Gary Vaynerchuk reveals the biggest mistake he made for 20 years

In an interview with Fortune for ‘Champion Mindset’, Vaynerchuk revealed his biggest professional regret: not practicing enough “candor” in managing his employees during the early years of his career.

“The greatest thing I did wrong for 20 years was that I didn’t have good enough candor,” Vaynerchuk admitted.

Despite his public reputation for directness, he said that one-on-one, he often struggled to give honest feedback.

“Even today, I’d say I’m a five out of 10 when I need to tell someone something they need to fix, because I like them too much. I used to think of that [candor] as my superpower, but it’s actually my vulnerability.”

This lack of direct communication, he believes, prevented his employees from realizing their full potential.

“It’s not fair to them if I’m not able to articulate what’s wrong. Then they don’t have the ability to fix it,” he said.

Vaynerchuk now refers to his revised approach as “kind candor,” a balance of compassion and honesty that he considers crucial to effective leadership.

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The entrepreneur, who has a $1 million book deal with Harper Collins and a string of international best-sellers, credits “the market” as his ultimate mentor.

“Customers taught me the most when they didn’t buy my lemonade, and when they did,” Vaynerchuk said.

“The market taught me what it liked and what it didn’t like, and more than anything, that it never stays the same.”

The lessons started young for Vaynerchuk, who grew up selling lemonade and sports cards before transforming his family’s New Jersey wine business into an online giant “Wine Library” generating $60 million in annual revenue, according to his website.

He now oversees multiple businesses through his media companies and recently partnered with CoComelon owner Moonbug Entertainment to create VeeFriends, a 2D-animated series for kids aged 6-11, based on his existing franchise of the same name.

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Vaynerchuk’s leadership philosophy also draws heavily from his upbringing.

His father taught him the importance of integrity, offering what Vaynerchuk considers the best advice he ever received: “Your word is your bond. With my personality and gift of gab, that there was a worse version of myself that was in the cards had I not been parented well, and he tweaked me in an old school way.”

Meanwhile, he credits his mother with teaching him the value of empathy and kindness.

The 48-year-old’s focus on treating people well extended to his views on leadership. “I think I work for my employees,” Vaynerchuk explained, emphasizing humility as a core trait of good leadership.

“I understand I pay their salaries, but I work for them. In return, they work for it [the company logo].”

“I decided I was a success when I was 10”

For all his accomplishments, Vaynerchuk has never been one to rest on his laurels. He credits much of his growth to a mindset developed early on.

“I think I decided I was a success when I was 10,” he said, recognizing early that kindness and competence mattered more than formal education. “I figured out that school doesn’t matter [to me], but being nice and being good at something does.”

Despite his confidence, he never looked to traditional business icons for inspiration.

Instead, Vaynerchuk admired local figures like Richard Salzman, a New Jersey liquor distributor who recently passed away and was both successful and beloved by his employees.

“I hated the idea that nice guys finish last,” Vaynerchuk said. “I was inspired by people who were successful but kind.”

One piece of advice he rejected was the idea that a business must choose between price, selection, and service.

“I was told you can’t do all three,” Vaynerchuk recalled. “I sat there as a 22-year-old and thought, ‘No way, I’m doing all three.’” The result was one of the largest wine stores in the country.

As for what advice he’d offer to others now? Vaynerchuk believes the key to improving one’s life is eliminating negativity.

“You must cut out the most negative person in your life,” he said. Whether it’s a friend, employee, or even a family member, he believes minimizing exposure to toxic influences can have a profound impact on one’s personal and professional well-being.

“If it’s your mother, I would say that you need to limit the exposure. So if you’re talking to your mom, who’s extremely negative, three times a day, you might need to go to three times a week. But if it is not your mother or close relative, and it is a boyfriend that you haven’t married yet, and employee, an employer, you must cut out that cancer.”