Hustling superstar interview: Gary Vaynerchuk shares his entrepreneurial sales philosophy

Hustling superstar interview: Gary Vaynerchuk shares his entrepreneurial sales philosophy

I had the pleasure of speaking to hustling superstar and entrepreneurial energizer bunny Gary Vee last week and I'm thrilled to share this video interview with you. Here's what Gary had to say about this interview:


Gary has been interviewed at least a million times but never had an opportunity to talk about one of the things he's most passionately about: sales. Well, that has changed now :)

I apologize for the poor video quality. I promise the content is more than just worth it! Enjoy :)

You can also listen to the audio-only version of this interview. And check out these posts Gary wrote inspired by this interview:

  1. How to Sell Wine as a 15-Year-Old Kid
  2. The Dark Side
  3. Disrespect for Customers


Steli: Hey, guys! This is Steli Efti, co-founder and CEO of Close. Today I have with me Gary Vaynerchuck, the one and only hustling superhero. Gary, first of all thank for taking the time to talk to us.

Gary: No worries! I’m super flattered for the interest.

Steli: Awesome! I’ve watched tons and tons of interviews, your talks; your passion really is super inspiring. I read all your books and that, but one topic that I always wished there was a little bit more time for you to explore and expand on is the topic of sales and the entrepreneurial hustle so today I want to talk about that with you.

I’ve heard you before describe yourself as a salesperson?

Gary: Yeah.

Steli: I’d love to know when you had that realization for the very first time. When was that moment where you thought ‘What I’m doing, what I’m good at is called sales and I like it.’ When was that time when you actually realized that?

Gary: For me it came in a couple of waves. I talked - and it sounds like you know a lot about my stuff and I think a lot of people that watch this know my stuff, for the ones that don’t, I talk a lot about selling flowers at four and lemonade at six. It really, really hit me in fifth grade; I was selling lemonade but it seemed like a thing kids did, right?

Steli: Right.

Gary: I think when I really realized I was a salesman or I like selling was when my baseball card obsession started around nine or ten or eleven years old. There was a baseball card club in sixth grade, actually, when I was a little older. I just remember my teacher was like paying attention to me and knew that I was ripping people off. It sounded like a bad thing but I just thought it was good salesmanship. We all had the same price guide. I wasn’t tricking people; I just convinced them that my product was undervalued and their product was overvalued.

I would say somewhere around eleven I became a salesman. That got really reaffirmed at fifteen when – knowing nothing about wine – I was selling a boatload of wine in my dad’s store. There were always excuses like maybe I’m just cute. It wasn’t excuses, that’s the wrong word. There were always curiosities as to why. It was probably around fifteen or sixteen it became like, “I’m great at this!”

You’re right; I think of myself as a salesman as much as I think of myself as an entrepreneur. I think I’m an entrepreneurial salesman. A lot of people in tech are entrepreneurial developers. I’m an entrepreneurial salesman and I would say between ages nine and fifteen is when that got honed in.

Steli: Let’s talk about the wine store experience in selling wine because I think that’s such a fascinating product to sell.

Gary: Hold on one second.

Steli: Sure.

Gary: Hotel life, fellows!  Hotel life.

Steli: Selling wine.

Gary: Yeah.

Steli: You just said that when you started selling wine and selling a shit ton of it without even knowing what you were doing. Tell me about the experience of (A) kind of experiencing your dad and other people in the store that might have been seen you selling wine and having experienced that interaction and when you started doing it, what was your angle? What was your approach? How did you interact with customers and why were you ultimately successful at selling that product?

Gary: Here’s an interesting insight that I haven’t thought about. I spent very little time patterning myself or looking at anybody else selling. At that point, by doing fifty baseball card shows at fourteen or fifteen or maybe more, I already thought I was a better salesman than my dad, than Bobby, than Dick, than Carl, that anybody in the store. Those are real names, by the way.

It’s kind of funny. If you can go in the zone; when I’m selling I’m in the zone, right? I don’t even know if anybody else existed. A customer walked in, I targeted them like a shark and my angle was anecdotally, when nobody was selling while I was packing out, reading the back of the wine label, reading the sign that was on the display because we had signs. Maybe I would ask Dick who was the senior wine guy a question or two. I educated myself. I also paid attention to how other customers talked to each other which I think is an interesting tactic.

You’re right, I haven’t done a lot of videos on sales. I’m exploring some pipe works in my brain that I haven’t been into. I spent a long time watching how people sell people when they’re not the salesman and I think that’s attractive.

Steli: Right.

Gary: If you look at the tactics of when somebody is not the salesman; one thing I’m dazing into right now is the thought of other customers who are really good at selling customers on line. I would be standing by somebody; I remember other customers being more attracted to hearing that person say it than me saying it because there’s an authenticity to it, there was no vested interest. I remember even thinking it would be smart to have fake customers to do that.

I think I’m a great salesman because I listen and watch. I’m behavioural, it’s hunting. I look for patterns; I pay attention to what people do. I’m a conversion guy in an emotional way more so than in an analytical way. My style was listening to them and ask them questions.

Here’s a good example. "Hey, can I help you?" - "Yeah, I’m looking for some wine for a party." I would never go, “You got to look at this!” I would keep asking questions. I think historically I’ve always asked more questions, it’s why I’m good on Twitter; I do a lot of back and forth.

Steli: Yeah.

Gary: I would say, “What kind of party are you having? Are you having your boss and you want to impress them because maybe we should go in a direction of a name brand? You’re having just your buddies over for an NFL draft and they all really drink beer and they don’t know the difference? Here’s the best eight-dollar wine that acts like a fifteen-dollar wine.”

I did a lot of listening. I’m hyper and I speak fast so I throw four different scenarios. I would throw four different scenarios at them in a two-second period and be like, “For a party? For a boss? For friends?” I would react to body language.

Steli: The difference between asking a question so you get the permission to talk versus asking a question so you get a real understanding, like really getting into the mind of the customer and the needs they have before even attempting to offer them a solution.

Gary: I always talk, so I’ve never asked questions in my life for permission to talk. I’m going to talk when it’s inappropriate. I’m going to talk over you if I have to. I’m going to talk. I’m always asking questions to reverse-engineer the insight and to provide the most value from that insight.

Steli: I could stay in the topic of selling wine for a long time because I think it’s a fascinating product if you think about it.

Gary: Here’s what’s fascinating about it. People are intimidated by it and it’s all based on stories. It’s all commodity. At some level, a Pinot Noir is a Pinot Noir and is a better Pinot Noir than other Pinot Noirs. There are other better Barolos than other Barolos. But there are very few people who actually can taste the difference. Now you’re in fully story-telling mode and now you’re playing on emotion and the vineyard stories. As an artist – that’s how I think of myself as a salesman – it gave me a big canvas to draw. The only thing I had to navigate through was the ratings by the biggest reviewers – Robert Parker, Wine Spectator – but outside of that context it was free rein.

Steli: I want to come back to the storytelling aspect of sales but before we do that I want to just briefly talk about how you ask questions. You understand the person, then you kind of find a way to story-tell them into finding something that’s a good match that emotionally speaks to them.

Gary: And?

Steli: Yeah?

Gary: Is in the benefit of my business.

Steli: Okay.

Gary: I think the best salesperson provides both. The worst salesman is out for themselves and that’s why we see a lot of bad salespeople. The second worst salesman is one hundred per cent in the camp of the customer and is doing something that’s not benefitting their business.

Steli: Yeah.

Gary: To be the best salesperson is the one that’s providing value to both fronts like I took a lot of pride in efforts long before you sell it starts at product. I had to get great at tasting wine because I wanted to find the best deal on a twelve-dollar wine that I could buy for eight dollars versus the twelve-dollar wine that I bought for eleven dollars.

Steli: Yeah.

Gary: I had to find something esoteric to make that kind of profit so I had to know what it was. If I don’t feel good about what I’m selling, I’m dead.

Steli: Yeah because you’re not authentic. You’re a super passionate guy but what fuels that passion -

Gary: I can be authentic about selling. I’m authentically in love with the sport of selling. I just want to be able to sell to that person again and if I don’t believe in what I’m selling I won’t get that chance.

Steli: Absolutely!

Let’s talk real quick about what happens when challenges arise in the interaction. Let’s say competence on confidence especially the early days but also later on in life. You ask questions, you understand somebody, you offer them a solution, you make your pitch and they have objections or they have fears. How did you react to that debate, but also how do you think about that today when people come up with objections and things that challenge and standing the way between you and closing the deal even if it’s a great deal for both sides? How do you think about that philosophically and also technically?

Gary: I think about it very heavily, actually. This is a great question. I’m very weird on this answer and I know a lot of people are watching so I want to be careful here. I disrespect the customer that doesn’t get what I sell. I become combative and non-pressuring; meaning if you don’t want to buy what I’m selling I become borderline disappointed and condescending. I spend almost no time trying to convince somebody to buy something when they provide resistance after I’ve done my part.

Steli: Was it always like that?

Gary: Yeah.

Steli: How did it work in the early days? You’re a pretty big brand by now at VaynerMedia when clients come...

Gary: Right. It worked awesomely; meaning it didn’t work. They didn’t buy the wine I sold; however, as the wines that I was pushing became the most popular wines in the world. As people saw that I knew what I was talking about, I started getting historical credit. That, my friend, is what I’ve been focused on. When they don’t buy my personality as Gary V, when they don’t buy VaynerMedia, when they don’t buy the wine because I always know I’m going to be right. I always believe in what I’m selling and because I have a good enough track record to be right about what I’ve been selling. As a betting exercise to decide if I think that person is smart; I am so confident and have so much ego and bravado to what I’m selling that if somebody doesn’t buy it, it puts me in a zone of disrespecting their intellect and ability to feel what’s happening in the moment and it changes the course of my perception of them. That may not mean anything to the person but it’s reared its head multiple times in my career where that person on the other side has gone on to other places, has needed my help or services and I have a taste of not getting the sale because I actually like when I don’t get the sale and I can have the empathy to understand why they didn’t buy it, not because they didn’t buy what I was selling but they didn’t buy because they just couldn't. There are some tactical reasons and I understood it. That’s fine.

When they could and they went with something else without thinking about it. This is fun for me, I’m enjoying this interview. It’s an interesting thing. I am flabbergasted if I give my best step back and they can buy but they don’t; it really makes me question and makes me navigate doing business with them in the future because we’ll be doing business with lots of people in the future wearing different hats.

I was just in Dallas this morning – I’m in Orlando now – and ran into somebody at a marketing conference that I did wine business with. I hadn’t seen him in ten years. Some of his smart decision-making is on his family’s winery betting on me when I was a kid nobody knew. It made me believe in his intuition and now that he needs me more in this scenario, I’m going to pay forward to him because I believe in his gut feeling and his intellect and his paying forward and that’s kind of cool to me.

Steli: That kind of competitiveness that you described to some degree, you put your heart and soul into something; you are sure that what you are selling benefits both parties and it’s going to be a big win. And then saying, “I’ve done everything I could to make a good business better. If you don’t take that, that kind of totally takes me by surprise and makes me wonder who I’m dealing with.” I could see people – especially people outside of the sales realm – seeing this as a typical sales guy arrogance kind of approach.

Gary: Yeah. It sounds terrible.

Steli: It does.

Gary: It sounds atrocious. I hate that I’m so authentic in my interviews and always want to tell the truth because that was so uncomfortable to answer. That was one of the douchiest things I’ve said publicly, but it’s the truth.

Steli: But that’s why it’s actually valuable because you could give me an easy answer to make yourself look good and make us roll with the interview nicely, how awesome salespeople are under the hustle. But if you actually said something that’s uncomfortable but true, it lets us explore and go a little bit deeper on the things.

Gary: This interview in itself started with my thesis which is I’m impressed that you have sniffed out that probably the thing that I most am is the least dug into by the entire marketing ecosystem that already makes me want to dig deep. You might have even noticed, you’ve watched a lot of my interviews; I even did a ‘let me look into the sky and really think here’ because I think you deserve it because you set up the context properly.

Steli: Awesome!

Let’s us spend just a little bit more time before we move from this; there are so many things I want to talk about but I don’t want to just leave this off on the wrong foot because I know that certain people, specifically the people that don’t know your work and haven’t studied you for many, many years and missing the context of what’s really valuable here because I think that that competitiveness that you’re describing is maybe something that many hustlers and salespeople really have. But if you don’t have the foundation of actually doing the work and the research and knowing that what you’re proposing is in the best interest of all parties involved and you worked your ass off to create win-wins; if you don’t have that as the foundation, all that’s left is selfishness and then if you run into people five or ten years later they are actually happy they never bought from you and you have to keep on finding new people like you’re running out of people eventually. In that regard, the project you have is like I’m glad when somebody says no because sooner or later time will tell when what I’ve tried to sell is actually a great thing to do so the future will cross paths and create the opportunities.

Gary: Great opportunities because when you’re right, they buy from you more emphatically time number two. I’m very proud that VaynerMedia is now at the stage where people that we’ve done business with have gone into other companies and that more and more of the people we did business with before; that’s how you scale.

Steli: Yeah.

Gary: We’re about to land a multi-million dollar deal from a very big company, completly based on the work we did two years ago; a client that didn’t believe in a lot of stuff we were selling and wanted to go more traditional but got results.

To be able to do build a wine business, I need everybody to buy wine from me. We buy wine twenty-five to fifty times a year. You want to come back; if you don’t do that you start losing. I’ve only been in the mindset of returning customers lifetime value and I’ve always sold something I believe in and I’ve always been a foremost expert in the things that I’ve sold. I have not been average. I have not been average in wine or social media. I’m not an average guy in those things. Once you hit a pedestal, I’m scared to come down from it. I’m incentivized to stay at the top. I don’t want to fall off. I don’t have to be a one-hit-wonder. I’m completely driven by fear, by gratitude, by empathy that I have gifted gifts that I have to execute against, by legacy, by a lot of pure things.

I really, truly believe that a great saleswoman or man is as good as it gets in human behaviour. It blows me away to know that salespeople is a negative condensation in the world and that’s fascinating to me. It’s fascinating to me that the purest five or two or one per cent of salespeople are the singular best people I know and that the other ninety-seven per cent tether towards the worst people I know. It’s why it’s a very interesting game.

Steli: Yeah. Let’s talk about this for a little bit, sales and ethics. Authenticity is one part but knowing why you’re doing what you’re doing, why you’re in sales, why you are in the business of influencing people, basically. You’re leaving the realm of a passive group of people that’s just focused on what they’re doing to a more proactive and influential group of people that go off and try to change people’s minds and make people do things and help people make decisions. I think that might play a big role in people being uncomfortable with salespeople because salespeople literally want to influence other people and some people are afraid of that and many areas incentivized sales in a bad way and got bad behaviour out of that.

Gary: Yeah, that’s right.

Steli: If you give the wrong incentives you get the wrong behaviour.

Gary: Being a great salesperson gets into manipulation and manipulation gets into ‘are you going to do something great with your talents or are you going to do something evil?’ Some of the most evil men and women of all times were inches away from being some of the greatest because they had the power, they just chose to do the wrong thing with it or their DNA was wrong. I am extremely self-aware to how close I am to the dark side. I’m very self-aware of it; I’m so thankful that whatever moral compass was in me and the way my parents parented me. I was close; I’m close I can taste it. You can just taste it, it’s very close. If you’re great at it, you’re very close.

Steli:                      Have you ever crossed that line? Has there ever been a time, and not when you were a little kid and you didn’t know what you were doing?

Gary: I’ve crossed the line in my youth in a lightweight way where I bullshitted and elaborated further than what I think is acceptable by all regular standards. There’s embellishing and hyperbole and then there’s lying. I think that it took me a little while to get the handle bars right. Fifteen, sixteen, seventeen, eighteen, nineteen, twenty I was still finding my way; I would still over-emphasize and even to this day.

What seemed to me as being so public and I’m scared, but even if you look at my key notes, I’d run the gamut. Once and for all, it’s like three point eight when I took over but I say three and sometimes I say four. I don’t always context how I grew the business. Sometimes I say forty-five, sometimes I say sixty because in my mind I’m talking about different periods. Once one period that I really ran it at the library. I’m not one that worries about black and white but I’m scared to be called out so I stay in my zone these days. I stay in my zone.

Steli: Awesome! Let’s step back from kind of sales philosophy and ethics and shift to a bit more tactical stuff. We started off with you selling lemonade and baseball cards or football cards and then wine.

Let’s jump to today and being in media. I know that’s kind of your focus on the execution part of you. rowing that business dramatically and sell to large organizations, not the individual consumer walking into a wine cellar to buy.

Gary:I went right from B to C.

Steli: Exactly! What has changed? I know that some things are the same. You try to create win-wins and you being authentic. But what has changed? What’s different when you try to land a massive Fortune 500 company and you give them your pitch? How do you think about selling to these organizations? What structures, what tactics, tool and tips do you have and how do you approach that sale?

Gary: Nothing has changed other than me having to learn what they care about.

Steli: What do they care about?

Gary:Lots of different things – to get press so that they can get a raise or get taken away from that company and taken to another company. They think that’s their best way to succeed; to not work hard because they just have two kids and they want to have better work-life balance so you have to deliver.

I am objective of the other person agnostic.

Steli: Okay.

Gary: I could care less. I just want to figure it out and as soon as I know it, I will sell them that as long as I feel good about what we’re doing. We’ll do a lot of grunt work for you because you don’t want to do it because you’re busy. We’ll get you in the press and get your brand a ton of press. We’ll pump you up internally to your bosses as long as you’re doing the good work that your brand actually needs.

I don’t mind what the spark and the sizzle is but if the stake is flawed, I’m out.

Steli: You’re touching on something that’s really important and powerful when it comes to selling to organizations. A lot of entrepreneurs come to me and when they describe how they’re trying to sell to an organization, they always do it as if the organization is not a collection of individuals. They always think it’s in the best interest of company X, Y, Z to do this but the people – the decision makers, the stakeholders – they might have aligned interests, but sometimes they don’t.

Gary: They mostly don’t.

Steli: They don’t, yeah. You talked about people’s selfish interests like being promoted, getting a new job, working very little.

Gary: Every single person has to be selfish to some degree; it’s human behaviour. None of us are flawed; none of us. This is normal. Some could go to an extreme and it’s all calibration. If you go too extreme that you care about just yourself, you’re starting to get into a place. But I default into those flaws; I think about them and the reason I can sleep at night is I use them not as the only thing we do but as a permission to do the best.

The truth is what I sell and I’ve always sold in my entire life, is the future. When you’re selling the future, it’s hard to sell in the present. You have to sell in what people care about in the present to basically trick them to getting to the future.

Steli: That’s awesome! I can see how that applies to everything that I know you’re selling – from wine to books.

Gary: To my employees or my vision.

Steli: Yeah.

Gary: I’m fine with using the word ‘trick’ because it makes me laugh because it’s funny to me. But it’s not a trick, it’s getting them to see possibilities that others don’t see at that moment but I never sell something that’s not practical. I’m not selling augmented reality right now. I’m not selling SnapChat to sixteen-year-old audiences right now. We may. I always feel like I’m very practical.

I’m a Russian immigrant. It has to make sense but I don’t mind investing in twelve to eighteen months out. I’m selling individually. You’re showing me a forty-billion-dollar company I’m working with, I see Karen and her decisions to make. I need to figure Karen out because she’s going to make the decisions.

Steli: Yes. I love that. That’s an insight a lot of people are missing because a lot of people are so...

Gary: Because of a couple of things. One, they’re not good salespeople. Two, they’re romantic. The reason people are bad at sales is they’re romantic. They think that their solution is so great for Pepsi that of course it has to happen. That is a naivety that has put a lot of businesses directly into the ground.

Steli: It sounds very much like we’re talking even more specifically about tech entrepreneurs, right?

Gary: Yeah. Shopping cart innovations and retailer innovations. Yes, we come from that world but it happens in every world. The two people that lose are the romantics and the ones that think they can sleaze their way through. The two people that lose are the ones that are romantic and are not practical and the ones that think they got so much charisma and charm and so much bullshit that nobody will call their bluff and it’s worked for them. What they don’t realize is they’re climbing up the same hill over and over. You’re right, you can do it and you can have a lot of one-night stands but to have a meaningful marriage, you’d lose.

Steli: Let’s talk about people trying to sell to you. You’re an investor. You’ve just raised funding so now there’s more capital to allocate and support entrepreneurs. When you look at entrepreneurs, first of all, being a hustler, is that something you appreciate or is that kind of a requirement for you to invest? Or is every company different?

Gary: Both; it’s a requirement and I appreciate it.

Steli: Would you invest in a very technical company if you find the people brilliant but maybe not having the core hustler DNA?

Gary: No.

Steli: Why?

Gary: Because I’m uncomfortable in that environment. Because I do not believe that that puts me in the best position to succeed. I believe that business is war and I’m looking for wartime generals. She or he better know what to do when their tech gets copied. Now what?

Steli: How do you know somebody is a hustler?

Gary: I guess.

Steli: What are the signals that help you in that guesswork? What are you even looking for?

Gary: Luckily for me this is so not replicable. Luckily for me, I feel that I have EQ. As you know by us rescheduling this multiple times, by the email I send a couple of hours ago, I was looking to be off this interview five minutes ago. One hundred per cent needed to be off five minutes ago; I got something going on. But because I feel like you’re an awesome dude and I’m reacting to the questions and the vibe and the way you handle the whole process, here I am.

It’s just like this interview. I just go on the way I feel. It’s been great in picking my wife. It’s been great in picking a lot of investments and it’s been wrong in picking investments because I become impatient at times because it’s hard to find them. My discipline is probably a factor because sometimes you’re wrong. And because sometimes the hustle is a very thin line. I’ve got one investment I could think of right now where it could have been a billion-dollar play and it became a crash-and-burn within a year and it had to do with that magic. I’d probably bet on that person again, believe it or not, because it’s so close. Do you know what I mean?

Steli: Yeah.

Gary: After the second time, I’d probably give up but I would play again.

The truth is, it’s very personal. I don’t think I’m great at it; I think I’m normal at it, it’s what I think.

Steli: Awesome! Hey, I want to be respectful of your time.

Gary: Let’s keep going. Keep going; I’ll tell you when to stop.

Steli: Okay, awesome! I know a lot of times you’ve talked about kind of hustle being in your DNA. Would you say that hustling or sales in general is uncoachable? Do you think you can learn to sell or learn to be sell or learn to be more of a hustler or do you think you just have it in your blood?

Gary: I think I can learn to become a dramatically better version of a basketball player than I am right now; I do not think that I can learn how to be in the NBA.

Steli: Okay.

Gary: I think everybody has upside, right? I think you can teach a lot of things but it does have a limit.

Steli: When you are hiring people for your businesses or even when you make investments, is there some kind of framework that you think about where you see somebody that has the potential to be an amazing hustler or salesperson that you’re coaching them in or is it all just kind of gut-feel or intuition? Do you just – for situation to situation – just jump in and tell them, give them an outsider perspective and things that you have to do?

Gary: Raw talent – if you see things in people; I do bring them into Ninja Forces to work on something so I can see. If I see something in an email, in a presentation, in the way they interact with somebody in the hall, I will take note and then I will bring them into an inner circle of something so I can dig a little deeper. If that goes well, I’ll dig a little deeper. There have been ways of that, for sure. I think that’s what’s being a scalable operator to the level that I am; I think it’s one of my best skills. I actually build businesses. It’s not just being the social media guru or me being the wine guy and I have a wine show. I have organizations – hefty, eight-figure organizations – that I built in thirty-six to forty-eight months both times. That takes talent and that talent is actually HR people talent; it’s not other talent. I have an act and listen, boy, do I miss a bunch of times too. But when you’re hitting one out of every two times, that’s an incredible percentage.

Steli: Yeah.

Gary: When you’re finding talents that sticks with you and that you groomed -

Steli: Magic happens and you’re able to actually grow things. You can't grow tons of businesses on your own especially when you schedule all the interviews, the books and things.

Gary: I’ve met Brandon Warnecke my first day of ninth grade. He was a nerd in high school; I was an upper popular kid. I kept that relationship at fifteen, sixteen, seventeen when girls told me not even to be friends with him because it was bad for my rep. Not fully, Brandon, don’t worry, but kind of. He runs wine library and I sniffed out his talent at fourteen. I believe in it. Awesome!

Steli: When people try to pitch you on their ideas, I’m sure hundreds and thousands that reach out to you with cold emails or in events, I’m sure there are people that shake your hands and try to give you an elevator pitch; give these people some feedback, some do’s and don’ts or sins. Don’t waste your time to come and do X or here’s a pitch, here’s an email that was really effective and really came through through all the noise.

Gary: If someone is trying to game me which would make sense as I would do if I wanted to get to somebody, you’re not going to trick me on my move. Now with Jab Jab Jab Right Hook, everyone is sending me emails trying to jab me. I literally read them like 'Okay, I’ll see you in a couple of minutes.' Sure enough, another one. And then I’m like, okay, there it is, the pitch! Authentically jab me; actually try to bring me value, not just saying hello for the sake of it.

Have you ever seen somebody fake-smile?

Steli: Yeah, all the time.

Gary: I just can’t deal with that. I don’t mind if you come in right for the kill on the right hook if I feel like you authentically have some magic, and you feel it, and I believe you that you believe you have it. I’m okay if you jab me, if you authentically jab me; you’re literally thinking ‘I don’t have anything for him but he’s a guy and I’m just going to keep providing value and maybe six years from now...’ I just need to believe the authenticity. There’s no real tactic, it’s just my radar, one that I think is in tune so I don’t get tricked easily. I have family members that do, and I watch it and I know. That’s it.

Steli: What about follow up? Where does persistence start and end and where is it desperate?

Gary: I over-index on liking people stalking. I give the benefit of the doubt where most people think things get annoying, I see perseverance, I do. Eventually, I go into annoyed states when I clearly articulated I’m not interested. But when I haven’t responded or I was wishy-washy because I was being polite, I don’t mind perseverance.

Steli: You respect that?

Gary: I do. That’s because I know that I haven’t given a clear no.

Steli: Yeah.

Gary: It’s like, “Yo man, I’m head down for three months” because sometimes I am head down, but I don’t want to say no because I wonder if it’s got something or where I don’t answer because I just missed it on email. I don’t answer on email anymore; I’m trying but it’s just overwhelming. But if I say I’m really not interested, I can’t do it, and then there’s persistence, I don’t mind one more because I like the fight. But two more would start getting me into a weirder place.

Steli: I get it. What are your favourite entrepreneurs especially when it comes to the hustle? Are there any people that are like, the best hustlers in the game today? You’re a sports guy, who are the ultimate hustlers in the world right now from your perspective; people that are on your radar, that inspire you.

Gary: I think Mark Zuckerberg is crazy underrated; underrated.

Steli: Underrated?

Gary: He’s a massive hustler. I love his tenacity at paying attention to everything going on to make sure that Facebook’s throne doesn’t get touched or copied. I’m obsessed with his tenacity, hustle skills; I think they’re grossly, grossly, grossly underestimated. I think people think of him more as a Bill Gates, as a nerd, as a dev, I don’t see that at all. I think Travis Kalanick of Uber is an outrageous hustler. I’m a huge fan; he’s got straight fire. I believe in him quite a bit. I’ve known him for a long time as a friend and I’m an investor in Uber though I solely passed in the beginning, a mistake on my part and I should have not made the suggestion ##### on Travis though I didn’t think he was going to be that involved which is why. I think I’m a huge fan of Katya and Haley, the Birchbox co-founders. They are hardcore. They are relentless; they’re out there pounding. They had to hustle both to breakthrough in the cosmetics world to break though a new business model which is sampling of the month club to break through in the VC world. I find Katya and Haley have that quiet fire, graceful fire. They definitely, definitely, definitely have it.

Steli: Awesome! The Birchbox founders and Travis I think, it’s easy for everybody to see why you put them as core hustler geniuses up there. Mark Zuckerberg is an awesome one because it’s kind of left field. As you said, people don’t see it that way.

Gary: People are really sleeping on him. He’s an assassin that way. Listen to the reason he’s so successful. He’s got a lot of good things going for him. A lot of times guys like me, for example, at times are like, “Hey, go there” and I’ll just literally run through the glass where the door was right there and I could have just opened it. He’s really strong at both of those things.

Steli: Yeah.

Gary: I’m proud that I opened the door seven out of ten times but I’ll run right through the goddamn glass three out of ten times. It’s just the way it is.

Steli: With the eyes through the door rather than with the head through the wall.

Gary: Absolutely.

Steli: Two last questions and I’ll let you go. I want you to remember, if you can, two scenarios and share them with us. One is kind of your biggest sales victories – a huge deal that you got either for VaynerMedia or for your wine library.

Gary: I got it. Ready?

Steli: And the biggest failure; one of the most devastating pitches that you lost or even moments where you try to convince someone.

Gary: Yeah. I couldn't convince Ben Silverman over email to let me invest in Pinterest a couple of years ago. That’s a big loss for me financially and I’m disappointed that I didn’t run through the glass. I should have gotten on the plane and I would have gotten it. I would have got it; I just didn’t want it bad enough.

And as far as the win, the first two clients of VaynerMedia were the Jets and the Nets. Both Brett Yormark – the CEO of the Nets – and Matt Higgins – the President of the Jets ### – who is now my partner in Vayner LLC; both came to me to sell me sky boxes at the Nets and the Jets stadium at WineLibrary. They didn’t know VaynerMedia was coming because I hadn’t started it. AJ was just about to graduate. They walked in with a sales pitch deck to sell WineLibrary sky boxes at their stadiums and they left within the hour - both big time salespeople - as VaynerMedia clients. I literally switched and sold them in the meeting. And to this day both of them knew and they have massively fond memories of ‘holy crap!’ Brett Yormark especially wrote me an incredible email. He’s a true hustling salesman and he was flabbergasted that I was able to flip the switch on him, and get him to be a client.

Steli: That’s awesome! Thank you so much for sharing those stories!

Gary: My pleasure.

Steli: Gary, thanks so much for taking the time. You’re awesome! Keep hustling! Keep inspiring all of us. I look forward to meeting you and seeing you soon!

Gary: I can’t wait! Take care, everyone! Bye!

Steli: Bye!

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