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The Fast Company Executive Board is a private, fee-based network of influential leaders, experts, executives, and entrepreneurs who share their insights with our audience.

How to make fear your friend and risk your ride-or-die

It’s a process—failing in the right order to get to the right destination.

How to make fear your friend and risk your ride-or-die
[Zenzeta / Adobe Stock]

Why do we fear fear? There’s the reality of fear for our survival, and then there’s the fear tangled up in the potential of the unknown. It’s that uncertainty before stepping on stage, running onto the field, or starting your own business. We can let fear dampen our spirits, or we can use it to spur us through risk to new heights.

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To be successful as a leader or entrepreneur, you need to recognize fear across your stakeholders. For employees: “Am I going to make it here?” or “Are we going to make it here?” For customers: “Is this a fair exchange of my money for these goods or services?” For investors: “Does the potential reward outweigh the risk?”

They’re all important to address but in different ways. It’s hard to operate without investors. It’s impossible without customers or employees. I focus my energy first on employees because they’re helping drive the vision that gains the attention and trust of those other stakeholders. But before you can ever hope to manage the fears of others, you have to face your own anxiety related to trying something new.

EVER THE OPTIMIST

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Fear is a powerful emotion requiring an equally potent countervailing energy. For me, that’s optimism. As a serial entrepreneur, I’ve found it useful to have that positive energy to avoid dwelling in doubt.

You also need a trailblazing mindset—a passion for discovery. When risk and its attending fear arrive on the scene, I work on staying grounded. In my entrepreneurial adventures, I’m like a parent who is excited about the birth of an idea with the desire to counsel it, support it, and watch it “grow up.”

I work to share that enthusiasm with the people on this journey with me because they’re dedicating a portion of themselves to help me pursue my dream. I’m obligated, when concerns do arise, to slow the conversation for both of us. I reiterate purpose, process, and goals, and ask a series of questions to level-set whether they feel capable and supported and agree we’re moving in the right direction.

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It’s an exercise that can be adapted to address customer or investor concerns. But it also serves as a check for me on where things stand outside of my own thinking. I’ve learned that, with data, I can take the right steps to address unproductive fear and mitigate risk.

TEST, LEARN, REPEAT

In many ways, managing risk comes down to resource allocation. It’s a careful balance between perceived risk, measurement, adjustment, and reallocation that works on a constant feedback loop, incrementing toward a goal. How you calculate allocations may start intuitively, but one of the best ways to offset risk is to continually test and learn.

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Identify your hypothesis. What are you trying to prove? What’s a statistically significant test to examine your own belief, disbelief, or whether there’s substance to your hypothesis? This scientific approach applies to anything from price setting to messaging to feature expansion. When resources are particularly finite, it’s critical for determining the best use of both your financial and human capital.

Good entrepreneurs find a balance between intuition and information. Good leaders create a culture where everybody is open to sharing ideas for testing and there is abundant transparency around the purpose, process, decision-makers, and next steps. In an organization that values learning, you know you’re all working from the same information driving toward the same goal.

That sounds obvious now, at 53. When I was 27, I thought information was a transactional business tactic—withhold from some and share with select others. Now I’m more focused on getting to the right result. I have few regrets about my path, but I wish I’d understood and implemented a test-and-learn environment earlier.

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There will always be voices telling you your idea is flawed or risky. Listen to your instincts and don’t assume someone else’s perspective has more authority or value than your own. Push ahead so you can adjust your intention, energy, and resources as needed with actual proof.

GETTING TO WHERE YOU NEED TO BE

Don’t confuse numbers with know-how, however. The USCB reported 5.4 million new businesses in 2021 and the U.S. BLS says nearly one in five U.S. businesses fail within the first year. If entrepreneurs balked in the face of that data, we’d never innovate. You have to address fear and understand how to fail, get to safety, then go again. You have to be okay with the idea of failure as an integral part of the journey.

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Through my own journey, I developed a leadership model focusing on integrity, discipline, respect, and empathy. If I’m at a company that operates with integrity, I know I’ll be treated properly. Discipline is about doing things the same way—the right way—and using a test-and-learn approach accomplishes that. Respect is about recognizing the value of finite resources and allocating appropriately, and empathy relates to the idea of emotional intelligence (EQ) and meeting people where they are.

My ability to garner loyalty from employees is due to my ability to recognize, understand, and respect their needs. It’s core to who I am, but I’ve also learned to expand my EQ and practice it every day. I don’t think I would have come as far as I have without it. Operating under these principles demonstrates my values so that customers and investors alike feel there’s less risk and are thus less fearful to engage.

Jazz music legend Miles Davis once said, “Do not fear mistakes. There are none.” It’s a succinct summary of my thinking around managing risk and fear as an entrepreneur. People go into business and think it’s a series of successes. The truth is it’s a series of failures.

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You have to see those failures for what they are, otherwise you’re not doing justice to the opportunity before you. It’s a process—failing in the right order to get to the right destination. So those stumbles are not mistakes for you to fear. They’re the stepping stones to your success.


Founder & CEO of SquadLocker, a provider of innovative online tools to ease athletic apparel purchasing for leagues, teams, and schools. 

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