4 Successful Entrepreneurs Who Will Inspire You to Push Past Failure


When you get stuck in a rut, it’s difficult to believe that anything good can come from the experience. However, there are people who endured epic moments of failure but who ultimately succeeded, and these people started out just like you – aspiring or new entrepreneurs fighting to find their footing.

Here are the stories of five famous entrepreneurs who faced setbacks and how they overcame them for a better victory:

Adam Pisoni

Right after dropping out of high school, Adam Pisoni enrolled into Scottsdale College because he wanted a more challenging academic experience. However, he left college when he came to the decision that he was ready to start his own business.

His innocent enthusiasm led him to launch two endeavors that didn’t last long, so he threw himself into building Cnation, a web-design company. Working 100 hours a week and rallying clients with his passion allowed him to succeed quickly. But when the dotcom crisis hit, many of his customers were forced to shut down or cut expenses, which eventually caused Cnation to close. Heartbroken, Pisoni fell into depression and went to work at a snowboard shop for three years.

Yet Pisoni’s story didn’t end there. As social media swept the nation for the first time, he came up with the idea to start a business centered on facilitating collaboration and connection within companies. Thus was born Yammer, which he co-founded with David Sacks.

This time around, Pisoni wasn’t as discouraged when his business wasn’t immediately successful. Even when 20 competitors emerged within the first year, he put his nose to the grindstone and pushed forward until Yammer became an established, thriving company. In fact, he admitted that he had learned a valuable lesson over the years:

“I think there’s a cognitive dissonance that an entrepreneur has to hold in their head—irrational belief in the outlook of success with a rational fear of failure. I think that’s a big part of being an entrepreneur.”

Arianna Huffington

What a lot of people don’t know about Arianna Huffington is that before she created the wildly successful Huffington Post, she wrote a book that got rejected 36 times before being published. And when she did finally start her own business, she fell into a pattern of working 18 hour days and deprived herself of sleep to achieve more money and power.

Huffington’s wake-up call came when she passed out from fatigue and broke her cheekbone. After that incident, she came to the conclusion that just pursuing money and power without any boundaries or lifestyle balance was destructive. Motivated to change, Huffington began to encourage healthy work practices within her companies so that her employees could enjoy healthier lives. In addition, she published a book called Thrive, which broke down the importance of focusing on relationships and overall happiness.

To sum up her experience with failure, Huffington stated, “Fearlessness is not the absence of fear. It’s the mastery of fear. It’s about getting up one more time than we fall down.” In this entrepreneur’s case, she literally did fall down but resolved to stand back up and make a change that would impact many lives and ultimately lead her to greater success.

Walt Disney

Before creating the cinematic sensations that he’s known for today, Walt Disney was fired from a newspaper company for lacking creativity. Following this setback, he started his own animation business called Laugh-O-Gram, which he had to close after one of his distributor partners shut down.

Dejected and penniless, Disney made his way to Hollywood where he encountered more rejection and failure. Finally, he began to produce his own movies, but many of them cost him more money, because the development of animation films at the time proved to be very pricey. Even famous movies like Alice In Wonderland and Sleeping Beauty lost half a million dollars and caused massive layoffs.

However, Disney endured and went on to successfully co-found Walt Disney Company, establish iconic cartoon characters like Mickey Mouse, and start building the Disney Theme Parks. Over the course of his life, Disney received 50 nominations for the Academy Awards and was awarded 22 of them, but throughout his hard-earned success, he attributed his accomplishments to an adventurous spirit by stating:

“Courage is the main quality of leadership…no matter where it is exercised. Usually it implies some risk — especially in new undertakings. Courage to initiate something and to keep it going, pioneering and adventurous spirit to blaze new ways, often, in our land of opportunity.”

Robin Chase

Graduate of Wellesley College and MIT’s Sloan School of Management, Robin Chase was born to build businesses. So when transportation entrepreneurship called her name, she created Zipcar, a car sharing service. However, in the early phases of establishing her company, Chase realized that their daily rental rate was too low and that they’d need to raise prices by 25 percent.

Upon discovering this mistake, she admitted to shutting her office door and having a breakdown. Not only could she lose all credibility, the business itself could also crumble. But instead of giving up and going home, Chase pulled herself together and personally addressed the people who were upset about the change of prices and apologized. Fortunately, her employees and clients responded well, and she was able to dodge a bullet by just being honest.

If that near disaster wasn’t enough, this businesswoman also faced failure with both Zipcar and GoLoco, because as she described, “We built the website first and asked our customers about it later.” Thus, they had to make radical adjustments since they did not listen to their audiences’ needs first.

But Chase’s get it done personality pushed both companies through hard times and qualified her to receive awards like Innovator of the Year (SBANE, 2002), Woman Entrepreneur of the Year (2002), Harvard College Women’s Leadership Award (2014), and TIME Magazine’s 100 Most Influential People. Her focus and grit ultimately allowed her to conquer obstacles and see her vision become a reality.


If you’re experiencing letdown or feel like a failure, take courage. You’re not alone and you can overcome anything you set your mind to. Remember that setbacks are part of the road to success and that it takes belief, endurance, focus, and courage to reach your end goal.

We hope you found these stories inspiring and that they encourage you to push past failures. If you have any questions or would like more tips, let us know today!  

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