Gary Vaynerchuk, the Oeno-trepreneur

“I think wine really needed me,” said Internet sensation Gary Vaynerchuk on a recent Monday at T Bar steakhouse on the Upper East Side, near the apartment he shares with his wife. “I think it’s way too snobby and elitist in this country, and I don’t think wine wanted to be positioned that way.”

He was sipping a glass of 2005 Flowers Pinot Noir from the Sonoma Valley. “I’m really in an anti-Pinot Noir ordering mode, ’cause everybody’s on it,” he said, before asking the waiter for a decanter, “but it was by far the best wine on the list.”

Mr. Vaynerchuk, 32, has styled himself as the leading grape guru of the Internet, with a wine-tasting video blog, Wine Library TV, whose viewers, or “Vayniacs,” average 80,000, he said. Taped out of his family’s massive wine store in Springfield, N.J., where he is director of operations, a typical “Thunder Show” runs 20 minutes and includes exhortations to try new varietals, trust one’s own palate and ignore “wine bullies.” Not that Mr. Vaynerchuk lacks for aggression. On a given program he might shout, gesticulate, spit into a Jets pail, hype the NFL draft, issue frequent shout-outs to the “CKCs,” i.e., “College Kid Crowd”—“Woop! Woop!”—and describe wine as “a little bit like mayonnaise; hot jam reduction meets gasoline body shop meets mayonnaise” (a Jean Luc Colombo Cornas) or “a little garbagey; I’m talking like New York City garbage” (a 2005 Ridge Lytton Springs Zinfandel).

Recently, Mr. Vaynerchuk appealed to the Vayniacs to help make his first book, Gary Vaynerchuk’s 101 Wines Guaranteed to Inspire, Delight, and Bring Thunder to Your World (Rodale) a success. The book isn’t officially published until May 13, but “I wanna stun the world, that’s how I roll, so I need your support,” he told his audience. They responded by catapulting it to No. 36 in presales on Amazon.com. Their pedagogue proclaimed himself humbled, but not surprised. “I just had this crazy gut feeling that everyone was going to buy it as a thank-you,” he said, “because they’ve gotten so much for free.”

Chat about Chateauneuf-du-Pape

By the time Mr. Vaynerchuk met The Observer at the steakhouse, his book was languishing in the 180-300 range, where he was monitoring it obsessively. He has continued to appeal to the Vayniacs on Wine Library TV and on the seven social networking sites he uses, including Facebook, Twitter and MySpace, to help it rebound. His zeal on this matter bordered on the religious. This was not just about book sales, and it was not just about wine.

“I have something very special to share with the world, and honestly think it comes from a very good place,” he said. “When I found out about The Secret”—the cult self-help book that asserts the universe is yours for the taking, if you just have the right attitude—“it pissed me off. Shit, that was the book I should have wrote! Because I believed in it my whole life. … I don’t wanna come off cocky, but I know I’m going to achieve staggering accomplishments.”

Smaller in stature and softer in affect than he appears on his program, Mr. Vayerchuk was wearing an untucked, oversize striped Ted Baker oxford-cloth shirt, not unlike the ones worn by 20-something traders to bars in Murray Hill. “I love this shirt,” he said.

Mr. Vaynerchuk was 3 years old when his parents immigrated to Queens from Russia with him and two younger siblings in 1978. His father began working at a wine store in New Jersey in 1980, eventually opening his own store, Shoppers Discount Liquors, in Springfield in 1983. The young Mr. Vaynerchuk began working there on weekends and over summers at age 15.

“I hated it,” he said. “I had a very successful baseball-card business at the time. I was selling, like, $1,000 dollars worth of cards every weekend.”

Then he realized that people collected wine, too. He began reading Wine Spectator cover to cover. By the time he was 22, the younger Vaynerchuk said, father had all but surrendered day-to-day operations to his son. Gary grew the business from $4 million to upward of $50 million between 1998 and 2005, he said, with aggressive pricing and a Web site and e-mail list before such things were common. Also? “Working my face off,” Mr. Vaynerchuk said. “I was on the floor, I made personal connections. I didn’t pay myself a lot of money.” They changed the name to Wine Library, and the store stopped announcing sales.

He met his wife, Liz—who is now starting her own Internet venture, a gossip blog—on JDate when he was 28 and “petrified that I’d never get married ’cause I worked every hour.” He said he knew on their first date, at Jonathan Waxman’s now-closed Washington Park, that she was the one, partly because her brother worked for the Jets.

Then, on Mr. Vaynerchuk’s 30th birthday, he had a “freakout.”

“I had this feeling, like I could do something bigger,” he said. Inspired by “vloggers” like Amanda Congdon and Ze Frank and the viral success of “Lazy Sunday,” the Andy Samberg faux rap video from Saturday Night Live, he launched Wine Library TV in February 2006. “I thought, ‘You know what? Video on the Internet is ready.’” Recently, Mr. Vaynerchuk posted his 457th episode of the show. He answers between 800 and 1,200 e-mails per day and keeps 7,000 fans abreast of his thoughts and movements via the burgeoning mobile status-updates site Twitter.

“OMG I just signed onto Facebook and WHAM! 49 peeps wanna chat in 34 seconds, WILD!” he wrote on April 23rd.

When Mr. Vaynerchuk is not interacting with fans online, he is traveling to meet them in person at speaking engagements, for which he commands “a solid five figures,” he said. “Inevitably everybody’s so fascinated to meet me in the technology sphere, ’cause I’m really winning, and people are like, ‘What the hell? He’s talking about wine and everybody’s loving it.”

Despite the fact that he’s unapologetically marketing himself to the middlebrow, Mr. Vaynerchuk is beginning to be recognized in the most elite wine temples of New York, like Encore, the new Alain Ducasse place at the St. Regis, and L’Atelier de Joel Robuchon, where he said several of the staff had approached him as fans. “People that have the skills—the chops—know that I really know what I’m talking about.”

“He’s made a huge impact on the industry, not only on a regional level but across the country,” said Brett Feore, the sommelier and wine buyer at BLT Steak on 57th Street and a friend of Mr. Vaynerchuk’s. “I don’t think anyone’s ever done what he’s doing. It makes somebody that wasn’t savvy the day before, savvy.”

Tim Kopec, sommelier at Veritas, has been purchasing wine for his personal use from Mr. Vaynerchuk for years. “He’s a force in retail but he’s on people’s radar because he has pursued very hard his persona,” he said. “Gary’s a very smart guy, and he’s very witty, and he’s very quick, and he can talk to a brick wall. And if he has to go onto Conan O’Brien and pound dirt in his mouth, he’ll do it.” (Mr. Vaynerchuk appeared on Mr. O’Brien’s show in August ’07, and will again May 12.)

Mr. Vaynerchuk speculated he could increase his demographic multiple times over—“maybe I’ll lose some of the rad kids but I’ll pick up every wine person in America”—by wearing a suit and tie and choosing a plusher setting. “But it’s not all the way me,” he said, “and I’m just not willing to go there.”

He’d been nibbling salmon and Caesar salad and mostly ignoring his Pinot. “I’ve probably only been drunk like twice in my whole life. I am not a big drinker at all.”

Mr. Vaynerchuk copped to some social anxiety. “I am fundamentally terrified and hate being disliked by anybody,” he said. “My entire life goal is to meet every person on earth, because that way I will never be misunderstood.” That, and to own the New York Jets, he said. He wasn’t kidding about this.

From Cabernet … to CAA!

Before an early-morning taping of his show at Wine Library in suburban Jersey on April 23, Mr. Vaynerchuk was standing in his office, surrounded by Jets paraphernalia. When a visitor inquired as to the meaning of “Broadway Joe,” which was scribbled across a photo of the famous quarterback Joe Namath, Mr. Vaynerchuk responded with a pitying stare. The signed footballs and framed photos and jerseys leaning against the walls gave the office the appearance of a sports bar undergoing a renovation.

Mr. Vaynerchuk was quiet, tired. He’d been up answering e-mails until 4 a.m. the night before, he said. But after his cameraman set up, the wine expert came to life and began shouting. “Today we’re at 445,” he told the Vayniacs of his book’s current position. “Yesterday we had a little bit of a push and we were in the 200’s!”

He went on to sample four wines that cost less than $10, an idea he got from the last e-mail he read before the taping. “I’m not feelin’ this wine,” he said of a Cabernet Sauvignon called Evil. “It’s just like you know how sometimes people wear outfits they shouldn’t? The fruit is unable to contain the alcohol, so it’s bursting out of the seams.”

He admitted afterward that the shouting was often to get his own attention as much as the attention of his fans.

“I want it all,” he said. “I don’t understand why people don’t feel they can have it. I want to be happy every second. And you know what else? I want to make other people happy every second.”

Since September 2007, Mr. Vaynerchuk has been represented by Creative Artists’ Agency. “Which is completely obnoxious,” he said. “These are the people that represent Derek Jeter and Oprah and Peyton Manning. I feel like I’m that character from Sesame Street, remember that skit, ‘One of these things don’t look like the other?’

“I’ve been offered a good 50 to 60 television deals,” he said. “And of course I always hold out, because if I make that leap to television I want it to be sick. HBO, Bravo, Showtime.”

Recently he spoke at a Facebook conference on wine and social media in San Francisco. The company’s young founder, Mark Zuckerberg, later approached him and took him out to dinner.

“We are in the fundamental gold rush of personal branding,” Mr. Vaynerchuk said at T Bar.

And would his vehicle have been something else if not wine?

“I’m not going to sit here and say no.”

On the May 2 episode of Wine Library TV, Mr. Vaynerchuk’s trademark introduction took on an unusually philosophical tone. He was seated on the brown leather couch overlooking Wine Library’s parking lot, a stack of his books on the table. “I am your host, Gary VAY-NERCHUK!” he began, with typical relish. “And this, my friends, is the Thunder Show: The Internet’s most passionate, thought-provoking, gosh-darn-it best wine show there is, and that’s because we continue to expand the palate, try different things, love our families, do the right things, answer our e-mails, whatever it takes, because we are on this mission to change the wine world!” He had an earnest, pleading, almost vulnerable tone.

He gave a shout-out to “Jade, my favorite little Starbucks barista,” and then to his mother.

“Happy birthday, Mommy, I love you with all my heart, I can’t wait to spend the whole day with you tomorrow.”

Mr. Vaynerchuk’s book tour will last “almost all summer,” but first, he is taking his wife to Turks & Caicos shortly after the publication date. “I owe that to Lizzie, right?” he said. “She’s got big-time patience and gets the big picture. I don’t think you can—I don’t want to say this because it’s obnoxious, but I’ll say it anyway—I don’t think you can hang with me for a long time without realizing I’m up to something big, so imagine living with me. Something’s happening, and it’s not small.”

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topics: Gary Vaynerchuk