If you’ve spent more than two minutes somewhere on social media, you have probably come across Gary Vaynerchuk. For years I have wondered, is this just a character? Or is there a real Gary Vaynerchuk somewhere behind “GaryVee,” the social media entrepreneur and internet brand?

Gary got his start working at his family’s liquor store, which he turned into an online wine shop. That’s where he started in social media, hosting a long-running YouTube show called “Wine Library TV.” He parlayed that into the gigantic GaryVee brand, which at its core, is about entrepreneurship. Gary co-founded the restaurant reservation platform Resy, which he sold to American Express in 2019, and Empathy Wines which he sold in 2020. 

The Vaynerchuk empire remains vast, and it’s structured in complicated ways. There’s holding company VaynerX, which contains the ad agency VaynerMedia. There’s another company called Gallery Media which owns lifestyle websites. Gary even co-founded a sports agency – VaynerSports, with pro athletes like the NFL’s Kirk Cousins and Sauce Gardner on the roster, MLB shortstop Bo Bichette, and a variety of combat athletes.

On top of all that, there’s a serious upheaval going on in digital media. The era of the social web is coming to a major moment of change, with new platforms like TikTok in the mix and old standbys like Twitter and Reddit going through complicated and controversial resets. New platforms bring new personalities and influencers, who are native to those platforms and maybe better at capturing the audience there.

It’s one thing when you’re the first GaryVee. But staying GaryVee, in a time of change, and pitching brands and companies that his approach to social media will stay relevant, is an ongoing challenge.

We got to chat with Gary at his Hudson Yards office in Manhattan and I will tell you, he did not hold back with his answers.

Links:

A trip to the GaryVee convention, where everyone is part of crypto’s 1 percent - The Verge

How Gary Vaynerchuk Became an NFT Guru

Gary Vaynerchuk expects NFTs to expand beyond digital collectibles long term | TechCrunch

Transcript: https://www.theverge.com/e/23530741

Credits:

Decoder is a production of The Verge and part of the Vox Media Podcast Network.

It was produced by Jackie McDermott and Raghu Manavalan. It was edited by Callie Wright. 

The Decoder music is by Breakmaster Cylinder. Our Editorial Director is Brooke Minters and our Executive Director is Eleanor Donovan.

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