955 Gary Vaynerchuk on Mindset, Family and The Future of Business

“Leaning into humility and gratitude will be the springboard to everything you want.”Gary Vaynerchuk is the chairman of VaynerX, a modern-day media and communications holding company, and the active CEO of VaynerMedia, a full-service advertising agency servicing Fortune 100 clients across the company’s 4 locations. After growing his family business through what Gary calls “underpriced attention,” including the impact of content, ecommerce, email marketing, and Google AdWords, Gary began his own journey of producing original business content as the voice of entrepreneurship online. Today, Gary has more than 12M combined followers across social media. In this episode, you will learn:-How hard work is revolutionizing things right now-How Gary’s work is more art than work-How humility plays into being a successIf you enjoyed this episode, see show notes, video and more at http://www.lewishowes.com/955 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 955 with the one and only Gary Vaynerchuk.

• 0:07Lewis Howes?

  Welcome to the School of Greatness. My name is Lewis Howes, 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?

  I've got a few quotes for you today. Steve Jobs said, "I'm convinced that about half of what separates successful entrepreneurs from the non-successful ones is pure perseverance." Peter Drucker said, "Entrepreneurship is neither a science nor an art, it's a practice." And Dr. Martin Luther King Jr. said, "If you can't fly, then run. If you can't run, then walk. If you can't walk, then crawl. But whatever you do, you have to keep moving forward." I'm so excited about this interview with my friend Gary Vaynerchuk, who I've known for over a decade now. And I've seen Gary transform multiple times, over and over, reach incredible success,

• 1:16Lewis Howes?

  but also go through multiple failures, day in, day out, year in, year out, and continue to grow with both of them. And continue to take the punches, continue to put out consistent content, whether it be books or social media content, or audio or video, continue to launch new businesses, and continue to make an impact. And if you don't know who Gary is, he is the chairman of VaynerX, a modern day media and communications holding company, and the active CEO of VaynerMedia, a full-service advertising agency servicing Fortune 100 clients across the company's four locations. And after growing his family business through what Gary calls "underpriced attention", including the impact of content, e-commerce, email marketing, and Google AdWords,

• 2:01Lewis Howes?

  Gary began his own journey of producing original business content as the voice of entrepreneurship online. And today Gary has more than 12 million combined followers. On social media, producing content daily on places like Instagram, YouTube, Facebook, Twitter, LinkedIn, Snapchat, Spotify, and more. And in this episode, we talk about the All In Challenge and what motivated Gary to collaborate on this cause that has already raised over $41 million during this time. The importance of direct-to-consumer businesses, especially in this time of isolation. Gary talks about his favorite thing about being a father and what his father taught him about being a better father to his kids. How to balance family, health, and business when you're an all-out entrepreneur. Also, what

• 2:46Lewis Howes?

  it was like when his business partner and his brother, AJ, stepped down from his current business. This was a big one. And how to overcome self-doubt, the keys that's worked for him, and what advice he would give to you to overcoming self-doubt and the need for other people's opinion. That and so much more on this incredible catch-up with my good friend, Gary Vaynerchuk. And at any point while you're listening to this, make sure to just text a friend this link, lewishouse.com/955, or just copy and paste the link on Apple Podcasts or Spotify and share it with a friend. And if you're really getting value out of this, make sure to screenshot this while you're listening, post it on your Instagram story and tag me, Lewis Howes, and tag Gary V to let them know that you enjoyed this

• 3:31Lewis Howes?

  episode. There's some powerful stuff, and I want to make sure you get through to the very end. All right, my friends, I'm so excited about this. Get ready, dive in with the one and only Gary Vaynerchuk.

• 3:46Lewis Howes?

  Welcome back everyone to the School of Greatness Podcast. I've got my man Gary V in the house. Gary, good to see you, brother.

• 3:52Gary Vaynerchuk?

  Good to see you, man. You're looking good.

• 3:54Lewis Howes?

  You know, the thing that I appreciate it, you're looking, you're looking lean yourself. The thing I appreciate about you the most, that most people don't know about, is I've known you since 2009, and what people don't know is that I am the all-time thumb wrestling champion of the world. And there's, there's proof somewhere. Someone has a video clip of me holding it for three seconds. You know, it was a two and a half count.

• 4:17Gary Vaynerchuk?

  Everybody that is, is watching or listening to this knows you're an incredible physical specimen. You know, like, it is just the truth. You're a, you're a god amongst men, my friend.

• 4:28Lewis Howes?

  But the thing I appreciate and love about you the most Gary is I've known you for 11 years, I believe, 2009, maybe it's 2008, but I think it was 2009, January, I believe it was at Affiliate Summit when I first met you, I think it was January 2009 in New York City. And I've gotten to see you behind the scenes over the years at different events and, you know, I've driven you in a car from one of your book events early on and like a beat up car. You know, we just had moments here and there at different settings. The thing I appreciate about you is how giving you are of your time, your energy, your resources, your wisdom, your money, you know, you've been donating to Pencils of Promise for years. I see you at the gala all the time, you're giving your time and energy and money. And I think it's the thing that a lot of people don't see about you enough is how giving you are

• 5:13Lewis Howes?

  and you're especially involved in the All In Challenge right now. I think you guys have raised like 40 or 50 million dollars already.

• 5:19Gary Vaynerchuk?

  Yep.

• 5:19Lewis Howes?

  And I know how much time behind the scenes it's taken for you to coordinate, work with Ruben and just like put this together and call in favors, like there's so much giving you do. So I just want to say thanks for all the

• 5:32Gary Vaynerchuk?

  I appreciate that. Look, I think, you know, I think it's really funny, right? Because I'm very much, you know, willing to self-promote myself, I'm willing to promote my businesses. But you know this about me because we have been friends for a long time. Like I'm a little bit more quiet about the best version of me, right? And, and I, I'm okay with that because I think, you know, we're all affected by things. I think I was affected as I was coming up the game of realizing, wait, people use charity or other things for their own self-interests, like they're positioning themselves and, you know, and by the way, I, I definitely don't begrudge people promoting their philanthropic kind of ventures either.

• 6:13Gary Vaynerchuk?

  I think we're all wired differently, but I, that's very nice for you to say and I appreciate it.

• 6:18Lewis Howes?

  Of course, and I think there's like, I've tried to learn, like, how do you balance like self-promotion versus like promoting something that's a good cause that people need to be aware about and for them to promote, to donate also, it's like a balance of

• 6:31Gary Vaynerchuk?

  The balance.

• 6:31Lewis Howes?

  what to talk about, what not to talk about. So I think you've done an amazing job of that and people need to know more about that. Can you share quickly about All In for people that can get involved?

• 6:40Gary Vaynerchuk?

  Yes.

• 6:41Lewis Howes?

  What it is, if those haven't seen it from every celebrity yet?

• 6:45Gary Vaynerchuk?

  So Michael Rubin, the founder of Fanatics, came up with this idea, the All In Challenge, AllInChallenge.com. He was sitting around like everybody else, wanted to give back, called his buddy Alan Tisch, called me. We started hacking at it and the idea evolved into the greatest experiences from people in culture, music, film, you know, television, sport, of course. It's gotten into some experiences. We've got some, and it's basically auctions and sweepstakes for people, you know, Tom Brady's flying somebody out to Tampa for the first game and, and they're sitting, you know, 50 yard line, they're getting on the field beforehand, and then he's going to dinner with them and giving them the first jersey he wears and the cleats from his first Tampa game.

• 7:29Lewis Howes?

  That's crazy.

• 7:30Gary Vaynerchuk?

  You know, that, that auctioned off, I think that went for almost a million bucks. Then there's raffle tickets for $10. Somebody is going to be, somebody actually won for $10, the ability to have a speaking role in Leonardo DiCaprio, Martin Scorsese's film. So there's just all sorts of crazy stuff. If you go to AllInChallenge.com, unlimited $10 raffle tickets for Bieber to come and sing at your house, like just crazy, crazy stuff. And, and it's completely popped off for the last month, over $40 million raised at this point. We're super proud of it. You're right, it has been 15 hour days while still trying to navigate VaynerMedia and VaynerX, while also losing all my income from speaking, which is really kind of what allows me to invest in.

• 8:12Lewis Howes?

  That's your money, yeah.

• 8:13Gary Vaynerchuk?

  Yeah, that's the place where I make revenue that allows me to kind of invest in top line growth for Vayner, not worry about profit as much, or make investments, or try new ventures. So like.

• 8:23Lewis Howes?

  Take risks and try, yeah.

• 8:24Gary Vaynerchuk?

  A hundred thousand, be, be nice and do nice things, like, you know. So it's definitely been a very intriguing eight weeks.

• 8:33Lewis Howes?

  Hmm. I asked a bunch of people about an hour ago on my Instagram Live, I said, what's a question, because you're doing, you know, Tea with Gary Vee every day, you're, you're giving so much content right now, which is amazing and helping so many people. And I said, what's a question that you haven't seen Gary talk about? And you've seen a million posts a day from Gary, share a lot of incredible stuff. Is there a question? That he hasn't answered yet, and I wanted to ask my audience this. So I want to get to that in a second.

• 9:00Gary Vaynerchuk?

  Okay.

• 9:00Lewis Howes?

  Before I do, I posted, uh, I saw a stat out there about a bunch of different companies that launched from 2008 to 2010, right around the time I met you when I was on my sister's couch and I had no money and I was like, what's happening? It's kind of a similar feeling of the economy.

• 9:15Gary Vaynerchuk?

  Yeah, yeah, yeah.

• 9:16Lewis Howes?

  Uh, and some of those startups that founded back then, Uber, Airbnb, Slack, Pinterest, WhatsApp, Square, Venmo, which you're an investor in. And they have blown up in the last decade. I'm curious, what are the ideas or businesses that should be created today, moving forward? That in 10 years, we'll be looking back at the next, you know, crisis and say, this is the companies that were started in 2020. What are those industries? What are those topics? What do you think?

• 9:43Gary Vaynerchuk?

  Pract- practical, direct to consumer brands, you know, ones that are own, like DTC for brands is an incredible business. Overfunding and trying to go public or sell to somebody is why a lot of them are going to go out of business. Um, I think that you're going to see some really fascinating innovations. I've been thinking a ton about co-working. Obviously, we had WeWork and obviously they have their challenges for overvaluations and over. But, but I do think business as usual, I mean, geez, talk about, like, I've been thinking about things like for just small entrepreneurs, like create a business about renovating home offices to be epic. Because the amount of people that are going to work one to two times a week from home is going to be, so just like, think about if you're a carpenter, right?

• 10:28Gary Vaynerchuk?

  Like you just brought up all the, you know, billion dollar things and honestly, those, there's never a bad time to start a great business. And the Travis's and the, all the other people that you, the companies you just mentioned, those, those were individuals that had that talent. The reality is, that's the 1% of the 1% of the 1% of the 1%. The reality is you and I have audiences that listen to, will listen to this and watch this, that are really great entrepreneurs that are destined to build $500,000 a year businesses. If you're a general contractor or a handy man or woman, positioning yourself as a home office specialist right now, I couldn't even imagine. You probably could go from being a $35,000 to $50,000 a year person with one or two projects to like a million dollar person.

• 11:12Gary Vaynerchuk?

  Cause that is clearly coming. So that's on my mind. Um. You know, little things like I saw AJ bought for our entire family some sort of like keychain ring that helps you, you know, ring doorbells and put keys into like, like, like I, I, I do think, you know, like people are about to be germaphoned out in perpetuity, similar to, similar to nine 11, I, you know, which sucks for me because I'm a very other way, like, like hug, kiss, like, you know,

• 11:42Lewis Howes?

  Slobber on someone's face.

• 11:44Gary Vaynerchuk?

  Slobber, like, yeah, I'm very like, you know, like, don't wipe down anything when I get on the plane, like,

• 11:48Lewis Howes?

  Share drinks and eat hot dogs together.

• 11:51Gary Vaynerchuk?

  No, honestly, eat off people's food. Like, like I, I'm a little bit worried that I'm about to be shunned from society. Um, but I think, I think like cleanse, cleanse, clean, safe, those are gonna be great. I mean, talk, create, somebody should create a high-end hand sanitizer business.

• 12:08Lewis Howes?

  That's true.

• 12:09Gary Vaynerchuk?

  You know, so I think there'll be some trends and then back to the point I made, a good business is always a good business. Um, I, I, for example, opening a restaurant immediately after this sounds insane, except if you're opening up a great restaurant.

• 12:24Lewis Howes?

  Yeah. You know, it's interesting, and I'm in LA near Beverly Hills and I'll drive down this side street with, uh, Sprinkles Cupcakes. I don't know if you've heard of Sprinkles.

• 12:31Gary Vaynerchuk?

  Of course, know it well.

• 12:32Lewis Howes?

  It's amazing. While all these restaurants are shut down or they're like, doing their own version of delivery or whatever it may be. Sprinkles Cupcakes had an ATM machine four years ago, five years ago, before it's time, where you can go at any time of the day and get a cupcake out of the ATM machine, fresh, made that day. I tell you, I kid you not, there's a line down the street in Little Santa Monica, of people at Sprinkles all day long, just getting out of this ATM machine and people are in there all night working because they can't supply the demand fast enough. So, something innovative like that.

• 13:05Gary Vaynerchuk?

  Listen, listen, my, I, I, my dad a year ago said, hey, you're helping all these companies. What about helping old dad out? And I launched Wine Text, right? Which I've been promoting very heavily. And it's an innovation, you know, it's you get a text, you reply with a number. Anybody who's listening that's into wine, if you really buy wine on the internet, you have to go check out wine text.com, you get, you sign up, you put your credit card in, it takes two minutes. And then you get a text every day and you reply with four, five, two, one, 12. And, and it's like Brandon hired nine people today for Wine Library because, you know, obviously alcohol sales are exploding, but, but on top of that, this is above and beyond because the innovation is so strong.

• 13:43Lewis Howes?

  What is the direct result from you guys implementing that for this new kind of business for Wine Library? How is that?

• 13:50Gary Vaynerchuk?

  It is, I'll tell you exactly. I don't have the exact map. I actually have a P and L meeting tomorrow. Roughly, it's, it's going to grow the business by 30 to 40 percent. Percent!

• 14:00Lewis Howes?

  From last year, just one initiative.

• 14:02Gary Vaynerchuk?

  One initiative.

• 14:03Lewis Howes?

  Wow. And that's a, do you guys use community for that?

• 14:07Gary Vaynerchuk?

  You know what? We don't because the way we, we structured it, community wasn't far enough along. Obviously, I'm an advisor and use community for my personal brand. We, we built a, a middleware between our platform and broadband.com. And it's like, we, it was custom built with our dev team at Wine Library, but it's just working and innovation. And, and by the way, let's call a spade a spade, Bainer Wine Library, excuse me, has been declining for a decade because I'm not there. And then one idea is going to-

• 14:33Lewis Howes?

  It's going down 5, 10% a year or whatever, and now boom, let's get it back to where it was 10 years ago.

• 14:38Gary Vaynerchuk?

  I think there's a chance next year, if this keeps going the way it's going, we'll be at heights we've never been. One idea, one execution. And what is it? It's, it was my observation 18 months ago that people are willing to get marketed to on text more in America than they were five years ago.

• 14:54Lewis Howes?

  Mm-hmm. It's brilliant. And now you have been, you've been teaching this for years about shifting your perspective, shifting your mindset, having self-awareness. You've been teaching this for years. And people don't listen when times are good. They stay stuck in their mindset or their fears. I'm afraid to launch this, put this out there. How do people shift their mindset even in a horrible time? For most people, when they can't even do it during a great time.

• 15:20Gary Vaynerchuk?

  Easy. I'm, my stuff does better during bad times.

• 15:25Lewis Howes?

  Cause they have to.

• 15:26Gary Vaynerchuk?

  Right. You and I hung out during the Crush It! book signing. That's when you drove me. Crush it, hit a nerve, because people needed it.

• 15:33Lewis Howes?

  2009, right?

• 15:34Gary Vaynerchuk?

  Right. And that's when hustle was good. And then hustle during good times becomes manipulated into burnout. But I promise you right now, I don't use hustle anymore because I understand how the word got mutated into leading to anxiety. And so I don't want that. So I, I changed it. Even in Crush It!, I talk about nine to five, making 40,000 a year, being happy. But, but I promise you, hard work is about to be put on a pedestal again.

• 16:00Lewis Howes?

  Huge pedestal. I'm, what is it, 20, 30 million people unemployed? Like, people are gonna be grateful just to have an opportunity.

• 16:05Gary Vaynerchuk?

  A job. That's right. I don't think people, I think people are still in a little bit of a shock slash fake environment. If we get back to normal in September, I'm just gonna be, and I know that we won't be back to normal. Let's just talk about January. If God willing, we're back to real kind of normal in January. I think by February, by Valentine's Day, people are gonna walk around and be like, oh, wait a minute. There's some real lasting ramifications.

• 16:29Lewis Howes?

  Big time. Big time.

• 16:32Gary Vaynerchuk?

  I can't get a raise. I can't get a job.

• 16:34Lewis Howes?

  Yeah, I mean, I'm just hearing people who are, are in key positions are getting 20, 30% cuts, even if they are the key player. And they're irreplaceable.

• 16:43Gary Vaynerchuk?

  It's kind of like this. I said, somebody said to me, Gary, that's not fair. I'm like, let me give you an analogy. You are, you are in a forest, a tree falls on you, and it's on your leg. And you sleep there for a day and you're in big trouble. And a ranger comes along and tries to help you. And she says to you, listen, you're gonna have to cut off your leg to, to live. You're cutting off your leg. We don't, business owners and, you know, funds and banks, they don't want to, and companies, they don't want to lay these people off. They're their legs. They love them. If, if everything was okay, they wouldn't have. They don't want to ask all their executives to take a 30% decrease, but that's cutting off your leg. Otherwise, you die.

• 17:22Lewis Howes?

  Yeah.

• 17:23Gary Vaynerchuk?

  People are just so funny with this kind of like ideology, like, okay, or the business goes out of business.

• 17:30Lewis Howes?

  Yeah, we have no money. Yeah.

• 17:32Gary Vaynerchuk?

  Yeah.

• 17:32Lewis Howes?

  What's been your biggest fear in all of this? Or do you feel like you're pretty fear-proof at this moment with everything you've been through?

• 17:38Gary Vaynerchuk?

  I'm fear-proof because I'm willing to go to zero.

• 17:41Lewis Howes?

  Yeah. You can live on a small apartment and, you know, live at your parents' house.

• 17:45Gary Vaynerchuk?

  I really can, man.

• 17:47Lewis Howes?

  Yeah.

• 17:47Gary Vaynerchuk?

  I don't know what else to say. Like, this has proven it to me even more. You know, any .0001% of me that thought, well, I've been saying this for the last two years, am I full of shit? Has completely gone away.

• 17:59Lewis Howes?

  Yeah.

• 18:00Gary Vaynerchuk?

  Like, I just, I don't fear because I don't value things and money. My biggest fear is my parents getting sick. Like, my biggest fear is, like, somebody getting sick and dying, nothing else. Like, business, I can always, like, I'm too capable, right? Like, you know, back to, back to the thing you brought up, back to why you were an Olympian, back to like, why you beat me everything, anything, when we were on Summit at Sea.

• 18:26Lewis Howes?

  Basketball.

• 18:26Gary Vaynerchuk?

  Whatever, basketball. You aren't worried when, when it comes to sport, you know, your, your mind just goes into, this is gonna be a good situation for me.

• 18:37Lewis Howes?

  Yeah. I feel comfortable.

• 18:39Gary Vaynerchuk?

  Yeah, and for me, that's business. Like, I know for a fact that if I became a 100% full-time garage sale, thrift store, Amazon flipper, that I'd make a million dollars a year. I, I, I know that for a fact. So what the hell am I, and that doesn't take into account that I am, that I've built a brand. And sure, my brand would take a hit if I, all my businesses went to zero, but the reality is, America's funny, man. Like, there's people following and helping OJ Simpson. There's, you know, Wolf of Wall Street. Like, like, this is a country that gives second, third, fourth chances regardless. And so, like, I'm already at a place right now where between brand and capability and humility,

• 19:20Gary Vaynerchuk?

  I'm bulletproof. I believe that.

• 19:22Lewis Howes?

  This is a question from one of my audience members that, um, asked me, his name's Chris Turcot.

• 19:27Gary Vaynerchuk?

  Chris. Oh, I know Chris.

• 19:29Lewis Howes?

  Chris Turcot, I think his last name is. He said, uh, he doesn't hear you talk about this much. Favorite thing about being a father?

• 19:38Gary Vaynerchuk?

  That all the good things that I'm doing for the world with my advice and my wisdom, I get to actually do for a human that's gonna get the purest execution of it, deepest execution of it, and I get to watch it from coast to coast. And so, and just like, and just like, pure love, right? Like, like, my daughter got a fifty-three out of a fifty on a Spanish test, so we went to get the, you know, check in on the school stuff. Like, I'm bringing it up right now, the pride was like, and remember me, right? Like, fuck school, like, that's her game, and it works for her. And I just sat there and I was like, you know, like, every parent that's listening out right now knows,

• 20:20Gary Vaynerchuk?

  they're blown away by the pride that comes along with a child. And then, and then just really knowing that I also have my own self-esteem. So, one of my favorite parts is knowing that I'm not gonna f*** up from making them do things. Like, if my kids are, if they start nonprofits and give away all of the family's money, I'm gonna be proud of them, as long as they're happy. I don't need them to be an entrepreneur. I almost, I almost don't want my kids to be entrepreneurs, 'cause I don't want them to have to live in the shadow or try to climb the mountain I'm creating now.

• 20:51Lewis Howes?

  The pressure, the pressure of like, living up to dad, yeah.

• 20:54Gary Vaynerchuk?

  I mean, look, you know, we're not, we're young. Like, you know, my, my little guy is turning eight in August. Like, in ten years, he's eighteen. You and I hang out with eighteen-year-olds in business. How old are you right now?

• 21:05Lewis Howes?

  Thirty-seven.

• 21:07Gary Vaynerchuk?

  You're gonna be forty-seven, slightly older than I am right now, and you're gonna know Xander for real.

• 21:13Lewis Howes?

  Right, I'm gonna be like, working with him.

• 21:15Gary Vaynerchuk?

  Exactly, and, and then, if, you know, if the way the chemicals played out, if he's not of my entrepreneurial cloth, that's gonna run through your mind, just like it does with me, with other... I mean, I've met a lot of famous people, accomplished people's kids, and, and I don't, and I don't even like judgment, and don't even think about it, but I'd be lying if I didn't say, after you have a meeting with somebody, you're like, "Oh, okay, that's how they're different than their mom," or their dad, right? It's so cliche, and so like, I want them to be happy. And if, by the way, if they do what I do, which is, I looked at my dad, and by the way, coming from zero and looking at what my dad... Dad built, you know, in our little Russian community, that was a big deal and I wanted to climb that mountain and build. And if my kids look at my bigger mountain and say, I'm going to climb that mountain, I'm going to cheer them on.

• 21:56Gary Vaynerchuk?

  Slash, not big the outcome. They're not getting a $50 million check. They're not getting a $5 million check for me. They're gonna, they're gonna get the relationship graph, which already gives them a huge upload because Uncle Louis is going to give him a hundred thousand for their. But you know, I'm, listen, there's no way to completely create fake environments unless they want to do the John Travolta, you know, Nicolas Cage face rip thing and change your name. So, but I, I definitely think that the best part is just building it, just like a business. Building that relationship, but building it with hands off instead of building it with hands on. I think parents build too much with hands on.

• 22:30Lewis Howes?

  Would you want your kids to repeat your same insane amount of work ethic?

• 22:35Gary Vaynerchuk?

  If that makes them as happy as it makes me.

• 22:38Lewis Howes?

  Yeah.

• 22:38Gary Vaynerchuk?

  And I want them.

• 22:39Lewis Howes?

  You wouldn't want to expect it from them though.

• 22:41Gary Vaynerchuk?

  No, I don't expect it from anybody, to be frank. I think I'm, I'm really in rarefied air of like, deep obsession with my process and enjoyment and lack of anxiety from it and lack of burnout from it. I think I hit my crescendo. I think I'm more of an artist. I, I don't think people realize that business women and men are actually, uh, there's a certain version of us that are artists that genuinely like this more than anything.

• 23:07Gary Vaynerchuk?

  Like, like we, like singing, like Beyonce's a workaholic.

• 23:10Lewis Howes?

  Yeah.

• 23:11Gary Vaynerchuk?

  You know, like Kobe was a workaholic.

• 23:13Lewis Howes?

  Obsessing over their craft, their art form, their expression, yeah.

• 23:16Gary Vaynerchuk?

  So for me, like, like we demonize it in entrepreneurship and corporate life, but we don't in art. We, we put artists, we put, oh, he's in the studio all the time. Wow. You know, painting all the time. Wow. Cooking and traveling the world to buy food. Wow. Business, oh, he's going to burn out. He's going to suicidal.

• 23:35Lewis Howes?

  Why is that? Is that just because of the old way of thinking, like getting burnt out in the corporate world of doing a job you hate?

• 23:41Gary Vaynerchuk?

  Yeah, money, money. We, you know, I don't think people, like Mark Texier made $213 million playing baseball. But if some entrepreneur makes 30 million, they get demonized. It's just culture. It's just culture and it's okay. Like I don't, I don't think that's wrong, right or indifferent. It's just the obvious observation, right? We demonize the startup founder or the businesswoman much, much more than the entertainer that makes way more money.

• 24:05Lewis Howes?

  What was the greatest lesson that you talk about your parents a lot, which I think is amazing that you constantly speak about them as your mentors and heroes.

• 24:15Gary Vaynerchuk?

  Yeah.

• 24:15Lewis Howes?

  Even now, it's not like you said it a few years, you say it every day or week.

• 24:19Gary Vaynerchuk?

  Cause it's true.

• 24:20Lewis Howes?

  What is the greatest lessons that they taught you about you being who you are now? Which I already know the answer, but I want everyone else to hear. And what is the thing you wish they would have taught you that you teach to your kids a little bit differently?

• 24:32Gary Vaynerchuk?

  Very, I do think my parents for me, and they parented all three kids a little bit differently, but like, but they're like, they really, they were such workaholics, both my mom, my mom was a stay at home mom, but like, did everything. Like, you know, like, like, you know, and I think people very much underestimate stay at home moms as workaholics. Like she just worked her face off, no help.

• 24:53Lewis Howes?

  No breaks.

• 24:54Gary Vaynerchuk?

  No breaks. We were all spoiled kids from the fact of laundry and doing our bed. And she cooked everything and like, and then my dad came home late because and cooked for it like she worked her face off. So they could have created a little more balance. We only took two family vacations. So they taught me work ethic, kindness, everything, everything I am is then. But I do think the thing that we have more is balanced with, you know, leisure and, and offsetting 24/7 work. But they, that makes sense. It's generational. They came here with nothing and it was 24/7 work. And I have so much of that in me, but I've had the luxury of my talents leading to a success. That's allowed me to post, you know, listen, that's how my first 10 years professionally looked too.

• 25:34Gary Vaynerchuk?

  But now being able to take a little bit of time and so maybe a little balance because I think they regret that. And, and so you try to take your parents regrets and not have the same. And so I, I look at that.

• 25:45Lewis Howes?

  That's cool.

• 25:46Gary Vaynerchuk?

  But kindness, kindness, my mom instilled kindness, like, you know, some of the stuff you started this show with. And they both instilled work ethic and my dad, my dad, um, you know, just genuinely like just willed his way into success. And I think I have a lot of that as well.

• 26:02Lewis Howes?

  Yeah. Now, over the years, people have seen you, uh, daily vlog for years and just post about your entire life.

• 26:09Gary Vaynerchuk?

  Yep.

• 26:10Lewis Howes?

  And I think, I think we did an episode three or four years ago together. I think you've been on a few times now. And we talked about the idea of balance from like business to family. And I remember people being in awe of the responses you had around this at that season of your life. I'm curious now, how do you find the balance between being a great husband, between being a great father, having great health, and building a great empire? And what do you feel like you could improve more in at this season of life?

• 26:38Gary Vaynerchuk?

  You know, I think, I think, you know, back to extremism, right? Like extreme, which I use, I, you know, all of it can be better and all of it is just great. I, I think, you know, here's a good place to go with this, let's really bring value. So you can go back, you know, four years ago and listen to like how I think about extremism going hard and then vacationing hard and it's all there. I think what this has evolved into is something a little bit deeper and more important that I hope really brings somebody value right now, which is, stop beating yourself up and stop judging yourself. We all go through chapters, right? Like sometimes you're super in love with your partner and like that's all you can obsess about, you know? It feels like that's, you've been through that chapter recently.

• 27:20Gary Vaynerchuk?

  Like other, other times you're, you know, super into your profession because you got a new initiative and you gotta go, it's another baby, sometimes it's an actual baby. And, and, and by the way, for some people, the first two years are actually super boring because the baby does nothing and it's okay to not be like blown away and spending every second. On the flip side, if you just can't believe this little miracle and you need to like cut, work out, like I think this comes down to judgment, stop beating yourself up, there is not even a close framework for what's right. Everyone's balance is massively individual and more importantly, balance ebbs and flows forever. For example, my kids are starting to get into, I'm like, oh, oh, they're gonna be teenagers one day. Like if they double their age, you know, all of a sudden they're 20 and 16 and I'm like, what?

• 28:05Gary Vaynerchuk?

  Like, you know, like, and, and immediately I go to things like, Oh, they can go on business trips with me. Wait a minute. They're gonna just take an Uber and I'm gonna sit courtside with my little guy and my daughter, because she's really into basketball as well, like often. Like, I'm gonna see them two nights a week. Oh, that means my Nick courtsides are gonna convert from business to 50% personal, which is gonna mean now all of a sudden it's Tuesday and Wednesday. You know, like, technology, like FaceTime culture, I've exploded by FaceTime interaction with them. And so, like, those kind of things.

• 28:38Lewis Howes?

  Yeah. How does Gary eliminate self-doubt and self-sabotage? When it seems like there are so many wins that you hit, but also people don't see all the big losses that you have as well and the risks and the...

• 28:52Gary Vaynerchuk?

  Yeah. I've loved myself the whole time, thank God. Most don't. But I haven't allowed me to get high on my own supply. My humility is my great offset to my confidence. And I think that manifests. And I think one of the things you were saying, when you were saying it, I knew what you were saying, which is you have the luxury of seeing really behind the scenes, truly.

• 29:14Lewis Howes?

  Yeah.

• 29:14Gary Vaynerchuk?

  And I think what you know is, forget about giving to a nonprofit, it's just the genuine kindness of replying to somebody's request or doing something for somebody with no ask, no expectation, and nobody knows. And you know this because you run in entrepreneurial circles like I do. And you know when you stumble on somebody who knows me as well, they're gonna bring up something that I did that was nice and nobody knows about it. And that is only one thing. That is called humility. That is not reading your press clippings. That is not thinking you're somebody. And I think I have deep love for myself, which leads to huge confidence. But I'm practical. So I don't try to overextend myself, which should keep me away from being losses. But there is no doubt. Like, I think things through. And if I lose, I lost.

• 29:58Gary Vaynerchuk?

  But I'm never doing anything for any other reason than I think it's right. And that leads me to a place where I'm not very vulnerable. Because when you start doing things to impress the girl, or to keep up with the Joneses, or you're jealous of somebody else's success, and you want to close the gap on their net worth, on their Google search, or all the dumb shit that people are thinking about, you become vulnerable. I mean, so many people over... I mean, listen, there's some big personalities that are gonna get smoked out. Over the next 12 months that like have played the part on Instagram, they're gonna lose. They just are.

• 30:29Lewis Howes?

  I also think if you're focused on like chasing the money game of competing against someone financially.

• 30:35Gary Vaynerchuk?

  Oh.

• 30:35Lewis Howes?

  And you make the wrong decisions, then you start to take things personally, get defensive, get angry at people that aren't making you money or whatever. It's just everything becomes an attack. So if you lost a, if you, let's hypothetically say if you lost a million dollar bet on a business or an investment or whatever and.

• 30:50Gary Vaynerchuk?

  I've got, I've got one that's gonna happen soon. So go ahead.

• 30:53Lewis Howes?

  And it went to zero.

• 30:54Gary Vaynerchuk?

  It's going to.

• 30:55Lewis Howes?

  How do you tell yourself, I still love myself. This doesn't, you know, affect my self-confidence.

• 31:01Gary Vaynerchuk?

  Because I knew the vulnerability was other people. I did the most I can. I was stretched in more than I wanted to be, which didn't allow me to really fix it along the way. I just didn't have, you have too many plates in the air and I focused my energy on things that are so fruitful that are gonna offset that million loss. It's an L. I don't want it, but it's real.

• 31:20Lewis Howes?

  Wow. And I think also, do you go into the mindset of knowing like this could be a hundred million or it could be zero and you're okay if it's zero? Or do you still?

• 31:28Gary Vaynerchuk?

  I go into everything thinking it's gonna be zero.

• 31:30Lewis Howes?

  Really?

• 31:31Gary Vaynerchuk?

  Yeah. It really makes it, why do you think, notice, doesn't make sense now all of a sudden? I go in with no hope.

• 31:38Lewis Howes?

  No expectation.

• 31:39Gary Vaynerchuk?

  No expectation. I mean, I don't do it for my kicks and the giggles. I think, I think it's gonna work.

• 31:45Lewis Howes?

  Yeah.

• 31:46Gary Vaynerchuk?

  If I'm running it, it's gonna work because that's what I'm good at. But almost everything I don't run. I don't run, I don't run Pure Well 137 and Harwood does. I don't run Vayner Sports. AJ does. I don't run Vayner Speakers. Zach Nadler does. I'm impacting the living shit out of those businesses.

• 32:01Lewis Howes?

  Influencing them, yeah.

• 32:02Gary Vaynerchuk?

  Oh, in a real way.

• 32:04Lewis Howes?

  Yeah.

• 32:04Gary Vaynerchuk?

  But, you know, push comes to shove, I don't make those decisions and so, um, and I support my partners in crime. And so that's kinda how it is.

• 32:13Lewis Howes?

  Yeah. Over the, I think you start, when did you start Vayner Media? Was it 2010, 2011, 2009? So I, I was in the office, I think it was Soho when there was like six people in there on a ping pong table.

• 32:24Gary Vaynerchuk?

  Sunshine Suites.

• 32:25Lewis Howes?

  And I remember at one point, it must've been 2011 or 12.

• 32:30Gary Vaynerchuk?

  That's right.

• 32:31Lewis Howes?

  When you said somewhere in an interview, maybe it was with me or somewhere, a speech, you said, you know what? We were okay as an agency the first couple of years. Like, we actually were like, not that good. I think you even said like, "We were okay, we weren't great." But now we're really like, we're great. After three, four, five years of in the business. What would you feel like is the thing that you regret the most over the last decade? Or one of the hardest challenges within the agency that you had to face? Maybe that's two questions there.

• 33:01Gary Vaynerchuk?

  No, there's several things there. One, the biggest challenge I had to face was about year six, seven, six. I was creating entitlement because I was putting too much on my own shoulders.

• 33:12Lewis Howes?

  What do you mean by entitlement?

• 33:14Gary Vaynerchuk?

  I was making it too easy for everybody and people got entitled.

• 33:18Lewis Howes?

  Within the company?

• 33:19Gary Vaynerchuk?

  Yep.

• 33:20Lewis Howes?

  So you were saying, "I'll take this on, I'll take this on."

• 33:23Gary Vaynerchuk?

  In the macro. I was creating so much top-line revenue. And everybody was getting raises like crazy and I was creating such a great culture that I made us soft. Which is wild.

• 33:33Lewis Howes?

  Because you were doing the sales and the pitching and everything yourself?

• 33:36Gary Vaynerchuk?

  I was impacting so much that that 300, 400, 500 people had it too easy. And we had to do like a 35-person layoff because I just had to cut the fat. Because I just, and I didn't need to do it financially, I needed to do it to just culturally get everybody to understand. Like, these people that were just like, "Oh, weren't good at their job." They were nice people, but if we keep carrying this, this will die.

• 34:00Lewis Howes?

  They weren't great at their job, they were...

• 34:02Gary Vaynerchuk?

  Not even close. They weren't even close. Like, it was nice people over everything and that was it. If you weren't nice, you were getting fired. But if you were nice, like, it was, and it was, that was tough. And it was tough for me to realize, wow, on Tea with Gary Vee, on keynotes, and interviews, on the stage, I have great candor and accountability, but in my own shop, I wasn't candorous enough. And I created entitlement because I love happiness and la-la and yea-yea and all that.

• 34:32Lewis Howes?

  And everyone loving you, yeah.

• 34:33Gary Vaynerchuk?

  But I went too far with it. So that was tough. That was a moment. Because I never got to that level with... Wine Library, because it was still happening there, but it was a small enough business and a family business. And it was real family cousins and best friends that had a different dynamic. So I didn't see it coming. So that was, that was interesting. Uh, AJ leaving was tough.

• 34:55Lewis Howes?

  I was gonna say that was, that's what I thought you'd say there. Yeah.

• 34:58Gary Vaynerchuk?

  That was a big blow. I didn't see it coming.

• 35:00Lewis Howes?

  You guys built this together. This was 50 50. This was, we're gonna grow this as a empire, the family.

• 35:06Gary Vaynerchuk?

  Yep, yep. And like being with my bro and all that. And, and so that was rough. He left for anybody doesn't know, because he has Crohn's disease and he just wasn't feeling great, to be frank. He just didn't like the business enough. Clients are shitty. Client service business suck. Um, and he just sent him out. I don't feel well. And so that was rough. And that whole process was rough, like buying him out and like, you know, we were 50 50, but I, I, you know, what I love about my brother is I'm sure if he sat here, he would say, that wasn't how it played out. We didn't know how it was gonna play out. So those are dynamics of like, you know, like, that was rough. That's just real talk, you know, but like, we're obviously in an incredible place, thank God, because we genuinely love each other more than money.

• 35:47Gary Vaynerchuk?

  But it's still, you know, you have your, your true, it's not even egos. You have your own merit. You know, radars that kind of feel like, what is the situation? So unwinding that is always tricky. I'm so grateful that we're in such a great place with each other. And we, by the way, for the record, we were never in a tough spot. Me and my dad were in tough spots all the time because of the two cooks in the kitchen. Me and AJ, like really figured it out and we really leaned into each other. So that was good, but that was challenging. Um, this, this two months has been really challenging because, you know, I structured for economy break, but not one that was, the whole world had liquidation issues and speaking went to zero.

• 36:27Lewis Howes?

  Oh, man.

• 36:28Gary Vaynerchuk?

  You know, like just a lot of things that, you know, production, which is a big part of us, went to zero. You know, and clients aren't paying like, you know, so it was like, you know, I was super prepared for 2008. I was not prepared for something that looked like this. We got lucky and I hate using that word, but this is the truth. If Hilton and JetBlue and and Morton Steakhouse were my biggest clients, we would be in real trouble. Like luckily for us, food and like the serendipity of like financial services, food, beverage, being our biggest clients is is gonna let us get through this in a good way. Uh, when it's all said and done, but but we could have gotten like, honestly, I sit here and say, my God.

• 37:07Gary Vaynerchuk?

  If Marriott, Hilton, if American Airlines, if, yeah, I'm trying to think of other people, clothing, if if Neiman Marcus.

• 37:14Lewis Howes?

  Retail.

• 37:15Gary Vaynerchuk?

  You know, retail, like if our product, if our client mix was different. This would have been maybe it.

• 37:21Lewis Howes?

  Really?

• 37:22Gary Vaynerchuk?

  Really. I mean, if you go, if all your clients go to zero and you're in client services, you're not selling wine, you're not selling, you know, subscription business. You know, if you, there are agencies that have gone out of business because of this, because because, you know, yes, I mean, you know, nobody could ever think of zero, zero. But but by the way, I've always thought about war. This is the closest thing to war. I've always thought about like, what if World War III happens? But what my mind would always go is like, well, you don't care about business, then you're actually genuinely scared of a bomb or dying or whatever it is. So, this is like war without war, real life. Now, what's really cool about that is that happened. Let's say Hilton and American Airlines and Chuck E. Cheese, I'm trying to think of a million different things and and sports, what about that? The Jets and the NBA.

• 38:06Gary Vaynerchuk?

  All these, the serendipity that's like, we just got the perfect wrong hand, three, seven offsuit. I would have been super, I'd be make doing this video and be like, that's what happened. And and I couldn't see it coming and I deserved to lose. Like literally, that would be like my reaction to it.

• 38:20Lewis Howes?

  Yeah, and you'd almost be excited to start from

• 38:22Gary Vaynerchuk?

  Oh, so excited.

• 38:23Lewis Howes?

  You always talk about, I wish something happened so I could build it back up again. How how much has your business been affected? Have you lost, you know, half your clients or 10% or?

• 38:33Gary Vaynerchuk?

  Maybe, uh, we're definitely 12% down in like top line revenue expectations. We've had, we have, I I still don't think this is over. I think there could be a, you know, relapse and that would trigger things. We pay liquidity more than revenue. People are stretching terms. They don't have the money. Like there's, you know, that's

• 38:53Lewis Howes?

  What are you doing?

• 38:54Gary Vaynerchuk?

  And I'm paying my employees.

• 38:56Lewis Howes?

  Yeah.

• 38:56Gary Vaynerchuk?

  And I'm paying rent.

• 38:57Lewis Howes?

  From, exactly. That's tricky, man. You gotta get Higgins to give you a little break on that rental.

• 39:03Gary Vaynerchuk?

  Yeah, the problem is even Ross, like, he has partners in banks and it doesn't work that way. And so, and by the way, my business is too big for the little bailouts and too small for the big bailouts. So I'm in that perfect middle, like us 50 to 300 million dollar businesses are the ones that are gonna go out of business.

• 39:20Lewis Howes?

  What are you doing personally to supplement the speaking fees?

• 39:25Gary Vaynerchuk?

  Nothing.

• 39:26Lewis Howes?

  Nothing. Are you innovating anything to launch or create?

• 39:30Gary Vaynerchuk?

  No, I'm massively tripling down on, you know, empathy is doing really well. So, you know, empathy wine's doing well, so my wine business and my dad gets all the income from the family business. So that's, I'm doing wine techs because I love them and it's fun, but that's not hitting my pocket. And I'm focused on VaynerMedia. I gotta make sure VaynerMedia gets through this properly because when it does, it'll be two times bigger. Because we're built for this kind of world. So this is, this is why savings matter.

• 39:59Lewis Howes?

  It's so important why savings matter. It's something I remember in 2008 when I was on my sister's couch. I remember saying to myself, never again do I want to feel broke, like I need to go back to my sister's couch. Like, hopefully there's enough time where I can be smart enough to not buy. I wear the same $20 shirt probably like you every day. I'm not out buying stuff. Like, I like to feel good, but I don't need to buy fancy things. I'd rather have money or investments or something that I could use for a time like this.

• 40:25Gary Vaynerchuk?

  Yeah, but a lot of, you know, most of my, most of my net worth is tied up in non-liquid investments, right?

• 40:29Lewis Howes?

  That's true.

• 40:30Gary Vaynerchuk?

  So, you know, investments is fine, but like the one thing that made me feel good from day one is I have a certain amount of money in the bank that like, that is just to me like, do not touch and like I feel I can live on. And again, if everything went to zero, that's not the case and that's why I'm focused on this. But if everything went to zero, I would start looking at that and like literally sell homes and like rent a little apartment and use that capital to start my flipping empire. Because that's what I would do on the record. If that ever happens, I'm gonna buy and sell shit because that's my core, basic. Skill set that is liquid on the transaction. I mean, I mean, Lewis, you know this, like, I've been yelling for a year and a half about sports cards. They've gone through the roof.

• 41:10Lewis Howes?

  I know. I feel pissed that I didn't get any MJ cards after this.

• 41:13Gary Vaynerchuk?

  Told.

• 41:14Lewis Howes?

  Uh, I feel like, you told me a year ago, you're like, get LeBron, get Jordan, get all this. And now it's going up because of this stuff. I'm curious.

• 41:20Gary Vaynerchuk?

  Really? Jordan rookie cards went from 20 to 100,000.

• 41:23Lewis Howes?

  That's crazy, man.

• 41:25Gary Vaynerchuk?

  Like, everyone's like getting into startups. I was like, I put my, you know, like, LeBron rookies I bought for 1100 or 7000.

• 41:30Lewis Howes?

  Oh, man.

• 41:32Gary Vaynerchuk?

  And when you buy 55 of them, that's money.

• 41:35Lewis Howes?

  That's money. I'm curious. We talked about how you overcome self doubt. How would you inspire other peoples or educate them on how to eliminate self doubt in their life?

• 41:43Gary Vaynerchuk?

  It's completely, it's completely predicated on valuing other people's opinions. If you actually make pretend nobody else lives on earth, nothing is scary.

• 41:53Lewis Howes?

  Why is the opinions of others such a heavy thing for people to overcome?

• 41:57Gary Vaynerchuk?

  I think it's humanly, like, this is where I think, like,

• 42:01Gary Vaynerchuk?

  this is truly my, my great gift. I'm so grateful for it. I think people got caught. I think they just get caught that everybody's in this framework of other people's opinions, like, just, it's how we're raised.

• 42:14Lewis Howes?

  How do we train ourselves to get out of it if it's something for 10, 20, 30 years, 50 years, we've been living that way?

• 42:19Gary Vaynerchuk?

  The same way I trained at 38 and a half, that I have no way taking care of my health. I don't like eating habits. I don't like exercising. And just pounding, pounding, pounding, pounding. Every day, everybody should, this is why I put out so much content. Maybe today's the day that I say it a different way that makes people realize their mom and their girlfriend and their boyfriend and their uncle and definitely anonymous people on social media and Lewis and Gary's opinions actually don't matter. Wow, the liberation to then actually do shit. And now you're doing shit full throttle because of whether you win or lose, it doesn't matter. You can't hear the cheering. This is why I'm trying to get people out of hearing the cheering. It's my newest thing in the last year or two. I'm like, wait a minute, right? Because everybody says you're so hot on Instagram that when they say you're not,

• 43:03Gary Vaynerchuk?

  you start doing plastic surgery, right? When everybody says, like, you're such a great business person, you start keeping up that facade instead of like, it just makes so much sense. So to me, the biggest thing is the humility was such a factor. I didn't realize how big of a deal that was, how much that worked for me is like, I don't believe I'm as great as I know I am. Like, my logical side knows that I'm up to something, but I just don't internalize it. I won't let it penetrate my soul. I think I have the ability to be the biggest deal, but I will never believe it.

• 43:35Lewis Howes?

  That's powerful.

• 43:36Gary Vaynerchuk?

  Yeah, I think, you know, even I've never said it that way. Like, I'm like, thank you. I was like, literally when you, and I gotta clip that for Instagram. Like, you know, like, like, that's what it is, man. I really genuinely think, and you know this about me, like, I think I can be the guy. Like, I think Bezos and Zucks and Elon will make so much wealth during this time. But I think the way I'm going about it, I think I can be that entrepreneur's entrepreneur when it's all said and done in the end. And I think, even if you look at what's happened with me, you've been along for the ride. Like, over the last two or three years, I can feel, I know, because I'm a branding guy, like, the brand is in a different place.

• 44:11Lewis Howes?

  It is.

• 44:11Gary Vaynerchuk?

  I've separated a little bit. You know what I mean?

• 44:13Lewis Howes?

  Yeah, you have.

• 44:14Gary Vaynerchuk?

  And I'm like, okay, well, I'm 44 and I'm like, fucking, you know what I mean?

• 44:19Lewis Howes?

  I love the stories of like Colonel Sanders at 50 launching KFC.

• 44:23Gary Vaynerchuk?

  Yeah.

• 44:24Lewis Howes?

  They take off at 50. It's like, you're just getting started.

• 44:27Gary Vaynerchuk?

  Sidney Frank started Grey Goose in his 80s.

• 44:29Lewis Howes?

  You haven't even got started yet. This is the preseason.

• 44:32Gary Vaynerchuk?

  By the way, I think I said something similar to you on a personal note not too long ago. Because I remember thinking, like, watching you from afar, like, the ebbs and flows. Like, you know, a lot of times, I was on an interview the other day and somebody said, Gary Vee, you did a really, really good job. You know, you were super early on podcast, you know, saying all this stuff. And I said, oh, stop on podcasting, because my homie Louis and, you know, and some of these other characters, Jordan, and, you know, all these are the charm, right? And Pat Flynn and others, Dumas, right? Like, others, like, they were a little earlier. Ferris, like they were earlier, I'm like, I did, I've done a fine job. And, and so I think about you, because we're friends, and I'm like, okay, he really wanted, like, podcasting was that thing that took you to the next place.

• 45:14Gary Vaynerchuk?

  You know, and obviously I made the, the, uh, nice reference earlier, like, I love seeing you being in your relationship life, you're putting that out there a little bit. And now I'm like, okay, you know, you know, you know, it's just fun to think like, I wonder what if, what if, what is it gonna be, or is he, like, where is he in his life, like, is he gonna have another chapter? And that's what's fun about this, right? Like, when I think back to like, early, you know, Twitter, like Chris Brogan, right? Right?

• 45:38Lewis Howes?

  He was big, Guy Kawasaki and Twitter.

• 45:40Gary Vaynerchuk?

  Right, right, and, and both of them are still doing their thing. Everybody does different things, though, right? Like, some people, those two haven't, others completely disappeared. And the reason I'm not bringing them up is because they disappeared because they weren't good in their soul or their capabilities. And I remember thinking in oh nine, ten, eleven, when I was popping for the first time, I'm such a loud mouth, I'm so much, I have so much energy, I cursed. I remember knowing, and this was absolutely true, a lot of people thought that I was gonna be kind of like this phoenix of like, and then disappear, because it just didn't seem, quote, sustainable.

• 46:13Lewis Howes?

  Yeah, yeah.

• 46:14Gary Vaynerchuk?

  And I remember thinking, man, I, I remember then, thinking, wait till they see in ten years where I sit. And, and it's happened, and I think, and I think, man, wait till people see where I'm gonna be in ten years from today.

• 46:25Lewis Howes?

  You're just getting, I feel like I'm, I feel like, okay, I spent the last ten years of

• 46:29Gary Vaynerchuk?

  Foundation work.

• 46:30Lewis Howes?

  Researching, like, trying stuff, making mistakes, some things working well, like, figuring it out, reinventing, really trying to find my true lane.

• 46:38Gary Vaynerchuk?

  Yeah.

• 46:38Lewis Howes?

  And, okay, now I can get started.

• 46:40Gary Vaynerchuk?

  Yeah.

• 46:41Lewis Howes?

  You know, it's like, all right, now let's do something cool. And let's build off of what we built with the personal brand and leverage it.

• 46:47Gary Vaynerchuk?

  Look, look what I did in eleven, I went all in on VaynerMedia, everybody thought I was stupid, why didn't I raise a fund? Why didn't I start a startup? It seems super left field, but a lot of those homies in Silicon Valley, their startups failed and are gone now.

• 46:59Lewis Howes?

  Right, they're too big about valuation and now the stock.

• 47:02Gary Vaynerchuk?

  And now, and now I have a marketing foundation that's a fucking supernova.

• 47:05Lewis Howes?

  You can launch anything.

• 47:06Gary Vaynerchuk?

  Anything.

• 47:07Lewis Howes?

  You've got the engine to launch a product.

• 47:09Gary Vaynerchuk?

  Empathy Wines is a meaningfully successful, direct-to-consumer wine brand that, that John and Nate run.

• 47:16Lewis Howes?

  It's crazy.

• 47:16Gary Vaynerchuk?

  Interns.

• 47:17Lewis Howes?

  Software and a couple of interns.

• 47:19Gary Vaynerchuk?

  Yeah, but they were interns, now they're ten years under my watch. Now they're executives.

• 47:24Lewis Howes?

  Wow, ballin'. What is the, um, you mentioned earlier, you know, client work is shitty. And agency work is shitty.

• 47:31Gary Vaynerchuk?

  It is.

• 47:31Lewis Howes?

  Why put your life's attention into shitty business model essentially?

• 47:36Gary Vaynerchuk?

  Because, because I'm building the Death Star. I'm sure the Death Star was shitty to build for, you know, Darth Vader and the Emperor and all that. But when it was done, it could press a button and blow up a planet. It wasn't fun for me to eat shit in the prime of my career, except here I am at forty-four. Empathy being the first one. The rest of my life are gonna be the next ones, including Lewis for governor in California. Including, let's cure Crohn's disease because AJ has it. Including many other things. So I'm building a Death Star. I'm building a Vayner, and it's VaynerX now, right? It's got the publishing side, it's got a speaking bureau, it's got, it's got, uh, you know, a tracer dot tech. You should, people should check out, it's a data analytics SaaS business.

• 48:20Gary Vaynerchuk?

  It's a, it's got, you know, the Sasha Group for small businesses. I'm building literal mass.

• 48:27Lewis Howes?

  Machine.

• 48:27Gary Vaynerchuk?

  Machine, that's the scalable version of who I am as a human.

• 48:31Lewis Howes?

  It's amazing.

• 48:32Gary Vaynerchuk?

  Like, Vayner Publishing would be a top book publisher if I decide. Vayner Real Estate, I would be a major broker. You know, Vayner anything in perpetuity now that I've eaten dog shit for a decade.

• 48:46Lewis Howes?

  If you could predict, uh, what was your prediction ten years ago when you launched Vayner Media? Was it to be where you're at with whatever six, seven, eight hundred employees and kind of?

• 48:54Gary Vaynerchuk?

  It was, I did think by now I would have one brand owned and because I thought the economy would collapse earlier.

• 49:01Lewis Howes?

  Like a shoe deal, because you were to buy like a, some type of shoe.

• 49:04Gary Vaynerchuk?

  It's why, it's why I did, it's why I did the K. Swiss thing, right? It gave me a chance to test it when I realized I wasn't gonna be doing that just yet. And it came in front of me and I did it and it really worked and they sold that. Look at Resy, Resy had a.

• 49:17Lewis Howes?

  Big exit, right?

• 49:18Gary Vaynerchuk?

  Resy's my biggest exit, I never talk about it, I co-founded it.

• 49:22Lewis Howes?

  Wasn't that a two hundred million or what was that?

• 49:24Gary Vaynerchuk?

  Yes, plus. So like, I'm winning out here, like, Resy's kind of like the, like.

• 49:29Lewis Howes?

  I remember Resy and being like, it came out hot and then it kind of like, you didn't hear about it for four years and then, oh, it just exited.

• 49:36Gary Vaynerchuk?

  It was the winner, it beat Reserve and Reserve had all the Uber guys and gals behind it. We won, but we just built a business. It wasn't like, I'm not out here worried about making sure it's in the headlines every minute. Like

• 49:48Lewis Howes?

  Why not talk about that though? Why not talk about like the thing that you launched and it was a big hit?

• 49:53Gary Vaynerchuk?

  It's just not on my mind. Plus Ben Leventhal and Mike Montero, the CTO, deserve a lot more credit to me. I came up with the idea jointly with Ben. We, I found Mike Montero, who was a big time CTO that built the incredible product. I personally wrote a big check when the company was in trouble at one time. I did a lot of great things, but I'm a fan of the operator.

• 50:11Lewis Howes?

  They executed day to day.

• 50:13Gary Vaynerchuk?

  Uh huh, uh huh. So I don't like to go out there because I think that's faking the funk a little bit, but I feel like my DNA is really in it. And I feel like in comparison to a lot of other people that have a lot of wins that they claim, I have plenty of my DNA in Resy. But that is Ben most, most, first and foremost, that's Ben's win.

• 50:29Lewis Howes?

  So, okay, so you didn't reach that level of what you thought would happen within this decade, but it's 2020 now. Imagine 2030. What do you want to see happen by then?

• 50:39Gary Vaynerchuk?

  I thought I was gonna build like us, I thought I was gonna build the millennial Falcon and buy, you know, K Swiss. What ends up happening is building the Death Star. And so when I buy Puma and, and then flip it 12 years later, I buy Puma at 54, 10 years from now. I flip it at 64 and I buy the Jets and win six Super Bowls. Like this has been written, Louis.

• 51:01Lewis Howes?

  Give me the, the year and the date and the time that you're gonna sign for the Jets. What is the exact time, date?

• 51:08Gary Vaynerchuk?

  Uh, November 11th, 9 a.m. November 11th, 20, uh, what do we mean 2020? 2048.

• 51:18Lewis Howes?

  Wow, I'm marking it down. November 11th, 9 a.m. 2048. What is it that day and time? Does that have any meaning with you?

• 51:24Gary Vaynerchuk?

  Not necessarily.

• 51:25Lewis Howes?

  Yeah, amazing, man. What is the, uh, the final word you'd like to share with people about?

• 51:30Gary Vaynerchuk?

  Let's, sorry, I got excited.

• 51:32Lewis Howes?

  Go ahead.

• 51:33Gary Vaynerchuk?

  Let's come out of this leaning into humility and gratitude and that will be the springboard to everything you want. If you can, like, just be grateful. Yes, you lost your job or your business is not as good, but your grandfather didn't die from Corona. You know, just be grateful, like grateful for the time you're spending with family now, grateful for the innovation time, the thinking time. I'm sleeping more than ever. Put on a couple of pounds, so I gotta be a little bit more careful, but I'm gaining real muscle. I'm starting to really do it.

• 51:57Lewis Howes?

  Strong man, play some ball soon.

• 51:59Gary Vaynerchuk?

  Uh, but I'm not gonna, I'm gonna dodge you on that. You're too good, but, um. Gratitude and humility.

• 52:06Lewis Howes?

  People can follow you anywhere online.

• 52:08Gary Vaynerchuk?

  I'm findable.

• 52:09Lewis Howes?

  All in, all in challenge if they want to.

• 52:11Gary Vaynerchuk?

  Wine text, wine text. That's the thing I'm most proud of. Here's why.

• 52:16Lewis Howes?

  Wine text.com?

• 52:17Gary Vaynerchuk?

  Mm hmm. Here's why. It's literally the best way to buy wine right now in the world. I genuinely believe that. We sold a $125 Cabernet for $39. We sold a $42 red Meritage for 19 bucks. We have a $40 rosé, premium rosé coming for $9 next month. Like, it's, it's really cool. And here's the other reason for this audience. Seeing how text commerce is coming in the future really matters. But don't sign up if you're not into wine because it costs money to send a text. So I don't, I don't need the pity or the kindness. This is if you buy wine at all, then sign up. And if you don't, don't.

• 52:51Lewis Howes?

  Love it, man. I appreciate you for your heart and everything. Talk to you soon, brother.

• 52:55Gary Vaynerchuk?

  I love you, pal. Thanks for doing this.

• 52:56Lewis Howes?

  Appreciate it, man. Thanks, bro.

• 53:00Lewis Howes?

  I'm so grateful I got to spend some time with my friend Gary Vaynerchuk and get caught up on everything that he's doing in his business, in his life, and also dive in deeper into the mindset of how he thinks during these uncertain times about how he's planning for the future, about when he wants to actually become the owner of the Jets. I'm not sure if he's actually ever said the date and time before. So that was pretty interesting. That and so much more. I just love the way he thinks, the way he calculates his mind, and how he has this unwavering self-belief. The thing that I love about him the most is he is not afraid to put himself out there like so many people in the world. And if you can get an ounce of that for yourself, imagine what you'll be able to create.

• 53:42Lewis Howes?

  Imagine the job you'll be able to go after, the company you'll be able to work with. Imagine the podcast you'll be able to launch, the book you'll be able to write, that video you really want to create. Imagine the possibilities of what you'll be able to do by eliminating some of that self-doubt and going all in on self-belief. That's what I love about Gary and his mindset. And if this is your first time here on the School of Greatness podcast, let me know what you thought over on social media, at Lewis Howes, and tag Gary Vee as well if you enjoyed this with him. Please subscribe over on Spotify. Apple Podcast and leave us a review. And if you are a long time listener, then you know what to do. Think of someone in your life that this could impact today.

• 54:23Lewis Howes?

  Someone you know that could be inspired by Gary's message that needs some more confidence, that needs more inspiration or tools around entrepreneurship and business and send them this link. You can go to LewisHowes.com/955 and send them that link. You can text them, you can WhatsApp, group message, whatever you gotta do. Get this message out there because you never know by paying it forward whose life you can change and transform by sending them this message. You can also just copy and paste the link on Apple or Spotify or wherever you're listening to podcasts and send them that link as well. And I love these quotes at the beginning that I shared. Steve Jobs said, "I'm convinced that about half of what separates successful entrepreneurs from the non-successful ones is pure perseverance."

• 55:08Lewis Howes?

  And Peter Drucker said, "Entrepreneurship is neither a science nor an art. It's a practice." Guys, this is a practice. Becoming a better human being is a practice. Getting in a good relationship and thriving is a practice. Launching a business and doing it over and over at a high level is a practice. Taking care of your health. All these things are practices. You don't have to be perfect, but you do need to practice at it every day if you want to grow. I believe in you. You have so much power inside of you and it's time to start letting it out a little bit more in the world. It's time to start stepping up for yourself just a little bit more every single day. Because when you do that every day and you are consistent in your practice, you will

• 55:54Lewis Howes?

  be so proud of the actions you take and the results will come effortlessly down the line. I love you so very much. I'm so grateful for you and you know what time it is. It's time to go out there and do something great.