receives compensation from some of the companies listed on this page. Advertising Disclosure


Unlikely Role Models: Five Entrepreneurs You Shouldn’t Love but Do

Deborah Sweeney
Deborah Sweeney

There are plenty of high-profile entrepreneurs, like Richard Branson or Marissa Mayer, looked to by business owners as obvious role models. Men and women who are kind, generous, intelligent, and all around great people.

But then there are the entrepreneurs that you probably shouldn’t look to, but do anyway. Entrepreneurs that succeed in spite of their lack of business acumen or interpersonal skill.

According to the Entrepreneurial Aptitude Test, the four most common traits for successful entrepreneurs to have are hearts, smarts, guts, and luck. And these five are smart, dedicated, and brazen—perhaps to a fault. They’ve certainly made their fair share of enemies and detractors. Nevertheless, there is just something magnetic that attracts people to them and turns them into role models.

Steve Jobs being interviewed

1. Steve Jobs

Jobs was, in no uncertain terms, a visionary and that’s undoubtedly why he’s a role-model. But Jobs wasn’t a great businessperson. He demanded perfection, and isolated people he disagreed with.

Apple’s CEO John Sculley famously ousted Jobs from Apple in the eighties after they butted heads about the company’s direction. Jobs' notoriously high demands crippled NeXT, which he founded after leaving Apple, and he attempted to divest himself of Pixar before it became a production powerhouse because it struggled to sell hardware.

But despite that lack of practical business skill, his amazing vision and intellect did, eventually, bring Apple back from the brink, and it’s hard not to respect the man’s foresight and passion.

Related Article: Who is the Next Bill Gates or Steve Jobs?

Kris Jenner
Kris Jenner

2. Kris Jenner

Regardless of what people think about ‘Keeping Up with the Kardashians,’ the rise of Jenner’s $100-million media empire was not accidental. She is the queen of turning lemons into lemonade; a quality that rubs some people the wrong way.

After all, she’s building a business around publicly displaying her family’s problems and frustrations. And yet so few can look away as Kris continues to expand her family’s brand. Whenever she sees an opportunity, she’s more than happy to pounce and use it as fully as possible. Her seemingly unshakeable ability to pivot on a dime and solve problems is exactly what makes her a role model.

Jeff Bezos

3. Jeff Bezos

Bezos used to be a likely role model, but a few shaky decisions have turned some people off of Amazon’s Founder. Bezos bet, and lost, a lot on Amazon Fire, and the recent decision to ban Apply TV and Chromecast from Amazon because they don’t support Prime feels almost petty.

But Bezos is the sort of person who likes to experiment and push boundaries, and he’s willing to do nearly anything to protect facets of Amazon he feels keep the company relevant. Bezos is smart enough to see an end and willing to do whatever it takes to get there. That’s exactly how a company selling books online and shipping out of a garage became America’s largest internet retailer.

Related Article: The End of "Rank and Yank": Management Practices, Revisited

Travis Kalanick
Travis Kalanick

4. Travis Kalanick

Kalanick has entrenched himself in Uber’s assault on the taxicab industry, often criticizing and mocking agencies and lawmakers trying to ban his company.

But he’s also all too willing to thrown some of that venom towards his customers and drivers whenever he feels like they’re attacking Uber. Kalanick is gutsy to a fault, and that brazen attitude upsets plenty of people.

Legitimate complaints about exploitive pricing and business practices should never be taken lightly. But it’s hard not to respect what he built, and his unwavering dedication to his company.

Donald Trump
Donald Trump

5. Donald Trump

A list on controversial entrepreneurial role models would be incomplete without Donald Trump. The man makes ugly, reprehensible comments seemingly whenever a microphone is put to him. And yet his draw is undeniable. He’s confident, perhaps to a fault.

But a bit of overconfidence is a trait entrepreneurs know well—a Kauffman Foundation study found 91 percent of entrepreneurs they surveyed were confident their company would continue to grow. Trump has dealt with more than his share of bankruptcy proceedings and failed ventures, and yet his confidence in himself is unflappable. It’s exactly that unwavering, unshakable confidence that repulses, and attracts, so many people.

When people think of role models, they’re minds normally turn to paragons of the industry, yet all five of the entrepreneurial role models on this list are far from perfect. They make unsound business choices or act in ways that baffle the average person.

But that is exactly why they’re useful role models, as every entrepreneur faces their small failings and imperfection. And while you certainly shouldn’t mirror the behavior of some of those on this list—especially when it comes to Donald Trump—their weaknesses, as well as their strengths, are what make them role models.

Image via Wikipedia

Image Credit: Monkeybusinessimages / Getty Images
Deborah Sweeney
Deborah Sweeney Member
Deborah Sweeney is the CEO of MyCorporation is a leader in online legal filing services for entrepreneurs and businesses, providing start-up bundles that include corporation and LLC formation, registered agent, DBA, and trademark & copyright filing services. MyCorporation does all the work, making the business formation and maintenance quick and painless, so business owners can focus on what they do best. Follow her on Google+ and on Twitter @deborahsweeney and @mycorporation.