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Gary Vaynerchuk
I believe forgiveness is the answer to the quiz that many people are struggling with right now.
Podcast Host
What does that mean?
Gary Vaynerchuk
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.
Podcast Host
Sorry. Is forgiveness let it be or let it go? Or is forgiveness a combination of candor, like actually saying your piece?
Gary Vaynerchuk
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.
Podcast Host
Today we're going to have on Gary V. Commonly also known as Gary Vaynerchuk. 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 bestselling 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. Like a rabid following, which is amazing. You and I met when you were at the early days of starting VaynerMedia.
Gary Vaynerchuk
Yes.
Podcast Host
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? Yes, 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?
Gary Vaynerchuk
I don't see it as 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 say that.
Podcast Host
Well, I wasn't thinking you were gonna come here.
Gary Vaynerchuk
Yeah, of course not.
Podcast Host
Okay, good.
Gary Vaynerchuk
And then again, you know, 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 am probably frustrated. I didn't have the physical talents to be an athlet. 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 cause I got so many of them from her. And so, yeah, I mean, I think nice guys finish first. To your point, like, thank you.
Podcast Host
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. 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 or a golf course or private jet.
Podcast Host
So like me, you were an immigrant.
Gary Vaynerchuk
Yes.
Podcast Host
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.
Gary Vaynerchuk
Studio in Queens. Eight, like real tight.
Podcast Host
Right. Okay. So you definitely had to figure out how to be nice to get along.
Gary Vaynerchuk
You know, I was very young. I was 4, 5, 6 in those environments. I'm fascinated by growing up early and I'm fascinated by growing up late.
Podcast Host
What does that mean?
Gary Vaynerchuk
I think too many parents are treating their 27 year olds like they're 2.7 years.
Podcast Host
Oh, I see.
Gary Vaynerchuk
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. And well, it's kind of a privilege. 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. And they lived in the USSR and they immigrated to America at 20. They were grown early. I was grown early.
Podcast Host
I was grown early.
Gary Vaynerchuk
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 over coddling thing, it's an adversity thing. But you know, the kindness wasn't formed in those early Queens days. The kindness were formed from the womb. My cocoon of my life was my mother. And my mother is pure kindness.
Podcast Host
It's interesting. So you're recently 50?
Gary Vaynerchuk
Yes.
Podcast Host
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, which I know, you know is not easy.
Gary Vaynerchuk
No.
Podcast Host
You know, you're just in the hustle.
Gary Vaynerchuk
Yes.
Podcast Host
But there are moments where you reflect and you look back and I Had some of those opportunities more recently. 1 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.
Podcast Host
Well, you're a parent. Hold on. You're a parent.
Gary Vaynerchuk
Go ahead.
Podcast Host
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 kid to have to survive revolution, you know, lose their father, blah, blah, blah, in order to be resilient. And I worry about their resilience because that's a hard thing to pack. Right. Because it was a circumstance.
Gary Vaynerchuk
You can't fake it. That's right.
Podcast Host
Right. So do you worry about that for your own kids?
Gary Vaynerchuk
Couple things. My no was not that I'm not reflective. My no was I've been reflective my whole life.
Podcast Host
Ah, interesting.
Gary Vaynerchuk
It was a different no.
Podcast Host
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 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 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 and all these things has a lot to do with historical pattern recognition. I lack fear.
Podcast Host
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. 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.
Podcast Host
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.
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. 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 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.
Podcast Host
Is that really true?
Gary Vaynerchuk
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.
Podcast Host
No, 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.
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.
Podcast Host
It's the only constant. It's the only.
Gary Vaynerchuk
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 2700 employees. You know, like, I. I actually associate with the CEO. If we're talking corporate, I actually associate internally with the CEO. Part of myself, maybe more than anything.
Podcast Host
What does that mean? I'm an operator. What's associating with the CEO means?
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 if. 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.
Podcast Host
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 human nature.
Gary Vaynerchuk
Yes. Most people really struggle with the outside noise.
Podcast Host
Right. 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.
Podcast Host
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
Gary Vaynerchuk
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, 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.
Podcast Host
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, if an ambulance comes,
Gary Vaynerchuk
why would you stop it?
Podcast Host
Right. Okay. Meanwhile, I had a girlfriend visiting, and she was saying to me that sometimes my Hair's 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.
Podcast Host
But the new world of media, which is not, you know, CBS Evening News.
Gary Vaynerchuk
That's right.
Podcast Host
Is very different. And in fact, if you go on a 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.
Podcast Host
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. Cause 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 going to 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.
Podcast Host
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 the 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.
Podcast Host
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 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 no in pretty much every other arena. I did not. Especially from an adolescent standpoint. It was insane to me. It continued used 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 teachers 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. 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 friends, parents, 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. Cause he gets these, oh, bad influence 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 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. I was never scared of a. 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 in 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.
Podcast Host
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. 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.
Podcast Host
Did that end the date?
Gary Vaynerchuk
That ended the upside of the date for sure. And so like, 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.
Podcast Host
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 giving feedback or conflict.
Gary Vaynerchuk
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. Cause as you know, Gary Vee, especially in the ad land, I came out guns a blazing with my candor is my.
Podcast Host
I rewatched your big keynote that led to the book.
Gary Vaynerchuk
Love that. It'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. 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. 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. My mom is also not overly canderous 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 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 from 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 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. 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'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. 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 halves. 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.
Podcast Host
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 because it was really Netflix's thing. It was hot, hot. 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 did learn later, like, that it was really helpful to give people feedback early. But how you give that feedback is everything. I mean, I agree. 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.
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. 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.
Podcast Host
It's a muscle.
Gary Vaynerchuk
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.
Podcast Host
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.
Gary Vaynerchuk
I think there's a lot there. 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. He started the company, but I'm the driver of the business.
Podcast Host
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.
Podcast Host
Do you get a bonus?
Gary Vaynerchuk
You're poking like, sorry, it was an accident. No, no, no. And you know what's so funny? I very much understand my father. No, you get a vacation.
Podcast Host
Sorry, I had to.
Gary Vaynerchuk
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 going to get the business when I'm gone. I'm like, dad, you know, I'm going to 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 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 vaynersports, even though he was running it full time, the equity was different in my favor, even though he was running it and everything we've done subsequently, we. We have.
Podcast Host
And 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, 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.
Podcast Host
So easy.
Gary Vaynerchuk
All of a sudden it's. 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. 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 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. I knew who I was.
Podcast Host
Why were you doing V friends? Cause you really always did wanna 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. 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.
Podcast Host
That's I will say though, as a kid again, right. I have a younger sister, seven years. And there was always that sense. Cause you're the EL of like if something happens, it's on you. So I mean there was the sense of incredible responsibility of an older child as 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 going to 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 that. 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.
Podcast Host
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. 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 want to make sure I'm painting a very clear picture. My dad in his. You know, my dad's a cat.
Podcast Host
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. 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. I just remember how I felt. I'm sure it was lots of encouragement, but my dad and I, 80% of the time, it was wonderful. 20% of the time, there was real contention.
Podcast Host
Hard to leave when you made a choice.
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's the man. Here comes his son.
Podcast Host
Yeah, that had to have been son
Gary Vaynerchuk
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, no interest in talking to him. And they only want to talk to his son and his son's the boss, not him.
Podcast Host
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.
Podcast Host
So you had no, like, sense of guilt?
Gary Vaynerchuk
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 in 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. Oh, I like that for you. You know, that was. Oh, that was. I mean, when my dad asked me
Podcast Host
to help, that had to have been so difficult for him.
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.
Podcast Host
Yeah, I know a lot of those
Gary Vaynerchuk
people who would have just 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.
Podcast Host
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.
Podcast Host
Pickleball veefriends.
Gary Vaynerchuk
Yes.
Podcast Host
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.
Gary Vaynerchuk
You're right.
Podcast Host
How do you think about that?
Gary Vaynerchuk
Easily.
Podcast Host
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 a private club. A private club called VCR and Fly Fish Club. Downstairs, I have seven to 10 alternative sports investments. Pickleball, wiffle ball, unrivaled, the women's basketball league, the sailing league. I'm really deep in alternative sports. I have a 2,500 person vaynermedia that people know. Veefriends, people are starting to get known more and more. I still quietly run the wine business through my best and we do wine text. I have a lot going on. Let me tell you why. The answer is easily okay. 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.
Podcast Host
Okay, say more because I want to hear about that.
Gary Vaynerchuk
Do I believe that if I spent every minute on Vayner X or Vayner Sports or Veefriends 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. It the fact that I can step outside for a second after that and go play here, go play there, that is my joy. That's what I want to do. So I don't struggle with prioritizing.
Podcast Host
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 convo. 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. 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.
Podcast Host
Okay, so for people listening who are like, I don't. I. I'm not in touch with my body. What are you saying?
Gary Vaynerchuk
Yes.
Podcast Host
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 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 down this path for a second.
Podcast Host
Okay.
Gary Vaynerchuk
I believe forgiveness is the answer to the quiz that many people are struggling with right now.
Podcast Host
What does that mean?
Gary Vaynerchuk
I believe the dogs can sense I'm going somewhere big.
Podcast Host
I think they can feel, man. You know, it's New York.
Gary Vaynerchuk
But I think it was more that they, you know, they have a different sense. I think they know where I'm going.
Podcast Host
The dogs are like, what's happening here?
Gary Vaynerchuk
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.
Podcast Host
Sorry. Is forgiveness let it be or let it go? Or is forgiveness a combination of candor, like actually saying your piece?
Gary Vaynerchuk
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.
Podcast Host
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? Have you monetized it? Like, 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. That we're not three volunteers trying to, you know, band aid it together. But the goal wasn't money.
Gary Vaynerchuk
Right.
Podcast Host
And it's very confusing to people, not to me.
Gary Vaynerchuk
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 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.
Podcast Host
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.
Gary Vaynerchuk
I had something very good happen, which was I never even knew of a concept of not living within your means.
Podcast Host
Yeah. I never believed in borrowing money or credit card debt. So I relate to that.
Gary Vaynerchuk
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 10 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?
Podcast Host
Okay, so now I want to go to some of the predictions you've made. Hold on, I spilled on myself. It's a good thing. It's called the messy parts. It gives a lot of room.
Gary Vaynerchuk
It's all encompassing for things.
Podcast Host
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?
Gary Vaynerchuk
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 that 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 we'll 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'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.
Podcast Host
It's not that I blame technology because I don't.
Gary Vaynerchuk
I'm not saying you do.
Podcast Host
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 nextdoor, Facebook or Instagram.
Gary Vaynerchuk
Of course.
Podcast Host
In fact, we do storytelling. The way 50 tables have happened around the country is because people have posted stories.
Gary Vaynerchuk
And so let's break that down.
Podcast Host
Okay.
Gary Vaynerchuk
And then someone's on the other side and sees that and they decide if they're going to go outside.
Podcast Host
Yeah. Or decides to host their own table, by the way, which is what's happened.
Gary Vaynerchuk
Correct.
Podcast Host
So for me, technology is an enabler.
Gary Vaynerchuk
It's the exposure.
Podcast Host
Right? Okay.
Gary Vaynerchuk
It's the great exposure.
Podcast Host
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 would know. I was in my home wondering where everybody was reading a book.
Gary Vaynerchuk
It's not true.
Podcast Host
How would I have known?
Gary Vaynerchuk
Cause I just. I love you with all my heart. I think you knew.
Podcast Host
I didn't. I mean, I had.
Gary Vaynerchuk
You might have not known. A play date. But a birthday party. Yes.
Podcast Host
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 of part 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, 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.
Podcast Host
Yeah.
Gary Vaynerchuk
Like I'm not, I'm not pointing fingers. I'm talking about things in the general.
Podcast Host
But I go back to. You have teenagers, actually. 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. 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. I'm like, kenny didn't do that.
Podcast Host
You set up one of your rules. No complaining.
Gary Vaynerchuk
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? If anything, I hope I say it's all about gray. 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? Like, we all worked on farms. The tractors 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.
Podcast Host
I'm gonna agree with you, which I know is shocking.
Gary Vaynerchuk
No, I. Not. Not from the way I view you. I actually think we see things similar.
Podcast Host
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 yet I feel like people are just so convicted about their beliefs in ways that I really can't relate to.
Gary Vaynerchuk
My thing about practical optimism, which is what I think I'm spewing, by the
Podcast Host
way, if you hear noise, it's the dogs.
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. 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 Are you doing? Are you going to work tomorrow? This literally, when I went with my chest, I'm like, are you going to work tomorrow? Yeah. I'm like, the. Are you doing now? You just told me in 10 years, it's all over, dad. 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 grownup and you can do action, actions to mitigate the pain you're feeling. What age do you think that is?
Podcast Host
That happened to me when I was young.
Gary Vaynerchuk
I get it. I'm not asking you or me.
Podcast Host
I think in society, I actually think you have to do that at any age.
Gary Vaynerchuk
I agree.
Podcast Host
And I'm think of forgiveness.
Gary Vaynerchuk
What age do you think?
Podcast Host
21.
Gary Vaynerchuk
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.
Podcast Host
Oh, that's when you're.
Gary Vaynerchuk
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 in sloppy.
Podcast Host
All right. We're not going to be slopping and slop here. Okay? We're. I'm going to go to. Don't you worry. Rapid fire.
Gary Vaynerchuk
Rapid fire.
Podcast Host
Okay. Biggest miss 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. Fuck. And that $50,000 check would have been $540 million so that one didn't work out hard one.
Podcast Host
Okay, one piece of advice you now think was wrong.
Gary Vaynerchuk
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.
Podcast Host
It can be hard. One sentence your mom would say about
Gary Vaynerchuk
you, 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.
Podcast Host
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.
Podcast Host
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 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.
Podcast Host
If you're going to try to 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. Be self aware of what medium you like and then understand that volume of content is not subjective, but the quality is.
Podcast Host
What does that mean?
Gary Vaynerchuk
It means that people do not understand how important volume is.
Podcast Host
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. 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.
Podcast Host
You've told the story about your mom and the jets jersey. I know you still want to own the Jets. Yes, we know. We're going to pray for you. She knitted you a Jets jersey and I know you prized that.
Gary Vaynerchuk
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. I'm infatuated with football. I would argue that football, American football, was my coming to America, my Americanization moment.
Podcast Host
Mine was 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's 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.
Podcast Host
And did you wear it or did you not 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.
Podcast Host
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 to tell me otherwise. And that's my life.
Podcast Host
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 Vee. 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.
The Messy Parts: Fully Clogged - Gary Vee on Forgiveness, Living Fearlessly, and the Reality of AI
Host: Maryam Banikarim
Guest: Gary Vaynerchuk (“Gary Vee”)
Date: March 2, 2026
In this engaging and vulnerable conversation, Maryam Banikarim sits down with Gary Vaynerchuk—entrepreneur, author, influencer, and CEO—to dive into “the messy parts” of life and business. Together, they dissect the contradictions of ambition and kindness, the undervalued power of forgiveness, the reality of self-esteem and insecurity, and the evolving landscape of AI and career pivots. Gary shares personal stories of immigration, family, business, and self-discovery, offering listeners both tactical advice and thought-provoking insights on growth, resilience, and being unafraid of “messiness” in work and life.
| Segment | Timestamp | |---------------------------------------------------|-----------| | Forgiveness’s Importance | 00:00 – 00:24, 33:36, 34:08 | | Gary on Contradictions, Kindness, Winning | 02:09 – 04:29 | | Immigrant Childhood, Early/Delayed Adulthood | 04:58 – 06:53 | | Reflection, Resilience, Fearlessness | 07:25 – 09:27 | | Pattern Recognition, Embracing Change | 09:01 – 12:19 | | Imperfection & Reality in New Media | 13:19 – 14:25 | | Self-Esteem, Childhood, Empathy | 14:25 – 18:07 | | Candor, Feedback, Kindness in Management | 18:17 – 22:32 | | Working with Family, Guilt, Relationships | 22:44 – 29:20 | | Curiosity and Juggling Multiple Projects | 30:06 – 33:10 | | AI, Disruption & Technological Change | 12:47, 41:28 | | Technology & Loneliness | 38:04 – 40:16 | | Parenting, Self-Esteem, and Gray Areas | 41:05 – 42:29 | | Forgiveness vs. Blame, Growing Up | 44:00 – 44:50 | | Rapid Fire (Regrets, Missed Opportunities, etc) | 44:57 – end |
A wide-ranging, characteristically “messy” conversation: Gary Vaynerchuk embodies sharp contradictions—tough, competitive, wildly kind, and driven by joy over dollars. He advocates for radical forgiveness, fearless change, authenticity, and unorthodox success metrics. The episode is a reminder that “the messy parts” are precisely where growth, connection, and genuine leadership emerge.
Memorable Sign-Off:
“My mom said I was the best, and I believed her. And there was nobody outside the door that was going to tell me otherwise. And that's my life.” — Gary [48:39]