How hustle icon Gary Vee found his inner Ted Lasso

The hustle mindset made Gary Vaynerchuk famous. But another quality has been increasingly important to the 49-year-old serial entrepreneur's staying power: empathy.

"So many of you are so much more capable than you think," Vaynerchuk said during his closing keynote at this year's VeeCon, an annual event designed to showcase his various interests, from blockchain to the creator economy. "And I can see it in your eyes that you don't think you can. And it's so blatantly obvious to me that you can. I just want all of you to know from the bottom of my heart, you're dramatically more capable than you think you are."

The audience ate it up.

Vaynerchuk, also known as Gary Vee, has built a legion of fans, many of whom are young men, by evangelizing hard work. He has 50 million social followers, including 15 million on TikTok. He's also drawn critics who say he glorifies a toxic hustle culture and capitalism. For years, his Twitter handle read "a dude that Loves the hustle." In recent years, though, his message has become less shouty and more affirmative, a shift that's coincided with a growing desire for empathy and national attention to the plight of young men.

This turn, like so many in Vaynerchuk's career, has involved a combination of personal branding and business. He launched a direct-to-consumer wine brand called Empathy Wines, which he later sold to Constellation Brands. He started VeeCon to sell his line of cartoon characters, VeeFriends, that personify positive characteristics, like Capable Caterpillar. It's partly this constant evolution — and ability to adapt to cultural trends — that has helped Vaynerchuk's 15-year-old advertising holding company, VaynerX, get on track to post $300 million in revenue this year. That figure, which he revealed for the first time to Business Insider, has more than doubled in the past five years and outpaced growth in the ad industry overall.

In the collection of podcasters and other media figures sometimes called the manosphere, Vaynerchuk is closer to Scott Galloway than Joe Rogan. His schtick lands with a generation that's grown up with — and is now exhausted by — social media, which encourages constant comparisons with others. He understands that many young men have fallen behind but aren't necessarily looking for a handout. Rather, they often want a path toward self-reliance.

Vaynerchuk says his brand's softer turn started when he noticed a lot of fear in his DMs.

"I started to realize in probably in 2015 and '16 that there was just a lot more insecurity in the world," he told BI. "I think I took for granted how well I was parented. And that started me to really start to talk about the why, and that got me more into empathy."

Vaynerchuk has also maintained a safe distance from politics, which seems savvy now as some other CEOs clam up to avoid getting caught up in the culture wars.

"I was a no-go when it was much more popular five, seven years ago," he said of talking politics. "I don't trust the American consumer right now in that I just think we're overly emotional. We're very far away from the middle, and so I really couldn't find a way to feel great about it. I care about my employees too much and the thought of doing things that immediately makes half of them not feel good just did not feel right."

Friends float other theories for the gentler Vaynerchuk. He recently went through a divorce (and is now engaged). It's no longer the early days of the internet when you often had to be loud and obnoxious to get hidebound CMOs to pay attention to digital media. Whatever the reasons for the shift, it appears to be a good business move.

"In the beginning, it was, 'That's dumb, that's dumb,'" Jon Halvorson, SVP of Mondelez and a longtime client, said of Vaynerchuk's rhetoric. "I think it's appealing because a good yelling is fun, but people want a consistent partner. I don't want a rock star, I want Ted Lasso."

Can Vaynerchuk stay relevant in the AI age?

Vaynerchuk made a name for himself helping companies jump on social-media trends, but many in the industry are wondering what his next big act will be. CMOs no longer have to be convinced to embrace social media, and many have even bypassed agencies like VaynerX altogether to take that work in-house.

Agencies like VaynerX have had to diversify. Social marketing is still the company's core, but revenue is increasingly driven by other things like consulting and overseas expansion, which the company says now represent 10% and 20% of revenue, respectively. It employs nearly 2,000 employees from New York to Singapore, up from about 800 people in 2019. Vaynerchuk said he sees revenue doubling again in the next five years.

Still, the ad industry is staring down major potential disruption as generative AI threatens to automate a lot of the work agencies do.

As for Vaynerchuk himself, he still bangs the drum about social-media marketing, but his passions have expanded to include Meta's Ray-Bans (Vaynerchuk is an investor in Meta), which he thinks could replace the phone. He's big on live social shopping, which he predicts will blow up next year.

He's also styled himself as something of an AI guru. Vaynerchuk's stance is that business leaders should find a middle ground — staking out a lane that it'd be hard to disagree with.

"Don't demonize it, like we'll never do AI; that's bad for humanity," he said. "Or the other way: 'Oh great, we don't need to do anything else; AI will take care of it.' So let's not get too high on it. Let's not get too low on it."

How the Vaynerchuk flywheel works

Vaynerchuk calls VaynerX the "operating system for everything I do professionally for the rest of my life."

When the Fox streaming service Tubi sought help promoting itself to Gen Z, Vaynerchuk tapped his influencer connections to help. Other work provided the basis for "The Z Suite," a workplace comedy starring Lauren Graham ("Gilmore Girls," "Parenthood") and set at a New York ad agency; Vaynerchuk is executive producing. Empathy Wines grew out of the company. VeeFriends promotes VeeCon, which in turn showcases Vaynerchuk's other businesses. The list goes on.

"He's proven you can take this value of a personal brand and use it to create value in other services," said Brian Morrissey, former president and editor in chief of Digiday and founder of The Rebooting, a newsletter focused on the media industry.

For CMOs, Vaynerchuk's massive social presence and ability to master the platform du jour is a big part of the value he brings.

"The fact he has 10 million followers on Instagram shows he understands how the platform works, so I do put a lot of weight on his recommendations," said Sandeep Seth, chief growth officer of Tapestry and CMO of its Coach brand. "He's not just selling me a theory. So I definitely value that expertise he brings."

Being a CMO can also be a lonely job in the current market — they often have more responsibility and fewer resources to get it done, and their tenures are generally getting shorter — and he's won clients' loyalty by being available. Access to Vaynerchuk's personal network, nice wines, and, for the lucky few, a ride on a Vaynerchuk-chartered plane to industry events like the Forbes CMO Summit doesn't hurt.

"They get CMOs who are interested in a relationship with him," Halvorson said. "It creates a lot of inbound interest."

At a time when household names in advertising like legends David Ogilvy or Leo Burnett are largely gone, Vaynerchuk is something of an anomaly.

"In a world in which tech and data dominate, larger-than-life personalities are increasingly hard to find," said Andrew Essex, former CEO of Droga5 who's now senior managing partner at consulting giant TCS. "For some, a CEO with so much heart might feel anachronistic. Gary is the rare exception who can pull it off."

Is there a Vayner without Vaynerchuk?

The big question for many personality-led companies like Vaynerchuk's is whether they can transcend their leaders.

Walk around VaynerX, and its founder's presence is everywhere, from the framed inspirational quotes on the wall to the conference rooms named after his passions (the New York Jets, Empathy Wines). Naysayers say his personal brand is still bigger than his company; Vaynerchuk has 22 times as many followers on X as VaynerMedia. The agency isn't a huge buyer of TV advertising, which holds it back among marketers of a certain size, nor is it widely considered a destination for big-name execs or a feeder for prestigious marketers like Apple.

Vaynerchuk insists the company is no longer synonymous with him, thanks to the team he's built under him. In fact, he said, the onetime upstart is on such a strong footing now that he now worries about complacency setting in.

"I feel like very senior industry people would consider working at VaynerMedia where seven years ago they would laugh at the idea," he said. "So, I think we are the future establishment."

That's not to say he sees himself letting the place run without him.

Vaynerchuk said he sees himself naming his replacement in five to 10 years, at which point he would move into an active chairman role, running VeeFriends or scratching another longtime itch: buying and reviving bygone brands like Ocean Pacific.

"Could JC Penney's come back in a different form as a social live shopping show?" he mused.

Vaynerchuk prides himself on being a hands-off manager and says he'd let the new CEO run the company. But he won't disappear, either.

"I would just be driving another car, and if that person driving the VaynerX car would like me to come in and sit in the passenger seat and brainstorm some stuff or help, then I'm very there for that," he said.