Gary Vaynerchuk greets attendees during the 2014 SXSW Music, Film + Interactive Festival
Earl McGehee/Getty Images for SXSW

From a simple wine podcast to launching one of the most renowned social-media marketing firms in the country, Gary Vaynerchuk proves that he’s a business guru.

It’s good to be Gary Vaynerchuk. It’s 10:30 on Tuesday morning, and already he’s called one employee to his 16th-floor Manhattan office to bestow a raise, and for the better part of the last hour, he’s been mentoring a 29-year-old acquaintance who is unsure of where to take the startup he’s launching.

“I’m a big fan of betting on black and white, and then hoping for gray,” Vaynerchuk tells the young entrepreneur, who is hanging on to his every word. Then, the marketing guru who’s made megabucks many times over by helping Fortune 500 brands become even bigger leans in even closer. Sounding more like a big brother, he says, “You know, branding is so funny. It’s just so serendipitous at times.”

It’s a dose of Vaynerchuk’s trademark mix of expertise and candor that has converted the better part of more than 1 million Twitter followers into loyalists and transformed Vaynerchuk himself into a New York Times best-selling author renowned for his ability to use social media to capture the hearts and minds of global consumers.

By any measure, he’s come a long way since first gaining a public following with Wine Library TV, his amateur video blog reviewing wines, including selections at his family’s New Jersey wine shop. Eight years after his first post, he’s now CEO of VaynerMedia, a 325-person social media marketing firm, and he’s produced a steady stream of bigger and better hits. Other chief executives might have considered his busy schedule of morning appointments distractions at worst and charitable moments at best, but not Vaynerchuk, who’s built a business — and an online persona — on providing value, whether measured in favors or deals.

“Good news is a heck of a lot more fun to deliver than bad news,” he says at his desk before turning to his next order of business: dialing in to a radio interview to promote his fourth and latest book, Jab, Jab, Jab, Right Hook: How to Tell Your Story in a Noisy Social World. He defines jabs as the social media content that engages customers, and right hooks as sporadic calls to action that convert that traffic into sales.

Now You Know: Vaynerchuk's younger brother, A.J., is his right hand man, literally. His desk is right next to Vaynerchuk's.

“When you’re giving to someone first, not everyone’s going to think they owe you, but some people will,” he tells the show’s listeners, while bouncing in his chair. “There’s just a lot of power in giving first.”

These are Vaynerchuk’s defining traits — a commitment to nurturing personal relationships and a heady supply of frenetic energy that he harnesses to mountainous results. His zest for the hunt is evident in his vocabulary, which makes liberal use of the words energy and crush. The fact that he takes each minute seriously is evident too.

“From 10:53 to 10:57, I’m going to check email and tweet,” he says as he hangs up with his interview. “From 2007 to 2011, I almost responded to literally every single person.”

Now the sheer number of people who tweet at him makes it impossible to ­connect with everyone. But it seems most of the magic still happens in the Twittersphere, where he is known as @Garyvee, the approachable guy next door who happens to be a mad visionary. Through his 110,000 tweets, he shares glimpses into his business acumen and ­family life while riffing with strangers worldwide on topics from technology startups to his favorite team: the New York Jets.

When the clock strikes 11 a.m., Vaynerchuk departs for his daily stroll around the bi-level office, the rapidly expanding company’s fourth site in five years. He greets everyone by name, and he eagerly interjects whenever he catches wind of talk about his favorite topic: football.

Jake Chessum/Trunk Archive
"Creating content that engages a community reaps returns greater than any ad that money can buy. "

“They should really force two-point ­conversions,” he tells one employee in the hallway. “That would change the game. ­Literally. It would eliminate overtime.”

He’s slight, in baggy jeans, a blue sweater and blue Nikes, and he speaks breathlessly — his raspy voice rising when he’s excited and doling out staccato phrases, often while looking at his smartphone, eyes darting to the next big thing. Because that’s his business: knowing the next big thing before anyone else. Less than three years ago, he had just 20 employees. Now VaynerMedia has offices in San Francisco and Los Angeles, and soon there will be one in Singapore. All are populated­ with recent graduates who speak fluent Facebook, Instagram, Twitter, Pinterest and Tumblr. At 38, he is social media’s elder statesman, a larger-than-life sage.

“Everyone’s, like, under 25,” he says. “They don’t get references to The Wonder Years. I’m so old.”

But they’re bonded by Vaynerchuk’s simple guiding philosophy: Modern times require everyone to be a one-person ­media company, he insists, because creating ­content that engages a community — be it a photo on Instagram, a comment on Twitter or a link on Facebook — reaps returns greater than any ad that money can buy.

When he’s not expanding his own company, he’s investing in others, specifically, the platforms he thinks will help his clients reach more consumers. Three weeks from today, he will announce his next major venture, a $25 million seed fund to incubate startups, backed by Miami Dolphins owner Stephen Ross.

But today, if he’s got the deal on his mind, he doesn’t show it. After a lunch meeting with a client, Vaynerchuk returns to his desk, and without pretense, an employee walks in, a smartphone at the end of his outstretched arm.

“Just let me flow,” Vaynerchuk says. He begins speaking into the phone, delivering a near perfectly hatched blog post off the top of his head about his New Year’s resolutions, which include walking his daughter to school three days a week, an activity that’s helped him shed 4 pounds so far. Then, he gets up, the worker exits, and Vaynerchuk heads to the conference room next door, where an eager entrepreneur looking for investment dollars is waiting for him. He spends half an hour asking questions about the man’s startup, which is in an industry far removed from his own interests. Vaynerchuk listens intently to the man, while biting his nails and spinning his wedding ring on the table.

He’s made 54 investments, from Twitter to Tumblr, but this business is not going to be one of them.

“I don’t know how to say this any other way than honestly,” he tells the man. “It’s not super interesting to me.”

“But I really hope you prove me wrong,” he adds. “Listen, I passed on Uber the first time.”



Gary V.’s Tips for Success

Focus on what you can give, not what you can get.
“If you’re focused on giving up front, you can develop strong, long-lasting business relationships that will continue to yield results for years instead of burning someone out and leading with ‘the ask.’ ”

Over-communicate.
“This is a must in all of the family businesses I’ve run. It might have led to some tears along the way, but it always made the company (and our relationships) stronger.”

Trust your employees.
“It’s what they’re there for, right? Giving someone the opportunity to rise to a task you might have reserved for yourself can mean huge growth for them and more bandwidth for you.”



Jaclyn Trop has written for the new york times, Marie Claire and New Yorker.com. She is based in Los Angeles