How to Start a Business, Even When You Are Afraid - Gary Vee

Starting a business can be intimidating—there’s no doubt about that. You’ve probably heard the statistics: about half of all businesses haven’t made it past five years. But for Gary Vaynerchuk, a serial entrepreneur worth over $200 million, the biggest risk isn’t failing—it’s not starting at all.

Gary, or Gary Vee as he’s known on social media, is the CEO of VaynerMedia, a global company with more than 1,200 employees. He recently launched vYve, a four-month accelerator program that helps entrepreneurs and corporate leaders take their businesses to the next level. Each participant invests $50,000, but the lessons Gary shares are priceless.

In an interview with Entrepreneur, Gary Vee offered some straightforward advice on overcoming imposter syndrome—something most of us have felt at one time or another. Let’s dive into what he had to say.

What Is Imposter Syndrome Anyway?

Gary doesn’t mince words: “Imposter syndrome is just a fancy new term for insecurity,” he says. And you know what? That’s totally normal. We’ve all had those moments of self-doubt, wondering, Am I really good enough to do this? But here’s the thing—feeling like an imposter doesn’t mean you aren’t capable.

He compared it to a personal childhood experience. “The more you stand at the edge of a pool and fear swimming, the harder it gets. I waited until I was nine years old to learn because I let that fear build up over time.” His message? Don’t let your doubts grow into something bigger than they really are. If you’ve got a plan and the desire, then jump in and get started.

Better to Try and Fail Than to Never Try

One of the most powerful points Gary makes is that regret weighs heavier than failure. He believes the fear of failure is far less painful than living with the question, Why didn’t I try?

“The great poison of life is wondering, Why didn’t I?,” he explains. In other words, it’s better to start a business, fail, and then find another job, than to retire with regrets. Financial fears, while valid, shouldn’t hold you back from pursuing your dreams.

The Time Is Now

Starting a business is a bold move, but Gary Vee’s advice makes one thing clear: the longer you wait, the harder it gets. Overcoming imposter syndrome isn’t about waiting until you feel 100% ready (spoiler: you never will). It’s about taking that first step, even if it feels scary.

And the numbers show that more and more people are taking that leap. In fact, last year saw a record 5.5 million new business applications. So why not you?

Ask yourself, what’s scarier—failing or never knowing what could have been? If you’re leaning towards the latter, it might be time to take the plunge.

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