Gary Vee: Forgiveness, Fear, and the $540 Million Mistake (Replay)

In this re-release of one of our favorite episodes, Gary Vaynerchuk opens up to Maryam about fear, self-esteem, forgiveness, AI, leadership, and what he believes is a growing crisis of “late adulthood.” Gary shares why so many professionals feel stuck — not because of burnout, but because of insecurity and unresolved resentment. He breaks down his philosophy on kind candor vs. radical candor, why fear is the real career killer, and how over-coddling may be delaying independence for an entire generation. From parenting teenagers to leading thousands of employees, Gary explains why self-worth is the operating system behind success — and why forgiveness (especially of yourself) might be the most underrated personal development tool of all. If you’ve ever felt behind, afraid to pivot, or unsure of your next move in the age of AI, this episode is for you.

Key Moments

00:00 — Forgiveness Is the Answer We’re Avoiding ❤️‍🩹
Gary opens with a bold claim: most people are emotionally “clogged” because they’re holding resentment. He explains why forgiveness — especially forgiving yourself — may be the most underrated growth tool.

02:46 — “Nice Guys Finish First” 🏆
Gary unpacks the tension between competitiveness and kindness — and why he believes you can be fierce in business without losing your humanity.

05:17 — The Late Adulthood Crisis 🚨
Are we raising adults who aren’t ready to be adults? Gary shares his controversial take on over-coddling, privilege, and why independence matters more than ever.

08:52 — Why He Doesn’t Fear AI (And You Shouldn’t Either) 🤖
Using historical pattern recognition, Gary explains why AI is just the next evolution — not the apocalypse.

14:18 — The Self-Esteem Conversation Nobody Wants to Have 🧠
Gary breaks it down: almost everything — career fear, content paralysis, insecurity — comes back to self-worth.

15:33 — The Rejection He Was Actually Afraid Of 💔
Despite fearless business moves, Gary admits he was afraid to ask girls out in high school. A revealing look at how fear shows up in unexpected places.

18:38 — Kind Candor vs. Radical Candor 🎯
Gary shares his leadership “kryptonite” — struggling with candor — and why he now believes honest feedback must come with kindness.

28:57 — Walking Away From the Family Business 🏪
After building his dad’s liquor store into a $65M company, Gary explains why leaving wasn’t guilt — it was growth.

31:14 — Maximizing Joy vs. Maximizing Money 🔥
Why Gary doesn’t optimize for profit alone — and how curiosity drives his many ventures.

33:35 — Call Your Mom. Forgive Yourself. 📞
One of the most emotional moments of the episode. Gary urges listeners to make the call — to forgive others or themselves.

43:53 — At What Age Do You Stop Blaming Your Parents? 🧨
Gary poses a provocative question: when do you fully own your life? A raw discussion about responsibility and adulthood.

47:46 — The Jets Jersey Story 🧵💚
Gary shares the powerful story of his mom knitting him a Jets jersey when they couldn’t afford one — and how that shaped his confidence forever.

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Transcript

SPEAKER_00 0:00

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

SPEAKER_01 0:05

What does that mean?

SPEAKER_00 0:06

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.

SPEAKER_02 0:16

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

SPEAKER_00 0:24

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. Forgiveness is a wildly underutilized, not talked enough about action and trait. 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.

SPEAKER_02 1:11

Today we're gonna have on Gary Vee, commonly also known as Gary Vaynercheck, but he only needs one name. Why? Because he's an icon of the advertising and media business. He has his hands in everything, from a character business to nine best-selling books to media company to private club. I mean, Gary Vayner is an influencer with millions and millions of followers. An immigrant kid who made his way here and now is the ultimate insider, although I'm not sure he would say that. Today he came on and we had a lot of messy bits, including the dogs and lots of other noise. And he told me not to cut it out or stop the rolling because that's actually what makes it all even that much more authentic. Here we go. So, Gary, I am so excited to have you here. I know that the audience is going to be particularly excited to have you here because you have like a rabid following, which is amazing. You and I met when you were at the early days of starting Vayner Media. Yes. 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 I think it's such an interesting story about you because you're a man of contradictions. 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?

SPEAKER_00 2:41

Yes.

SPEAKER_02 2:42

You talk a lot about, you know, wanting to win and slitting throats, but at the same time, you also talk about kindness. What is that contradiction about for you?

SPEAKER_00 2:52

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. 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 before I start.

SPEAKER_02 3:25

Well, I wasn't thinking you were gonna come here and okay, good.

SPEAKER_00 3:28

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 is 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 I'm competitive, I'd like to win. I am uh 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, predominantly because I got so many of them from her. And so, yeah, I mean, I think nice guys finish first. To your point, like they You actually think that? I I know that because I 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. I want to build these things, but I want to build them for the sake of building them. You know, I don't build businesses to buy a third home or a golf course or a private jet.

SPEAKER_02 4:58

So, like me, you were an immigrant. Yes. And you were a kid who came here not speaking English, you know, living in a house in a small apartment with lots of people, right? Like, not easy.

SPEAKER_00 5:07

Studio in Queens, eight family, like real tight.

SPEAKER_02 5:10

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

SPEAKER_00 5:14

You know, I was very young. I was four, five, six in those environments. I'm fascinated by growing up early, and I'm fascinated by growing up late. What does that mean? I think too many parents are treating their 27-year-olds like they're 2.7 years old. Oh, I see. We have a real issue. 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 for in the world.

SPEAKER_02 5:42

Well, it's kind of a privilege.

SPEAKER_00 5:44

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 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 five. Yeah. And my dad lost his dad at 15. And they lived in the USSR and they immigrated to America at 20. They were grown early. I was grown early.

SPEAKER_02 6:24

I was grown early.

SPEAKER_00 6:25

I get it. People with immigrant stuff, like I actually 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 overcoddling thing, it's an adversity thing. But, you know, it 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.

SPEAKER_02 6:53

It's interesting. So you're recently 50.

SPEAKER_00 6:55

Yes.

SPEAKER_02 6:56

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 CMO jobs one after the other.

SPEAKER_00 7:05

Yes.

SPEAKER_02 7:05

Which I know you know it's not easy. No. Um, you know, you're just in the hustle.

SPEAKER_00 7:09

Yes.

SPEAKER_02 7:10

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 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.

SPEAKER_00 7:25

No.

SPEAKER_02 7:26

Well, you're a parent. Hold on. Sure, but you're a parent.

SPEAKER_00 7:29

Go ahead.

SPEAKER_02 7:29

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 of, you know, I didn't want my kids to have to survive revolution, you know, lose their father, blah, blah, blah. Of course. In order to be resilient. Of course. And I worry about their resilience because that's a hard thing to pass down, right? Because it was a circumstance.

SPEAKER_00 7:52

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

SPEAKER_02 7:53

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

SPEAKER_00 7:56

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

SPEAKER_02 8:02

Ah, interesting.

SPEAKER_00 8:03

It was a different no.

SPEAKER_02 8:04

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

SPEAKER_00 8:08

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, he passed away right after. But I spent almost all my time with either my mother, but my mother had was just about to have another baby, and we had my sister pretty early. 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. I don't know if if it's nature, nurture, but I've been 80 my whole life. I've been reflective my whole I was a terrible student, but I was great at history. I would argue that all of the accolades I get as a businessman about seeing around corners, early investor in all these things, has a lot to do with historical pattern recognition. I lack fear.

SPEAKER_02 8:59

What does that mean? Historical pattern recognition.

SPEAKER_00 9:01

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. 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 that becomes the data points that I make decisions on.

SPEAKER_02 9:27

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 perfectly honest.

SPEAKER_00 9:35

You also are living it and you know what the downside is. Yeah. You know, when you're born into something that's remarkable, you're confused of what bad is. 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. 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, you know, late back to reflection, at like 35, I called my sister one day. I'm like, wait a minute. We we were a little bit better than we thought. It's just that mom didn't buy us anything. You know, it was just that kind of life. Nonetheless, uh, 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.

SPEAKER_02 10:21

I is that really true?

SPEAKER_00 10:23

It is really true. 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.

SPEAKER_02 10:36

No, I I understand that, but at the same time, you know, one of the things that happens when you 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 we don't like change, humans, right? And you actually thrive in change. I love change.

SPEAKER_00 11:04

God, I love it. I'm practical. How can you not like change? It's the it's the most true thing that will happen. It's the only constant. It's the only con I 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 Vayner Media who've known me for a decade and they're like, What is this? I'm like, This is Vayner Media. 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.

SPEAKER_02 11:46

What does that mean? What does associating with the COO mean?

SPEAKER_00 11:50

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 if but in my soul, I like being practical and operating. That's the stake. Everything else is the side dish, the sizzle, the amoose spoosh, and the dessert. And I think it speaks to change. I just don't even have the audacity to not like change.

SPEAKER_02 12:19

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 sometimes that's good and sometimes that's not so good. Most people are not built that way. And that's it's human nature.

SPEAKER_00 12:32

Yes, most people really struggle with the outside noise.

SPEAKER_02 12:35

Right. So today, in a world where AI is coming in and people are so concerned. 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. For now. For now. But there's a real thing, right? And so there's a real fear as what's going on in the market. What advice do you have on a practical level? Because you are an operator. What advice do you have for somebody?

SPEAKER_00 12:59

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, A, I 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. You could.

SPEAKER_02 13:20

But you know how many people, it's so funny because I watch so much of your content, and um, what struck me is you know, you do content just anywhere. It doesn't always have to be perfect. You said here, if an ambulance comes, why would you stop it? Right. Okay. 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.

SPEAKER_00 13:46

Yeah.

SPEAKER_02 13:47

But the new world of media, which is not, you know, CBS evening news, that's right, is very different. And in fact, if you go on a TikTok, a lot of it, it does better if it's messy.

SPEAKER_00 13:57

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.

SPEAKER_02 14:19

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

SPEAKER_00 14:25

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 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.

SPEAKER_02 14:50

Well, first of all, I want to dig into the self-esteem question because I'm curious to know if you think you have self-esteem or if you always had it, but hold that thought for a second. 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.

SPEAKER_00 15:08

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 NCAPs 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.

SPEAKER_02 15:34

There's so many threads in the conversation between you and me, which is what I predicted. Did you always have confidence?

SPEAKER_00 15:40

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 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 because I feared the no. 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 going to be a garbage man. By today's standard, it seems inappropriate. A lot of us in this room right now grew up in an era where that was just kind of normal. It wasn't like super inappropriate. That's what authorities did. Like, not only them, my friend's parents, you know, as we started getting into high school years, hung out with kids that got A's and had ambitions. And I could feel some of their parents being like, you need to cut that one because he gets these DNF. And I was, you know what's funny? I was such a good kid. I never drank, I never did drugs. I'm such a nice boy. I sold baseball cards in the malls of New Jersey when I was 12 years old, all grown-ups 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. 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 five and ten than I did. I probably cried every day. Do you cry now? I I am very easily triggered into crying. I just watched Song Song Blue. Oh, yeah. Like I barely held on in a couple of spots. I cried on a very big date, my senior of high school, at Lion King when the dad dies. I cried. That did not go over well in 1994. Did that end the date? That ended that ended the upside of the date for sure. Um, and so like, yeah, like I'm 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.

SPEAKER_02 18:08

So 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 um giving feedback or conflict.

SPEAKER_00 18:17

That I don't know if that was empathy. 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, because 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 candorous, which is wild because as you know, Gary V, especially in the Ad land, I came out guns ablazing with my my candor is I rewatched your big keynote that led to the book. Love that. That's a wild one. You know, so like, you know, my candor, even in this interview, my candor is 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 clock on me not being as well at giving you candor. As, you know, I've been a boss since I was 17 years old. I was managing everyone in my dad's liquor store. So I was a child. You know, my mom is also not overly candorous, and my father was inappropriately candorous 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 raised by someone that is, I, if it isn't obvious to everyone here, is my North Star, is what 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. We 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 seeing than help you. Now I understand it to be help. I hated the thought that I was gonna deposit something you were gonna have to sleep with tonight because I hate fear. I fucking hate fear. I hate that the world weaponizes it. I I my relationship with fear is not only do I not fear you, fear, I'm gonna fucking kill you, fear. 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 it. And once I wrote a book about it, it 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 call it kind candor. And and I've rolled that out to all my organizations because 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.

SPEAKER_02 21:14

So it's funny, you know, I having worked in a lot of different companies when I got to tech radical candor, as you know, was a thing because it was really Netflix's thing. It was hot. Right. It was hot. Yep. And I, like you, didn't like making people uncomfortable. I mean, I wasn't afraid to do it, but I didn't like it. But I I did learn later, like that it was really helpful to give people feedback early, but how you give that feedback is everything. I mean, it's everything. I mean, 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.

SPEAKER_00 21:48

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. 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 it's a muscle. It's a 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 I know humans can do it.

SPEAKER_02 22:32

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.

SPEAKER_00 22:44

I think there's a lot there. So my brother and I started Vayner Media in 2009. I'm 34. I just spent 12 years working 100 hours plus a week in a box, a store with my father. He started the company, but I'm the driver of the business.

SPEAKER_02 22:59

You have no equity.

SPEAKER_00 23:01

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

SPEAKER_02 23:06

Did you get a bonus?

SPEAKER_00 23:09

You're poking. Like sorry, it was an absolute. No, no, no. And you know what's so funny? I very much understand my father. We we barely got that. It was really intense. It was real immigrant shit. 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, you know, I'm gonna be 73, God willing. You know? 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. We started the company 50-50 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 gonna 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 on what the business became. And when we started Vayner Sports, even though he was running it full time, the equity was different in my favor, even though he was running it.

SPEAKER_02 24:06

And everything we've done subsequently, we we we have I mean, we all know families aren't easy, particularly to I mean, I work with my husband, so I say this to you as somebody who has familiarity, and I and I really enjoyed and I'm grateful for it, but it's not easy.

SPEAKER_00 24:18

No, it's not easy because you're blurring lines. It's it my brother and I have had it easy. My father and I had it incredibly challenging, yet wildly easy in the macro. It is, it's could I mean I wish it on everyone. And we 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 cried 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, because 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 and I knew I would have more time. I knew who I was. 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 seven or eight, nine, thirteen 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.

SPEAKER_02 25:48

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

SPEAKER_00 26:03

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, 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, because I know what's going on with a lot of parents that have 25-year-olds. There's a lot going on right now, and a lot of what the world's upset about and 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 that's kind of where I was at.

SPEAKER_02 26:40

Sorry. Yeah, I call my, oh, I'm sorry. Yeah, I know. Thank you.

SPEAKER_00 26:42

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 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. Dad's tough, like, you know, and he's the best. I mean, I'm I want to make sure I'm painting a very clear picture. My dad in his, you know, my dad's a cactus.

SPEAKER_02 27:05

You can love him and he can still be tough.

SPEAKER_00 27:07

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. Anyway, nonetheless, I really broke down. 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. Uh I just remember how I felt. I'm sure it was lots of encouragement. But I, my dad and I, 80% of the time it was wonderful, 20% of the time there was real contention.

SPEAKER_02 27:40

Hard to leave when you have a choice?

SPEAKER_00 27:43

No, because my dad wanted it too. Let's talk about the other side of the story. My father comes to this country with a hundred bucks. He works his face off every minute to have his own liquor store business. He's an old school man. He's the man. Here comes his son.

SPEAKER_02 27:58

Yeah, that had to be.

SPEAKER_00 27:59

Son starts to work around the store. First, he's just happy that the son's not a schlamel 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.

SPEAKER_02 28:17

Yeah, not so fun.

SPEAKER_00 28:18

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.

SPEAKER_02 28:44

So you had no like sense of guilt.

SPEAKER_00 28:47

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 power, which is the only thing he actually wants right now. I felt like a hero. 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 like that for you. You know, that was oh, that was I mean, when my dad asked me to help.

SPEAKER_02 29:09

That had to have been so difficult for him.

SPEAKER_00 29:12

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 bit.

SPEAKER_02 29:20

We know a lot of those people who would have just ripped. Died on the ship.

SPEAKER_00 29:22

I, 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.

SPEAKER_02 29:37

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

SPEAKER_00 29:44

Yes, I am.

SPEAKER_02 29:45

Pickleball, V friends, 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 every right when you are focused single-mindedly on that wine business versus having like to share your interest across six things? I joke now, I have six jobs. It's very hard to be good at six jobs.

SPEAKER_00 30:06

You're right.

SPEAKER_02 30:06

How do you think about that?

SPEAKER_00 30:08

Easily. Um, that is such a lie. 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 cover, 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 Flagfish Club downstairs. I have seven to ten alternative sports investments: pickleball, wiffleball, uh, unrivaled, the women's basketball league, the sailing league. I'm really deep in alternative sports. I have a 2,500-person Vayner media that people know, V friends, people are starting to get know more and more. I still quietly run the wine business through my best friend and we do wine text. I have a lot going on. Let me tell you why the answer is easily.

SPEAKER_02 31:12

Okay.

SPEAKER_00 31:13

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.

SPEAKER_02 31:22

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

SPEAKER_00 31:24

Do I believe that if I spent every minute on VaynerX or Vayner Sports or VFriends or VCR, that that thing could go? And one could argue, definitely VaynerX, Vayner Media, 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 Vahner eats up every minute. The fact that I can hack 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.

SPEAKER_02 32:17

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

SPEAKER_00 32:21

I'm inherently wildly curious. You're you nailed it. I 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 V. 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 gonna 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. Like I just, I'm just 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.

SPEAKER_02 33:10

Well, okay, so for people listening who are like, I don't, I'm not in touch with my body. Like, what are you saying? Yes. How does one get in touch?

SPEAKER_00 33:20

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 shrooms trip. I don't fucking know. Like for some people, it's forgiving people that they're mad at. That's one. Let me go in down this path for a second. Okay. I believe forgiveness is the answer to the quiz that many people are struggling with right now.

SPEAKER_01 33:42

What does that mean?

SPEAKER_00 33:43

I believe I believe the dogs can sense I'm going somewhere big. I think they can female man.

SPEAKER_02 33:49

You know, it's New York.

SPEAKER_00 33:50

But I think it was more that they, you know, they have a different sense. I think they know where I'm going.

SPEAKER_02 33:54

The dogs are like, what's happening?

SPEAKER_00 33:55

Here it is. I'm giving the big answer. Uh 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.

SPEAKER_02 34:08

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

SPEAKER_00 34:16

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. Forgiveness is a wildly underutilized, not talked enough about action and trait. 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.

SPEAKER_02 34:57

You know, we started this thing called the longest table, where we put the table down the block and invite neighbors to a Pollock, 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? Have you monetized it? Like, what's happening? It's literally the immediate reaction. And when I say, Well, 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 we're not three volunteers trying to, you know, band-aid it together, but the goal wasn't money.

SPEAKER_00 35:29

Right.

SPEAKER_02 35:30

And it's very confusing to people.

SPEAKER_00 35:33

Not to me. I mean, this is if we just want to go there, I'll go there with you. Like I'm not even sure any of my business behavior is 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 sh 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.

SPEAKER_02 36:05

So I I buy that, but on the flip side, you know, as a kid who also had financial insecurity growing up, there was a sense of also having to pay my bills. Like I didn't want collection agencies to come ringing at my doorbell.

SPEAKER_00 36:18

I had something very good happen, which was I never even knew of a concept of not living within your means.

SPEAKER_02 36:26

Yeah, I never believed in borrowing money or credit card debt. So I relate to that.

SPEAKER_00 36:30

I literally thought as a grown-up, I would not have a credit card. That's how anti-credit card, like I so, 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 trillion dollars when you came from nothing, literally in 1988, I'm making five, 300 bucks at a card show. 10 years earlier, my family has a hundred bucks to their name. So it, you know, very quickly, my talents in this capitalistic USA, USA, like 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 gonna live a $35,000 a year life, that's that. So what am I scared of?

SPEAKER_02 37:23

Okay, so now I want to go to the some of the predictions you've made. Hold on, I spilled on myself. It's so good thing, it's called the messy parts. It gives a lot of work, a lot of things. Exactly. 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?

SPEAKER_00 38:04

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. Loneliness is also being communicated because we now talk in the world about our feelings in a different way than we used to. 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 because you could be in your head lonely. 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 is 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.

SPEAKER_02 39:14

I I I I'm It's not that I blame technology because I'm not saying you do no no, I just mean like when we do the longest table, one of the ways we let people know to come to the longest table is by posting on next door, Facebook, or Instagram. Of course. In fact, we do storytelling. The way 50 tables have happened around the country is because people have posted stories.

SPEAKER_00 39:34

And so let's break that down.

SPEAKER_02 39:35

Okay.

SPEAKER_00 39:35

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

SPEAKER_02 39:40

Yeah, or decides to host their own table, by the way, which is what's happened. Correct. So it I for me, technology is an enabler.

SPEAKER_00 39:46

It's the exposer, right? Okay, it's the great exposer.

SPEAKER_02 39:50

But 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.

SPEAKER_00 40:00

It's not true.

SPEAKER_02 40:01

How would I have known?

SPEAKER_00 40:02

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

SPEAKER_02 40:06

I didn't.

SPEAKER_00 40:06

I mean, I had to You might have not known a play date, but a birthday party?

SPEAKER_02 40:10

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

SPEAKER_00 40:16

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 where 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 there's the enablers around them. Parents have always been enablers. We've become remarkable at it. By the way, I've a 16 and 13-year-old. Yeah. Like I'm not, I'm not pointing fingers, I'm talking about things in the general.

SPEAKER_02 40:54

But I go back to you have teenagers actually. So how are you parenting differently?

SPEAKER_00 41:00

Than what?

SPEAKER_02 41:01

Than what you say most society is doing, which is causing these problems.

SPEAKER_00 41:05

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. 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 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 that. I'm like, Kenny didn't do that.

SPEAKER_02 41:28

You said Yeah, one of your rules, no complaining.

SPEAKER_00 41:30

I think we took it too far in our family because 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? I if anything, I hope.

SPEAKER_02 41:39

I say it's all about gray.

SPEAKER_00 41:41

Yeah, exactly. It's the same thing. I use purple now because everyone's locked into blue and red. And I'm like, purple, purple, purple. 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? Because that's what we've said about everything. Like the tractor. Do you know this, Mary? Like, 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 a hundred years when I'm long gone. I hope they have a party around this this clip. We are about to go on to much more remarkable things because of AI.

SPEAKER_02 42:23

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

SPEAKER_00 42:25

No, I not not from the way I view you.

SPEAKER_02 42:27

Yeah, I actually think we see things a little bit. I think the world is gray, and what I worry about is how most people feel so certain in their conviction about things. I the more I know, the less I know. And yet I feel like people are just so convicted about their beliefs in ways that I really can't relate to.

SPEAKER_00 42:43

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

SPEAKER_02 42:46

Well, if you hear noise, it's the dogs. Yeah, so just ignore that.

SPEAKER_00 42:49

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. 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 tomorrow? Are you going to work tomorrow? This is literally when I went when I went with my chest. I'm like, are you going to work tomorrow? Yeah, I'm like, the fuck are you doing that? 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 grown up and 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? What age do you think that is?

SPEAKER_02 44:00

That happened to me when I was young.

SPEAKER_00 44:02

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

SPEAKER_02 44:04

I think I actually think you have to do that at any age. I agree. And I'm going to forgiveness. What age you? 21.

SPEAKER_00 44:12

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.

SPEAKER_02 44:20

Oh, that's when you're breaking development.

SPEAKER_00 44:23

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. What the fuck are we doing here? How much do you want to fucking slop in this slop? We're fucking slopping and slop.

SPEAKER_02 44:50

All right, we're not gonna be slopping and slop here. Okay, we're I'm gonna go to don't you worry. Rapid fire.

SPEAKER_00 44:57

Rapid fire.

SPEAKER_02 44:58

Okay. Um, biggest miss that still haunts you.

SPEAKER_00 45:01

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.

SPEAKER_02 45:31

That's a hard one. Okay. One piece of advice you now think was wrong.

SPEAKER_00 45:35

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.

SPEAKER_02 45:49

It can be hard. One sentence your mom would say about you.

SPEAKER_00 45:53

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

SPEAKER_02 45:59

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

SPEAKER_00 46:02

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

SPEAKER_02 46:09

Advice for a recent graduate.

SPEAKER_00 46:13

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 that's that easy to go after your dreams. And you've got to scratch that so you don't sit with regret on the back half of your life. Those two stand out for me.

SPEAKER_02 46:38

If you're gonna try to be a content creator today, you would I would deploy self-awareness.

SPEAKER_00 46:43

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 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. Be self-aware of what medium you like, and then understand that volume of content is not subjective, but the quality is. What does that mean? It means that people do not understand how important volume is.

SPEAKER_02 47:13

Oh my God, you know who does? You.

SPEAKER_00 47:15

Yes, I do. And and I would say that understanding the distribution of our day, which rewards volume, and understanding that is this good is completely 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.

SPEAKER_02 47:37

You've told the story about your mom and the Jets jersey. I know you still want to own the Jets.

SPEAKER_00 47:42

Yes.

SPEAKER_02 47:42

Which we know we're gonna manifest that for you. Um, she knitted you a Jets jersey, and I know you prize that.

SPEAKER_00 47:50

Yeah, it's the most emotional story of my life. Like every kid in the neighborhood had a Jets jersey. We're playing nerf football all the time. Um infatuated with football. I would argue that football, American football, was my coming to America, my Americanization mode.

SPEAKER_02 48:04

Mine was being a cheerleader.

SPEAKER_00 48:06

There you go. So you 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. Um, and unbeknownst to me, every night my mom knitted me, similar to this actually, uh, a jersey for me to wear.

SPEAKER_02 48:26

And did you wear it? Or did you not wear it because you were like, oh, it's not like everyone else's?

SPEAKER_00 48:30

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

SPEAKER_02 48:37

That actually says a lot about you.

SPEAKER_00 48:39

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 gonna tell me otherwise. And that's my life.

SPEAKER_02 48:51

That's a perfect place to end. Gary, thank you so much for coming. Well, you've made it to the end of the episode with none other than Gary V. I know it was memorable. We really appreciate you getting to the end here. Remember, like it, recommend it, tell 10 friends. That's what it takes because we're all here for the messy bits in between.