Gary Vaynerchuk: Cover boy for the American Dream

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He also fostered relationships with various CEOs and investors such as Kevin Rose, Travis Kalanick, Ev Williams and Mark Zuckerberg. These connections led to Gary’s first forays into angel investing, with early involvement with companies like Twitter, Facebook and Tumblr. During this time, Gary also embarked on what would become a prolific career as a public speaker.

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Photo: Ken Yeung/VentureBeat

Gary and his brother AJ founded VaynerMedia, an agency focused on helping large brands tell their stories on social media. Securing early clients like the New York Jets and the NHL allowed them to scale at a rapid pace, and it now represents Fortune 500 clients General Electric, Anheiser-Busch InBev and Pepsi.

But the wine, the thing that – along with baseball cards – got him started is never far from his thoughts. In typically blunt mood he says: “There’s always a wine bully. The one person who did read the ‘Wine Spectator,’ who tells you what to drink and why the ’97 is better than the ’98. I want to punch the wine bully in the face. I want to make sure this generation of wine drinkers isn’t elitist and snotty. I want it to be about family and bringing people together.”

He has since launched the highly succeful #AskGaryVee Showand and has  partnered with Matt Higgins from RSE Ventures to form a $25 million investment fund focusing on first round financing and incubation.

Gary Vaynerchuk builds businesses… Fresh out of college, he took his family wine business and grew it from a $3 million to a $60 million business in just five years. Asked how he did it, he said: “My store, Wine Library, outsells big national chains. It started with hustle. I always say that our success wasn’t due to my hundreds of online videos about wine that went viral, but to the hours I spent talking to people online afterward, making connections and building relationships.”

VaynerMedi is one of the world’s hottest digital agencies. Along the way he became a prolific angel investor and venture capitalist. Keep moving but stay in it for the long-term appears to be the message. “So many business fail because they are not playing the marathon. They’re playing the sprint. They’re not worried about lifetime value and retention. They’re worried about short-term goals. People don’t want to embrace culture shifts because it’s not going to happen in the next 20 minutes.”

Final word from Gary Vaynerchuk who builds businesses: “People are chasing cash, not happiness. When you chase money, you’re going to lose. You’re just going to. Even if you get the money, you’re not going to be happy.”