21 Entrepreneurs Who Failed Big Before Becoming a Success

entrepreneurs who failed

Failure is a part of business. Very few entrepreneurs ever make it big without first experiencing some massive failures. Whether it be running a business into the ground, getting fired from a job or even going to jail, plenty of very successful entrepreneurs have seen huge failures before ever accomplishing their dreams.

So if you ever feel worn down or intimidated by the thought of failing, just take a look at these entrepreneurs who failed before making it big.

Entrepreneurs Who Failed First

Evan Williams

Before co-founding Twitter, Williams (pictured above) developed a podcasting platform called Odeo. But the platform didn’t take off, in part because Apple announced the podcast section of the iTunes store shortly after the company launched. It folded shortly afterward.

Reid Hoffman

Before co-founding LinkedIn and investing in big names like PayPal and Airbnb, Hoffman created SocialNet, an online dating and social networking site that ultimately failed.

Sir James Dyson

Dyson wasn’t always a well-known name associated with vacuum cleaners. In fact, it took Sir James Dyson 15 years and all of his savings to develop a bagless prototype that worked. He developed 5,126 prototypes that failed first.

Momofuku Ando

Before even coming up with the idea for instant noodles, which took him many tries to develop successfully, Ando had a small merchandising firm in Japan. But in 1948, he was convicted of tax evasion and spent two years in jail. He then lost that company due to a chain reaction bankruptcy.

Akio Morita

Back in the early days of Sony, Morita’s products weren’t quite as popular or well known as they are today. In fact, the first product was a rice cooker that ended up burning rice.

entrepreneurs who failed

Vera Wang

The famous fashion designer (pictured above) wasn’t always known for her high-end wedding gowns. In fact, Wang was once a figure skater. But she failed to make the U.S. Olympic figure skating team. She then moved on to work for Vogue, but was turned down for the editor-in-chief position before leaving to become a designer.

Bernie Marcus and Arthur Blank

Before founding The Home Depot, Marcus and Blank were officers at Handy Dan, a California based home center chain. They were both fired in 1978 for allegedly allowing the creation of a fund that was misused.

Milton Hershey

Hershey’s is one of the most recognized names in chocolate. But before founding the company, Milton Hershey was fired from his apprenticeship with a printer. And then he tried to start three different candy companies, all of which failed, before starting the Lancaster Caramel Company and the Hershey Company that made his sweet confection a household name.

Kathryn Minshew

Because of a dispute between co-founders, Minshew lost website access and all the savings she had invested in her site, PYP Media. But she took that failure and turned it into a new project, The Muse, along with many other members of her former team.

George Steinbrenner

George Steinbrenner owned a small basketball team called the Cleveland Pipers back in the early 1960s, long before he took over the New York Yankees organization. But there’s a reason you’ve never heard of that team. As a result of Steinbrenner’s direction, the entire Pipers franchise went bankrupt just a few years after he took ownership.

entrepreneurs who failed

Arianna Huffington

Before launching The Huffington Post, Arianna Huffington (pictured above) had a bit more trouble getting people to read her work. Her second book was rejected by 36 publishers. (Yes, you read that correctly — 36.)

Jeff Bezos

Amazon is one of the biggest success stories of the online era. But before Amazon became a household name, the company’s CEO had several failed ideas. One of the most notable was an online auction site, which evolved into zShops, a brand that ultimately failed. Still, CEO Jeff Bezos would repurpose the idea into what would eventually become the Amazon Marketplace.

Henry Blodget

Henry Blodget was working on Wall Street when then-Attorney General Eliot Spitzer brought a civil securities-fraud complaint against him over conflicts of interest between research and banking. But in the years that followed, he contributed to many major news outlets, eventually launching Business Insider, a trusted name in the business world.

Benny Luo

Though Luo has several successful ventures to his name, including NextShark and NewMediaRockstars, he also has several that didn’t work out. He tried his hand at network marketing, affiliate marketing and even online poker. However those ventures all fizzled eventually. But the experience obviously primed him for future success.

Lawrence Ellison

Ellison’s company, Oracle, has had its share of ups and downs. After Ellison dropped out of college and worked as a programmer for eight years, he co-founded the company with his former boss. But Oracle struggled for years before making it big. Ellison even had to mortgage his house to obtain a line of credit to keep the business afloat during that time.

entrepreneurs who failed

Tim Ferris

The author of “The 4-Hour Workweek” (pictured above) was turned down by about 25 publishers before finding one who actually agreed to publish his work — which later became a best selling title.

Peter Thiel

Before starting PayPal and investing in big names like Facebook, Thiel lost big. His early hedge fund, Clarium Capital, lost 90 percent of its $7 billion assets on the stock market, currencies and oil prices. Still greater success lay ahead.

Christina Wallace

The current vice president of branding and marketing at Startup Institute is the former co-founder of Quincy Apparel. When the company shut down in 2013, Wallace stayed in bed for three weeks before forcing herself to get up and re-join the world.

Henry Kaiser

The founder of Kaiser Shipyards is often referred to as the father of modern American shipbuilding. But during World War II, Kaiser’s Liberty ships started using welded hulls, which caused some of the hulls to crack, sometimes completely in two. It was hardly an impressive start to an entrepreneurial career.

Morten Lund

Lund now invests in up-and-coming companies like pitchXO and CapitalAid Ltd., and has made some successful investments in the past in companies like Skype and eBay. But in 2009, the Danish entrepreneur actually filed for bankruptcy because of some less-than-stellar investment decisions.

Fred Smith

Though we all know now that FedEx is a viable business model, Smith’s college professor disagreed. The future venture capitalist received a poor grade on an assignment where he pitched the idea for the company.

Evan Williams, Vera Wang, Arianna Huffington Images via Shutterstock, Tim Ferriss Image via Facebook


Annie Pilon Annie Pilon is a Senior Staff Writer for Small Business Trends, covering entrepreneur profiles, interviews, feature stories, community news and in-depth, expert-based guides. When she’s not writing she can be found exploring all that her home state of Michigan has to offer.

15 Reactions
  1. Clearly, it doesn’t mean that the path to success is a smooth one. One has to fail and stumble to reach it.

    • Very true – almost no one finds success without stumbling a few times first.

    • Ecclesiastes 3:1-8 certainly holds ground where it says “There is time for everything under heaven…” A time to fall, a time to get back up again, now that I found a venture capitalist whom I worked with in time past. This biblical verse stood the test of time and an inspirational one.

  2. I can barely wait to showcase my talent and perhaps innovation to be created after scores of disappointing failures. It’s just a matter of time that I’ll rise again maybe even as a politician and I can only wonder who would be standing next to me.

  3. You are misrepresenting Peter Thiel’s journey here. Firstly, he co-founded paypal and invested in Facebook BEFORE Clarium had its losses. Secondly, his losses were not 90%. 90% is the commonly quoted number referring to the fall in AUM of Clarium from peak to through, much of which was due to investor redemptions.

    A little googling and due diligence would’ve uncovered that.

    • Alex can you please give me some more information related to Peter theil coz I am working in a documentary in which I work on his failure to success journey so kindly if you have some other informative details about him you can mail me

  4. Thank you so much for this post. I’ve been beating myself up for the past two years because I thought I had this great idea and success would follow, but it has not happened yet! I’ve thought of giving up many times. However, I absolutely know without a doubt I was meant to do what I’m doing. I really needed to read this today as a reminder to follow my dream and not give up! The ends will definitely justify the means.

  5. About Peter Thiel is not correct.

  6. This gives me so much hope! I now understand about the crawling before you walk, and the stress and strain of being a business owner. I now understand that being in business means that everything is not always going to be fun and glory. Sometimes, failure is good, you learn from your mistakes

No, Thank You