The Gary Vaynerchuk Interview: Successful LifeHacking

People often focus exclusively on the business of Gary Vaynerchuk, but on a Friday morning after a long flight back and late arrival, Gary scheduled an early interview to talk to me about the man behind the hustle. In this interview, he speaks on the personal elements that continue to give him success, an honest look at what it takes, and how you can get there. The transcript below is of one continuous conversation we had, broken into the topics we covered: 


Dr. G: I want to thank you so much for giving me a call today, I know you’re a really busy guy


Gary: No worries, thanks for the interview

On Putting Family First 

Dr. G: You talk a lot about putting your family first, and I really like the fact that you talk a lot about your priorities. I was wondering, you’re such a busy guy, how do you demonstrate and keep that a part of your life? How do you implement that in practice with your travel, speaking and schedule?


Gary: You know, I think it’s evolved? At first, for a long time I would have answered this question with “effort.” You know just making it a top priority. You know you’re making choices everyday – do I go to this conference, do I go to this meeting, how late to I stay out…blah, blah, blah…but what I think has evolved over the last 12 months has been what I call more “extreme planning” – more vacations and hard core don’t touch the weekends, and that kind of gives me the…not permission, but mental permission at least for myself to work harder during the weekdays and when I am working – so that the extremities of going all in, both on the hustle and on the family time has become a better model for me over the last 12 months.

On Keeping Himself at the Top of His Game

Dr. G: That’s great…and you do seem to be at the top of your game. I mean, you’re always energized, you’re always quick. A lot of my readers might want to know, is what do you do to maintain the positive attitude. Do you have good physical health? How do you keep yourself at the top of your game?


Gary: You know, that one’s interesting because I think that’s a gift more than the work I’m putting in.  You know, you can always dissect these things…I don’t have a great workout regime, my eating habits are solid but nothing spectacular or anything I would want someone reading this to follow. I think what happens with me is maybe a bit of circumstance.

I’m so driven by gratitude. I’m just very self-aware of how lucky I am. I was born in a Communist country, and I’m very much a Capitalist, so I ended up in the country that most celebrates entrepreneurship and business chops and to have that be my natural gift is a whole lot of serendipity and luck. For me the cold war, when I was born was so…I am very aware of how great my parents are, and unfortunately I lost three out of my four grandparents very early on and I was born right after so I haven’t faced a lot of illness or death in my life – which I am 37 right now so that’s remarkable.

So I look at the big picture, and it’s just so obvious to me that things are so great that the little things like money or the ups and downs of stress, just don’t register as high for me I would say what seems to be the median average out there.

On LifeHacking Time Management, Work/Life, and Relationships

Dr. G: That’s a wonderful perspective. Are there ways that you “lifehack” that people may not know about you? I mean, you seem to cram so much into everyday. I remember reading that you encourage people to email you personally and that you respond to them. With the volume that you get, I’m not sure how you do it. So I’m wondering how you manage it…and if you ever run into problems like “always being on the phone,” or people telling you to put it down at some point. How do you really manage all of it?


Gary: A couple ways, I mean this is really going high level. First of all I married the right human being right? And I’m not kidding, I mean that’s really the answer. With a lot of communication up front in my relationship with really kind of quote unquote you knew what you were getting into right? She knew my ambition, she knew how I was wired and she’s also an amazing woman and with amazing empathy and understands how happy this makes me.

My hustle is really my entertainment. Answering people, engaging with people. Doing this… I’m going to work right now, right? And a lot of people who work the volume and intensity that I work – you know I just got back at midnight from CES right..and I got up at 7:00 this morning to spend time with my’s a real schedule, but…doing this interview is more interesting to me than taking the 10 minutes or the 15 minutes or what the cab ride is and playing Angry Birds while a lot of people…or watching a video which a lot of people do which is right – it’s their form of entertainment, it’s the way they wind down or find a moment of balance.

For me, my work is so much my passion that it’s just more entertaining to me than that alternative, so answering people’s emails and helping putting out content and engaging…. I’m such an extreme extrovert..I feed so much off of human interaction that this whole social media thing…you know there’s a very obvious reason that I’ve been overindexed in this latest movement of the’s because it’s so people driven and I’m not sure if there is anything I like more than people.

On Beating to His Own Drummer & The Importance of Giving

Dr. G: Yeah, I think that’s wonderful. One of the things I noticed is that obviously you stand out because you are so interactive with your audience and other people and you’re not just selling yourself, you’re actually interacting with other people. I wonder because people tend to be so interactive in some ways, what people find so novel and rewarding about that with you…because I think that, you know, it seems to me that your style seems very novel in a time where we do interact but it seems more superficial. So what do you think people find so rewarding about your style of communication as opposed to other companies or other people?


Gary: I think I’m a very rare breed that is running a marathon in a sprinter’s world. And so, and I think you can understand where I’m going with this, so you know you’re right I don’t have a whole lot to sell. Yes, I’ll be a little bit aggressive when my new book comes out in the Fall, but when I’m “selling” for a month in the scheme of every 2 years… You know, I feel like the best way to get is to give, and I’m very willing to put in the work and have outrageous amounts of patience for a guy that comes across so frantic.

So I think the answer is that I’m really am not trying to do anything other than give in precontext and build a relationship. And listen, you know this interview is actually a great sum of the whole situation. I have plenty of PR people and agency handlers that are really not thrilled with me doing this. They feel like I’m overexposing and these blogs have no audience and nothing makes sense on paper, right..analytically or the way it’s been done. But for me, I always beat to my own drum. I, you know, want to think context. You know how this interview went down. I have no idea how many readers or…I’m assuming that I’m going to expect one person, the person that I’m interviewing with, everything else is gravy. So, you know most people just don’t want to put in the work and don’t have the patience and aren’t….You know, I get a lot of joy out of “giving” to my community, because I’m very flattered to have one.

On Hiring the Right People

Dr. G: You know, I noticed that you surround yourself with people that seem to be great people as well, and that was going to be the next thing I was going to ask you. People you hire at Vayner all seem like really great people. I mean, I talk to some of them online, and your assistant is fantastic and personable. They all seem to really love what they do, and I was wondering what characteristics you look for to build such a great team?


Gary: I’m always looking for EQ over IQ. I’m not so worried about your skill set because I feel that can be taught and honestly I’m looking to teach other kinds of skill sets. I’m looking for people skills, people that generally like other people, but very honestly it’s not what I’m looking for, it’s what I adjust to when I have it, and I have something different than what I do. Meaning, I…You know, in one interview or two interviews I have great intuition, but you’re not always right. It’s about once you’re living with them and engaging with them – weeding out the things that don’t work for you and embracing and growing what potential is there.

On Working with Family

Dr. G: That’s great, so you know you started working in your Dad’s store, now you and your brother started a media company. Can you tell me a little bit about what it’s like working with family. I mean are there any pros and cons, or advice you’d give to people who thought about bringing family into their business?


Gary: It’s very hard. It takes a couple of major things. It takes aggressive communication, and aggressive not in like yelling…I mean aggressive in like overdelivery of communication – lots of talking, lots of talking. The pro is you’re spending time with people you love. The amount of time that we spend at work is enormous, and so having that ability to spend time – even the serendipidous three minutes or the crossing each other in the hall or’s amazing to spend it with the people that you love.

The cons are, it gets convoluded, you know, emotions get high. I have very different experiences. In one, I was kind of the apprentice and in one I’m the mentor, right, so I’ve been on both sides of it already at a young age. For me it’s been a challenge, but something I would never ever ever reconsider. I would do it all again and I’ve learned a lot about myself and the people that I love through it.

On Reaching Your Potential & What Holds People Back

Dr. G: I think it’s wonderful how you’ve come full circle in that way. One of the things I do as a Personal Development Consultant is help people reach their potential and I’m wondering when you look around, what’s the thing you notice holding talented people back? You’re around a lot of people who are quite talented who maybe are not going to reach or won’t reach the level that you do, so I’m wondering what you see is a major factor that seems to hold people back?


Gary:  I would say the overarching one, the one that’s blatantly in my face is self-esteem, lack thereof, or not having the proper parenting to embrace their strengths instead of their weaknesses. I’m completely, you know, enthralled with the idea of like people working on weaknesses vs enhancing their, I’m a big, big big one of the latter.

I think that you find..if you’re honest with yourself and you know what you’re good at, you go all in on that. I think that’s a much clearer path to happiness. And if you’re fortunate enough to have people that surround you that support the [indiscipherable] then you’ve got a real shot.

A lot of people in the 1920s, 30s, 40s, 50s  who were amazing athletes who were talked out of it by their parents because that wasn’t a practical living because outside of a couple of superstars, you know, it was a tough kind of life. A decade later, when they were kids, athletes were making millions of dollars. So, you know, I feel like betting on your strengths is a big one, and the thing that I see people struggling with is they don’t have any confidence in themselves from the environment that embraced and enhanced that.

On Overcoming His Own Obstacles

Dr. G: If you were to look back on yourself, is there any…what was the biggest personal obstacle that you’ve had to overcome and what was your key to getting over it. Everyone kind of has their thing, and I didn’t know if there have been any big personal obstacles. I know you’ve spent time at one point, you know, you said you were spending 14 hours a day doing videos hoping for 30 views. I’m wondering what your biggest person obstacle was and how you got over that.


Gary: My biggest obstacle to me, was definitely the fact that I was a very poor student. You know from 6th grade to my senior year in high school – it was tough thinking I was in school considered a “losing player” by my teachers, my peers, my parents, my peer’s parents. But, it’s funny, looking back on it, it’s shocking, how much I didn’t care.

It’s funny, I gave a care but I didn’t, and it’s kind of been the M.O. of my life which is I cared so much about what every single person in the world thinks about me which is why I probably give so much…on the flip side I can live without caring about it at all. And so that contradiction is my strength and so that’s kind of how I look at the world. So, it was rough at the time, it was tough. I knew what I was doing, I was honing my business skills, but the rest of the world didn’t…except for my Mom which is why I pulled it off.

On His Newest Project

Dr. G: That’s great. You’ve mentioned that you have a book coming out in the Fall, do you want to talk a little bit about what that’s about and give any information on that?


Gary: It’s called “Jab, Jab, Jab, Jab Jab, Right Hook” There’s a lot of content out there so how do you dig through. I’m going to talk about the thesis, why it’s happening, how mobile’s changing it, why Facebook, Twitter, Tumblr, Pinterest, Instagram all these things are working while and why you have to figure out how to meet a need if we talk on them and why and how, then through content and microcontent do you achieve your business goals while giving back to the community that’s consuming it. So really just figuring out how to hack the world in a way where there’s so much content being produced, and so much noise on social, so you can break through.


Dr. G: Now you have a multi-book deal, and one of the things I was interested in is that I believe it was your first book, “Crush it,” that you actually took more royalties than initial payment…that was something that was pretty new also. So where do you think, I know that you went to Ida College..Where did a lot of your business acumen come from?


Gary: Definitely not from school. I mean, I was a businessman when I was 5 years old. It comes from my Dad’s DNA, my Grandfather…both my Grandfathers, who were pretty entrepreneurial as much as you could be in Russia without getting in trouble. So, I just think it’s pure genetics. It’s like asking Roger Federer where it came from. You know, you put in a lot of hours honing it. You know, since I’ve been a businessman since I was 5, in essence I’ve spent all the hours that I’ve put in the Wine business instead of studying in school paid off in the world that I’m actually going to live in, so I just think that’s kind of a DNA thing.

On Evolving Your Own Career

Dr. G: When you first entered the wine business, I’m sure you weren’t aware that you would really be focusing on social media as much as you have…what was that transition like because certainly you became known as kind of the “wine guy”..and then “the social media wine guy” and then “the social media guy.” So how has that transition been, and how did you position yourself in that way?


Gary: I think only by putting out content, right? I mean you become what you talk about and what you put out to the world so as my interests changed, the opportunities I saw changed… You know, I could have been the “ecommerce guy” we had the first ecommerce website for a liquor store, a local liquor store and used it as a way to communicate… I’ve always been innovating in marketing, whether it was SEO, whether it was email submissions, I was always doing something new. What was different about social was that as I was doing social, I was also using social to talk about what I was doing and that’s how the story evolved…and so it was a reality of what the marketplace has become. The fact that I could talk about it while I was also doing it evolved me from just being “the wine guy.”

Real Advice on How to Pursue Your Own Passion

Dr. G: Fantastic…Just to wrap it up, what advice would you give to somebody looking to be where you’re at or looking to pursue their own passion?


Gary: I think the biggest thing is to look in the mirror and not lie to yourself. I think we all want to be something in our minds, but we may not have the talent for it…and I mean that…and it’s kind of a cold pill to swallow and may not be the most “rah rah” piece of advice, but the reality is that there’s a lot of truth to that and so I think if you’re honest with yourself and hone in on what you are good at and recognize that we live in a world where being good at something very narrow has the potential to be very successful, which is not the way the world was prior to this internet revolution.

I think you embrace those two big things and start talking about or build a business around those things are you have a real shot at being successful, and so I think those are things to think about. Also recognize that you can get to anybody in today’s world. The ability to tweet at anybody and just ask for 5 minutes or 10 minutes…a lot of people won’t, but a lot of people will and I think people should take advantage of that and recognize that people impact your life. The people that quote unquote rule the world, realizing that you can get to them now is much easier than ever before is a little bit of a secret notion that I think people should take advantage of.


Dr. G: Well thank you so much for your time, I really appreciate it. I know you had a long flight and we look forward to seeing you own the Jets one day and maybe bring the team to greater heights.



Julie Gurner

Dr. Julie Gurner is an executive coach, host of "The Relentless" podcast, and speaker.