What Gary Vaynerchuk Learned by Experimenting on Himself

Gary Vaynerchuk is half man, half brand, half digital experiment. And somehow, that all adds up.
Gary Vaynerchuk Source: Photographs by Pieter Henket / Groomer, Blair Jaffer

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, VaynerMedia, 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.

Related: 10 Steps to Becoming a Successful Entrepreneur

“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 with a potential executive hire, a podcast recording with 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 sports tailgating site. “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.

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