Vaynerchuk has theories about leadership, culture and success—and a track record to suggest they’re worth hearing

As seen in Crain's New York Business

To kick off its annual CEO Evolution series, Citrin Cooperman couldn’t possibly have found a more suitable candidate than Gary Vaynerchuk, a widely hailed serial entrepreneur, investor and bestselling author.

The series, a string of seminars featuring notable industry leaders, is hosted by the professional services heavyweight Citrin Cooperman with the goal of providing a platform for those leaders to share the experiences and insights that propelled them to success.

Hosting the inaugural event on Veterans Day was Michael Rhodes, the Assurance Practice Leader for the New York City office of Citrin Cooperman who also leads its technology practice. Rhodes spared no praise in introducing Vaynerchuk, who is a Rhodes client.

“Gary is acclaimed as a leading global mind on what’s next in culture, business and the digital landscape,” Rhodes said. “He’s a forward thinker who recognizes trends early on, as well as how such shifts impact markets.”

Indeed, Vaynerchuk—or GaryVee, as he’s called—is an accomplished angel investor who backed Facebook, Twitter and Uber in their infancies. But he is at heart an entrepreneur who is chairman of his eponymous media and communications holding company VaynerX and CEO of the advertising agency VaynerMedia.

Rhodes began by asking Vaynerchuk how he balances dueling imperatives faced by CEOs everywhere: driving their businesses forward while remaining gracious and likable leaders.

“I do that by leading with emotional intelligence,” Vaynerchuk answered. “I don’t judge others negatively because I don’t judge myself negatively. This idea of being perfect and always correct—it’s a fallacy. Humility is vital.”

Of course, an appreciation of humility need not conflict with having a healthy sense of confidence—something
Vaynerchuk has in spades.

“I’m supremely comfortable in my own skin, with how I do things,” he said. “I don’t do business like most people. For example, I like to run years with little profit. You might think I’m crazy—but I’m confident enough to deal with your ridicule or second-guessing."

Vaynerchuk’s Promethean business instincts were evidenced most recently by his investment in nonfungible tokens in the embryonic stage of that market.

“NFTs came out, I understood them, and I moved quickly,” he said. “And we built one of the most successful NFT projects in the world.”

Crucial to that sort of rapid movement, Vanyerchuk said, is an organizational culture that allows for speedy operations. He contrasts that with the pace of today’s world, which he perceives as intractably sluggish.

“Everyone is overthinking everything, because we’re so divided,” he said. “There’s a lot going on, and there’s tons of fear and hesitation. You can feel the heaviness in the air.”

So how is a CEO to cultivate an environment that allows for nimble responses to evolving conditions?

Vaynerchuk sees a clear chain reaction: “You need to eliminate fear and lead with kindness,” he said. “That builds a positive culture characterized by continuity and retention—which allow an organization to act fast on its feet.”

To Vaynerchuk, these are principles to espouse and live by. In running his numerous businesses, he said, he has
held himself accountable only to his employees—and the man in the mirror.

“It sounds like fluffy stuff,” he conceded. “But I really believe it. I don’t think nice guys finish last. I don’t think being kind means being walked on. To me, a positive culture fostered by a leader with a high emotional quotient is key to success.”

So central are these ideas to Vaynerchuk’s business philosophy that he shares them in a book (his sixth) he recently wrote. Twelve and a Half: Leveraging the Emotional Ingredients Necessary for Business Success will be released Nov. 30.

In the volume, Vaynerchuk, a New York Times bestselling author, describes the emotion-based soft skills he finds integral to business success. Among them are gratitude, self-awareness, patience, optimism, curiosity and conviction.

Vaynerchuk is frank in his telling of the book’s development. “I was alone one time, thinking—I’m always thinking—and I said, ‘OK, tough guy. If you’re so nice and awesome and care so much about your employees, why do some of them not like you?’”

That began an internal probing process that turned up a problem area for Vaynerchuk: candor.

“I realized that I struggle with being candid, and that this had tripped me up in the past,” he explained. “My lack of ‘kind candor,’ as I call it, was breeding fear, because my employees didn’t know where they stood with me. They worried they might be surprise-fired.”

This introspection gave Vaynerchuk a chance to correct this shortcoming—and led to a eureka moment about people in business generally.

“It hit me that we all have traits we excel at and traits we don’t,” he said. “I might be terrible at candor and great with empathy, and you might be the other way around. But if we each work to develop the soft skills that are unnatural to us, the result is a more emotionally intelligent business culture that promotes dynamic operations and, ultimately, long-term success.”

It’s an iconoclastic vision, certainly, but it’s worked for Vaynerchuk. He predicts more businesses will recognize its wisdom in the coming years.

“We’re living through the ‘Great Resignation,’” he said. “Soon young people won’t even be applying to jobs in the first place. Organizations that get serious about creating healthy business cultures are the least likely to get trounced.”

Vaynerchuk’s mission is straightforward: to spark a desire in business executives to lead with kindness.

“I have a robust platform and a compelling voice,” he said. “I want to use them to infuse a measure of humanity into the business world that it hasn’t seen over the last century.