen.

[Interviewer (possibly a female media professional or podcaster)]

It's the only constant.

[Gary Vaynerchuk]

It's the only. I just, you know, again, I'm aware that I'm a funny character. Like, because I've done so much content for so long and because a lot of it will skew motivational or there's people that walk into VaynerMedia who've known me for A decade. And they're like, what is this? I'm like, this is VaynerMedia. They're like, you have a company. I'm like, I have 2,700 employees. You know, like, I actually associate with the COO. If we're talking corporate, I actually associate internally with the COO part of myself, maybe more than anything.

[Interviewer (possibly a female media professional or podcaster)]

What does that mean?

[Gary Vaynerchuk]

I'm an operator.

[Interviewer (possibly a female media professional or podcaster)]

What does associating with the COO mean?

[Gary Vaynerchuk]

I feel like if you ask me, what are you? I would say, I'm an operator. I'm aware that I'm a marketer. I'm aware that I'm a salesman. I'm aware that I'm a personality. I'm aware that I'm a lot of things. A guidance counselor and coach and therapist. But in my soul, I like being practical and operating. That's the steak. Everything else is the side dish, the sizzle, the amuse bouche, and the dessert. And I think it speaks to change. I just don't even have the audacity to not like change. It's the least practical energy.

[Interviewer (possibly a female media professional or podcaster)]

But both you and I know, while both you and I are not, you know, we love risk, and we're a little bit fearless, you know, we can agree with sometimes that's good and sometimes that's not so good. But the thing is, most people are not like that. Right? Most people are not built that way. That's human nature.

[Gary Vaynerchuk]

Yes. Most people really struggle with the outside noise. Right.

[Interviewer (possibly a female media professional or podcaster)]

So today, in a world where AI is coming in and people are so. I mean, I spoke to somebody yesterday who was in the retail business, and she was telling me how many senior people in her business are now out of a job because of all the shifts that are happening.

[Gary Vaynerchuk]

For now.

[Interviewer (possibly a female media professional or podcaster)]

For now. But there's a real thing, right? And so there's a real fear as what's going on in the market, knowing that not everybody's built the way we are or the way you are. What advice do you have on a practical level? Because you are an operator, what advice

[Gary Vaynerchuk]

do you have for somebody that you're in control of your life? You're not in control if someone fires you because they've decided they have the power to do that, and they've decided AI can do your job. You are not in control of that. You are in control of knowing that looms in the air. And you can start making content on LinkedIn tomorrow to build a bigger profile, to create other opportunities for yourself.

[Interviewer (possibly a female media professional or podcaster)]

You could, but you know, how many people. It's so funny, because I watch so much of your content. And what struck me is, you know, you do content just anywhere. It doesn't always have to be perfect. You said here an ambulance.

[Gary Vaynerchuk]

Come on. Exactly.

[Interviewer (possibly a female media professional or podcaster)]

Meanwhile, I had a girlfriend visiting and she was saying to me that sometimes my hair is not perfect on the podcast or I don't, you know, I should really glam it up. And I thought to myself, some people are just left in the old world of media.

[Gary Vaynerchuk]

Yeah.

[Interviewer (possibly a female media professional or podcaster)]

But the new world of media, which is not, you know, CBS Evening News.

[Gary Vaynerchuk]

That's right.

[Interviewer (possibly a female media professional or podcaster)]

Is very different. And in fact, if you go on the TikTok a lot of it, it does better if it's messy.

[Gary Vaynerchuk]

I think we're in an incredible era of and you know, I think high production value, high fidelity. You know, my wife Mona, like, aesthetics matter so much. She struggles to consume anything in any form. A room, a magazine, a post. She needs the aesthetics. I need the authenticity. I don't think a dog barking or an ambulance, I think that's charm. I think that's even more real. And everyone's allowed to consume what they want. I definitely think we're in an and era.

[Interviewer (possibly a female media professional or podcaster)]

But the thing is, many people, because of that fear of it needing to be perfect, don't start at all.

[Gary Vaynerchuk]

Yes. I mean, you've been doing a lot of research, which I'm very humbled by, by the way, because we know each other. You know, I think about self esteem and insecurity 24 7. I think that's the. I don't think there's anything else like what we're talking about here. We could talk for the next hour, I promise you. The Plinko board, the chess moves, it's all gonna go down to a very binary game. Where do you sit on your self worth? Where's your self esteem? Where's your insecurity? And I can tell you everything that's about to happen after that.

[Interviewer (possibly a female media professional or podcaster)]

I feel like I should just lie down.

[Gary Vaynerchuk]

You know what I mean? I mean, for everyone who's listening, like, of course you're gonna struggle making content if you're worried about what people are gonna think about the way you look, how good your writing is. I mean, there's people who take nine takes cause they tripped up on a word that was like a little flubby. I mean, I could say something that makes no sense for four minutes and keep going and be like, that's what it is.

[Interviewer (possibly a female media professional or podcaster)]

Okay, so I wanna go back to trying to be useful, please. Which I know is the thing that drives both of us crazy. Yes, I Wonder why that is.

[Gary Vaynerchuk]

Did you ever. You should ask again. Did you ever not have self esteem or is just something you always.

[Interviewer (possibly a female media professional or podcaster)]

Okay, well first of all I want to dig into the self esteem question because I'm sure to know if you think you have self esteem or if you always had it. But hold that thought.

[Gary Vaynerchuk]

Okay.

[Interviewer (possibly a female media professional or podcaster)]

I want to go back to the advice. Right. So you were saying. Because I. I wanted to just be clear that content doesn't need to be perfect. You were saying you have control, get on LinkedIn and do what you know, have a voice.

[Gary Vaynerchuk]

If you're a retailer, like we were just talking about, like talk about your perspective on what you're seeing in the retail environment. What you think about live shopping or not, what you think about AEO and GEO and LLMs, what you think about end caps or what's going on with mixed retail or pop up shops. I can't speak to an executive's knowledge base or their thoughts, but I can speak to. If you don't have thoughts on that and you don't have opinions on that and you don't have expertise on that, maybe you were overpaid.

[Interviewer (possibly a female media professional or podcaster)]

But also you need to be present, you need to be out there.

[Gary Vaynerchuk]

Correct. Like you talking about 14 years ago, we did it like this. That's nice. By the way, I just talked about. I love a good look back for context, for information, but not for the actual blueprint. Because the field changes, the field of play changes.

[Interviewer (possibly a female media professional or podcaster)]

So let me pull back the thread. There's so many threads in the conversation between you and me, which is what I predicted.

[Gary Vaynerchuk]

Did you always have confidence in many arenas? I will tell you one of the silly regrets of my life. It's not a real one, but like I did not have confidence with girls in high school and college to the level that I could or should have. Meaning I wasn't bad at it. I wasn't a complete zero. But it was the one place where I did value the feedback. Meaning if I asked a girl out and she said no, that seemed hard and that led me to not doing it. Which is why I know what it feels like. I understand in that arena I didn't do things that I wanted to do. Oh, she's cute, I'd like to date that girl. I wouldn't do it cause I feared the noise in that arena. I struggled with that in pretty much every other arena I did not. Especially from an adolescent standpoint. It was insane to me. It continues to be insane to me how starting at 11 years old, even though every teacher and don't forget 80s, 90s, middle, lower class New Jersey. These teachers gave it to you straight. My teacher starting in fourth grade told me I was going to be a loser. I was gonna be a garbage man. I was never gonna amount to nothing to my face.

[Interviewer (possibly a female media professional or podcaster)]

Is that straight or just really depressing?

[Gary Vaynerchuk]

I think again, by today's standards, seems inappropriate. A lot of us in this room right now grew up in an era where that was just kinda normal. It wasn't like super inappropriate. That's what authorities did. Like not only them, my friends, parents, you know, as we started getting into high school years, hung out with kids that got as and had ambitions. And I could feel some of their parents being like, you need to cut that one. Cause he gets these dnf. And you know what's funny? I was such a good kid. I never drank, I never did drugs. I'm such a nice boy. So it wasn't awful. Cause I was a good influence everywhere. Other than getting D's and F's, I never wavered, I never struggled. I sold baseball cards in the malls of New Jersey when I was 12 years old. All grownups and me. And I'm making as much, if not more money. So I was getting wild validation from the business world, you know, I was getting wild validation from a social standpoint. Like I was beloved both by boys and girls, which even made the not asking out girls even more, you know, interesting. It's interesting that that was there. So everywhere I was getting validation other than grades. And so yeah, I just, I was never scared of a. No in any environment. Sports. I loved losing. Like I loved losing. I didn't want to lose. In fact, Until I was 10, I probably cried every time I lost them. Anything, anything. Tennis, pool, a race. I mean, I cried. I don't know if a human could cry more between 5 and 10 than I did. I probably cried every day.

[Interviewer (possibly a female media professional or podcaster)]

Do you cry now?

[Gary Vaynerchuk]

I am very easily triggered into crying. I just watched Song Song Blue. Like I barely held on in a couple of spots. Not to ruin the movie for people, so I won't go there. But it's like I'm back to dating. I cried on a very big date my senior of high school at Lion King. When the dad dies, I cried full pledge. That did not go over well in 1994.

[Interviewer (possibly a female media professional or podcaster)]

Did that end the date?

[Gary Vaynerchuk]

That ended the upside of the date for sure. And so yeah, I'm very emotionally charged. I have incredible extreme empathy, compassion and sympathy, which makes me a remarkable marketer and salesman. And luckily I was so well Parented. I tend not to do anything with that special skill that tends to be detrimental to the other side.

[Interviewer (possibly a female media professional or podcaster)]

It's interesting you say that about empathy because I read that your empathy also made you not such a great manager because you didn't like giving feedback.

[Gary Vaynerchuk]

I don't know if that was empathy, you know, and I might have said it that way at the time, to your point, as we all keep evolving. Yeah, it's crazy. Like, you know, people ask me a lot in interviews, what would you tell 25 year old you or 18 year old you? And I always, because it's the truth. I always go to. I would have sat that kid down and said kid. Cause this is how I felt at 18. You're right, you are a superhero. It is going to happen. But you've got kryptonite. And let me tell you what it is. Your inability to be canderous, which is wild. Cause as you know, Gary Vee, especially in the ad land, I came out guns a blazing with my candor. Is my.

[Interviewer (possibly a female media professional or podcaster)]

Have you watched your keynote that led to the. The book?

[Gary Vaynerchuk]

Love that. That's a wild one. You know, so like, you know, my candor, even in this interview, my candor's unstoppable. I'm talking to the world. But when I start to have feelings of anything that looks like liking you, let alone loving you, which can happen immediately, by the way, within the first five minutes of meeting someone, that started for a long time in my life, the predominant years of my life, the clock on me not being as well at giving you candor. You know, I've been a boss since I was 17 years old. Since I was 17, I was managing everyone in my dad's liquor store. So I was a child. You know, my mom is also not overly canderous and my father was inappropriately canderous to his employees in a Soviet like style. So I grew up being shocked by how negative my father would talk to his employees, which kind of like made me want to overcorrect and be the other way. I was right. Raised by someone that if it isn't obvious to everyone, here is my North Star, who I put on a pedestal, who also struggled with candor. She like me, I picked this up for her, wanted to figure out how to fix it without the candor, would put in triple effort to do it. And I basically managed employees my whole life to the tunes of tens of thousands at this point where I'd rather figure out how to put you in a position to succeed on the shortcoming that I'm saying, then help you. Now I understand it to be help. At the time, I thought I would say, hey, you're struggling with this. And I would think you're thinking you're gonna get fired and that you have. I hated the thought that I was gonna deposit something you were gonna have to sleep with tonight. Cause I hate fear. I fucking hate fear. I hate that the world weaponizes it. My relationship with fear is not only do I not fear you, fear I. I'm gonna fucking kill you fear. So I viewed as me giving what I now understand. It's feedback that is well intended. I viewed it in my teens, through my 20s, through my 30s, into my 40s. I viewed that as I was contributing to fear. I was unable to see it. It was a blind spot. It was my kryptonite. I did not understand. And once I wrote a book about was about 13 habits of leadership. And I called it 12 and a half because I said, every leader has haves. And my have is candor. And I'm gonna rebrand it in this book and called it Kind Candor. And I've rolled that out to all my organizations. Cause I think radical candor. I've also watched. I've watched manager after manager use candor as an excuse for manipulation, for holding down a young talent. Look at all the head nodding going on. We're grown now. We know. And so I was like, damn, I don't like this candor. People are using this as a weapon for the wrong. And so I didn't have a good relationship with it.

[Interviewer (possibly a female media professional or podcaster)]

So it's funny, you know, having worked in a lot of different companies, when I got to tech, radical candor, as you know, was a thing.

[Gary Vaynerchuk]

I remember. I remember. Yeah. Yeah, it was hot. It was hot. Yep.

[Interviewer (possibly a female media professional or podcaster)]

And I, like, you didn't like making people uncomfortable. I wasn't afraid to do it, but I didn't like it.

[Gary Vaynerchuk]

Yes.

[Interviewer (possibly a female media professional or podcaster)]

And sort of get off on that. Which, you know, we work for plenty

[Gary Vaynerchuk]

of people who did.

[Interviewer (possibly a female media professional or podcaster)]

But I did, like, learn later like that. It was really helpful to give people feedback early. But how you give that feedback is everything.

[Gary Vaynerchuk]

I agree.

[Interviewer (possibly a female media professional or podcaster)]

It's everything. And you can say that to people in a way to cut them down, or you can actually do it in a way that's supportive. I mean, there's many ways of doing it.

[Gary Vaynerchuk]

After 45 years of being atrocious at it, not having a good relationship with it, not understanding it, not seeing it, these last five years where I've implemented it day by day, get better, you know, Making it simple on a chart of 1 to 10. I live with gratitude, knowing that so many of the things that matter I was given, the DNA and the circumstances and the mother. That made me an 8, 9, 10 out of 10 on so many important things. But candor was 2, 1, 0. And now knowing that I'm in the 5, 6, 7 range territory, it's changed our company, it's changed my personal relationships, it's changed my life, and I strive to get better. It is super hard. It's no different than the gym I've been on. It's a muscle. It's a muscle. You get more used to it. It actually between how I changed my health and wellness 12 years ago, at 38, I still every morning, do not want to go, do not like it. And on Candor, it enables me to know that people can build, they can change course. And that's why I talk a lot about a lot of stuff, because I know humans can do it.

[Interviewer (possibly a female media professional or podcaster)]

Do you think that working with your brother was easier because you could actually just be, like, have shorthand and not worry about offending him? Like, you didn't have to have radical or different kinds of Candor because you were in business with him for a long time. I mean, you are in other ways now.

[Gary Vaynerchuk]

But I think that. I think there's a lot there. I think my brother was such a breath of fresh air because with my father, who I. So my brother and I started VaynerMedia in 2009. I'm 34. I just spent 12 years working 100 hours plus a week in a box, a store with my father. And, you know, I'm the son, he's the father. You know, he started the company, but I'm the driver of the business.

[Interviewer (possibly a female media professional or podcaster)]

You have no equity.

[Gary Vaynerchuk]

I have no equity. I'm starting to build resentment. I took the business from 3 to 65 million.

[Interviewer (possibly a female media professional or podcaster)]

Did you get a bonus?

[Gary Vaynerchuk]

You're poking. Listen. No, no, no. And you know what's so funny? I very much understand my father. I had to say, we barely got that. It was really intense. It was real immigrant shit. You know, I've come to looking back, I'm like, I really understand my father. Like, he still, if he walked in right now, he's like, but he's gonna get the business when I'm gone. I'm like, dad, I'm gonna be 73. God willing. So. My brother, on the other hand, was 11 years younger. I was his hero. I was as much, if not more of a father figure to him than even my own father was to him. I had already accomplished a lot. So I came into that partnership with a lot of emotional and experiential and results equity with my brother and, and my brother to his credit. We started the company 5050 equity wise. We didn't know, we didn't know how it would play out. But we looked at each other and we promised each other. We don't know how it's going to play out but we will adjust our entire careers to how it plays out. And to his credit, the way it played out was. I was, and he will say it, much more significant impact than what the business became. And when we started Vayner Sports, even though he was running it full time time, the equity was different in my favor. Even though he was running it and everything we've done subsequently, we, we haven't.

[Interviewer (possibly a female media professional or podcaster)]

We all know families aren't easy particularly. I mean I work with my husband. So I say this to you as somebody who has familiarity.

[Gary Vaynerchuk]

Yeah.

[Interviewer (possibly a female media professional or podcaster)]

And I, and I really enjoy it and I'm grateful for it. But it's not easy.

[Gary Vaynerchuk]

No, it's not easy because you're blurring lines.

[Interviewer (possibly a female media professional or podcaster)]

So easy.

[Gary Vaynerchuk]

All of a sudden it's it. My brother and I have had it easy. I'm being very, you know, my father and I had it incredibly challenging yet wildly easy in the macro. It is. I mean I wish it on everyone. And we really had a lot of arguments and had a lot of tension and had a lot of moments. But my gosh. And I'm sure not lost on anyone in this room or anyone listening. As you get older, the time you spend with your family increases in value and all the other things you worried about. Decrease in value. And I cry. Back to crying. I'm getting a little emotional now. I had a very interesting moment. I think it was my junior year of college. I called my mom one day out of the blue and completely broke down and said mom. Cause basically since I was 15, I'm like, I'm coming into the family business. I'm gonna build a monster. And I wanted to build it for my parents. I wanted to. I was so grateful for them. I had that nobleness superhero syndrome. And I knew I would have more time.

[Interviewer (possibly a female media professional or podcaster)]

I knew who I was doing the friends. Cause you really always did want to be a superhero.

[Gary Vaynerchuk]

100%. 100%. And I was raised to be a superhero. I don't know if I always wanted to be a superhero. My mom made me a superhero. You know. Again, my mom was very affected by her upbringing. You know, at the time I was 7 or 8, 9, 13 years old. My mom was an immigrant mom who lost her mom early and my dad lost his dad early. And she would say things to me of like, to my face, you know, this is my hero. If anything ever happens to us, you have to take care of your brother and sister.

[Interviewer (possibly a female media professional or podcaster)]

I will say though, as a kid again, right. I have a younger sister, seven years. And there was always that sense, because you're the eldest.

[Gary Vaynerchuk]

That's right.

[Interviewer (possibly a female media professional or podcaster)]

Of like, if something happens, it's on you. So I mean, there was the sense of incredible responsibility of an older child is a thing.

[Gary Vaynerchuk]

It's a thing. And I just brought it up earlier because it's the thing I'm most working on in my lab right now. In my head, this early adulthood, late adulthood. You and I had that. And I'm gonna say it again. I'm poking at this zit for everyone who's listening. Cause I know what's going on with a lot of parents that have 25 year olds. There's a lot going on right now. I get all the DMs from both of them. You and I have that. And we have 29 year olds where mommy and daddy are picking up the phone 13 times and taking care of everything. Financially and emotionally. We have a problem. And a lot of what the world's upset about that's going on has to do with that. Not social media, not other things. The just sheer lack of adultness and lack of self esteem that we have in the younger generation. At scale, many are not. I'm not generalizing, but shocking amounts do. So anyway, that's kind of where I was at.

[Interviewer (possibly a female media professional or podcaster)]

Sorry.

[Gary Vaynerchuk]

Yeah, I call my. Oh, I'm sorry. Yeah, I know. Thank you. I never, I never do. And I'm just bawling to my mom and I said, mom, I don't know if I want to go into the store. I don't know if I want to join the liquor store after college. I feel like this was a moment of potential insecurity. I'm like, I think I'm going to be one of the great businessmen of all time. I've got all this stuff. But if I, you know, Dad's tough, like, you know, and he's the best. I mean, I want to make sure I'm painting a very clear picture. My dad in his, you know, my dad's a cat.

[Interviewer (possibly a female media professional or podcaster)]

You can love him and he can still be tough.

[Gary Vaynerchuk]

I'll tell you exactly who my dad is. He's a cactus. He's super, you know, Tough on the outside, but inside it's mushy, which is why he has the cactus. I know it all. A lot of it, anyway. Nonetheless, I really broke the. I didn't want to do it. If I go, I'll never get credit for who I am. Everyone's gonna be like your dad, you know, all this stuff. And it was just one day. It was a 20 minute conversation. I moved on literally the next day. I'm sure my mom. I don't even recall what my mom said. I just remember how I felt. I'm sure it was lots of encouragement and, you know, that's kind of how my game played out. But my dad and I. 80% of the time, it was wonderful. 20% of the time, there was real contention.

[Interviewer (possibly a female media professional or podcaster)]

Hard to leave. No.

[Gary Vaynerchuk]

No. Because my dad wanted it, too. Let's talk about the other side of the story. My father comes to this country with 100 bucks. He works his face off every minute to have his own liquor store business. He's an old school man. He is the man. Here comes his son. Son starts to work around the store. First he's just happy that the son's not a schlemiel and can contribute. Then all of a sudden, he looks around, and five seconds later, his son's 23 years old. And everybody that he's had a business relationship for 20 years has no interest in talking to him. And they only want to talk to his son. And his son's the boss, not him.

[Interviewer (possibly a female media professional or podcaster)]

Yeah, not so fun.

[Gary Vaynerchuk]

So I'm incredibly compassionate to, like how that must have felt. So now. And don't forget, now, I built a monster for him. So now we're one of the most powerful stores in the country. Wineries from France are coming in to kiss the ring and do a deal. And, like, we're as hot as hot gets. We're the kith of, like, wine retail, to put it in streetwear terms. And now I'm willing to walk away and he gets all that power. He was hyped. He was also.

[Interviewer (possibly a female media professional or podcaster)]

So you had no, like, sense of guilt?

[Gary Vaynerchuk]

I definitely had no sense of. Are you kidding? Do you know what I just did? I just got paid $50,000 a year for 12 years to build a $65 million business for my dad. And I'm giving him all the. Which is the only thing he actually wants right now. I felt like a hero, and my dad was naive. You know, I always liked to razz him.

[Interviewer (possibly a female media professional or podcaster)]

He can do it without you.

[Gary Vaynerchuk]

That part. My dad rewrote history. And I get it. Out of pride. In fact, the greatest thing that happened to me was the decline of the business. The next 10 years finally allowed me to get what I was looking for, which is my dad giving me a hat tip that I. I like that for you. You know, that was. Oh, that was. I mean when my dad asked me

[Interviewer (possibly a female media professional or podcaster)]

to help that hatch have been so difficult.

[Gary Vaynerchuk]

I still can't believe it happened that. You know, I can believe it happened because I know where the business was going and it was starting to get a little weird. Died on the ship. You know, my dad is a die on the ship. You know, the good news is the truth is actually I believe if my father and I did not have a good relationship, he would have died on the trip. The good news is we have a great relationship and we're really close and I love him the most and so I don't think it was that hard for him.

[Interviewer (possibly a female media professional or podcaster)]

Okay, so let me pivot to your brother leaves. And you know, one of the things I realized is you're in a lot of different businesses.

[Gary Vaynerchuk]

Yes, I am.

[Interviewer (possibly a female media professional or podcaster)]

Pickleball Vee friend.

[Gary Vaynerchuk]

Yes.

[Interviewer (possibly a female media professional or podcaster)]

Right. A lot of things. And as somebody who also has a lot of interests, I worry sometimes about prioritization. Like how can you put right when you are focused single mindedly on that wine business. Right. Versus having like to share your interest across. I joke. Now I have six jobs. It's very hard to be good at six jobs. How do you think about that?

[Gary Vaynerchuk]

Easily.

[Interviewer (possibly a female media professional or podcaster)]

That is such a lie.

[Gary Vaynerchuk]

It's really not. In fact, I had a meeting yesterday with my comms team. There's some business magazines that want me on the COVID which is humbling. And they asked me what I want on that cover and I said I want it to be a picture of me juggling nine balls with three of them falling. And I wanted to say the juggler. The untold story of Gary Vaynerchuk's business life. Because to your point, even people that know me well have no idea that I have a flourishing TV and production company in Vayner Watt. I have a restaurant group in New York City, in Vegas and now New Jersey that's crushing. Called a private club. A private club called VCR and fly fish Club. Downstairs I have seven to ten alternative sports investments. Pickleball, wiffle ball, unrivaled, the women's basketball league, Many, many, the sailing league. I'm really deep in alternative sports. I have a 2,500 person vaynermedia that people know. Vee friends. People are starting to get known more and more. I Still quietly run the wine business through my best friend. And we do winetext. I have a lot going on. Let me tell you why. The answer is easily.

[Interviewer (possibly a female media professional or podcaster)]

Okay.

[Gary Vaynerchuk]

I ask you in return, what's your KPI? What's your roi? What are you trying to achieve? I am trying to maximize joy.

[Interviewer (possibly a female media professional or podcaster)]

Okay, say more, because I want to hear about that.

[Gary Vaynerchuk]

If I wanted to maximize money, someone's argument of like, you should prioritize would hold more weight with me. Do I believe that if I spent every minute on Vayner X or VaynerSports or VFriends or VCR, that that thing could go. And one could argue definitely Vayner X VaynerMedia, that if I put 100% into that, would I financially do better than spreading it out? The answer is there is a path for me to believe that that is just not what I'm trying to achieve. I want to wake up tomorrow morning and be excited. And what excites me is doing a lot of things. I like potpourri. I want many things. I do not want one thing because I want to enjoy myself. And when I go deep into something, and I do, I can go three months where Vayner eats up every minute. The fact that I can step outside for a second after that and go play here or go play there, that is my joy. That's what I want to do. So I don't struggle with prioritizing.

[Interviewer (possibly a female media professional or podcaster)]

What do you think drives the curiosity to learn? Because that's really what you're describing.

[Gary Vaynerchuk]

I'm inherently wildly curious. You nailed it. That was a real aha. In the last five years, I'm like, oh, shit. I'm wildly curious. The end. I think what's driving me is I'm very creative, I'm very curious. These are not the obvious things of Gary Vee. I've got all these elements to me. I just. I'm into it. There's a term that you hear oftentimes in sports, other areas, listen to your body, right? In medicine, I'm very good at listening to my soul. I'm very good at listening to my body. This might make sense to you based on the vibe of this combo. Sometimes I'm like, man, I wonder if I'm just going to wake up at 62 and be like, you know what? I'm moving to Peru and I'm gonna live on a mountain with a goat. I will listen to my body to the end, and if that's what I want to do, that's what I want to do.

[Interviewer (possibly a female media professional or podcaster)]

Okay, so for people listening who are like, I don't. I'm not in touch with my body.

[Gary Vaynerchuk]

Yes.

[Interviewer (possibly a female media professional or podcaster)]

What are you saying?

[Gary Vaynerchuk]

Yes.

[Interviewer (possibly a female media professional or podcaster)]

How does one get in touch?

[Gary Vaynerchuk]

I think it's different for everyone. You know, for some people, it's therapy to unblock something. For some people, it's exercise. For some people, it's going on a heavy acid and Shroom's trip. I don't fucking know. Like, you know, for some people, it's forgiving people that they're mad at. That's one. Let me go down this path for a second.

[Interviewer (possibly a female media professional or podcaster)]

Okay.

[Gary Vaynerchuk]

I believe forgiveness is the answer to the quiz that many people are struggling with right now.

[Interviewer (possibly a female media professional or podcaster)]

What does that mean?

[Gary Vaynerchuk]

I believe the dogs can sense I'm going somewhere big. I think they can feel it. That's fine. But I think it was more that they, you know, they have a different sense. I think they know where I'm going.

[Interviewer (possibly a female media professional or podcaster)]

The dogs are like, what's happening?

[Gary Vaynerchuk]

Here it is. I'm giving the big answer. I believe many people are fully clogged emotionally, are unable to be self aware, in tune, connected, because they are holding enormous resentment and anger. Please.

[Interviewer (possibly a female media professional or podcaster)]

Sorry, Please. Is forgiveness let it be or let it go? Or is forgiveness a combination of candor, like actually saying your piece?

[Gary Vaynerchuk]

Yeah, I think both. I think. I think forgiveness, in the way that I'm describing it now is to actually call someone that you've not talked to and tell them that you forgive them. Or even more powerful, forgiving yourself for something that you know you did that was completely inappropriate, illegal, whatever it might be, because you're in a different place now. I think forgiveness is a wildly underutilized, not talked enough about. About action and trait that I wish more people. What I'm doing right this second is desperately trying to get through to one person listening to this podcast to pick up the phone and call their mom that they haven't Talked to in 20 years, or go to the mirror and say, it's okay. You were 19. You were a different person then. I just think forgiveness is underrated.

[Interviewer (possibly a female media professional or podcaster)]

So one of the things that's interesting is I listen to you, right? I always learn as I interview people, which is part of the reason I think I like doing it. You know, we started this thing called the Longest Table, where we put the table down the block and invite neighbors to potluck. And now over 2,000 people come. And oftentimes when I'm in industry with people we know, everyone's like, why are you not growing it? Where's the hockey stick? What's happening? It's literally the immediate reaction. And when I say, well, that's kind of not the goal. The goal was to try and just connect neighbors to each other. I mean, of course I'd like there to be people so that I'm not, you know, that we're not three volunteers trying to band aid it together. But the goal wasn't money.

[Gary Vaynerchuk]

Right.

[Interviewer (possibly a female media professional or podcaster)]

And it's very confusing to people, not to me.

[Gary Vaynerchuk]

I would even, I mean this. If we just want to go there, I'll go there with you. Like, I'm not even sure any of my business behavior attached to the money. I just don't see it that way. My first chapter of my career was to give back to my parents. And the second chapter of my career is to fulfill my interest in play. And my play is building businesses. Some are to cook and some are to paint and some are to surf. And my play is to build businesses.

[Interviewer (possibly a female media professional or podcaster)]

Did you ever feel so I buy that. But on the flip side, you don't. As a kid who also had financial insecurity growing up, there was a sense of also having to pay my bills.

[Gary Vaynerchuk]

Like I didn't want collection agencies to come bringing up my bills. Makes sense. I had something very good happen which was I never even knew of a concept of not living within your means.

[Interviewer (possibly a female media professional or podcaster)]

Yeah. I never believed in borrowing money or credit card debt, so.

[Gary Vaynerchuk]

Correct. I literally thought as a grown up I would not have a credit card. That's how anti credit card. And I also have another thing that really works in my favor. I don't care if you think my house is shitty. So basically it's like I just didn't think about money that way. I always thought I could make some because I was good at it. Right. Like when you're making 500 bucks in 1987, which is like a drillion dollars when you came from Nothing, literally in 1988, I'm making 300 bucks at a card show. Ten years earlier, my family has 100 bucks to their name. So very quickly my talents in this capitalistic usa usa, I knew that I could. But more importantly, I never was scared of that part. Money didn't drive me because I knew that If I made 50,000 a year that I was going to live a $35,000 a year life. That's that. So what am I scared of?

[Interviewer (possibly a female media professional or podcaster)]

Okay, so here are some of the predictions I read. Okay. Death of the smartphone interest media versus followers, Social shopping brands starting their own AI influencers. So basically owning IP and AI optimization versus SEO. Those are just some of the ones. Because you love making predictions. And I know sometimes they're right and sometimes they're wrong. I mean, that's the nature of predictions, I suppose. But one of the things that struck me as I looked at some of these predictions was that do you think that some of these will leave the world lonely?

[Gary Vaynerchuk]

That's a great question. I am very in belief of the conversation around loneliness is another version and another topic in our current society that continues to miss the point of accountability in modern parenting.

[Interviewer (possibly a female media professional or podcaster)]

Okay, what does that mean?

[Gary Vaynerchuk]

That means it's very easy to not be lonely in today's world because of technology. And it's very easy to be lonely in today's world because of technology. I don't think the technology is the driver of loneliness. I believe that the way we are holding people accountable, the way we parent the energy of the way the human journey is going is a much needed combo. For example, loneliness is also being communicated because we now talk in the world about our feelings in a different way than we used to. Right. I think we can all agree with that now. I think we've come a great way in some ways. I think it's super awesome that it's not 1967 and every single person on earth has every feeling in their stomach and no one can talk. On the flip side, we live in a world right now where people literally. So we really track this stuff at Vayner where people literally in their social have been out four nights this week and on Saturday will post a tweet and be like, I'm lonely now. I don't think going out means you're not lonely. Cause you could be in your head lonely. But I think there's a lot going on on this issue. I believe that digital is the gateway drug to being less lonely. People meet on Instagram, DM and on Tinder and then go out and have a date with each other. The technology's in place for us to be less lonely. I believe the self esteem issue is why people are lonely. And I think that is the big conversation.

[Interviewer (possibly a female media professional or podcaster)]

It's not that I blame technology because.

[Gary Vaynerchuk]

I'm not saying you do.

[Interviewer (possibly a female media professional or podcaster)]

No, no. I just mean like when we do the longest table, one of the ways we let people. People know to come to the longest table is by posting on Nextdoor.

[Gary Vaynerchuk]

Correct? Of course, of course.

[Interviewer (possibly a female media professional or podcaster)]

In fact, we do storytelling. The way that's right. Tables have happened around the country is because people have posted stories.

[Gary Vaynerchuk]

And so let's break that down.

[Interviewer (possibly a female media professional or podcaster)]

Okay.

[Gary Vaynerchuk]

And then someone's on the other side and sees that and they decide if they're going to go outside.

[Interviewer (possibly a female media professional or podcaster)]

Yeah. Or decides to host their own table, by the way. Which is what's happened.

[Gary Vaynerchuk]

Correct.

[Interviewer (possibly a female media professional or podcaster)]

So for me, technology is an enabler.

[Gary Vaynerchuk]

It's the exposer.

[Interviewer (possibly a female media professional or podcaster)]

Right.

[Gary Vaynerchuk]

It's the great exposure. But people stood at home, stayed home and watched PBS and read books in 1984 and never.

[Interviewer (possibly a female media professional or podcaster)]

I will say, I do think there's a difference.

[Gary Vaynerchuk]

Please.

[Interviewer (possibly a female media professional or podcaster)]

Because I think when I was in middle school, you know, as the outsider kid in middle school, if somebody was having a party, I had no idea because I wouldn't know. I was in my home wondering where everybody was reading a book.

[Gary Vaynerchuk]

It's not true.

[Interviewer (possibly a female media professional or podcaster)]

How would I have known?

[Gary Vaynerchuk]

Because I just. I love you with all my heart. I think you knew.

[Interviewer (possibly a female media professional or podcaster)]

I didn't. I mean I.

[Gary Vaynerchuk]

You might have not known. A play date. But a birthday party. Yes.

[Interviewer (possibly a female media professional or podcaster)]

Okay. Yes, A birthday party. But I wasn't also sitting at home like watching them all gather.

[Gary Vaynerchuk]

Yes. But you know what you would do today as a 14 year old that wasn't invited to the party? You would go on Twitch. You would go play video games and find your friend that lives in Cincinnati. There are many people who use technology to create more friendships. I guess what I'm saying is I think it's a net neutral and I think the combination of how we talk about everything these days is a factor. And two, the ones that continue to struggle with loneliness, there's the enablers around them. Parents have always been enablers. We've become remarkable at it. By the way, I have a 16 and 13 year old. I'm not pointing fingers. I'm talking about things in the general. Yeah, I mean I'm not scared of. I'm not scared of AI making us lonelier. I'm really not.

[Interviewer (possibly a female media professional or podcaster)]

No, I'm not. I don't.

[Gary Vaynerchuk]

I'm not saying, I'm not saying you are.

[Interviewer (possibly a female media professional or podcaster)]

I'm just suggesting that we're both.

[Gary Vaynerchuk]

I'm just trying to answer the question.

[Interviewer (possibly a female media professional or podcaster)]

But I go back to, you have teenagers, so how are you parenting differently than what then what you say most society is doing, which is causing these problems?

[Gary Vaynerchuk]

I'm trying to communicate to them when I think they're going into patterns that may lead to what I deem as insecure mindset. So when my son, after a basketball game, he's very good, which is probably why I'm bringing it up. I love bragging about it. Like every parent, when he looked, even though he's actually very damn good and it's crazy to me, he's this good. When he looks for excuses that I just watched were not true. I won't let him get away with that. He'll be like, kenny did. I'm like, kenny didn't do that. You set up one of your rules.

[Interviewer (possibly a female media professional or podcaster)]

No complain.

[Gary Vaynerchuk]

You know, listen, I think we took it too far in our family. Cause then we didn't talk about feelings. So I think everything. By the way, everything. We're talking, by the way. Last five minutes, everyone. Everything's about purple, right? If anything, I hope actually it's all about gray. Yeah, exactly. It's the same thing. I use purple now. Cause everyone's locked into blue and red. And I'm like, purple, purple, purple. All of this is purple. There is. You know, when I'm like. I really. You know, a lot of times when I'm like, this is what's happening with AI. It's because I'm trying to give another context, point to what I watch the masses lazily leaning into, like, this is all gonna be bad. I'm like, really? Cause that's what we've said about everything. You know, like the tractor. Do you know this, man? We all worked on farms. The tractor's invented. Everyone's like, everyone's gonna be out of a job. We went on to do bigger things. Like, we. I promise you, on the record, I can't wait for this to be played in 100 years when I'm long gone. I hope they have a party around this clip. We are about to go on to much more remarkable things because of AI.

[Interviewer (possibly a female media professional or podcaster)]

Now, I'm not doing.

[Gary Vaynerchuk]

I'm not saying you are. I'm not saying you are.

[Interviewer (possibly a female media professional or podcaster)]

I'm going to agree with you, which I know is shocking.

[Gary Vaynerchuk]

No, not from the way I view you. I actually think we see things similar.

[Interviewer (possibly a female media professional or podcaster)]

I think the world is gray. And what I worry about is how most people feel so certain in their conviction about things. The more I know, the less I know. And. And yet I feel like people are just so convicted about their beliefs in ways that I really can't believe.

[Gary Vaynerchuk]

My thing about practical optimism, which is what I think I'm spewing anyway.

[Interviewer (possibly a female media professional or podcaster)]

If you hear noise, it's the dog.

[Gary Vaynerchuk]

Yeah, it's awesome. Where I'm at with practical optimism, I mean, I had a great dinner last night where, like, we really got into it with a group of, like, six people. I'm like, okay, I'm going on history with context. You're saying it's over. My question to you is, if you actually believe what you're saying, you better Change your behavior. If you think it's all ruined and it's all wrapping up here in the next 10 years, why are you not going to the airport right this morning? Like, why are you going to your job? This is what I said to the people. I'm like, where the fuck are you doing? Are you going to work tomorrow? It's literally when I went with my chest. I'm like, are you going to work tomorrow? Yeah. I'm like, the fuck are you doing now? You just told me in 10 years it's all over. We're dead. It's all over. The fuck are you doing? So I just think that people love to wallow in negativity. I think we're a bunch of hogs moping around in mud. Woe is me. This sucks. Pointing fingers to everyone. Here's a big one. I just need to get this off before I'm out of here. I want to ask you a question. At what age is it appropriate for you to decide you're a grownup and stop blaming your parents for everything in your life and realizing you are now a grown up up and you can do actions to mitigate the pain you're feeling? What age do you think that is?

[Interviewer (possibly a female media professional or podcaster)]

That happened to me when I was young.

[Gary Vaynerchuk]

I get it. I'm not asking you or me in society.

[Interviewer (possibly a female media professional or podcaster)]

I actually think you have to do that at any age.

[Gary Vaynerchuk]

I agree. What age? What age do you respect? I actually on a show the other day, because we got hot on this, I went with 25 because I just decided to give a couple more years of grace to kids. Yeah, exactly. I like the fully developed. I like the fine like I'm trying to find some. You know what I mean? I was like, but fuck, man, I'm around unlimited. 30 and 40 year olds. All they want to talk about is what their mom. They tell me the same story 400 times. I'm like, I know you. I'm like, I've been your friend for 25 years. I remember your mom. I know what she did. The fuck are we doing here? How much do you want to fucking slop in this slop? We're fucking slopping and slop. All right.

[Interviewer (possibly a female media professional or podcaster)]

We're not going to be slopping and slop here.

[Gary Vaynerchuk]

Okay?

[Interviewer (possibly a female media professional or podcaster)]

We're. I'm gonna go. Don't you worry.

[Gary Vaynerchuk]

Rapid fire.

[Interviewer (possibly a female media professional or podcaster)]

Okay. Biggest myth that still haunts you.

[Gary Vaynerchuk]

I don't struggle with regret. But the biggest one that everyone knows about is I passed on Uber. Who? Travis was my best bud. He's the only person I mentioned in my first book, crush it outside my family. We were that close. I did something that I don't believe in, which is scared money doesn't make money. I just bought my first big boy apartment. I had very little in savings that was comfortable to me. He came to his credit. He came back a second time. He's like, bro, how can you not be in. I just fucked. And that $50,000 check would have been $540 million. So that one didn't work out.

[Interviewer (possibly a female media professional or podcaster)]

Okay, one piece of advice. You now think was wrong.

[Gary Vaynerchuk]

That's a great question.

[Interviewer (possibly a female media professional or podcaster)]

You're like, I just gave one.

[Gary Vaynerchuk]

I'm just kidding. I often back to candor. I often told kids when I was growing up to find relationships that were easy. You know, like, it has to be easy. And I realized that was me avoiding, in hindsight, conflict. And I think that led to less authentic relationships at times. And so luckily, I stopped saying it by the time I made content publicly. So there's not a lot of videos of me saying, I don't think there's any, by the way. But I will tell you the real answer because I want to be vulnerable and real, and I hope this helps someone. My historic advice that I gave in my 20s and early 30s, before I made content, or when I was only making wine content to my inner circles and the people that would listen to me, was, relationships should be easy. And that's not true. Relationships should be real.

[Interviewer (possibly a female media professional or podcaster)]

It can be hard.

[Gary Vaynerchuk]

Yeah.

[Interviewer (possibly a female media professional or podcaster)]

Okay. One sentence your mom would say about you.

[Gary Vaynerchuk]

He has a golden heart.

[Interviewer (possibly a female media professional or podcaster)]

I like that one. He's a superhero.

[Gary Vaynerchuk]

She always said, you have a golden heart, and that mattered to me. That's what I wanted to aspire to.

[Interviewer (possibly a female media professional or podcaster)]

What advice would you have for someone who needs to pivot?

[Gary Vaynerchuk]

That staying in the thing that you're in is worse than if the pivot goes catastrophically wrong

[Interviewer (possibly a female media professional or podcaster)]

advice for a recent graduate.

[Gary Vaynerchuk]

So much. Get off mommy and daddy's payroll at all costs at all costs. Live with nine friends and eat garbage food. Get off of their payroll at all costs. Number two, 22 to 30 should be nothing but high risk, high reward behavior because you'll never have a framework that's that easy to go after your dreams. And you've got to scratch that so you don't sit with regret the back half of your life. Those two stand out for me.

[Interviewer (possibly a female media professional or podcaster)]

Okay, if you're gonna try be a content creator today, you would.

[Gary Vaynerchuk]

I would deploy self awareness. Figure out if you like writing, if you like gift of gab. Do you like being on Camera. Do you not? Content creation comes in many forms. I'm loving the rise of substack. I'm so happy for writers. I won on the rise of video because this comes natural to me. But I can't write for shit. All my best selling New York Times books. Audio. I literally have to. Audio. I have to talk my way into books. So be self aware of what medium you like and then understand that volume of content is not subjective, but the quality is.

[Interviewer (possibly a female media professional or podcaster)]

What does that mean?

[Gary Vaynerchuk]

It means that people do not understand how important volume is.

[Interviewer (possibly a female media professional or podcaster)]

Oh, my God. You know who does? You.

[Gary Vaynerchuk]

Yes, I do. And I would say that understanding the distribution of our day, which rewards volume and understanding that is this good, is completely subjective. Do you guys like my sweater? Do I like that? I love that photo, actually. Jesus Christ. That's awesome. You know, like, most things are subjective. The amount of output is not. And a lot of people from our world love high fidelity and production value and their opinions. And so I think that holds a lot of people back.

[Interviewer (possibly a female media professional or podcaster)]

I can't thank you enough for coming on. Did you have one final question back

[Gary Vaynerchuk]

on the self esteem thing and we'll let you go for a second. Jets jersey.

[Interviewer (possibly a female media professional or podcaster)]

Oh, yeah. Oh, yeah. Okay. You've told the story about your mom and the jets jersey. I know you still want to own the Jets. Yes, we know.

[Gary Vaynerchuk]

We're gonna pray for that for you.

[Interviewer (possibly a female media professional or podcaster)]

She make. She knitted you a Jets jersey, and I know you prized that. First of all, what was the number? Who was the player?

[Gary Vaynerchuk]

Pat Leahy was number five, the kicker at the time. But that wasn't why I did it. I did it because five was my favorite number when I was seven, I think because I decided my favorite number when I was five, and since I was five, it became my favorite number. I don't really recall the origin of that. Yeah, it's the most emotion, most emotional story of my life. Like, every kid in the neighborhood had a Jets jersey. We're playing Nerf football all the time, infatuated with football. I would argue that football, American football, was my coming to America, my Americanization moment.

[Interviewer (possibly a female media professional or podcaster)]

I love being a cheerleader.

[Gary Vaynerchuk]

There you go. So you get this a lot. It's very young. We're playing every day. Everybody has a Jets jersey. I want one. I asked my mom. The answer is no, because immigrant families don't buy $20 jets jerseys. And unbeknownst to me, every night, my mom knitted me similar to this, actually a jersey for me to wear.

[Interviewer (possibly a female media professional or podcaster)]

And did you wear it or did you wear it because you were like, oh, it's not like everyone else's.

[Gary Vaynerchuk]

No, I wasn't bespoke. No. Yeah. I wasn't embarrassed. I didn't think it was worse. I wore it proudly all the time.

[Interviewer (possibly a female media professional or podcaster)]

And that actually says a lot about you.

[Gary Vaynerchuk]

Yeah, it was there early, you know, to your point, I haven't thought about that. Like, my ability to tune the outside. My mom said I was the best, and I believed her. And there was nobody outside the door that was going. Going to tell me otherwise. And that's my life.

[Interviewer (possibly a female media professional or podcaster)]

That's a perfect place to end. Gary, thank you so much for coming.

[Gary Vaynerchuk]

Thank you, everybody. 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.