My Interview With Gary Vaynerchuk – Drinking Game Included

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I’m really excited to share this post with you! This was supposed to go live earlier this week but getting a transcript typed up takes a bit longer than I expected.

So to make a long story short, after several failed attempts, I finally got an interview with Gary Vaynerchuk! I’m a big Gary Vaynerchuk fan and I love what he was able to do over at WineLibraryTV and now at VaynerMedia.

You can find the audio and transcript of the interview below. I will admit that I got a bit nervous just before the interview and as a result, I annoyingly used the word “Awesome” far too many times. Therefore I had no choice but to turn this post into a drinking game.  This particular drinking game has only one rule – take a shot every time I say the world “awesome.”

OBLIGATORY WARNING: Drink responsibly 😉

Press play below to hear the full interview:


You can find the transcript below as well. Enjoy!

Jordan: Ladies and Gentlemen, welcome and as always thanks for being here with me. I’m Jordan from and I have a very special guest with me today. He’s the CEO of a social media brand consulting agency, he’s a wildly successful video blogger, co-owner and director of operations of a wine retail store, he’s a two-time bestselling author and public speaker on the subjects of social media, brand building and e-commerce. He’s been featured in The Wall Street Journal, GQ, Time Magazine, and he’s appeared on Late Night with Conan O’Brien and The Ellen Degenaris Show. – GARY VAYNERCHUCK Thanks for being with us.

Gary: Thrilled to be here, thanks for putting me through.

Jordan: Awesome. Well Gary, your story is honestly frickin’ amazing. you’re a Russian immigrant to the us and your success started at your families liquor business, isn’t that right?

Gary: Correct and a lot of Kudos to my Dad who came to this country with no money and no language and built his way up from stock boy to liquor store owner so I was lucky to go into a family business and obviously I was able to escalate it from a $3 million to a $60 million dollar business but it wouldn’t have been there without his hard work – so its a real family story.

Jordan: That’s awesome, I mean that’s a great story. And your from what is now belarus, correct?

that is correct.

Jordan: that’s awesome

So, what is the secret? How did you take a 3 million dollar family business and really grab hold of the reigns with your father and turn that into a 60 million dollar company?

Gary: I think its a couple things. One, it’s just natural talent. I mean the truth is I could sit here and you know ponticate all day long about how good I am, this that and the other thing. But the thruth is, much like lebron james or adelle, or you know plenty of other people there’s natural talent, I was just lucky enough to figure it out at an early age.

I sold baseball cards, and had lemon stands when I was 5, 6, 7, sold baseball cards when I was 10, 11, 13 – so I put in the work to be honest. I learned so much about business that by the time I was 16 years old, I came into my fathers business bringing value, bringing ideas bringing intuition. So ultimately the real answer to your question, after I setup that context, is innovation. I launched in 1996, I did email marketing in 1997, I did SEO and SEM in 1999, I did blogging in 2003, I did youtube in 2005.

Jordan: That’s really awesome. So you were an early adopter to many things, you spoke about SEO and today we have the Panda and Penguin updates (I come from an SEO background), and it’s a lot harder to do SEO than it was in the earlier days. You were also an early adopter to things like twitter, video blogging, and other online marketing techniques. Do you think you could do it all over again if you started today?

Gary: Absolutely – I know exactly what to do right this second with snapchat, I’ve already got my thesis on Google Glasses which isn’t even out and wont be mainstream for another three years. So yea because my talent is intuition and so whether its twitter or facebook or tumbler comes along and I jump on that, you know instagram came along and I jumped on that. I’ve always had an intuition to where the world the world is going and that’s been a big key for me, a big success factor , its why I’ve been a pretty good angel investor, and so i will continue to bet on that intuition and so I do feel I can do it all over again, I really do.

Jordan: Awesome, awesome, and you think it would be easy for others to do the same, if they spend those 10,000 hours to train themselves, do you still think it’s possible today?

Gary: If they’re talented, if they’re bringing value, and if they’re in early enough. You know it’s harder to win on twitter today than it was in 2007. And so its all about the timing at which and when you actually start executing against the opportunity and not waiting for it to be at scale and realizing that the early days are when all the actual upside lies.

Jordan: Interesting. Tell me about Google plus. It seems to be, at least from my perspective, a more neglected or more quiet social network. There’s not as much conversation going on there. Are you active there and what role do you think Google plus will play just in terms of being connected to Google, search results, stuff like that, where do you see it in the future.

Gary: Yeah, so I’m not that active on it and that’s because it’s quiet and there’s only so many hours in a day, and we all go through that. But I do believe it in. I believe it’s a social layer, not a social network. And I think when you start applying Google Plus to youtube, android, gmail, search, you start getting into an interesting place. I think over the next two years it will be an interesting to see evolve and I kind of compare it to Reddit. You know Reddit was not the leader, Digg was, and then all the suddent it was the leader 7 or 8 years later.

Jordan: Digg sold for half a million dollars didn’t they, Digg is gone completely.

Gary: Yea so I think the real questions is you know, I think it’s got potential – it may not happen but I definitely think its got potential.

Jordan: Do you think its important for people to be there and spend time there today, or not yet?

I think they should pay attention to it more so than be there. Does that make sense? I think they should check in on it, fool around a little bit with it here and there. I think its dangerous. You know it’s kind of like a boxer that’s not a great boxer but has a knock-out-punch. Think they have a knockout punch and you could be winning for 11 rounds but then get caught in the 12th. I compare Google Plus to David Tua.

Jordan: I don’t know who that is but I get your metaphor.

Anyway, I’m curious, you’ve got a lot of stuff going on. You all heard my introduction. You work on a ton of different projects. You’ve had a lot of success, you’ve completely reinvented yourself as a social media brand consultant from being a wine expert. What is a typical day like for you. Don’t need a long winded answer but are you an early riser, do you stay up super late?

Gary: Yea I’m basically up at 7. I’m going to sleep between midnight and 2am. Every minute of that, during the weekday, is packed with meetings. Literally it is unheard of for me to have a 1 hour open block during that time from. I’m either in meetings and running VaynerMedia or I’m speaking/doing TV, or meeting investment propects for angel investing. But truly, truly, I don’t remember the last time I had 1 hour open with nothing to do on a Monday through Friday schedule from 7am till 10pm. Then I come home, spend a little time with my wife and more time on the laptop and it’s hustle culture.

Jordan: Wow, awesome but that’s intense.

Gary: Yea, it is intense. It’s way more intense than people think. You know? I don’t think people really understand what it’s like to work 15 hours a day straight, scheduled, hustling, hardcore and like doing it every day.

Jordan: But its easier if you love what you’re doing – which is clearly the case in your situation.

Gary: Absolutely! Absolutely!

Jordan: Well you mentioned VaynerMedia. So in the Spring of 2009 you and your brother AJ you guys got together to start VaynerMedia which is a digital marketing agency that helps fortune 500 companies find their social media voices, build their brands, etc. What inspired you to leave your video blogging and your efforts at WineLibraryTV and jump into starting an agency?

Gary: Who the hell knows! Truth be told there was an opportunity, I saw social happening, I wanted to learn more about corporate America, believe it or not. I have a long winded reason why and this seemed like a great way to do it without going for an MBA. And it’s kind of like getting an MBA while getting paid to get an MBA, instead of the reverse. So opportunity was there, I want AJ to learn a real business, one that had Cashflow and P&L and all of that. So that’s kind of what happened.

Jordan: Awesome, Awesome. Are you happy you did it looking back, in retrospect?

Gary: I never cry over anything. I mean so the answer is absolutely. Always. I’m happy about anything I’ve ever done this second of this conversation.

Jordan: Cool and I mean there’s only one of you but now you work with a large amount of clients. How do you scale that to provide top quality work and your own insight to your clients?

Gary: Yea I mean that’s the game we all play, that’s just about quality people. You know there’s 30 – 40 people at VaynerMedia of the 250, that really dominate and drive this business and we’ve got 40 to 50 more ready and waiting behind there wings. It’s about scaling, it’s about being a manager, it’s about empowering people, training people, making them better and so it’s a process but it’s happening. You know AJ and Kelly (my right hand), and STP, mickey cloud, and Marcus, there’s just a ton of people here, Tina our creative director. There’s tons of people that are making it happen.

Jordan: Sure, and Christa who I spoke with, she setup the interview, she’s seems like a good asset to have as well.

Yea, absolutely!

Jordan: So with VaynerMedia – is the goal with it to disrupt the ad agency world like you with WineLibraryTV with the wine world?

Gary: A little different. That was a little different. So it’s really the same in this way. It’s to disrupt the way we communicate about things. So WineLibraryTV disrupted the way we communicated about Wine. In my new book Jab Jab Jab Right Hook, is coming out in the fall, and I’m talking about to storytell in a digital world. Mobile, shareable, social, fast, micro, animated gifs, meme’s, we’re communicating differently and we’re trying to teach brands to do that. So I did that for myself and now I’m doing that at scale which is kind of whats going on.

Jordan: Awesome, well I think you guys will do a great job. You have a one page website so it’s tough to find out about VaynerMedia.

Gary: You know Vayner is kind of quiet compared to most of the stuff I tend to do. We’ve got a head start though and we really want to stick with it.

Jordan: Well I’m going to shift gears for a second. You’re a huge NY Jets fan which is interesting to me because I’m a proud member of the Buffalo Bills Backers of Budapest, Hungary – there’s all of 5 members of us out here…

Gary: I love it!

Jordan: I love that on your about page, on, you have written right at the bottom that one of your goals is to be an owner of the NY Jets one day. And honestly, you’re a lot closer to that goal than you were 5 years ago. So I don’t know how many people, had they laughed at you then, would still be laughing now. What do you think needs to happen for you to make like that come true?

Gary: I think I’m going to need a signature event, right. I’m going to need some investment, some business I start, really take-off and get me that  base 2-500, 500-1 billion payoff. It’s going to have to happen. By the time I’m ready to buy the Jets it’s going to be Billions of dollars. So I think it’s going to have to be something pretty substantial. The good thing is I’m being serious about the goal. I’ve done a lot of interesting things like meet with the lawyers who can actually make it happen one day. I’ve done a lot of learning and I’ve learned a lot. And you know it’s funny, when you shoot for the Galaxy, you end up in the stars. And so, if I don’t by a 3 billion dollar football team a lot people are going to think I was not successful with my career. Number 1…I find that fascinating as to why I have done that to myself and number 2…it’s going to really funny if I end up amassing 500 million in my career but that ends up looking like a failure…but that kind of excites me in some weird way.

Jordan: I love that saying – shoot for the moon, you’ll land among the stars. That’s exactly right. It’s awesome that you talk about that goal as a definitive mission statement to have. It’s really great to shoot for.

In your book Crush It! Why Now Is The Time To Cash In On Your Passion you offered people a roadmap of how to succeed in the business world by building your personal brand or following your passion. What kind of advice do you offer to people…I mean right out of college I got a job and it turned out that 6 -month into that job I really didn’t love what I was doing. How do you pivot from maybe being 10 years into a career or 6 months into a career and not being passionate, not waking up in the morning and loving what you do?

Gary: If you’re 3 months to 3 years into your career, just leave. Your just in early, you’re young enough and you can just sleep on your friends couch. Later on you’ve got mortgages and family and all these other variables that are dictating it. Like I wrote in Crush It! It’s about 6pm and on. Get home and start working on something else that starts bringing you revenue and allows you to syphine off what you don’t want to do so you can do what you do what to do.

Jordan: So under 3 years – just go for it.

Gary: Yes – realizing that living with 10 buddies in a studio apartment is fine.

Jordan: Right eating ramen noodles, going for the dream.

Gary: It just is. It just is. You know no 23 year old right now or 24 year old believes me but they’ll book at realize I was right.

Jordan: As a 23 year old talking to you right now, it’s definitely something I felt comfortable doing. Looking back, I don’t regret it. Still grinding right now, living paycheck, working the consultancy grind, but I agree with that advice. Under 3 years just go for it at this age.

Gary: Good for you.

Jordan: Your energy, your ambition…I’ve watched so many interviews with you. You’ve got such passion when you speak. I saw that Pierce Morgan spot…it shows no signs of dying…where are you going to take this past VaynerMedia, past the video blogging, past the consultancy thing – What’s in the future for you and what can you tell us?

Gary: You know some things that run through my mind are starting a sports league that doesn’t exist, starting a vodka/wine/alcohol brand, starting a candy or snack brand, starting a fund, starting an incubator that builds companies and ideas that I have in my mind – there’s places to go.

Jordan: Awesome – very exciting. I’ve got a final question for you. A lot of my readers are just getting started online. Most of them are either in college or working careers and they just getting started with blogging or video blogging. A lot of them have just bought their domain names, just installed wordpress so the paint is still wet. What type of advice do you have for these people trying to get started, trying to brand themselves online and start an online business.

Gary: Work every hour that you possibly can and distribution, distribution, distribution. What I mean by that is go to blogs and answer their questions, ask people to reblog your stuff, write for other websites for free, get your name out there, distribution, distribution, distribution. Do what you’re doing right now which is interviewing somebody that’s got more internet fame and then leverage their name to get more people to know about you. It’s the same old. Build awareness – it matters.

Jordan: Awesome! Gary Vaynerchuk, thanks so much taking the time to speak with me. Big fan and even these 17 minutes I know is a lot for you. So thanks again. So best of luck to everything you’re doing in the future and hopefully our paths will cross again.

Gary: I hope so man, hopefully at an AFC championship game in New York.

Jordan: I hope so. I would fly back from Budapest to be there.

Gary: I love it. Good luck to you and take care.

Jordan: You as well! buh-bye!


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