Free Enterprise Staff  | July 16, 2014

To Win in Business, These 9 Successful Entrepreneurs Embrace Failure

If you look back on your career, what are you most proud of? If you’re like the majority of people, your most cherished professional memories probably center on significant accomplishments—the high-paying job you landed; the major promotion you scored; or the important deal you closed.

Take a moment, though, and think about all of the times you’ve failed. Certainly, we’ve all endured stinging defeats and missed opportunities. Yet we tend to gloss over these setbacks when we’re wading through the waters of bygone days. But should we? If you posed that question to any of the world’s most successful businesspeople, there’s a very good chance they’d have a simple answer for you.


Failing is a part of life that can make you feel like, well, a failure. But a growing chorus of businesspeople is hoping to upend its negative connotation. Across the U.S., entrepreneurs are not just acknowledging their own personal failures, but touting them. In Silicon Valley, for example, representatives from the technology and business communities meet for an annual event, FailCon, that gives attendees a platform to talk at length about the many, many times they’ve failed over the course of their careers.

Why has failure become the latest buzzword among the Technorati? It’s pretty simple, actually: You learn a whole lot more failing than you do succeeding, and there’s a good chance you’ll do it a lot more of it, too, during your professional development.

If you’re still on the fence about whether you should be prouder of your own failures, we’ve put together a list of thriving entrepreneurs whose embrace of their own major career setbacks helped catapult them to enviable success down the road.

1. Richard Branson: Branson might have become a billionaire on the strength of his Virgin empire, but that doesn’t mean he hasn’t weathered his fair share of failures. Along the path toward mega-wealth, Branson has made missteps that have lost him money and forced him to shutter companies. However, Branson credits his ability to learn from these blunders as a major driver of his own success.

2. Steve Jobs: Jobs, who was famously ousted from Apple, the company he co-founded, after a series of miscalculations, used his time away to run a string of other successful firms like Pixar Animation. Upon his triumphant return to Apple, Jobs launched the iconic iPhone and iPad devices, and steered the company toward unprecedented growth.

3. Michael Bloomberg: Before Bloomberg started his eponymous company and amassed a personal fortune estimated at more than $30 billion, he worked on Wall Street at Salomon Brothers—a job from which he was fired. Yet instead of wallowing in his misfortune, Bloomberg continued to push onward. “I never look over my shoulder,” the former New York City mayor recalls in “Bloomberg by Bloomberg,” his autobiography. “Once finished: Gone. Life continues!

4. Reid Hastings: Hastings rose to prominence as the founder of Netflix, which remains a darling of Wall Street thanks to its seemingly unstoppable growth. In 2011, however, Hastings came under fire when the company announced it would split Netflix into multiple businesses. Hastings learned from the slipup, as he set out on a campaign that restored the brand’s image and returned it to profitability.

5. Elon Musk: Among the world’s most ambitious businesspeople, Musk has not only made a career out of his many blunders, but also encourages his employees to do so, as well. Musk’s failures have cost him—in 2007, he admitted to having lost his fortune—but they’ve also helped him launch companies such as Tesla and SpaceX, which have fundamentally transformed their respective industries.

6. Mickey Drexler: If you like shopping at J.Crew, you can thank Drexler for remaking the company into the stylish brand it is today. Before taking over at J.Crew, though, Drexler was summarily fired by the Gap, another retailer that he led to fashion glory prior to its much-publicized downfall. Not one for complacency, Drexler has publicly discussed how his experience at the Gap has informed his success outside of it.

7. Sean Parker: Parker’s resume may contain more failures than successes, but the tech entrepreneur’s successes have most certainly been bigger. Parker has presided over a number of failed ventures—one of his latest, Airtime, folded this year—but he’s learned from each along the way as he’s played an instrumental role in the growth of companies such as Napster and Facebook.

8. Jack Dorsey: Like Jobs, Dorsey, who co-founded Twitter, was let go from the social network after a period of upheaval. Afterwards, Dorsey leveraged his time at Twitter to start the mobile payments company Square, where he honed his leadership and strategy skills. After his hiatus, Dorsey engineered a comeback at Twitter, where he reassumed his leadership position in 2011.

9. J.K. Rowling: When she sat down to write her first novel, the celebrated author could barely pay her heating bill. However, Rowling drew on her struggles to create the world of Harry Potter, one of the most popular series of books in history that has spawned an equally successful movie franchise, a theme park, and countless merchandise goods.