New book from NYT bestselling author Lewis Howes is now available!

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Gary Vaynerchuk

Insecurity, Fame, and Crushing It in Business

“No entrepreneur can be successful with someone who isn’t independent.”

As you know, it’s important to continually grow (especially if you’re an entrepreneur). I’m not excluded from that. Ten years ago I read a book by Gary Vaynerchuk that changed the course of my life.

On this episode of the School of Greatness, Gary returns to the show for his third time. He gives me advice for my next ten years but also gives you invaluable advice on so many topics that you won’t hear anywhere else.

Gary is known for his unapologetic truth-telling attitude. He says a lot of things on social media that people may feel are harsh or extreme. But when we were talking, Gary revealed he actually cares deeply about what people think about him. And that’s why he’s so committed to serving people with hard-earned business wisdom in the long run.

He explains why teenage nerds are winning right now, how hitting the big lists isn’t what matters in business, and why you need an independent person in a romantic relationship.

"Impact more people, that’s the bigger KPI.”  

If you aren’t familiar with Gary, you’re missing out. Gary is a serial entrepreneur and the CEO and co-founder of VaynerMedia, a full-service digital agency servicing Fortune 500 clients.

Gary rose to prominence in the late 90’s after establishing one of the first e-commerce wine sites, WineLibrary, helping his father grow the family business from 4 to 60MM in sales.

Gary is also one of the most sought-after public speakers alive today. He is a venture capitalist, 4-time New York Times bestselling author, and an early investor in companies such as Twitter, Tumblr, Venmo, and Uber.

You’ll learn everything you need to know about how to become the best of the best, on Episode 595.

"The greatest way to be selfless is to be selfish.”  

Some Questions I Ask:

  • How are you affected emotionally when you see yourself aging? (9:32)
  • Did business get better for you when you got married and started having kids? (16:52)
  • When you started having kids did your obsession for business stay the same? (22:31)
  • Why are you doing things you don’t like when you have options not to? (24:51)
  • When are the moments that you doubt yourself the most? (26:09)
  • What’s your insecurity? (33:45)
  • What do you think you need to take you to the next level? (38:00)
  • What advice would you have for me over the next 10 years? (51:52)

In this episode, you will learn:

  • The results you should be concentrating on in business (14:02)
  • The biggest challenge Gary’s faced since starting Vayner (23:13)
  • Best way to actually build your Instagram following (30:21)
  • Why Gary hates being disliked (34:20)
  • When relationships are really made (42:41)
  • Plus much more…

Connect with
Gary Vaynerchuk

Transcript of this Episode

Lewis Howes:              This is episode 595 with New York Times best selling author, Gary Vaynerchuk.

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.

Ralph Waldo Emerson said, “To be yourself in a world that is constantly trying to make you into something else, is the greatest accomplishment.”

Welcome to this special episode, an interview with none other than Gary Vaynerchuk, and if you don’t know who he is, you’re probably not on social media because he is everywhere. He’s a serial entrepreneur and the CEO and co-founder of VaynerMedia, a full service digital agency servicing Fortune 500 clients across the company’s four locations. He appears with Gwyneth Paltrow, Jessica Alba and Will-I-Am on Apple’s first original series, Planet of the Apps.

He’s also one of the most sought after public speakers alive, today. He’s a venture capitalist and four times New York Times best selling author, and an early investor in companies such as Twitter, Tumbler, Vimeo and Uber. Gary is currently the subject of DailyVee which is an online documentary series highlighting what it’s like to be a CEO and a public figure in today’s digital world.

He’s also the host of #AskGaryVee, which is a business and advice Q&A show online. And he’s got a brand new book out that is literally crushing it, and it is called, Crushing It: How Great Entrepreneurs Build Business and Influence, and How You Can Too. It is out right now, and I’m actually one of the featured subjects in the book. So, make sure to go get a few copies of the book right now, while you’re listening to this and you’ll see a full section about me, meeting Gary a few years ago and reading his other book, Crush It, and the lessons that I learned and applied from that to how it impacted my business over the last decade. So, definitely check that out, get the book, Crushing It.

And, what we cover in this one: now Gary talks about a lot of different content. He’s always out there speaking on stages, he’s got tons of content maybe you can listen to. So, as you know, I always try to get people to share things that they never share anywhere else. And I think we were able to do that today. It’s hard to do that with Gary, because he talks a lot about everything, but I try to ask the questions that no-one’s willing to ask.

And some of the things we cover are why the teenage nerds are winning right now, in Gary’s opinion. Also, why hitting the big lists and getting verified is not what is important online and in business. Also, why having an independent romantic partner is essential for an entrepreneur, and Gary’s take on his romantic relationship and business. And what Gary is actually terrified of the most in his life. And the advice Gary gave me about the next ten years of what I should be doing in my business, kind of taking it full circle from ten years ago, reading his first book, to know, what he thinks I should be doing for the next ten years.

I am very excited abou this. Again, make sure to screenshot this, tag me and @garyvee on Instagram, and the link is, if you want to share the link out and watch the full video interview and all the stuff we talk about at the show notes.

Before we dive in, I want to give a shout out to the Fan of the Week. And this is over on iTunes. We get reviews every single day. If you haven’t left a review yet, make sure to leave one now for your chance to be shouted out as Fan of the Week. This is from Mike25 who says, “Anybody not listening to this podacast is crazy. The podcast is easy to listen to and keeps your interest. The interviews Lewis has with special guests is both spiritual, informational and especially motivating. Please consider this podcast, you will not be disappointed. Great job, Lewis!”

So, thank you, Mike25, you are the Fan of the Week. And, again, head over to iTunes or just on your podcast app, right now, on your phone, you can go on there and leave a review for your chance to be shouted out as well.

And this episode is brought to you by, Bench. Bench is the online bookkeeping service for your business. Bench gives you a team of bookkeepers, guys, to do your books, and simple, elegant software to track your financials. I cannot stress this enough, if you are an entrepreneur or a freelancer, you must have your books in order, and every month, your Bench bookkeeping team turns your data into tax-ready financial statements. You can either monitor your business’ financial health, download your financial statements and chat with your bookkeeping team at any time via the Bench App.

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So, try them out for free right now, you get a free trial when you sign up, you get full access to Bench and they’ll do a month of your bookkeeping and provide you with a set of financial statements for free. That’s right, guys, and as a School of Greatness listener, you’re also going to get 20% off for your first six months of bookkeeping. So, go to right now, they’ll do the first month for free and then you’ll get 20% off your next six months of bookkeeping. Again, check it out,

And this episode is also brought to you by ZipRecruiter. If one of your goals this year is to grow your business, you can’t do it on your own. Gary took his agency from just a few people to almost a thousand employees, now. He needed the right people on his team to help grow his business. So, do you know where to post your job, to find the best candidates for your business?

Well, with ZipRecruiter you can post your job to 100+ job sites, with just one click, guys. Then, their powerful technology efficiently matches the right people to your job, better than anyone else. That’s why ZipRecruiter is different. Unlike other job sites, it doesn’t depend on candidates finding you, it finds them for your. And, in fact, 80% of employers who post a job on ZipRecruiter, get a quality candidate through the site within one day.

You don’t have to go through a ton of different e-mails, you simply screen, rate and manage candidates all in one place, with ZipRecruiter’s easy-to-use dashboard. Find out today why ZipRecruiter has been used by businesses of all sizes to find the most qualified job candidates with immediate results. And right now, as a listener of The School of Greatness, you can post jobs on ZipRecruiter for free. That’s right! You get to do it for free!

Just go to, again, to start posting jobs for free today.

Alright, guys, get ready for this one, this is the big one, Gary Vaynerchuk, the one and only, and I hope you enjoy the episode!

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

Gary Vaynerchuk:         Hey, brother!

Lewis Howes:               Good to see you, man, as always.

Gary Vaynerchuk:         Good to see you! Fun to be back.

Lewis Howes:               This is the third time you’ll be on the show.

Gary Vaynerchuk:         Second time here, first time it was in my bedroom, I remember, because, I just remember it, I don’t know why.

Lewis Howes:               Yeah, I think I’ve interviewed you probably a bunch of times, one time you were in an airport lobby for one of your books.

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

Lewis Howes:               You shared out the video, yeah, yeah, from Crush It.

Gary Vaynerchuk:         Your review of Crush It, ten years ago. Dude, you haven’t aged, which is weird. I don’t know if anybody who’s listening to this show right now thinks this is weird the way I do, which is that Lewis is always good looking, and all that, but forget about good looking or fit, he’s got all those things down, I just mean, actually ageing.

Lewis Howes:               That’s good. I’ve been told I have good skin. I don’t know what that means, but…

Gary Vaynerchuk:         But you also agree with me, that you haven’t aged that much yet in these eight years. How old are you?

Lewis Howes:               Thirty-four.

Gary Vaynerchuk:         Okay, good. That makes sense, because I didn’t age too much from twenty-six to thirty-four either.

Lewis Howes:               And then you started to hit the wall.

Gary Vaynerchuk:         Then I fell apart!

Lewis Howes:               Well, that’s when you started to invest in yourself and you realised the importance of health.

Gary Vaynerchuk:         Oh, yes, yes. But, I mean, besides losing fat and starting to get a semblance of muscle, but grey hair and losing my hair, and just a wrinkle, like, actual ageing.

Lewis Howes:               How does that affect you emotionally when you see the ageing of the hair, or the skin, or the wrinkles?

Gary Vaynerchuk:         Not much, actually. You know, it’s weird, I’m pretty vain and all that stuff, I’m into that. It should affect me more. Here’s the punch line, it’s, like, what are you going to do about it? Like, I guess I can debate hair implants, which once in a weird mood, when I see an angle from a Babin video or DRock, and I’m like, “Oh, my hair’s going!” I’ve got 18-36 months before I have to shave my head, it’s just going enough back here.

But then I’m always like, “Or, should I get an afro?” Should I just get a huge implant situation like Matthew McConaughey or whatever, I’m sure he did something. Or like Jeremy Piven, I mean, you look at the old guys, or Elon Musk, you look at some of that content and you’re like, “Mm-mm. Elon, you didn’t just magically grow hair,” so if anybody’s listening who does that really well, I could be sold, looking at Nick’s hair, I could rock some long-ass hair, one last rodeo before I’m finished.

Lewis Howes:               Does any of that affect you, though, in terms of your confidence in business?

Gary Vaynerchuk:         No, no. Not in business. You know, that’s what’s so great about business. I’m not an Instagram model, I’m not an actor, I’m not looked at or liked, or my return on investment has nothing to do with my physical appearance, so, what’s great about being a business person, it’s a mind game, and an execution game. I also think that’s why a lot of entrepreneurs and business people don’t maybe take care of themselves as much as they should in things of that nature.

No, I think it’s more of just being a guy or being somebody that’s transitioning into their early forties and you kind of know what the next chapters look like, I think you think about it much more from, “Oh, I’m getting older, like, mortality,” I don’t feel less confident because of my physical [appearance], because I also, unlike you, who’s a physical specimen, there was never a time in my life that I ever looked as my looks or physical status as a self-esteem builder.

Lewis Howes:               You look at the results in your business.

Gary Vaynerchuk:         Yeah. To me, I was cool, even though nobody else thought I was cool, because I made four thousand dollars selling 8000 Ken Griffey Jr. Rookie cards this weekend in the Phillipsburg Mall. And so, for me, it’s interesting, I had so much self esteem around business results when that was not a “thing”, now that’s a “thing”.

It’s really interesting to get these DM’s. I love the fifteen-year-old guys that slide into my DM and tell me stories of why they look up to me, because it really is actually very funny, the entrepreneur’s cool now. When you’re fifteen you want a girlfriend. You want to be popular, and I look at their photo’s and these are not fifteen-year-old Lewises, these are some nerdy-ass kids, but they’ve got ridiculously cool girlfriends, and I’m like, “Oh, this entrepreneur thing has really hit high school!

This is real now! Wow!” If you’re a cryptocurrency millionaire, as a kid. It’s really fun for me that the thing I love the most, entrepreneurship, has become cool. I know that somebody listening to me who’s over forty, and loves entrepreneurship the way I do, they also know what I’m saying and that anybody under thirty has any idea of how I’m actually describing it, and then there’s that middle, thirty to forty, which is in between. But if you’re over forty you know that when you were in high school, being a businessman or woman, had zero street cred. Zero! Zero point zero, zero.

And for the kids that are listening, I know there’s a lot, like being an awesome violinist right now, that’s not going to necessarily crush it in the halls of, like, Draymond High. That was equally the same thing that I was going through, which was, nobody gave a f**k that I was making $10,000 at a flea market in a weekend. That meant zero status, like having a Starter jacket.

Lewis Howes:               Or the music you were listening to, or the jeans you were wearing, yeah.

Gary Vaynerchuk:         Correct, or like scoring thirteen for the team that night, or being in a band, like, you know, the cliché move, all the guys did. Or being good at skateboarding. There was nine thousand other things, and it’s crazy to think, because money has always been the cliché thing that has helped some people close the gap of coolness.

Lewis Howes:               Yeah, but not in high school.

Gary Vaynerchuk:         But not in high school, and definitely not in 1990 to 1994.

Lewis Howes:               Now if you have 50,000 followers on Instagram in high school, you’re the hottest thing.

Gary Vaynerchuk:         Or, talk about society wrapped up in vanity, like, social. If you are a high school guy who’s a nerd, but you get a blue check from Instagram, your life changed.

Lewis Howes:               Changed! You could get any girl you want.

Gary Vaynerchuk:         The amount of people that send me things, like, “I will rip my arm off, if you could help me get verified on Instagram.” It’s like, literally, things like, “I will sell you my children, if you get me verified on…” ; “Give you my home, and live in a cardboard box.” And I’m just, like, “This is the saddest s**t ever. A lot of my content in the last six months has been, like, “Please do not get wrapped up in likes and your rank in the podcast list or checks.” That is such a death game, you will lose that game. You will start pandering to those results, versus actual results.

Lewis Howes:               Like creating a great product consistently.

Gary Vaynerchuk:         New York Times best seller list. I don’t pander to that. I don’t want to hire the companies that get me on a list, I want to sell more books. That’s the KPI. Impact more people, that’s even the bigger KPI, but look, I mean, the world has always traded on… Do you know how sad at this point I am when I’m on these thirty, I mean, well, I’m not thirty, like, Top 40 Influencers or 50, under 50 now, which is the only thing I can…

Lewis Howes:               How old are you now?

Gary Vaynerchuk:         Forty-two. So, I hate it, because my feed gets filled up with, like, “Congratulations,” or the other people that are on it, trying to get me into a conversation, not because, kudos to them, because I was the most pumped too, when I was like, Ten Most Important People in the Wine Business Under Forty. Amazing! I get it! As you get older, you realise how those awards, or those completely arbitrary things of and editor liked one of your podcasts and decided… And we all get excited. Six Best Podcasts to Listen To in 2018, you want to be a part of that, you want awareness.

Here’s what I would say: We’ve over corrected a lot of people into caring about that more than the actual results and so we care more about the facade, and we care more about, like, “Look how nice my room…” We’re in a beautiful room right now, right? You’ve really done a nice job with this, I like how you put the more important people on their own wall over here.

Lewis Howes:               Well, they were just bigger photo’s, so we had to place it…

Gary Vaynerchuk:         No, no, no, you made them bigger. I know you! But here’s what’s interesting to me: What’s interesting is, if the concrete and steel under this building is s**t, well, this whole thing falls and it doesn’t matter that you put some tree…

Lewis Howes:               How pretty it is, yeah.

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

Lewis Howes:               When you were in high school and college, and in your twenties, and you were dating. I don’t think you ever meant to talk about this, it just came up for me now. Were you driven by dating a lot of girls or were you trying to impress them through the business you were building in the wine space, and did business get better for you when you got married and started having kids, or did it hurt you? You know, did it help, or…?

Gary Vaynerchuk:         That’s a very good question. I was so one-track-minded in my twenties, from fifteen to twenty-five, fifteen to twenty-seven, in twelve prime years where a boy, then a young man cares about dating and hooking up and having a girlfriend, the level of me giving a f**k about that was stunningly low.

Lewis Howes:               Really? Did you have a bunch of girlfriends, or no?

Gary Vaynerchuk:         In high school, not at all. In college I had girlfriends, but from my junior year of college until I got married, I pretty much always had a girlfriend except when we would break up and I would have a couple of months in between, but it was literally like, because I almost weirdly thought I had to.

Because, look, I mean, you like to have a companion, fine, but my business was more important than my girlfriend by a magnitude of a thousand to one in those four relationships I had, five relationships I had in between my first serious girlfriend in college and marrying my wife. My wife is such an enabler of my entrepreneurship.

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

Gary Vaynerchuk:         She came in eyes wide open and is so independent and wants to run the household and the kids the way she wants to, she wants to be the dictator and CEO of our home life, that she likes that we’re in a divide and conquer dynamic. Lizzie’s aspiration is not to co-parent. She doesn’t want my two cents. She’ll take it once in a while, but she wants me supporting her, on her vision and execution, and I have empathy for that, because that’s what I want on what I do for a living. And so, we’re a good pair.

I think if you have somebody, no entrepreneur can be successful with somebody who is not independent. None. There’s no entrepreneur, no, Sally, if her husband, Rick, is not independent and can’t keep himself busy and isn’t about his life, she can’t do what she needs to do, because he’s going to be pulling her at all times and making her feel guilty for taking that extra business trip, for looking at the phone during dinner, and so you need, if you’re a true-bred entrepreneur, an obsessed entrepreneur, and what I mean by that is, I believe I know your own answer, I know mine, I believe 87% of people listening right now are in it for the money. They’re in it for the short-term, get the money, go on a nice vacation, right? Buy the nice car. If you’re part of the 13% that I’m a part of, which is you would die tomorrow if somebody said you couldn’t play.

I would much rather make $100,000 a year, and I proved this, this is what it did. From twenty-two to thirty-four, I made 150, 130, 67, $49,000 a year, building my dad’s business for him. I never got upset that I had no equity. I don’t have resentment that I left that business at thirty-four with nothing. Even when people say to me, don’t listen to Gary, his daddy put him on, gave him the business, when I know the true story is, I didn’t get anything. I just built a monster business for my dad in my best years of my youth and then left and started over. I mean, VaynerMedia started with me getting a client to pay, because I had no money, to pay me and AJ or anybody else. I had no money.

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

Gary Vaynerchuk:         And you crushed me in ping-pong. Lewis is awfully good at sports. It makes me upset.

Lewis Howes:               Yeah. Well, when you’re a lonely kid your whole life and you have all day just to hit a ball against a wall.

Gary Vaynerchuk:         And you’re shaped like an Adonis, yeah. That part too. Anyway, nonetheless, for the 13% who are listening, they get it, which is, look, no question, I think a lot of people are like, “Bulls**t,” if they don’t know me, but you know me, make $14,000,000 a year, right? And not be able to play any more? Passive income. Make $200,000 a year, and be able to play? Not even close! It’s $200,000 and play. I’ll suffocate, I’ll suffocate, I’m like a fish out of water if I’m not building a business.

Every moment of my life since 1987, has been unbelievably, passionately, 98% of my human energy against the notion of either my family or building the business that’s in my hands at the time: baseball cards, liquor store, my personal brand, VaynerMedia, the investments I’ve made, selling a book, I’m always in project mode, operating. From the day I started working, I’ve been running a company. Becoming GaryVee and all that stuff, there’s never been a day where GaryVee has been my business. Every day, since May of 1998, I’ve been running Wine Library or VaynerMedia, all of them, every single day, in continuum.

So, yeah, I mean, to me, if you’re that, if you’re one of those 13%, for all the 13% that are listening, if you’re not married, or, by the way, if you’re married, you may want to consider divorce. I’m being really serious here. Because you’re not doing yourself a favour and you’re not doing your partner a favour. If you’re not blindly supported, you will suffocate and die. It will not work. It just will not work.

It’s the same reason I give kids advice to tell them to go tell their parents to go f**k themselves when they want to tell them what to do in their twenties. Not because I’m rogue or I’m trying to be popular or create a viral piece of content. It’s because, when they’re forty-seven, they’re going to hate their parents, and so if you’re doing what your parents want you to do, because you love them, you’re just appeasing the short term, because you’re going to end up having no relationship.

Lewis Howes:               Yeah. When you started having kids, did the obsession for business stay the same?

Gary Vaynerchuk:         No, no.

Lewis Howes:               Or did it increase?

Gary Vaynerchuk:         Probably.

Lewis Howes:               Or did it go down?

Gary Vaynerchuk:         It definitely didn’t go down.

Lewis Howes:               Yeah. So the obsession has stayed the same since you were, whatever, twelve, thirteen, fifteen, to getting married, to having kids, it stayed the same? Or has it gotten stronger?

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

Lewis Howes:               Yeah, yeah. What’s been the biggest challenge for you since starting Vayner and the transition out of Wine Library, what’s been the biggest thing you’ve had to overcome?

Gary Vaynerchuk:         It’s been pretty damn good. I think VaynerMedia and VaynerX, the holding company that holds PureWow and VaynerMedia and the other things I’m about to do, has been a pretty good run. I think that one thing that sucks is having clients. When I ran my dad’s business, I was the boss. People were trying to sell wine to me to sell to other people, thus I had the leverage in the B2B environment.

VaynerMedia, I’m the reverse. Chase is my client, Buddweiser is my client, I’m on their time and I’m fancy now. I shouldn’t be in a place in my career at forty-two, with my nett worth and all this stuff, where I’m at, where I’m at the beck and call, and have to be late for something that I don’t want to be late for, because a client’s yelling at me and not being mad about something, but I chose the profession, and I have the humility, in the prime of my career, to be in it.

So, the biggest challenge is, I’m over myself and I have the humility to run a client service business, I’d be lying if I didn’t say when I’m dealing with something like that, I’m not, like, “What the f**k,” you know, I’m like, making fun of myself to myself. When I have the anxiety when I have to call a client, tomorrow for them to yell at me and say I suck, when they’re an idiot, and I’m going to be the greatest of all time. That’s a little weird.

But you have that conversation with yourself, of like, “What am I doing here?” When I can make more money just being GaryVee, than I can running VaynerX and I’m dealing with seven meetings in a row where people are complaining about other people within the building and I’m playing guidance counsellor? I like that, because I want to make people’s lives better within my company, but there are days, and I eat s**t for a living, but there are days when I’m like, “Why am I doing this? When I have a million options not to?” So, then you start asking yourself.

Lewis Howes:               So why are you doing it?

Gary Vaynerchuk:         Because I think I’m holding my breath for the bigger win. I think that I’m going to build the greatest communications holding company of all time, then buy brands and I think I’m going to run them through this machine, this death star, and I think I’m going to buy Vans for $874 million one day, when it’s on the down side, because right now it’s not, it’s in the prime side, but again, when it’s not, when it’s on the down side in seven years, when none of the kids care, or people care, I’m going to buy it and I’m going to flip it for four billion and it’s going to be because I ate s**t for twenty years.

My plan is to build a platform that is there for me to help Pencils of Promise, something we’re both passionate about, help Crohne’s Disease with AJ, help what takes my parents’ lives. If you decide to run for governor of California, in thirty years, help that. Whatever I’m passionate about, and also sell sneakers and hats and hoodies and books and I needed to build this machine for myself, for the rest of my life, and so I’m willing to eat s**t right now to build it, because it will make the fifty next years really exciting.

Lewis Howes:               When are the moments that you doubt yourself the most? Because I know you’re extremely confident in yourself, but, are there moments, what are they and how do you get through it when you have that doubt in anything you’re doing?

Gary Vaynerchuk:         One of the weird things I do, is, I’m in a funny place now, where I’m not putting myself in a place where I doubt myself, and so I always wonder, is that not challenging myself, or is that staying in my lane? But I will tell you, when you ask me, what’s scary: Reading in public is scary, because I can’t read. Even the last time we did the AskGaryVee book, for the audio book.

Lewis Howes:               You just kind of rift through it.

Gary Vaynerchuk:         You know what’s funny, I always do that, because I get bored, because I, that’s why I got F’s. Because I don’t want to read my own book, I know what’s in here. That’s why people buy the book and the audio book because they’re basically not even the same. It was fun, actually, for me, because I was like, “Oh, I’m a better reader, I think I’ve been forced to read so much over the last ten years, since we became a computer based, e-mail based, tax based world, but if you were like, “Okay, read my notes here right now, to the podcast,” I’d be like, you could literally ask me to get naked, I’d be, like, “Alright, well…” but if you said, “Read this, verbatim,” I’d be like, “Uhhh…” because I don’t like that.  But then it’s things like, throw me in a pit of snakes, I’m like, “I don’t want that,” like, “Jump off this building,” like, “F**k that.”

Lewis Howes:               But there’s nothing in business that makes you doubt yourself. And is there a situation that you could see, like you’ve spoken in front of 50,000 people that’s not scary.

Gary Vaynerchuk:         Nothing in business, no. At this point in my career I’ve been in the room with everybody, and that means I have not been in the room with a ton of people, but every step…

Lewis Howes:               All the big leaders, every billionaire, every CEO.

Gary Vaynerchuk:         That’s right, that’s right. I’m of the cloth.

Lewis Howes:               You’re confident too, yeah.

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

Lewis Howes:               In that game, yeah.

Gary Vaynerchuk:         In the game that I like, which is: Winning personally and winning helping other people, I don’t think I’m going to be touched. I think I will be the guy. I think they will go back and be like, “Look, here are the people who were entrepreneurs during the time when entrepreneurship was cool, and here are all the different things, Elon invented the craziest s**t, and Mark Zuckerberg and Bezos created the best companies and made the most money, and then Gary did the best job of making the most money and he bought the jets and then became symbolic, but he also created millions of hundred-thousand-aires, and millionaires.” That’s what’s Crush It is about, and that’s what Crushing It is about. I think that’s really cool.

I expend an enormous amount of time, trying to make my audience awesome, out of the selfishness of the legacy not to get them into the top of a funnel to buy my book, or my sneaker. I ask for it, but I have zero vulnerability or expectation. Listen, you have a great business around your brand. A lot of other people do. I think that’s great and think it’s cool, I just like that I make my economics in other places. But, I’m paying the price, I’m eating the s**t, like, one could argue, “What’s better?” but I absolutely think I’m going to win the game as “made most”, because it’s keeping score, I mean, it’s part of the equation.

But I’m not driven by that, I’m driven by, “Look, dude! You are crushing it! You are winning! You are doing so many great things! Do you know how amazing…?” You know Stephanie Land, my ghost writer, interviewed you for it, and then I’m going through it, just reading your story about the book, Crush It, and then of course I remember getting picked up and going to the Cost Plus and all that.

Lewis Howes:               I picked you up in a beat up car, and I had no money.

Gary Vaynerchuk:         But it’s fun, right? I mean, first of all, one thing I know is, everybody’s got it in them. It’s not like I’m manufacturing… You were doing the LinkedIn party stuff. That’s not Crush It, but man, I have definitely suffocated excuses better than a lot of people, which is really the biggest reason so many people who are listening right now are not winning.

They are surrounded by people who are willing to accept their excuses, on one very interesting insight: It’s because those people don’t give a f**k. Your friends and your family are letting you get away with your excuses because they don’t care. I weirdly don’t know you and I care, and let me tell you how to fix this: Get your excuses out of your mouth.

So, I think, between that and then showing people this whole $1.80 strategy. I don’t know if you’ve seen this. This has been great for me. You know, once in a blue moon I come up with very tangible advice, so I’ve been talking a lot about leaving comments on people’s Instagram posts, but not “follow me” or just a game it, no. Everyone’s like, “How do I grow?” I’m like, “There’s a way. It’s called a Thank You Economy,” quietly go and nice and calmly, if you’re a photographer, go to Nick’s page, he’s got legit s**t. He takes a photograph of some pretty boy or girl, he’s good at that, in some beautiful setting and then look at it and leave a comment that’s meaningful.

Like, ‘Hey Nick, are you using this filter?’ or, ‘I noticed what you did with the light there.’ Something meaningful, not, “Cool! Lit!” You’re not leaving the comment for the sake of leaving the comment, you’re taking the actual hour and a half to look, add something of value. You do that on ninety different…

The way I came up with it, was leave your two cents in a comment, leaving your two cents, go take nine hashtags that are relevant to your business and then go to ten accounts or ten hashtags, it used to be the top nine, now it’s just random nine, so pick ten hashtags, the random nine, that’s ninety, leave two cents, now you’ve left a $1.80 for the day. Watching the last two, three, four, five, six weeks of people… Because it’s funny, right? People are buying likes and comments. People are trying to do dumb s**t, giving away iPads, or Yeezys or Off Whites to get followers.

Or, you can actually work for an hour, know your craft and act like Nick, I’m actually looking at it because you know what would happen, because he actually knows his craft, if he actually spent three hours a day, three hours is a lot of time. But if he gave a f**k and I don’t think he should or shouldn’t, but if he gave a f**k, the fact that if he spent three hours looking at twenty hashtags in photography because he’s crafted and skilled and gifted, and went to those people’s photo’s and said s**t that I would never understand, I would just be, like, “Nice thong!” or like, “Nice muscles!” or like, “Cool coconuts!”

But if he said, “Oh, I see what you did there with the reflection, horison,” whatever, well that matters, because it’s like people see that you’re leaving something meaningful, right? I don’t even remember why the f**k I’m talking about that. But basically I’m thinking about bringing the most value. I think it’s mindset and strategy.

I used to not like the motivational version of me. I’ve gotten much more comfortable in the last eighteen months. Because I’m like, “Huh. If I don’t think of it as motivational,” and I thought of it as strategy, because mindset is strategy, right? Being insecure is a mindset that’s been put into you for a million different reasons. Figuring out how to get out of that hole by who you’re surrounded with, how you think, what you do.

Insecurity is the biggest poison in our lives. Insecurity scares the f**k out of me. Lack of self esteem is why people do everything bad. Buy dumb s**t to make themselves feel better, do dumb s**t , like take dumb s**t and put it into their body. It’s all insecurity. I used to, I remember, in high school, back to dating now, I’m going to tie these stories together, I remember when I realised, “Oh, my friends drink alcohol to get courage.” But they’re not even that drunk, they just use it as an excuse to do s**t that they wanted to do anyway. It’s just all insecurity, man. I don’t know.

Lewis Howes:               What’s your insecurity?

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

Lewis Howes:               Why?

Gary Vaynerchuk:         Because I think I should be nice, and I think I like people, and I think it’s a bad idea. I don’t know if it’s an insecurity. I don’t know if you saw I had Tim Ferris on my podcast and I apologised to him at the end, because in the early part of my career I got on a tangent in one speech at Blogs With Balls, where I was, like, four hours of working, go all in and it just, I didn’t like the way it came out. I knew what my intent was, which is why I was kind of fine, but I’ve been apologising to Tim for a decade. Because I don’t want him to…

Lewis Howes:               From that one speech?

Gary Vaynerchuk:         Yeah, because it hurt Tim’s feelings. Rightfully so. Like, if you go and find Blogs With Balls 2009, I went on a good three, four minute tangent. I didn’t talk about… I’ve never read anything. From what I know, 4Hour Workweek is about efficiency, not about working four hours. So, I look at Ray Lewis on your wall. In the right circumstance, at a Jets/Ravens game, there is no question that Ray would never remember, and this didn’t happen, but, Tom Brady. I hate Tom Brady. But do I? I hate him, right? But I would hate…

Lewis Howes:               But you appreciate him.

Gary Vaynerchuk:         No, no, I don’t even appreciate him. I hate, I know how Brady is, I’ve zero appreciation for him being great. None! I know it’s there, I don’t appreciate any of it.

Lewis Howes:               If he was on your team, you would.

Gary Vaynerchuk:         No s**t. And I hate him and I say it in public, and f**k you and this and that and at games and if he was on the sideline, I would flat out, like, “F**k you, you suck!” and mean it, right? But, in real life, if I cross paths with him, and I feel like, what scares me now is, I’m definitely going to cross paths with the Colby’s and Tom, like all these guys want to be entrepreneurs and will be entrepreneurs, so I’m like, “Uhngh… this sports thing’s weird now,” like I’m going to see him at some Allen & Co of society, and I’m like, “Uhngh…”

I don’t want to be disliked because I think there’s no reason to, I hate cynisism and hate. I hate it so much, and being associated with it would really upset me. I’m insecure at, I don’t know if insecure is the right word, but I’m aware that I’m awfully peacocky on stage, in a podcast. Like, you could ask me questions here and I could say s**t that I believe, but I don’t want to deal with the ramifications of my truth.

And more importantly, and it’s a great time to say it, and Babin, I hope you’re filming, there is something that’s really interesting to me, which is, I really know that I mean nothing. I think the biggest reason I’m willing to spit authentic, is because I don’t think so highly of myself, meaning I’m not insecure, it’s just like, me thinking Nick is not good at something, like business, forget about photography, who give a f**k? Me saying your business stinks, even with all my business things, I still think it’s just one dude’s opinion. I understand it’s a solid opinion, I understand that it comes with some heritage and value.

Too many great people who have won so much in things have told me I’m not going to win, and then I’ve won, that I know I’m the same. And so I think one of the reasons I’m willing to spit, is like, my opinion is still my opinion and like, take it with a grain of salt.

Lewis Howes:               You talk a lot about delayed gratification, there’s time, and everyone has a lot of time and people are wanting things right now. What do you think, even with that mentality, I know that you would love to get results, bigger results, all the time with what you’re doing. You know, if you sell 100,000 books, you would like to sell 200,000 books right now.

Gary Vaynerchuk:         That’s exactly right, micro/macro. That’s it.

Lewis Howes:               Yes, exactly. But what do you think you’re going to need to do to step into getting faster results. In the micro and the macro? What would take you to the next level quicker?

Gary Vaynerchuk:         I think what takes everybody to the next level, is cutting out dumb s**t. If you really look at anything, it’s always cutting… That’s why Jack Welch had such a good career, he was so right, like there was a revolutionary thought of like, “Cut your bottom 10% of your staff each year.” But he’s right, I mean, no question, whether in your training, in your business, in your friendships.

Do you understand that if every person who is listening right now started to weed off the friend that is bringing the least value, and I mean, they’re a bad influence, they’re bad mojo, they’re bad. Like in bad. They’re just negative. They’re a negative person, so they’re dragging you down, they’re selfish, they have bad habits, like a drug addiction or something. And you don’t want to leave them, and I want to make sure people… People when they hear me say this they’re like, “Oh, you’re, ‘Get rid of your friends’!”

No. Just, if you audit your circle of who you spend time with, if you just spent time with something that is broken and you added one person that was incredibly valuable. That’s just real and so I think the thing that I’m not good at, but I would never give it up, so I don’t know if it’s a strength or weakness. I do a lot of meetings on spec when people ask me to.

Lewis Howes:               Some of those pay off long term and some of them you’re just, like, “Am I wasting my time?”

Gary Vaynerchuk:         Even if this was back in the day, like, “Can I drive you to the Cost Plus?” I’m glad I did it. Now we know each other for a long time. Yeah, I mean, at this point, no question my time has become remarkably valuable and I still do 20% of my time this year will be highly questionable, if somebody was auditing my life. At some level you got to accept some of your humanity aspects, but I think that that is the thing that would take me to the next level: Getting even more disciplined on every single thing I do. Debating every single idea, that could be a good one. This is super funny, if Tyler was in the room right now, he would argue that I’ve made a mistake by being here today for an hour.

Lewis Howes:               Your assistant, Tyler?

Gary Vaynerchuk:         Uh-huh. We’ve got a lot of things going on. I’ll break it down. This is going to be interesting for people listening. We had a bunch of new business meetings, new people I could have met. High. Big. Good. Would have been on your biggest wall, right? You know, Tyler gave me a list of things and he said, “You can do one of these four things,” and I did this.

I would argue, somebody analysing me would say this is the wrong move. Couple of reasons: Number one, the new book, Crushing It, is selling so well, that I’m not even trading for speaking or doing podcasts. I mean, I’ve never been this passive two weeks away from a book release. I don’t even know what I’m doing. I’m like, this is like, I’m weirded out myself. I almost weirdly wanted to collapse and everybody returns to pre-sale so I get punched in the mouth for being so passive.

This audience, that is listening right now, has heavy crossover. I’ve been on this show not too long ago, a lot of people that like you like me and vice versa, so I get somebody analysing that how do you get better, that this was the wrong choice for the hour. But I just like you. I just wanted to see you. So, I think that’s like a human thing, sometimes you just have to do those things.

So that’s why I say, I won’t change what would make me better, but what would make me better is to analyse my time more fruitfully, for micro results. But for macro results, friendship, whose funeral are you going to show up to and why. I think this is the better decision. And so, I will always make a macro decision and I will take 100% of the macro results and only 60% of the micro results and I think everybody who’s listening, man, do I think 99% of the people try to maximise micro. Every person.

I’m blown away by people literally analysing, like, “What’s in it for me, in this microsecond of this thing?” Everybody. It’s so awesome for me to watch, because I’m like, “You’ve lost.” And people do that. And they do it when they don’t mean s**t. I love people getting put on just a little bit and they think they’re fancy and they just start… Anyway.

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

Lewis Howes:               He says good things about you.

Gary Vaynerchuk:         Right, and I know how well I know him and he knows how well I know him. We’re in between that zone of acquaintances and friends. We haven’t spent enough time, and by the way, I’m going to pull a tangent, aren’t you fascinated by the serendipity of something happening that takes an acquaintance to a friend? It’s usually predicated on something like a trip or some weird night where you were like… I’m desperate for one of my flights to be cancelled, and I’m there… A dream for me would be to go on a red-eye from L.A. to New York, that Nick’s on, it gets cancelled and for some reason it’s a blizzard and we can’t leave the airport, I know in those six hours sitting there, that’s where the friendship gets made. Love that s**t!

Early college is that for a lot of people, right? Remember that first conversation you had, probably round the first week of October with the kids you just met, and you stayed up to four o’clock and one dude cried, and forever that night, you like literally, like I’m literally still texting kids who are my friends twenty-one years later, off of that October 7th night where two people cried. I’m like, “I love you, dude,” and you’ve only known the guy for four weeks, but now you’re friends forever.

College is the biggest racket, and every college should go to jail for the debt structure that’s created around it, but no question, and that’s why I love, whether it’s a soho house, or the seminate C thing or South by Southwest, getting people to a place where they have to spend two or three nights together, is powerful.

I’ve actually been thinking about launching a club thing, that we’re, it’s called, Tuesday. I have this idea of a club, it’s called, Tuesday, and you walk in, and the only way you’re in this club, think Soho House, New House, think about those kind of places where you have to be there by nine o’clock Tuesday, and you don’t actually leave until 6am Wednesday. You’re stuck. There’s showers and beds and obviously some weird s**t could go down, but I don’t, not caring about the weird s**t, I’m caring about what actually happens when you’re forced to spend the night?

Here’s what happens: You’ll have dinner with people, but it’s what’s going to happen from eleven to three in the morning that will forever change your relationship with that person, so I’m trying to create a context of force. You know what I’m pumped about that we just said this, is this is now on the record. I’ve never said it out loud. I probably won’t do it, because I’m busy, but it’s now going to happen. And, of course, they’re going to call it Thursday to disguise it, like, “That’s my s**t, motherf**r, it’s Tuesday! F**ing Tuesday, you f**k.”

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

Gary Vaynerchuk:         Lewis is in it!

Lewis Howes:               I’m in the book. I think there’s a few pages of me, or there’s a whole profile about my story of reading Crush It, meeting you nine years ago and what the book did for me. And my favourite chapter is the one about caring and giving. I think it was the one-word chapter, Care, right? That’s been my approach ever since, I mean, I think I came from that before I read it, but when I read it…

Gary Vaynerchuk:         Sometimes when you put something on paper, right?

Lewis Howes:               Yeah, it was like, “Okay, what can I do?” and hopefully you felt this from me, that every year I’m thinking, “How can I give to Gary?”

Gary Vaynerchuk:         Lewis, let me say something about you that’s nice, because I’d like your audience to hear it, but more importantly it will help so many people. When you started trying to care towards me, as your career evolved over the last nine years, the first four times that you cared, I thought, this is the set-up for the other thing.

Lewis Howes:               The ask, or something, right?

Gary Vaynerchuk:         Because that is what we, as humans, think. That is the environment we live in. I’m sure that’s what people will feel about me. The fact that you, look, I think here’s the thing, actually, let me say this about you as well. This is a good topic. I want to pay forward at all costs. I want to give, give, give, give, give, right jab, left hook. Like, if I had it my way, that book would have been called, Jab, Jab, Jab, Jab, Jab, Jab, Jab, Right Hook. I think the thing that you have, that I have, and this is our kinship and, no question, speaks to our success, is we’re very willing to give, we’re not scared to ask for something in return, but we are not crippled, we don’t over react to somebody coming through, and we’re not crippled when they don’t.

I’ll give you a great example for everybody listening. When School of Greatness came out, you e-mailed and reached out, I was able to buy a bunch of books, we do all the right things. When Mask came out, this feels like, what? three months ago? I remember this clearly because I kept getting scared that I was f**ing up, because you reached out, you were like this coming, but I had some s**t going on, just business stuff.

Lewis Howes:               You were busy too..

Gary Vaynerchuk:         No, no, but I was just really between personal life and business, and I just remember, and I remember this because it was, “Oh, I got to reach out to him, I got to…” And then I hit you up and I was like, “Dude, where are you?” LIke, “Dude, I was in New York four days ago,” but you know what’s interesting to me? That! Because that’s how I play. Sometimes people will come through, sometimes they don’t.

Giving with expectation is a devastatingly bad idea that 99% of people do. And somewhere after the fourth time you asked to do something, I just like, “Oh, he f**ing figured it out!” so now I look forward to the asks, I want to support the asks, I’m always supporting the asks.

Lewis Howes:               Yeah, and, I don’t ever really ask, it’s like….

Gary Vaynerchuk:         You ask the same way I ask.

Lewis Howes:               Yeah, it’s like, once in a blue moon.

Gary Vaynerchuk:         Oh, dude, do you know how pumped I am that Crushing It is selling so well, so I don’t have to ask? Because I also have the next two K-Swiss sneakers coming out and they sold out so fast that they’ve produced so many, so I’m like, “I’m definitely going to flog them.” Like, “Dude, do you want to wear a fresh new pair of K-Swisses every day for the whole year? Well please buy 365 pairs of my next sneakers.”

Lewis Howes:               My mentality is also, I think that people listening can take a page out of this, and my mentality with you is, I’m thinking of how can I give to you without you even having to ask.

Gary Vaynerchuk:         Me too.

Lewis Howes:               I’m thinking, like, I made a couple, I don’t know if you saw it in the e-mail, but I made a couple of introductions where guys were like, “I want to buy a couple of books from Gary,” and I said…

Gary Vaynerchuk:         Yeah, like, making intro’s and like, “Hey, you know who buys four, five or ten thousand of yours, you made intros of people that… And you’re winning, because I’m not as easy to get to these days, so you won twice, and that’s so smart, right? These people, a lot of them have told you this, I’m sure, because if you intro, I’m saying yes.

Lewis Howes:               Or I say, the only way I’m going to intro, is if you buy 2,000 books.

Gary Vaynerchuk:         But even more interestingly, these are people that have reached out ten times that say, “I’ll buy 3,000,” and I don’t reply. And then you do it, and I do, which I know makes you look good… But for me, the best part is, now that I’m in a different kind of like, as my brand grows, as my career grows, as my reputation grows, it’s reputation, because when I, you say brand and a lot of people like, “Uuhh…” Reputation. That’s what it is.

What’s been fun for me, is when real senior people. Not for people with 10,000 Instagram followers, I mean the seventy-four-year-old lady that’s running the world that you haven’t heard of. What’s been fun for me, and this is the thing that, back to Nick, what he says behind my back. When real power players, like 80 billion dollar hedge fund people that want to invest in something, or somebody deciding, even when you’ve got somebody as incredible as Scooter behind you, when you’re looking at TV stuff, when there’s people that are on the board level of a network, saying, “Hey, this guy’s coming through the path. We’re trying to…” You know this.

Anybody that’s growing up in our era, everybody’s trying to figure out, is this real? Or is this fake? Is this a real dude? Nothing is more fun now. Look, buying 500 books is the easy part. Me putting my reputation on the line for somebody else, is the thing that scares the s**t out of me, and I think the thing that’s a lot of fun, and this is the hidden thing, that all the kids and even the seventy-year-olds that are in kid mentality don’t get it…

I had a meeting, I was with Scooter today. We talked about the game. We talked about multiple people, that we’re fine with, we like, but deep down, everybody knows this, there are plenty of people that feel, that you have relationships with, that that person will feel like you guys are fine. Why would I say something bad about somebody? Like, when there’s no benefit? But if somebody said your reputation’s on the line, and this happens in real life. Guys, this is what is happening, just so you know what happens as you continue to try to build your game, there’s always this moment. There’s so many huckster kids running around right now, who claim to be friends with all of us, who, all of us are nice people, but behind the scenes, if you’re a huckster and you’re doing it just for you, and you’re name collecting, to get selfish, short term s**t for you, let me tell you what’s happening: At dinner, four of the people who are really winning, are having dinner, your name gets brought up because maybe the fourth person say, “Hey, this kid’s been reaching out to me and says he’s homies with all three of you, ironically, what’s the story?”

You are getting s**t on. You think you’re winning, and again, on a micro level, you are. Like, that person’s commenting on your Instagram post. You’re at a conference and they high five you and give you a hug, but the truth s**t. I’ll wrap it up perfectly. The curtains look good, the painting looks good, but the foundation is broken and you’re, here’s the punchline: The four titans that are winning, they’re not wrong, because they’re just being polite. You’re wrong, because you’re doing behaviour to gain those titans for your selfish needs, and you look like an idiot to the 1% and you look cool to the 60% that don’t matter, and the 39% in the middle are trying to figure it out. Too many people winning with the 60%.

Lewis Howes:               What advice would you have for me over the next ten years? You’ve seen the first ten years from Crush It, to Crushing It, now, and my career evolving. This is for a selfish reason, I think, it’s just, like, a teaching point.

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

It’s actually binary. “Should I buy Prince, the tennis racquet company, and do I want to buy a company? Do I want to start a company? Or do I want to triple down?” For you to have this much brand awareness around a human, you’ve got to decide if you want… If you look at all these pictures, a lot of those people make the majority of their money being that human, but if you look at the CEO of Spanx, or if you look at somebody else, I’m in that category, they’re making their money other places and happen to also have that.

You need to decide are you going to still just only be Superman, or is there a Clark Kent in your repertoire? And that doesn’t mean that you have, like, I’m looking at Logan Paul who is obviously going through his own stuff and whatever right now, but he makes hoodies and makes millions of dollars. But that’s 100% still on his brand.

That’s different than VaynerMedia, that’s different than Spanx, that’s different than my ambition to buy K-Swiss and be the CEO of K-Swiss, and it’s not because I’m the face of, I’m the operator. Do you want to be the operator of a business that 90% of it, the customers don’t care that you’re this person, or do you want to continue there? I think that’s the most interesting thing for you to think about, right?

Lewis Howes:               Yeah. That’s good. Good advice.

Gary Vaynerchuk:         You know, Phil Nighy and I’m looking at all these things I’m looking at, books around here, they didn’t have that. There was no way for Phil Nighy to make four million dollars a year being Phil Nighy in 1984. All these younsters, now, can do that. You’re a youngster. What’s interesting is, our mutual friend, Adam Braun, there was no kids building huge non-profits, so him, when he wanted to go on and build a business, there was this weird dynamic of, “Wait, you’re not allowed, you’re non-profit.” Of course he’s allowed, but he’s a first generation, where kids started non-profits from the get and then go private.

Same for you. You’re part of the generation that can make a great living just being the person. Now your question is: Do you want to build a business that is scalable outside yourself, or do you want to quadruple down, and true, they’ll both work, it’s just up to you.

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

Gary Vaynerchuk:         51:49, I would draw that first, and then I would in parentheses explain and I would say, “Give more than you take.” And then, we talked a lot about that in the last fifteen minutes, it just works. And the reason 51:49 works, is it painted a picture for everybody right now, who’s been listening for the last twenty minutes and are like, “That’s an interesting insight, of why Gary and Lewis are winning.” That’s the right number, to me. And, for me, it should be 50,1:49.9, but then you can still be selfish in the power of your selflessness.

So 51:49, I would say, legacy over currency. How many people show up to your funeral, is the KPI. Because if you’re great at that, you’re going to have money. Occasionally you have somebody who is a teacher, or sat on the porch of a town and everybody loves him, but most people that have ten thousand people or five thousand people show up to their funeral, and by the way, just being loved is better than having money, I mean, how much money do you need? So anyway, legacy over currency.

And then, the third one would be patience. It is the disease of our society, the lack of patience, bro. I mean, it’s crazy to me that, literally, patience and insecurity is 90% of the unlock for everybody listening right now. Their mom hated on them all their life and told them they were going to be a loser, they believed it, that’s what parenting is, and they just want to have a Maserati now, and they’ll do whatever it takes to do it.

And so, they’ll take… You know how many kids are doing something smart, like doing a good retail arbitrage on Amazon right now? And making $100,000 by buying an Ali Baba and selling it on Amazon, it took a year and a half, three years to get good at it, but now we’re taking every profit and buying some rando crypto currency, because they’re playing the lotto? This is what’s going on in our society. We have to have these conversations.

Lewis Howes:               You’re saying big gains fast.

Gary Vaynerchuk:         Like, there’s a kid who’s spent three years being disciplined and getting good at retail arbitrage, it’s a real skill to have an eye for what to buy in China, how to set it up on Amazon properly, how to run an ad, like, it’s a skill. They did it for three years meticulously, they made $13,000, now they’re finally making $300,000 and they could be on their way to 10 million, yet, they’ve chosen  to kind of stop, jump on the short-term bandwagon of buying some weird crypto currency, hoping it’s the next Bitcoin, or Ethereum, I’m just seeing that every day, and I’m just, like, it’s being predicated on short term.

You hear one story: “Zucks did it.” “Instagram sold in 550 days for a billion, now I’m…” Everybody started an app company. The follow the leader s**t, completely predicated on short term.  I went the other way. While everybody was blowing up, I decided to build an agency. Boring, s**ty-a** business, in the prime of my career, when everything was going for me in Silicon Valley. I’m proud of that. I think I’ll be historically correct. So, those are the three things I would say.

Lewis Howes:               That’s great. Before I ask the final question, make sure you guys get the book, Crushing It. It’s out now, you can pre-order it, or it’s out now. Get the audio book, pre-order that, which is coming out in a couple of months, I think. If you don’t already follow Gary, make sure to follow him @garyvee, Instagram, seems like it’s your platform of choice these days, it’s been crushing it. Literally, it’s been blowing up in a massive way. Your attention there is unbelievable.

So, go follow him there, if you’re not following him already.

One final question. Before I ask I want to acknowledge you for a moment Gary, for constantly showing up. Since I’ve known you, 2008, 2009 you’re constantly giving. You care deeply about everyone. You always want to give, and you’re doing things that aren’t necessarily the most popular things, to support other people. So, I want to acknowledge you for constantly being yourself. Speaking your truth. You never hold back, just like now, you’re always going to say it like it is. Your authentic ability to give, to speak what’s on your mind. I really acknowledge you for that. I appreciate it.

Gary Vaynerchuk:         I appreciate it, brother.

Lewis Howes:               Final question, what’s your definition of greatness?

Gary Vaynerchuk:         I’ve never really thought of that. You know, it’s funny, couple of things ran through my head. I’ll just go with what ran through my head. First thing that came to mind is that a lot of people know who you are, because you’ve impacted them in a positive way.

The second thing that came through my mind was interesting, was, when you say somebody’s name, you feel something. You know, like when you get nervous, some version of excitement and butterflies, I’m fascinated by the word, “great”, because I think it’s one of those words that has absolutely been… I think about sports casting, it’s funny, everybody’s nostalgic about their youth, and you just become the old man or old woman, the way “great” gets thrown around, you know, I’d love to get your perspective on this, because you’ve anchored into this so heavily, but, like, those are the two things that come to mind.

Like, that mix between nervousness and excitement in your stomach, or to me, when you hear a name, like it’s funny, Martin Luther King’s birthday was the other day, right? I went to Martin Luther King Middle School. I don’t think we can wrap our head around the people that have changed the world. Because that’s a level of selflessness.

Like, I’m pumped that I’m going to be 50% selfless and I think I’m going to be legendary for it. There’s people out there who are 100% selfless. I think, for entrepreneurship you have to be 50% of each, but it’s wild to me, that I am going to be far more successful and great, because of the DM that I’m going to send to a kid tonight, than for the 97 things I’m going to be right about in the next century, and will make me successful.

Doing the right thing is always the right thing. There’s something in that statement. With greatness, I think you have to be great to be an enigma, you have to be against the status quo, you have to be willing to say, “F**k work/life balance, in it’s current state,” like I did earlier in the segment, so, yeah, just different. And invoking the reaction. A human reaction must occur, otherwise you’re not great.

Lewis Howes:               Gary, thanks brother. Appreciate you.

Gary Vaynerchuk:         Thank brother.

Lewis Howes:               There you have it, my friends, if you enjoyed this special episode with Gary Vaynerchuk, then make sure to share this with your friends. Tag me on Instagram with a screenshot of this podcast image, and let me know what you thought. Tag @garyvee as well. I’ll be screenshotting them, posting them on my Instagram story. Retweeting them, posting them on Facebook, so make sure to tag both of us, @LewisHowes and @garyvee on Twitter and Instagram with what you thought about this episode. And if you did enjoy it, make sure to leave us a review over on iTunes, again, you can do it right on your podcast app if you’re listening on your phone, or go to, and leave us a review, for your chance to be shouted out as a Fan of the Week.

Also, make sure to pick up a copy or two of the book, get one for yourself and give one to a friend. Again, I’m in the book, so I’d love to hear your thoughts about my case study of my journey. Again, so many people are always interested about what I’ve been able to do over the last eight to ten years, and I talked a little bit about the things I learned from Gary’s original book, Crush It. And how I’ve applied that specific principle towards my business. So, I’ve learned a lot from that book. Go check it out. Get a couple of copies for your friends as well.

And a big thank you to our sponsors, which is Bench. Again, if you want peace of mind, if you want to save time, and you want to have less administrative stress, I’m telling you guys, you need to have your bookkeeping in order. And is going to give you a free month of your bookkeeping and provide you with a set of financial statements for free. Go there right now, guys,, test it out for a month. If you don’t like it, you don’t have to do it any more. I’m telling you, this will save you so much time, so much energy, and it will enhance your business’ financial health. Go there right now, for your free trial, at

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Again, if you enjoyed The School of Greatness Podcast and if this is your first time here, then welcome. I hope you subscribe to the podcast and if you want to watch the full video interview you can do that as, for this episode with Gary Vaynerchuk. And if you’ve been here many times before, then welcome back and thank you for constantly listening and sharing this with your friends. Our mission is to bring you the greatest and brightest individuals in the world to help you unlock your inner greatness. You were born for greater things than you have right now.

And Ralph Waldo Emerson said, “To be yourself in a world that is constantly trying to make you into something else, is the greatest accomplishment.”

All you need to do is become more of you. Continue to overcome your fears. Continue to step out of your comfort zone, to grow, to learn, to develop, to tackle life’s greatest challenges and become your best self. Be yourself and become your best self.

And you know what time it is: It’s time to go out there and do something great!

Music Credits:

Music Credit:

We Were Infinite by Inukshuk

Sea You Soon by Cinnafinn

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