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 33¢). For the chairman of VaynerX, a nearly $300-million media umbrella company that encompasses nine brands, including VaynerMedia, 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 alongside the social internet. He made his name first by turning his parents' New Jersey liquor store into a $60 million brand -- Wine­ -- 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 -- VaynerProductions, VaynerCommerce, VaynerSpeakers, 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.

"My delivery has always had such wrestling-promo energy that I think it's created confusion around what I've been saying."

Take the garage-sale video, for example: It's pure hustle-porn on one level, a guy exhorting his audience to turn even the most trivial-seeming Saturday activity into an opportunity to build and conquer. But on another level, it's a lesson in Vaynerchuk's latest business obsession: collecting, creating, and selling NFTs (or non-fungible tokens).

A week later in his New York City office high above the glossy Hudson Yards development, he's dwarfed by a wall of shelved sports memorabilia -- Air Jordans, ThunderCats figurines, multiple figurines in his own likeness. And doodles, lots of doodles, illustrations of simple little animals with earnest names such as Passionate Parrot that Vaynerchuk has drawn, digitized, and put up for sale via blockchain in the form of 10,255 NFTs (based on 268 characters). NFTs, he argues, are a key to the future of the internet -- as important as the social-media revolution that he's ridden to success. Hence the newest member of the VaynerX constellation: VaynerNFT.

His newest book, Twelve and a Half: Leveraging the Emotional Ingredients Necessary for Business Success, comes out November 16, and Vaynerchuk seems uncharacteristically cool-headed as he describes his new focus. On the cusp of 46, the man who shouted himself to success-guru fame is reinventing himself as an empathic leader and an advocate for a kinder way of doing business. Well, that and solidifying himself a place in the crypto-art avant-garde. He explains...

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IT'S FUNNY -- I think that I've really done a great disservice to myself over the past decade because of my obsession with being my full self. I'm such an excitable, passionate communicator that when I'm onstage or doing an interview, I'm 11 out of my normal 5. But my delivery has always had such wrestling-promo energy that I think it's created confusion around what I've been saying. When you have that big of a style, it definitely turns off a percentage of people. It makes people cynical. Is this for real? There's a level of showmanship.

It's just that there are a trillion pieces of content out there, and I'd like for people to hear my message.

I believe that a lot of my competitiveness and aggressiveness in business developed because of my infatuation with sports. It's kind of accepted in sports, right? In a Jets game, they bash each other's faces in, and afterward they hug it out. But in business, we often don't have that last part. People take it very personally. If you compete with somebody in business, you feel like you have to have an issue with them in real life. That's unfortunate.

I realized over the past three years that I don't practice winner-take-all business. I think you can win in a really good way. I'm not about sharp elbows.

I think I was very affected by listening to my family as a child. Ninety-five percent of the adults' conversation was about how thankful they were to live in America, not Russia. My mother overcame so much adversity. She lost her mom at 5 and grew up in the Soviet Union. Her father went to jail. And yet she is the most positive person I know. I've realized that my soft skills, being like my mother more than my father, has been my secret weapon in business.

That gratitude and optimism and curiosity have led to who I am today, which is someone ambitious to squeeze everything out of life. Because one day I'll be 90 and there won't be much squeezing left. There's no business school, no Y Combinator, that teaches accountability, empathy, gratitude, patience, optimism, self-awareness, tenacity, kindness -- some of the ingredients in the title of my new book. But there's nothing that more consistently determines success than how one handles those. I believe there's a direct correlation.

Of the emotional intelligence frameworks, I've struggled most with candor. The majority of things that have not worked for me in the past 25 years have been related to a lack of candor. You might struggle with something different. Maybe you don't have tenacity or self-awareness figured out. Or you might be a pessimist. All of those traits become your strengths or your weaknesses, and I wrote the book because I wanted to talk about how they all work with one another.

"Accountability, empathy, gratitude, patience, optimism, self-awareness, tenacity, kindness -- nothing more consistently determines success than how one handles those."

I'll give you an example. There was a moment maybe five years ago when we did a round of layoffs after going from 30 to 600 people. I could feel the company was lethargic, and the reason we were was because we were holding onto people at all costs. So we let go of 38 people, and I was empathetic when I spoke to the team -- but the reaction was as if I had sold the company to dictators. I had created entitlement. I had thought that if I spoke to you with candor about something not going well, you'd go into a negative spiral or become depressed or quit. So I had avoided those conversations.

Which is crazy, because my onstage persona is all about candor. Onstage, it's a piece of cake. But if you worked with me, that wasn't the case. Now I'm passionate that putting the word kind in front of candor can help. Learning to practice kind candor has really leveled up our organization.

I believe that over the next 50 years, the rules of engagement, what it takes to be successful, are going to be rewritten. I think it's time we redefine business. Kindness is a word that should be at the table. Empathy is a word that should be at the table. And I think that curiosity has been completely misunderstood. Innovation comes from curiosity.

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IT WAS CURIOSITY, in fact, that led Vaynerchuk to launch his NFT business. After some nail-biting and layoffs at the pandemic's outset, VaynerMedia roared back. It opened offices in Mexico City, Bangkok, Tokyo, and Sydney, and grew operations in London and Singapore, where Vaynerchuk now has 150 people. Then one day around the end of 2020, he was talking with his friend Kevin Rose, the founder of Digg, who shares his love of collecting. "Do you have a CryptoPunk?" Rose asked, referring to an early type of NFT pixel-art character. Vaynerchuk did not. He'd been so focused on getting VaynerX on track he'd let the rise of NFTs happen right before his eyes without ever focusing on it.

So he went to work and followed his curiosity as far as it would take him -- which, naturally, led to the launch of VaynerNFT this past July. Even before that, his first NFT product was a slate of deeds for digital characters called VeeFriends -- those cute little animal doodles -- which could be purchased with Ethereum cryptocurrency and which give their owners access to a Discord server, conference tickets, and maybe even a Zoom with Vaynerchuk.

When we spoke, he was preparing to, separately, launch an online NFT marketplace and a real-world art gallery, and the auction house Christie's was set to auction five of his physical drawings that he'd used to create VeeFriends -- including one called "Diamond Hands" Hen, a chicken that appears to have pooped a diamond. A week later, it sold for $162,500. Another, Empathetic Elephant, sold for $412,500. He tells how he did it...

"There are a lot of people who dismiss NFTs today who would recognize their brilliance if they took the time. It's no different from how Twitter confused people."
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AFTER TALKING WITH Kevin Rose, I went and did 30 or 40 hours of homework just on CryptoPunks. I started honing my point of view -- just started talking to friends, reading Twitter, reading Discord, watching videos. I went all the way from "What is an NFT?" to much nerdier, deeper stuff. And then, somewhere during that process, I said to myself, "The way I learn is not by reading. The way I learn is by doing." So I ­decided to do a project. I decided to make VeeFriends.

I'd had these characters in mind since 2017. I'd been getting DMs from people who said a piece of my content had made them feel better at work. I had thought I'd make little plush toys that could sit on people's desks. When their boss is mean, they're going to look at the character -- an Empathy Elephant or a Patient Panda -- and feel better. Simultaneously, I'd wanted to do a business conference similar to South by Southwest. I wondered if it could all come together.

A month later, I went off the grid for a week, drew the characters, and worked on creating the NFTs. That was in March. It took between one and five minutes of actual drawing per character. Maybe 17 minutes to decide on a name -- whether I wanted, say, Gracious Gopher or Gifted Gopher. That was it. That was the process.

I really believe entrepreneurship is a form of art. I rarely hear business people talk like me, but I often hear artists talk like me. When somebody goes off the grid to work on their album, I understand that. That's what I did with VeeFriends.

We built a whole company around VeeFriends. In addition to digital ownership of the assets, if you own a VeeFriend right now, you are a member of a community and have a ticket to VeeCon, our conference. The first VeeCon is coming up in May 2022 in Minneapolis. Attending it is part of the underlying value of VeeFriends.

NFTs are still misunderstood. People will absolutely transact meaningful purchases -- homes, other assets -- on the blockchain through NFTs. It's a contract. A contract that has no fees involved and is non-changeable and transparent for everybody to see. Think about that.

There are a lot of people who dismiss NFTs today who would recognize their brilliance if they took the time. It's no different from how Twitter confused people about the future of social media, no different from how people underestimated online business because went bankrupt. No different. This is my third rodeo. I've seen this movie before.

I think every single person on earth will interact with an NFT in 20 years. There won't be a single person who doesn't. Because I think they're going to be your train ticket, your concert ticket. This is too obvious. I'm not here to do a one-night show. I'm here for the rest of my career with VeeFriends.

I've been very fortunate. I can deal with being misunderstood, underrated, not rated. I'm in a luxurious mental place. But I'd be lying to you if I said I don't appreciate this moment in my career when the cynicism has really quieted down.

The $200 million-plus sale of Resy to Amex. The nine-figure exit of Empathy Wines to Constellation. The fact that VaynerX is close to a $300-million company built from scratch. There are just too many successes for anyone to write it off as all sizzle. Add the NFT project to that list.