Gary Vaynerchuk's Insights on Success, Family & The Future of Business

There's never a bad time to start a great business. The reality is you and I have audiences that will listen to this and watch this that are really great entrepreneurs that are destined to build $500,000 a year businesses.

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. The School of Greatness is proudly sponsored by Amica Insurance. As Amica says, Empathy is our best policy. That's why they'll go above and beyond to tailor your insurance coverage to best fit your needs. Whether you're on the road, at home, or traveling along life's journey, their friendly and knowledgeable representatives will work with you to ensure you have the right coverage in place. Amica will provide you with peace of mind. Go to amica.com and get a quote today.

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Good to see you, man.

You're looking good. 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 proof somewhere, someone has a video clip of me holding three seconds. You know, it was a two and a half count.

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

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 was 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've been donating to Pencil of Promise for years. I see you at the gala all the time. You're giving your time and energy and money. I think it's the thing that a lot of people don't see about you enough is how giving you are and you're especially involved in the all-in challenge right now. I think you guys have raised like $40 or $50 million already. And I know how much time behind the scenes it's taking for you to coordinate, work with Ruben and just put this together and call in favors. There's so much giving you do. So I just wanna say thanks for.

All the- I appreciate that, brother. Look, I think it's really funny, right? Because I'm very much 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. I'm a little bit more quiet about the best version of me, right? And I'm okay with that because I think 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 definitely don't begrudge people promoting their philanthropic kind of ventures either. I think we're all wired differently, but I, that's very nice for you to say. And, of course, and I appreciate it.

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 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? Yes. What it is of those who haven't seen it from every celebrity yet.

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 and culture, music, film, you know, television, sports, 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 in the cleats from his first Tampa game. That's crazy. You know, 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 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-- that's your money, yeah. Yeah, that's the place where I make revenue that allows me to kind of invest in top line growth for Vayner and not worry about profit as much or make investments or try new ventures.

So like- Take risks and try, yeah.

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

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, te with Gary Vee every day. 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. Okay. Before I do, I posted, 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.

Yeah, yeah, yeah.

And some of the 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?

Practical direct to consumer brands, ones that are 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. 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 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 gonna work one to two times a week from home is gonna be, so just like, think about if you're a carpenter, right? 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 are 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 to $50,000 a year person with one or two projects to like a million dollar person, 'cause that is clearly coming. So that's on my mind. 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, I do think, you know, like people are about to be germaphobed out in perpetuity, similar to 9/11, which sucks for me because I'm a very other way, like hug, kiss, like, you know, slobber on someone's face. Slobber on someone's face. Yeah, I'm very like, you know, like don't wipe down anything when I get on a plane. Let's share drinks and eat hot dogs together. No, honestly, eat off people's food. Like, I'm a little bit worried that I'm about to be shunned from society. 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.

That's true, that's true.

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. I, for example, opening a restaurant immediately after this sounds insane, except if you're opening up a great restaurant. Yeah.

You know, it's interesting, I'm in LA near Beverly Hills and I'll drive down this side street with Sprinkles Cupcakes. I don't know if you've heard of Sprinkles. Of course. It's amazing. Well, 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 who had 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.

Listen, my dad a year ago said, hey, you're helping all these companies. What about helping old dad out? And I launched WineText, 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 winetext.com, 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 4, 5, 2, 1, 12, and it's like Brandon hired nine people today for Wine Library because obviously alcohol sales are exploding, but on top of that, this is above and beyond because the innovation is so strong.

What is the direct result from you guys implementing that for this new kind of business? for one library. How is that?

It is. I'll tell you exactly. I don't have the exact bath. I actually have a p&l meeting tomorrow. Roughly, it's going to grow the business by 30 to 40%.

From last year, just one initiative.

One initiative.

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

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

Be- yeah, it's going down 5-10% a year or whatever. And now, boom, let's get back to.

Where it was 10 years ago. 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 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.

It's brilliant. Now, 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 for 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?

Easy. My stuff does better during bad times.

Because they have to.

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.

Right? 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 changed it. Even in Russian, I talk about nine to five making 40,000 a year being happy. But I promise you hard work is about to be put on a pedestal again.

Huge pedestal. I'm always at 20, 30 million people unemployed. Like, people are gonna be grateful just to have an opportunity. 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 be like, Oh, wait a minute, there's some real lasting ramifications. Big time.

Big time.

I can't get a raise, I can't get a job. I mean, I'm just hearing people who.

Are in key positions are getting 20, 30% cuts, even if they are the key player and they're irreplaceable. It's kind of like this.

I said, Gary's like, somebody said to me, Gary, that's not fair. I'm like, let me give me an analogy. 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 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 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. Yeah. People are just so funny with this kind of like ideology, like, okay, or the business goes out of business.

Yeah, we have no money. Yeah. Yeah. 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?

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

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

I really can, man.

Yeah.

I don't know what else to say. Like this has proven it to me even more, you know, any 0.0001% of me that thought, while I've been saying this for Last two years, am I full of sh*t has completely gone away. Yeah. 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, think about whatever, big on. You aren't worried when it comes to sport, you know, your mind just goes into, this is going to be a good situation for me. Yeah.

And for me, it's comfortable.

Yeah. And for me, that's business. Like I know for fact that if I became a 100% full-time garage sale, thrift store, Amazon Flipper, that I make a million dollars a year. I know that for fact. So what the Am I, and that doesn't take into account that I am, that I built a brand. And sure, my brand would take a hit if 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 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, I'm bulletproof. I believe that.

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

Oh, I know Chris.

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

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 going to get the purest execution of it. deapest execution of it. And I get to watch it from coast to coast. And so, and just like that, and just like pure love, right? Like, my daughter got a 53 out of a 50 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 school, like that's her game. And it works for her. And I just sat there and I was like, yeah, you know, like every parent that's listening that right now knows they're blown away by the pride that comes along with a child. 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 going to f*** it 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 going to be proud of them as long as they're happy. I don't need them to be an entrepreneur. I almost don't want my kids to be entrepreneurs because I don't want them to have to live in the shadow or try to climb the mountain I'm creating now.

The pressure.

The pressure of like, moving up to dad.

Yeah.

I mean, you know, we're young. My little guy is turning eight in August. In 10 years, he's 18. You and I hang out with 18-year-olds in business.

How old are you right now?

37. 37. you're gonna be 47, slightly older than I am right now, and you're gonna know Xander for real.

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

Exactly, and then 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 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 built, you know, in our little Russian community, that was a big deal. And I wanted to climb that mountain. And if my kids look at my bigger mountain and say, I'm gonna climb that mountain, I'm gonna cheer them on 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 get the relationship graph, which already gives them a huge upload because Uncle Louis is gonna give 'em a hundred thousand for their, you know, I said, 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 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.

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

If that makes them as happy as it makes me. yeah.

And I want to expect it from them, though.

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. There's a certain version of us that are artists that genuinely like this. more than anything. A force inside and out, the Range.

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Like, like we like singing, like Beyonce is a workaholic. Yeah. You know, like Kobe was a workaholic.

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

So for me, like, like we demonize it in entrepreneurship and corporate life, but we don't in art. 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 gonna burn out. He's gonna suicidal.

Why is that? Is that just because of the old way of thinking, like getting burned out.

In the corporate world of doing a job you hate? Yeah, money, money. You know, I don't think people like Mark Texiera made 213 million dollars 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 business woman much, much more than the Entertainer that makes way more money.

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.

Yeah.

Even now, it's not like you said it for a few years. You say it every day or week or because it's true. 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?

Very good. I do think my parents for me, and they parented all three kids a little bit differently, but like, but they're like, we 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.

No breaks.

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 them. But I do think the thing that we have more is balance 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 to have 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. 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 look at that.

That'S cool.

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, you know, just genuinely, like, just willed his way into success. And I think I have a lot of that as well.

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

Yep.

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 response 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?

You know, I think, you know, back to extremism, right? Like the extreme which I use, I, you know, all of it can be better and all of it is just great. 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. Like 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 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, 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? Like, you know, like, 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, 'cause 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 going to mean those, you know, now all of a sudden it's Tuesday and Wednesday, you know, like technology, like FaceTime culture. I've exploded my FaceTime international interaction with them.

And so, like, those kind of things.

Yeah.

How does Gary eliminate self-doubt and self-sabotage when it seems like there's so many wins that you hit, but also people don't see all the big losses that you have as well in the risks and the. 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. And I think what you know is forget about like 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 going to 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. But I'm never doing anything for any other reason that 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 s*** that people are thinking about, you become vulnerable. I mean, so many people are overexposed. I mean, listen, there's some big personalities that are going to get smoked out over the next 12 months that have played the part on Instagram. They're going to lose.

They just are. I also think if you're focused on chasing the money game of competing against someone financially, 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. Everything becomes an attack. So if you lost a, if you, let's hypothetically say you lost a million dollar bet on a business or an.

Investment or whatever, and I've got, I've got one that's going to happen soon.

So go ahead.

And it went to zero.

It's going to. How do you tell yourself, I still love myself. This doesn't, you know, affect myself.

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 going to offset that million loss. It's an L. I don't want it, but it's real.

Wow. 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.

I go into everything thinking it's going to be zero.

Really?

Yeah. It really makes it. Why do you think notice. Does that make sense now all of a sudden I go in with no hope.

No expectation. No expectation.

I don't do it for my kicks and the giggles. I think it's gonna work. 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 Pure Wild 137. Harwood does. I don't run Vayner Sports. AJ does. I don't run Vayner speakers. Zach Nadler does. I'm impacting the living out of those people.

You're influencing them. Yeah.

Oh, in a real way. Yeah. But You know, push comes to shove, I don't make those decisions. And so and I support my partners in crime. And so that's kind of how it is.

Yeah. Over the last, I think you start when did you start VaynerMedia? Was it 2010? 2011 2009. So I was in the office, I think it was Soho when there was like six people in there and a ping.

Yeah, Sunshine, Sunshine Suites.

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

That's right.

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.

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.

What do you mean by entitlement?

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

Within the company?

Yep.

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

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 a soft. Which is wild.

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

I was impacting so much that 300, 400, 500 people had it too easy and we had to do like a 35 person layoff because I just kind of 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 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.

They weren't great at their job. They weren't even close.

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

And everyone loving you.

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. AJ leaving was tough. I was gonna say that was.

That's what I thought you'd say there. Yeah, that was a big blow.

I didn't see it coming.

You guys built this together. This was 50 50. This was. Yep. We're gonna grow this as a Empire with a family.

Yep. Yep. And, like, being with my bro and all that.

And.

And so that was rough. He left for anybody who 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. client service business suck. And he just said, I'm 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, 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 going to 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've both genuinely love each other more than money. But it's still, you know, you have 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 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. 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. Oh, man. 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 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 going to let us get through this in a good way when it's all said and done. But we could have gotten, like honestly, I sit here and say, my God, if Marriott, Hilton, if American Airlines, if I'm trying to think of other people, clothing, if Neiman Marcus, you know, retail, like if our product, if our client mix was different, this would have been maybe it. Really? 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 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, Mm-. Chuck E. Cheese, I'm trying to think of a million different things and sports.

What about that?

The Jets, the NBA, all these, the serendipity that's like we just got the perfect wrong hand, 3-7 off suit. I would have been super, I'd be doing this video and be like, that's what happened. And I couldn't see it coming and I deserved to lose.

Like literally that would be like my reaction to it. Yeah, and you'd almost be excited to start from. Oh, you always talk about, I wish something happened so I could build it back up again. How much has your business been affected? Have you lost, you know, half your clients?

We've lost 10% or maybe we're definitely 12% down in like top-line revenue expectations. We've had, we have, 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 What are you doing? And I'm paying my employees.

Yeah. And I'm paying rent. Exactly. That's tricky, man. You got to get a Higgins to.

Give you a little break on that rental. Yeah. The problem is, even Ross, like he has partners and banks and it's crazy. 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 plus 50 to $300 million businesses are.

The ones that are going to go out of business. what are you doing personally to supplement the speaking fees?

Nothing.

Nothing. Are you innovating anything to launch or create or.

No, I'm massively tripling down on, you know, empathy is doing really well. So, yeah, empathy wines are doing well. So my wine business and my, my dad gets all the income for the family business. So that's, I'm doing wine texts 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 why savings matter.

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.

Yeah, but a lot of, you know, most of my, most of my net worth is tied up in non-liquid investments, right? It's true. 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, you know this, like, I've been yelling for a year and a half about sports cards.

They've gone through the roof. I know. I feel that I didn't get any MJ cards after this. You told me a year ago, you're like, get LeBron, give Jordan, get all this. And now it's going up because of this stuff.

I'm curious. Jordan rookie cards went from 20 to 100, 000. It's crazy, man. Like, everyone's, like, getting into startups. I was like, I put my, you know, like, LeBron rookies I bought for.

1100 or 7, 000. Oh, man. And when you buy 55 of them, that's money. Oh, that's money. I'm curious, we talked about how you overcome self doubt. How would you inspire other people's or educate them on how to eliminate self doubt in their life?

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

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

I think it's humanly, like, this is what I think, like, 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. 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.

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.

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Services member NYSC SIPC. Wow, the liberation to then actually do sh*t. And now you're doing sh*t full throttle because 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, 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. That's powerful.

Yeah, I think, you know, even I've.

Never said it that way. Like, I even like, thank you. I was like, literally when you, I got to 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 here long for a ride. Like over the last two or three years, I can feel I know, 'cause I'm a branding guy.

Like the brand is in a different place.

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

Yeah, you have.

And I'm like, okay, well, I'm 44.

And I'm like, you know what I mean? I love the stories of like Colonel Sanders at 50 launching KFC. It's like, they take off at 50.

It's like, you're just getting started.

Yeah, I think Sydney Frank started Grey.

Goose in his 80s.

You haven't even got started yet.

I really believe that. It's the preseason. 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 I, somebody said, Gary V, you did a really, really good job. You know, you were super early on podcast, you know, saying all this stuff. 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 to charm, right? And Pat Flynn and others, Dumas, right? Like others, I'm like, they were a little earlier, Ferris, like they were earlier. I'm like, I did, I've done a fine job. 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, you know, and obviously I made the 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, 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.

It was big guy Kawasaki and Twitter.

Right, right. And both of them are still doing their thing. Everybody does different things though, right? Like some people come 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 09 10 11 when I was popping for the first time, I'm such a loudmouth. 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 going to be kind of like this phoenix of like and then disappear because it just didn't seem quote unquote. Yeah. And I remember thinking, man, I remember then thinking, wait till they see in 10 years where I sit. And it's happened. And I think and I think, man, wait till people see where I'm gonna be in 10 years from today. You're just getting started.

I feel like, okay, I spent the last 10 years of foundation work. Researching, like trying stuff, making mistakes, something's working well, like figuring out, reinventing, really trying to find my true lane. And okay, now I can get started. Yeah. You know, it's like, all right, now let's do something cool. And let's build off of what we've got with the personal brand and leverage it.

Look what I did in 11. 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 they're gone now. Right.

That's too big about valuation and now stock. And now I have a marketing foundation.

That'S a f*cking supernova. You can launch anything. Anything.

You've got the engine to launch a product. Empathy Wines is a meaningfully successful direct to consumer wine brand that John and Nate run.

It's crazy.

Intern. Software and a couple of interns. Yeah, but they were interns. Now they're 10 years under my watch. Now they're executives.

Wow, Ballin. What is the, you mentioned earlier, client work is sh*t. And agency work.

It is.

Why put your life's attention into sh*t business model, essentially?

Because I'm building the Death Star. I'm sure the Death Star was sh*t 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 in the prime of my career, except here I am at 44, empathy being the first one, the rest of my life are going to 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, you know, a Tracer Vayner.Tech, you should, people should check out. It's a data analytics SaaS business. It's got, you know, the Sasha Group for small businesses.

I'm building literal machine.

Machine. That's the scalable version of who I.

Am as a human.

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

If you could predict, what was your prediction 10 years ago when you launched VaynerMedia? Was it to be where you're at with whatever, 6, 7, 800 employees and.

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

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

It's why I did the K Swiss thing, right? It gave me a chance to test it when I realized I wasn't going to be doing that just yet. And it came in front of me and I did it and it really worked and they sold that car. Look at Resi. Resi had a hefty exit, right? Resi is my biggest exit. I never talk about it. I co-founded it.

Wasn't that a 200 million or what was it?

Yes. Plus. So like, I'm winning out here. Resi is kind of like the, like.

I remember Resi 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.

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, why not talk about that though? Why not talk about the thing that.

You launched and it was a big hit? 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. 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. They executed day and night. 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 played my DNA in Resi.

But that has been most, first and foremost, that's Ben's win. 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 are you going to see happen by then?

I thought I was going to build like a, I thought I was going to build the Millennial Falcon and buy, you know, K Swiss. What ended up happening is building the Death Star. And so when I buy Puma 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 give me the the year and the date and the time that you're gonna sign okay okay for the Jets what is the exact time 2020 date.

November 11th 9 A.M. November 11th 20. what do we mean 20 2048. 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 not necessarily Just amazing, man.

What is the final word you'd like to share with people about?

Let's, sorry, I got excited.

Go ahead, go ahead.

Let's come out of this leaning into humility and gratitude, and that will be the springboard to everything you want. If you can, just be grateful. Yes, you lost your job or your business is not as good, but your grandfather didn't die from corona. Just be grateful. Grateful for the time you're spending with family now, grateful for the innovation time, the thinking time. I'm sleeping more than ever. I put on a couple pounds, so I gotta be a little bit more careful, but I'm gaining real muscle. I'm starting to really do it. Strong man, let's play some ball soon. But I'm not gonna dodge you on that. You're too good.

But gratitude and humility. People can follow you anywhere online. They can get all in challenge if.

They want to support you. Wine text. Wine text. That's the thing I'm most proud of.

Here's why.

Winetext.com. 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 day for $39. We sold a $42 red Meritage for 19 bucks. We have a $40 Rosé, premium Rosé coming for $9 next month. 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 need the pity. or the kindness. This is if you buy wine at all, then sign up. And if you don't, don't.

I hope today's episode inspired you on your journey towards greatness. Make sure to check out the show notes in the description for a rundown of today's show with all the important links. And if you want weekly exclusive bonus episodes with me as well as ad free listening experience, make sure to subscribe to our Greatness Plus channel on Apple Podcasts. If you enjoyed this, please share it with a friend over on social media or text a friend. Leave us a review over on Apple podcast and let me know what you learned over on our social media channels at Lewis Howes. I really love hearing the feedback from you and it helps us continue to make the show better. And if you want more inspiration from our world class guests and content to learn how to improve the quality of your life, then make sure to sign up for the greatness newsletter and get it delivered right to your inbox over at greatness.com. com slash newsletter. And if no one has told you today, I want to remind you that you are loved, you are worthy, and you matter. And now it's time to go out there and do something great. Comcast is committed to bringing access to the internet to all Americans, including rural communities across the country, like Sussex County, Delaware.

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