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The judges of the 88th Miss America pageant, which was held last September in Atlantic City, were mostly names you know, people of considerable fame. They included former supermodel Kathy Ireland, NFL great and Dancing with the Stars winner Donald Driver, and Olympic gymnast Shawn Johnson.

And then there was Gary Vaynerchuk. When ABC’s host Chris Harrison (of Bachelor fame) introduced him—“an entrepreneur, author, and social media master”—Vaynerchuk held up his phone and mimed the act of taking a selfie.

It was a perfect (and perfectly predictable) joke at his own expense. Vaynerchuk has created two successful companies; he is a bestselling author; he can command six-figure fees for speaking engagements; and he has 1.1 million Twitter followers. But he is largely unknown to the American television-viewing public. Rather, he is Internet famous. That fame happened by design and by years of meticulous planning—and it has drawn vocal critics for a style that is loud, bombastic and blatantly self-promotional. (A sample exhortation from a video commanding people to subscribe to his YouTube channel: “Fucking follow me, right now.”)


A common line of criticism against Vaynerchuk is that he is a snake-oil salesman, one of a growing number of Internet celebrity marketers who make their money telling eager beaver entrepreneurs that they, too, can get rich and famous by self-marketing on social media. “People think I’m a hack, simply because a lot of people that were early to social media really were hacks,” he told Fortune, sitting in the casino at the Borgata Atlantic City on the second night of pageant preliminaries in September. “And I get lumped in with them. But when someone says to me, ‘You’ve only achieved this because you’re big on social media,’ I say, ‘want to see my calendar?’”


He pulls out his phone to prove it. The calendar for the next few weekdays is jammed with meetings, meals, or phone calls—some of them one-on-one talks with colleagues, many of them fancy dinners with tech exec pals—and nary a 20-minute block open. He has a meeting scheduled for 11:30 that same night with a team of his employees, after our interview and after hours of judging the pageant prelims. “It comes from straight-up immigrant fucking hustle,” he says.

But every CEO is busy. What makes Vaynerchuk fascinating is the disparity between Gary, the person, and GaryVee, the Internet persona—and the passionate reactions to the latter. The Web made Vaynerchuk, but his bluster on the Web also made him a lightning rod. A 2009 Gawker headline called him a “wine-loving Twitter twerp,” and this year its tech site Valleywag wrote, “Think of him as a sort of Deepak Chopra of selling bullshit with Snapchat.”

When he discusses his detractors, Vaynerchuk can sound like Rodney Dangerfield bemoaning the lack of respect. And yet most of the insulting tweets you find about Vaynerchuk also begrudgingly give him credit, like @BMilneSLO in 2012: “@garyvee you’re still annoying… and obnoxious… but you’re right,” or @AndersRiis the same year: “this bloke is a bit annoying to listen to, but he does have valid points on social media.” Those who complain about him tend to overlook the fact that he is already in his third—maybe fourth—successful act in business. And if the quick growth of his latest venture is any indication, the joke may be on everyone else.

Gary Vaynerchuk was an entrepreneur well before Twitter came along. The story is well known to those who have followed his rise: Born in Belarus, he came to the U.S. in 1978 with his parents. Raised in Edison, New Jersey, he moved back home in 1998, after college at Mount Ida in Newton, Mass., to work at his father’s liquor store in nearby Springfield, which bore the unsexy name Shoppers Discount Liquors. It was an all-purpose, everyday liquor shop, like any other, but it would serve as the blank canvas for a grand experiment that would become Vaynerchuk’s talent: harnessing the Internet to build a brand.


“I know exactly when I found out about the Internet,” he says. It was 1994 and he was a freshman in college. “I was like, ‘Wait a minute. We don’t need 8,000 liquor stores. I can just build this.” Three years later in 1997, while still in college, Vaynerchuk launched WineLibrary.com, which was one of the first wine e-commerce businesses. Most wine shops didn’t yet know what the Web was for, much less sell their wares online. His father gave Gary an ad budget as well as “enormous freedom,” says Vaynerchuk. (In turn, they later renamed the store Wine Library.) Gary took advantage of new tools he had learned about, like then-burgeoning Google AdWords (which let him pay for his site to appear against searches for “wine”) as well as more traditional print, TV and radio advertising to grow the shop’s annual revenues from $3 million to $45 million by 2003.


In 2006, his career took a now well-chronicled turn. Vaynerchuk launched Wine Library TV, a bare-bones web video series in which Vaynerchuk tasted and discussed wines, spitting into a New York Jets bucket. (He is a diehard fan and talks often about his ultimate goal of buying the team.) With a shaky camera and casual feel, its sole attraction was Vaynerchuk, hamming it up, blurting non-sequiturs and gesticulating wildly. The show soon went “viral,” before the term became ubiquitous, drawing 100,000 views per episode at its peak. He invited guests, ranging from no-name wine experts to celebrities like Wall Street pundit Jim Cramer and hockey star Wayne Gretzky. Some in the wine world accused him of dumbing down the art of wine appreciation, but Vaynerchuk responded that he was creating new oenophiles.

Three years in, Wine Library TV was as much about Vaynerchuk as it was about wine. (The opening animation showed the pouring of a bottle labeled, “Vaynerchuk: a fine New Jersey cabernet.”) He was dispersing wisdom on much more than wine: topics like branding, career advice, and shaping an online identity. And his following on a still-nascent Twitter had grown, reaching 145,000 followers by 2009, when the service was just three years old. He had drawn so much media attention that in the same year, he inked a seven-figure, 10-book deal with HarperStudio to write business books with motivational titles like Crush It! and, Jab, Jab, Jab, Right Hook. (The HarperStudio imprint has since folded, so Vaynerchuk’s fourth book, in early 2016, will be published under Harper Business.)

Vaynerchuk ended Wine Library TV in 2011 but now films regular #AskGaryVee videos (he’s up to 50 and the series just started last August) in which he answers questions (from, where else, Twitter) about career advancement and brand-building on social media. He makes other short videos and posts them to YouTube and Facebook. (One in 2012 criticized the OWN network, which asked followers to retweet an Oprah hashtag, for, “continuing to think that these [social] platforms are [there] to push down the throat of the consumer.” Nevermind that this is exactly what Vaynerchuk does.) He has 46,000 followers on Instagram, where the vast majority of his posts are selfies or selfie videos. He writes super-short posts for the blogging platform Medium (in which he is an investor) each week, with headlines like, “Some solid fucking advice,” and, “Nobody cares about your billion-dollar idea.” He posts earnest, yet shameless traffic pleas to Facebook like this one, from November: “Curious question—are you sub’d for my YT channel? If not would mean a lot to me.”