Back in 2006, Gary Vaynerchuk started a daily video show that turned wine criticism on its head. More importantly, it took his family wine business from $3 million-a-year to a $60 million-a-year ecommerce juggernaut.
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From there, Gary did something that surprised a lot of people, including me. He started a digital marketing agency called VaynerMedia.
Wait … what? Why would someone who could move that level of product want to build a service business? Isn’t that going backwards?
Not so fast. As you’ll hear in this candid interview, Gary’s plan involves what has now become familiar to Unemployable listeners – doing this thing now in order to set the stage for bigger and better things down the road.
In other words, true entrepreneurs are always playing the long game. Listen in for amazing insights from one of the most outspoken advocates for the unemployable.
Listen to Unemployable: Advice for Freelancers and Entrepreneurs below ...
The Show Notes
Gary Vaynerchuk on Playing the Long Game
Gary Vaynerchuk: Hey, guys, I’m Gary Vaynerchuk. I’m a purebred entrepreneur, and I’m really unemployable.
Voiceover: Welcome to Unemployable, the show for people who can get a job, they’re just not inclined to take one — and that’s putting it gently. In addition to this podcast, thousands of freelancers and entrepreneurs get actionable advice and other valuable resources from the weekly Unemployable email newsletter. Join us by registering for our free Profit Pillars course, or choose to sign up for the newsletter only at no charge. Simply head over to Unemployable.com and take your business and lifestyle to the next level. That’s Unemployable.com.
Brian Clark: Back in 2006, Gary Vaynerchuk started a daily video show that turned wine criticism on its head. More importantly, it took his family wine business from $3 million a year to a $60-million-a-year e-commerce juggernaut. From there, Gary did something that surprised a lot of people, including me — he started a digital marketing agency called VaynerMedia. Wait, what? Why would someone who could move that level of product want to build a service business? Isn’t that going backwards?
Not so fast. As you’ll hear in this candid interview, Gary’s plan involves what has now become familiar to Unemployable listeners, doing this thing now in order to set the stage for bigger and better things down the road. In other words, true entrepreneurs are always playing the long game. Listen in for amazing insights from one of the most outspoken advocates for the unemployable. I’m Brian Clark, and this is Unemployable.
I’ve got to say, this is a killer interview, if I do say so myself. Let’s dive right in. Gary, my man, how are you?
Gary Vaynerchuk: I’m super well, Brian. Thanks for having me on.
Brian Clark: Oh, no problem at all. Thanks for being here. I’ve got a few things. I want to take you back to the early days of Wine Library TV, but first I’ve got to talk about these videos you’ve been doing lately. You are on fire — calling out the complainers, giving a message to recent college grads. The interesting thing to me is VaynerMedia has a lot of blue-chip clients, big clients, people with a lot of money, but you’re passionately speaking to the entrepreneurs. What’s driving you on this?
Gary Vaynerchuk: Well, thank you for noticing. There’s several different things that are happening here, and I’ll break them down for the audience. One: I’m always going to be an entrepreneur. Brian, you’re one of the few people — there’s a couple hundred, maybe a couple thousand out there — we’ve been in this from the beginning. We’ve known each other when all this started popping up.
Brian Clark: Ten years, yep.
Who is Gary Vee?
Gary Vaynerchuk: Yeah, that’s exactly right. It’s kind of crazy. I think you were quite established — I was in e-commerce in the wine business in the late ’90s. I didn’t really hit the internet, the marketing, the web 2.0 world until really about 2006-7. For a lot of people that were out there, branded, and well known — you being one of them — a lot of you grew up in the web 1.0 world together. Early bloggers and things of that nature. I came on the scene and I don’t think they really knew if I was a flash in the pan. Would I be around in a day or two, or this, that, and the other thing?
I haven’t changed from the guy that hit the scene a decade ago. Things around me have changed. I’ve changed — your life evolves — but I’m enormously passionate about entrepreneurship and about people realizing that this Internet thing is big and a lot of good can come from it. I am more intoxicated personally when I get an email from somebody that says, “I’ve made a …” For example, I had an eBay store rant on Snapchat and I’ve gotten 10, 20 emails this week, “Hey, instead of sitting on my ass this weekend I made $187 going to garage sales and selling on eBay. Oh, by the way, I have $80 in my bank account. This was meaningful. You’ve helped me.”
Helping the individual entrepreneur– even though I have a 650-person agency that has $100 million in revenue and works with the biggest brands in the world — it’s just … Even when I buy the New York Jets as the owner of an NFL team in my 70s, I have a funny feeling I’m going to be making virtual-reality videos ranting to 15-year-olds that they can do it. Or there’s this opportunity, or that, or the other thing.
Brian Clark: I love it. Yeah. What strikes me especially is — at least I think it resonates with me — I’m tired of the dreamers, I only want to talk to the doers. That’s why the focus of this show is really on the people that are already out there. You took the plunge and now you’re either treading water or you’re swimming for the shore, whatever the case may be. But when you call people out and say, “Why are you looking for the shortcut? It’s a process. It’s a long game,” that’s the truth. We have this cult of entrepreneurism now. They’re interested in being called an entrepreneur, as opposed to perhaps truly being one.
Gary Vaynerchuk: You’re preaching. I can call myself an athlete, but I’m not a professional athlete. I think you can call yourself an entrepreneur, but are you self-sustaining? Will you be around in three years? As I’m listening to you, clearly we’re resonating on a similar topic right now, which is we’re living through the greatest era of fake entrepreneurship ever. These are people that actually won’t be in the game in three or four years. They’ll be working at companies. That’s like 60 percent of entrepreneurship out there right now.
Then you’ve got another 30 percent of people that are selling to those people, and it’s all programs and propaganda — taking money out of a bank account and putting it on a bed and taking a picture and putting it on Instagram. I truly believe that out of the 100 percent of people rolling as entrepreneurs, only 10 percent of them are what I consider an entrepreneur, which is somebody who’s self-sustaining, doing it the right and noble way, and will be around in 20 and 30 years and be respected and be proud of how they made their money.
This is probably why you and I have a kinship from afar and ping each other on Twitter and say, “Hey, hope you’re doing well,” or Retweet each other. There’s this kind of … It’s almost like a head nod. You and I have not had the luxury over this last decade of spending that much time together, but when I think of your name and what you’ve done, and how long you’ve been around in the right way and how people think of you — it’s like that fun thing. I feel like if I saw you at a conference, running through an airport, or even digitally — it’s that head nod. It’s that wink. It’s that acknowledgement.
I think over time that stuff weeds itself out. I understand why my personality and the way I present and the way that I curse may make it look like I’m part of that 30 percent, but I’m excited that now my body of work is starting to establish itself above and beyond my showmanship when the camera is on.
Brian Clark: Yeah, absolutely. Let me run something by you here, because I think the misconception out there among the complainers, dreamers, whatever you want to call them, is that there’s a destination — that you arrive at some point. They’re trying to get there as fast as possible, but there is no destination. Like you said in one of your recent videos, it’s a process. This is my drug. This is my air. If you don’t live for that I don’t see it happening. Let me run this by you. This theme keeps coming up, guest after guest. Anyone who works for themselves in whatever capacity, freelancer to CEO — it’s something I call the perpetual side hustle. What you’re doing now pays the bills so you can do the next thing. Do you view things that way?
Gary Vaynerchuk: Yeah. Here’s how I view it. Brian, can you even imagine not doing what you’re doing?
Brian Clark: Not at all.
Gary Vaynerchuk: That’s it, guys. This one second of this clip, that’s the show. I don’t even think about anything else. I don’t even know anything else. It’s literally like breathing. That’s why I say it. My literal hobby when I had a minute pre-kids was to go garage sailing, buy stuff, and sell it on eBay.
Brian Clark: Now, that’s a true hustle.
Gary Vaynerchuk: That’s it. I don’t even know. My entire life revolves around market behaviors: buying and selling, looking for the white space, how do people think, communications, messaging. I don’t think any true-bred anything does it because they think it’s the thing they want to do of the moment, meaning, I don’t think a true-bred artist had any options. I don’t think they woke up in sixth grade and said, “Oh, rock stars get chicks. I’m going to become a rock star.” I don’t think that that’s the way it works.
I think the top 1 percent — the winners, the people that actually accomplish their goals within their task at hand — have no other gear. I don’t think Kobe could have been anything else. I think there’s a disrespect for entrepreneurship right now that anybody can do it. Of course anybody can do it, because right now — because of the Internet especially, and because it takes no money to put entrepreneur on your business card — if you have an idea, you’re an entrepreneur.
Brian Clark: Yeah.
Gary Vaynerchuk: But that’s literally like saying, “I’m a singer.” There isn’t a definition of professional entrepreneur versus entrepreneur. I think we need to start having that conversation, because I just don’t know any other option.
How Gary Vee Found His Voice
Brian Clark: Yeah. All right, let’s shift gears a little bit here. I use your Wine Library show that’s now retired as a prime example of content marketing done well. I used to give examples of how Proctor and Gamble invented the soap opera, and then I come full circle to Gary Vee and the Wine Library show as, “Hey, this is a guy in the office above the wine store with a camera and he went from $3 million to $60 million in sales.” But here’s what I want to bring people back to — I had actually forgotten myself, because Copyblogger launched in 2006 — Wine Library TV launched in 2006, if I remember correctly.
Gary Vaynerchuk: That’s right.
Brian Clark: Everyone looks at Gary Vee the showman, as you said, and they’re like, “I can’t be that guy,” but people don’t realize that it took you many episodes of that show to find your voice, to find your thing. When you finally became yourself, I think, is when it took off.
Gary Vaynerchuk: Yeah.
Brian Clark: Talk about that a little bit.
Gary Vaynerchuk: The first 80 — I can’t remember the exact number, so I’ll go with 80 episodes … Don’t forget, I started that show. I was the operator of a business where most of my day, 6 to 7 hours a day, was spent being on the phone or email with high net-worth individuals buying expensive wine. The thought of being on camera and them seeing me being me — which everybody who’s listening now that knows me knows is not the most consumable for the most conservative — was scary. So there was a reserved version of myself for the first 80 episodes, because I didn’t want to piss off my clientele.
Then around episode 80, I was like, “Wait a minute. This is way bigger than my clientele. If this is going so well with me being 70 percent me, what would happen if I was just me? Yes, some people would be upset, but I have a funny feeling this is going to work.” It just felt right to me. I felt like I was there. Like everything in my life and everybody’s life, when you’re the most yourself — good, bad, or indifferent — the things that are supposed to happen are going to happen. That’s what I allowed myself to happen, and that has been the beginning of that process that has allowed me to really become who I am.
Brian Clark: Was it a certain day that you decided, “Screw it. I’m going to be me,” or was it a gradual process?
Gary Vaynerchuk: No, it was an intuition. There was actually a moment in time where I was negotiating a television deal and I didn’t do a bunch of episodes. There was a whole summer almost. I’ve got to go look at the dates, but I remember at least three to five weeks where I didn’t do it, which was big because the audience had started forming. Just during that time when I was negotiating. They were like, “Well, you’ve got to do this and this,” and I’m like, “Wait a minute. It’s a lot of fake stuff.”
I intuitively understood that authenticity would probably become a buzzword, and the summer of ’06 I definitely was like, “Wait a minute.” Then I was just realizing that this web 2.0 thing is happening. It just felt right. When I came back, I was just me. There was a little month period there in the summer of ’06 where I took a little bit of a hiatus in episodes — because I was banging them out five days a week and did pretty much for five years.
Nobody was more consistent in long-form video blogging than me at that point because I was doing it daily. Diggnation and Rocketboom and other people were doing it weekly. I was cranking it, putting in the work. For everybody listening, anything that holds you back from your real intentions and your real form is a vulnerability. You’re not helping yourself. You’re maybe solving for some short-term upside, but you’re hurting yourself for the long-term upside.
Brian Clark: The interesting thing here is the reason why it exploded when you became you is because you were everything wine criticism is not supposed to be, which is another way of saying everything that normal people hate about wine criticism. You said, “No, drink what you like. Here.” It’s brilliant when you think about it in retrospect. But for you, you were like, “This may not work but let’s give it a shot.”
Gary Vaynerchuk: I just was scared to lie. I was scared to lie about my reviews, so that meant I panned a lot of things. Very honestly, I wish I was doing videos back then so I can’t just Monday-morning quarterback this. I knew it was going to work because I knew people were tired of the wine world of everybody talking down to people. Normal dudes, normal people just didn’t want to hear the snobbery. Listen, I was in the store every Saturday with 2,000 people. I knew that they responded better to real talk than me douche-bagging them up.
Why He Started His Own Agency
Brian Clark: Yeah. Okay, let me ask you this. A lot of people who listen to this show have gotten their start by either freelancing, consulting, or serving clients. My first three businesses were service businesses. In 2005, I said, “Never again. I’m going to products.” That’s worked out really well for us. You started out selling wine and decided to start an agency. Take us behind your reasoning here.
Gary Vaynerchuk: This is something I haven’t said super publicly, but I’ll share it with you because I want to give you an exclusive. I built this company for myself, meaning we’re doing client services, but this machine is going to serve everything I do in the future. I’m going to buy businesses and brands in the future and act more like a private-equity firm. I’m going to make bigger investments in venture capital where I don’t own 1 percent of the company or a quarter of a point, I’ll own 17, 19, 39, 51. And I will deploy the VaynerMedia machine against all of it.
Seven years ago, I decided I needed to build the scalable version of myself. So let me build the company that is me, and let me eat sh*t for a decade. By the way, remember when I started this company, I was very much me. I had a lot of leverage. I made a lot of good investments. I had a lot of leverage. Going into client services was a real “what the hell” from a lot of my friends. But I’m stunningly patient. I’m way more patient than people realize.
I literally, at 30, said, “I’m going to punt the next 10 years of my happiness.” Because client services suck. We all know it. Everybody listening knows it. But it’s okay, I’m going to learn a lot. I’m going to learn how Fortune 100 companies work. I’m going to give them amazing services. We’re going to be better than anybody else because we really know what we’re doing. That’s what we did, man.
Brian Clark: That’s fascinating, because you just explained better than I did what I was talking about earlier. People are like, “Oh, you start an agency so you can make money, and this, and that, and the other.” No! There’s a much longer play here. The agency is the beginning of the other things that you’re aiming for.
Gary Vaynerchuk: When you have talent — can you imagine? I’m listening to myself right now, and I’m like, “Wow!” When I’m pooh-poohing … I’m literally going to build a $500-million-a-year-revenue business that is a proxy to something else that I want to get accomplished. That is insane.
Brian Clark: That’s it, yes.
His Long-Term Outlook
Gary Vaynerchuk: And I’m going to pull it off. It’s a foregone conclusion. I mean, I could die and then not, but … That’s a big deal. Listen, Brian, there’s another thing. What is going to be known in 30 years that isn’t known today — and is starting to be sniffed out a little bit because we’re a decade in — is I’m trying to be all-time. I’m trying to be all-time. If I actually buy the New York Jets, Brian, let’s play this out. If I actually, from where I started, go on to buy a $4-billion sports organization and I documented the entire journey …
My words are motivating and I’m good at that, but the reason I do DailyVee and the reason I’m documenting so much, is if I can put out a body of work 40 years from now that showed the process of a young man that put in the work, had the vision, and did it the right way. Tried to help people along the way because he was trying to build the biggest building in town by building it, not by tearing everybody else’s buildings down. And then I actually accomplish it. Well, that becomes a real great American dream story. That becomes a movie. That becomes legacy. That becomes all-time special.
I’m not going to become a billionaire overnight like Zucks or like Sacca or like Travis, but I’m going to get there as a tortoise. Which is going to confuse everybody because I have a hare’s costume. I seem like exactly the guy that’s going to burn out in a year or that is full of sh*t, but I’m really excited about my “aha” at 78. I told you. You doubted me, but I stuck it to you. Because I did it the right way and the noble way.
You know what I’m very proud of, Brian? We run in similar circles but haven’t hung out that much. I know when my name gets brought up at any event you’re at, at any dinner, that the people that are saying not nice things about me, “Oh, he’s got a big ego. He thinks this,” they’re the people that don’t know me. The people that are saying nice things are the ones that have spent time with me or have interacted … I have very few detractors that have ever really spent any time with me.
Brian Clark: Yeah. You’re just ambitious and I think that freaks some people out. “How dare he think he’s going to buy the Jets.” But I have no doubts. I don’t know what your timeline is, but you just gave me a clue.
Gary Vaynerchuk: Yeah, it’s long-term, man. I’m super pumped. Honestly, back to being addicted to the process, I secretly think I sabotage myself. Deep down, if you really want me to open up here a little bit, I actually think I could probably get there sooner, but I want to string it out. I love the foreplay of business.
Brian Clark: I love that. I’m stealing that.
Gary Vaynerchuk: I think I’m going to get there. For some weird reason this is my own romance. Maybe this is a flaw, but it’s mine and I love it. And I’m enjoying it. I weirdly think I’d be happier buying the Jets at 70 than 55. I don’t know how to fully synthesize that for everybody, but I just really love the climb. I love the climb. I do. I like the red eye I took last night, secretly.
Listen, I’m taking care of my health and I’m cutting out a lot of time for my family, because I don’t want to have the casualties that come along with the love of the climb. I don’t want to die young from bad health. I don’t want to lose my family from being too much of a workaholic. I’m aware of the casualties. But I would suffocate if I couldn’t play this game the way I want to play.
Brian Clark: Well said. All right, so I went to Twitter and solicited some questions in real time here. Are you ready for a Twitter question?
Gary Vaynerchuk: Yes.
His Biggest Failure in The Last 30 Days
Brian Clark: Darrell Vesterfelt says, “What was your biggest failure in the last 30 days and how did you respond to it?”
Gary Vaynerchuk: Biggest failure? That’s a great question. Last 30 days, biggest failure. We lost a business pitch. The answer is, knock on wood, it’s been a good 30 days. But I’m trying to give something to the audience, and I think people will enjoy it. We lost a business pitch that I was involved with, which is rare. We lose pitches when I’m not in, but I’m such a good closer — I micro-managed it, and boy, do we usually win those — and we lost it.
My response was motivation. I was angry. I got competitive. I’m baffled. I did the blind competitive thing of like, “Wow, those potential clients are really stupid,” which I truly still believe. But I used it as massive motivation. I crushed the next one, and we landed potentially our biggest client two weeks later. It’s not a major failure. I think failures are losing good people at Vayner. Luckily that hasn’t happened recently. Or doing something wrong in my family.
So nothing too major, but on a micro level. What would be considered major by a lot of people. I spent a lot of time and energy on a pitch and we lost it. I still don’t understand why. I blame the judge and the jury, but I’m pumped. I just don’t have dwelling in my vocabulary. It’s amazing how much I love to lose a pick-up basketball game when we’re playing more games, because I come out with so much fire the next time. I used it as motivation. I truly believe a great entrepreneur likes to lose, because I think it motivates her or him. And that’s what I did with it.
Brian Clark: You’re clearly the face of the company, and you clearly are awesome at getting in a boardroom and closing the deal. Do you work directly with clients after that, though?
Gary Vaynerchuk: No, very infrequently. And no client is confused by that.
Brian Clark: How do you pull that off? Every once in a while I’ll get the urge to be David Ogilvy and think of starting an agency, then I’m like, “No, no, no. There’s no way I could do that personally.” But I wouldn’t mind being the guy who brings in the business.
Gary Vaynerchuk: Yeah. By making it very clear that there’s no way in hell that I could do that. Of course, I’m in the backbone business, and so I do work with clients day in and day out from a backbone standpoint, but I’m not on any accounts. There is no account that can pay enough for me to be the strategist on the account.
Brian Clark: Yeah, that makes a lot of sense to me. I was curious about that.
Gary Vaynerchuk: The reason we’ve grown so fast is I’ve never bullsh*t anybody about that. There’s never been a “pull the rug from underneath them” after “Yeah, I’ll be there every day.” I would never. As a matter of fact, I go the other way. My involvement in accounts has been viewed as a major benefit by my clients because they’re promised none of it.
Brian Clark: Yeah, so it’s under-promise and then show up.
Gary Vaynerchuk: Yeah, that’s right.
His Near-Term Outlook
Brian Clark: Okay, you’ve given us the long view, and it’s amazing. What’s near-term? What’s the rest of 2016 for VaynerMedia and/or you personally?
Gary Vaynerchuk: A couple of things. Heavy investment in short-form video. You are really on it, Brian. I think I’ve got an unbelievable advantage, which is I pop on video. Video is exploding in a Facebook and Snapchat and Instagram environment, so I’m quadrupling down on that level. London is massively important for VaynerMedia. We just opened it and we’re going to triple down on that. We’re moving into our new building in New York and I want to make sure that goes well.
Some of you might have heard that my brother AJ left the company because he has Crohn’s disease, so that’s probably at the top of my list — making sure everybody feels supported without AJ being here. I would say 100 people here have unbelievable deep relationships with him, and I want to make sure that they feel supported and nothing was lost in translation now that he’s not here every day.
The video and media-buying capabilities of the agency. I’m closing a major fund. The continuation of my investment. So I’m busy. Then, on the real-life stuff, having a summer where I really spend a lot of time with my kids. I’ve mapped out very cleverly with the way I’m going to do meetings in the Hamptons this summer. I’m trying to be a renaissance man in a 2017 way. The effort and intent is there, and hopefully my actions follow that intent.
Brian Clark: Yeah, best wishes to AJ. I haven’t seen him in a while, but he was the nicest guy.
Gary Vaynerchuk: He is.
Brian Clark: You can only imagine that everyone there is going to miss him.
Gary Vaynerchuk: Of course. He’s like the greatest human being. I miss him every second.
Brian Clark: Awesome. Gary, I’m going to let you go. This has almost been mind-boggling. I wanted you to talk about the long game, so I’m glad you kind of took the lid off of stuff you don’t really talk about. You watch from the outside and you’re like, “He’s up to something big.”
Gary Vaynerchuk: Listen, Brian, it comes out of unbelievable respect for you. This is so easy for me because I read every social-media mention. When your name gets brought up by people in my Twitter feed, the level of respect I have for that individual is often quite high. It’s not only my respect for you that allowed me to get a little bit deeper, but it’s my respect for what I know has to be the audience of this. Let me tell you something about me and you that I know — this is something I know. It takes a certain kind of person to follow us.
Let me explain. You and I are different, we have different ways to communicate. But you and I are selling the same thing, which is the truth, work ethic, long game, quality — all the real things. It’s a lot easier for a lot of people that are listening to this show or watch my stuff to follow a lot of the 100 other characters that may look like us if you don’t look carefully, that are selling quick, fast, easy, money-tomorrow systems. I have enormous amounts of respect for you selling the truth, and that is why I’m very thankful for being on here.
Brian Clark: I appreciate it, man. All right, thanks so much for your time. Take care, buddy.
Gary Vaynerchuk: You’re welcome. Bye-bye.
Brian Clark: Wow! You would think after all these years I’d be immune to that kind of thing, but nope, I get as fired up as anyone else. I hope you’re fired up as well, but let’s do something about this. Let’s not be motivated just for the sake of it. What’s your long game? There’s no destination, but what position do you want to see yourself in down the road? What’s it going to take to get there? Step by step. Map it out. Do a little bit each day. And most importantly, keep going.