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Gary Vaynerchuk
Never said this publicly, so it's fun to give you the exclusive. Gary, you ready? I don't know if you're seeing my goosebumps here. Regret is the great thing we should fear. And if you do not chase your dream or you jump into the water, if you don't go for it all because you're scared what your spouse, your siblings, your parents, your neighbors, your friends, or worst of all, a random person on the Internet that leaves a comment on the post. Think about you. You will wake up at 70, 80, 90, 100 and you will regret the way you lived your only life. We have this little sliver and to not squeeze this little orange of life for every ounce of juice that it has is devastating to me. I was scared to ride a bike. I was scared to kiss a girl. I was scared a lot. But I then jumped and I wasn't scared. What they're doing now to protect themselves from the micro hurt of judgment is going to be super trumped by the macro hurt of regret in their later years.
Jamie Kern Lima
So good. That is so good. You have two kids. Do you want more kids?
Gary Vaynerchuk
This is the first time I've ever told this story.
Jamie Kern Lima
Success leaves clues. And when people betray you or hurt you or go against you or. But you don't let that take up your capacity by staying in a place of resentment, you quickly go to how could I have helped them? You go to a place of love. It's fascinating. I just am imagining how much of your capacity is freed up to your point.
Gary Vaynerchuk
Wow, what an observation. I believe the reason I can do 9 million things and I do 9 million things is that I do not have the ability to dwell.
Jamie Kern Lima
If you've ever felt uncertain about the future with AI, social media and the rapid pace of digital growth, if you've ever wondered, will I even have a job in a few years? Will AI replace us all? Does college still matter? What should I tell my partner, my friends, my kids or grandkids to do so that they have a bright future future? If you have these questions, then today's episode is for you. My guest is known by millions as someone who predicts what's next and can tell us exactly what he thinks we should do to put our lives and our future in perspective Today. Gary Vaynerchuk, known as Gary V, is someone who's not only built billion dollar businesses, he shaped the way so many understand branding, marketing, entrepreneurship and getting attention online in big ways.
Gary Vaynerchuk
I can lose every dollar I have. I could be universally disliked by the public, literally not crippled at all by that I have this. In fact, I have almost like a weird dark fantasy of like, I was very aware very early on that I was different. I knew fairly early on that people like me. But it's funny and here's a big sentence. It's because I knew I liked them first. I believe the way I encounter for the first time a stranger, what I feel in my heart and soul is a deeper energy of love than most people when they encounter their relatives.
Jamie Kern Lima
They like your eyes started tearing up. Your eyes just started tearing up right now. You got goosebumps all up and down.
Gary Vaynerchuk
My father is incredibly honorable. Incredibly. Word is bond. My dad thinks a slight embellishment, James is like the great lie of a lifetime. So when I started working in my dad's liquor store at 14, he scared the shit out of me on that. This means I'm saying something that's the most honest thing I could say. And my goosebumps go. That's how real it is.
Jamie Kern Lima
Gary is a serial entrepreneur and serves as the chairman of VaynerX, the CEO of VaynerMedia, and the CEO and creator of the entertainment and collectibles company the Friends. Gary is considered one of the leading global minds on what's next in culture, business and the Internet. He was an early investor in companies like Facebook, Twitter, Tumblr, Venmo, Snapchat, Coinbase and Uber. He's a six time New York Times best selling author and documents his daily life as a CEO through his social media channels which have more than 45 million followers. His podcast, the Gary Vee Audio Experience ranks amongst the top podcasts globally. He's a newlywed to his wife Mona, a dad of two and he's the person millions of people look to daily. And he's taken time out of his busy schedule. He's flown here. He's in person on the podcast just for you today. From advice on mindset and how to succeed on social media with AI in entrepreneurship and how to know exactly what's coming next and what to do about it in a world of technology and AI that's changing by the second. I am so excited for this conversation and whether today you're listening for yourself or because someone that you love shared this episode with you, I want to welcome you to the Jamie Kern Lima Show Podcast family. Thank you so much for being here. And can you take two seconds right now and just hit the subscribe or follow button on the app that you're listening or watching on? Thank you so much. It truly means so much to Me. You can also get your inspiration into your inbox from me for free. You can join my newsletter community@jamiekernlima.com Also, this incredible podcast episode today, it's not just for you and me. Please share this with every single person you know who might need some inspiration today or perhaps a boost in their self belief. Because what you can hear today can truly impact mine, yours and their lives too.
Gary Vaynerchuk
Welcome to the Jamie Kern Lima Show.
Jamie Kern Lima
Oprah, how have you defied the odds?
Gary Vaynerchuk
Her show is unlike any I've ever done. A revelation. When you listen, it feels like a hug. But your brain and your spirit and your heart is like, wow.
Jamie Kern Lima
Melinda French.
Gary Vaynerchuk
When I look into Jamie's eyes, I feel like I am on some other cosmic level with her. I could see the light around her. She's infused with light.
Jamie Kern Lima
Imagine overcoming self doubt. Learning to believe in yourself and trust yourself and know you are enough. Welcome to the Jamie Kern Lima show.
Gary Vaynerchuk
Jamie Kern Lima is her name. Everybody needs Jamie Kern Lima in their life. Jamie Kern Lima. Jamie, you're so inspiring. Jamie Kern Lima.
Jamie Kern Lima
Gary Vee. Welcome to the Jamie Kern Lima Show.
Gary Vaynerchuk
Jaime, thank you so much. That's such a sweet intro. I'm really, really genuinely excited to be here.
Jamie Kern Lima
I'm so excited you're here. First time on the show.
Gary Vaynerchuk
Yes. Thank you for having me. Really.
Jamie Kern Lima
First time on the show.
Gary Vaynerchuk
Congrats about the show. It's really exciting to be here. Thank you.
Jamie Kern Lima
I want to just right off the top ask you this because so many people are impacted by this. They're afraid to start or to make a change or to go after a dream because they're afraid of judgment or rejection or they're sort of like frozen by fear of what other people might think.
Gary Vaynerchuk
That's right.
Jamie Kern Lima
What do you say to them?
Gary Vaynerchuk
That it's the greatest pandemic in our society. You know, we've created this. I don't know if you've heard this term, imposter syndrome.
Jamie Kern Lima
Yes.
Gary Vaynerchuk
This is fun to say to you. It is makeup for the word insecure. The world is insecure, period. You know, this has been a great epiphany of my life. I was so mothered properly. I really genuinely. And for the people that follow me, that are listening right now, that know me, they know how often I reference my parents and specifically my mother. I was parented so uncomfortably. Well. The greatest book I'll write. And even though I've written all these books and have done well, I've been working slowly but surely because I want to give it more time. On a book called Perfectly Parented. Parented. And it's obviously, of course I wasn't perfectly parented. There's no such thing. Or is there such a thing? That's all judgment. But it gets to the crux of your question. The world is insecure. I'm devastated by it. It has driven my personal brand's content, in hindsight, my whole career. And what I say is one of my great fascinations in society is that I think we've over glamorized youth and we've dramatically undervalued wisdom and the elderly in the last 40 years. There's been a huge shift for the history of time. I'm talking cave men and women. The elder was put on a pedestal and that was all the way until recent times. And as you know, because of technology, we're more likely to make fun of our grandmother for not knowing how to use TikTok than we are to sit next to her and extract her wisdom. And we now overvalue 20 year olds for their knowledge of technology or fashion or what's cool. And that's okay. I love that I sit here with a ball cap. I'm 49 years old. I love being youthful. There's a lot of beauty in the fact that our society has become more youthful. I love that the golden girls looked one way and the Sex and the City girls looked the different way. There's a lot of greatness to that, but there's also consequences. And I feel like we as a society have dramatically underestimated the elder wisdom. And I implore everyone here to spend more time with a 70, 80 and 90 year old that is not a relative because it will be highly valuable to their life. And that little rant about the elderly gets me to my point, which is we have gotten to a place where we have things out of whack. And if you speak to a 90 year old that is not your grandfather or grandmother, what I promise you, Jamie, you will see is that regret is the great thing we should fear. And if you do not chase your dream or you jump into the water, if you don't go for it all because you're scared what your spouse, your siblings, your parents, your neighbors, your friends, or worst of all, a random person on the Internet that leaves a comment on the post, think about you. You will wake up at 70, 80, 90, 100 and you will regret the way you lived your only life. I don't know if you know this, Jame. We were not you and I and everybody listening. We were not born for a very long time in the history of the world. And we will be dead and we will be dead forever. So we have this little sliver. And to not squeeze this little orange of life for every ounce of juice that it has is devastating to me based on the fact that your parenting, your DNA and your environment led to you valuing someone else's opinion greater than your own opinion about what you want to do. And so I continue. What do I say? I say I'm searching every day of my life for the words that may make one person on the other side of this podcast finally jump. Maybe that little rant did it. But at the end of the day, whatever takes. Therapy, exercise, reading, hanging out with different friends, cutting out negative people, cold plunges, massages, hiking, like whatever it takes to get you to jump. And I will say this, and this should be very encouraging. Everyone listening here was scared of doing things in her adolescence. I was scared to kiss a girl. I was scared. In fact I was a real scaredy cat, which is wild. I was scared to swim. I swam when I was 9, late and by the way, on the record, the only reason I swam is cause my sister started swimming and there was no way I was gonna have my six year old sister start swimming before me. So I jumped directly in the pool the second I saw her swimming. And I'm like, we swam at the same. I couldn't fathom that she started. I was scared to ride a bike. I didn't want to skin my knee, I didn't want to hurt my elbow. I was scared to kiss a girl. I was scared a lot. But I then jumped and I wasn't scared. And I really believe someone here, quitting a job, breaking up with a bad boyfriend, starting to make content on TikTok. The thing I'm wildly passionate about these days. We'll get into it later, I'm sure. Live social shopping, which is super cool to say in front of you given that you're the queen of that format in a different way. I just want people to jump because they're going to regret, Jamie. They're going to regret the negative of like what they're doing now to protect themselves from the micro hurt of judgment is going to be super trumped by the macro hurt of regret in their later years.
Jamie Kern Lima
That's so good. That is so good. And I think for a lot of people it's hard in the moment or it feels overwhelming. Are you scared of anything right now?
Gary Vaynerchuk
Only the health and wellness of my inner circle of family and friends. The only thing I'm scared of, I can lose every dollar I have. I could be universally disliked by the public, literally. I'm not crippled at all by that. I have this. In fact, I have almost like a weird dark fantasy of like, going back to zero. Like, in fact, it's really weird. I have to really work through it, you know, Like, I'm that not scared of it, that I'm almost like weirdly fantasize and romanticize about going back to the humble beginnings.
Jamie Kern Lima
Is it because you want to, like, the victory of building it again? I think so.
Gary Vaynerchuk
I think.
Jamie Kern Lima
Or you want none of the pressure that comes with.
Gary Vaynerchuk
No, the pressure I love.
Jamie Kern Lima
Okay.
Gary Vaynerchuk
Like, it's why I'm so out there, right?
Jamie Kern Lima
Yeah.
Gary Vaynerchuk
Gary Vee, me, I've been one of the most consistent public figures of the last 20 years, at least on the Internet. The pressure? No, because in fact, I don't feel the pressure. I live with the rant I just made. I do not value other. I do not value my mother's opinion about me. She is my number one North Star. So why am I gonna value some random listener to this podcast?
Jamie Kern Lima
How did you get to this place?
Gary Vaynerchuk
Cause she built me. It had the DNA. She has that DNA. Like, I do believe that I was. I do believe some people are born with some level of a confidence, genetic versus not. I believe that to be true. However, I've watched friends and people around me go from shy or insecure to dramatically more confident. I've seen it. So I think you can build it. So, A, I think I was predisposed a little bit. B, I'm telling you, my mother is a master class. I'm telling you. J. She made me feel remarkable about myself. Self esteem for days. But she didn't create delusion or entitlement. She grounded me. She kept me accountable. So I didn't. She like balanced. She was purple in a world of red and blue. Right. And then finally, environment. I was born in the Soviet Union. I immigrated here when I was three. We were uncomfortably poor. I lived most of my childhood as lower middle class to somewhat to middle. Even when we got to middle class, my mom acted like we were lower middle class or borderline poor, meaning they never bought me anything like toys. I remember I got like three toys for one holiday season. And I thought it was like. I mean, I can't even explain to you what I thought it was like. It was the year before my brother was born and me and my sister. I think my mom was overcompensating that holiday Season. And like, I literally was like getting six different toys. Three different toys instead of one was like, I can't even explain it to you. Whereas, like, you know, where some people, like, max out their credit card to give their kids 40 toys. And I understand why, but I think. I think environment. I grew up in Jersey in the 80s. You know, it was, you go outside, your parents are not helicoptering you, you get into fights, you skin your knee, it's rugged out. Especially 80s jersey, lower middle class. Like, I got into fights. I learned to be respectful. Cause if you disrespected somebody, you might get punched in the face. Like a lot of things we don't grow up with nowadays behind our computer screens. Everybody's a tough guy on Twitter, right? You know, in 1980, Twitter was the cafeteria. And if you said something wrong, it happened, right? And so, you know, I think the combination of environment, nature, nurture, and here I am. And in fact, my confidence, I don't think belongs to me. Like Gary Vee me, all the accolades I get, I think that's an indication of my parents, the American dream and Jersey. I think Vee friends, my businesses, I feel a little bit more of me, you know, But I think one of the reasons I'm so detached from my personal brand and my awareness, slash, fame, whatever you want to call it, or my financial success, is I kind of feel like I'm the byproduct of them. Not necessarily I'm me, if that makes sense.
Jamie Kern Lima
Also, you know, there are, as you know, hundreds of millions of people online, a lot of people putting content out there, speaking their soul, doing all the things, even showing up authentically. And very few people are able to communicate a thought or an idea in a way that just like people can relate to, stops people, but also that people just connect to, that they instantly foster trust with, that they want to watch. Do you, you being one of the best communicators in the world, indisputable by numbers, not an opinion. Indisputable by numbers and by impact. And by the number of people that repost your content, the number of people that are on your pages. Have you. Do you feel that you have a calling or like an anointing that was predetermined on your life to be an impactful communicator? Is it something you studied obsessively with? Because it's different than, I'm guessing, all the people you were raised around, all the people that you give credit to so much for?
Gary Vaynerchuk
I believe that I did not grow up thinking anyone on Earth would know me. You know, I made my first piece of content when I was 30 years old. And it was a wine video that I was trying to use to build up my wine business. And it wasn't until 34 that I started to make the kind of content that I'm now known for. So I didn't, you know, I didn't know who Tony Robbins was. I didn't know, like, I didn't know that Game of Personalities or I didn't know what a motivational speech was. So I didn't study anything. I didn't know anything on the other side. I think that I was very aware very early on that I was different, that I could say. I remember consciously deciding school didn't mean anything in fourth grade in 1986, when not going to college meant you were the lowest of low. And I had the confidence to follow my calling, which at the time I called being a businessman. It's now known as entrepreneurship. Right. I knew that I was. I didn't know the word charismatic, but I, you know, I was the president of our school in fifth grade. And even before that, I knew that humans gravitated towards me. Every kid in my neighborhood, even their parents. I didn't know what charisma was. I didn't know what being dynamic was. But I knew fairly early on that people like me. But it's funny, and here's a big sentence. It's cause I knew I liked them first. It's really wild how much I love people, and I mean the general public. I wish everyone on this podcast could see in like visuals with words or diagrams or colors how I feel when I'm walking through an airport. Look, I wish people knew how I feel about your two guys right now behind the camera. I'm being dead serious when I said, hey, guys to them. I wish. I don't know if you're seeing my goosebumps here.
Jamie Kern Lima
I do.
Gary Vaynerchuk
I wish people knew how I felt when I encounter a stranger. I believe what I'm about to say. I've never said this publicly, so it's fun. To give you the exclusive.
Jamie Kern Lima
We need to pause for a super brief break. While we do take a moment and share this episode with every single person that you know who this could inspire. Because this conversation can truly be the words and inspiration that they need to hear today to keep going, to remember they matter. To feel less, less alone. More enough, more connected and more worthy in life. You don't soar to the level of your hopes and dreams. You stay stuck at the level of your self worth. When you build your self worth, you change your entire life. And that's exactly why I wrote my new book Worthy how to believe you are enough and transform your life for you. If you have some self doubt to destroy and a destiny to fulfill, Worthy is for you. In Worthy, you'll learn proven tools and simple steps that bring life changing results like how to get unstuck from the things holding you back, build unshakable self love, unlearn the lies that lead to self doubt and embrace the truths that wake up worthiness, overcome limiting beliefs and imposter syndrome, achieve your hopes and dreams by believing you are worthy of them and so much more. Are you ready to unleash your greatness and step into the person you were born to be? Imagine a life with zero self doubt and unshakable self worth. Get your copy of Worthy plus some amazing thank you bonus gifts for you@worthybook.com or the link in the show notes below. Imagine what you do if you fully believed in you, it's time to find out. With Worthy, who you spend time around is so important as energy is contagious and so is self belief. And I'd love to hang out with you even more, especially if you could use an extra dose of inspiration. Which is exactly why I've created my free weekly newsletter that's also a love letter to you delivered straight to your inbox each and every Tuesday morning from me. If you haven't signed up to make sure that you get it each week, just go to jamiekernlima.com to make sure you're on the list and you'll get your one on one with Jamie weekly newsletter and get ready to believe in you. If you're tired of hearing the bad news every single day and need some inspiration, some tips, tools, joy and love hitting your inbox. I'm your girl. Subscribe@jamiekernlima.com or in the link in the show notes do you struggle with negative self talk? Living with a constant mental narrative that you're not good enough is exhausting. I know because I spent most of my life in that habit. The words you say to yourself about yourself are so powerful and when you learn to take control over your self talk, it's life changing and I wanted to give you a free resource that I created for you if this is something that could benefit your Life. It's called 5 Ways to Overcome Negative Self Talk and Build self love and it's a free how to guide to overcome that negative self talk to Build confidence and develop unshakable self love so that you can dream big and keep going in the pursuit of your goals. Don't let self sabotaging thoughts hinder your progress any longer. It's time to rewrite the script of your life, one filled with self love, resilience and unwavering belief. If you're ready to take charge of your narrative, build unwavering confidence and empower yourself to persevere on the path to your dreams. You can grab your free guide to Stop overthinking and learn to Trust yourself at jamiekernlima.com resources or click the link in the show notes below. And now more of this incredible conversation together.
Gary Vaynerchuk
It's really wild how much I love people, and I mean the general public. I wish everyone on this podcast could see in like visuals with words or diagrams or colors how I feel when I'm walking through an airport. Look, I wish people knew how I feel about your two guys right now behind the camera. I'm being dead serious when I said hey guys to them. I wish I don't know if you're seeing my goosebumps here. I wish people knew how I felt when I encounter a stranger. I believe what I'm about to say. I've never said this publicly, so it's fun to give you the exclusive. I I believe the way I encounter for the first time a stranger. What I feel in my heart and soul is a deeper energy of love than most people when they encounter their relatives they like. So I think I always knew that. And then I think the serendipity of how the world worked. I'll give you an example. If I was 30 years older, I would have never been known because I would have never left my family in New Jersey to go to Hollywood to be found. The Internet just happened to come along at the right time. The maturity of the Internet to be in the social media era came at the right time and I just happened to be at the right place and I understood what was happening and I had the you know, I believe that many people build audiences for many reasons. I believe I've built the audience I've built because I think I out love my community, my audience in comparison to almost anybody else producing content in the world. I really believe that. And I don't think I'm better than and I'm sure there's others that feel exactly the way I do towards strangers and acquaintances. But I'm in the fucking mix. At the top of I've never made a piece of content where my brain did not go into what's in it for them. I believe one of the reasons most of the people listening right now do not build the audience they're hoping to build is they spend all of their time thinking about, is this gonna get me likes? Is this gonna get me followers? Is this gonna get me money when I make content? I mean, we talked before camera. You're like, I'm like, I wanna be on this show. Cause I know I'm the right voice for three of the people on this podcast listening right now that have never heard of me. I always think about them. I then know, listen, I'm not some saint or angel. I'm aware that if I'm bringing value, that may lead to opportunity for me and the things that I want for myself emotionally, financially. But I only know how to start with what's in it for them. In fact, I'm at a point in my life where I'm trying to be more balanced of selfish and selfless behavior because I think I go into superhero syndrome too much. And that's something I'm thinking through in my life, professionally, personally, and just in general, but never with my audience. I think. I think I've got the right framework.
Jamie Kern Lima
When you said if people understood what you were thinking and how much love you have, when you meet a stranger, your eyes started tearing up. Your eyes just started tearing up right now. You got goosebumps all up and down. Where do you think that comes from?
Gary Vaynerchuk
Just a very fortunate. Back to the earlier question. I genuinely think I was genetically predisposed for it. And then I think I was molded by it. I view as though I was the really remarkable ingredients of love. And then I had the best chef cook me. I think between who I was and the mother I had, I think I was the best. I think that's the best analogy I can use. I think four loving strangers. I think I was all the perfect ingredients. The best carrots, the best meat, the best chicken, the best sauce. And then I had the best chef in the world cook my ingredients. And then here I am.
Jamie Kern Lima
You talk about your dream of wanting to buy the jets and your mom's role in that. Can you share?
Gary Vaynerchuk
Yeah, I think you know everyone. This is pretty deep. There's a very detailed video at the top of my Instagram. It's Gary V E E. If you want to get a little more color on this, very simply back to selfish wants. I have this great dream. Always have had it since fourth or fifth grade. Around the time I decided school didn't matter that I would. That was probably also the time I realized I couldn't play for the Jets. I was pretty good. I have very good hand eye coordination. So in first, second, third grade, I was a really good athlete and better than all the kids in school and baseball and things of that nature. And then around 4th and 5th and 6th grade, I was like, wait a minute, what's this strength, speed and athleticism part? And I was like, oh, I'm not going to be a football player. And I probably at that point I was already doing very well with lemonade stands and shoveling snow. And then by sixth grade, I was making a lot of money selling trading cards and I kind of pivoted to, okay, I can't play for the Jets. I'm going to own the Jets. And so I had this great dream and that's always been there. And then the part that you're referencing, when I was 7 and fell in love with the Jets, a lot of the boys in the neighborhood had a Jets jersey and I wanted one. And I asked my mom, can I get a Jets jersey? Cause we played a lot of backyard football and everybody had a Jets jersey and I had a T shirt and I wanted to be in the mix. And I love the jets now and I want a Jets jersey. Well, for all the immigrants listening, when you're a couple years into America and you're not very. You have really no money. Buying a $20 at the time, jets jersey was not in the cards. You know, everything was for food and shelter, even clothes. Like, my dad worked at a liquor store and like, I literally wore liquor T shirts my whole life. You know, like, we did not buy clothes, at least T shirts. And so at night for the next several weeks, because my mom was an immigrant, mom cooked, cleaned, like, waited for her husband to come home at 10:00pm Cook for him. Like, her day was 7:00am to midnight. Cook, clean parent. Cook, clean parent. Like, real hard work. And then after all that, at night she would. She knitted me a Jet sweater. I don't know if you know this, if you've seen my content. I put up the number five a lot. I do this a lot. And the reason I do that is that Jet jersey that she needed me had the number five on it because already it was my favorite number. And when I knew seven or 10 years ago, I'm like, oh man, I'm going to take a lot of pictures for the rest of my life. Like, I kind of tipped where I knew I was going to be known. And I Knew we were in the pictures era with phones. And I remember thinking, like, huh, I'm going to probably take millions of photos for the rest of my life with people. I'm like, I want it to be meaningful. And I started to throw up the five as a little head nod to my mom, you know? And so, yes, she made me that jersey. It had the number five on it. I wore it every day. And now it is in a literally fireproof safety deposit box. So that when I buy the New York Jets, I'm going to hang that jersey. I'm going to build a stadium potentially in Queens. Cause that's where the jets fans want the jets back, even though they're in. It's funny, when we immigrated to America, I lived in Queens for two years. And then we moved to Jersey. And the big thing among jets fans is they play in New Jersey. I don't know if you know this. In MetLife Stadium, where the jets and Giants play, they play in New Jersey, even though they're both New York, but they originally played in Queens. And I always think, like, when I buy them, will I keep them in jerseys since I'm such a Jersey boy, or do I bring them to Queens? Cause a lot of the diehards want that. And when I first came to America, that's where, you know, it's very romantic for me, anyway. The other thing that's romantic to me is when I build my own stadium, I'm gonna put that jets jersey right in the front of the main entrance for everyone to see. And it's gonna have a little plaque and it's gonna say, from not being able to own a $20 jets jersey to eventually owning the entire team, all of you can do it, too. So I think about that a lot.
Jamie Kern Lima
How has your mom responded to that?
Gary Vaynerchuk
You know, I think at this point in my life, it's very clear to me that it is shocking how much I do strictly for the opportunity to make my parents proud. My mom is like my best friend, you know, everything I've accomplished is because of her, 100%. Like, it is so not lost on me. And by the way, before my dad sends me this clip and yells at me and complains, I'm also very fortunate. I think there was a couple pieces that my mom could not instill in me. My dad is much more competitive than my mom. Huge factor in my career and my personality. The other thing, my mom is gift of gab. And so am I, which means a little embellishment, a little, you know, my father is Incredibly honorable. Incredibly. Word is Bond. My dad thinks a slight embellishment, James, is like the great lie of a lifetime. So when I started working in my dad's liquor store at 14, he scared the shit out of me on that. I remember one time I told him I had a big day of selling a wine he wanted me to sell. And on the way home, we were driving and he said, how'd you do with the wine? I was like, dad, I sold 20 cases of the wine. I sold a ton. And then that was Saturday. And then on Monday, when he came back from work, I was in school. I was a kid. When he came back home for dinner that night, he, like, got really mad at me, and he's like, you sold 17.3 cases of that wine and, like, really made it, like a deal. Like, this is a problem. I was like, what are we talking about here? 17, 20, same shit. And over, I would say from 14 to 18, my dad instilled in me honor and truth and sucked out of me embellishment and borderline bullshit. And I believe that that has had a profound impact on who I am and how I'm perceived and who I became as a public figure. I think a lot of people, when they first encounter my energy and my style, are like, wait a minute. I don't know when you first saw. Like, I'm very aware that when you're this hyper, you know, I'm pretty chill right now in this interview by comparison. Like, I'm pretty high energy. I. You know, I'm selling my beliefs. Sometimes I'm selling my collectibles or my wine. You know, I'm empathetic to some people being like, eh, what's up with this guy? And I always think about this. I'm always like, man, you know, a lot of people go on the journey with me of, like, I don't know about this guy, till, like, I really like this guy. And a lot of times I think, like, man, that's all my dad. Because if I wasn't as. Like, if I wasn't as true, and I was the bizarre, you know, the Superman, there's like, Superman, bizarre, Superman. Like the bad. If I was the bad version of Gary Vee that some either start believing or even some people are very cynical, think that I am. I wonder if I could have been that if I didn't have my father in my life, you know, I wonder if, with a different father, if my dad was a shyster. And at 14, I started working for him and I already had all this gift of gab and charisma. What, have I gone down a path of being a shyster instead of something I'm incredibly proud of? Very grateful for my parents.
Jamie Kern Lima
Does it bother you when you sense someone else's embellishing or lying?
Gary Vaynerchuk
Not really. You know, what's you want to. This is gonna be a fun part of the podcast. It's funny how quickly I jumped from, like, answering you, not really to where I want to go with this. Not at all. And let me explain where I'm going. I actually. I actually am incredibly empathetic, sympathetic and compassionate to people that do wrong things. I actually struggle with judgment and anger to things that people do that are really not great, let alone something like a white lie or an. Like, I struggle with judgment. James, when I see someone doing something wrong, like, I'll give you just, like, let me give you a very simple example. Happened yesterday in la. Somebody, like, cut off someone on the street. And I watched someone, like, massively yelling at that. Like, they're just so angry. And I was just thinking about both of them. I was like, both. The person that did the thing, like, where are they coming from on that? Are they impatient? Do they have a problem? Like, what are they doing? And then the person that, like, do you know how many times I've been cut off? I lived in Jersey, like, a million. I would never, like, go crazy and, like, road rage to go there. You're not in a good place overall.
Jamie Kern Lima
Yeah.
Gary Vaynerchuk
So I think in general, in life, when I see someone do something wrong, even, like, bad stuff, my brain goes to, like, what's. How. Why are they hurting? What's going on? And I'm talking about even when people are really bad to me, when people have stolen from me, when people have done very bad things to me, when people that I've helped financially and emotionally do horrible things behind my back, it's crazy how little energy or time I spend on the normal reaction. I default pretty quickly into man. I'm so. A, I'm so grateful that I'm not in that place mentally and emotionally. And B, I hope they'll get better. I hope, you know.
Jamie Kern Lima
Have you had a lot of people betray you?
Gary Vaynerchuk
Sure, yeah. It's life. I'm so out there. I've run businesses my whole life. One of my dear friends in my dad's liquor store that I took from being a kid that, you know, was a high school dropout, I think, or maybe graduated high school, like, basically took from, like, at the time, whatever minimum wages was in Jersey, 9 bucks, 10 bucks an hour to all the way to like the head of our shipping department. Like, a real job that he built his whole family on. Stole hundreds of thousands of dollars of inventory from my dad on finding a very smart kid, like, found a very unique loophole that allowed him to, like, ship things to himself and sell it in the black market. Just like unbelievable layer of betrayal. My dad, actually, I think this is the first time I've ever told this story. Mainly because if my dad listens to this, he's gonna go into a five week depression about it. He's that hurt still and angry. I forgave the kid on the moment we understood. And by the way, years later, I found out, like, he hurt his back and then he started taking back pain medicine. And you know, like, this is where my brain goes. Like, I knew he wouldn't do that in his soul, but a series of events led him to do that. I believe most humans in their soul are not looking to do bad, but things happen. And I think what's happening in our world now is a lot of people are selling fear and hate. And I think a lot of people are not strong enough to see through it. I think a lot of people go down paths they don't need to. And then I also think that people struggle with accountability. When bad things happen to me, I view them as my fault. I don't even view them as betrayal. I view them as like, what could have I seen to not let this happen? And then I quickly go into like. And then maybe it's so crazy this goes back to love. Oh, I could have helped him see it a different way earlier, not, oh, I wish I fired this person earlier so this never happened. Oh, crap. If I knew he was going down this path, I could have stopped him from ever getting to the thing that would have been fireable, which is the.
Jamie Kern Lima
Polar opposite of a victim mentality. I'm just fascinated listening to you share all this because, you know, the idea that success leaves clues and you have this just abundant capacity to do so many things, to give so many, you know, to give so much, to impact so much. And I'm listening and I just want to call this out for everyone listening right now. Because what you're sharing is you don't let things. Even when people betray you or hurt you or go against you or you don't let that take up your capacity by staying in a place of resentment, you quickly go to, how could I have helped them? You go to a place of love. It's fascinating. I just am Imagining how much of your capacity is freed up.
Gary Vaynerchuk
To your point, wow, what an observation. I believe the reason I can do 9 million things and I do 9 million things is that I do not have the ability to dwell. I believe almost everyone listening right now is not winning because they're spending all their time looking backwards. I believe a sentence that starts with I should have is the beginning of a very bad sentence. I love learning from my mistakes. In fact, it's probably one of my great strengths contextualizing everything that's ever happened in my life to make better decisions tomorrow. But to your point, if you want to go down that path, it is. I am confident when I deliver this sentence. My dream about heaven is. It tells you everything. When I get to heaven, one of the 21st things I'm going to do is, during my time on Earth, where did I rank amongst 8 billion people in the ability to not dwell? I'm pretty confident I'm in the top 10,000. I just don't have it in me. Which gets to the biggest point of all. You can't be scared. You do not have fear when you are not scared to lose. I love losing James. It's so crazy how much I like losing. Think about what I said earlier. I dream about losing everything. That's how much I. I mean, again, here it is. This is. By the way, this has been a huge factor in my life. The fact that everything great or everything I'm worried about comes up in goosebumps, like naturally. This is how in tune I am with myself. I always know this means I'm saying something. That's the most honest thing I could say. Literally, I'm talking about losing everything and my goosebumps go. That's how real it is. You think I'm gonna be scared about a micro loss? You think I'm worried about johnnypants49 leaving a comment that you suck? Gary B. You think I'm scared of a business going to zero? You think I'm scared of any? I'm not scared of anything. In a world where I'm willing to lose everything and do it again, it makes you unstoppable.
Jamie Kern Lima
Do you think? You mentioned heaven? Do you believe in heaven?
Gary Vaynerchuk
I do. Predominantly through this dream, I've made up for myself of what heaven is. I literally think heaven is this super AI computer that can tell you everything about your life and you just chill up there and play scenarios. Like, one of the things I can't wait to ask the heaven supercomputer is show me the moment I was Closest to dying besides the time I actually died. And I always think it's this weird thing of, like, had I not forgotten my keys, you know, the butterfly effect. Like, if I had not forgotten my keys or if I didn't meet this person, I would have met this person, and we would have been here, and I would have fell off a cliff or I don't know. Or I would have eaten this banana, and that banana would have triggered a gene in my body. Like, I'm so fascinated about that. I don't know why I would have asked about, like, showing me my alternatives in life. If I didn't move here, if I stayed here, if my dad did this, or if my. I love the what ifs. One of the reasons I'm a successful entrepreneur. You know, it was even weird. Obviously, many people, when they read my intro, talk about the things I invested in. I don't know if it's the energy we're in right now, but it was. I mean, I've heard it 500,000 times, but I was micro reflective for a second. When you were reading that, I'm like, man, I really did invest in those companies before people knew. And I'm like, I think the reason that happened and the reason I'm talking about heaven the way I'm talking about it now is I think my superpower, which is very disguised. And I'm curious. Cause you know enough about me to say I'm curious how this is gonna land on you. I actually think one of my core superpowers is curiosity. I'm inherently curious. You know, I hate. I should have, but I love what is what. I love that. And I think it sends me down. I'll give you an example. Do you know what I use ChatGPT for? What? On the flight out here from New York, I spent an hour and a half prompt engineering questions about why Labubu happened.
Jamie Kern Lima
Mm, I bet you did.
Gary Vaynerchuk
Yeah. You know, with me, with collectibles and pop culture and marketing, like, I'm wildly curious. It helps me see around corners. It makes me a fun dinner date. It makes me a great entrepreneur. I wish more people were into it. And in fact, vee friends and I'm sure we might touch on it. Is really the great extension of me, the person I know that I'm not everyone's cup of tea. I do not believe I can impact all 8 billion people. But I believe my characters. Patient Panda, Ambitious Angel, Curious Crane. You can see where I'm about to go now. If I can make Curious Crane famous, if I Can make, you know, cartoons and comic books. If some of the people listening now when they have grandchildren one day in 30, 40 years, if those kids are wearing Curious Crane pajamas, I can elevate the word curious to the youth, the word patience, the word accountable, which is really missing right now. And that's why I have accountable Aunt Empathy. Empathy Elephant. If I can elevate those words. Cause I can get to people earlier in their journey. Youth. Or it might be a character that I, Gary Vee, am not the right personal brand for someone, but I can get them to get into accountability through the videos or the cartoons of these characters, the hello Kitty of it all, that I can leave a bigger impact. And I think Curious Crane is one of my favorite V friends because it's getting more obvious to me as I get into my middle years era that curiosity is a superpower of mine.
Jamie Kern Lima
You have two kids. Do you want more kids?
Gary Vaynerchuk
Yeah, I'm definitely, you know, look, my great grandmother said I grew up with her. You know, in Russia, in the old country, everybody had kids at 20.
Jamie Kern Lima
Yeah.
Gary Vaynerchuk
She basically used to say this Yiddish word, lost language basically translates to kids are the ultimate happiness in the world. So for sure you do.
Jamie Kern Lima
I haven't shared this yet, but we're expecting our third.
Gary Vaynerchuk
Wow.
Jamie Kern Lima
Yeah, yeah, wow.
Gary Vaynerchuk
Congrats.
Jamie Kern Lima
And I want more. And you know, I'm about to turn, I turned 48 this year. So it's like I agree and I actually love having them later also because I feel like, you know, it's just a different perspective.
Gary Vaynerchuk
You know, I've been fortunate in my business career to spend a lot of time with 70 and 80 year old. Back to thing I was talking about earlier, I'm as likely to hang with an 80 year old business person as I am an 18 year old business person. And I do a lot. In fact, I do a lot of both. I would argue. I spend a lot of time with 18 year old entrepreneurs, about IRL streaming and AI and then 80 year old real estate and like, you know, those kind of characters.
Jamie Kern Lima
Yeah, you know, it's wild. I just this. So I was, I was in Copenhagen last week at a table in a restaurant and there's a couple next to me in their 80s.
Gary Vaynerchuk
Yes.
Jamie Kern Lima
And the guy's phone goes off and he's doing audio prompts to ChatGPT. Yeah, he's in his 80s and I'm like, the whole world is changing so fast. So much to ask you about veefriends, about AI, about social media, about chatgpt, about all of it. About AGI. All of it. This conversation with Gary Vee is so incredible. We made it into more than one part. And if you've ever felt uncertain about the future with AI, social media and the rapid pace of digital growth, if you've wondered, will I even have a job in a few years? Will AI replace all of us? Does college still matter? What should I tell my partner, my friends, my kids or grandkids to do so that they have a bright future? If you have these questions, you are not going to want to miss this incredible Part two of our conversation with Gary Vaynerchuk. Coming up in the next episode of the Jamie Kern Lima Show. Remember, this episode's not just for you and me. Please share Share it with every single person that you know because it can truly impact and change their life too. And if you love today's episode, please click on the Follow or Subscribe button for the show on the app you're listening to it on or watching it on. And if it added value to your life, if you could please give it a rating or review five stars, it would be amazing. I would be so grateful. And then share it. Share the episode with everyone you believe in. Maybe share it with another person whose life you know could benefit from it. Share it with someone you know who's maybe making a change in their career or fearful of what's happening with AI and all the technology around us and what exactly they should do. Share it with others online or in your community who just might need the words and tools and lessons in this episode today. You never know whose life you're meant to change today by sharing this episode. And thank you so much for joining me today. Before you go, I want to share some words with you that could, couldn't be more true. You right now, exactly as you are, are enough and fully worthy. You're worthy of your greatest hopes, of your wildest dreams, and of all the unconditional love in the world. And it's an honor to welcome you to each and every episode of the Jamie Kern Lima show here. I hope you'll come as you are and heal where you need, blossom what you choose, journey toward your calling and stay as long as you'd like. Because you belong here. You are worthy. You are loved. You are love and I love you. And I cannot wait to join you on the next episode of the Jamie Kern Lima Show. In life, you don't soar to the level of your hopes and dreams. You stay stuck at the level of your self worth. When you build your self worth you change your entire life. And that's exactly why I wrote my new book how to believe you are enough and transform your life for you. If you have some self doubt to destroy and a destiny to fulfill, Worthy is for you. In Worthy you'll learn proven tools and simple steps that bring life changing results like how to get unstuck from the things holding you back, build unshakable self love, unlearn the lies that lead to self doubt and embrace the truths that wake up worthiness, overcome limiting beliefs and imposter syndrome, achieve your hopes and dreams by believing you are worthy of them and so much more. Are you ready to unleash your greatness and step into the person you were born to be? Imagine a life with zero self doubt and unshakable self worth. Get your copy of Worthy plus some amazing thank you bonus gifts for you@worthybook.com or the link in the show notes below. Imagine what you'd do if you fully believed in you. It's time to find out. With Worthy, who you spend time around is so important as energy is contagious and so is self belief. And I'd love to hang out with you even more, especially if you could use an extra dose of inspiration. Which is exactly why I've created my free weekly newsletter that's also a love letter to you delivered straight to your inbox from me. If you haven't signed up to make sure that you get it each week, just go to jamiekernlima.com to make sure you're on the list and you'll get your one on one with Jamie weekly newsletter and get ready to believe in you. If you're tired of hearing the bad news every single day and need some inspiration, some tips, tools, joy and love hitting your inbox, I'm your girl. Subscribe at jamie kernlima.com or in the link in the show notes. And please note, I'm not a licensed therapist and this podcast is not intended as a substitute for the advice of a physician, professional coach, psychotherapist, or other qualified professional.
Gary Vee: Your AI & Social Media Must-Knows + 7 Life-Changing Keys to Success! Pt 1 Gary Vaynerchuk
August 19, 2025
Jamie Kern Lima
Gary Vaynerchuk (Gary Vee)
In this rich, heartfelt episode of The Jamie Kern Lima Show, Jamie welcomes visionary entrepreneur Gary Vaynerchuk, known to millions as Gary Vee, for the first part of a conversation focused on overcoming self-doubt, building unshakable self-belief, and navigating the uncertain future shaped by AI, social media, and rapid technological change. The episode explores Gary’s unique mindset, his philosophy about success and regret, the crucial role of his upbringing, and how a focus on love and empathy powers not just his business life but his entire approach to people.
Regret vs. Judgment (00:00; 12:00; 41:54):
The True Pandemic: Insecurity (07:35):
On Being a Born Communicator (18:21):
Memorable Visual:
This episode blends tactical mindset advice with personal storytelling, keeping an energetic yet deep tone reflective of both Jamie Kern Lima’s warmth and Gary Vee’s passion. Part 2 promises a deeper dive into AI, the future of jobs, and actionable strategies for surviving and thriving in the digital era.