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Never Giving Up: 9 Successful Entrepreneurs Who Failed at Least Once 

Sean Peek
Sean Peek
business.com Contributing Writer
Updated Sep 20, 2022

Gates, Huffington, Jobs, Woodman, Bezos and even Edison were deemed failures at one point. Here's how they bounced back from rejection.

If you’ve ever been frustrated or felt that your dreams are just beyond your reach, take this to heart. Many of the most successful entrepreneurs experienced some colossal failures before finding success. Yet, despite those setbacks, they could look beyond their mistakes and continue pushing forward. Below are some prime examples of entrepreneurs who didn’t get it right the first time, but persevered to greatness.

Entrepreneurs who succeeded after failure

Bill Gates: Traf-O-Data

Have you ever driven over one of those weird black cables that stretch across the road and measure traffic by counting tire bumps? Bill Gates and a few of his friends did, which is why he founded Traf-O-Data. 

This system recorded traffic information and fed it back to government authorities, civil engineers and others who needed it. The concept ultimately failed.

Despite Traf-O-Data’s failure as a business venture, the project gave Gates and Paul Allen the experience and skills they ultimately needed to create Microsoft’s first line of software products a few years later. [Learn more about the mistakes that can lead to product failure.]

Steve Jobs: Fired by the company he helped found

Do you remember the Apple I or Apple Lisa? If not, you’re not alone. These were two products Apple produced that crashed and burned. Unfortunately for Steve Jobs, these were products that he pushed for and cost Apple millions of dollars in development, money it failed to recoup. This pattern of costly production decisions led to Jobs being ousted from Apple in the mid-eighties.

Fortunately, Jobs eventually found his way back to the company in 1997 to take the helm during a period of expansive growth and innovation that continues to this day.

Bottom LineBottom Line: While being forced to step down from his own company may have been a massive setback for Jobs, it ultimately led him to rejoin Apple and lead it to its most profitable and prolific period.

Arianna Huffington: Multiple rejections before she found success

After Arianna Huffington finished her second book, she received rejection notices from nearly 40 publishers. When she ran for governor of California, she received less than 1 percent of the popular vote. However, she did learn something from her failed political campaign.

According to Huffington, running for office taught her about the power of the internet. She used this new knowledge to launch her website, The Huffington Post. Huffington’s news site is among the most well-known and frequently visited on the internet. In addition, she has a positive view of failure, calling it a necessary part of success.

Despite the many setbacks she faced throughout her career, Huffington advocates learning from your failures to help you move on to the right profession or project for you. 

Did you know?Did you know? In 2016, Huffington stepped down from her role as president and editor-in-chief of The Huffington Post Media Group to launch Thrive Global, a health and wellness media platform that aims to combat burnout and improve today’s work culture.

Thomas Edison: Deemed too stupid to learn anything

Thomas Edison was expelled from school for being “unteachable.” Fortunately, his mother believed in him and encouraged him to continue his education, even teaching him herself at one point. Unfortunately, things didn’t get any better for Edison when he entered the workforce. He was unceremoniously fired from several of his first jobs because he was not productive enough.

Even his first thousand or more attempts at getting the light bulb to work were failures. Yet, despite all of his defeats, Edison was a prolific inventor who had amassed 1,093 patents during his lifetime, including the light bulb and the movie projector.

Bottom LineBottom Line: If you don’t seem to fit into a specific professional position or corporate culture, that doesn’t mean you’re a failure. It might signify that a particular role or company is not the right fit, so it may be more beneficial for you to move on rather than try to assimilate.

Walt Disney: Failed production company and labeled as lacking creativity

If you focus on Walt Disney’s failures, it’s amazing that The Walt Disney Company ever reached the level of success it enjoys today. Disney was, at one point, living on dog food and unable to pay his rent. Then, during a contract dispute with Universal Pictures, he lost creative control of his first character, Oswald the Rabbit. Next, MGM rejected his Mickey Mouse character because the studio believed women were afraid of mice.

Before the screening of Pinocchio, Disney hired several little people to stand on top of the marquee, dressed as puppets, to wave at the families coming into the theater. He provided them with wine and food for the day. By the time the screening began, the little people were drunk, naked and swearing at the crowd. Disney overcame these failures and turned Disney into a global empire.

Despite the numerous struggles and setbacks he experienced in his early career, Disney never let his failures dull his imagination. He went on to pioneer several new animation and filmmaking techniques that revolutionized the industry.

Did you know?Did you know? Walt Disney was recognized at the 1939 Academy Awards for his significant innovations in film animation for Snow White and the Seven Dwarfs. The Academy gifted him with an honorary award of one statuette and seven miniature statuettes.

Fred Smith: A failing grade for FedEx

Actually, it wasn’t a failing grade. Instead, according to legend, Fred Smith received a grade of C on the writing assignment in which he outlined the basic concept behind FedEx. Smith had noticed that automation was becoming the norm and realized that this would impact the logistics behind package delivery systems, along with many other things.

Although his instructors did not share his vision, Smith never let go of his idea. Upon returning from serving in the Vietnam War, Smith strategized how to make his idea for an express transport and delivery business reality and raised $80 million to start one of the world’s most well-known companies.

FYIFYI: Early adopters of disruptive ideas and technologies often face the most difficulties when launching a new business, especially with securing buy-in from investors. However, if you know that your idea will address a future pain point, the right collaborators can help your venture find its footing.

Nick Woodman: Funbug flop to GoPro

Have you ever heard of Funbug? Unless you were one of the investors who lost a few million dollars because of it, you probably haven’t. But, if you were one of them, the thought of Funbug probably brings back painful memories.

Funbug was a marketing company designed to merge marketing with gaming, but the concept was a miss. Nick Woodman learned from his mistakes and ultimately launched the company that produces the GoPro.

Afraid of repeating the mistakes he made with Funbug, Woodman dedicated himself fully to making GoPro a successful company within four years. He learned to use a sewing machine borrowed from his mother and would stay up late to speak with Chinese manufacturers about creating the parts needed for GoPro’s 35mm camera. [Learn how to work smarter, not harder.]

J.K. Rowling: Writing Harry Potter on the dole

While writing the first Harry Potter book, J.K. Rowling was a single mother receiving welfare benefits. However, she overcame her situation by not only completing the book, but also finding someone to publish it. The person who selected her book for publication did so because her daughter fell in love with the story.

Rowling never forgot her humble origins. When asked why she didn’t establish citizenship in a place where she could find shelter from paying taxes, she responded that she was happy to pay taxes into a system that supported her when she needed it most.

Rather than remain discouraged by the dozen rejections she initially received from publishers, Rowling persevered and went on to publish one of the most beloved and successful series in the history of children’s literature.

Jeff Bezos: Costly mistakes launching Amazon

Amazon founder Jeff Bezos made some mind-blowing mistakes while getting the company off the ground and even more after its successful launch. Here are just a few of them:

  • When the company began selling toys and books, Bezos insisted on changing the business model so the company could purchase and store millions of dollars in toys. More than 100 million toys were purchased and warehoused in anticipation of the Christmas season. After the holiday, 50 million toys were left. Amazon gave most of the toys away because of insufficient warehouse storage space.
  • When Amazon first launched, people could leverage a glitch that allowed them to buy a negative number of books and receive a credit from the company.

Although Bezos made several errors when preparing for and launching Amazon, he still managed to turn the company into the premier website for online shopping.

How to deal with failure

Failure is inevitable in business and life. While no one likes to fail, doing so doesn’t have to jeopardize your future successes. Here are some tips for dealing with your failures when they arise:

  • Reframe your failures as short-term setbacks and learn from them. Rather than viewing your failures as a sign to give up, reframe them as short-term setbacks to help you learn from your mistakes. When you understand where you went wrong, you can develop creative solutions to ensure you do things differently when confronted with the same problem in the future.
  • Think strategically to step out of your comfort zone. Once you’ve dusted yourself off from stumbling, think strategically and take calculated risks to plan your next move. Weigh your options carefully and make decisions with a clear, calm mind. Lean on your support system and ask for their unbiased opinion. To grow and gain new experiences, both personally and professionally, you’ll need to move past your fear of failure and take some calculated risks. 
  • Seek out the advice of a mentor. Everyone needs encouragement when they’ve encountered unexpected problems and challenges. Mentors have the advantage of hindsight and can impart the wisdom they gleaned from their mistakes. In addition to sharing their advice, the right mentor can also help you make important connections to elevate your business and spur professional growth. 
  • Maintain a positive mindset to persevere past your failures. Rather than letting your failures drag you down, focus on learning from your mistakes, and believe you have the skills and knowledge to succeed in the future. In addition to the entrepreneurs featured here, there are plenty more who failed on their way to success. If they can find success after their failures, you can as well.

Julie Ellis contributed to the writing and research in this article.

Image Credit: fizkes / Getty Images
Sean Peek
Sean Peek
business.com Contributing Writer
Sean Peek has written more than 100 B2B-focused articles on various subjects including business technology, marketing and business finance. In addition to researching trends, reviewing products and writing articles that help small business owners, Sean runs a content marketing agency that creates high-quality editorial content for both B2B and B2C businesses.