595 Gary Vaynerchuk: Insecurity, Fame, and Crushing It in Business

NO ENTREPRENEUR CAN BE SUCCESSFUL WITH SOMEONE WHO ISN'T INDEPENDENT As you know, it's important to continually grow (especially if you're an entrepreneur). I'm not excluded from that. Ten years ago I read a book by Gary Vaynerchuk that changed the course of my life. On this episode of the School of Greatness, Gary returns to the show for his third time. He gives me advice for my next ten years but also gives you invaluable advice on so many topics that you won't hear anywhere else. Gary is known for his unapologetic truth-telling attitude. He says a lot of things on social media that people may feel are harsh or extreme. But when we were talking, Gary revealed he actually cares deeply about what people think about him. And that's why he's so committed to serving people with hard-earned business wisdom in the long run. He explains why teenage nerds are winning right now, how hitting the big lists isn't what matters in business, and why you need an independent person in a romantic relationship. If you aren't familiar with Gary, you're missing out. Gary is a serial entrepreneur and the CEO and co-founder of VaynerMedia, a full-service digital agency servicing Fortune 500 clients. Gary rose to prominence in the late 90's after establishing one of the first e-commerce wine sites, WineLibrary, helping his father grow the family business from 4 to 60MM in sales. Gary is also one of the most sought-after public speakers alive today. He is a venture capitalist, 4-time New York Times bestselling author, and an early investor in companies such as Twitter, Tumblr, Venmo, and Uber. You'll learn everything you need to know about how to become the best of the best, on Episode 595. Some questions I ask: How are you affected emotionally when you see yourself aging? (9:32) Did business get better for you when you got married and started having kids? (16:52) When you started having kids did your obsession for business stay the same? (22:31) Why are you doing things you don't like when you have options not to? (24:51) When are the moments that you doubt yourself the most? (26:09) What's your insecurity? (33:45) What do you think you need to take you to the next level? (38:00) What advice would you have for me over the next 10 years? (51:52) In the episode you will learn: The results you should be concentrating on in business (14:02) The biggest challenge Gary's faced since starting Vayner (23:13) Best way to actually build your Instagram following (30:21) Why Gary hates being disliked (34:20) When relationships are really made (42:41) Plus much more... Get more from Lewis! Get my New York Times Bestselling book, Make Money Easy! Get The Greatness Mindset audiobook on SpotifyText Lewis AIYouTubeInstagramWebsiteTiktokFacebookX

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Lewis Howes?

  This is episode number 595 with New York Times bestselling author Gary Vaynerchuk.

• 0:08Lewis Howes?

  Welcome to the School of Greatness. My name is Lewis Howes, a former pro athlete turned lifestyle entrepreneur. And each week we bring you an inspiring person or message to help you discover how to unlock your inner greatness. Thanks for spending some time with me today. Now let the class begin.

• 0:33Lewis Howes?

  Ralph Waldo Emerson said, "To be yourself in a world that is constantly trying to make you into something else is the greatest accomplishment." Welcome to this special episode and interview with none other than Gary Vaynerchuk. And if you don't know who he is, you're probably not on social media because he is everywhere. He's a serial entrepreneur and the CEO and co-founder of VaynerMedia, a full-service digital agency servicing Fortune 500 clients across the company's four locations. He appears with Gwyneth Paltrow, Jessica Alba, and Will I Am on Apple's first original series, Planet of the Apps.

• 1:15Lewis Howes?

  He's also one of the most sought-after public speakers alive today. He's a venture capitalist and four times New York Times bestselling author and an early investor in companies such as Twitter, Tumblr, Vimeo, and Uber. Gary is currently the subject of Daily V, which is an online documentary series highlighting what it's like to be a CEO and a public figure in today's digital world. He's also the host of #AskGaryVee, which is a business and advice Q&A show online. And he's got a brand new book out that is literally crushing it, and it is called Crushing It: How Great Entrepreneurs Build Business and Influence, and How You Can Too.

• 1:58Lewis Howes?

  It is out right now, and I'm actually one of the featured subjects in the book. So make sure to go get a few copies of the book right now while you're listening to this, and you'll see. Full section about me from about 10 years ago, meeting Gary, reading his other book, Crush It, and the lessons that I learned and applied from that to how it impacted my business over the last decade. So definitely check that out. Get the book, Crushing It. And what we cover in this one, now Gary talks about a lot of different content, right? He's always out there. He's on a bunch of interviews, speaking on stages. He's got tons of content that you can listen to. So as you know, I always try to get people

• 2:39Lewis Howes?

  to share things that they never share anywhere else. And I think we were able to do that today. It's hard to do that with Gary because he talks a lot about everything, but I try to ask the questions that no one's willing to ask. And some of the things we cover are why the teenage nerds are winning right now, in Gary's opinion. Also, why hitting the big lists and getting verified is not what is important online and in business. Also, why having an independent romantic partner is essential for an entrepreneur. And Gary's take on his romantic relationship and business. And what Gary is actually terrified of the

• 3:22Lewis Howes?

  most in his life. And the advice Gary gave me about the next 10 years of what I should be doing in my business, kind of taking it full circle from 10 years ago, reading his first book, to now what he thinks I should be doing for the next 10 years. I am very excited about this. Again, make sure to screenshot this, tag me and at Gary Vee on Instagram, and the link is lewishouse.com/595 if you want to share the link out and watch the full video interview and all the stuff we talk about at the show notes. Before we dive in, I want to give a shout out to the fan of the week. And this is over on iTunes. We get reviews every single day. If you haven't left a review yet, make sure to leave one

• 4:03Lewis Howes?

  right now for your chance to be shouted out as the fan of the week. This is from Mike25, who said, "Anybody not listening to this podcast is crazy. The podcast is easy to listen to and keeps your interest." The interview Lewis has with special guests is both spiritual informational and especially motivating. Please consider this podcast. You will not be disappointed. Great job, Lewis. So thank you, Mike 25. You are the fan of the week. And again, head over to iTunes or just on your podcast app right now on your phone. You can go there and leave a review for your chance to be shouted out as well. All right, guys, get ready for this one. This is the big one. Gary Vaynerchuk, the one and only, and I hope you enjoy the episode.

• 4:53Lewis Howes?

  Welcome back everyone to the School of Greatness Podcast. Very excited about our guest today, the legendary Gary Vaynerchuk in the house.

• 5:01Gary Vaynerchuk?

  Hey, brother.

• 5:01Lewis Howes?

  Good to see you, man.

• 5:02Gary Vaynerchuk?

  Great to see you.

• 5:02Lewis Howes?

  As always, I think this is

• 5:03Gary Vaynerchuk?

  Fun to be back.

• 5:04Lewis Howes?

  This is the third time you'll be on the show.

• 5:06Gary Vaynerchuk?

  The second time here.

• 5:07Lewis Howes?

  Second time here.

• 5:08Gary Vaynerchuk?

  First time I was in my bedroom, I remember because I just remember it.

• 5:11Lewis Howes?

  Yeah, I think I've interviewed probably a bunch of times. One time over Skype, you were like in an airport lobby for like one of your books, like

• 5:19Gary Vaynerchuk?

  You want to hear something funny? I've been thinking about doing some recall content from Crush It for the Crushing It content in February, and I searched on YouTube Crush It and my name. In my preview pane, it's your review. I think I tweeted it to you.

• 5:34Lewis Howes?

  You shared out the video.

• 5:35Gary Vaynerchuk?

  Yeah.

• 5:35Lewis Howes?

  From Crush It.

• 5:36Gary Vaynerchuk?

  Your review of Crush It.

• 5:37Lewis Howes?

  Eight years ago. That's great.

• 5:38Gary Vaynerchuk?

  Dude, you haven't aged, which is weird.

• 5:41Lewis Howes?

  Really?

• 5:41Gary Vaynerchuk?

  Yeah, I don't know if anybody who's listening to this show right now thinks this is weird the way I do, which is that Lewis is always good looking and all that. But like, forget about good looking or like fit, he's got all those things down. I just mean actually aging.

• 5:55Lewis Howes?

  That's good. I've been told I have good skin. I don't know what that means, but

• 5:59Gary Vaynerchuk?

  But you also agree with me that you haven't aged that much yet in these eight years. How old are you?

• 6:06Lewis Howes?

  Thirty-four.

• 6:06Gary Vaynerchuk?

  Okay, good. That makes sense because I didn't age too much from 26 to 34 either.

• 6:10Lewis Howes?

  And then you started to

• 6:11Gary Vaynerchuk?

  Then I fell apart.

• 6:12Lewis Howes?

  Well, that's when you started investing yourself and you realized the importance of health.

• 6:15Gary Vaynerchuk?

  Oh, I, yes, yes. But I mean, besides losing fat and getting, starting to get some semblance of a muscle, but like gray hair and like losing my hair in the back, like just wrinkled, like actual age.

• 6:25Lewis Howes?

  How does that affect you emotionally when you see the aging of the hair or the skin or the wrinkles?

• 6:30Gary Vaynerchuk?

  Not much, actually. You know, it's weird, like I'm pretty vain and like all that stuff, like I'm into that. Like I, it should affect me more. Here's the punchline, it's like What the fuck are you gonna do about it?

• 6:40Lewis Howes?

  Right.

• 6:41Gary Vaynerchuk?

  Like, I guess I can debate hair implants, which, once in a weird moon, like, when I see, like, an angle from, like, a Babbin video or D-Rock, like, I'm like, oh shit, my hair's going... Like, I've got 18 to 36 months before I have to shave my head. Like, it's just going enough back here. But then I'm always like, or should I, like, get an Afro? Like, should I just get, like, a huge implant, like, situation like Matthew McConaughey or whatever? I'm sure he did something. Like, or like Jeremy Piven. Like, you look at the old... Or Elon Musk. Like, you look at some of that content, you're like, mm-mm.

• 7:09Lewis Howes?

  There's something.

• 7:10Gary Vaynerchuk?

  Elon, you didn't just magically grow hair, like...

• 7:12Lewis Howes?

  Exactly.

• 7:13Gary Vaynerchuk?

  So, I mean, so if anybody's listening who does that shit really well, I could be sold. I could, you know, looking at Nick's hair, like, I could rock some long hair.

• 7:20Lewis Howes?

  Right, right, exactly.

• 7:21Gary Vaynerchuk?

  One last rodeo before I'm finished.

• 7:23Lewis Howes?

  Does any of that affect you, though, in terms of, like, your confidence in business?

• 7:26Gary Vaynerchuk?

  No, no. Not in... You know, that's what's so great about business. I'm not an Instagram model, I'm not an actor, I'm not looked at or liked, or my, you know, return on investment has nothing to do with my physical appearance. So, what's great about being a business person, it's a mind game and an execution game. I also think that's why a lot of entrepreneurs and business people don't maybe take care of themselves as much as they should and things of that nature. No, I think it's more of just like being a guy or being somebody that's transitioning into their early 40s and you kind of know what the next chapters look like. You know, I think you think about it much more from like, oh, I'm getting older or like mortality. I don't feel less confident because of my physical... Because I never also, unlike you,

• 8:11Gary Vaynerchuk?

  who's like a physical specimen, there was never a time in my life that I ever, like, looked at my looks or physical status as a self-esteem builder.

• 8:19Lewis Howes?

  Right. You looked at results in your business.

• 8:21Gary Vaynerchuk?

  Yeah, to me, I was cool, even though nobody else thought I was cool, because I made $4,000 selling 8,000 Ken Griffey Jr. rookie cards this weekend in the Phillipsburg Mall. And so for me... It's interesting, I had so much self-esteem around business results when that was not a thing. Now that's a thing. It's really interesting to get these DMs. I love the 15-year-old guys that slide into my DM and telling me stories of like, why they look up to me because it really is actually very funny. The entrepreneur is cool now. You know, when you're a 15-year-old guy, you want a girlfriend. You want to be popular and like, I look at their photos and these are not like 15-year-old Louis's. These are like some nerdy-ass kids, but they've got like ridiculously like cool girlfriends. And I'm like, oh, this entrepreneur thing has really hit high school. Like this is real now.

• 9:06Gary Vaynerchuk?

  Like, wow, if you're a cryptocurrency millionaire, like, you know, as a kid, like, it's really fun for me that the thing I love the most, entrepreneurship, has become cool. I know that somebody who's listening to me who's over 40 and loves entrepreneurship the way I do, they also know what I'm saying and that anybody under 30 has no idea of how I'm actually describing it. And then there's that middle, 30 to 40, which is in between. But if you're over 40, you know that when you were in high school, being a businessman or woman had zero street cred. Zero. 0.00.

• 9:41Lewis Howes?

  Right.

• 9:42Gary Vaynerchuk?

  Zero. For the kids that are listening, I know there's a lot, like being an awesome violinist right now, that's not gonna necessarily crush it in the halls of like Draymond High. That was equally the same thing that I was going through, which was nobody gave up that I was making $10,000 like at a flea market in a weekend. That meant zero status. Like having like a starter jacket.

• 10:05Lewis Howes?

  Or the music you were listening to or the jeans you were wearing.

• 10:08Gary Vaynerchuk?

  Correct. Or like scoring 13 for the team that night. Or being in a band, like, you know, the cliche move like all the guys did. Like, there was 97 or being good at skateboarding. Like, there was 9,000 other things. And it's crazy to think, right? Because money has always been the cliche thing, like, you know, that has helped like some people close the gap of coolness.

• 10:27Lewis Howes?

  But not in high school.

• 10:28Gary Vaynerchuk?

  Not in high school and definitely not in 1990 to 1994.

• 10:31Lewis Howes?

  Now, if you have 50,000 followers on Instagram in high school, you're like the hottest thing.

• 10:35Gary Vaynerchuk?

  Or, I mean, like, talk about like society wrapped up in vanity, like of social. If you are a high school guy who's a nerd, but you get a blue check from Instagram, your life changed.

• 10:47Lewis Howes?

  Changed. You get any girl you want.

• 10:50Gary Vaynerchuk?

  The amount of people that send me things like, "I will rip my arm off if you can help me get verified on Instagram." Like, literally things like, "I will sell you my children." If you get me verified on, give you my home.

• 11:03Lewis Howes?

  It's crazy.

• 11:03Gary Vaynerchuk?

  And live in a cardboard box. And I'm just like, this is the saddest shit ever. A lot of my content in the last six months has been like, please do not get wrapped up in likes. And, you know, your rank in the podcast list or checks. Like, that is such a death game. You will lose that game. You will start pandering to those results versus actual results.

• 11:25Lewis Howes?

  By creating a great product consistently.

• 11:27Gary Vaynerchuk?

  New York Times Bestseller List.

• 11:28Lewis Howes?

  Yeah.

• 11:29Gary Vaynerchuk?

  I don't pander to that. I don't want to hire the companies that get me on the list. I want to sell more books.

• 11:35Lewis Howes?

  Yeah.

• 11:36Gary Vaynerchuk?

  That's the KPI. Impact more people. That's even the bigger KPI. But, look, I mean, the world has always traded on. I mean, you know, do you know how sad at this point I am when I'm on these 30? No, I'm not 30, excuse me. Like, top 40 influencers or 50 under 50 now, which is the only thing I can.

• 11:54Lewis Howes?

  How old are you now, 40?

• 11:55Gary Vaynerchuk?

  42.

• 11:55Lewis Howes?

  Yeah.

• 11:56Gary Vaynerchuk?

  So, I hate it because my feed gets filled up with like, congratulations or the other people that are on it trying to get me into a conversation. Not because I, kudos to them because I was the most pumped too when I was like, 10 most important people in the wine business under 40. Like, amazing, I get it. As you get older, you realize how those awards or those, like, just completely arbitrary things of like, an editor liked one of your podcasts and decided. And we all get excited.

• 12:24Lewis Howes?

  Yeah.

• 12:24Gary Vaynerchuk?

  Six best podcasts to list in 2018. You want to be a part of that. You want awareness. Here's what I would say. We've overcorrected a lot of people into caring about that more than the actual results. And so, we care more about the facade than we care more about like, look how nice my room. Like, this, we're in a beautiful room right now, right? You've really done a nice job with this. I like how you put like, the more important people on their own, like, pick wall over here.

• 12:47Lewis Howes?

  Well, they were just bigger photos.

• 12:48Gary Vaynerchuk?

  No, no, no, no. You made them bigger. I know you. But, but here's what's interesting to me. What's interesting is if the concrete and steel under this building is shit, well, this whole thing falls. So it didn't matter that you put some like-

• 13:02Lewis Howes?

  How pretty it is, yeah.

• 13:03Gary Vaynerchuk?

  Exactly. And I think right now, too many entrepreneurs and personalities, and 98% of the people that are listening to this podcast right now, are caring about the decorations and the curtains and the painting in the room, not the steel and the concrete holding up the room. And I think that that's an important conversation to be had. And I think a lot of what makes me happy and work for me has been the steel and the concrete.

• 13:27Lewis Howes?

  When you were in high school, college, and in your twenties, and you were dating-

• 13:32Gary Vaynerchuk?

  Yes.

• 13:32Lewis Howes?

  I don't think you ever talked about this, and it just came up to me now. Were you driven by dating a lot of girls? Or were you trying to like impress them through the business you were building in the wine space? And did business get better for you when you got married and started having kids? Or did it hurt you? You know, did it help?

• 13:50Gary Vaynerchuk?

  That's a great question. I was so one-track minded in my twenties, in my fif- from 15 to 25, 15 to 27. From 15 to 27, in 12 prime years where a boy, then a young man, cares about dating and hooking up and having a girlfriend. The level of me giving a f- about that was stunningly low.

• 14:16Lewis Howes?

  Really? Did you have a bunch of girlfriends or no?

• 14:18Gary Vaynerchuk?

  In high school, not at all. In college, I had girlfriends. But from like my junior year of college until I got married, I pretty much always had a girlfriend except when we would break up and I would have a couple of months in between. But it was literally like because I almost weirdly thought I had to. When? Because, look, I mean, you'd like to have a companion, fine. But like, my business was more important than my girlfriend by a magnitude of a thousand to one in those four relationships I had, five relationships I had, in between my first serious girlfriend in college and marrying my wife. My wife is such an enabler of my entrepreneurship.

• 14:56Lewis Howes?

  She wants you to go out and do what you want, right?

• 14:58Gary Vaynerchuk?

  She came in eyes wide open and is so independent and wants to run the household and the kids the way she wants to. She wants to be

• 15:07Lewis Howes?

  That's her business.

• 15:08Gary Vaynerchuk?

  dictator and CEO of our home life that she likes that we're in a divide and conquer dynamic. Like Lizzie's aspiration is not to co-parent. She doesn't want my two cents. She'll take it once in a while, but she wants me supporting her on her vision and execution. And I have empathy for that because that's what I want on what I do for a living. And so we're a good pair. I think if you have somebody, no entrepreneur can be successful with somebody who is not independent. None. There's no entrepreneur. That's right. No Sally, if her husband Rick is not independent and can't keep himself busy and isn't about his life.

• 15:51Gary Vaynerchuk?

  She can't do what she needs to do because he's going to be pulling her at all times and making her feel guilty for taking that extra business trip, for looking at the phone during dinner. And so you need, if you're a true bred entrepreneur, an obsessed entrepreneur. And what I mean by that is, I believe, I know your audience, I know mine. I believe 87% of the people listening right now are in it for the money. They're in it for the short term, get the money, go on the nice vacations, right? Buy the nice car. If you're part of the 13% that I'm a part of, which is you would die tomorrow if somebody said you couldn't play. I would much rather make a hundred thousand dollars a year. And I proved this.

• 16:30Gary Vaynerchuk?

  This is what I did in my, from 22 to 34, I made 150, 130, 67, $49,000 a year, building my dad's business for him. I never got upset that I had no equity. I don't have resentment that I left that business at 34 with nothing. Even when people say to me, don't listen to Gary, his daddy put him on or gave him the business, when I know the true story is, I didn't get anything. I just built a monster business for my dad in my best years of my youth and then left and started over, right? I mean, VaynerMedia started with me getting a client to pay because I had no money to pay me and AJ or anybody else. I had no money.

• 17:07Lewis Howes?

  Yeah. I was there in the beginning. I went to your first office when it was four of you and a ping pong table.

• 17:12Gary Vaynerchuk?

  That's right. And you crushed me in ping pong. I was pissed. Louis is awfully good at sports. It really makes me upset.

• 17:19Lewis Howes?

  When you're a lonely kid your whole life and you have all day to just hit a ball against the wall.

• 17:23Gary Vaynerchuk?

  And you're shaped like an Adonis, yeah, that part too. Anyway, nonetheless, for the 13% who are listening, they get it, which is like, look, no question, I think a lot of people like bullshit if they don't know me, but if you know me, make 14 million dollars a year, right? And not be able to play anymore? Passive income. Make 200,000 a year and get able to play? I'm not even close. It's 200,000 to play. I'll suffocate. I'll suffocate. I'm like a fish out of water if I'm not building a business. Every moment of my life since 1987 has been unbelievably passionately, 98% of my human energy against the notion of either my family or building the business that's in my hands at the time.

• 18:07Gary Vaynerchuk?

  Baseball cards, liquor store, you know, my personal brand, VaynerMedia, the investments I've made, selling a book. I'm always in project mode, operating. You know, from the day I started working, I've been running a company. Becoming Gary Vee and all that stuff, there's never been a day where Gary Vee has been my business. Every day since May of 1998, I've been running Wine Library or VaynerMedia. All of them. Every single day in continuum. So, yeah, I mean, to me, if you're that, if you're one of those 13%, for all the 13% that are listening, if you're still not married, or by the way, if you're married, you may want to consider divorce. I'm being really serious here, because you're not doing yourself a favor and you're not doing your partner a favor. If you are not blindly supported, you will suffocate and die. It will not work.

• 18:52Gary Vaynerchuk?

  It just will not work. It's the same reason I give kids advice to tell them to go, their parents to go themselves when they want to tell them what to do in their twenties. Not because I'm like rogue or I'm trying to be popular or create a viral piece of content. It's because when they're 47, they're gonna hate their parents. And so if you're doing what your parents want you to do because you love them, you're just appeasing the short term because you're gonna end up having no relationship.

• 19:17Lewis Howes?

  When you started having kids,

• 19:19Gary Vaynerchuk?

  Yes.

• 19:19Lewis Howes?

  Did the obsession for business stay the same?

• 19:23Gary Vaynerchuk?

  No.

• 19:24Lewis Howes?

  Or did it increase?

• 19:25Gary Vaynerchuk?

  Probably.

• 19:26Lewis Howes?

  Or did it go down?

• 19:27Gary Vaynerchuk?

  It definitely didn't go down.

• 19:28Lewis Howes?

  Yeah. So the obsession has stayed the same since you were, whatever, 12, 13, 15, to getting married, to having kids, it stayed the same? Or has it gotten stronger?

• 19:36Gary Vaynerchuk?

  I think the greatest way to be selfless is to be selfish. I mean, I just don't care about political correctness, like what I'm supposed to be doing. I don't know what else to tell you. Like, I know who I am and I know how I can bring the most value to the 12 people I care the most about. And that means me being, day in and day out, second and second, happy. And that comes in the form of caring about my craft.

• 19:59Lewis Howes?

  Yeah, yeah. What's been the biggest challenge for you since starting Vayner and just the transition out of Wine Library? What's been the biggest thing you've had to overcome?

• 20:08Gary Vaynerchuk?

  It's been pretty damn good. I think, look, I think VaynerMedia and VaynerX, the holding company that owns Pure Wow and VaynerMedia and the other things I'm about to do, has been a pretty good run. I think the one thing that sucks is having clients. When I ran my dad's business, I was the boss. People were trying to sell wine to me to sell to other people. Thus, I had the leverage in the B2B environment. VaynerMedia, I'm the reverse. Chase is my client, Budweiser's my client. I'm on their time. And I'm fancy now. Like, I shouldn't be in a place in my career at 42 with my net worth and like all this stuff, where I'm at, where I'm like at the begging call and like have to be late for something that I don't want to be late for because a client's yelling at me about being mad about something. But I chose the profession and I have the humility in the prime of my career to be in it. So the biggest challenge is like,

• 20:54Gary Vaynerchuk?

  I'm over myself and I have the humility to run a client service business. I'd be lying if I didn't say like, when I'm dealing with something like that, I'm like, what the? You know, I'm like making fun of myself to myself. I'm like, you, like the fact like, when I have the anxiety that I have to call a client tomorrow for them to yell at me and say I suck shit, when they're a fucking idiot and I'm gonna be the greatest of all time? That's a little weird.

• 21:17Lewis Howes?

  Right.

• 21:17Gary Vaynerchuk?

  Like, you have that conversation with yourself of like, why am I savag-- like, what am I doing here? When I can make more money just being Gary Vee than I can running VaynerX and I'm dealing with seven meetings in a row where people are complaining about other people within the building and I'm like playing guidance counselor? I like that because I want to make people's lives better within my company. But there are days, and I eat shit for a living. But there are days where I'm like, why am I doing this when I have a million options not to? So then you start asking yourself.

• 21:45Lewis Howes?

  Why are you doing it?

• 21:46Gary Vaynerchuk?

  Because I think I'm holding my breath for the bigger win. I think that I'm gonna build the greatest communications holding company of all time. I think I'm gonna then buy brands. And I think I'm gonna run them through this machine, this Death Star. And I think I'm going to buy vans for $874 million one day. When it's on the downside, because right now it's not, it's in the prime spot. But again, when it's on the downside in seven years where none of the kids care, or people care. I'm gonna buy it and I'm gonna flip it for $4 billion. And it's gonna be because I ate shit for 20 years.

• 22:20Gary Vaynerchuk?

  My plan is to build a platform that is there for me to help Pencils of Promise, something we're both passionate about. Help Crohn's Disease with AJ. Help what takes my parents' lives. If you decide to run for governor of California in 30 years, help that. Whatever I'm passionate about. And also sell sneakers and hats and hoodies and books. And I needed to build this machine for myself for the rest of my life. And so I'm willing to eat shit right now to build it. Because it will make the 50 next years really exciting.

• 22:54Lewis Howes?

  When are the moments that you doubt yourself the most? Because I know you're extremely confident in yourself. But are there moments, what are they? And how do you get through it when you have that doubt in anything you're doing?

• 23:04Gary Vaynerchuk?

  One of the weird things I do is I'm in a funny place now where I'm not putting myself in a place where I doubt myself. And so I always wonder, is that like not challenging myself? Or is that like staying in my lane? But like, I will tell you, like, the only thing I think about being like, when you ask me like, what's scary? Here's, reading in public is scary.

• 23:23Lewis Howes?

  Terrifying.

• 23:23Gary Vaynerchuk?

  Because I can't read.

• 23:24Lewis Howes?

  Yeah.

• 23:25Gary Vaynerchuk?

  Even like, the last time I did the AskGaryVee book, like, for the audiobook.

• 23:28Lewis Howes?

  You just kind of riffed.

• 23:29Gary Vaynerchuk?

  Well, you know what's funny? I always do that.

• 23:30Lewis Howes?

  Yeah.

• 23:31Gary Vaynerchuk?

  Uh, because I get bored. Because that's why I got F. So I'm like, I don't want to read my own [BLEEP]. Like, you know, I'm like, [BLEEP] this, I know what's in here, like, you know? That's why people buy the book and the audiobook, because they're like, basically not even the same.

• 23:40Lewis Howes?

  Yeah.

• 23:41Gary Vaynerchuk?

  It was fun actually for me because I'm like, oh, I'm a better reader than, you know, I think I've been forced to read so much over the last 10 years as we became a computer-based, email-based, text-based world. But if you were like, hey, read my notes here right now to the podcast, I'd be like, you could literally ask me to get naked. I'm like, alright, okay. But if you said, "Read this," right now, verbatim, I'm like, eh, because I don't like that. But man, then it's things like, throw me in a pit of snakes. I'm like, I don't want that.

• 24:07Lewis Howes?

  Right.

• 24:07Gary Vaynerchuk?

  Like, jump off this building, [BLEEP] that.

• 24:09Lewis Howes?

  But there's nothing in business that makes you doubt yourself. Is there a situation that you could see, like you've spoken in front of 50,000 people? That's not scary.

• 24:17Gary Vaynerchuk?

  Well, at this point in my career, I've been in the room with everybody. And that means I have not been in a room with a ton of people, but like every step.

• 24:24Lewis Howes?

  All the big leaders, every billionaire, every CEO.

• 24:27Gary Vaynerchuk?

  I'm of the cloth. I belong.

• 24:29Lewis Howes?

  You're confident too, yeah.

• 24:30Gary Vaynerchuk?

  I'll be very frank with you. I think I'm better. I think when it's all said and done, I win this generation. I think Elon and Zucks and the Uber guys, I think a ton of people make more money. I'm convinced now that nobody will make more money, nobody will make more money and help people make more money than me in this generation. I will win.

• 24:49Lewis Howes?

  In that game, yeah.

• 24:50Gary Vaynerchuk?

  In the game that I like.

• 24:51Lewis Howes?

  Yes.

• 24:52Gary Vaynerchuk?

  Which is, winning personally and willing, helping other people. I don't think I'm going to be touched. I think I will be the guy. I think they will go back and be like, "Look, here were the people that were entrepreneurs during a time when entrepreneurship was cool. And here are all the different things. Elon invented the craziest shit. And, you know, Mark Zuckerberg created the greatest, and Bezos created the best companies and made the most money. And then Gary did the best job of making the most money and he bought the Jets and that became symbolic. But he also created millions of hundred thousand heirs and millionaires. That's what Crush It's About.

• 25:25Lewis Howes?

  Yeah.

• 25:25Gary Vaynerchuk?

  Like, that's why Crushing It's About. I think that's really cool. I spend an enormous amount of time trying to make my audience awesome, out of the selfishness of the legacy, not to get them into a top of the funnel to buy my book or my sneaker.

• 25:39Lewis Howes?

  Right, right.

• 25:40Gary Vaynerchuk?

  I ask for it, but I have zero vulnerability or expectation. You know, listen, you have a great business on Roundy Brand, a lot of other people do. I think that's great and think it's cool. I just like that I make my economics in other places, but I'm paying the price. I'm eating the shit. Like, one could argue what's better, but I absolutely. Think I'm gonna win the game as made most? Because it's keeping score. I mean, it's part of the equation. But I'm not driven by that. I'm driven by, look dude, you are crushing it. You are winning. You're doing so many great things. Do you know amazing? Like when I read, because you know, Stephanie Land, my ghostwriter interviewed you for it. And then I'm going through it. Just reading your story about the book Crush It.

• 26:25Gary Vaynerchuk?

  And then, of course, I remember like getting picked up and going to the Cost Plus and all that.

• 26:27Lewis Howes?

  I picked you up in like a beater car, you know, and just like no money.

• 26:31Gary Vaynerchuk?

  But it's fun, right? Like, first of all, one thing I know is like, everybody's got it in them. It's not like I'm manufacturing. You were doing the LinkedIn party stuff. That's not Crush It. But, man, I have definitely suffocated excuses better than a lot of people. Which is really the biggest reason so many people who are listening right now are not winning. They are surrounded by people that are willing to accept their excuses on one very interesting insight. It's because those people don't give a fuck. Your friends and your family are letting you get away with your excuses because they don't care. I weirdly don't know you and I care. And let me tell you how to fix this. Get excuses out of your mouth. And so like, I think between that and then showing people this whole dollar 80 strategy. I don't know if you've seen this. This has been great for me.

• 27:14Gary Vaynerchuk?

  You know, once in a blue moon, I come up with very tangible advice. So I've been talking a lot about leaving comments in people's Instagram posts. But not like, follow me or like just to game it. No, take the out. You wanna grow your, everyone's like, how do I grow? I'm like, there's a way. It's called the thank you economy. Quietly go in like, nice and calmly. Like if you're a photographer, go to Nick's page. He's gonna legit shit. He takes a photo of some pretty person, boy or girl. He's very good at that. In some beautiful setting. And like, look at it. And then leave a comment that's meaningful. Like, hey Nick, you know, are you using this filter? Or I noticed what you did with the light there. Like something that means something, not like, cool, fucking lit. You know, like you're not leaving the comment for the sake of leaking the comment. You're taking the actual hour and a half to like, look, add something of value.

• 28:00Gary Vaynerchuk?

  You do that on 90 different, the way I came up with it was, leave your two cents, you know, in a comment. Leaving your two cents. Go take nine hashtags that are relevant to your business. And then go to 10 accounts or 10 hashtags, top nine. It used to be the top now. Now it's just random nine.

• 28:17Lewis Howes?

  Yeah.

• 28:18Gary Vaynerchuk?

  So pick 10 hashtags, the random nine, that's 90. Leave two cents. Now you've left a dollar eighty for the day.

• 28:25Lewis Howes?

  Yeah.

• 28:26Gary Vaynerchuk?

  Watching the last two, three, four, five, six weeks of people like, you know, because it's funny, right? People are buying [BLEEP] likes and comments. People are like trying to do dumb shit, give away iPads, or Yeezys, or Off-Whites to get followers, or you can actually work for an hour.

• 28:41Lewis Howes?

  At value.

• 28:42Gary Vaynerchuk?

  Know your craft, and that like Nick for, I'm actually looking at it like, do you know what would happen, because he actually knows his craft, if he actually spent three hours a day, three hours is a lot of time.

• 28:51Lewis Howes?

  It's a lot of time, yeah.

• 28:52Gary Vaynerchuk?

  And if he gave a [BLEEP], I don't think he should or shouldn't.

• 28:54Lewis Howes?

  Right.

• 28:55Gary Vaynerchuk?

  But if he gave a [BLEEP], the fact that if he spent three hours looking at twenty hashtags and photography, because he's crafted and skilled and gifted, and went to those people's photos and said shit that I would never understand, I'd just be like, "Nice thong," or like, "Nice muscles," or like, "Cool coconuts." Like, if he said like, "Oh shit, I see what you did there off [BLEEP] reflection horizon," you know.

• 29:17Lewis Howes?

  Right.

• 29:18Gary Vaynerchuk?

  Well, that matters, because like people see that you're leaving something meaningful, right?

• 29:23Lewis Howes?

  Mm-hmm.

• 29:24Gary Vaynerchuk?

  I don't even remember why [BLEEP] I'm talking about that. Basically, I'm thinking about bringing the most value. I think it's mindset and strategy. I used to not like the motivational version of me. I've gotten much more comfortable in the last eighteen months, because I'm like, huh. If I didn't think of it as motivational, and I thought of it as strategy. Because mindset's strategy, right? Like, being insecure is a mindset. It was put into you for a million different reasons. Figuring out how to get out of that hole, by who you surround with, how you think, what you do. Insecurity is the biggest poison in our lives. Like, insecurity scares the [BLEEP] out of me. Lack of self-esteem is why people do everything bad. Buy dumb shit to make themselves feel better.

• 30:07Gary Vaynerchuk?

  Do dumb shit, like take dumb shit and put it into their body. It's all insecurity. I still remember in high school, back to dating now, maybe I'm gonna tie these stories together. I remember when I realized, oh, my friends drink alcohol to get courage.

• 30:23Lewis Howes?

  Hmm.

• 30:24Gary Vaynerchuk?

  But they don't even that drunk, they just use it as an excuse to do shit that they wanted to do anyway. It's just all [BLEEP] insecurity, man.

• 30:32Lewis Howes?

  Yeah.

• 30:32Gary Vaynerchuk?

  I don't know.

• 30:33Lewis Howes?

  What's your insecurity?

• 30:35Gary Vaynerchuk?

  What is my insecurity? My insecurity is... This is gonna be very weird for a lot of people who don't know me. I hate being disliked. Which is a really funny insight because the way I act in public and in my content shows a huge willingness to be disliked. But I only think of it simply as, if you really break down my content and my ethos and who I am, I'm willing to be disliked in the micro. I'm willing for you to not like me because I'm suffocating you and you don't like that I've put you into a corner, but you're gonna love me in three years. I hate being disliked.

• 31:10Lewis Howes?

  Why?

• 31:11Gary Vaynerchuk?

  Because I think I should be nice and I think I like people. Like, I think it's a bad idea. I don't know if it's an insecurity, like... I don't know if you saw, like, I had Tim Ferriss on my podcast and I apologized to him at the end because in my early part of my career, I got on a tangent in one speech at Blogs With Balls where I was like, "Bleep, four hours of working, like, go all in," and it just... I didn't like the way it came out. I knew what my intent was, which is why I'm kinda fine, but I've been apologizing to Tim for a decade. Because I don't want Tim to-

• 31:41Lewis Howes?

  From that one speech?

• 31:42Gary Vaynerchuk?

  Yeah, because it hurts Tim's feelings, rightfully so. Like, if you go and find Blogs With Balls 2009, I went on a good three, four-minute tangent. I didn't talk about... I didn't... I've never read anything.

• 31:52Lewis Howes?

  Right.

• 31:53Gary Vaynerchuk?

  From what I know, four-hour work week is about efficiency, not about working four hours, so like... I just don't like being disliked. Like, I look at Ray Lewis on your wall, right? In the right circumstance, at a Jets-Ravens game, there is no question that Ray would never remember, and this didn't happen, but like, Tom Brady. Bleep, I hate Tom Brady, but do I? I hate him, right?

• 32:13Lewis Howes?

  But you love him, appreciate him.

• 32:14Gary Vaynerchuk?

  But I would hate... No, no, I don't even appreciate him. Bleep, I know how great he is. I have zero appreciation for him being great. None. I know it's there. I don't appreciate it.

• 32:22Lewis Howes?

  If he was on your team, you would.

• 32:23Gary Vaynerchuk?

  No shit. And I hate him and I say it in public, "Bleep you," and this and that, and at games, and if... Like, if he was on the sideline, I flat-out like, "Bleep you, you bleeping suck," like, mean it, right? But in like, kind of like in real life, like if I cross paths with him, and I feel like, you know what scares me now is I'm like, oh, I'm definitely gonna cross paths with like, the Kobes and Tom, like all these guys wanna be entrepreneurs and will be entrepreneurs. So I'm like, eh, the sports thing's weird now, like, I'm gonna see him at some like, you know, like, Alan and Co offsite, exactly, and I'm like, eh. I don't wanna be disliked because I think there's no reason to. I hate cynicism and hate. I hate it so much and being associated with it would really upset me.

• 33:05Gary Vaynerchuk?

  I'm insecure at, I don't know if insecure is the right word, but I am aware that I'm awfully peacocky onstage in a podcast. Like, you could ask me questions here and I could say shit that I believe,

• 33:21Lewis Howes?

  Right.

• 33:21Gary Vaynerchuk?

  but I don't wanna deal with the ramifications of my truth.

• 33:24Lewis Howes?

  Sure.

• 33:25Gary Vaynerchuk?

  And more importantly, and it's a great time to say it, and Babbin, I hope you're filming, there is something that's really interesting to me, which is, I really know that I mean nothing. I think the biggest reason I'm willing to spit authentic is because I don't think so highly of myself. Meaning, I'm not insecure, it's just that like, me thinking Nick is not good at something, like, business. Forget about photography where, who gives a ****. Me saying your business stinks, even with all my business things, I still think is just one dude's opinion. I understand it's a solid opinion, I understand that it comes with some heritage and value. Too many great people who've won so much in things have told me, I'm not gonna win, and then I've won,

• 34:08Gary Vaynerchuk?

  that I know I'm the same, and so I think one of the reasons I'm willing to spit is like, my opinion's still my opinion and like, take it with a grain of salt.

• 34:15Lewis Howes?

  Yeah, you talk a lot about, you know, delayed gratification, there's time, and everyone has a lot of time, and people are wanting things right now. What do you think, even with that mentality, I know that you would love to get results, bigger results all the time with what you're doing. You know, if you sell a hundred thousand books,

• 34:32Gary Vaynerchuk?

  Right.

• 34:32Lewis Howes?

  you would like to sell two hundred thousand books right now.

• 34:34Gary Vaynerchuk?

  That's exactly right. Micro, micro, macro.

• 34:37Lewis Howes?

  Yes, exactly.

• 34:38Gary Vaynerchuk?

  That's it.

• 34:38Lewis Howes?

  But what do you think?

• 34:41Lewis Howes?

  You're gonna need to do to step into getting faster results. In the micro and the macro. What would take you to the next level?

• 34:48Gary Vaynerchuk?

  I think what takes everybody to the next level is cutting out dumb shit. If you really look at anything, it's always cutting. So what, Jack Welsh had such a great career? He was so right in like, when it was a revolutionary thought of like, "Cut your bottom 10% of your staff each year." But it's right. I mean, like, no question, whether in your training, in your business, in your friendships. Do you understand that if every person who's listening right now started to weed off the friend that is bringing the least value? And I mean, they're a bad influence, they're bad mojo, they're bad. Like, not bad, I mean, they're just negative. They're a negative person, so they're dragging you down, they're selfish, they have bad habits, like a drug addiction or something. And you don't want to leave them.

• 35:31Gary Vaynerchuk?

  I want to make sure people, people when they hear me say this, like, "Oh, you can get rid of your friend." No. Just, if you audit your circle of who you spend time with, if you just spent less time with something that is broken, and you added one person that was incredibly valuable, your life would be a lot better. That's just real. And so I think the thing that would, the thing that I'm not good at, but I will never give it up, so I don't know if it's a strength or weakness, I do a lot of meetings on spec when people ask me to.

• 36:02Lewis Howes?

  Some of those pay off, long-term, and some of them you're just like, "Am I wasting my time?"

• 36:06Gary Vaynerchuk?

  Even this was back in the day, like, "Can I drive you to the Cost Plus?"

• 36:11Lewis Howes?

  Right, right.

• 36:12Gary Vaynerchuk?

  "I'm glad I did it, now we know each other for a long time."

• 36:14Lewis Howes?

  Yeah.

• 36:14Gary Vaynerchuk?

  Yeah, I mean, I think at this point, no question, my time has become remarkably valuable. And I still do, 20% of my time this year will be highly questionable in somebody was auditing my life. At some level, you gotta accept some of your humanity aspects, so... But I think that that is the thing that would take me to the next level, getting even more disciplined on every single thing I do, debating every single idea. I'll give you a good one, this is super funny. If Tyler was in the room right now, he would argue that I've made a mistake by being here today for an hour.

• 36:48Lewis Howes?

  Your assistant Tyler?

• 36:49Gary Vaynerchuk?

  We've got a lot of things going on. I'll break it down. This is gonna be interesting for people listening. We had a bunch of new business meetings, new people I could have met. Hi, big, good, would have been on your biggest wall. Right? And Tyler gave me a list of things. He's like, you can do one of these four things. And I did this. I would argue, somebody analyzing me would say, this is the wrong move. Couple of reasons. Number one, the new book Crushing It is selling so well that I'm not even trading for speaking or doing podcasts. I'm not, I mean, I've never been this passive two weeks away from a book release.

• 37:21Lewis Howes?

  Right.

• 37:23Gary Vaynerchuk?

  I don't even know what I'm doing. I'm like, I'm like, this is like, I'm weirded out myself. I almost like weirdly want it to collapse and everybody returns the pre-sales. So I get punched in the mouth for being so passive. This audience that is listening right now has heavy crossover. I've been on the show not too long ago. A lot of people that like you, like me, vice versa. So I get somebody analyzing, how do you get better? That this was the wrong choice for the hour. And I just like you.

• 37:48Lewis Howes?

  Yeah.

• 37:49Gary Vaynerchuk?

  I just wanted to see you. So like, I think that's a human thing. Like, sometimes you just have to do those things. But so that's why I say, I won't change what would make me better. But what would make me better is to analyze my time more fruitfully for micro results. But for macro results, friendship, whose funeral are you gonna show up to? And why? I think this is the better decision. And so I will always make a macro decision. And I will take, I will take 100% of the macro results. And only 60% of the micro results. And I think everybody who's listening, man, do I think 99% of the people are trying to maximize micro. Everything, person, like, I'm blown away by people literally analyzing like, what's in it for me?

• 38:34Gary Vaynerchuk?

  In this game, microsecond of this thing. Everybody, it's so awesome for me to watch, cuz I'm like, you've lost.

• 38:42Lewis Howes?

  Yeah.

• 38:42Gary Vaynerchuk?

  And people do that. And people do it when they don't mean shit. I love people getting put on just a little bit. And they think they're fancy and they just start valuing like.

• 38:50Lewis Howes?

  Right.

• 38:51Gary Vaynerchuk?

  Anyway, Babin, you're smiling because that's a big thing you've learned, right? That like, as somebody who like really gets to see everything I do in every minute, that's the one, right? This last seven, eight minutes, like, if we could deconstruct this in a meaningful way, it's the one. Like, I genuinely think that people are in the business of thinking, "What's in it for me?" And I only think, "What's in it for me is my legacy." I am obsessed with what Nick says behind my back. It's just interesting. I think it's an interesting thing.

• 39:22Lewis Howes?

  Says good things about you.

• 39:23Gary Vaynerchuk?

  Right, and like, I know how well I know him, and he knows how well I know him. We know each other, we're, we're in between that zone of acquaintances and friends. We haven't spent enough time to, by the way, I'm going on a complete tangent. Aren't you fascinated by the serendipity of something happening that takes an acquaintance to a friend? It's usually predicated on something like a trip, or some weird night where like, I'm like desperate for one of my flights to be canceled, and I'm there with it. A dream for me would be on a, to go on a red eye from LA to New York that Nick's on. It gets canceled, and for some reason, it's a blizzard and we can't leave the airport. I know in those six hours, sitting there, that's where the friendship gets made. Love that shit. Early college is that for a lot of people, right? Remember that first conversation you had, probably around like, the first week of October, with the kids you just met?

• 40:06Gary Vaynerchuk?

  And you like stayed up to four o'clock, and like, one dude cried, and like, like, you know, and like, forever, that night, you're like, literally, like, I'm literally still texting kids, who are my friends, 21 years later, off of that October 7th night, where like, two people cried, and I'm like, "I love you dude," like, like, and you've only known the guy for four weeks, but like, now you're friends forever. Like, college, college is the biggest racket, and everybody, everything college should go to jail for the debt structure that's created around it, but no question, and that's why I love like, whether it's a Soho House, or the Subnit Sea thing, or South by Southwest, getting people into a place where they have to spend two to three nights together, is powerful. I've actually been thinking about launching a club thing, that where, it's called Tuesday.

• 40:51Gary Vaynerchuk?

  I have this idea of a club, that's called Tuesday, and you walk in at night, like, the only way you're in this club, think Soho House, New House, think about those kind of places, where you have to be there by nine o'clock, Tuesday, and you don't actually leave until 6 a.m. Wednesday. You're like, "Suck." And there's like showers and beds and like obviously some weird shit could go down. But I'm not caring about the weird shit. I'm caring about like what actually happens when you're forced to spend the night. Here's what happens. You'll have dinner with people, but it's what's gonna happen from 11 to 3 in the morning? That will forever change your relationship with that person. So I'm trying to create a context and force. You know what I'm pumped about that we just said this is this is now on the record. I've never said it out loud. I probably won't do it because I'm busy, but it's now gonna happen.

• 41:36Gary Vaynerchuk?

  And of course they're gonna call it Thursday to like disguise it. That's my shit. You motherfuckers, that's gonna Tuesday, you dick.

• 41:43Lewis Howes?

  We only got a few minutes left, so I wanna make sure that I get to a couple of questions left. Well, before we get to the final questions, I wanna make sure everyone gets the book. We don't have the copy right here like we usually did. You just got it like this morning, but it's back in New York. Make sure you guys pick up Crushing It.

• 41:56Gary Vaynerchuk?

  Louis is in it.

• 41:57Lewis Howes?

  I'm in the book. I think there's a few pages of me or it's like a whole profile about.

• 42:01Gary Vaynerchuk?

  There's a whole profile.

• 42:02Lewis Howes?

  My story of reading Crush It, meeting you, you know, nine years ago and what the book did for me. And, you know, my favorite chapter is the one about caring and giving. I think it was the one word chapter, care, right? And that's been my approach ever since. I mean, I think I came from that before I read it, but when I read it.

• 42:19Gary Vaynerchuk?

  Sometimes when you put something on paper, right?

• 42:20Lewis Howes?

  Yeah, it was like, okay, what can I do? And hopefully you felt this from me that every year I'm thinking, how can I give to Gary?

• 42:28Gary Vaynerchuk?

  Let me help. Let me say something about you that's nice because I like your audience to hear it. But more importantly, it will help so many people. When you started trying to care towards me as your career evolved over the last nine years, the first four times that you cared, I thought this is the setup for the other thing.

• 42:47Lewis Howes?

  The ask or something, right?

• 42:48Gary Vaynerchuk?

  Because that's what we as humans think. That is the environment we live in. I'm sure that's what people feel about me. The fact that you, look, I think here's, here's the thing. Here's, actually, let me say this about you as well. There's a, this is a good topic. I wanna pay forward at all costs. I wanna give, give, give, give, give, give, get right jab, jab, jab, right hook. Like if I had it my way, that book would have been called Jab, Jab, Jab, Jab, Jab, Jab, Jab, Jab, Jab, Jab, Jab, Jab. Right hook. I think the thing that you have that I have, and this is our kinship and no question speaks to our success, is we're very willing to give.

• 43:21Lewis Howes?

  Yeah.

• 43:22Gary Vaynerchuk?

  We're not scared to ask for something in return, but we are not crippled. We don't overreact to somebody coming through, and we're not crippled when they don't.

• 43:31Lewis Howes?

  Right.

• 43:32Gary Vaynerchuk?

  I'll give you a great example for everybody listening. When School Greatness came out, you emailed, you reached out. I was able to buy a bunch of books. We did all the right things. When masks came out, this feels like, what, three months ago?

• 43:41Lewis Howes?

  Yeah.

• 43:42Gary Vaynerchuk?

  I remember this clearly because I kept getting scared that I was feeding up because you reached out, you're like, this is coming. But I had some shit going on, just like business stuff.

• 43:50Lewis Howes?

  You were really busy too.

• 43:51Gary Vaynerchuk?

  No, but I was just really like, between personal life and business. And I just remember like, because I remember this because I was like, oh shit. I gotta, it wasn't like notes. I'm like, oh, I gotta reach out to him. I gotta, and then I like hit you up and I was like, dude, where are you? Like dude, I was in New York four days ago. Like, but you know what's interesting to me? That, because that's how I play. Sometimes people will come through, sometimes they don't. Giving with expectation is a devastatingly bad idea that 99% of people do.

• 44:16Lewis Howes?

  Mm-hmm.

• 44:17Gary Vaynerchuk?

  And somewhere after the fourth time you ask to do something or this, I'm like, oh, he can figure it out? So now, I look forward to the asks.

• 44:26Lewis Howes?

  Right.

• 44:27Gary Vaynerchuk?

  I want to support the asks. I'm always supporting.

• 44:29Lewis Howes?

  And I don't really ever ask. It's like.

• 44:31Gary Vaynerchuk?

  You ask the same way I ask.

• 44:32Lewis Howes?

  Yeah, it's like once in a blue moon.

• 44:33Gary Vaynerchuk?

  Oh dude, do you know how pumped I am that crushing it's selling so well? So I don't have to ask?

• 44:37Lewis Howes?

  Exactly.

• 44:37Gary Vaynerchuk?

  Because I also have the next two K-Swiss sneakers coming out and they sold out so fast that we've produced so many. So I'm like, oh shit.

• 44:44Lewis Howes?

  Now you need that.

• 44:45Gary Vaynerchuk?

  Like dude, do you want to wear a fresh new pair of K-Swiss's every day for the whole year? Yes, please buy 365 pairs of my next sneaker.

• 44:53Lewis Howes?

  And my mentality is also, and I think of people listening can take a page out of this. My mentality with you is, I'm thinking of how can I give to you without you even having to ask?

• 45:03Gary Vaynerchuk?

  I totally get it. Me too.

• 45:04Lewis Howes?

  Like I made a couple, I don't even know if you saw them on the email, but I made a couple introductions where guys were like, I want to buy a couple thousand books from Gary. And I said.

• 45:11Gary Vaynerchuk?

  Let me tell you how, yeah, like making intros and like, hey, you know who buys four or five or 10,000 of yours. You made intros of people that, and you're winning, right? Because I'm not as easy to get to these days. So you won twice and that's so smart, right? You're getting, these people, a lot of them have told you this, I'm sure. Because if you intro, I'm saying yes.

• 45:28Lewis Howes?

  Right. Well, I say the only way I'm going to intro is if you buy a 2,000 books.

• 45:31Gary Vaynerchuk?

  But even more interestingly, these are people that have reached out 10 times that say, I'll buy 3,000 and I don't reply.

• 45:36Lewis Howes?

  Really, yeah.

• 45:37Gary Vaynerchuk?

  And then you do it and I do, which I know makes you go, but like for me, the best part is now that I'm in a different kind of like, as my brand grows, as my career grows, as my reputation grows, that's reputation. Because when I say brand, I know a lot of people are like, uh. Reputation, that's what it is.

• 45:51Lewis Howes?

  Yeah.

• 45:51Gary Vaynerchuk?

  What's been fun for me is when real senior people, not people with like 10,000 Instagram followers. I mean like the 74-year-old lady that's running the world that you haven't heard of. What's been fun for me, and this is the thing that, back to Nick, what he says behind my back. When real power players, like 80 billion dollar hedge fund people that want to invest in something, or somebody deciding, even when you've got somebody as incredible as Scooter behind you, when you're looking at TV stuff, when there's people that are on the board level of a network saying, "Hey, this guy's coming through the path, we're trying to..." You know this, anybody that's growing up in our era, everyone's trying to figure out, "Is this real or is this fake? Is this a real dude?" Nothing is more fun now.

• 46:35Gary Vaynerchuk?

  Look, buying 500 books is the easy part. Me putting my reputation on the line for somebody else is the thing that scares the shit out of me. And I think the thing that's a lot of fun, and this is the hidden thing, that all the kids and even the 70-year-olds that are in kid mentality don't get it. I had a meeting, I was with Scooter today.

• 46:52Lewis Howes?

  Yeah.

• 46:53Gary Vaynerchuk?

  We talked about the game. We talked about multiple people that we're fine with, we like, but deep down, everybody knows this, there are plenty of people that feel, that you have relationships with, that that person will feel like you guys are fine. Why would I say something bad about somebody? Like when there's no benefit. But if somebody said, "Your reputation's on the line", and this happens in real life, guys, this is what's happening. Just so you know what happens as you continue to try to build your game, there's always this moment, there's so many huckster kids running around right now who claim to be friends with all of us.

• 47:25Lewis Howes?

  So they know someone.

• 47:26Gary Vaynerchuk?

  That's right. Who, all of us are nice people, but behind the scenes, if you're a huckster and you're doing it just for you, and you're name collecting to get selfish, short-term shit for you, let me tell you what's happening. At dinner, four of the people that are really winning are having dinner, your name gets brought up because maybe the fourth person's like, "Hey, this kid's been reaching out to me and says he's homies with all three of you ironically." What's the story? You are getting shit on.

• 47:51Lewis Howes?

  Yeah.

• 47:52Gary Vaynerchuk?

  You think you're winning. And again-

• 47:54Lewis Howes?

  On a micro level.

• 47:55Gary Vaynerchuk?

  On a micro level, you are. Like, that person's commenting on your Instagram post, you're at a conference and they high-five you and give you a hug.

• 48:02Lewis Howes?

  We got a selfie with them, yeah.

• 48:03Gary Vaynerchuk?

  But the truth is shit. I'll wrap it up perfectly. The curtains look good.

• 48:08Lewis Howes?

  Yeah.

• 48:08Gary Vaynerchuk?

  The painting looks good.

• 48:10Lewis Howes?

  Foundation.

• 48:10Gary Vaynerchuk?

  But the foundation can broken. And here's the punchline. The four titans that are winning, they're not wrong.

• 48:16Lewis Howes?

  Mm-hmm.

• 48:16Gary Vaynerchuk?

  Because they're just being polite. You're wrong because you're doing behavior to game those titans for your selfish needs. And you look like an idiot to the 1% and you look cool to the 60% that don't matter and the 39% in the middle are trying to figure it out.

• 48:31Lewis Howes?

  Hmm.

• 48:33Gary Vaynerchuk?

  Too many people winning with the 60%.

• 48:35Lewis Howes?

  Yeah. What advice would you have for me over the next 10 years? You've seen the first 10 years from crush it to crushing it now in my career evolving. This isn't for selfish reasons.

• 48:44Gary Vaynerchuk?

  No, I think it's gonna help everyone. Here's my thing. I think you're at the point now where you need to decide if you want to build a business for yourself that isn't around you as a human. Do you have that ambition or not? If you do, you should start getting serious about it. If you don't, you need to quadruple down on the Lewis Howes business.

• 49:06Lewis Howes?

  Mm-hmm, yeah.

• 49:07Gary Vaynerchuk?

  That's the only decision you have, in my opinion. It's actually binary. Do I, Lewis? Should I buy Prince, the tennis racket company? And do I want to buy a company? Do I want to start a company? Like, or do I want to triple down? For you to have this much brand awareness around a human, you've got to decide if you want... Like, if you look at all these pictures, a lot of those people make the majority of their money being that human. But if you look at the CEO of Spanx or if you look at something, there's... I'm in that category. They're making their money other places and happen to also have that. You need to decide, are you gonna still just only be Superman? Or is there a Clark Kent in your repertoire? And that doesn't mean that you have, like...

• 49:51Gary Vaynerchuk?

  I'm looking at Logan Paul. He's obviously going through his own stuff and like, what right now? But like, he sells hoodies and makes millions of dollars. But that's 100% still on his brand.

• 50:00Lewis Howes?

  Yeah.

• 50:01Gary Vaynerchuk?

  That's different than VaynerMedia. That's different than Spanx. That's different than my ambition to buy K-Swiss and be the CEO of K-Swiss. And it's not because I'm the face of, I'm the operator. Do you want to be the operator of a business that 90% of it, the customers don't care you're this person?

• 50:19Gary Vaynerchuk?

  Or do you want to continue there? That's, I think, the most interesting thing for you to think about, right?

• 50:23Lewis Howes?

  Yeah, it's good, good advice.

• 50:25Gary Vaynerchuk?

  You know, there haven't been, you know, Phil Knight and all these, I'm looking at books around here, they didn't have that. There was no way for Phil Knight to make $4 million a year being Phil Knight in 1984. All these youngsters now can do that, you're a youngster. What's interesting is, like, our mutual friend Adam Braun, there was no kids building huge nonprofits, right? So like him, when he wanted to go on and do, build a business, there was like this weird dynamic of like, wait, you're not allowed, you're a nonprofit. Of course he's allowed, but he's a first of generation where kids started nonprofits from the get and then go private. Same for you. You're part of the generation that can make a great living just being the person. Now, your question is, do you want to build a business that is scalable outside of yourself? Or do you want to quadruple down?

• 51:09Gary Vaynerchuk?

  And truth is, both work, that's just up to you.

• 51:11Lewis Howes?

  Yeah, cool. Final two questions. This is called the three truths, and I don't remember if I asked you last time, but if you did, maybe it'll be different now. If this was the last day for you many years from now, you've done everything you've wanted to achieve, you've created it all, you've said everything, but for whatever reason, all your books and shoes and businesses have been erased. And so, there's nothing left that people have to remember of you. But you've got a piece of paper and a pen to write down three lessons or three truths that that's all they would have, that you would share with the world. What would those three things be?

• 51:42Gary Vaynerchuk?

  5149, I would draw that first, and then I would like, in parentheses, explain it. It would say, "Give more than you take." And then, we talked a lot about that the last 15 minutes. It just works. And the reason 5149 works is it painted a picture for everybody right now, who's been listening for the last 20 minutes, and like, that's an interesting insight of like, why Gary and Lewis are winning. That's the right number to me. And I've debated, like, should it be 50.1 to 49, you know? But then, you can still be selfish in the power of your selflessness. So 5149, I would say, legacy over currency. How many people show up to your funeral is the KPI? Because if you're great at that, you're gonna have money. Like, occasionally, you have somebody who's a teacher and like, or sat on the porch of

• 52:26Gary Vaynerchuk?

  a town and everybody loved him, but like, most people that have 10,000 people or 5,000 people show up to their funeral. And by the way, just being loved is better than having money. Like, how much money do you need? So anyway, legacy over currency, and then the third one would be patience. It is the, it is the disease of our society. The lack of patience, bro. I mean, it's crazy to me that literally patience and insecurity is 90% of the unlock for everybody listening right now. Their mom shitted on them their whole life and said they're gonna be a loser, so they believe it, because that's what parenting is. And they just wanna have a Maserati now. And they'll do whatever it takes to do it. And so they'll take, they did something, like, do you know how many kids are doing something

• 53:09Gary Vaynerchuk?

  smart, like doing a good retail arbitrage on Amazon right now and making a hundred thousand dollars by buying on Alibaba and selling on Amazon? Took a year and a half, three years, to get good at it. But now we're taking every profit and buying some rando cryptocurrency because they're playing the Lotto. This is what's going on in our society. Like, we have to have these conversations.

• 53:27Lewis Howes?

  Saying big gains fast, like, let me jump in.

• 53:29Gary Vaynerchuk?

  Like, there's a kid who spent three years being disciplined and getting good at retail arbitrage. It's a real skill to have an eye for, like, what to buy in China, how to set up on Amazon properly, how to run ads. Like, it's a skill.

• 53:40Lewis Howes?

  Yeah.

• 53:41Gary Vaynerchuk?

  They did it for three years meticulously, they made thirteen thousand, then forty-seven thou-- now they finally are making three hundred thousand, and they could be on their way to ten million? Yet, they've chosen to kinda stop, jump on the short-term bandwagon of buying some weird cryptocurrency, hoping it's the next Bitcoin or Ethereum. I'm just seeing that every day, and I'm just like, it's being predicated on short term. You hear one story, Zucks did it. Instagram sold in 550 days for, now I'm, that's why everybody started an app company, to follow the leadership. Completely predicated on short term. I went the other way. While everybody was blowing up, I decided to build an agency. Boring-ass, shitty-ass business in the prime of my career, when everything was going for

• 54:26Gary Vaynerchuk?

  me in Silicon Valley. I'm proud of that. I think I'll be historically correct, so, those are the three things I would say.

• 54:33Lewis Howes?

  That's great. Before I ask the final question, make sure you guys get the book, crushing it, it's out now, you can preorder it, or it's out now. Get the audiobook, preorder that, which is coming out in a couple months, I think. If you don't already follow Gary, make sure to follow him, @GaryVee. Instagram seems like it's your platform of choice these days, it's been crushing it.

• 54:51Gary Vaynerchuk?

  Yeah, I got real serious a year ago.

• 54:53Lewis Howes?

  Literally, it's been blowing up in a massive way. Your attention there is unbelievable. So go follow him there if you're not following him already. One final question before I ask, I wanna acknowledge you for a moment, Gary, for constantly showing up. Since I've known you 2008, 2009-- You're constantly giving. You care deeply about everyone. You always wanna give. And you're doing things that aren't necessarily the most popular things to support other people. So I wanna acknowledge you for constantly being yourself, speaking your truth. You never hold back. Just like now, you're always gonna say it like it is. Your authentic ability to give, to speak what's on your mind, I really acknowledge that.

• 55:31Gary Vaynerchuk?

  Appreciate it, brother.

• 55:31Lewis Howes?

  Appreciate it. Final question, what's your definition of greatness?

• 55:35Gary Vaynerchuk?

  I've never really thought of that. You know, it's funny, a couple of things ran through my... I'll just go with what ran through my head. First thing that came to mind is that a lot of people know who you are because you've impacted them in a positive way. The second thing that came through my mind was interesting was when you say somebody's name, you feel something. You know, like when you get nervous, like some version of like excitement and butterflies? I'm fascinated by the word "great" because I think it's one of those words that has absolutely been like... I think about sportscasting, it's funny. Everybody's nostalgic about their youth, and you always become the old man or old woman. The way "great" gets thrown around, you know, I'd love to get your perspective on this because you've anchored into this so heavily, but like... Those are the two things that come to mind.

• 56:19Gary Vaynerchuk?

  Like that mix between nervousness and excitement in your stomach. Or, like, to me, it's like when you hear a name, like, it's funny. Martin Luther King's birthday was the other day, right? I went to Martin Luther King Middle School. Like, I don't think we can wrap our head around the people that have changed the world because that's a level of selflessness. Like, I'm pumped because I'm gonna be 50% selfless, selfless, and I think I'm gonna be legendary for it. There's people out there that are 100% selfless. I think for entrepreneurship, you have to be 50% of each. But it's wild to me that I am gonna be far more successful and great because of the DM that I'm gonna send to a kid tonight than for the 97 things I'm gonna be right about in business over the next century

• 57:02Gary Vaynerchuk?

  and will make me successful. Doing the right thing is always the right thing. There's something in that statement with greatness. I think to be great, you have to be an enigma. You have to be like against the status quo. You have to be willing to say "work-life balance in its current state", like I did earlier in the segment, so... Yeah, just different. And invoking a reaction. A human reaction must occur, otherwise you're not great.

• 57:29Lewis Howes?

  Gary, thanks for that. Appreciate you.

• 57:36Lewis Howes?

  There you have it, my friends. If you enjoyed this special episode with Gary Vaynerchuk, then make sure to share this with your friends. Tag me on Instagram with a screenshot of this podcast image, and let me know what you thought. Tag @GaryVee as well. I'll be screenshotting them, posting them on my Instagram story, retweeting them, posting them on Facebook. So make sure to tag both of us, @lewis house and @GaryVee on Twitter and Instagram with what you thought about this episode. And if you did enjoy it, make sure to leave us a review over on iTunes. Again, you can do it right on your podcast app if you're listening on your phone, or go to lewis house.com/itunes and leave us a review for your chance to be shouted out as a fan of the week. Also, make sure to

• 58:20Lewis Howes?

  pick up a copy or two of the book. Get one for yourself and give one to a friend. Again, I'm in the book, so I'd love to hear your thoughts about my case study of my journey. Again, so many people are always interested about what I've been able to do over the last eight to 10 years, and I talk a little bit about the things I learned from Gary's original book, Crush It, and how I've applied that specific principle towards my business. So you'll learn a lot in the book. Go check it out. Get a couple of copies for your friends as well. Again, if you enjoy the School of Greatness podcast, and if this is your first time here, then welcome. I hope you subscribe to the podcast. And if you want to watch

• 58:59Lewis Howes?

  the full video interview, you can do that at lewis house.com/595 for this episode with Gary Vaynerchuk. And if you've been here many times before, then welcome back and thank you again for constantly listening and sharing this with your friends. Our mission is to bring you the greatest and brightest individuals in the world to help you unlock your inner greatness. You were born for greater things than you have right now. And Ralph Waldo Emerson said, "To be yourself in a world that is constantly trying to make you into something else is the greatest accomplishment. All you need to do is become more of you.

• 59:41Lewis Howes?

  Continue to overcome your fears. Continue to step out of your comfort zone, to grow, to learn, to develop, to tackle life's greatest challenges, and become your best self. Be yourself." And become your best self. I love you, and you know what time it is. It's time to go out there and do something great.

• 1:00:05Lewis Howes?

  You