I had the fortune of interviewing Gary Vaynerchuk, CEO of VaynerX and creator of Wine Library. He’s who inspired me to be the entrepreneur I am today, he’s one of the main reasons I get to do what I love every day. Gary provides ample words of wisdom to not only benefit myself, but anyone with a passing interest in improving their work ethic or outlook on life.


Jas: It’s been amazing not only for my team to see, but really for the world to see what you’re doing. I could talk about all the little things that I’ve copied you on because you’ve allowed it, but I really want to give back. I can’t pay you back for what you’ve done and the education that I’ve gotten from you. I want to talk a little bit about something you’ve taught me: patience.

Gary: Yes. Patience comes hard for alphas.

Jas: What do you mean by that?

Gary: Well when you’re hungry and ambitious and want to fuck up the world and want to dominate, patience seems foreign. It seems anti-cultural. When people think of themselves like “I’m gonna win.” They don’t normally think I’m gonna win in 80 years.

Jas: Where did you get the patience from?

Gary: I think I’m way more practical than people realize because I’m so high energy and sometimes that seems less practical. I also think it’s based on my ambition. My ambition is not to own a Lamborghini. My ambition is not to own a mansion. My ambition is to try to buy the New York Jets. That’s my kind of selfish, kind of fun ambition. My immigrant rags to riches kind of thing. My ambition is to leave a legacy, and that’s forever.

Jas: Let’s take it back for a bit. There’s a couple of people who don’t know you are. What’s your origin?

Gary: 1.3 billion don’t know who I am. I’m an entrepreneur immigrant from the former Soviet Union. I grew up a hustler kid in Jersey in the 80s and 90s. I’m all those cliche things: immigrant, cursing, Jersey, competitive, feisty, hungry, ambitious. But I’m also Tamara Vaynerchuk’s son, she is an emotional, intelligent juggernaut. She’s quiet. She’s a mother of three. She is not super social. She’s definitely not out there but she has talents with empathy and gratitude and kindness that I completely absorbed DNA wise and then was parented by. So I think I’m an unusual alpha business winner, in that I’m building big businesses, I invest in a lot of big fancy companies. All my Tumblr and Facebook and Twitter and Uber stuff around here. I’ve built multiple huge companies and I’m a successful and wildly followed on social media entrepreneur. I think I’m coming at it in such a different way than the other people that entrepreneurs look up to and I think it’s the thing I’m most proud of, which is I think I’m putting words [into minds of] especially alpha males but alpha females too. I’m putting words in the vernacular that had just not been part of the winning business culture. The words empathy and gratitude and kindness and patience were not the words coming out of 26 year old entrepreneurs saying that they’re going to kill it or crush it.

Jas: Well there are a lot of people want to tear down buildings, not help others try to either build up theirs or just build bigger buildings, like you say.

Gary: Yeah. What you’re referring to, and I appreciate you calling that out, is one of my favourite things. I think if you’re great you don’t spend time tearing other people’s buildings down. The reason I give away all my best advice is because if somebody is better executing than me it’s going to happen anyway. So I think the world has abundance. My success is not at the expense of anybody else’s. Nor is it the other way around.

Jas: How did you get so fucking quiet in your head? Because I’m getting there and I’m not just saying that.

Gary: Practice. See you just said something very important, you said something powerful. “I’m getting there.” Why? Because you’ve listened to me, and it became something you’re believing in. And once you started tasting it you can’t untaste it. It’s very unnatural to think giving more than taking leads to more for you. But it’s the truth. Especially if you’re talented.

Jas: Do you think it’s egotistical?

Gary: I think it’s self-awareness. I’m incredibly confident and I think ego is insecurity. So I think it’s confidence speaking and then I think confidence is more palpable when it comes with humility. Listen, there’s a lot of people who see one Instagram video of me for a minute and they’ll not like me because I’ll be hot and excited or personable. The reason I think most people end up liking me, if they really go down the rabbit hole, is there’ll be something that I’ll do that will make them realize in all the bravado and all the East Coast, there is an equal amount of humility, patience, kindness and it’ll be that light that will be: “I didn’t expect that from him.” And I think that that’s important. I think you know that just comes with the mixture of DNA and experience. But for me I got quiet, and what you’re referring to, if people don’t follow me is I talk a lot about being quiet. If you go to my latest post on Instagram there’ll be eight hundred people that are saying outlandish things like “you’re Jesus!” I’m like “alright, let’s calm down.” People really get fired up about me and then there’ll be eight people that are like “you’re a snake oil salesman, you’re full of shit. What the fuck, this guy’s getting rich over talking about common sense.”

Jas: Look there’s people that knew I was going to come see you and they were thinking you’re a snake oil salesman, because they haven’t dug deep enough.

Gary: The reason I don’t get upset when people kind of take a hot take at me is because I don’t have the audacity to think somebody should spend an hour digging into me. Are they supposed to spend an hour consuming all my content to get a good read on me? I think that’s audacious. I think that’s insecurity. So when people have hot take, I get it. I know how excited I can get. I know that in a 30 second video how I can come across because when the lights go on I feel like I’m an athlete. The lights are on, I’m in. And for me when the lights are on a piece of content that’s me when I’m wearing my uniform and performing. In real life though, I don’t have athletic ability but when I try to scrap it up with friends I’m dirty, like I want to win at all costs. When the game’s over I’m not happy I tripped that guy. I don’t feel good about it. It’s just I can’t help it. And I think that’s if you’re self-aware enough and that’s what can come across in my content. The reality is the truth always speaks in the end. You know there’s a lot of fake good guys out there. And I like that the world starting to expose them. I like it a lot.

Jas: Do you think it’s the cameras and social media? That’s the shit that’s going to expose them?

Gary: A hundred percent. Do you know how many guys are walking around scared right now? Why? Because they know they pinned a woman against a wall and did something inappropriate 13 years ago. I walk around light as a fucking feather. I knew that was going to happen 20 years ago. And because doing the right thing is always the right thing, it’s something I say a lot. I’ve loved that I was parented by a tremendous mother so I know who I am. I’m not perfect. I’ve got plenty of shortcomings but I know what I’ve done and what I haven’t done and you live that life and I’m also willing to deal with my circumstances when I do the wrong thing. When I make a wrong business decision and the business feels the effects of that. I don’t blame other people. I’m extremely accountable. And people get mad at me for that sometimes. That’s not a good way to look at it, you get depressed. Optimism and confidence along with accountability is incredible. I have accountability. I also say don’t beat yourself up. I don’t judge myself. I am fully accountable yet I don’t have the ability to judge myself when I fail.

Jas: How does that happen?

Gary: I think in general a lot of what I am is a contradiction, and so I think that’s where a lot of this is happening. So I’m able to be accountable but I don’t dwell. Being accountable doesn’t mean you beat yourself up. I never say I suck, but I’m aware that I lost. That’s different. Just because you lost doesn’t mean you suck. And that’s how I think about it.

Jas: It’s not the final score.

Gary: I like boos in the third quarter, I use this analogy lately. I like it. I actually thrive over that. I think a lot about basketball because I get really into it last year, the Knicks were about to have a big off season. I’m a Knick and Toronto goes on a 13–0 run to start the third quarter and we call timeout and the whole Garden is booing, I love it. And this is something I’m trying to figure out how to explain to people because that booing is killing everybody. And now that we have social the booing is on the record. People are crushed by negative feedback from their mother, from their spouse, from their boss, from the general public, from anonymous comments on social. And I feed off of it. I laugh when I see kids or people trying to hate on me. If this person knew that negative content is actually feeding me, and not bringing me down, they’d be so fucking devastated. They’re literally spending 20 minutes right now to try to hurt me, and they’re actually feeding me to be stronger than ever. I never reply to somebody who hates me because I think I don’t want to deploy negativity. I don’t like negativity. So somebody shitting on me, if they actually knew the truth, which is that it actually feeds me. I think I’m scary because I can’t hear you. You say I’m the best. Cool. You say I suck. Cool. You try to hurt me by saying I suck. Cool. When you’re not penetratable by outside feedback you’re fucking dangerous.

Jas: We were talking off air, you asked me how I heard about you and it was a few years I saw a YouTube video, you talked about Smurf It Up. How did that come about?

Gary: Oh, I’m so improv. I was giving a keynote and I was trying to make a point. This was 2008, and that’s the talk that made me write Crush It. I got offered to speak at this Web 2.0 Summit in 2008 at the Javits Center. And there was two very important tech guys in the green room with me, Fred Wilson who’s an amazing all-time venture capitalist here in New York and Jason Freed, the incredible founder of 37signals, wrote a book called ReWork; actually a very different point of view of work/life balance to the extreme. I’ll never forget this. I looked at both of them and I remembered the energy I felt, I go “something’s about to happen.” Either good or bad but I could feel the chemicals in my body being different. I haven’t spoken a lot at that point. This may be my 10th speech ever, 8th or 9th. Super early.

Jas: You could feel your passion in that.

Gary: I felt it in that moment. And the moment is what basically has happened in the world which is I just knew in 2008 for sure, it was like that the world was about to change because of the Internet. And social media in a way that nobody was understanding, that everybody had a chance. The Internet doesn’t care what country or what your race or gender is. It’s the truth. People are shitting on it. They should be loving it. They’re shitting on it because they didn’t realize how fucked up we were and we’re getting exposed by the Internet, by social. There is no social network. There’s platforms that we feed all on everyone’s social. Social media doesn’t suck. We suck. Social media is the mirror. It’s funny to me when people say Facebook sucks. There is no Facebook. Facebook isn’t CNN and Fox News. Facebook is a platform. We’re Facebook, whose Facebook? Zucks is not posting, we feed it. Your Facebook, your fucking FaceBook. But I mean every day now people say social media is ruining us, we’re ruining us. We fill the pipes, we’re the water in the pipes. Our water is contaminated, we’re the problem. Which is amazing because now we’ll eventually get there and then we’ll fix it and get better. I just knew where that talk was going to go. I went out there and I just shot my shot. I do and everybody’s like “look this is the greatest year ever.” I told everybody they can do anything. Let’s not think about trillions. Let’s think about tens of thousands and be happy. It’s funny when people say, “Gary, you push hustle and burnout.” What are you talking about? My signature talk is about being happy, making eighty thousand a year talking about Smurfs. That is the polar opposite of burn yourself out and buy a mansion. Everybody’s thinking I’m pushing hustle porn, I get it, I like hustle. Yes, I think work ethic matters, but equally, please listen to what I’ve been saying for a decade. I want people to be happy, if you’re happy making $42,000 a year working at Rogers at a 9–5 in Canada, fucking live your life. I’m not judging. That’s basically what I was saying there, which is Smurf It Up. If you love the Smurfs more than anything else in the world please start a Smurf podcast or video show at night. Maybe three years later after doing it every night, because you will do it every night, because you want to talk about Papa smurf … you can build a little niche audience. What this all means is if you have a passion or an interest or a hobby, I believe your hobby can be your business. [You can be successful] if you start making content around it in podcast, video or written form which eventually can lead to you selling merchandise eventually lead to you being the speaker on the subject matter, a personality, a subscription based business and events business. Smurf Con once a year in New York and you make a $100,000 and your life is better doing something you love. Maybe something as small as Smurfs can only make you $200,000 a year and you might be making $330,000 as a corporate lawyer, but I’m saying do that and stop buying fancy cars and homes and jewelry so that you’re happy. This has all been one game for me over the last ten years to get to this place where I can articulate what I mean which is let’s get happy out here, we have to redefine success. Success cannot be Lamborghinis, mansions and boats. Success has to be being happy because people are not happy and happy is fun. That’s what led to keeping up with the Joneses. That’s what’s led to me going hard after mothers and fathers.

Jas: Please elaborate on that.

Gary: Most people are unhappy because their parents fucked them up because they wanted them to be doctors, lawyers or engineers. Or because the parent is unhappy themselves, so they’re deploying misery loves company. My big thing is you don’t have to hate your mom. If your mom fucked you up because she’s the negative one you don’t need to hate her. You need to go up the ladder. Your grandma fucked your mom up. Put pressure on the person that’s negative and you’ve come to realize it’s your mom or dad; don’t hate them, actually be empathetic to them, just don’t live under that Geist. That’s a big one because what it’s going to lead to if you don’t forgive and understand they got fucked too, then you’re going to resent and that’s going to encompass you.

Jas: And that might go down to your kids now.

Gary: My hope is the ones that are consuming me are going to be the ones that stop it. It starts with forgiving your mom because they have to realize it was her grandfather and then they realized it was her great grandfather. And then you start realizing your mother didn’t have the luxury of the Internet where she could have stumbled upon somebody like me. It’s not that I’m fancy. I’m just saying they didn’t hear other voices. We live in the generation of hearing other voices, people focus on the extreme shit that’s getting banned and all that. What about the positive shit? Do you know how much we can change people? This is why positivity needs to get louder. I’m not on Twitter and Facebook and Instagram trying to debate everybody like everybody else is. I’m not trying to convince anybody, convincing doesn’t work. You’re not going to convince somebody that sees the world differently to see it your way. That’s audacious. I’m gonna live and create examples and create collateral happiness and positivity.

Jas: I know you speak about your mom a lot, about her giving you this self-esteem. How did she bring that out?

Gary: She overemphasized when I was being kind. “You’re a nice boy. That was so nice.” When I was nice to kids that were getting picked on, she made that a big deal. She also held me accountable. Report cards, punished. 0–4 in baseball, you suck, not the coach, not the sun was in your eyes, not anything else. So it was a positive reinforcement of good behavior and accountability when results weren’t there. I think a lot of people go over positive and it becomes delusion. I think that’s why we have a soft culture. That’s why I talk about eighth place trophies. I think that’s a place where we’re hurting kids. So what if you suck at baseball?

Jas: Pick up basketball.

Gary: Or program or sell lollipops or be a designer or do post edit production. Nobody is good at everything. LeBron sucks at science. That’s why athletes and actresses and singers are put on pedestals. Who were they as kids? They were pot committed to their talent.

Jas: Your company VaynerMedia, now VaynerX, which is the holding company of how many companies?

Gary: 4, 5 or 6.

Jas: How many employees?

Gary: A thousand.

Jas: There’s so many people who want to build bigger companies, how did you scale so fast?

Gary: By not caring about profit. Most people don’t build big businesses because they take the money off the table and buy dumb shit. We went from $1 to 3 to 14 to 27 to 58 to 73 to 100 million in revenue. Which is great obviously. But I never made money.

Jas: Went right back into the business.

Gary: Yep. You know a fun thing right now that’s going on in my world is people like “Gary V, you’re full of shit! You’re saying that you made no money in your 20s but how the fuck did you have money to invest in Facebook and Twitter?” I saved. When I made $43,000 one year I saved $5,000 that year. You know how many people make $43,000 a year and collect $8,000 in debt because they needed to go to Coachella and drink Blue Bottle Coffee. I lived in $1,100 a month apartment and I bought nothing and went on no vacations. I bought no clothes. Didn’t spend any fucking money. I don’t buy shit.

When did you see my content model?

Jas: Two years ago.

Gary: I’ve been saying it for ten years. You just saw it two years ago and you just started to execute, people have been watching me for nine years and still aren’t executing. I’m giving you the fucking blueprint. There’s no funnel here, there’s no mastermind. There’s no e-book to sell. I’m giving it to you.

Jas: I can not believe you put that out. It is ridiculous. We have six copies printed at our office because everyone has to have it. I’ve only done 15% of it and my whole fucking business has turned around.

Gary: Brother, I want to be the greatest entrepreneur of all time. I don’t know if I will be.

Jas: How do you decide that?

Gary: When do you know that you’re the greatest entrepreneur of all time. You don’t. That’s part of it. I don’t get to decide there is a trophy, this is about intent. This is where I think people don’t understand the bigger meaning of what I’m saying when I say I want to be the greatest entrepreneur of all time. It means that I want to give to entrepreneurs at a level that nobody’s ever given before. Doesn’t mean at 87 there’s some fucking weird Academy Awards. That’s not going to happen. I don’t believe that she or he is going to make the most money. Nobody gives a fuck when the person with the most money dies. People care when somebody who gave dies. When some random person with $19 billion from the Forbes list does, nobody gives a fuck. When Prince dies we shut down for a day or two because he gave through art, something that impacted you. You gave a fuck about Purple Rain. I always tell people about entrepreneurship, it’s like fantasy sports, nobody cares about anybody else’s fantasy team. Nobody gives a fuck how much money I’m going to make. When somebody sees Warren Buffett or Zucks or Bezos, they wish they could have that much money. They’re not like “Yay Bezos!” Nobody gives a fuck about anybody else’s money. People care about what you did for them. That’s why I have a shot because I’m going to spend the next 50 years giving to the game that gave to me. You care more about me because you started the meeting with “I can never pay you back.” Think about how that makes me feel. That’s amazing. You know how many people are like “Gary Vee’s an idiot, that dude would have paid $20,000.” You’re an idiot. You’re playing minor leagues. I’m trying to go to the Hall of Fame

Jas: One other thing quickly, Empathy Wines. Why do you call it that?

Gary: It’s the single word that I most resonate with most. I think being an empath has changed the course of my life. If that trait didn’t come to me through the DNA strands that my mom and dad gave me I would be a very different man.

To see more of Gary Vaynerchuk, click below to follow his social channels.

Twitter YouTube Instagram

Comments are closed.