SIX YEARS AGO, Gary Vaynerchuk was on a night flight back to New York from a speaking gig in what might have been Dallasthese things tend to blur into one for Vaynerchukwhen he leaned his head against the window and had a realization. He was 38 years old, overworked, and out of shape.

I said to myself, Youre going to die younger than you need to if you dont start eating better and working out, and just literally decided right then, within seconds, that on my 40th birthday I was going to hire this trainer, and then theyre going to follow me around in perpetuity, he says. As the flight went on, the plan accelerated. By the time I landed and hit the ground, it went toWhy not start now?

He soon locked down a personal trainer, and suddenly, fitness became Gary Vaynerchuks latest hustle toward getting happier.

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As Vaynerchuk stories go, this one is extremely on-brand. That's because "GaryVee," as hes known among his legion of often young admirers, has built his reputation on moving quickly when inspiration strikes. As the bootstrapping tale goes, he's the guy who, nearly a decade and a half ago, transformed a discount liquor store in New Jersey into an online wine-selling empire through the then-novel sales tactic of creating a YouTube channel and making people really care about him and his products. (The channel was called Wine Library TV.)

As the shows host, GaryVee appeared to be plainspoken and authentic, with sales insights that turned him into a new-age and occasionally f-bomb-dropping business guru. He quickly parlayed that fame into a line of best-selling books and more advice-sharing YouTubes to build an even bigger multiplatform following. He now has 2.1 million followers on Twitter, 2.6 million subscribers to his YouTube channel, 3.8 million fans on TikTok, and a whopping 7.9 million Instagram followers ready to receive daily koans like Spend 0 seconds dwelling about yesterday. But much of his early appeal revolved around a concept that seemed to take a toll as he aged.

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As he shared in a YouTube rant entitled The Most Important Word Ever (spoiler alert: its hustle) that he posted way back in December 2014, the VaynerNation thinks theyre hustling, and straight to your face, I think 99.9 percent of you are not, he says. Everybody has time. Stop watching fucking Lost. That dispatch earned more than 1 million views.

Since he started working out, though, GaryVee seems to have stepped back from that hard stance. In March 2019, he gave a keynote speech at a major marketing forum in Jakarta, the key theme of which was happiness, not hustle. The video is titled 95% of People Are Confused About Success and Happiness. In it he lays out his theory of how to create a better life: I believe that self-awareness, and the ability to actually give without expectations, are the two bricks of happiness, he says in an almost pleading tone with the audience.

The moment comes off as seemingly smart but also a little crypticanother classic GaryVee tactic to get people to listen closer.

WHEN I TALKED to GaryVee during a Zoom call in mid-May, he was isolating at his parents house in New Jersey but still keeping up a busy schedule. He's reportedly married with two young children but is generally guarded about his personal life. "Never assume you have the whole story," he wrote online in defense of apparent criticism of his work-life balance several years ago. "Yeah, you see me working eleven hours and in meetings and flights and hustling. But there is a lot you dont see too."

During our video chat he wore his usual casual uniform, a loose T-shirt and black hat with the letters VS on ithis logo for VaynerSports, his agency, which represents a moderate roster of NFL talent. Beneath the brim, his face was stubbled, and he looked tired.

I think that message got taken too far, he says about his early suggestions that the best way to get ahead was to grind hard, late, and often, although it was unclear if he was taking his own advice.

GaryVee says his days currently begin at 7:00 a.m. with a virtual workout with the same trainer he first hired, Mike Vacantione day arms, the next legs. He looks leaner than he does in older online videos, and says he's added some much needed muscle. He likes training with someone because it holds him accountable.

That's followed by several hours of filming to create his roughly hour-long new YouTube show, Tea With GaryVee, which launched during quarantine to help people during this difficult time, and on which followers tweet at him or even call in virtually for all manner of guidance. It's one way he's realized he can give without expectationhe's responding to what his audience finds most important. He has also learned to pay close attention to how people are receiving each message he puts out into the world. What I do for a living, probably more than anything else, is read comments, he says.

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His afternoons consist of virtual meetings for VaynerX, the umbrella company of the seven businesses in the GaryVee empire, which basically break out various opportunities for the different clients and companies he represents. Theres VaynerSpeakers, VaynerProductions, VaynerCommerce, and other assets. In total, hes estimated to be worth about $160 million. His creative agency, VaynerMedia, has worked with clients like Pepsi, Chase, and Budweiser.

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He has dinner with his folks at 7:30 p.m., he says, and spends another hour or two on email in the evenings. Rinse, repeat. Anybody familiar with Vaynerchuk shouldnt be surprised that hes still trying to work under lockdown. But the experience has also prompted himas it has many of usto reflect on his life and business. When he comes out of this, he wants to travel less and spend more time with his kids. He currently makes about 150 flights per year, but says hes planning to reduce that by at least 20 or 30 to start.

He was also helping to organize a coronavirus-relief event called the All-In Challenge, which features a number of sweepstakes and auctions for experiences with celebrities including Tiger Woods, Chris Hemsworth, and Kelly Slater. One prize will give someone yearlong ultimate access to Vaynerchuk, including moments that appear custom-built to help him unplug, although its unclear if hell use this for future online content. The adventures include garage-sale scavenging (a favorite pastime), training sessions with him and Vacanti, and tailgating at a New York Jets game. He hopes to one day buy the forlorn football team.

VAYNERCHUK'S LEGEND AS a hustler is well-known, akin to the Horatio Alger myth and tied into the way many of us judge success still today. He was born in the Soviet Union in 1975, and his American journey began three years later, when his family moved to Queens, New York, before settling in Edison, New Jersey. When Vaynerchuk was a kid, his dad ran a liquor store and the family of eight lived in a small studio apartment. To make his own money, he washed cars, operated a lemonade franchise, and bought and sold sports cards (an interest he maintains to this day).

After graduating college in 1998, Vaynerchuk took over operation of his dads store in Springfield, New Jersey. He rebranded it from Shoppers Discount Liquors to Wine Library, and focused on online sales. In 2006, Vaynerchuk launched Wine Library TV, a daily webcast about wine that he posted on YouTube, which was still in its infancy. Vaynerchuk has large, curious eyes accented by thick eyebrows and a dimpled smile that allows him to make a minimal mood change feel infinitely more expressive. He speaks at a steady pace that makes what hes sharing accessible and not too slick feeling. The effect is earnest yet unapologetic, energetic but empathetic all at the same time.

In five years, his small family business was doing $60 million in annual revenue. GaryVee has since written four best-selling books that read a lot like business and lifestyle how-to manuals with hustle as the recurring ingredient. (The titles include both Crush It! in 2008, and its follow-up a decade laterCrushing It!) As for concrete sales tactics, he offers that, too. His 2013 book, Jab Jab, Jab, Right Hook, covers the one-two punch of first offering your fans something of value and then making your ask.

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During a recent episode of Tea With GaryVee, for instance, he spoke with a young woman about connecting with influencers to help sell her book (You need to be reaching out to every podcast, every platform you can), conversed with a follower about how she can help people by becoming a life coach after getting out of an abusive relationship (The only way youre going to do itits similar to working outyou have to put in the reps, you have to put out the content), and spread his gospel about producing lots and lots of content to gain momentum (Something happens when you put something out).

The actual sell was subtle: He signed off by saying, Im going to hang up now and write todays wine text, because its the single best pinot noir weve ever offered.

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VAYNERCHUK MAY BE pushing for more balance in his lifeand yoursbut hes far from saying hustle is bad word. Coming out of the coronavirus pandemic, he says, I have a funny feeling that hustle and hard work are about to be put on a pedestal again because 50 million Americans are out of jobs.

For him, the current moment feels similar to, although obviously more deadly than, the financial crisis of the late aughts. The economy was in a tailspin. The world was financially melting, and I definitely am a high-energy guy, and I definitely made comments like 7:00 p.m. to two in the morning is your opportunity to shine, because I was desperate to help people, he says. I was like, Hey, youre crying, youre suicidal. The Internets here nowyou could be actually having a job and coming home and starting the next thing that can get you out of it.

I still to this day believe hard work is foundationalbut Im empathetic to it, he says. I could have done a better job to create more clarity about balance. And I think also I have garnered the wisdom over the last 12 to 15 years to realize, wow, when youre a communicator, people are going to run with individual parts and take them directly out of context.

This introspection about how his message is received has prompted more nuance in how he delivers it. The smart hustler needs to pick a pace that feels sustainable because it takes time to get ahead. I would argue with most people that if they dont have the patience to navigate through choppy waters for 18 months, its highly unlikely that theyre going to achieve what they want anyway, he says.

Vaynerchuk admits that hes often winging it onstage, so its fair to say his theory of happiness is fluid. But the Jakarta talk stands out for the way he implores his audience not to simply hustle for what they want but to live a life thats fulfilling to them. Self-awareness, Vaynerchuk explains, is about competence over insecurity. Self-awareness means knowing your shortcomings and being okay with them. It means reading people around you and knowing your audience. Giving without expectations means having no agenda. I think a lot of people give as a manipulation tactic. Its, youre giving for a reason, he says.

In Jakarta, he made no promises that his advice could lead his listeners to financial success. Instead, he told the crowd, almost all of whom were young entrepreneurs, that many of them would fail. The point, he said, isnt success alone. The point is to make sure youre doing something because you believe in yourself, and then, because in many ways you cant control the outcome, to learn to feel good about the way you tried to make that happen.

Please, my friends, dont live a life that gets you to 80, 90, 100 years old, where youre sitting there saying, I wish I did, Vaynerchuk said at the event. Older people will not talk to you about what they did, but what they didnt do.You have one life, you might as well live it.

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To that end, his recent social-media posts have been affirmingand could also read as his own reminders to maintain a less-frantic lifestyle. Stop telling people how to fix themselves, fix you, he writes in one. Everythings scary until its not, says another.

If more people decide to tune in for that kind of wisdom, the happiness message could become pretty lucrative for GaryVee. But he appears to genuinely value his new perspective.

"I used to think I was outworking people[but] as I became more known and had more human interactions, things started to become clear to me, Vaynerchuk says. Its funny, because Im such a modern communicator, but Im such an old-school character. As Ive gotten older, Im like, Oh, right. I believe in the shit that the 90-year-olds believe in. You know what I mean?

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