Gary Vaynerchuk: Cover boy for the American Dream

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While at college, Gary discovered the internet. He immediately saw the potential to “sell shit” and set about convincing his father to let him have a website built for Shopper’s Discount Liquor. And so, winelibrary.com was born. He appears to still have family firmly at the centre of what he does. “The chef that grew up with the grandma who cooks tends to always beat the chef that went to the culinary institute. It’s in the blood.”

Over the following years, Gary would make it his mission to be a first mover wherever he could see sales opportunities: from email marketing, to Google AdWords to flash sales. This approach dramatically increased sales, driving – the now rebranded – Wine Library from $3 miilion to $60 million sales in just five years. On branding, he says: “You have to understand your own personal DNA. Don’t do things because I do them or Steve Jobs or Mark Cuban tried it. You need to know your personal brand and stay true to it.”

He then decided to pursue a new avenue of content marketing, making his foray into creating video content. It changed his life forever. You can see the common denominator here: keep on the move. But he puts it down to something more old-fashioned: “One of the things that I’m really proud of,” he says, “is that I have really good timing. It’s very easy for me to see what’s coming up, and it’s no coincidence that I went headfirst into wine and then headfirst into new media– none at all.”

His YouTube vlog called Wine Library TV show featured wine reviews and advice on wine appreciation in Gary’s down-to-earth, bombastic style. Episodes consisted of wine tastings along with other wine related topics and were produced at a breakneck speed of one 20-minute episode per day. The show eventually reached cult status, and he became “the internet wine guy”. His appearance on Conan O’Brien launched Gary into the limelight. Wine Library TV ran for 1,000 episodes before Gary decided it was time to end the show.