IT’S the last weekend of summer and Gary Vaynerchuk is buying a soapbox derby car from a stranger. He’s already purchased a thumb-size figurine and a coffee mug (for 33ȼ). For the chairman of VaynerX, a nearly $300 million media umbrella company that encompasses nine brands, including Vayner-Media, of which he’s CEO, cruising garage sales in suburban New Jersey isn’t so unusual. Never mind that two companies he helped create, Resy and Empathy Wines, have sold in recent years for hundreds of millions of dollars, or that his net worth has been estimated to top $200 million, or that his companies have some 1,800 employees—this hobby is important to him, and he feels it might be educational for his 35 million social media followers. He holds up his phone to record a video he’ll post to Twitter: “I’m out here fuckin’ showin’ people what they can do with $20, $40, $60. You can fuckin’ make 800 bucks and turn that into an NFT. And then build. No excuses. Accountability. You can take control. You’ve got this. And it’s fun, too.”
Vaynerchuk, more commonly called GaryVee, is known for a lot of things, but perhaps foremost for his brassy salesmanship that came of age along-side the social internet. He made his name first by turning his parents’ New—in five years and in the process turned himself into something of a product by posting captivating, near-daily videos analyzing wines. By 2009, he had spun his uncommon ability to amass followers into its own business by launching the digital marketing agency VaynerMedia, which led to all those other companies under the VaynerX umbrella-Vayner—Productions, VaynerCommerce, Vayner-Speakers, VaynerTalent, and so on. Along the way, he wrote five best-selling books and honed a brash, cursing-while-motivationally-speaking-in-a-New-Jersey-accent style that became as much a part of his renown as the actual message he was delivering.
