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8 Questions With Entrepreneur Gary Vaynerchuk

By Ryan Boog

Happy Dog had the incredible opportunity to spend 15 minutes on the phone with Gary Vaynerchuk as part of his "#1aDayQ&A." We caught him on a Thursday afternoon after he'd just returned home to New Jersey from France, and enjoyed an awesome conversation.

Gary didn't disappoint us; he delivered insightful, energetic insights on everything from the long-term value of SEO to the incredible potential of social media to how to keep going hard and fast after your dreams - but when to slow down, too. We captured the interview on audio, so take a listen! If you're more of a "read it on the page" person, check out the full transcription below!

8 Questions With Entrepreneur Gary Vaynerchuk

An Interview with Gary Vaynerchuk

Ryan: Today we’re beaming with pride to talk with the ever-popular, innovative and energetic Gary Vaynerchuk. For listeners who are like, “Vayner-who?”, Gary’s got an incredible resume - he got into his family’s wine business as a teenager and took it from a $3 million dollar business to a $45 million dollar business. Gary’s the author of the books The Thank You Economy and Crush It. He is the founder of Wine Library TV, co-founder, and co-owner of VaynerMedia, and a super popular speaker, social media expert, and marketing maven.

He’s doing an incredibly nice year-long interview project where he chats for 15 minutes every day with one person who signs up for an interview with him. Spots filled up quickly, so we snagged our chance when we could. We’ve been hoping to interview Gary for months, and here he is. Gary, nice to talk to you today!

Gary: Thanks so much for the nice intro.

Professional Questions

  1. Ryan: Working in a wine store changed your life and gave you a crazy passion for customer service and connecting with people. Now you work with clients through your brand consulting agency. But no matter where you end up working, keeping current clients happy seems to be a big part of your success. What kind of advice can you give other business owners, or hustlers, that pertains to keeping clients happy?

Gary: Yeah I mean you’re absolutely right. At some level, you can’t really build a real business unless you’ve got retention. You can’t just keep getting new clients, right? If you’re not holding onto them you’re really wasting the efficiency. I’ve always believed in that - holding onto customers. Obviously it’s the bedrock of what I do at Wine Library - it’s pretty much becoming the same theme at VaynerMedia. Really, I think the advice is quite simple, which is listen - really understand what makes your clients tick. What are they looking for, what do they want, what matters to them most? And then actually overdeliver on it. It’s really stunningly simple. So my words are not profound; it’s been my execution that has been.

Ryan: So would you say that it’s more “underpromise, overdeliver?”

Gary: I actually overpromise and then overdeliver. Right? I don't think it’s a strategy of underpromising. I think it’s the understanding that if you listen carefully, and you know you can actually deliver on the ask, then you go all in. If you can’t, then you talk it out and try to reset expectations.

  1. Ryan: In terms of happy clients, at Happy Dog, one of our challenges is just helping our customers see the value of their long term investment in Search Engine Optimization and online marketing. Online marketing can be a hard sell, especially with organic search because you don’t have an “on” switch on Google, and sometimes it just takes a long time to build that presence. Do you have any advice on how to encourage clients that a solid online reputation will pay off in the long run?

Gary: Yeah, I mean, I think you’ve got to tell a story about people that have also done it and what the benefit has been, right? I mean, it’s really easy for me to talk about the value of social media because people like yourself that actually know what’s happened to me or have watched it happen understand there’s been a true ROI, right?

So, to me, once you’re in the business, the case studies really matter; people learn from other people’s learning. There are clearly people that went from the eighth page to the first page for results on ice cream. That mattered to them, and that’s why SEO matters, and then that story makes the person that has a furniture shop, or an insurance agency, or is a lawyer, understand, “Oh, I see.” But what the biggest problem for you guys is, and the same thing for me with social media is that you’ve gotta convince people to think long-term. That’s harder than I thought it would be. I’m surprised at how many businesses are only concerned about what happens in the next three to six months.

  1. Ryan: You brushed up on social media a little bit. You’re heavily tied into social media. You’ve obviously been using it to your success, but I’d bet you see time and time again businesses or even people not using social media to its fullest advantage. If you had every small business owner sitting in front of you, ready to listen, eager to learn about how to use social media, what would you teach them?

Gary: I would teach them that they’re probably spending 50-80 percent of their time and money on dumb crap, and if they took that money and actually applied it to the actual customer on social networks they would get a much bigger ROI.

Ryan: And sticking with social media, I’ve just gotta ask you this because I’ve got you on the phone. I think it was a month or two ago, you posted a really great Tweet. It was really simple, it was just: “Does anybody want anything?” And then somebody said, “Yeah, I want some eggs.” I just had to ask you about that; I thought that was so cool. I’m smiling just talking about it right now. How did that affect you and your social presence, and what kind of impact did that have when it all went down?

Gary: So for the people listening, I do this a lot, I think what social allows you to do is listen more than talk. Everybody wants to Tweet, Facebook status. I’m much more interested in listening, and trying to bring them value, and then talking. I asked, “What can I do for you?” And somebody said, “Well, you can get me some eggs.” You know, I’ve done this a lot in the past where I’ve done random little silly things. But on this specific day, the eggs were sent...much as I have done with other things, with t-shirts, wine, signed books, or just to call them and say hello, I always do this. But on this specific day, the person who asked for the eggs did a blog post about it, which kind of went a little viral, and it was picked up by the Huffington Post, and they wrote a piece about it. The end result was that doing the right thing ultimately paid a dividend. I’ve done it four, five, six, seven, eight more times earlier in the year, and nothing happened as far as exposure or people knowing about the story. But this time it did.

And that’s kind of what I always believe in, which is doing the right thing always kind of pays off. This was one of those moments where everybody was fascinated by the fact that I delivered this guy 20 dozen eggs. He made a blog post. People thought it was interesting. It just kind of caught fire, which lead to a lot of awareness. More people followed me; more people cared about me. It’s just kind of how it works.

Ryan: Yeah, that was super cool, and it really goes back to everything you do. I thought that was awesome.

Gary: You knew about that from serendipity, right? You didn’t know about the time I delivered somebody oranges, or the time I called four people and gave them advice, or hundreds of free signed books, or stickers, or I once gave somebody my sneakers I had. You know, like, things like that. Those stories never made it, right? That person never blogged about it, or they did, but nobody else caught it. When you’re doing the right thing without expecting something in return, you have a much better chance of ultimately getting something in return because you rinse and repeat it. I didn’t get down on doing things like this because I didn't get anything for it; I did it specifically for them; I just happened this time to affect a lot more people with that one specific move.

  1. Brooke: Gary, I love that doing something nice for people - in some cases, it turns out into great content for you, and in some cases, it’s harder to measure the ROI probably. This leads to my next question really nicely. You mentioned that this blog post about the eggs went viral. You’ve preached the value of content marketing loud and clear, great content, just putting great stuff out for your customers all the time. We read on Forbes that you hired a full-time content person to follow you around and turn what you say into content, which is so cool. I’m just interested in your process as to how you go about creating great content. You know as well as anybody that you can’t just throw content on the Internet and expect people to read, watch, listen. There’s gotta be some thought behind what you put up- what’s going to engage people, what’s going to be interesting or an awesome story. Are you a believer in “content strategy,” or are you more impulsive about the content you create?

Gary: I think both, right? And I think the reason... if you look, I haven’t pumped out that much more content since Steve’s been involved. I think that’s important to understand: you can’t just force it for the sake of doing it, right? And so, I think that if you don’t understand that it has to have value, you’ll never win. No matter how much or how little content you put out. That’s number one.

Number two, yeah I know what I talk about, and so I’m watching trends, I know that today Instagram announced its video and I’m sure I can add thoughts to that conversation, that’s a strategy. It’s things that are happening in my world that I have the right to and can speak about.

At the same token, sometimes things happen serendipitously; sometimes I have a meeting that makes me think of something, or I say something or even these interviews have been bringing up serendipity. It’s always a mix of the two. I’ve left hundreds of good pieces of content on the table over the last year just because I don’t have the infrastructure of somebody reminding me or nagging me or helping me, so that’s what that’s about.

Brooke: You have a book coming out pretty soon on storytelling in a noisy world, is that correct?

Gary: That’s right, so that comes out Nov. 26. It really focuses on how you tell a story on Facebook, Twitter, Tumblr, Pinterest, Instagram, how do you put out content that’s compelling on these platforms, in the essence of actually respecting these platforms as much as respecting what story you’re trying to push out. That’s what the book really focuses on.

  1. Brooke: Can’t wait to read that. Going off of the topic of storytelling and getting people’s attention in a noisy world, what do you think about having your own voice when creating content? It seems like it’s pretty important to be yourself, to resonate with people and to not look like the next guy. We really see you embracing your bombastic personality even if some people might criticize you for it, say you’re way too out there. Why do you think many companies are so afraid to be themselves or be different?

    Gary: Well I mean, I think it’s the same reason so many people are, which is they just worry too much about what other people think, or they might not be doing the right thing, right? The reason I’m so comfortable being out there is that I know that my intentions are pure. I might not be your style, but I’m not in it for the wrong reason. I think a lot of brands and businesses know they’re doing things that aren’t exactly perfect, and that hurts them, and they don’t really want it out there, and thus it keeps them away. Or they’re insecure. A lot of people are insecure or really crippled by people that are negative to them, or can’t deal with those things. It’s human traits that keep people out of it, you know?

Brooke: It seems like you’ve got to be kind of fearless and pretty courageous to be different.

Gary: Or I’ll tell you another thing: I wouldn’t necessarily say I’m fearless, I’m just respectful of what other people think. I wouldn’t call what I do predicate on being fearless. I call what I do is predicated on the fact that if somebody thinks I’m not good, or too out there or full of crap or hot air, I actually respect them; I’m like, okay, that means that I need to do a better job communicating. And I think that a lot of people don’t respect their detractors, and I think that hurts them.

Brooke: You’ve got to listen to the criticism, right?

Gary: Yeah, listen; if you want the praise, you’ve got to respect... on some level, the criticism has been far more valuable to me. It gives me another perspective. I feel very fortunate that I get thousands of pros for everyone con. I mean, how can you not take those odds?

Brooke: Good point.

Gary: I see people all the time, put it out there, put it out there, get one negative criticism, and they just cripple. I’m like, I get it. I’m completely affected by my negative comments. But you just have to understand, that’s just the way it is.

  1. Brooke: Going off of the thought about being different, taking risks, doing what you have to do to connect with people... we’ve always seen you using raw, emotional tactics to connect with people. You’re definitely an interrupter, Gary. You interrupt the norm. A lot of companies are not willing to do that, whether they’re afraid of the criticism or they’re afraid of doing something that hasn’t been done in their field. Thinking about an interruption as a tactic - you know, sometimes it doesn't work. Take up pop-up ads on smartphones as an example. Most people are pretty turned off by those. What advice can you give someone or a business on how to effectively interrupt and effectively change the game?

Gary: I would say two things: one, I don’t think pop-up ads on mobile devices are interrupting at all, meaning that I don’t think that was a failed interruption. I actually think that was a lack of innovation. I think that was people taking what worked on the web and just applying it on the phone. I actually thought that it took no creativity or interruption. So I just really want to make that point because I want you to see what I’m about to say next. I don’t really view myself as an interrupter. I just feel like I’m just willing to do what’s working at that moment, and most people aren’t. I think that’s a really important distinction. I wanted to tell stories on Twitter in 2006, 2007, 2008 because it was right - there was something actually happening there. So I don’t do much for the sake of the interruption value, or the shock value, or the rubberneck value, or the “oh, this is how you break through the noise” value. I’m stunned how much credit I get for just doing what’s right at the moment. Do you know what I mean? Like to me, I was doing banner ads in ‘95, ‘96, email marketing in ‘97, and search in ‘98. In that essence, that would be considered interrupting because it was just early, right? But it wasn’t interrupting; it was doing what was gonna eventually become even bigger and more important. I love having the advantage of knowing what something’s going to do in the future by actually doing it. People have opinions about Vine, Snapchat, and Tumblr, and they’ve never used it.

Brooke: Do you think this ability to be one step ahead, or right in the right moment for doing the new stuff, do you think that this is in your DNA?

Gary: Yes, I do. Which is why it’s so easy not to get caught up in my press clippings. I got lucky that I intuitively feel things that customers are going to do. And so, what? That’s just like somebody who’s good at basketball or can sing. Yes, I think that’s what I have. That’s why I always go all in, because I’m now 37 years old. I mean, I one day showed up at a baseball show and sold all of my baseball cards at 50 cents to the dollar because I decided I didn’t like the way the room was acting, and the way that people were feeling. It felt like I was at the end of it. I sold them all, and all my friends thought I was crazy. The whole market collapsed six months later. That wasn’t being taught into me - that was just me respecting the fact that I pay attention to people. It just felt like the enthusiasm was gone, and it was obvious to me.

Personal Questions

  1. Brooke: You’ve got good instinct. And hard work - you have a hard work ethic. Transitioning into more personal questions per se, you were born in Belarus and your family immigrated here. You come from a hard-working family. You’re a guy who knows you have to work hard if you want to get somewhere. At the same time, you think about how much work that is. It’s tiring to be a game-changer. Do you have advice on how to keep that energy and forward motion to keep doing hard work, changing the game, keep doing a great job at what you do?

Gary: I think it’s predicated on doing what you want to do at all times. If you want to take a break, good. If you want to check out for a month, good. It’s about self-awareness. If there’s a way to create self-awareness, that would be the answer. Because the reason that I’m always good is that I’m doing what I want to do. That puts you in a happy mood. I’m taking a lot of days off in August. I think I just need it. I’ve really been going hard. My kids are growing up; I want to spend time with them. It’s super anti my hustler brand, but I don’t care. It’s what I want to do. If you continue to put yourself in that position, you have a better chance of not burning out.

Ryan: So there’s no magic “Gary Vaynerchuk” pill that you can take that lets you go at it for 20 hours a day?

Gary: If there was, you’re absolutely right, I would create it, and I’d be well on my way to the Jets by now.

  1. Ryan: You’ve spent much of your life out east, growing up in New Jersey and working in your dad’s wine store there. The culture on the East Coast seems to fit that fast-paced, high-energy noisy, exciting vibe. But we saw VaynerMedia has an office in San Francisco, too, that was a little different. So I’m just curious: does the east coast have a special place in your heart, or are you just going to be happy wherever you go?

Gary: I would definitely say I’m an east coast kind of guy. The East Coast has a special place, but you know, San Francisco's one of my most important and favorite places. I mean, the two cultures that over-index in San Francisco are tech and wine culture, in comparison to any other city. It’s a very natural place for me; I’m a big believer in it.

  1. Ryan: I know you’re big into football. You have a goal to own the NY Jets. I’m behind you 100 percent. I love lofty goals, and I think you’re going to achieve that. That being said, I know you have a keen interest in the Jets. We’re big football nuts here at Happy Dog as well. I’m just curious about the quarterback controversy. I just want your opinion: is Sanchez going to start, does he have too long of a leash? You know he’s throwing more interceptions than touchdowns, and then he fumbles, and then they draft Geno Smith. I’m just curious to what your thoughts are on this.

Gary: Yeah, I mean I think at this point he’s lost all the equity he had from his early success. It’s going to have to be pure capitalism. Whoever wins it, wins it. That to me is just fine. If Geno’s not ready, fine; if he outplays Mark in the preseason, great. And so, I think it’s a good situation of pure capitalism. Let them push each other, and we’ll see what happens.

  1. Ryan: Staying with football, what is your take on the Vikings? What do you think about them, or should I ask, how much do you love them?

Gary: What’s really interesting about the Vikings - I’m actually very good friends with the Wilf family that owns the Vikings. I actually even have a call with Jonathan Wilf today, the son of Zygi. So I actually would tell you based on that, you know, they are probably the team I most root for now in the NFC.

Ryan: That’s awesome. We’re huge fans here. And can you say that the Packers suck, right?

Gary: I can definitely say the Packers suck. I mean, I could say the Vikings suck. I only have a love for one team.

Ryan: We just like saying that over here. You 100% rock, and we emphatically endorse everything Vaynerchuk, everything you take on. Please take a second to tell everyone anything you would like to promote...

Gary: You know what, I’ll promote this: it’s Facebook.com/Gary. If anybody has any further questions, feel free to come there, and I will be happy to answer them.

Ryan: Guys, go here, it’s awesome. I’m very happy I got to talk to you, you’re very gracious. I know we probably went over on our time, so I really appreciate you being really kind to us at Happy Dog.

Gary: Thank you guys so much for this lovely interview.

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