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Gary Vaynerchuk Shares His 20-Year Biggest Mistake

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Gary Vaynerchuk, a prominent entrepreneur, best-selling author, and public speaker, has established his VaynerMedia empire with straightforward communication and keen sales instincts. However, he disclosed that he did not always leverage his “superpower” effectively during the initial stages of his career.

In an interview with Fortune for the ‘Champion Mindset’ series, Vaynerchuk expressed his greatest professional regret: not exercising enough “candor” when managing his employees in the early part of his career.

“For 20 years, my biggest mistake was lacking adequate candor,” Vaynerchuk admitted. Despite his reputation for directness, he revealed that he often struggled to provide honest feedback in one-on-one situations.

“Even now, I’d rate myself a five out of ten in terms of telling someone what they need to fix because I like them too much. I once thought of candor as my superpower, but it’s actually my vulnerability,” he stated. He believes that this lack of direct communication hindered his employees from reaching their full potential.

“It’s unfair to my employees if I can’t articulate what’s wrong. It deprives them of the opportunity to correct it,” he explained.

Vaynerchuk has since adopted what he calls “kind candor,” a blend of compassion and honesty he deems essential for effective leadership.

Regarding his mentors, Vaynerchuk, who has secured a $1 million book deal with Harper Collins and boasts several international bestsellers, credits “the market” as his paramount mentor. He explained that his customers taught him the most, both when they purchased and when they didn’t buy his lemonade, highlighting that the market’s preferences are constantly evolving.

Vaynerchuk began learning these pivotal lessons early in life, starting with selling lemonade and sports cards and eventually transforming his family’s wine business, Wine Library, into a $60 million enterprise. He currently manages multiple businesses through his media companies and has recently collaborated with Moonbug Entertainment to produce “VeeFriends,” a 2D-animated series for children based on his existing franchise.

Vaynerchuk’s leadership ethos is significantly influenced by his upbringing. His father impressed upon him the importance of integrity, advising that “Your word is your bond.” This counsel was crucial in preventing Vaynerchuk from taking an unprincipled path given his charismatic personality. His mother, on the other hand, instilled in him the values of empathy and kindness.

He emphasized that his leadership style centers on service to his employees. “I believe I work for my employees,” Vaynerchuk said, stressing humility as a fundamental element of leadership. “I understand I pay their salaries, but I work for them. In return, they work for the company.”

Reflecting on his success, Vaynerchuk revealed that he considered himself successful from the age of 10, having realized early on that kindness and competence were more critical than formal education. He admired local business figures like Richard Salzman, a well-respected New Jersey liquor distributor, over traditional business icons, disliking the notion that kind individuals finish last.

One particular piece of traditional business advice he rejected was the belief that a business must choose between price, selection, and service. “I was told you can’t do all three,” Vaynerchuk recalled. “As a 22-year-old, I thought, ‘No way, I’m doing all three.’” This determination contributed to the creation of one of the largest wine stores in the country.

For those seeking to enhance their lives, Vaynerchuk advises eliminating negativity. He advocates for distancing oneself from negative influences, whether they are friends, employees, or even family members. Vaynerchuk emphasized the significant impact that reducing exposure to toxic individuals can have on one’s personal and professional well-being.

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