6 Leaders Who Prove Taking Risks Trumps Playing It Safe

| September 28, 2016 | By

“Only those who risk going too far can possibly find out how far one can go.” –T.S. Eliot

A great quote, but easier said than done, right?

Taking risks comes more naturally to some than to others, and for many of us gambling seems more suited to the poker table than the conference room. When it comes to building a business, though, there’s no chance of massive success without a healthy dose of risk.

If you need a little inspiration to make that big move you’ve been contemplating, here are six iconic leaders who stepped off the edge and into the unknown—and for them, it paid off big time.

Elon Musk


America hadn’t had a new major automobile manufacturer in at least five decades… that is, until Elon Musk came along.

Launching an energy efficient car company in a nation dependent on oil was risky enough, but Musk’s operation, Tesla Motors, came of age just as America began its slide into the worst recession in modern history. By 2008 the company was out of cash and unable to deliver its first vehicle.

Taking a major leap of faith, Musk took $35 million of his own money—the last reserve he had—and pumped it into Telsa. At the time, he says he was living purely off of loans from friends amid glaring media headlines that he was broke.

Eight years later, it’s clear Musk’s big gamble paid off. Latest reports value Tesla at $36.7 billion, a number that’s expected to soar even higher over the next decade.

Brian Chesky, Joe Gebbia


What would you do if you were so broke you could no longer afford your rent? In 2007, that was the situation San Francisco designers Brian Chesky and Joe Gebbia found themselves in.

Their solution? Open their doors and let strangers sleep on their floor for cash. Remember this is 2007, well before renting out space in other people’s homes hit the mainstream.

Chesky and Gebbia’s unusual risk netted them $240 in one weekend, and they knew they were onto something. They poured everything they had into this groundbreaking idea, which would eventually develop into the crowdsourced lodging platform AirBnb.

Arianna Huffington


Her name has become a household media staple, but it wasn’t always that way for Arianna Huffington, founder of the Huffington post.

In 2005 when the news aggregator site launched, Silicon Valley and the tech scene in general were largely dominated by men. Even so, Huffington placed her bet on her biggest asset—herself.

“At some point, I learned not to dread failure,” she told Fast Company. “I strongly believe that we are not put on this Earth just to accumulate victories and trophies and avoid failures; but rather to be whittled and sandpapered down until what’s left is who we truly are."

Despite initial opposition (one reviewer called the news outlet the website equivalent of the blockbuster flop ‘Gigli’), the Huffington Post has gone on to become one the most visited sites on the internet and trusted news sources the world over.

Larry Ellison


If you don’t follow the tech and software industries, you might not be as familiar with the name Larry Ellison as, say, Bill Gates or Steve Jobs. But Ellison is just as successful (and just as wealthy) as both Gates and Jobs as the co-founder of Oracle Corporation, and even more of a risk-taker.

In fact, Ellison is perhaps the most extreme model of the dance between risk and reward in business. He’s known for promising features that don’t yet exist, then going back to his development team to demand that they be built. He’s also been widely criticized for his mercurial tendencies, like hiring managers that are clearly unqualified and training them on the spot to do the job.

Though his playboy lifestyle of fast cars and fancy yachts might not be for everyone, there’s no denying that Ellison’s big business gambles have paid off, at least in the long run. Oracle today has more than 130,000 employees and an annual revenue of $37 billion.

J.K. Rowling


The beloved Harry, Ron and Hermione wouldn’t exist without J.K. Rowling, but would you ever have guessed that this world-renowned author was once on welfare?

After a failed marriage, J.K. Rowling moved herself and her daughter to Edinburgh, Scotland with little more than the clothes on their backs. Most of us would have taken any job we could find to put food on the table, but Rowling decided the time was now or never to pursue her lifelong dream of becoming a writer.

Though she describes herself as being “as poor as you could possibly be without being homeless,” Rowling spent the next few years hammering out the manuscript that would in 1997 become the first Harry Potter book.

In 2011 Rowling was included on Forbes’ list of the world’s billionaires, but has since dropped from the list after contributing a large portion of her fortune to charity.

When you read the stories of those who gambled everything they had on their business and won, suddenly the small day-to-day risks involved in running your company don’t seem so earth shattering.

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