Going against the flow. Thinking outside the box. Believing in an idea. These are the hallmarks of the fearless entrepreneur, whose ability to thrive outside their comfort zone takes them further than their more fearful contemporaries and enables them to make things happen. But where does this fearlessness come from? Are people born with it, or can it be acquired?
Virgin founder Richard Branson is known for his appetite for taking risks and innovating, and for his bravery in venturing boldly into new markets, despite overwhelming competition. “For good or bad, I have always lived by the mantra that the brave may not live forever, but the cautious do not live at all,” he says.
One of the most audacious risks he ever took was launching Virgin Atlantic. With no experience in aviation or an industry dominated by established giants like British Airways, it was no mean feat. “We were a record label; what did we know about planes?” he says. “But we saw an opportunity to shake up a dull industry and offer something better. We started with just one plane and a simple idea: to make flying more enjoyable.”
The challenges were enormous, from securing licenses to competing against much larger operators on the world’s most competitive air corridor. He admits there were moments when it seemed the odds were stacked against them, but he never gave up on his belief in taking calculated risks and trusting his instincts. He says: “That risk opened the door to new ventures and showed me that bold moves can lead to great success, as long as you protect the downside and stay focused on the problem you’re trying to solve.”
Nature or nurture?
Still, it begs the question, where does that fearlessness come from? In Branson’s case, it was the influence of his mother, Eve Branson, an adventurer herself, who pushed him to be brave from a young age. “She taught us that growth happens outside of your comfort zone; you learn by doing and falling over,” he says. “Mistakes are part of the journey, and they teach you more than success ever will. That’s shaped how I’ve approached life and business; always willing to take a leap, trusting that I’ll figure it out along the way.”
Being fearless isn’t about ignoring fear, it’s about managing it, and a big part of that comes down to taking calculated risks. Branson says: “I’ve always believed in protecting the downside, thinking through what could go wrong and how to limit the damage. That’s the smart way to approach risk. At the same time, trusting your instinct is key. If something feels right, even when the odds are tough, I’m a believer in going for it.”
For entrepreneurs, decision-making that is driven by fear can mean missed opportunities, failure to reach their full business potential and delayed decisions that could cost them a crucial investment. Everyone feels fear. It is a human instinct that keeps us safe, however, successful entrepreneurs can learn to push through it.
Learning fearlessness
Business coach Agnes Cserhati, author of The Performance Advantage, has worked with many entrepreneurs who were initially held back by fear of failure, but with the right mindset, have successfully turned that fear into fuel.
She says: “Entrepreneurial success lives outside the comfort zone; however, being fearless is not the answer. I like to call it being ‘brave’: it is not about the absence of fear, but about doing it despite it. The difference between those who manage fear and those overwhelmed by it often comes down to how they perceive failure.
“Those who view failure as a learning opportunity are less likely to fear future risks. They understand that failure is an inevitable part of growth and progress. However, if failure is internalized as a personal flaw or a sign of incompetence, it can make someone more cautious or hesitant or even get you stuck.”
Thinking differently
For some, an innate ability to think differently, and therefore to approach risk in a way that others don’t, can be an advantage when the stakes are high.
Daniel Singer, founder of Filthy Food, believes that his mission as an entrepreneur is to dream, to break and build things, to challenge and to push. A quiet life has never been on his agenda. The U.K. native transitioned from a career as an actor with the Royal Shakespeare Company, a career that requires high levels of resilience and fearlessness, to founding his business from a standing start and becoming an influential member of the global spirits community and key cocktail industry innovator.
He is also a dyslexic thinker, a strength that he says allows him to see the space between the noise and identify opportunities where others may see clutter.
“I’ve learned to trust how I see the world around me and commit fully to those strong instincts,” he says. “My choices are fueled by a strong personal belief that my involvement will affect positive change. I’m an instinct-driven entrepreneur, so I don’t think in terms of more risk for more reward, as an investor might. I saw an opportunity to put love into a category that was devoid of it, and that instinct became an obsession that has shaped my life.”
The age factor
Others argue that age and life stages are factors in the way that entrepreneurs manage fear and risk in business. Dicky Broadhurst, founder of The Present King has experienced the highs of building a business from nothing to a £2 million turnover and the lows of its collapse. He started that business, which sold personalized greeting cards containing chocolate messages, at 32 and says he felt very little fear, only possibility.
Today, at 42, with a family to support, he is building a new business where the stakes are higher, and the fear is real. “Running it on my own took a toll on me and my family,” says Broadhurst. “After a COVID-driven boom, I invested the profits into a new website. What started as a £15,000, five-week project, quickly spiraled into a £50,000, four-month ordeal. The site went live just as online shopping interest deflated. Bigger overheads combined with reduced revenue forced me to sell the business with no material gain.”
Unlike his previous business, The Present King is a marketplace, requiring lower initial capital but more investment to scale. Broadhurst admits to being more cautious this time around. He says: “Managing fear during this time has been challenging. Without a steady income, stress levels rise, and the fear of failure creeps in. Add a touch of imposter syndrome, and the whole thing can feel overwhelming. Finding financial stability, a supportive network, and people to talk to makes managing fear easier; though I haven’t fully taken my own advice yet!”
The advice from Richard Branson to other entrepreneurs looking to bolster their fearlessness is to start with small risks and build confidence from there. He says: “Surround yourself with a great team, learn from failure, and remember: the biggest risk is never trying. Ask yourself, what’s the worst that could happen? Fear of regret is often bigger than the fear of failure. You’ll never know until you try.”
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