How to Overcome Imposter Syndrome and Start a Business, According to Gary Vee, a Serial Entrepreneur Worth Over $200 Million In an exclusive interview with Entrepreneur, Gary Vaynerchuk shares how to overcome your fears when starting a business.

By Sherin Shibu Edited by Melissa Malamut

Key Takeaways

  • Gary Vaynerchuk, a serial entrepreneur worth over $200 million, shares how to overcome "imposter syndrome" when starting a business.
  • He recently launched vYve, a four-month, $50,000-per-person accelerator program designed for entrepreneurs and corporate leaders.

Starting a business can be risky, especially because half of them fail within the first five years.

But Gary Vaynerchuk, CEO of VaynerMedia, a global company with over 1,200 employees, says that waiting to begin can be worse than failing. Vaynerchuk is a serial entrepreneur worth over $200 million who recently launched vYve, a four-month, $50,000-per-person accelerator program designed for entrepreneurs and corporate leaders.

Related: These Are the Best Cities for Starting a Business — and Surrounding Yourself With Millionaires

In an exclusive interview, Vaynerchuk, who goes by Gary Vee on social media, told Entrepreneur how to get over "imposter syndrome" and get started on your business goals.

What Is Imposter Syndrome?

Vaynerchuk says that fear of the financial risks of starting a business or feeling like an imposter is completely normal.

"Impostor syndrome is just a fancy new word, for you're insecure. And that's allowed. You're allowed to be insecure, Vaynerchuk said. "We've repackaged it."


Gary Vaynerchuk. Photo: Chelsea Guglielmino/Getty Images

Related: What Is Founder Mode? Here's Why the Phrase Is Everywhere.

Insecurity is a feeling that can be overwhelming but can be overcome, he says.

"My advice to someone who wants to start a business is the following: The longer you wait to not do it when you actually are ready to do it, the more it becomes a thing," Vaynerchuk said. "The more you stand at the edge of a pool as a 6-year-old, and fear swimming, the more you wake up like I did, and you're 9, and you're still not swimming. That happened to me because it started to become a thing within itself. So my recommendation is, don't be delusional. Have a plan."

Better Off Trying

Vaynerchuk added that "the biggest thing" to overcoming your fears is taking the leap in the first place.

In other words, you're better off starting a business, failing, and then going back and getting a job than reaching retirement and asking the question, "Why didn't I?"

"'Why didn't I' is the great poison of the back half of all of our lives," Vaynerchuk explained.

The financial fears of entrepreneurship pale in comparison to the regret a person may face by not jumping in at all, he says.

More people may be taking the risk and exploring entrepreneurship. New business applications were at an all-time high last year, with 5.5 million new applications filed.

Related: How a History Student Turned Her Side Hustle Into a Startup That's Raised $7 Million

Sherin Shibu

Entrepreneur Staff

News Reporter

Sherin Shibu is a business news reporter at Entrepreneur.com. She previously worked for PCMag, Business Insider, The Messenger, and ZDNET as a reporter and copyeditor. Her areas of coverage encompass tech, business, strategy, finance, and even space. She is a Columbia University graduate.

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