How Gary Vaynerchuk Mastered The Art Of Engagement
Entrepreneur|June 2017

Gary Vaynerchuk is half man, half brand, half digital experiment. And somehow, that all adds up.

Eric Adams

Gary Vaynerchuk arrives at his Manhattan office at 8 a.m. There’s no slow ascent—no sipping coffee while scrolling through emails, no idle chitchat to forestall the onslaught of responsibility. Instead, as he does every morning, he quickly huddles with the two people who will accompany him throughout the day: his personal assistant, which is typical of most executives, and his personal videographer, which is, let’s just say, a profoundly Gary Vaynerchuk kind of role.

The assistant, Tyler Schmitt, runs Vaynerchuk through the day’s schedule. There are 24 meetings, including check-ins with the staff and clients of his digital media agency, Vayner- Media, as well as a wild assortment of guests—social media stars, athletes, actors, musicians, many with entourages in tow. As usual, the action will be captured by the videographer, David Rock, nicknamed D-Rock. When the time comes, D-Rock will raise his camera, train it on his boss, and barely take it off him all day, except during sensitive client meetings.

“All right, you guys ready?” the 41-year-old CEO says to Rock and Schmitt, who are now standing with a few other members of what, internally, is known as either Team Gary or Gary’s Team—a 16-member group that also includes a brand director, designers, merchandisers, influencer marketers, and business developers. “Let’s start the show.”

At 8:10, the guests start arriving. There’s an interview with a potential executive hire, a podcast recording with Digg founder Kevin Rose, a talk with a young Dallas entrepreneur who won face-to-face time with Vaynerchuk in a Twitter competition. Then another meeting, and another, in blocks of five minutes up to an hour, with Vaynerchuk gesturing, laughing, swearing freely, peppering each visitor with questions, and offering assessments. “You need a teammate, so let the things you aren’t gravitating to yourself lead you to the partner you’re looking for,” he tells Daina Falk, creator of the Hungry Fan sports tailgating site and cookbook, who is working to manage her brand’s growth. “I really do think Facebook is Netflix’s biggest competitor, so listen—write a TV show, but do it on Facebook,” he tells Greg Davis, Jr., a.k.a. Klarity, a 32-year-old actor who wants to expand his social following.

There’s a string of internal confabs. “If I’m the bottleneck, let’s try a meeting where everyone hurls questions at me and I can only say yes or no, just to clear up the things that get clogged,” he suggests to his management team. (They try it two days later. It doesn’t work; Vaynerchuk talks too much.) There’s the surprisingly businesslike crew from hit Instagram mememachine FuckJerry, reps from the NHL, a Los Angeles style blogger, and rapper Sean Combs’ social media team. “Diddy’s trying to reach a new audience,” says Deon Graham, the boss. Vaynerchuk is all over it. “Puff has energy, so let’s give your new team the reins on new ideas,” he says. The ideas themselves will come after a dinner meeting between Combs and Vaynerchuk, which Graham vows to set up. After a round of the requisite selfies, which almost every visitor takes with Vaynerchuk, they bounce. More meetings convene. Scheduled ones, impromptu ones, conference room drop-ins, Sorkin-esque walk-and-talks. I ask Schmitt, the personal assistant, what happens if someone cancels a meeting. He looks at me blankly. “He finds a meeting.”

Through it all, Rock is a persistent fly on the wall, training his DSLR on the action. Sometimes he’s in the room, sometimes he grabs scenes from outside the glass partition, moving the camera around for dramatic effect. Originally, Rock produced this reality show himself—filming and editing the videos of Vaynerchuk and uploading them to social. Now he has a team of videographers, which speeds the turnaround. The meetings I witness today will be cut up, subtitled, set to a beat, and released tomorrow as a show called DailyVee on YouTube (to Vaynerchuk’s 645,000 subscribers) or in quick hits on Twitter (nearly 1.4 million followers) and Instagram (1.7 million).

The clips tend to capture Vaynerchuk frenetically hammering home his favored themes—focus on your strengths, work your ass off, spot the next big shift and get there first, stop obsessing over stuff that doesn’t matter, be the bigger person, give more than you get, and above all, execute. All this output, plus his relentless social media engagement and videos where he answers viewers’ questions, has fostered an ever-growing group of fans who treat him as an all-knowing sensei, enamored with his ability to cut right to the heart of their problems. And that, in turn, has turned him into an entrepreneurial celebrity. In addition to the videos, he pumps out books, podcasts, and many conference keynotes, and is now costarring in Apple’s first-ever original TV series—a tech-based reality competition called Planet of the Apps—alongside Jessica Alba, Gwyneth Paltrow, and will.i.am. Last spring when he tweeted that he was in London and offered to meet with followers, 200 people converged on a city park, all hoping to pick his brain, #AskGaryVee–style. (That would be his YouTube Q&A show, of course.)

This high profile has also drawn a different, less flattering kind of attention. The world of entrepreneurship is, to be frank about it, full of hucksters—people who had one business success, or maybe skipped that part entirely and went directly into wisdom-spouting mode. To the polished bosses of old business in their sepulchral C-suites, Vaynerchuk can look a lot like King Huckster himself. After all, who the hell is so sure of their golden word that they’d pay a videographer to tail them?

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