9 Successful Entrepreneurs Who Failed at Least Once

9 entrepreneurs who failed before they succeeded

1. Bill Gates: Traf-O-Data hit fatal road bumps

Have you ever driven over one of those 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 in 1972. His system recorded traffic information and fed it back to government authorities, civil engineers and others who needed it. While it sounded like a useful business idea, 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 needed to create Microsoft’s first line of software products a few years later. Today, Microsoft remains one of the most valuable companies in the world, consistently ranking among the top firms by market capitalization.

Key Takeaway: Failed ventures provide valuable experience and skills that can be applied to future successful endeavors.

2. Steve Jobs: Fired by the company he helped found

Do you remember the Apple I or Apple Lisa? If you don’t, you’re not alone. Those were two products Apple produced that crashed and burned. Unfortunately for Apple co-founder Steve Jobs, they were products he pushed for, and they cost the company millions of dollars in development — money it failed to recoup. A pattern of costly production decisions led to Jobs’s ouster from Apple in the mid-1980s.

But Jobs eventually found his way back to the company in 1997, thanks partly to another business he founded in the interim, NeXT. After Apple acquired NeXT, Jobs himself became a valuable commodity again. He took the helm of Apple and kicked off a period of expansive growth and innovation that continues to this day under the leadership of John Ternus.

Key Takeaway: Being forced out of your own company doesn’t end your story — it can create new opportunities for innovative comebacks.

3. Arianna Huffington: Multiple rejections before she found success

After Arianna Huffington finished writing her second book, she received rejection notices from nearly 40 publishers. When she ran for governor of California in 2003, she received less than 1 percent of the popular vote. However, she learned something from her failed political campaign: According to Huffington, running for office taught her about the power of the internet.

She channeled that hard-won insight into launching The Huffington Post in 2005. Today, HuffPost, as it’s now called, ranks among the most well-known and frequently visited sites on the internet. 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 company that aims to prevent burnout and improve today’s work culture.

Key Takeaway: Extract valuable lessons from every failure and apply that knowledge to create new opportunities in different industries.

4. Thomas Edison: Deemed too stupid to learn anything

Growing up in the mid-1850s, Thomas Edison was expelled from school for being “unteachable.” Thankfully, his mother believed in him and encouraged him to continue his education, even teaching him herself at one point. But things didn’t get much better for Edison when he entered the workforce. He was unceremoniously fired from several jobs because he wasn’t productive enough.

Edison ultimately secured his place in American history, though even his earliest attempts at perfecting the light bulb numbered in the thousands. Yet through every setback and every dismissal, he refused to quit. Over the course of his career, he became one of history’s most prolific inventors, amassing 1,093 United States patents — including patents for the phonograph and the motion picture camera.

Key Takeaway: Persistence in the face of repeated failures and criticism can lead to groundbreaking innovations that change the world.

5. Walt Disney: A 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 in the 1920s, 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.

Such setbacks so early in his career might’ve led a less determined person to quit. But Disney overcame these failures and turned his brand into a global empire. Perhaps most importantly, he never let his numerous struggles dull his imagination. Disney went on to pioneer several new animation and filmmaking techniques that revolutionized the industry.

Key Takeaway: Maintain your creative vision and imagination despite setbacks — they are often the foundation for revolutionary success.

6. Frederick W. Smith: A C-grade for FedEx

In 1965, Frederick W. Smith received a grade of C on an economics assignment in which he outlined the basic concept behind what would become FedEx. In his paper, Smith argued for a hub-and-spoke approach to distributing goods for faster delivery. Apparently, his professor at Yale didn’t share his vision and scored him poorly.

Smith, however, never let go of his idea. In 1971, upon returning from serving in the Vietnam War, he strategized how to make his idea for an express transport and delivery business a reality and officially launched Federal Express in April 1973. He raised millions to start what is now one of the world’s most well-known companies. Smith’s trajectory demonstrates the success that can follow when you find investors and disrupt an industry.

Key Takeaway: Believe in your innovative ideas even when experts dismiss them — academic grades don’t determine entrepreneurial potential.

7. Nick Woodman: Funbug flop to GoPro profits

Have you ever heard of Funbug? You probably haven’t, unless you were one of the investors who lost millions of dollars because of it. Funbug was a startup founded in 1999 by Nick Woodman, who sought to merge marketing with a gaming platform. The concept was a miss, however, and the company shuttered.

Afraid of repeating the mistakes he made with Funbug, in 2002, Woodman dedicated himself fully to making his next effort, GoPro, a successful company within four years. He learned to use a sewing machine borrowed from his mother to make the 35mm camera’s wrist strap and would stay up late to speak with Chinese manufacturers about creating other parts. His persistence paid off — GoPro went public in 2014 and became a sought-after action camera brand.

Key Takeaway: Use the fear of repeating past mistakes as motivation to dedicate yourself completely to your next venture’s success.

8. J.K. Rowling: Writing Harry Potter on welfare

While writing the first Harry Potter book, J.K. Rowling was a single mother receiving welfare benefits. To make matters worse, once the book was completed in 1995, no one wanted to publish it. After a dozen rejections, Rowling finally found a willing publisher in Bloomsbury, but the company urged her to change her pen name out of fear that young male readers wouldn’t want to read a book written by a woman.

Rowling’s pseudonym stuck, and so did Harry Potter. With six more novels published through 2007, she became responsible for creating one of the most beloved and successful series in the history of children’s literature. The books led to eight lucrative film adaptations, a spinoff movie franchise, a Broadway show and even theme parks. At one point, the formerly broke Rowling, who went on to found online ventures like Pottermore, was reported to be worth $1 billion.

Key Takeaway: Financial hardship and multiple rejections don’t define your potential — persistence and believing in your work can lead to extraordinary success.

9. 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 two examples:

• When Amazon launched in the mid-1990s, customers leveraged a glitch that allowed them to buy a negative number of books and receive a credit from the company.
• In the late 1990s, Bezos insisted on changing Amazon’s business model so the company could buy, store and eventually sell millions of dollars in toys. More than $100 million worth of toys were purchased and warehoused by Amazon in anticipation of the Christmas shopping season. But after the holiday, $50 million in toys were left unsold, and Amazon had to give most of the excess inventory away because of insufficient warehouse storage space.

Although Bezos made several errors in Amazon’s early years, he still managed to transform the company into a successful e-commerce platform. 

Key Takeaway: Early operational mistakes and costly errors don’t prevent long-term success when you remain committed to continuous learning and adaptation.

Common themes among famous people that failed at first

The famous entrepreneurs profiled above share several key characteristics that enabled them to transform setbacks into extraordinary success — and their stories offer meaningful lessons for anyone trying to build something from scratch.

1. They all demonstrated remarkable resilience and refused to let initial setbacks define their futures. Whether it was Edison’s many failed attempts at the light bulb or Rowling’s dozen rejections, these individuals maintained unwavering belief in their vision despite repeated disappointments.
2. They treated failure as education rather than defeat. Gates leveraged his Traf-O-Data experience to build Microsoft’s foundation, while Huffington applied lessons from her political campaign to create digital media success. This ability to extract valuable insights from setbacks and apply them to new ventures distinguishes successful entrepreneurs from those who give up.
3. These entrepreneurs showed adaptability and a willingness to pivot when necessary. Jobs founded NeXT after leaving Apple, Disney shifted focus after losing Oswald and Bezos continuously adjusted Amazon’s business model despite costly mistakes. Their stories prove that entrepreneurial success often requires the courage to fail, learn and try again with newfound wisdom.

How to deal with failure as an entrepreneur

Failure is a near-universal experience in business and life. While no one likes to fail, a setback doesn’t have to derail your future success. Below are some tips for dealing with failures along the entrepreneurial journey:

• Expect failure to be a part of your story: “Start to get comfortable with failure and understand that it is part of the process,” Charlotte Jones, founder of Business Scale Academy, told us. “It’s how you respond that shapes your journey and success.” Jones said that acknowledging your failures can “shift your perspective … and open up so many opportunities that you wouldn’t otherwise have spotted.”
• 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 temporary setbacks to help you learn from your mistakes. “Every failure carries a lesson; you just have to be open to it. Taking the time to debrief will help you pull out those learnings,” Jones said. When you understand where you went wrong, you can develop creative solutions to ensure you do things differently when confronted with the same problems in the future.
• Seek the advice of a mentor and connect with peers: Lindsay Hyde, a senior lecturer at Harvard Business School who teaches aspiring entrepreneurs how to avoid startup failure, said founders “have very few people they can consult with as they are failing.” That’s why finding a community with mentors and peers is critical. Mentors have the advantage of hindsight and can impart the wisdom they gleaned from their own mistakes, while fellow entrepreneurs can “serve as a sounding board,” Hyde said. The right support network can help you make meaningful connections to elevate your next venture and spur professional growth.
• Don’t stop believing in yourself: Rather than letting your failures drag you down, continue to tell yourself you have the skills and knowledge to succeed in the future. “Failure is hard for founders because their own identity and sense of self-worth are often intertwined with the business. Founders should work to see the business as separate from their own sense of self,” Hyde said.

What entrepreneurs can learn from failure

Learning from your failures is essential for setting yourself up for future success. Here are some of the lessons you should strive to take away from any rejections or missteps as you pursue your business goals:

• The role you played in the situation: Hyde said ego can drive founders to blame others or market factors for a company’s defeat. But “to maximize the learning value of experiencing a venture failure, entrepreneurs should take the time to reflect on their role in the failure of the business and get candid feedback from trusted advisors as to their role in it,” she said.
• Whether your business concept or product has merit: A business idea is little more than a hypothesis. Whether that idea succeeds or fails is largely a reflection of your business model and how well you proved your concept. “The more that founders can sequence a series of small tests to validate or invalidate the need for their business, the better off [they] will be,” Hyde said.
• How resilient you are: From her own entrepreneurial failures, Jones said she “learned resilience — how to bounce back quickly, stay resourceful and adapt fast.” She then used those principles going forward to form the foundation of her next business. You may not build the strength you need to succeed without the stumbles.

Skye Schooley and Julie Ellis contributed to this article. Source interviews were conducted for a previous version of this article.