Entrepreneur

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

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.

You’re reading a preview, subscribe to read more.

More from Entrepreneur

Entrepreneur3 min read
What’s the Real Damage?
Miri Offir knows how to talk to people in crisis. After serving in the Israeli military, she came to the U.S. in 2003 and took a secretary job at the post-disaster recovery franchise 911 Restoration. She worked her way up—eventually becoming the comp
Entrepreneur2 min read
Japan
These past few years have been witness to an extraordinary economic renaissance in the world’s third-largest economy. From cost-cutting and sluggish to dynamic, growth-orientated, and rocket-fuelled by active investment, healthy inflation, and a high
Entrepreneur5 min readCorporate Finance
How to Build the Next Huge Thing
Want to start, fund, and sell a major company? Spencer Rascoff has some advice on that—because he’s seen it from all sides. As a founder, he first cofounded the travel-booking site Hotwire, which he sold to Expedia. He then cofounded Zillow, which he

Related Books & Audiobooks