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Why Risk-Takers Make the Big Bucks Apple's Tim Cook has never launched a company, yet he is a far bigger risk taker than many who revel in calling themselves entrepreneurs.

By Steve Tobak Edited by Dan Bova

Opinions expressed by Entrepreneur contributors are their own.

REUTERS | Stephen Lam

What's more exciting, a cross-country skier trudging across the terrain or a downhill racer risking life and limb at 90 miles per hour? Of course it's the latter, and that's why we watch.

Even in professional sports like tennis where physical injuries rarely occur, it takes guts to compete with millions watching and everything on the line, not to mention the drama of two athletes competing head to head to win.

No risk, no reward. It's the same in business. And let me tell you something, folks. Just because you call yourself an entrepreneur, doesn't make you a bigger risk-taker than a company employee.

Take the CEO of a public company, for example. It was just as risky for Tim Cook to get up on stage and bet big on the Apple Watch as it was for Steve Jobs to go up against Big Blue with Apple's groundbreaking "1984" Super Bowl ad 30 years earlier.

That was not the first time Cook took a flying leap. In 1994, he gave up a 12-year career at IBM to become an executive at computer distributor Intelligent Electronics. When the company unraveled, he joined Compaq, the world's largest PC maker, but left after just six months to help Jobs turn around struggling Apple.

In 2013, Cook decided to risk a third of his compensation on Apple's performance versus the rest of the S&P 500 over an eight-year period. Make no mistake, there's no upside and no small print. He simply chose to lead by example and forfeit what amounts to more than $100 million if the company under performs.

The following year, Cook, who grew up in a working class family in the south, became the first Fortune 500 CEO to publicly come out as gay. The man has guts, I can tell you that. That willingness to put his own butt on the line and hold himself accountable is why he now runs the most valuable technology company on Earth.

There are very few Tim Cook's in the world; far fewer than you probably realize.

Related: Apple's Tim Cook on Leadership: 'The Most Important Data Points Are People'

The vast majority of people follow the path of least resistance and lowest risk. That's precisely why so few take big chances, accomplish great things and make the big bucks. That's as true today as it ever was, but you'd never know it from the way we represent ourselves online.

If you believe our profiles, we're all entrepreneurs, leaders, CEOs, investors, best-selling authors, award-winning speakers, experts, gurus -- the absolute greatest thing since Bill Johnson shocked the world by becoming the first American male to win a gold medal in alpine skiing at the 1984 Winter Olympics.

But here's the thing. You don't get to decide how successful you are. The market alone makes that determination. No matter what label you decide to bestow upon yourself, until you take some serious risks and the market decides you're as valuable as you think you are, you haven't proven a thing and the rewards won't follow.

I know a lot of you think of yourselves as entrepreneurs when, in reality, you're just self-employed or solopreneurs, as it were. Not only is that not the same thing, it's not even in the same ballpark. And if you dream of making it big someday, or at least becoming financially secure, I'm afraid you're in for a rude awakening and I'll tell you why.

You're simply not putting enough on the line to expect that kind of return.

Related: Bill Gates Says Apple Should Cooperate With the FBI

You could argue that opting to go it alone instead of working a full-time job is taking a risk, and maybe that's true. But I suspect it's just as likely that you've chosen a lifestyle with the perceived benefits of being your own boss, ruling your own destiny and having the flexibility to do what you want, when you want.

If that's the case, you've actually chosen the past of least resistance and, in practical terms, that's more or less the same thing as low risk. That's all well and good, but I wouldn't expect anyone to throw you a parade and bestow riches upon you. The tradeoff between risk and reward is very clear about that.

Look at it this way. The day you call yourself an entrepreneur, a leader, a CEO, an expert, whatever, is the day you give yourself a label, and that's all it is. It's the day you call yourself a downhill racer before putting on your first pair of skis.

Cook may never have founded a company, but that doesn't make him any less of a risk-taker than those who do. Even though you work for someone else, if you put yourself out there, take big chances, and hold yourself accountable to be the best at what you do, the risk-reward tradeoff will go your way.

The irony is, a lot of people who work for others are far bigger risk-takers than those who think of themselves as entrepreneurs. And they're also far more likely to reap the rewards.

Related: 5 Things You Don't Know About Apple CEO Tim Cook

For more on what it takes to become a successful entrepreneur and an exceptional leader in today's highly competitive business world, get Steve's new book, Real Leaders Don't Follow: Being Extraordinary in the Age of the Entrepreneur, and check out his blog at

Steve Tobak

Author and Managing Partner, Invisor Consulting

Steve Tobak is a management consultant, columnist, former senior executive, and author of Real Leaders Don’t Follow: Being Extraordinary in the Age of the Entrepreneur (Entrepreneur Press, October 2015). Tobak runs Silicon Valley-based Invisor Consulting and blogs at, where you can contact him and learn more.

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