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What Gary Vaynerchuk Learned by Experimenting on Himself Gary Vaynerchuk is half man, half brand, half digital experiment. And somehow, that all adds up.

By Eric Adams

This story appears in the June 2017 issue of Entrepreneur. Subscribe »

Photographs by Pieter Henket / Groomer, Blair Jaffer
Gary Vaynerchuk

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

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