Very good year for wine expert building online empire

On tens of thousands of computer screens around the world, wine expert Gary Vaynerchuk sits with a fine Riesling and - a bowl of Cap'n Crunch.

He's dealing with that burning question: Which wine pairs best with breakfast cereal? And he has the answer.

Vaynerchuk's story is a story of this very moment. The Springfield, N.J., wine retailer's book, Crush It!, published last week, is the first in a 10-book deal, signed for a reported seven figures. His is an immigrant's story, a social media story, an Internet success story.

"I have that tastemaker gene," he says, "that's always going to be a key component to my success."

It's also a story of change in the book business, as publishers ransack social media to find products for hungry (or in this case, thirsty) readers. Vaynerchuk is one of a growing number of stars who became famous via the Web, then crossed over to media such as TV and print.

"Definitely, we all are watching social media and blogs," says Kate McKean, literary agent at Howard Morhaim Literary Agency Inc., in New York. "We're looking for strong voices, and the strong voices are on the Internet."

Vaynerchuk, 33, is calling from his father's wine shop, Wine Library in Springfield, where he's co-owner and director of operations. But such is his fame that "I get here only once a week most weeks. I live in New York, and it's not that far away, but it feels like I'm away at summer camp."

In 1996, he took to the Internet and started building what would become WineLibrary.com, about the store's offerings. Even then, he says, "People didn't understand, but I knew it was going to be the way the world works."

Vaynerchuk is voluble, verbal, and totally positive. The impression is not of egotism but happy confidence. Somehow he's most winning when speaking of his pleasure in being himself. "People who don't like me at first because of my brashness or bluntness," he says, chuckling, "eventually will like me."

He could have done pretty well with the wine shop and Web site. But then came 2005, year of the video blog, year of YouTube, year of sites such as Ze Frank and Rocketboom, where daily video bloggers built big audiences and, far from the mainstream, found world Web fame.

Vaynerchuk loved it. "I saw Ze Frank and said, 'This is big.' And then I said, 'I can do this. I can use it to make a niche - wine, maybe it's not quite ready yet, but it will be if I do it right.' " And so Wine Library TV (also known as The Thunder Show) was born: daily Web videos about wine.

He spoke of wine as no one had before, not with the faux poetry common in the haute monde of wine-talk - "this resonates with compelling nutmeg undertones tinged with the salt of Mendocino sea breeze" - but with "this tastes like old socks" or "this tastes, to me, like burnt rubber." It torqued off the wine establishment, but he didn't care. He was a smash. He says each episode of Wine Library TV gets about 90,000 viewings.

Crossover: He became a sought-after TV guest, appearing on Late Night With Conan O'Brien (where he sniffed his host's armpit to make a point) and The Ellen DeGeneres Show. His jokey, persuasive delivery has made him, along with Perez Hilton, "Dancing Matt" Harding, Marina Orlova, Alejandro Reyes, and Nick Thune, a standout in the first generation of Internet-video stars.

Why? Just look at episode No. 734, "What Wine Pairs with Cereal?" (http://go.philly.com/vaynerchuk), which went live Sept. 8, with sprezzatura and silliness. Vaynerchuk sits with three breakfast cereals - Lucky Charms, Cap'n Crunch and Cinnamon Toast Crunch - each with its own wine. A collision of two worlds that never were in the same orbit.

About six minutes in, he addresses the best wine to go with "the amazing Cap'n Crunch," and here the video reaches truly unknown territory. He recommends a Reichsgraf von Kesselstatt 2007 Scharzhofberger Riesling Spätlese, which has, he says, "this great golden apple and Lipton teabag smell on the nose." He tastes some, then shovels in several mouthfuls of Cap'n Crunch - which, he acknowledges, can "cut the roof of your mouth" - and pronounces the fit excellent.

Not ready for prime time? Who needs prime time? That's the thing about the Web: You build your own audience your own way.

In 2006, he saw Twitter and again got in ahead of the curve: "I saw right away how I could use Twitter strategically."

In Crush It!, Vaynerchuk calls that strategy "The Lure and the Lasso": Build up a big following on Twitter (at last check, Vaynerchuk had more than 850,000 followers), and, tweet by tweet, entice them to your Web sites (crushit.com or garyvayner.com) and your blogs, where your personality (and products) really live.

Debbie Stier, senior vice president of HarperStudio publishers, saw Vaynerchuk speak at the O'Reilly Web 2.0 conference in New York in September 2008.

"He just blew me away," Stier says. "He talked about how to use the Web to turn your dreams into your life work, how to monetize your passion. I said, 'That's the book!' " Stier buttonholed him later - and in April, HarperStudio announced the blockbuster Vaynerchuk deal.

Social media have become a rich lode for book ideas. HarperCollins reportedly paid Nick Douglas five figures for an anthology of funny Twitter posts, mostly by celebrities. Behold: Twitter Wit. University of Chicago freshmen Emmett Rensin and Alex Aciman thought of squishing the world's great literary works into 20 "tweets" or less - 20 sentences of 140 characters or fewer. They sold the idea to Penguin Classics and now have authored Twitterature: The World's Greatest Books, Now Presented in Twenty Tweets or Less. (The Divine Comedy in 2,800 characters!)

Justin Halpern of San Diego started tweeting about his father Sam's funny sayings. He now has 491,757 followers of his daily tweets, sold the rights to It Books, and a book is slated to appear next Father's Day.

Mainstream? Alternative? All media are a linked chain, an eternal golden braid. Literary agents and publishers are trolling blogs, Facebook, Tumblr, Twitter, looking for the great voices of tomorrow.

"With user counters and user comments, you can often tell how big the audience is and what they're responding to in a writer," says McKean, of Howard Morhaim. "If a blog is getting 50,000 unique hits a day, that's 50,000 people seeing this writer. I can take that to my editor and say, 'Hey, we've got a market here.'

"Web bloggers build communities," McKean says. "But a special kind. It's a personal connection, person by person. It's a conversation."

Vaynerchuk says he thrives on the paradoxical personal appeal of mass-market Webcasts: "What I do is extremely sincere on a personal level.

Crush It! is a "short, tight, fast-read book" (the author's words) about creating a Web-based approach to your very own business. "It's also about working happier," he says. "If you're working 17 hours a day for $100,000, consider taking a lower-paying 35-hours-a-week job, stay home, and make a Web site about NASCAR, macrame, tomato sauce, whatever you love."

It takes an immigrant to be this American. Vaynerchuk was born in what is now Belarus in 1975 and came to this country in 1978. "Having nothing and fighting for what I wanted made me hungrier," he says. "Hey, I think like an immigrant. I see the economic downturn as an opportunity. We've exposed the frauds among all the big, established money guys. Why not be honest and a success? And do it yourself, using all the media you can find?"

The immigrant's tale, vintage 2009. "To be honest, I'm not as big at this point in my life as I thought I would be," Vaynerchuk chuckles. "It's funny - I'm working so hard, but I'm laughing all the time."