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This is the art of charm.
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Learn everything you need to know to crush it in business, love, and life.
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Hey everybody, today we re talking with Gary Vaynerchuk.
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Yes, again, but so soon?
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Yes, exactly.
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He s releasing a new book called Ask Gary Vee.
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This is a great one.
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I mean, look, it came up really quick.
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I thought, ugh, what am I gonna talk about?
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I ended up running out of time with plenty left over in the tank.
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We get pretty personal.
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and we get pretty detailed with competitive instinct, with young entrepreneurs versus old entrepreneurs, and working inside and outside of the system.
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There s so much here in traditional Gary V style, so enjoy this one, I know you will, with Gary Vaynerchuk.
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And with that, welcome to The Art of Charm.
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I m Jordan Harbinger.
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The Art of Charm brings together the best thought leaders, teachers, and exceptional individuals to teach you how to be a top performer in life, love, and at work.
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Imagine having a mix of experienced mentors teaching you their expertise, packing decades of research, testing, and tough lessons into a curriculum.
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We may not have all the answers, but we definitely have all the questions.
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Make sure to stay up to date with AOC and get some great stuff that we don t or can t share on the show by signing up at theartofcharm.com.
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We ll email you our fundamentals toolbox that covers topics like body language, nonverbal communication, persuasion, business networking, public speaking, negotiation, and a whole lot more.
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I m also doing regular videos with drills and exercises to help you move forward every single week.
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I want to encourage you as well to join us in the Social Capital Challenge at theartofcharm.com slash challenge or text charmed to 33444.
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That s C-H-A-R-M-E-D to 33444.
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This challenge is about improving your networking and connection skills and inspiring those around you to develop a personal and professional relationship with you.
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This will make you a better networker.
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It will make you a better connector.
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And if you want some accountability, invite your friends as well at theartofcharm.com slash challenge or text charmed to 33444 and they can join the challenge too.
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All right, here s Gary V.
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In this one, I m not, in theory, gonna try to get super deep with you personally, but I wanna focus on the new book, which is entitled Ask Gary Vee.
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And in the spirit of the new book, I m gonna take the opportunity to ask you a bunch of questions that I not only got from show fans after we did our first recent episode a few months back, as well as Art of Charm alumni, instead of doing what we did last time, which is kind of crafting a story around you.
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Of course, that s likely to break down the second we get into really interesting stuff, so as usual, we re not glued
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to the roadmap, and for those of you listening, we re gonna link to the earlier Gary Vee interview in the show notes, so you might wanna go listen to that after you listen to this one to get even more wholesome goodness from Gary.
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So, my first question is, why do you keep writing books?
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And I say that, I put a little bit of stank on that.
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It s not just because you have something to say, because you got other platforms for that.
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It s not just a direct money play, because publishing sucks for that, generally, unless I m missing something.
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No, I make way more money speaking and other ways to monetize the personal brand.
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Right, so is this street cred for speaking or is there more to the story that I don t get?
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I think it s street cred for speaking for a lot of people and if you re listening and you re just getting going, even for you guys, I think there s some validity against that and other people.
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I had that happen in 09, 10, 11, so I m past that too.
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There s a really funny answer to this question.
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There s a lot of people that are the complete opposite of me.
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They actually consume information much better in written book form and there is a stunning amount of people who love reading books and consuming and don t want to watch a 20 minute video and don t want to follow every social media person and click a link and read a medium that their choice, their preference to consume information
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is in Kindle or print form when they re traveling on vacation or before they go to sleep, they like reading a book.
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This is literally eating my own dog food of not being romantic about any platform and recognizing there s a lot of ways a lot of people consume information.
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And every three years or so, I kind of gathered up
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put it together in $20 book form, and away we go.
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So I actually think there s a real tremendous ROI to a lot of people that it costs $20, they can read it in three to five hours, they like it.
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And so I m not trying to impose my will of how people shouldn t consume information in
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world, instead I m just unromantic about it and I m producing it in a medium that clearly millions of people still prefer.
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Yeah, this sounds so weird for someone like me, but I just got back into reading and the reason that I like it so much, well one, I had to because everybody sends me galleys, nobody says I made a 20 minute video that summarizes my new book, that s yet to happen.
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That would be awesome, but it doesn t happen.
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So I started reading again, on the Kindle I plow through stuff, but what I love about reading is it forces the thought leader to really explain everything because so many people are looking at these drafts and then there s an editor who like doesn t care about what you do looking at it and it has to make sense to them.
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and the publishers got people looking at it who have no idea who the hell you are maybe, so they re looking at it, versus a video which is great to get an authentic feel for someone s personality, but the information might not be as clear as it is in a book where there s so many people nitpicking everything you say.
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Hell, I sent you a thing where I was like, oh, I think this is a mistake that you wrote in the book.
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And you were like, yeah, hopefully we got that.
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And then Alex, your assistant, got back and was like, nah, dude, I think you re just misreading it.
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And I m like, I don t know, because everybody s smarter than you when you re looking at a book.
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And I just realized, wow, I m probably one of like 1,000 people that sent in something like that.
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And when something s getting picked apart that much, there s going to be a lot more detail in it.
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And some people love that.
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I like that.
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I think a lot of people, yeah, millennials probably hate that stuff, because they just want, look, quick info.
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And I m with them on that most of the time.
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You know what s awesome, though?
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The book is made in that way.
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I mean, I m talking a lot of shit to my audience about Perfectly Parented, and I wish everybody was an immigrant, and all these other books I want to write, but I ll be honest with you, the early feedback from people that are getting to scratch both their itches, the fact of the matter is, I wrote it in a way where it s Q&A, and there s chapters, and so I ve been stunned by how many people have hit me up that are reading it for reviewing purposes, and here s the punchline.
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of people that don t even like me.
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They have to do it because they re writing it for their magazine or website, and these are people, literally, I ve gotten emails that are like, hey man, I ll be honest with you, I thought you were a douchebag, but I always had people around me saying, no, he s a good guy and he s smart, so I was like, eh, and then I had to read this, because I m the one that s responsible for reviewing it, and I gotta be honest with you, man, it s a great book, and what I like best is I can read chapter 13, then I read chapter 19, then I went back to one, it s built in a format that s more made for my brain,
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and I think the format is gonna give me a chance to have a format that I can go back to the well with and I think a lot of people are gonna enjoy.
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Obviously you re a workaholic of some kind, kinda like me.
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You love building things, you love making things, at least we can maybe agree on that.
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People talk about work-life balance.
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This is like a buzzword thing.
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People talk about it a lot, how it doesn t exist because of internet, blah, blah, blah.
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Where do you stand on that?
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I stand on it being a very, very individual thing, meaning I have no interest in imposing my work-life balance on anybody else.
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Jordan, I don t know if you ve been seeing, but these DailyVees, these kind of daily vlogs I ve been putting out, they ve really created an interesting storm for me in two directions.
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Number one,
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People are emailing me and saying, geez man, I ve followed you for seven years, I ve heard you talk about hustle from the day I met you.
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I didn t get it.
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You re like really working at a level that makes me feel uncomfortable.
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They re saying that as a good thing.
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And then there s other people saying, hey man, cool and great, great job buddy, you re gonna be a billionaire and buy the Jets, but your family s gonna hate you and you re gonna regret this and you re gonna die lonely, right?
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And so, Lizzie and I have our work-life balance.
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We communicate about it, we grew up a certain way, both with fathers that worked their faces off in different ways for different reasons.
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Mine immigrant and ambitious, Lizzie s ambitious and corporate superstar.
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And so, I think that it s a common conversation.
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But I think it s kind of like raising kids, right?
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I would never have the audacity to tell somebody how to raise their children, because every individual situation s different.
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People aren t in my bedroom.
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They don t know what makes me and my wife happy, or me and my kids, or how things play out, or the fact that when I m home, I mean, this is literally one of the first times in three years that I m actually doing a work thing on a weekend.
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Why?
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Because it s two days before my book comes out and I m in that zone and I m okay with doing that once every three years.
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But I m all in when I m around.
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A lot of people who judge my work-life balance, a lot of people that are going to tweet about this podcast around this issue, when they re home, they re looking at their phone, they re playing video games, they re not really engaging mentally with their spouse or their children.
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And so, I don t think it s a quantity game, I think it s a quality game.
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I also think that you re speaking right now to a guy whose dad, he didn t even know until 14 years old, because he worked every minute, and I have the greatest relationship in the world with my dad, and I love him so much, and I ve been massively fulfilled.
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If either one of us leave the earth tomorrow, I will feel phenomenal of the quality of our relationship, and the depth, and the time.
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I think people think in micro moments, yes, I get it.
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You ll never get back the moments when a kid is three and they do the first this, that, and the other thing.
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On the flip side, you never get back the moments in the 20s, 30s, and 40s.
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When my parents and I go on vacation together, I go and lay in their bed until two in the morning.
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Right, talk to them.
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And that comes out of having a great relationship and that doesn t happen for a lot of people who saw every wiffle ball game and every dance recital and then their kids turn 18 and never want to come back, right?
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So I have no interest in telling people how to live their work life balance.
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I m thrilled for anybody to critique mine because I understand I put myself so out there so I deserve it.
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I have no interest in trying to defend against it.
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I just want everybody to know
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The only people that I m going to respond to around this conversation are the 11 people in my most inner circle of my family who are the people that I most care about around this issue.
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I think that s wise.
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Not Rick from Kansas, who I adore, who probably bought 15 copies of this book, who I would love to talk about a million things about business, how to help him.
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I m here for you, but trust me, brother, I have no interest on your point of view on something that I spend all my time and effort on every day, communicating with those 11 people.
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11 people.
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I think that s really wise, because I think a lot of people spend way too much time listening to other people on every issue, but work-life balance, it s a really intimate topic, and it s not something that anybody s figured out for everyone else.
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It s impossible to do that.
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It s intimate, boy.
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It s intimate, boy.
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To me, that s like getting into your sex life territory.
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Yeah, exactly, exactly.
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I agree with that, and I think if you re a guy like yourself, who s got everything turned up to 11 a lot of the time,
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If you re turning up the family life stuff and it s like, okay, I m done with work, we re not just gonna sit around and watch TV, we got plans, we re going to the zoo, and then after that we re gonna go have a nice lunch, and then we re gonna go visit grandma and grandpa, and then we re gonna take naps, and then we re gonna get up and go to the movies, you re packing in great experience, and it s not just, yeah, you re not just playing Mario Kart with your kids for five hours and being like, I parented today, right?
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Yeah, and by the way, and that s fun too.
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Five hours, just chill.
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What s everybody s point of view in four years when I take Xander and Misha to every Jets road game and we leave on Friday nights and we have all that time on Saturday because we went to San Diego on the road and we went to the San Diego Zoo and then we went to the game and then they re meeting their favorite football players on the field.
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There s a lot of benefits from doing successful business things that then you build up the leverage and then you get to deploy it.
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You know, like by the way, when I went to Misha s recital the other day from nine to 11 in the morning, I did that by looking myself in the mirror and deciding that it s unfortunate and it makes me sad and my heart breaks for the thousands, tens of thousands, hundreds of thousands of individuals who can t go to that recital because their boss wouldn t give them off that day.
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I mean, this is a very in-depth conversation.
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Yes, I work 15 to 18 hours a day all the time, hundreds of days a year.
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But by the way, there s still 100 days a year left, 125 days a year left where I can do enormous amounts of things.
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The end.
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Yeah, I feel like people impose a lot of this stuff on other folks, and I don t have kids, so this equation may change.
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I feel like people impose this on others because of their own kind of guilt.
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Of course, which is why, look, I m so content and so ambitious at the same time, but out of my contentness, I have no interest in judging others because it s not gonna make me feel better about myself.
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I already feel the best about myself.
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That s great, actually.
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I like that.
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I don t know what else to do with that.
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I mean, it s a very important thing.
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When you get into the best place with yourself, it s stunning how you treat others.
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You know why I m a good dude?
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You know why everybody that really knows me undercover feels good about me and what s building up as my reputation as I m starting to chip away?
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And by the way, I m only gonna get way stronger and way more liked and way bigger and way better because of it.
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It comes out of being,
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happy with myself, it then gives me unlimited ability to help others.
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Like it s just easy for me, because I don t need anything from anybody.
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Right, your cup overfloweth, as they say somewhere.
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Jordan, when we sat down and said, look, we need to do podcasts for the book, and in the first breath, Art of Charm pops up.
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I m so proud of you, you re fucking crushing it.
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The first words out of my mouth,
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You could have saw it.
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I was like, guys, I just, I didn t do it that long ago.
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I m like, listen, if he comes back and says, no, that s going to make a lot of sense for me.
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And please reply with like, thank you so much.
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And like, is there anything we can do for you?
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Because I default into wanting to provide 51% to the other person.
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I know what to do with my 49.
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I m that talented.
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I m that good.
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I m that hungry.
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I m that strong.
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I want to work that hard.
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And when you get into that place, when you get into that real zen place, well, then you become massively liked because you become really not selfish.
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You really deploy empathy at scale, which is something I wrote about in this book on purpose.
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You start really caring about what the other person cares about.
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And my thought is I m so fucking jazzed up for this interview.
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And I think the reason I ve already had two or three good things in this interview is I feel so guilty that you re having me back on that.
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I m like, OK, I need to deliver like seven
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15 fucking zingers, all time zingers, that he can use as micro quotes for his, maybe he wants to use Anchor and he ll take some of the audio from here, maybe he ll turn it into quote cards, maybe I ll say one of the best things I ve ever said and that becomes a gateway drug to the other A-listers that want to do this show, because they re like, oh, Jordan must be able to extract great stuff from people.
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I don t know, but I can tell you my mental energy level, like my workout this morning, before this interview, even Mike was like, man, and I m like,
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man, I need to deliver.
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I think today Jordan and I produce one of the best singular episode podcasts in our genre ever.
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I ll take it, and I ve got plenty to throw at ya, and I know you can rock it back.
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One of the questions that I get all the time that I can t answer because I just don t know the answer, when do we quit if something isn t working?
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There s this whole idea, never stop till you win, and then there s this whole, yo, this isn t working, this ain t working, it never will, cut your losses and run.
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I shut down VaynerLive, our live events division.
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I shut down VaynerSampling, our sampling division.
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I m about to integrate my GrapeStory influencer marketing business, separate business, into VaynerMedia Media s division, human media.
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Once ran a social network called Quarked.
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I helped co-found a developer designer community called Forest.
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I started another video blog where I was the producer half owner called Obsessed TV.
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I did Daily Grape for only 84 episodes after I finished 1,000 episodes of Wine Library.
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TV, I stop shit all the time, and nobody, and I mean nobody, is more tenacious than me.
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Like if I get into a fight to the death, I will literally die with the most effort you ve ever seen.
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If I m down 20 to zero in a pickup game to 21, I m literally yelling at my four other homies and saying, guys, I m not joking, I think we can run off 22 straight.
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Like, I ve got nothing but tenacity, however,
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Energy and time are your biggest assets, not the money.
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It s the energy and time.
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So I would say that there s a balance.
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Everybody s got their own internal guiding light.
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What I want to do here and why I just ranted seven or eight of nine, my recent failures, what I call my micro failures, not my macro failure, is outside of like, you go into debt, out of business and you have to get a job, outside of like, you get a divorce if you didn t want to, outside of the death blow, outside of the death blow,
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you always fight if there is a death blow, but if it is just a micro loss, if it is just kind of like Mortal Kombat or something, if it just takes out half your energy or your arm just falls off and you didn t die, well then you can let that happen.
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You ve got to accept micro losses, it s part of the game.
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You know what s funny?
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This is an interesting time to talk about this, because I ve been using this analogy, and last night it played out real true.
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I compare entrepreneurship to UFC.
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In UFC, everybody s going to lose.
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Everybody last night both favorites that we wanted to win lost right they lost and so it just happens You re gonna lose.
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It s not boxing.
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You know, it s not chess UFC is very similar entrepreneurship There s gonna be losses along the way Too many people listening right now are worried about what their mom and dad what their girlfriend what their homies that told them not to do it think when they ve lost and
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on the execution that they decided to do when they left their job, and they don t want the shame amongst them.
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And I m here to tell you that those people don t fucking matter.
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They matter in life, but they don t matter in the arena of entrepreneurship because they don t get it.
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Because anybody that tells you to not do it is scared of it.
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Yes, I agree with that, and I think when a lot of people are making a decision to quit, whenever anybody asks me this question, because like I said, I get it all the time, and my answer seems to change a lot, it s always, what are you most afraid of?
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And very rarely is it like losing my house, it s usually like, they re all counting on me, or like, they don t think I can do it, and there s a part of me that just wants to prove them wrong, and it s like, okay, if that s the reason, eliminate that from your mind as much as possible, because then we were just talking about ego, and you see people
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like a second mortgage on their house to show their ex-wife that they re not a loser.
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That s just a terrible calculation, but I understand it.
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100%, and I understand it tremendously, and here s what I ll say one more time.
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Win the marathon and lose the sprints.
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I mean, it s very simple, right?
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Like, it s all the cliche stuff.
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Be willing to lose battles, win wars, right?
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Right.
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like have three business failures.
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You ve gone from a nice apartment to a worse apartment.
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Now you live in a rental studio.
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Now you live in a trailer, but then you build a $10 million business.
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You won.
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You won in a 17-year period.
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You just happen to lose in a three-month, three-year, five-year period.
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It s just about how does it end?
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How does it end?
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By the way, Jordan, that s why I roll the way I roll, man.
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Like I m not crippled by people thinking I m full of shit or a douchebag or too much ego when they first consume me, because I know where they end up.
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I know that 50% of the people that are listening right now, or 30% is probably true, of the people that are listening now that know who I am, started off not loving me.
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I am one of those people.
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I ll tell you.
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I ll admit it.
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Wait a minute.
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I didn t know that.
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I m excited because that works out nicely.
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It does.
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Tell me where you first consumed me.
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I ve got a guarantee it was in a public forum because I m batting a thousand if I meet you in a private forum because I m a different kind of energy in that sector.
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Do you know?
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Yeah, I do, I do.
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My friend Paz, who s a fan of the show, he s this Thai guy, and he s like, oh, I know Gary Vaynerchuk, because we talk on Twitter, and I was like, whatever, that guy talks to everybody on Twitter.
2
SPEAKER_03
You know, I was like, I don t like wine, this is stupid, and I watched an episode of Wine Library, and I was kind of like, oh, he s funny, I like that he said the wine tastes like racquetballs, because that s what wine, all wine for me tastes like, some version of rubber.
2
SPEAKER_03
Things that you don t want to eat and then we did an interview We had us one of our prior first or second year podcasting in your office, and you were really nice, and I thought okay He s a really nice guy personally, but I still there s just something about him.
2
SPEAKER_03
That s a little off I don t know maybe I don t believe that he believes what he s doing and
2
SPEAKER_03
And then I followed your stuff for a while and I was like, he clearly really believes what he s saying.
2
SPEAKER_03
So I admire that, but I m still not fully interested in a lot of this stuff.
2
SPEAKER_03
And then I saw the book and I was like, there s a whole chapter that just says care.
2
SPEAKER_03
This is lazy.
2
SPEAKER_03
I m not sure about this guy.
2
SPEAKER_03
And I slowly came around, but it took like seven years or something.
2
SPEAKER_03
I m stubborn.
2
SPEAKER_00
Well, yeah, I mean, for everybody listening that doesn t know, the care chapter was in Crush It!, I mean, that s 2009.
2
SPEAKER_03
Yeah, so this, what, seven years later?
2
SPEAKER_00
And you know what s so funny?
2
SPEAKER_00
It s so funny when one s mindset is in a certain place, how they decide to figure something out.
2
SPEAKER_00
No joke, and this is gonna make you laugh, Jordan, the number one thing in my life that I ve been emailed about over the last decade is chapter nine of Crush It!, one word, care.
2
SPEAKER_00
Really?
2
SPEAKER_00
Yes, the number one thing, not the web 2.0 talk that put me on the map, smurf it up, you know, stop watching fucking lost, not the real recent run of a lot of big hits like the Monday morning thing where you could have been a bus, fuck you Monday, or the six minutes for next 60 years, two things that have gone quote unquote viral for me, not DailyVee which has been a game changer for me these 19 episodes of this vlog, not appearances on TV, not my first Conan appearance,
2
SPEAKER_00
not Twitter and Facebook going public after I said they would, not the Snapchat phenomenon that s happening for me right now of getting way too much credit for something I don t deserve of like, oh, you got people on Snapchat.
2
SPEAKER_00
It has been that chapter, that word, and people literally emailing me saying, I ve been selling $900 e-books, I m a scumbucket, I m selling supplements that I have no idea what s in there, I m a scumbucket, and something about that chapter, that word, fucked with my head, and you ve changed my business.
2
SPEAKER_00
This is what s happened over the last 18 months.
2
SPEAKER_00
chapter, that word.
2
SPEAKER_00
And you going into the mentality of like cynicism, which is what you re referring to.
2
SPEAKER_00
Which by the way, Jordan, you have to understand, here s why it never bothers me.
2
SPEAKER_00
I agree with your cynicism.
2
SPEAKER_00
I know that I m unusual.
2
SPEAKER_00
I know that most people that sell good are full of shit.
2
SPEAKER_00
I know that people haven t quantified that I didn t talk to the world until I was 30 years old and had already built a 50 million dollar business and that was wine and I didn t talk to the world about business or motivation or hoopla or marketing until I was 34 years old and had already built a 60 million dollar business and had already invested in Twitter and Facebook
2
SPEAKER_00
Jordan, I was 34 years old and an accomplished businessman before I came out and became this guy that maybe peddled things that the world would be cynical to.
2
SPEAKER_00
And I knew that my personality and my bravado and my showmanship would disguise my very practical, very tangible, very meat and potatoes,
2
SPEAKER_00
kind of accomplishments, and that that s why I know I m different.
2
SPEAKER_00
Most people that sell what I sell, sell it out of the gate because they re taught by a motivational coach to sell motivation to other people, yet they ve never accomplished anything in their lives.
2
SPEAKER_01
Over the last 17 years, we have launched our fair share of online courses, coaching programs, and finding the right platform has always been a challenge.
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SPEAKER_02
Hey Art of Charm listeners, I m excited to share a new podcast I ve been absolutely binging.
2
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2
SPEAKER_02
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SPEAKER_02
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2
SPEAKER_03
Yeah, I agree with you.
2
SPEAKER_03
And look, to be clear, it didn t really take me seven years to come around.
2
SPEAKER_03
I liked you well before that.
2
SPEAKER_03
And it s funny because now people who have the exact same comments that I do, where they re like, oh, this frickin  loudmouth, I m like, no, no, no, trust me.
2
SPEAKER_03
And I find myself saying exactly what somebody else would have said to me probably five years ago when I said those things.
2
SPEAKER_03
And it s funny because, like many wines, it s an acquired taste.
2
SPEAKER_03
You know, you gotta get past the stuff that bugs you
2
SPEAKER_03
and a lot of people love the energy up to 11 and stuff.
2
SPEAKER_03
At first, though, I just thought, he s using that to overcompensate for a lack of whatever, and now I just realized you re really excited about everything.
2
SPEAKER_00
Listen, man, and you know what s funny?
2
SPEAKER_00
It s funny for my grammar school and high school and other people, because they remember when there was no camera on, and I get these emails all the time, and it makes me feel good, because it does help me almost remind myself, because you know what s funny?
2
SPEAKER_00
I think the reason I really can pull it off is I m more cynical about myself than anybody outside of me.
2
SPEAKER_00
I believe that.
2
SPEAKER_00
I m sure.
2
SPEAKER_00
Yet, meanwhile, I equally, more than anybody, think that I m going to end up all-time.
2
SPEAKER_00
Like, Jordan, I literally sit here with you right now, and there s nothing, zero doubt in my mind, that I m the guy of this generation.
2
SPEAKER_03
That s a strong belief system.
2
SPEAKER_00
Especially when right now anybody listening knows that I m dramatically behind Zucks or Travis or Elon Musk or, you know, even from a kind of a personal brand standpoint, Ferris or Tony Robbins or Tony Hsieh, like, and from a business, like financial, like hundreds of thousands of people who ve made more money already, but I know what I m doing.
2
SPEAKER_00
If I pull off what I think I ve got in me, I think it s a,
2
SPEAKER_00
more hyper-successful version on both ends of a Richard Branson, both financially and impact on people.
2
SPEAKER_03
I hope so.
2
SPEAKER_03
That would be really cool.
2
SPEAKER_03
People download a lot more of these interviews.
2
SPEAKER_03
They ll be looking for them at that point.
2
SPEAKER_03
They still are.
2
SPEAKER_03
They already are.
3
SPEAKER_00
You know what s funny about that?
3
SPEAKER_00
It s funny how your brain thinks.
3
SPEAKER_00
I think about that shit too though.
3
SPEAKER_00
That s funny you just said that.
3
SPEAKER_00
You know what, I m gonna make you happy right now and I want everybody to hear this because I think it s gonna make them understand how I think about the world.
3
SPEAKER_00
That statement is probably the single thing that I ve heard come out of your mouth or on public or on a tweet or anything.
3
SPEAKER_00
I just liked you more than I ever have before on any move because it means that you re thinking about the marathon.
3
SPEAKER_00
You re able to project that in 29 years, this is what I m talking about by the way, I m 40 years old.
3
SPEAKER_00
Like, I m 40.
3
SPEAKER_00
Like, in 20 years, I ll be 60, and I feel good about that.
3
SPEAKER_00
That s a long time.
3
SPEAKER_01
You ll have a lot left in the tank at 60.
3
SPEAKER_01
I can make that prediction about you.
3
SPEAKER_00
A lot.
3
SPEAKER_00
And so, listen, I ve been right about so many things.
3
SPEAKER_00
When I bet on the virtual reality Facebook, and I own 10%, and I m Peter Taylor,
3
SPEAKER_00
Peter Thiel, for people that don t know, Peter Thiel owned 10% of Facebook.
3
SPEAKER_00
He made a lot of money in PayPal, but obviously he made a lot more money with the Facebook bet.
3
SPEAKER_00
I m convinced I m gonna make that kind of bet in my investing world.
3
SPEAKER_00
I m gonna build VaynerMedia into a billion dollar company.
3
SPEAKER_00
VaynerMedia s gone from four to 100 million in revenue in literally in four years.
3
SPEAKER_00
Agency sell for two to three times revenue.
3
SPEAKER_00
So right now, people don t get it.
3
SPEAKER_00
People are stupid, Jordan.
3
SPEAKER_00
People Google my net worth, that s the second biggest search term for me.
3
SPEAKER_00
There s some cockamanian website that puts my net worth at 10 million.
3
SPEAKER_00
And that s what people think it is.
3
SPEAKER_01
I looked it up at Thrive, because I was like, is that accurate?
3
SPEAKER_01
And then 10 minutes later, you told us about VaynerMedia.
3
SPEAKER_01
And it made me wonder how they calculate those things.
3
SPEAKER_01
But it made me feel a little bit better about myself for a minute.
3
SPEAKER_01
I ll give you that.
3
SPEAKER_00
I mean, for example, I don t want to go here, but I want to teach people how stupid things you read on the internet.
3
SPEAKER_00
I m going to make more than $10 million this year.
3
SPEAKER_00
Like, as my income.
3
SPEAKER_00
Like, it s so stupid.
3
SPEAKER_00
Like, all you have to do is look up Wine Library s property value.
3
SPEAKER_00
Like, the property that my wine business sits on is worth more than that.
3
SPEAKER_00
So, people are not smart about, like, things.
3
SPEAKER_00
Like, people, like, hear hucksters that claim they make, that their net worth is $25 million, and they re like, see?
3
SPEAKER_00
He s better than Gary Vee.
3
SPEAKER_00
And I m like, you are a fucking idiot.
3
SPEAKER_00
This guy s selling infomercial products.
3
SPEAKER_00
Like, you re an idiot.
3
SPEAKER_00
And there s a million of them.
3
SPEAKER_00
There s so many people that don t get it, don t understand the game.
3
SPEAKER_00
And so for me, I like that you re thinking 25 years out because you re right, because you re damn fucking right.
3
SPEAKER_00
These two interviews that we ve done, you re going to get a shitload more listens in 2031 than you are right now.
3
SPEAKER_00
when everybody wakes up one morning and whatever the Business Insider or Wall Street Journal or whatever the fuck we re listening to starts with, today, virtual virtual sold for $47 billion.
3
SPEAKER_00
Investor Gary Vaynerchuk made a wise bet eight years ago and owned 10%.
3
SPEAKER_00
Big day for him, guess he s gonna buy the Jets after all.
3
SPEAKER_00
When that fucking day happens, people are gonna Google or whatever the fuck they re doing then, they re gonna find this and they re gonna listen to every fucking word.
3
SPEAKER_00
And you know what, let me actually take myself out of this moment and put myself in 20 years from now.
3
SPEAKER_00
Hey everybody, that s right, uh-huh, exactly.
3
SPEAKER_00
I always knew it, because when you understand yourself and you deploy self-awareness, you get to navigate at a surgical level, and that s how you win, whether you re doing what I m doing, or you become the best parent of all time, or the greatest policy maker, or the greatest non-profit fundraiser, or whatever you want to achieve in your life, it is nothing but being self-aware and deploying all your energy against it, just like LeBron James did, just like Whitney Houston did, and just like every great entrepreneur did.
3
SPEAKER_01
I love that, I think there s gonna be people who email and go, I turned it off when he started talking about all of this stuff, and it ll be like the things you just said in the last three minutes, for sure.
3
SPEAKER_00
I truly hope not, and I truly think that the people that do that, if you forward them to me so I can have a five minute one-on-one conversation, I would do that, because anybody that was scared of what I just said is wired for failure in the short term.
3
SPEAKER_01
The long-term marathon theory, and you ve mentioned this a lot, I think about it all the time because a lot of people go, you know, you should start charging for the episodes of this.
3
SPEAKER_01
There s premium content you can do now.
3
SPEAKER_01
Oh, you can have people sponsor the show with recurring income.
3
SPEAKER_01
And they don t understand the strategy because I m thinking about
3
SPEAKER_01
Alright, how do I become the next Larry King, only a little bit more dynamic and no suspenders?
3
SPEAKER_01
You know, I m thinking of that kind of thing, and most people are not interested in that.
3
SPEAKER_01
They re trying to think about how they can buy a Ferrari Enzo in the next two years, or one year, or whatever.
3
SPEAKER_00
Jordan, you know what s even scarier?
3
SPEAKER_00
So that s alright, next.
3
SPEAKER_00
They re not even thinking about buying the Ferrari.
3
SPEAKER_00
They re thinking about how do I rent the Ferrari, take a picture and put it on Instagram and make people think that I m a winner and then leverage that.
3
SPEAKER_00
It s even worse.
3
SPEAKER_01
Yeah, you re right, that s even more sort of meta.
3
SPEAKER_00
That s 90% of it.
3
SPEAKER_00
You know it, we know what we re circled around with.
3
SPEAKER_00
That s 90% of it.
3
SPEAKER_00
If they actually wanted to do the behavior to buy the Ferrari, I d be more excited.
3
SPEAKER_00
It s not even that.
3
SPEAKER_00
It s like literally not even that.
3
SPEAKER_00
It s how do I arbitrage renting the Ferrari?
3
SPEAKER_00
I m gonna rent a baby giraffe.
3
SPEAKER_00
I m gonna get some models or strippers from Vegas in the shot.
3
SPEAKER_00
I m gonna put it on Insta.
3
SPEAKER_00
People are gonna think I m living the lifestyle.
3
SPEAKER_00
I m gonna arbitrage that and I m either gonna sell them on how to get there even though I didn t or some other horse shit.
3
SPEAKER_01
It s all about those baby giraffes.
3
SPEAKER_01
I don t know where that came from.
3
SPEAKER_01
I don t know if you had that in the can or if it just popped in your head.
3
SPEAKER_00
No, I think I saw some picture along the way.
3
SPEAKER_00
I don t know if it was a Blazarian party or some horse shit, but there was a baby fucking giraffe that somebody was holding.
3
SPEAKER_00
And I was just like, this shit is taking it.
3
SPEAKER_00
It s one thing to get your buddy to take his money out of the bank and put it on a bed in a hotel room, 100,000, take a picture and then put it back in the bank and go that way.
3
SPEAKER_00
It s another thing to rent a big time watch for the day and do that.
3
SPEAKER_00
It s another thing to spend a couple Gs to rent a big time car, take a picture and act like you bought it.
3
SPEAKER_00
It s a whole nother fucking thing to put a baby giraffe in your photo.
3
SPEAKER_01
That is, you re right, that is next level showmanship for sure.
3
SPEAKER_01
This does lead into an interesting question.
3
SPEAKER_01
How do you know if you re an entrepreneur in the first place?
3
SPEAKER_01
Because I think a lot of people are more interested in faking it.
3
SPEAKER_01
Do you think people are hardwired for this or is it developed over time?
3
SPEAKER_00
I think the winning entrepreneur, and what I say by the winning entrepreneur is somebody who can amass a million dollars, I think is an outrageous winner, and I would say even 500.
3
SPEAKER_00
Somebody who can really do it and live a top 5% lifestyle on their own terms and their own business, I think that s hardwired.
3
SPEAKER_00
I do think that people can become the best version of an entrepreneur of themselves by studying, by putting themselves out there, by learning their craft, but I think of it the same way I think of athletics, I really do.
3
SPEAKER_00
Jordan, do I think I can become a very good hockey player even though I ve never learned how to ice skate?
3
SPEAKER_00
The answer is yes.
3
SPEAKER_01
Really?
3
SPEAKER_00
Do I think I could become somebody that could ever be anything more than a guy who could be solid in a rec league?
3
SPEAKER_00
Absolutely not.
3
SPEAKER_01
Ah, okay.
3
SPEAKER_01
I was like, you got a long way to go if you re gonna be in the NHL.
3
SPEAKER_00
So that s the problem, and that s where your head went.
3
SPEAKER_00
Everybody listening, everybody reading all this stuff, everybody thinks they re gonna be on the pathion of like a millionaire.
3
SPEAKER_00
Do you know how hard it is to be a millionaire?
3
SPEAKER_00
You know what the data is?
3
SPEAKER_00
What is the data?
3
SPEAKER_00
No, I never looked at it, actually.
3
SPEAKER_00
The top 1% in the United States makes $428,000 a year.
3
SPEAKER_00
And that s across all age groups.
3
SPEAKER_00
By the way, that s your gross income.
3
SPEAKER_00
Adjusted gross income, not your net.
3
SPEAKER_01
Right, and this is across all age groups because it s different for 18 to 34, 34 to 45, or whatever.
3
SPEAKER_00
Yeah, this is the U.S.
3
SPEAKER_00
tax return, people, right?
3
SPEAKER_00
Mm-hmm.
3
SPEAKER_00
So, that s it.
3
SPEAKER_00
Do you know how hard that is?
3
SPEAKER_01
Yeah, actually.
3
SPEAKER_00
I mean, you know how crazy that is?
3
SPEAKER_00
Like, literally, I m doing a CNN money calculator.
3
SPEAKER_00
Here we go.
3
SPEAKER_00
$400,000 a year.
3
SPEAKER_00
If you make $400,000 a year, you are better than 99% of the rest of America.
3
SPEAKER_00
I made $400,000 in two talks.
3
SPEAKER_01
Yeah, that was a great speaking for you.
3
SPEAKER_00
Guys, this is math.
3
SPEAKER_00
Do you know what happens when you re the top 1% basketball player or singer or surfer or anything?
3
SPEAKER_00
And so what?
3
SPEAKER_00
Because you re gonna read one of my fucking books and listen to this podcast and go to a fucking class, you all of a sudden are gonna become that?
3
SPEAKER_00
It s ludicrous.
3
SPEAKER_00
Talent is absolutely part of the equation of being a big time entrepreneur.
3
SPEAKER_01
I think there s an element as well of stealing yourself to criticism, and this is from the book.
3
SPEAKER_01
You say, if you want to be an entrepreneur, if that s what you really, really want, you cannot give a shit about what other people think of you, not even your parents.
3
SPEAKER_01
I won t lie, people will criticize you, they will say mean things, maybe even hateful things.
3
SPEAKER_01
often because they re jealous that you had the guts to get out there and do your thing, or because they love you very much and are scared for you, and that s okay.
3
SPEAKER_01
If you truly trust and believe in yourself, you will learn to ignore them, and they will learn to accept your decisions.
3
SPEAKER_01
And this was a massively important realization for me personally.
3
SPEAKER_01
I feel like people ask me all the time, how do I steal myself from that stuff?
3
SPEAKER_01
Honestly, I feel like I got criticized a ton as a kid, so by the time I started running The Art of Charm with AJ,
3
SPEAKER_01
It didn t matter what else people said because it was like water off a duck s back.
3
SPEAKER_01
And I know that other people working in this organization at AOC had a different experience and they take criticism a lot harder.
3
SPEAKER_00
I mean, I was told I was a straight loser from first grade to 12th grade because I was a shit student.
3
SPEAKER_01
Yeah, you got terrible grades growing up.
3
SPEAKER_01
What did your hard-working parents think about that, by the way?
3
SPEAKER_01
Because it seems antithetical to be a Jewish immigrant and a terrible student, and yet have a really great work ethic.
3
SPEAKER_01
It kind of makes me think something else was going on all along.
3
SPEAKER_01
Did you know early that you weren t cut out for the traditional path, or?
3
SPEAKER_00
By fourth grade, I started communicating with my mom and dad.
3
SPEAKER_00
Mainly my mom, I was scared she d listen to my dad.
3
SPEAKER_00
By fourth grade, I was saying like, look, I m different.
4
SPEAKER_01
I m going to sell stuff.
4
SPEAKER_01
I m a businessman.
4
SPEAKER_01
I used to call myself a businessman.
4
SPEAKER_01
The word entrepreneur wasn t in the lexicon.
4
SPEAKER_01
You know what?
4
SPEAKER_01
I was unwavering.
4
SPEAKER_01
My mom would slap me.
4
SPEAKER_01
Yes, European mothers punch in the face.
4
SPEAKER_01
My mom would punish me, no TV, no Nintendo.
4
SPEAKER_01
You have to understand, I was like that scary fighter that you would like punch as hard as you can and they would just like spit the blood out on the side and then look you dead back in the face.
4
SPEAKER_01
You know, like that s who I was and that s who I am.
4
SPEAKER_01
Like, I just won t waver.
4
SPEAKER_01
I just have always been very, very, very comfortable in the fact that I felt like I got parented properly.
4
SPEAKER_01
I got the right DNA.
4
SPEAKER_01
I had the right skills.
4
SPEAKER_01
I knew how this was all going to end up.
4
SPEAKER_01
I knew it from a very young age.
4
SPEAKER_01
My teachers would tell me I was a loser.
4
SPEAKER_01
I would be polite because my mom taught me to, but I would in my head say, you re a fucking loser.
4
SPEAKER_01
And I would say, I m gonna show you, I m gonna stick it in your fucking face.
4
SPEAKER_01
And so the other thing is, Jordan, you know what s interesting?
4
SPEAKER_01
I ve spent some time with myself, this is me talking to myself in the last year of, am I cursing and being polarizing on purpose because I actually get motivated by people
4
SPEAKER_01
Underestimating me and neglecting me and saying I m not good.
4
SPEAKER_01
Is that my motivator?
4
SPEAKER_01
You know Mike this morning goes I d like you to get six reps here and I ve got a lot of sleep last night and I m really been on point I was like fuck you Mike and I got seven right and I like it was hard what I was doing and so But I don t think if he said let me get to six here.
4
SPEAKER_01
I
4
SPEAKER_01
Like, let s try to get six here, I don t think you ll get seven.
4
SPEAKER_01
I just, I need the adversity.
4
SPEAKER_01
It s why I love being a Jets fan, Jordan.
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I love the losing.
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And so weirdly, I m asking myself, hey man, are you sabotaging yourself in front of people because you want them to underestimate you?
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because you love the aha, I told you so, got you, I knew you d come around.
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Is there a vanity?
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And by the way, I m not proud of this trait.
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It s not a very noble thing to kind of sandbag yourself because you get off on people underestimating you and then you stunning them.
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Right, it doesn t seem like it would motivate a lot of people.
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It could demotivate a lot of people.
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understand this and took anthropology classes or understood humanity or understand psychology.
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I m sure it s very basic, but I m built that way, man.
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I love the journey.
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I can t lose this game because it s the hunt, right?
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I love the hunt.
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I love the process of trying to buy the New York Jets.
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I ll be fine if I don t.
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I m so scared for all my friends who at 80 and 90 and 70, when they re like, oh man, sorry, they won t understand.
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I want it, yes I do, but it s the hunt that gets me off.
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You obviously have a super competitive instinct.
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Would you agree with that?
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I m the worst version of who I am as a human, is at sporting events.
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I m a really bad guy, I m disrespectful, I m way more alpha than I am on stage and public, as some of you could not imagine.
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I get into fights verbally, I m willing to get physical, I m disrespectful to kids, I curse heavily in front of four and five and seven year old kids, even when the parents turn around and say to me, hey man, and I m like, hey man, nothing fucked faces a football fucking game.
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Like I get crazy.
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That s insane.
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And I m not proud of it.
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I m proud of myself in every place I am, even in the cursing on stage, even in the ego of certain moments, including parts of this interview, I feel proud because I know it comes from a good place.
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I am not, officially, on record, I am not happy with who I am at sporting events.
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It is the worst version of myself.
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It is the place where I can t control my emotion because unlike business and real life where I m in control, I m not in control.
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of Carmelo Anthony or Brandon Marshall, yet I care so much.
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Well, you ll fit right in when you buy the Jets, yelling and screaming on the sidelines.
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I m asking this because at some level, and correct me if I m wrong, because I m imputing this to you, is there a little resentment, or maybe that s not the right word, when you see someone in business that s a little bit ahead of you?
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I m not saying you don t learn from them or anything.
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No, I m in a good place with that.
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I m so happy for everybody that s winning, you couldn t imagine.
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I ll tell you why.
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I believe in meritocracy, and I believe in marketplace dynamics, and if that person has been able to make the right decisions, they deserve it.
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I do not feel that anybody on Earth is winning at my expense.
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That is a great answer, because honestly, I wasn t sure what to expect there.
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Do you feel like other people winning helps drive you forward because they re paving the way?
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Absolutely.
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I mean, I think of Chris Sacca and I think of Travis.
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These are my contemporaries five, six years ago, and they ve gone to billionaire status in a couple of great decisions.
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Travis Kalanick, CEO of Uber.
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That s right.
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And I m pumped.
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I mean, you couldn t imagine how I feel about them.
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Tim Ferriss, I think one of the great personal brands in this space.
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Nothing makes me happier than his winning and I want him to become the biggest like I don t think anybody can eat up all the success not even remotely close and so a Especially people I know and then even people I don t know but I know from afar as long as people are winning in an ethical way and aren t stealing or cheating or ripping off somebody I m very very happy for them even if they are directly in my genre and
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There s a wine startup in Australia that s crushing, directly in my industry, pumped for them.
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Even local stores like Gary s Wine and Liquor, which is ironically my name, Gary s Wine and Marketplace, which is the biggest wine library competitor in New Jersey.
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Some people think I own it, because it s Gary s.
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It s Gary Fish.
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I have a lot of love for him.
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I have respect for him.
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I ve watched him execute for 30 years, and he s done a great job, and he deserves all his success, even though every dollar he makes comes out of Wine Library s expense.
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I love meritocracy, capitalism, and marketplace dynamics more than I like my own vested interest.
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And you were born in a communist country.
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And that to me is fucking ironic, huh?
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Yeah, yeah.
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And honestly, these are the contradictions that confuse people about me, but these are my truths and they will play out over the next 50 years to solidify my place wherever I deserve to be in the entrepreneurial lexicon.
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How do you keep the competitive instinct from affecting your personal and your familial relationships?
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Because you could drive your family and friends nuts trying to compete with them all the time.
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Do you turn it off?
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Do you curb it somehow?
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Yeah, I mean, I m competitive.
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I mean, me and AJ got into a fight, like a real fight over Scattergories six years ago.
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I m very competitive with my dad.
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I m very competitive with my brother.
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I m competitive with everybody, yes, but I definitely act differently in human world than I do when I put on my jersey every day, which is business world, you know?
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Yeah, okay, I can see that.
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It s better to get in a fight over Scattergories than it is over what you re gonna do with your employee pension plan or something that could break the ship.
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Me and AJ have built a $100 million revenue business in five minutes and have had bigger fights on the basketball court and on the board game court than any day remotely on business.
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It makes sense that you galvanize to be on the same team when it actually counts and the competitive brotherly kind of BS comes out on the driveway.
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Yeah, and by the way, we re on the other side of each other in that scenario, but in VaynerMedia we re on the same team.
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Right, exactly.
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You talk in the book about plan A, plan B. When I was a lawyer, Art of Charm was my plan A, but I always had this plan B of being a lawyer for a bit longer, but I think it really was like, that was kind of like what I told my parents, right?
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But I knew I would never go back.
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But I m wondering, if you have a plan B, does that mean at some level you re setting yourself up for failure?
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Should you never have a plan B because you re super confident in plan A?
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I m a big fan of plan B, plan C, plan D. And people are always mad at me for that.
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They re like, no Gary, there s that quote.
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If you have a plan B, you re set up for failure.
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I m like, no, if you have a plan B, you re set up for practicality.
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Like if you truly don t have a plan B, like if you truly don t,
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Well, that can get really dangerous.
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That can get into suicide.
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That can get into divorce.
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That can get into losing your family.
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That can get into depression.
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My current plan B is the Gary Vee brand, not Gary Vaynerchuk, the entrepreneur and operator, right?
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Like I would tell you why I m doing this book maybe more than anything deep, deep, deep down is it s my plan B. My plan B is that I talk about burning out as an operator, what I did, how I built a hundred million dollar businesses.
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Why did I stop?
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Because either I failed or I got burnt out, but I have enough of an audience where, you know, maybe I talk about work life balance or I obviously have started taking care of my health, but I always thought that that could be a cliche thing four years ago.
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That s probably why I started getting serious about it.
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When I started having thoughts,
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that I would have a heart attack at 46, and then that would be where my plan B would kick in, and that s what I would talk about, which is, hey, all the success in the world isn t worth your health.
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Here are the things I did.
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I was like, wait a minute.
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I m foreshadowing.
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Let s get serious about my health.
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I mean, it s unbelievable.
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Right this second, as I m talking to you, I m in the best shape of my life.
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You can tell.
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You look good, by the way.
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I appreciate it, and it s crazy.
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I see it a lot because I m producing so much video content, and they re doing a bunch of mashups,
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I was like, damn, I didn t think I looked bad.
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I have a small frame, I wasn t obviously overweight, my weight was proportioned, but I mean, I look way different than I did 24 months ago, you know?
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And so, and I feel different, and it s great.
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Anyway, I don t wanna get off to a tangent, we don t have a lot of time, I wanna get some more info in here.
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Plan B is the Gary Vee brand.
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I can make three to five million dollars a year speaking if I had to, even with a loss on my resume.
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Yes, how do we balance the hunger required to achieve plan A while not taking too much comfort in plan B?
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by, again, it s emotional intelligence, Jordan, by knowing that s the case.
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I know deep down I have that plan B, but it s always plan A or bust.
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So it s like having it, but not relying on it.
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Right, because I think a lot of people fail because they do 50-50, they do 80-20 even, and there s heat energy being sort of tossed out, lost in the equation.
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I have a million dollars in a bank account that I make pretend doesn t exist.
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Just in case?
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That s like my version of what you just asked.
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I know it s there.
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I like literally had to recall it right now.
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It s the first time I ve thought about it in 11 months.
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What do you think separates the people who take your information and act on it versus people who simply find motivation in it?
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I think the real talent gene of both work ethic, desire, and the capability to actually pull it off.
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I think the people that listen to me and will never do anything about it, use me as a comfort and escapism like people use television or sports or music.
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And I think that s great and I m happy about that.
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And I actually think it provides value.
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I think for a lot of people, see, this is where everybody is half glass empty and I m half glass full.
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Let me explain.
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I think those people, a lot of people in my world, you know who I m talking about, the 50 people that if they got together and talked about it, would say, ugh, those people, right?
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I don t.
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I yell at them sometimes.
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I go, you re such an asshole.
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Do you understand how much value you re bringing to that person?
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You re their Tonight Show.
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You re their Zelda.
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You re their New York Jets.
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You re their Leonardo DiCaprio.
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You re their run DMC.
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When they re consuming you, they don t have to think about what they re in tune to, which is shit, I m not gonna pull this off, and I m not happy about it.
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You re their escapism, and you re providing them real value, because life is hard and complicated, and for those 30 minutes,
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during the Ask Gary Vee Show, or Daily Vee, or the Hour of the Jordan podcast.
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You re providing them comfort and value, and that s very powerful.
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And then for a smaller group, you re laying the motivation and the blueprint that they re gonna go out and change their life.
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You draw the distinction between being a student and being a practitioner.
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What is the difference, in your opinion, between those two things?
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The 99% of shit that everybody in social media and marketing and branding and content say every day on social media that I read and I laugh, including some of the biggest names in the game, because they actually have never used a Snapchat geofilter.
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They ve never run hundreds of thousands, if not millions of dollars, if not tens of thousands of dollars in Facebook ads, yet they have very strong opinions about Facebook advertising.
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The people that write articles for Forbes or Fortune or HuffPo
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are a contradiction to the common conversation just to grab the headline, yet their logic makes no sense and it proves they never used Periscope or Facebook Live or a Twitter geo-ad.
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It s the difference between all the things I ve been saying about Snapchat and the 50 hucksters that have been following me very carefully packaged up all my quotes and headlines and a couple of others and now sell a $300 e-book on how to use Snapchat.
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So there s no reading this stuff, only doing is what it sounds like you re saying.
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You know, like everything else in the world.
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You know, the way every athlete looks at every non-athlete when they have an opinion about it.
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I mean, I ve become very friendly with a lot of athletes, because athletes now care about investing and care about personal brands on social media, so I ve been in a sweet spot.
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And as you can imagine, for a lot of people that are turned off by me, an enormous amount of kids that grew up in the ghetto and had nothing and became athletes, they love my business communication style versus others.
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I ve made a lot of friends in that world and it is stunning.
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I would have never thought as a Monday morning quarterback, the level of like utter, not disdain, but like just pure and utter, like they laugh at any of us that talk about stuff because we have no clue the seven days a week getting prepared for a sporting event on Sunday or
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the grind of an MBA schedule, or what your life is like since you re the age of nine and being prepped to be a world-class athlete, and they re right.
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I ve become so awakened by my own experiences in entrepreneurship.
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Jordan, do you know how pumped I am about DailyVee?
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I do not know, but I can only guess.
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Like, do you know how satisfying it is for people that, like, you know very well, and I mean, like, your actual friends, who you have dinner with seven times a year, emailing you and saying, fuck, man, I thought I knew, but now that I think about it, that s right, we only see each other during these times, because you re fucking really working fucking six to midnight every day, aren t you?
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Like, I m like, yeah, man, what do you think?
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You think I was lying to you?
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Like, you think I was trying to sell you something because it made me feel better?
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What about your kids?
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You ve got these little kids and you re teaching them these different skills.
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Are you trying to push them in the way to become entrepreneurs?
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What are you doing, parent-wise, to get this rocking and rolling?
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Because I can t see you pushing your kids in the direction to go work for GM and the HR department.
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You d be stunned.
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This is another contradiction.
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I am gonna do exactly what my mom did for me and my dad.
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I m gonna support, I could care less how they re wired or what they decided to do.
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I m gonna support it in a way like you ve never seen before.
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Meaning, look, when you have a really successful father or mother, here s what happens.
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You look at that mountain and you say, I m gonna climb the shit out of that and I m gonna fucking prove the world wrong.
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For example, I would have been great with a dad that was a billionaire.
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because I would have become a trillionaire because I love adversity, right?
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Like I love that everybody would have thought daddy did it for me and daddy s better than me and I would have been like, fuck you, daddy, and the rest of the world because that s who I am, right?
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Well, yeah, we know that.
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But I think for my kids, they may do what 90% of kids do, which is they look at that mountain and they re like, fuck that.
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Or they look at that mountain and they feel guilty that they took private planes to the Super Bowl and they want to start a nonprofit or be an artist or bring other value to the world in a different way than business does.
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If my kids want to be a teacher, if my kids want to make statues in Iowa, if my kids want to be comedians, the only thing I won t let my kids do is spend daddy s money in a vain way that doesn t provide value to somebody else.
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But if they want to provide value to people in a way that means that they have to go work and be head of HR at GM because that s what makes them happy, or however they react to their reality, I will support them as long as they re good human beings.
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As long as they don t buy baby giraffes.
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That s right, man.
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As long as I understand why they bought the baby giraffe, you know?
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If they can trick me into saying, you know, dad, I m doing this because at the end I m gonna go, aha, see, this is all shit.
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If I know what they re doing is trying to provide value to something or somebody, I m in.
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If they re just,
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fucked with because of the wealth that they were surrounded by or the notoriety and they re starting to feel it a little bit because you know, the last 18 months for my brand have been pretty intense.
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SPEAKER_01
AskGaryVee and this DailyVee especially and Snapchat have changed the amount of people that come up to me in public.
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SPEAKER_01
I m now at one to three people a day versus one person every 30 days only 18 months ago, right?
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SPEAKER_01
Because I ve come back out the show and like my content has been on fucking fire for the last 18 months after being fairly quiet for three years, right?
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SPEAKER_01
Misha s noticing it, right?
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She sees people getting excited and taking a selfie.
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It s gonna be interesting, man, but what I can tell you is I m gonna support them 100%.
5
SPEAKER_00
Now, is it true that you play basketball with your son Xander in the living room and he cries when you pick up the ball because he knows you re gonna block him?
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Very good job.
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I m not sure where you picked that up.
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I know I ve talked about it a little bit.
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Xander has not scored a basket on me yet.
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He s two, by the way, three.
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He s three years old.
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I would say that Xander is minimally not gonna score for the next 10 years.
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SPEAKER_00
Why do you block your three-year-old son and living room basketball?
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You never let him score.
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SPEAKER_00
He cries.
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because like I did it for AJ and he s one person and Xander may go the other way, but for now, until I realized I have to stop, I realized with AJ at six or seven that I was doing the right thing, right?
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That it was getting him motivated.
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He was working on his left hand.
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He, he looked at adversity and decided to climb the mountain.
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If in five or six years or three years or two years, I see Xander dropping the ball and walking away,
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and like leaving, it means that he doesn t have that gene and then I will support him in a different way.
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But for now I don t know and this will be better if he wants to go that route.
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My prediction is one day he dunks on you and it s the most proud day of your and his life at that time.
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When AJ beat me on 101, maybe he was 17, 18, I don t know, 16, 19, I don t remember when, there was an incredible feeling.
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Listen, accomplishing something in a true environment is the greatest feeling of life, and that s why I love business.
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You know what I love about business?
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For example, all these hucksters that I keep innuendoing to, and these, again, just so everybody knows what I m talking about, we re littered right now with marketers and coaches and experts that are just not that.
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They re hacking.
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They re hacking the system.
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They re not going to win.
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We ve seen these guys and gals forever.
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And yes, understand what winning is.
6
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Winning doesn t come just in the form of money.
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For example, everybody old cares way more about how they made their money versus how much they made.
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That s a good point.
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I have noticed that.
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I never really thought about it.
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And so I spent a lot of time with old people, and I did in my early 20s, and I ve stopped, because I think I got what I needed.
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SPEAKER_00
I really wanted to understand that the way people that lived it, what did they think about?
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They thought about family time.
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They didn t care about money.
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They cared about being respected.
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They cared about the legacy they were leaving.
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SPEAKER_00
And these were successful people, and just like old man McGee that was at my playground, you know, when I was a kid, who like worked at Johnson & Johnson for 50 years.
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You know, like, they cared about the right stuff, the stuff that s noble.
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SPEAKER_00
And that s what I care about.
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Right now, they may be able to bang some hotter chicks.
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They may be able to make a couple more million bucks quicker, faster.
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I m going to beat them in the long term.
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Nobody even knows who they are in 10 years.
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More importantly, they re going to have children who are going to be embarrassed about how their dad made their money.
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SPEAKER_00
Do you know how many wives I know right now that have husbands in, whether it s MLM or did something shady or da-da-da-da, who literally don t tell other, like I see them in settings, there ll be a business networking thing.
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SPEAKER_00
I watch these things.
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SPEAKER_00
This is how I m weird.
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I ll be talking to you, Jordan, at some business event, and I ll be going through the motions, but I ll actually be paying attention to the conversation to the left of us, which is two wives, and one of the wives will say to the other wife, oh, what does your husband do?
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SPEAKER_00
And I know the husband very well, I know exactly how he made his money, not good, and I see the answer from the woman, and it s fucking embarrassment.
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SPEAKER_00
And there s nothing worse.
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SPEAKER_00
You can t be that guy.
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SPEAKER_00
I can t be that guy.
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And other people can.
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They re wired differently.
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Mazel Tov, do your thing.
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SPEAKER_00
I don t judge you.
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SPEAKER_00
I don t.
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SPEAKER_00
I do not judge you.
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SPEAKER_00
However, when you try to tell the young and impressionable or the old and desperate that this is the way to do it, fuck you.
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That s why I m loud now and that s why I ll go on the offense.
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SPEAKER_00
I won t throw you under the bus.
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I don t win.
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by chopping down other people s trees.
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I m just gonna build the biggest tree, and everybody s gonna be like, look at that tree, and I m gonna show them the right way to do it.
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Legacy is greater than currency.
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Forever, homie.
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You talk about playing in the white space, working around the system, not within the system.
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What is the white space, and how do we find it?
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That s tough.
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So, I think the white space right now for me, clearly, this 55 minutes and 46 seconds, I know you edited, so I don t know exactly what time it is,
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My current white space is I m gonna be the purest bread, most honest, most noble entrepreneur in a world where I think we have the emergence of huckster entrepreneurs.
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That s my white space right now.
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This interview is literally my white space.
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I m gonna write a $19 book that gives so much value, not because I just wanted to crank out a book, but I want to guilt everybody else into making better books for everybody because they re like, shit, AskGaryVee was so good.
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I want everybody who s writing a business book that s coming out this fall, next winter, next year,
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to read this and be like, shit, and make a better book, because it s better for the market, you know?
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Yeah, I do know, and I agree with raising the bar.
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The other way to find the white space is pay attention to what everybody s reacting to, and become unbelievably cynical to it.
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What does that mean?
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It means if everybody s like, it s all about Snapchat, and I m saying that, well then become cynical to it.
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When you become cynical, you ve gotta also be open to being right or wrong, right?
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You can t be blindly cynical.
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So you gotta poke.
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Kind of what you did with me, Jordan.
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You poked, and then eventually you said, okay, this is real, and you ll poke the next person.
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Poke what everybody s doing.
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Live streaming s the best.
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Okay, poke.
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That means use it.
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That means watch 50 people use it.
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Come up with your own opinion.
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Not because I say so.
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Not because everybody says so.
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Right?
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Yeah, right.
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So basically, try it out.
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Yeah, poke.
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Taste.
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Taste.
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Taste.
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You know, like, cronuts are delicious.
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Well, don t just say they re delicious because everybody s talking about them.
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Go eat one.
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Not too many cronuts, but try a couple.
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Correct.
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Alright.
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I ll give you a good one.
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I will never meditate, and meditation s about to become huge.
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Yeah, absolutely.
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Meditation s gonna become coffee and soul cycle in America in the next five years, and I ll never do it, because I m scared it s gonna fuck with my brain, and I feel like my brain s perfect.
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So even though everybody says it s great, and everybody says I need to, and everybody says it s the best thing that ever happened to them, I know myself, so why would I just follow it?
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So I m gonna use the white space.
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If it ain t broke, don t fix it.
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That s what I m hearing right now.
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That s for sure.
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You have contact with tons of younger entrepreneurs.
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What s the difference between the way young entrepreneurs in their 20s and the older guys, and I put that in air quotes, in their 30s and 40s do business?
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What are the differences and what can we learn from each other?
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your gift is your curse.
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20 year old entrepreneurs think anything s possible and then they become overconfident and get caught by mistakes.
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It s also their gift.
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30 to 40 year old people tend to be more practical.
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They ve learned from their strengths and their mistakes.
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and they don t take as big of risks.
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So every day, I m pulling in opposite directions of being 20 and 40.
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I try to keep challenging myself and do random crazy shit, like a daily vlog, or like, who the fuck knows, opening a Europe office, or just keep challenging myself in the offense, but I ve learned from my other mistakes, you can t do everything, you need to empower people, da-da-da-da-da-da-da.
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And so, it s really a funny contradiction.
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The strength is the weakness, which is
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Blind naivete and faith and bravado and optimism, and that can catch you.
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I also do think there s a lot of fake entrepreneurs right now because there s an entitlement that if you re in your 20s, you should be an entrepreneur because of Shark Tank, because of the Social Network movie, because of this rock star status of entrepreneurship.
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So there s a couple more 20 year olds in the game now that should be number threes and fours instead of number ones, and that s a little bit of a difference as well.
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Most 40 year olds,
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or been selling blow pops since they were in high school.
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Yes, absolutely.
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And they ve seen a recession.
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Yes, which helps.
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A lot of younger people haven t.
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That s right.
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You mentioned earlier one of the best ways to go out of business is to make emotional decisions or get romantic about how you make your money or let your emotions get in the way of the task.
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What does that mean, to get romantic about how you make your money?
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And can you give us some examples of emotional decision making?
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I m glad you asked that question, I get to clarify it here.
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Being romantic about how you make money, this is how I define it.
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It means that if you re successful right this minute, look at the way you re making your revenue and understand somebody s gonna try to disrupt that.
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If you re at the top of your game, you know who should have invented Uber?
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Not Garrett Camp and Travis, the guy that owned the biggest cab fleet in the world.
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You know who should have invented Airbnb?
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The Starwood Group, not three entrepreneurs in San Francisco.
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You know who should ve invented winelibrary.com?
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Sam s in Chicago, or Zachy s, or Sherry Lehman s, or K&L, the biggest liquor stores at the time.
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So when you re at the height of your game, you need to understand that people are gonna disrupt you.
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You know how many people listening to you right now are making all their money on running quant affiliate arbitrage, Google AdWords affiliate marketing, other arbitrage ways, and it s mainly on desktop computer conversion, and the whole world s going mobile, and their numbers aren t as good as mobile, and they ve only got 24 months of this fruitfulness?
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I don t know the answer to that, but I assume you do.
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I have intuition, I don t have the exact answer, but I know a lot of people are making their money on conversion-based marketing when the marketing conversion base changes.
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Landing page optimization changes when it goes from desktop to mobile.
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Let s go back to emotional decisions.
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You mention that in the book as well, examples of emotional decisions.
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Can you give us an example of an emotional decision?
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I called a couple taxi guys and said Uber s coming and they said it ll never work.
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they could be doing a much better job.
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I can give you a million.
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I mean, podcasting is rolling right now, but here comes Anchor.
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Could that disrupt you?
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You should be on Anchor right now.
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I don t know, you need to constantly not believe in your own bullshit.
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Yeah, I agree with that.
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What do we do for the type of person who makes emotional decisions?
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Is there some way to stop ourselves from doing it?
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Is it a habit that can be cultivated or broken?
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I think that gets into a place where I don t understand.
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I think that goes to going to therapists, rewiring yourself.
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I don t understand that.
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I can just social commentate and give examples, and then everybody has to make their own decision.
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I will myself to victory.
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I just mentally got my place into over a six month period to fix my health that wasn t working for me for 38 years, but I can t sit here and be, I can t have the audacity to sit here and be like, hey everybody, mentally will yourself.
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Right, I mean, a lot of this is what we teach at AOC, habit cultivation, breaking bad habits, creating a self-awareness that allows you to make different decisions.
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But everybody does it differently.
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Everybody does, yeah, it s a bunch of, it s basically mental and emotional strength, and it s tough.
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It s like getting back in shape.
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This is awesome, I know you get a run.
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Jordan, I think this is the best interview you ve ever had.
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I think it s really damn good.
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I think the last one we did was pretty damn good, though, too, so it might be tied.
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All right, brother, stay well.
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Wow, this was a solid one.
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I mean, Gary s hard to keep up with, Jason.
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I mean, he is, I gotta hold my own with this guy, you know?
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You gotta shake and jive all the time, man.
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It s Gary Vee, come on, he s crushing it.
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It s jab, jab, jab, right hook, and I m trying to block, block, block, get a word in, but it s great.
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I love talking with him.
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He s very inspiring, but he s also got a lot of practical info that you can apply because that s how he rolls.
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He was railing on fake entrepreneurs these days.
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I don t blame him.
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I mean, there s a lot of that out there.
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It s unusual for people to be able to separate the BS from the gold, and Gary s always interested in the truth as well.
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Sometimes a little bit too much, I might even say.
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The man holds nothing back, that much we can agree on.
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If you enjoyed this one, don t forget to thank Gary on Twitter.
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We ll have that linked in the show notes as well as the other resources mentioned on the show, including the book, Ask Gary Vee, and the last interview that we did with him earlier last year in 2015.
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You can tap our album art and most mobile podcast players to see the cheat sheet for this episode, and we ll link to the show notes directly on your phone.
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I m also on Twitter.
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A lot of stuff never makes it to the show.
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Articles, insights, and I engage with everybody who messages me there.
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I m at theartofcharm on Twitter.
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You ll also find all of our amazing sponsors in the show notes or go to theartofcharm.com slash advertisers.
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Boot camp details for our live programs.
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Also at The Art of Charm, subscribe and review on iTunes.
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iPhone and Android apps available.
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This episode of The Art of Charm podcast was produced by Jason DeFilippo.
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Jason Sanderson is our audio engineer and editor.
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Show notes on the website are by Robert Fogerty.
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I m your host, Jordan Harbinger.
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Go ahead, tell your friends, because the greatest compliment you can give us is a referral to someone else, either in person or shared on the web.
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Now have a great week, and leave everything and everyone better than you found them.
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Alright, see you next time.
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Thanks for listening to The Art of Charm.
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Get more confidence, relationship skills, life hacks, and more at theartofcharmpodcast.com.