How Gary Vaynerchuk Mastered The Art Of Engagement

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.”