Riding the Hashtag in Social Media Marketing

This will not be a conventional punch in the face, but a Vaynerchukian punch, which turns out to be the opposite of violent. Mr. Vaynerchuk, 37, is a social media marketer with some very big clients, and he’s a tireless self-promoter. Anyone fitting that description is all but required to find novel ways to win attention and coin catchphrases, and his new favorite is “jab, jab, jab, right hook.” That is also the name of his coming book, which is due out this month and is subtitled “How to Tell Your Story in a Noisy, Social World.”

A jab, in Mr. Vaynerchuk’s lexicon, is anything of value — a joke, an idea, an introduction. Or a meal. Not long ago, a follower in Minnesota joshingly responded to one of his can-I-help tweets with a request for a cheeseburger. The next day, a cheeseburger was delivered to the guy’s home. When a follower in Canada wrote “Just ran out of Tabasco,” Mr. Vaynerchuk overnighted eight bottles.

It’s unclear how a smack in the jaw came, in Mr. Vaynerchuk’s ever-churning imagination, to mean a gift. But after he delivers a few jabs, he — or the many companies that hire him to promote their brands through VaynerMedia, his agency based in Manhattan — can then hit you with a right hook, which in his world translates into a request to buy something.

Jab, jab, jab, right hook means give, give, give, ask. “A funny thing happens when you give value up front,” he is fond of saying. “You guilt people into buying stuff.”

On a sunny September afternoon, Mr. Vaynerchuk was sitting in the back of a taxi, jabbing one Twitter follower after another on his iPhone. He had just delivered a speech in SoHo at the 99U Pop-Up School and was on his way to lecture a room full of social data specialists at the Mandarin Oriental hotel.

In between, he rummaged through postings with the hashtag #99school, many of them raves about the talk he had just finished.

“Great talk by @garyvee at #99school today,” one tweet read. “Helped me understand how Twitter has evolved & I really liked the ‘Jab-jab-jab-hook’ idea.”

As the taxi rolled uptown, Mr. Vaynerchuk wrote back, “That means a lot to me man.”

Naturally, this brief acknowledgment was strategic.

“I’ll literally jab, jab, jab, right-hook this guy,” Mr. Vaynerchuk explained. “I gave him good information, he then responded to it, I appreciated him saying something nice about me. I later will ask if he has pre-ordered the book, and he’ll say, ‘No, but I’m going to do it right now.’ ”

70 Tweets a Day

If reducing virtually all human interaction to purely transactional terms isn’t your style, you probably should avoid Gary Vaynerchuk. Since his childhood days hawking baseball cards at convention halls in New Jersey, and later pitching wine online at his father’s liquor store, he has dedicated most of his waking life to a single puzzle: What will sell more stuff?

In recent years, that puzzle has given ulcers to a lot of executives. They have watched the rise of Facebook and Twitter, along with the advent of commercial-skipping technologies like DVRs and hardware like the iPad, and realized that spending money on television, print and radio will no longer suffice. But how do you market to people in these virtual realms? Given that these platforms are supposedly about friends connecting — it’s called social media for a reason — will anyone listen and look? Is it too much to ask for a return on this investment?

These questions have produced an age of anxiety in marketing the likes of which have not been seen since television and Uncle Miltie landed in living rooms decades ago, and it has given rise to a new tribe of entrepreneurs, all peddling their own forms of Xanax. There are now so many social media experts out there that some of them renounce the label.

“Look at any tech conference,” said Peter Shankman, a social media consultant who rejects the social-media-expert tag. “Anyone can call themselves that. It’s just too easy.”

Mr. Vaynerchuk is not shy about embracing the title because he is not shy about anything. A small and kinetic man with dark hair that is starting to gray, he speaks with a warm, raspy voice, as though he’s been talking all day, which he usually has. He is funny and profane and gesticulates constantly, putting air quotes around phrases that he merely wants to emphasize. Among this favorite subjects are the New York Jets, which he has vowed to buy, and his own talents, which amaze even him.

“I have as big of an ego as it gets,” he said during a recent interview, in a tone suggesting that he was simply stating the facts, “but I have, stunningly, a lot of humility considering some of the accomplishments I’ve had.”

These accomplishments include the building of VaynerMedia, which opened in 2009 and now has 290 employees, serving clients as mainstream as Del Monte, General Electric and PepsiCo. They come in the hope that Mr. Vaynerchuk can do for them what he has already done for himself: build an online audience through pluck, ubiquity and charm.

“When I think about Gary, I think about scrappiness before anything else,” said Linda Boff, G.E.’s executive director of global brand marketing. “He lives his own life out loud.”