On The Line with Gary Vaynerchuk - Journey of a Frontman

Today, I have the honor of interview one of my biggest influences, the co-founder and CEO of VaynerMedia, a video blogger, an author, and a public speaker, Gary Vaynerchuk!

Alex Obert: The way that I was introduced to you was your legendary Web 2.0 speech, and in regards to that, why do you encourage people to start their own blog?

Gary Vaynerchuk: You know, mainly because I think it’s cheap at that, meaning it’s so inexpensive to start one, virtually zero. It gives people a voice to the world and an opportunity to build something around the things that they want to talk about. I mean, from me, I come from a business angle, some people come from an artistic angle, whatever it may be, but you know, at the end of the day, when something is free and it has the potential to bring you happiness, it becomes an interesting place to look at.

Alex Obert: When you deliver speeches like that, how do you want people to walk out feeling and what do you want them to be thinking?

Gary Vaynerchuk: You know, I think it’s different every time. Obviously, I’m not unaware that I can be inspiring and all those things. I mean, your agenda is to be right more than anything else. If I can be right and if I can get one person out of the seven hundred, two thousand, five thousand, thirty, whatever the audience size is. I really go in there quite realistic. I think most people are lazy or don’t have the talent or are content or are super happy with the way it is and so knowing that, I know that I’m only really gonna get lucky and get one or two people to be impacted, and to me, selfishly, that’s exciting, and not selfishly, it’s a really nice thing to happen.

Alex Obert: In regards to you and what keeps you going, how do you stay motivated daily?

Gary Vaynerchuk: You know, I think that I’m super hungry. I’m motivated by awareness of my talent. I’m super in tune to the fact that I was gifted with something and so, I think I’m motivated and driven by the fact of almost a weird sense of responsibility to execute what I’ve been given. I feel like I’m so lucky, I might as well go for it.

Alex Obert: When you become inspired, who are some of those people over the years that have inspired you and influenced you to do what you want to do?

Gary Vaynerchuk: I think it would be my parents, believe it or not. I’m not super inspired, meaning I’m self inspired. I don’t really consume a lot. I’m inspired by people that go all in. It’s weird to me, it’s funny actually, that I say that, it’s almost in reverse, meaning I’m not really inspired and I’m kind of always inspired. I’m always inspired by random stories of a friend’s mom who raised three kids on her own or a dad who works ninety hours a day. It’s not like any famous person ever, it’s like “Oh, I want to be like that.” or “Oh, look at that.” You just hear less about any of these accomplishments or stories. I’m very much in my own zone and in my own head. I’m almost kind of like a polar opposite meaning nobody inspires me and someone unlikely inspires me.

Alex Obert: What does it mean for people to go up to you and tell you that you influenced them, that you’re influential, and inspiring to them?

Gary Vaynerchuk: Now that’s where I get fucking pompous, right? Like, that’s such a high. You know, it’s funny, it’s equally selfish and not selfish, right? Like, I live for that. Getting that people or people coming up to me, do you know how crazy that is, bro? Do you know crazy of a feeling it is for somebody to come up and tell you that, like “Crush It”, especially, my book. So many people come up to me and said it changed their life. It blows my fucking face off. It’s almost impossible to believe.

Alex Obert: Now I recall a couple years ago seeing some videos of you, I believe it was in front of a webcam, where it wasn’t a big speech, it was just you by yourself and you were giving people advice such as things about a having a big or small voice, it doesn’t matter about that, but it matters about the content of your speech, things like that. Now what were you looking to accomplish with those videos and why did you choose to do them in an intimate setting like that?

Gary Vaynerchuk: Any time I’m inspired to just talk and I feel like I’ve got something to say, I’ll do it on my own webcam. I’m into that stuff, I want to do more of it, I’m just so busy. I have a weird feeling, a need to talk, right? It’s a very selfish thing. I love to talk and so I just do it. I’m not super concerned, there’s no real master plan. When I hear that question, it’s funny, I try to come up with the answer for you, but there’s no real big agenda. It’s just kind of, I enjoy my community and I’m lucky to have people give a shit about me. I, in turn, give a shit about them. If I have something to say that can bring value to the conversation, I’ll pump it out.

Alex Obert: When you were starting out, not necessarily with the wine career, but in terms of blogging and becoming a voice for the people, what were some of the most important opportunities that you received when you were starting out on your own?

Gary Vaynerchuk: I don’t think anybody gave me the opportunity, I think the internet has given us all of the opportunity, right? I just recognized that YouTube was important. I just recognized that the internet was important. And I just realized that anything that you want to happen in life, you’ve gotta go take it, and that’s what I did.

Alex Obert: I recall hearing in one of your interviews that you capitalized on using websites when they were early, before everyone was using them. You used YouTube early on and Twitter.

Gary Vaynerchuk: And Tumblr early on. Absolutely. You know, the sooner the better, the more upside you have, and so, I’m a big, big believer in that stuff for sure.

Alex Obert: How do you feel that Twitter is important with communication and promotion?

Gary Vaynerchuk: You’ve got hundreds of millions of people using it and it’s the one place where you can get involved in any conversation and it’s not considered creepy. Facebook, all those other things, you’ve gotta be friends with the person. This is the one place you can just do your thing. It’s one big cocktail party. It’s think it’s as special a platform as there is.

Alex Obert: Now in regards to going after your opportunity and when you had an early start, what should someone in their early twenties, perhaps someone who just got out of college do to go after their dreams and create the opportunity?

Gary Vaynerchuk: Be willing to be ghetto. Meaning eat McDonald’s or Ramen Noodles every day, sleep on the floor with six buddies in an apartment, live in your parents house. Be willing to do what you want to do for free because at the end of the day, it’s by far the most practical age to pull off that kind of stuff. Unless you have student loans, I would attack it as hard as you possibly can and basically just work for the person or company that you want to work for for free, they’ll take you, and then show them what you’ve got.

Alex Obert: How should people be applying themselves outside of work, in their free time, in regards to doing what they want to do, such as blogging?

Gary Vaynerchuk: That’s just like, you want to go get drinks with your buddies or do you want to go and play basketball with your friends or do you want to go and date, do you want to go hang out, or do you want to make your business happen? It’s all choices. And I think it’s allocating the proper time for you. For me, I was all in and hungry and I just gave up a lot of stuff in my twenties to get what I wanted, but it’s all in finding the balance. But knowing that you can get anything you want. I mean, the biggest thing for me, bro, to be honest with you, is I just don’t want people to bitch. If you’re like, “Oh, it’s not going great.”, you know, then stop fucking going out every Friday, Saturday, and Sunday and fucking work.

Alex Obert: In regards to the future and what’s going on with you, I want to touch base with you a little. So for example, what’s going to keep you up tonight and what’s been on your mind lately?

Gary Vaynerchuk: The only thing that really keeps me up, I mean what I really care about is the health of my family, so that scares me, like “I’ll never be healthy.”, all that. But in business terms, am I doing the right thing? I’m very patient and I talk a lot about running a marathon instead of a sprint, and I’m always like “Am I too patient?”, “Should I be doing a television show?”, “Should I start a two hundred million dollar fund?” Questions like, “Am I too patient?” That’s the only thing that keeps me up at night.

Alex Obert: What is an example of great advice that you received, whether it be early on or present, or any time throughout your life?

Gary Vaynerchuk: I would say my dad’s advice, his bond is probably the single thing that has made me successful outside of my DNA. He taught me much more morals and stick to your word than I think I naturally had at that age. I think I was a little shit at thirteen, fourteen, fifteen, and his guidance there was huge.

Alex Obert: Now on the other side of the coin, because Journey of a Frontman involves music, I’m just curious as to which bands and musicians you listen to.

Gary Vaynerchuk: I’m huge on hip hop. I think I’m pretty ghetto in a lot of ways and I love the up and coming grind story, so a couple things. One, I love hip hop and up and coming artists right now, I’m listening to a lot of Rome Fortune, for example. A lot of people don’t even know him yet, but they will. So, big ups to hip hop because I love the story of coming off of the streets and making it happen. And then I love really sugary, fluffy pop music, just because I get very caught up in songs and I like it. So, those are the two things I like.

Alex Obert: Are there any inspirational movies or books that you have seen or read?

Gary Vaynerchuk: Definitely not books. Movies, movies, movies. Not really, man, I’m a weird dude when it comes to this stuff. I’m in my own fucking world. I don’t consume a lot, but I produce a lot of content. But I’m not a big consumer of it.

Alex Obert: So in regards to your free time and I know you’re huge on the New York Jets, but aside from that, what do you do in your free time and how do you feel you live life to the fullest?

Gary Vaynerchuk: I feel like I live life to the fullest because I do everything that I want to do. I’m in full control. I have an amazing life and I’ve had an amazing career that allows me to mainly do what I want. Outside of the Jets, fantasy baseball is a huge part of my life, I love that. I look forward to that each year. And every other minute is spent with my parents and her parents and my children and my brother and sister. Family is just huge for me. I’d much rather go out to dinner with my family than do anything else.

Alex Obert: Very nice. I like that.

Gary Vaynerchuk: Thank you, sir.

Alex Obert: I just want to leave with this, I want to know, what do you say to those who want to go after their dreams and risk everything?

Gary Vaynerchuk: I would say that in two to four years, you can figure out if you’ve got a shot at accomplishing it. And in the scheme of things, two to four years doesn’t mean anything. People waste two to four years all the time. So just do it because you’re not gonna regret it. You’re gonna regret not doing it when you’re sixty or seventy a hell of a lot more than wasting four years and not pulling it off.

Alex Obert: Also, I just wanted you to quickly fill me in on your upcoming book and what it involves.

Gary Vaynerchuk: What I’m writing right now is basically just trying to teach people how to put out content on Facebook, Twitter, Tumblr, and Instagram, all the social networks that I think matter now because I think matters now more than ever, people are spending a lot more time paying attention to those platforms and figuring out how to storytell and sell your shit on them is huge and that’s what I kind of break down in this book. It’s gonna be pretty good, man. “Jab, Jab, Jab Right Hook” (the name of his upcoming book) I feel very confident in it.

Alex Obert: And when is that coming out?

Gary Vaynerchuk: November 26th.

Alex Obert: I’d like to thank you very much, Gary, for this wonderful interview.

Gary Vaynerchuk: Thanks bro.