By its very nature, embarking on a new business venture requires not only capital investment, but also passionate commitment to a vision. Whether spearheading an early-stage startup that's grappling for a foothold in a competitive market or capping off another $100 million revenue quarter, all entrepreneurs share one unifying quality: the willingness to take game-changing risks. Despite spanning industries from tech to fashion, these five business moguls have all demonstrated a fearless pursuit of excellence in the face of intimidating odds.

1. Arianna Huffington

As the founder of one of the first and most commercially successful online news publications, the Huffington Post, as well as the health and wellness project Thrive, Arianna Huffington has always been a self-starter. She studied economics at the University of Cambridge, and by 2005 had penned a number of successful books, starred in a TV show, and built a career as a successful journalist.

When she proposed launching a new media platform, she was discouraged by naysayers even within her own family, who warned her to be wary of failure. Instead, she put in the hard work to gain investor buy-in and build the first opinion-based online news outlet of its kind.

When it comes to risk-taking, she has encouraged entrepreneurs to move past their fear of failure, saying, "Failure is not the opposite of success -- it is the stepping stone to success. For anyone who is an entrepreneur, that is perhaps the most important lesson."

2. Mark Cuban

A graduate of Indiana University's Kelley School of Business, Mark Cuban is a businessman and serial entrepreneur. Before becoming the owner of the NBA's Dallas Mavericks and one of the faces of Shark Tank -- an ABC reality show offering budding entrepreneurs the chance to pitch to industry titans for major investment deals -- Cuban launched a number of technology companies. Today, he holds assets across the social software and distributed networking sectors and serves as the president and CEO of the television network AXS TV.

While Cuban acknowledges that risk-taking is a crucial component of launching a thriving business, his relationship with risk is an adversarial one: "I hate risk," he told CreativeLive. "I'm terrified of it." His key to success, then, is mitigating that risk with thorough preparation. He is committed to conducting comprehensive market research and staying on top of industry trends in order to avoid becoming one of the 50% of small businesses that fail within their first five years of operation. By learning everything he could about the industries in which he invested, he was able to take only the most calculated risks. "I was relentless about learning," Cuban has said.

3. Oprah Winfrey

Perhaps the most successful woman entrepreneur in the world, Oprah Winfrey has created a multimedia brand legacy and launched multiple philanthropic organizations during the course of her career. With her own television network and media empire, Winfrey's focus on literature, spirituality, and self-improvement has paved the way for a new era of confessional media. Today, she is the only African-American woman on Forbes' 2018 Billionaires list, with a net worth nearing $3 billion.

Winfrey has fought tooth and nail for every bit of her success. Following a turbulent and impoverished childhood in Mississippi and Wisconsin, Winfrey received a full scholarship to Tennessee State University, and eventually broke into the TV and radio journalism industry. It wasn't until the mid-80s that she decided to risk her financial security by signing a deal to host her own television program. The Oprah Winfrey Show went on to become the highest rated program of its kind in history.

Winfrey proves that measured risk-taking can yield great reward -- even if it takes a few tries: "Do the one thing you think you cannot do. Fail at it. Try again. Do better the second time. The only people who never tumble are those who never mount the high wire," she said.

4. Jeff Bezos

Unlike Winfrey, Jeff Bezos didn't have to take a risk -- the Princeton University graduate had secured a high-paying job on Wall Street as the senior vice president of hedge fund D.E. Shaw & Co. However, Bezos felt called to entrepreneurship. In 1994, he risked it all by sacrificing his job in finance to found Amazon, which began as an online bookstore run out of his garage. Today, he also heads the spaceflight company Blue Origin, and is the wealthiest man in the world, with a net worth over $160 billion.

"For me," Bezos has said, "I had to project myself forward to age 80. I don't want to be 80 years old, cataloging a bunch of major regrets of my life." By minimizing his 'what ifs,' Bezos' extraordinary story demonstrates how taking a leap of faith can lead to staggering successes.

5. Vera Wang

The daughter of Chinese immigrants, Vera Wang attended the University of Paris and received a degree in art history from Sarah Lawrence College. She was hired as an editor for Vogue immediately out of college, becoming the publication's youngest editor. After 17 years with the magazine, Wang joined Ralph Lauren. It wasn't until she was 40 years old that she took her big risk: she sacrificed her financially stable career working for a top designer to launch her own label.

As a trailblazer, Wang offers encouragement to entrepreneurs who don't fit the stereotype of the young, tech world type. At the 2013 CFDA Fashion Awards, where she received a lifetime achievement award, she said, "I didn't come into this like all these teenagers who don't know better. I wasn't a 'young, new designer' -- but I was a new designer and had to go through those growing pains. The risks were apparent to me."

The risks were well worth it in the end: today, Wang is regarded as one of the most prestigious American fashion designers, having designed custom gowns for high-profile clientele including Michelle Obama, Alicia Keys, and Kim Kardashian.

How to Make Failures Work for You

These wildly successful entrepreneurs are living proof that success is not about being risk-aversive or about taking uncalculated risks. Success lies somewhere between the two. To future-proof your company from disruption, you're going to have to take some risks - and make some mistakes along the way. When you stumble, knowing how to make your failures work for you will get you out of the slump, even propel you to the next level of possibility and success.

Published on: Oct 3, 2018
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