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Case of the Fridays – CEO, Entrepreneur, and Media Expert Gary Vaynerchuk

Preface – I first read Gary’s book Crush It back in 2010.  He wrote about how someone can concentrate on what they love – even if it’s Duck hunting, underwater basket weaving, or the 1980′s show Alf – and make a living through blogging about the topic.  The book inspired me, and I’ve since followed several of his online channels to listen to and engage with his content.  He continually motivates me to take a critical look at social media and how it can best serve my business, and is one of the few people I’ve really found to be inspirational in regards to my career.  Here’s a quote from him that I feel hits the nail on the head:

A few people had asked me about how I was able to reach Gary for an interview.  Well, at the beginning of the year – he announced that he would be doing a series of 15 minute interviews for blogs and radio shows.  His company sent out an email announcement and I jumped on it.

I heard back a few days later requesting the interview date to be set in late August.  His schedule is extremely busy, and I had no issue with it.

His content has been responsible for motivating me to have such a go-giver attitude in regards to my business, and his ideas have helped shape my perspectives in relation to technology and social media.

Unfortunately, we weren’t able to do the interview in-person, but I was able to chat with him on the phone yesterday and have dialogue about my questions.  (I’ve gotten responses from others stating they would fill out an email response, but I feel that an actual conversation is so much more genuine and less structured – so I passed for the time being.  It’s important to keep things *real*.

So with that, let’s get to the interview!


First off I’d like to say thank you – you’ve been a true inspiration to me. Your books have had a huge impact on how I approach business and relationships, and I attribute a lot of my success to your teachings.  As a matter of fact, this feature (Case of the Fridays) was inspired by your book Crush It.  It really drives me to see people pursuing their passions, and I’m happy to pass along the favor to those that are interested in making the leap.


Thank you man, that makes me super happy.


What is your name/age?


Gary Vaynerchuk, 37


What is your occupation?


Co-founder and CEO of a social media brand consulting agencyvideo blogger, co-owner and director of operations of a wine retail store, and an author and public speaker on the subjects of social media, brand building and e-commerce.


Where did you grow up?


Edison, New Jersey


What level of schooling have you completed?


Junior College


How long have you been doing what you currently do?


I’ve been a hustling since I ran lemonade stands as a little kid…driving around on my big wheels collecting money from my friends who were running it in different neighborhoods for me.


What is it that you love about your work?


The control.  I love the fact that I’m pretty in-control and that I’m the boss’ boss.  I like the fact that I’m the one that makes the decisions – what I want to do, how I want to do it, and how I want to go about it.  I would say that the control of my destiny is something that is very, very attractive to me.


What is your least favorite thing about your work?


I think that I just love to work so much that it draws me away from my family – who are also so important to me.


Yeah I actually read your post the other day about how your ‘best mistake you’ve ever made’ was working too much – how do you decide where to draw the line when it comes to choosing between an important family event and an important business opportunity? 


Well, I don’t really have a one-size-fits-all answer for you there – of course there are some promises and occasions that I wont miss like birthdays or anniversaries or big holidays – even if it was for the biggest business opportunity of all time…but I think you really have to address each circumstance on a case-by-case basis.


What are your top priorities in the ‘big picture’?  Is it financial success, influence, legacy…to buy the jets?


Having the at-bat to buy the Jets is just as good as actually buying them, haha.  And that is one of my goals, sure.  But I mean – look at where we’re at right now – I wrote a book and see how much that has impacted your life?!  That’s insane.  Do you know how I feel right now after you had made that opening statement??  That makes my head explode.  And I’m really just addicted to the appreciation that I hear from people.


Recently you put out a suggestion to people to ask their audience how they can be of service to them – I saw that some guy joked about getting a double cheeseburger and then posted a video when you actually sent him one.  What has the response been like to this?  What kind of feedback have you gotten from people?


Well, I did a spreecast the other day and got a lot of positive feedback from people that had actually taken it to action.  I, myself, experience GREAT results whenever I do it.  It’s something I’ve been doing for awhile now, but it’s just something that I’ve been ‘talking about’ more recently.  I really believe in the idea, and I think that by giving back – it’s a great way to lead a great life – and also have great business results.


You do quite a bit of traveling for your speaking engagements.  I think there are a lot of entrepreneurs out there that have ambitions to pursue that route in their field – are there any downsides or disadvantages that people might not know about that you’d be willing to share?


I think the cliché downsides of speaking gigs that everyone kind of anticipates are well known – the jet lag, the change in time zones, the airport food, the grind of always being up…but it’s all greatly off-set by the financial benefit and the admiration that comes from it.  It’s like a drug.  It’s hard work and it’s not as easy as it sounds, but that just comes with the territory.  It’s kind of like being an athlete or a pop-star…life on the road is hard work.


What has been the biggest challenge of your career?


I would say that I always want to bite off more than I can chew.  It’s difficult to maintain a solid structure between my ambition and my appetite.


I think I remember awhile back you mentioning the importance of learning how to say “no” to opportunity and the downsides of being a “yes man”.


Yeah man, it’s a huge struggle for me.


Do people ever say negative things to you in response to your videos or blog posts that make you want to stop producing content?


Yeah of course people can react strongly to my content – but I’m aware how I can come across at times and I’ve gotta respect that.  It really just makes me aware of how I’m different.  And as a matter of fact, it’s shocking to me at how little I get despite how outspoken I am and how “Jersey” I am – I really don’t get much at all compared to others at similar levels.  I really don’t like cynicism – I hate it, but I definitely use it as motivation to prove them wrong – to go to higher levels.


If someone were graduating college or switching careers to something they’re passionate about, what would you suggest to them to start on the right path?


To find an organization or a team that they want to be involved with, and offer to work for as little or as-close-to-free as possible.  Because the access is much more valuable than the short-term money.


If you were 20 again, is that what you would do?


Well in my case I was working with our wine company at 16 and I was already in love with it.  But if I didn’t have that and I was fresh on my own – 100% without a doubt.  If I wanted to be a lawyer, I’d go and intern at a law firm for free – the best one that I could get toand then just hustle 17 hour days until the right person noticed.  Because that’s how things work.


Do you think a lot of people feel held back because of money to do something like that?


Oh of course.  They need money for the short term – they have loans to pay, they can’t afford it, it’s just not practical.  But most people – when it comes down to it, they just don’t want to do itThey’ll jump on an opportunity to make 40 or 50K instead of putting in the hustle to work with something that’s going to benefit them ten-fold in the long run.


Does that come across as lazy to you?


No, it’s just that this approach – or this story – is not one that’s commonly told.  A lot of people get advice from their parents or teachers telling them to go to grad school or get ‘paid’ internships and that they should ignore the free ones.


For the bigger dreams – if you want to be “Puff Daddy” when you grow up, you need to go and work for Puff Daddy.  You need to figure out whatever it takes – email or call repeatedly and offer to work for free in order to get your foot in the door.


So, find some way to bring unique value to that person or organization?


Exactly.  Show them you can be truly helpful and proactive.


So, how would you suggest that someone sustains themself to be able to pursue such opportunities?


If you’re 18-25, get 6 roommates.  Work at 7-11 at the graveyard shift after you’re finished at your real job.  It really all depends on how bad that person truly wants it.  Truth is, most people don’t want it as bad as they say they want it.


So who has inspired you along your path?


My parents.  They’re the ones.  Nobody else.





What are some of your favorite sounds?


My favorite sound in the world is the Jets chant you hear when you’re in the stadium.  Also, my little girl’s laugh – some of my friends’ laughs are hilarious.  People with different kinds of laughs are great.


What are some of your favorite smells?


White and Red wine of course.  I love the smell of barbeque, a pack of 1987 Huff Baseball cards freshly opened.  I also love the smell of burnt BMX bike tire on pavement.  Comes from when I was growing up – we’d all just ride around and skid out.


What did you get into the most trouble for when you were young?


Report cards.  I was good with everything else, but I always got in trouble for getting F’s.


What’s your favorite quotation?


I’m not really much for quotations – but the only one that’s really caught my eye…that’s really stuck with me was from Jay-Z.  His quote, “I’m not a businessman, I’m a business, man.”


Is that why you have him on your instagram profile picture?


Ha!  Yep.


Is there anything I can do to help you out today?


Uhh, yeah.  I’m really trying to push sales for Jab Jab Jab Right Hook – if there’s anything you can do…buy a couple pre-sales, maybe give one away on your blog-


I actually bought 5 pre-orders on Amazon yesterday, along with a couple Crush It’s for some friends because I love that book so much.


Awesome.  Thank you so much.  Thank you.


Now I’m wondering…what would it take to get an autographed version of Crush It?  That’d mean a lot to me.


Email me.  We’ll send it out to you next week.


Awesome.  And just one last favor to ask – I usually like to post a photo for people to have a visual of the conversation going down between us on my blog…do you think you could do me a huge favor and just send me a mobile pic once you’re off the line?


Sure man, no problem.

Gary Vaynerchuk Blog Interview


And here’s one of me in turn.



Hope you enjoyed the interview.  If you found it valuable, and think others would too, I’d love it if you’d share this.

And if you’re a big fan of Gary, or even if you’re not just yet – I’d suggest getting a copy of his new book coming out this fall.

Christine McDannell - Loved everything he said in this interview! Great questions, Tim. Especially enjoyed how much he preached “Hustling” AKA: Work for free to get your foot in the door and really prove yourself and work your little a** off. Such amazing advice and I am afraid some people think it is just “luck”.August 30, 2013 – 12:37 pm

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