Is Gary Vaynerchuk for Real?

December 8, 2014, 7:49 PM UTC

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, 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.)

Along with the books came speaking engagements, still a staple of his schedule today, at which he preaches the gospel of self-branding to sellout crowds with a no-holds-barred flair that delights some and offends others. In a Q&A after a talk at the 2011 Inc. 500 seminar, when Vaynerchuk was promoting the give-and-take concept of his book The Thank-You Economy, a small-business owner in the audience asked, in an attempt to follow Vaynerchuk’s own instructions about making an ask of someone, “Would you mind tweetin’ about [my company] to your 900,000 friends?” The audience laughed and applauded, but Vaynerchuk shut him down: “Good hustle… but see, what I find interesting is, even though I just gave a really passionate talk, you went for the 19-year-old dude move. You tried to close on our first transaction. And so that gives you a big fucking no… You fucking blew it… Next time you go into the social media bar, don’t be a douchebag, roll deep.”

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.”

Becoming a social media guru and self-stylized branding expert (of which there are now hordes) led to riches and renown, but also the aforementioned criticism. The Wall Street Journal called him “continually overexposed.” The New York Times called him a “tireless self-promoter.” (Even internally at Fortune, in brainstorm meetings discussing candidates for our annual 40 Under 40 list, initial mention of Vaynerchuk yielded eye-rolls.)

Nonetheless, the notoriety served as a steppingstone to launching VaynerMedia, a digital agency, with his brother AJ in 2009. “Vayner,” as employees and industry peers call it, advises brands on Vaynerchuk’s field of mastery: how to take advantage of social media. While big PR agencies have long offered social media as one of many services, Vayner focuses on it, counseling clients to shift much more of their marketing budgets to social media efforts. That argument has wooed big Fortune 500 names like GE, Anheuser-Busch InBev, and Unilever.

Vaynerchuk believes VaynerMedia’s success has also helped change the minds of some of his critics. “I’m excited because this company has completely confused the market,” he says. “When I first started it, everyone was like, ‘Oh, Mr. A-lot-of-Twitter-followers thinks he can compete in this world.’ And we’ve not only competed, we will be considered a new standard.” He compares his firm’s potential to other big marketing agencies like AKQA and Digitas: “We’re going to be that, for the social generation. We are the winner of that game.” And, he points out—albeit in trademark GaryVee language—that this side of his story has nothing to do with his persona or charisma: “I’ve put my head down and I’ve grinded the shit out of it operationally,” he says.

Industry peers at other agencies don’t necessarily agree that VaynerMedia is a new paradigm. Curtis Hougland, founder of digital marketing agency Attention, says that more and more brands these days are skipping the agency model and taking their social media marketing in-house. Many that do hire firms like Vayner, he says, do it out of fear—they don’t quite “get” social media marketing, so they just farm it out. But Hougland also gives Vaynerchuk a lot of credit. “He has to be loud to stand out, and he’s not wrong to do that,” he says. “He represents shameless promotion, the guy who will say the things that you might hesitate to… But that’s really, really popular, and it’s easy to understand. It’s like pop music.”

An executive at another rival digital agency, who wished to remain anonymous, thinks a big part of VaynerMedia’s draw is the mystique around Vaynerchuk: “It’s like people who go to see a fortuneteller,” he says. “They walk out saying, ‘Oh my god, I believe.’ Because they walked in wanting to believe.” And he wonders if the guru gets in his own company’s way: “If I’m a client, I’m like, ‘I’m paying you to run my brand, but you’re also busy elevating your brand, and writing your books.’”

B.J. Mendelson, a fellow Internet personality and a vocal critic of Vaynerchuk, says his main complaint—one that has been raised by others—is the potential conflict of interest created by Vaynerchuk’s personal technology investments. He was an early investor in Twitter, Facebook, and Tumblr (as well as Birchbox, Circa, HubSpot, Uber and Quirky, all household names) and now runs a digital agency that urges brands to utilize those platforms. To be fair, those are the same obvious platforms any digital agency would advocate for. But Mendelson sees it as disingenuous. “This guy is peddling stuff he has an interest in,” he says.

Vaynerchuk has heard it all before. He says that all clients are made aware of his investment interests. And besides, he reasons, these companies are at such a huge scale that VaynerMedia’s involvement is not going to affect them much one way or another. (Moreover, what social media consultant would not suggest having a brand presence on Twitter and Facebook?)

And he insists that VaynerMedia is bigger than just him. He says many of the young applicants that come in for job interviews haven’t heard of him at all when they apply. Besides, it’s difficult to believe that mystique alone has drawn not only Fortune 500 corporate clients but also 420 employees to come on board.

One thing that’s indisputable is that Vaynerchuk’s personality infuses the strong culture at VaynerMedia. A wall of the New York offices reads, “We love social media because it sells shit.” Employees refer to the CFO as the “CFBro.” In one corner is a vending machine with Vaynerchuk’s face on it, labeled “Gary Venderchuk.” There are knick-knacks and tchotchkes all over the place, and the majority of employees, more than half of which are millennials, do not have designated desks—they shuffle around every day. (The New York employees will eventually relocate to Hudson Yards, where VaynerMedia has just purchased 90,000 square feet of office space.)

And while many of VaynerMedia’s employees work like traditional agency folks, managing accounts for brand clients, a number of them work exclusively for Brand Gary, as opposed to the agency. At the office in New York, Vaynerchuk sits in a glass-walled room where he has people filming him throughout the day. It feels almost like a Damien Hirst installation. One of his team members, Steve Unwin, describes his own job thusly: “I touch all of Gary’s content—not the tweets, he does that himself, but the longform stuff, the blog posts. I tend to translate him into English.” Another, Mike Boyd, left the company to start his own music management company but still does paid work in the music business for Vaynerchuk, who is also now an investor in his company. Boyd says he was originally hired “specifically to build relationships in the music industry for Gary.”

Many of those relationships are beneficial to Vayner clients. Boyd helped hook up Avion tequila, a VaynerMedia client, with Young Jeezy, who has pumped the brand on social media. And Boyd says that when his own client Rome Fortune, a budding rapper, “becomes the next big artist brands want to get to,” VaynerMedia’s clients will have the first crack.

More generally, Vaynerchuk dismisses the refrains of his haters simply by saying his track record speaks for itself. And it does. With one $60 million-in-sales company under his belt, and now another that is approaching the same size (VaynerMedia says it did $23 million in revenue in 2013), he reasons that he is someone who has “done it,” rather than talked about doing it.

“When I’m put in the ground, what I’ll feel good about is the two businesses I made,” he says. “Show me who else did that.”

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