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Successful Entrepreneurs Who Failed at First — Lessons in Persistence

Gates, Huffington, Jobs, Rowling and even Edison were deemed failures at one point. Here’s how they bounced back from rejections and missteps.

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Written by: Sean Peek, Senior AnalystUpdated Aug 22, 2025
Shari Weiss,Senior Editor
Business.com earns commissions from some listed providers. Editorial Guidelines.
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If you’re stumbling along the entrepreneurial journey or feel your business dreams are beyond your reach, take this to heart: Many of the most successful entrepreneurs experienced some colossal failures before finding success. This isn’t a coincidence — failure is an entrepreneur’s most demanding teacher, forcing critical pivots that reveal market realities and building the resilience necessary to weather future storms. When entrepreneurs fail forward, they develop what researchers call “entrepreneurial learning,” the ability to rapidly test assumptions, adapt strategies and recognize opportunities that others miss. Perhaps most importantly, failure strips away the fear, freeing entrepreneurs to take the calculated risks that true innovation demands.

To inspire the next generation of business owners, business.com is looking at some determined entrepreneurs who may be well-known today but were far from overnight successes. The entrepreneurs featured below didn’t succeed despite their failures. They succeeded because of them, with each setback providing invaluable insights that informed their eventual breakthroughs. We’re also sharing expert-backed tips for transforming failure into a competitive advantage as you pursue your business goals.

9 entrepreneurs who failed before they succeeded

Name

Initial Failure

Ultimate Success

Key Lesson

Bill Gates

Traf-O-Data failed as a business venture

Founded Microsoft, became global tech leader

Learn from failure to build future success

Steve Jobs

Ousted from Apple after product failures

Returned to lead Apple to unprecedented innovation

Persistence and innovation create new opportunities

Arianna Huffington

Rejected by nearly 40 publishers, political campaign loss

Founded Huffington Post, then Thrive Global

Adapt knowledge from setbacks to new ventures

Thomas Edison

Expelled from school, fired from jobs, failed inventions

Invented light bulb, held 1,093 U.S. patents

Persistence and experimentation lead to breakthroughs

Walt Disney

Lost Oswald character, ideas rejected, lived in poverty

Created iconic brand, revolutionized animation

Imagination and resilience drive long-term success

Frederick W. Smith

Delivery concept graded C at Yale

Founded FedEx, became global logistics leader

Believe in your ideas despite criticism

Nick Woodman

Funbug startup failed, lost investors’ money

Founded GoPro, became industry pioneer

Dedication and learning from mistakes build future wins

J.K. Rowling

Rejected by publishers, struggled on welfare

Created Harry Potter, became global literary icon

Perseverance transforms setbacks into success

Jeff Bezos

Costly errors launching Amazon, stuck with unsold inventory

Built Amazon into leading e-commerce site

Experimentation and resilience fuel business growth

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

Bill Gates
Bill Gates’s eventual entrepreneurial success led to the founding of the Gates Foundation, which fights inequities around the world. (Source: Alexandros Michailidis / Shutterstock)

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. Fifty years on, Microsoft is one of the biggest technology companies in the world — and Gates is among the world’s richest.

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

>> Read Related Article: Common Mistakes That Can Lead to Product Failure

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

Steve Jobs on a smartphone
Steve Jobs died of cancer in 2011, but his legacy lives on through products like the iPhone, which launched in 2007. (Source: DenPhotos / Shutterstock)

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 Tim Cook.

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

FYIDid you know
Technology is essential to running a modern business. If you're just getting your business off the ground, one of the first tools you'll need is high-quality accounting software to keep track of expenses and revenue.

3. Arianna Huffington: Multiple rejections before she found success

Arianna Huffington
Arianna Huffington’s failed political career led her to found The Huffington Post, which was later acquired by AOL for $315 million. (Source: drserg / Shutterstock)

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 used this new knowledge to launch The Huffington Post in 2005. Today, HuffPost, as it’s now called, is 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.

TipBottom line
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4. Thomas Edison: Deemed too stupid to learn anything

Thomas Edison
Thomas Edison spent years tinkering in his New Jersey laboratory before the light bulb literally and figuratively went off. (Source: Dennis MacDonald / Shutterstock)

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.

While Edison eventually earned his place in American history, even his first thousand or so attempts at getting the light bulb to work were failures. Yet, despite all of his defeats, Edison never gave up. He was a prolific inventor who amassed 1,093 United States patents during his lifetime, including for the movie 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

graphic of Walt Disney
Walt Disney himself is as beloved as some of the characters he created, prompting artistic tributes to him all over the world. (Source: Javi Az / Shutterstock)

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.

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. Walt Disney Studios Motion Pictures released a live-action Snow White adaptation in 2025.

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

FedEx Corporate HQ
More than 50 years after its founding, Frederick W. Smith remained a vital part of FedEx as its executive chairman until his death in 2025. (Source: Poetra.RH / Shutterstock)

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. 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

Nick Woodman
Nick Woodman, far right, brought his invention, the GoPro camera, to the Webby Awards, where his team won an award for their social media presence. (Source: Debby Wong / Shutterstock)

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. A decade later, Ernst & Young named Woodman the National EY Entrepreneur of the Year for retail and consumer products.

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

J.K. Rowling
By the time Harry Potter and the Deathly Hallows was released in 2007, Rowling’s book series was a global sensation. (Source: s_bukley / Shutterstock)

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.

FYIDid you know
According to Global Entrepreneur Monitor's 2024/2025 Global Report, 49 percent of survey respondents said they won't start a business out of fear of failing, an increase from 44 percent in 2019. Rather than stay on the sidelines, you can look to top business podcasts for inspiration, guidance and a better chance of succeeding.

9. Jeff Bezos: Costly mistakes launching Amazon

Jeff Bezos
Jeff Bezos’s early failures at Amazon didn’t stop him from growing the company well beyond book-selling. (Source: lev radin / Shutterstock)

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 turn the company into the premier website for online shopping — and made himself one of the wealthiest people in the world in the process.

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 failure into extraordinary success. 

  1. They all demonstrated remarkable resilience and refused to let initial setbacks define their futures. Whether it was Edison’s thousand 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 inevitable in business and life. While no one likes to fail, doing so doesn’t have to jeopardize your future successes. 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,” said Hyde.
TipBottom line
As Gates and Woodman learned, sometimes it's better to close up shop than continue pushing a failing enterprise. "Entrepreneurs should develop a stopping rule that they use to know when it is time to wind down the business," recommended Hyde. "This will help founders to make responsible decisions that allow them to shut down their venture with their reputation and relationships intact."

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.

FAQs

Many famous entrepreneurs experienced significant failures before achieving success. J.K. Rowling is a prime example: She was a single mother on welfare when she wrote the first Harry Potter book, which a dozen publishers then rejected before attracting Bloomsbury. Her series went on to become one of the most beloved and profitable in literary history, making her a billionaire. As another example, Steve Jobs was ousted from Apple, the company he co-founded, due to costly product failures, but returned years later to lead the company to unprecedented innovation with products like the iPhone and iPad.
Bill Gates' first business failure was Traf-O-Data, a company he founded in 1972 with friends. The venture aimed to analyze traffic data using a device that recorded information from those black cables stretched across roads that count tire bumps. While the concept seemed promising for government authorities and civil engineers who needed traffic information, the business ultimately failed to gain traction. However, this failure proved invaluable — the experience and technical skills Gates gained from Traf-O-Data directly contributed to Microsoft's early software development capabilities.
Walt Disney was a creative person who turned his success into failure; he exemplifies how creative vision can overcome devastating setbacks. Early in his career, Disney experienced crushing failures: He lived in such poverty that he survived on dog food, lost creative control of his first successful character (Oswald the Rabbit) in a contract dispute with Universal Pictures, and saw MGM reject Mickey Mouse because executives believed women were afraid of mice. His early animation company also failed financially. However, Disney's unwavering imagination and creative persistence eventually transformed these failures into the foundation of a global entertainment empire that revolutionized animation and filmmaking.

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

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Written by: Sean Peek, Senior Analyst
Sean Peek co-founded and self-funded a small business that's grown to include more than a dozen dedicated team members. Over the years, he's become adept at navigating the intricacies of bootstrapping a new business, overseeing day-to-day operations, utilizing process automation to increase efficiencies and cut costs, and leading a small workforce. This journey has afforded him a profound understanding of the B2B landscape and the critical challenges business owners face as they start and grow their enterprises today. At business.com, Peek covers technology solutions like document management, POS systems and email marketing services, along with topics like management theories and company culture. In addition to running his own business, Peek shares his firsthand experiences and vast knowledge to support fellow entrepreneurs, offering guidance on everything from business software to marketing strategies to HR management. In fact, his expertise has been featured in Entrepreneur, Inc. and Forbes and with the U.S. Chamber of Commerce.