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11 Money Lessons Learned From Other People’s Failures


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The road to success is paved with hard knocks and setbacks. Failure doesn’t define you – but the way you respond to it does.

Here is advice from 11 of the greatest success stories that were almost never told. What these creators and visionaries say about adversity is proof tough times don’t need to define your life.

1. Arianna Huffington

Arianna Huffington makes speech at Microsoft Convergence conference

Huffington grew up in Athens, Greece, with the dream of studying at Cambridge University one day. She accomplished that goal. But she realized who she wanted to be as an adult was very different from her major of economics: She wanted to be a writer. She published her first book, The Female Woman, at the age of 23.

Huffington long believed that excessive work leads to success. Then in 2007, she fainted from sleep deprivation and exhaustion. After collapsing in her office, she hit her head on her desk and suffered an injury to her cheekbone. She has since always made sleep a priority and has changed her approach to success. Here are a few lessons Huffington has passed on to others over the years…

“I wish I could go back and tell myself that there is no trade-off between living a well-rounded life and high performance is actually improved when our lives include time for renewal, wisdom, wonder, and giving. That would have saved me a lot of unnecessary stress, burnout, and exhaustion.”

“To live the lives we truly want and deserve, and not just the lives we settle for, we need a third measure of success that goes beyond money and power, and consists of four pillars: well-being, wisdom, wonder, and giving.”

2. Elon Musk

Elon Musk at the 2017 Vanity Fair Oscar Party at the Wallis Annenberg Center

On his way to becoming a billionaire, Elon Musk faced some major failures in his career and personal life.

In 1996, he was ousted as CEO of Zip2, an online directory for newspapers and one of the first companies he cofounded. Zip2 went belly up in 1999, the same year he cofounded his next business venture: an online financial services and payments company called X.com, which would later change to PayPal.

He was also ousted from PayPal – but this time, during his honeymoon. Following his failures at two Internet-based companies, Musk took his focus away from cyberspace and applied it toward the real thing.

In 2002, he founded his third company, SpaceX, with the goal of making ships to transport regular people into space. He also founded the electric car company Tesla in 2003.

Between 2006 and 2008, the company managed to launch two rockets into space, which both exploded. His third rocket launched and failed in 2008. By the end of the year, SpaceX and Tesla were both nearly bankrupt.

Musk is worth over $19 billion today. With every roadblock he’s hit along the way, it makes you wonder, how does he continue to push forward? Here are a couple of lessons Musk likes to pass on to other dreamers…

“Failure is an option here. If things are not failing, you are not innovating enough.”

And after he was removed as CEO of the company he co-founded?

“Going from PayPal, I thought: ‘Well, what are some of the other problems that are likely to most affect the future of humanity?’ Not from the perspective, ‘What’s the best way to make money?’”

3. Mark Zuckerberg

Mark Zuckerberg profile displayed on Facebook mobile

He launched Facebook in 2004, from his college dorm room his sophomore year at Harvard University. Today he’s worth over $77 billion. But even as a multi-billionaire, he is known to live a frugal lifestyle.

The college dropout is often seen wearing his trademark T-shirt, hoodie, and jeans. And even though he can afford to ride in a Donald Trump-type limousine, he drives a modest Volkswagen. The social network founder doesn’t believe money is the reason for the work he does, as he says…

“We don’t build services to make money; we make money to build better services.”

And he’s never been afraid of trying something different to stand out from the ordinary…

“In a world that’s changing really quickly, the only strategy that is guaranteed to fail is not taking risks.”

At least when you fail, you can still take a lesson away from the experience…

“You are better off trying something and having it not work and learning from that, than not doing anything at all.”

4. Bill Gates

Bill Gates attends the Clinton Global Initiative Annual Meeting

At only 17 years old, Bill Gates started his first tech company: Traf-O-Data, in 1972. It failed.

The early tech company used computer chips to analyze traffic data as cars drove over traffic counters – or as Wired simply calls the, “black hoses we drive over on roads.” It would then use that information to create reports for traffic engineers.

The company went out of business. Gates could’ve let the loss get the better of him, but instead he took the negative and turned it into a positive. He used the lessons learned from his mistakes with the first company and applied them to Microsoft…

“It’s fine to celebrate success, but it is more important to heed the lessons of failure.”

In fact, Gates sees more value in failure than he does success…

“Success is a lousy teacher. It seduces smart people into thinking they can’t lose.”

He also doesn’t believe only rich people can make themselves a success in this world…

“If you are born poor it’s not your mistake, but if you die poor it’s your mistake.”

5. Jeff Bezos

Jeff Bezos on a ipad monitor screen through a magnifying glass

Amazon’s CEO Jeff Bezos doesn’t believe a company can thrive by hitting a home run every time. He embraces failure as a part of his success.

“I’ve made billions of dollars of failures at Amazon.com.”

You don’t have to dwell on them. If he named them all, it would feel like “a root canal with no anesthesia.”

He originally founded the e-commerce giant as a discount Internet book seller in 1995, and during the Dot-com bubble, Amazon almost bit the dust. But Bezos bounced back.

He once wrote in one of his annual shareholder letters…

“Failure comes part and parcel with invention. It’s not optional. We understand that and believe in failing early and iterating until we get it right.”

Some of his other failures include:

  • The Fire Phone: Its first ever – and last – smartphone. Released in 2014, it couldn’t hold a candle to iPhone or other Androids, and ultimately flopped.
  • Amazon Destinations: This site was designed to help Amazon users find hotel deals. The online retailer tried out the travel industry in April 2015, and pulled the plug only six months later.
  • Amazon Local: This was an idea comparable to Groupon or LivingSocial. It was in operation from 2011 to December 2015.

Bezos doesn’t see these experiments as wasted efforts, though. Here’s what he said in another annual shareholders letter…

“I believe we are the best place in the world to fail (we have plenty of practice!)”

Find out: 5 Biggest Debt Traps for New Entrepreneurs.

6. Steve Jobs

Steve Jobs Co-founder, Chairman, and Chief Executive Officer (CEO) of Apple Inc

Saying he left us with the iPhone understates things. Steve Jobs was the creative force behind so many tech treasures that shape the world today. And believe it or not, he made some major mistakes in his lifetime.

The company he founded fired him. Then, when it was struggling, he triumphantly returned to save it from going under. Here are a few lessons the founder of Apple has left us with…

“Bottom line is, I didn’t return to Apple to make a fortune. I’ve been very lucky in my life and already have one. When I was 25, my net worth was $100 million or so. I decided then that I wasn’t going to let it ruin my life. There’s no way you could ever spend it all, and I don’t view wealth as something that validates my intelligence.”

Money wasn’t everything to Jobs – time was, and the fear of death was his motivator to accomplish more while he still had the chance…

“My favorite things in life don’t cost any money. It’s really clear that the most precious resource we all have is time.”

7. Mark Cuban

Mark Cuban attends 'The Clapper' Premiere during the 2017 Tribeca Film Festival at SVA Theatre

Before he owned the Dallas Mavericks, he sold garbage bags door-to-door.

He was only 12 years old at the time, but it was his first taste of business, and far from his last.

His entrepreneurial spirit didn’t mesh well with typical desk jobs. He was fired from his first few jobs after college. He taught himself to code, and founded a tech start-up called MicroSolutions. He sold it to Compuserv for $6 million, and has been launching and investing in companies ever since.

And as for the times when he was down and out? This is what he has to say…

“It doesn’t matter how many times you have failed, you only have to be right once.”

For advice to other business owners trying to get their start he says…

“It’s not about money or connections – it’s the willingness to outwork and outlearn everyone. And if it fails, you learn from what happened and do a better job next time.”

8. Carolyn Everson

Facebook App on iPhone with computer laptop background

She lost a ton of money in the “Dot-com bubble disaster” Pets.com in 1998. She was still a student at Harvard Business School at the time when she was fired.

She spent weeks in bed, ailing from her losses. And when she pulled herself together, she never looked back. Speaking to young women at a convention, she once said…

“Don’t worry about plotting out your entire life because you don’t know what’s going to be around in a few years. Be opportunistic instead, and follow your passion.”

She found herself in one of the top advertising jobs at Facebook, where she says the company’s motto is, “fail harder.”

The biggest life lesson she takes away from one of the darker times of her life is this…

“It’s OK to get fired; it’s OK to fail. There are going to be bumps in the road, but believe in yourself, and have self-confidence.”

Find out: 10 Need-to-Know Tips for Becoming an Entrepreneur

9. James Dyson

expensive dyson vacuum cleaner

Inventing a vacuum cleaner doesn’t sound glamorous, but it made him a millionaire. And his millions didn’t come easy. He regularly encounters failure, and like many great creators, he rolls with the punches when he has to.

“The key to success is failure. Success is made of 99 percent failure.”

As an inventor, his first claim to fame was a bagless vacuum cleaner. He patented his dual cyclone vacuum cleaner in 1980, but to his dismay, his product was rejected by most major manufacturers – so he started his own.

Despite the initial rejection, the public loved his product, and he even outsold the competitors who had rejected his idea. By 2005, his vacuum company was leading the U.S. market.

But this was just one product that succeeded. In 2000, he failed attempting to branch out to the appliance market as well. He created a washing machine called the ContraRotator. It ended up too difficult to use for the general public. His failure wasn’t worth throwing in the towel, though. As Dyson has said…

“Success is not always as enjoyable as you might think. When something’s a success, the results are clear. Failure is an enigma. You worry about it, and it teaches you something.”

10. J.K. Rowling

J.K. Rowling attends The EE British Academy Film Awards (BAFTA) at the Royal Albert Hall

She penned the hit fantasy book series Harry Potter, and introduced the world to the Hogwarts School of Witchcraft and Wizardry. Although the series has sold 500 million copies globally, not everyone saw the success Rowling had envisioned from the start.

Eight publishers rejected the original novel Harry Potter and the Philosopher’s Stone, which sold as the “Sorcerer’s Stone” in the U.S.

Joanne Rowling first had the idea to write the novel in 1990. Between then and 1997, when it was first published, Rowling faced major hardships. Her mother passed away, she and her husband divorced, and she also gave birth to her first child.

She was a single mother living on welfare.

Then London publishing company Bloomsbury gave the OK to publish her story, and the rest is history. But Rowling hasn’t forgotten her humble beginnings, and has shared her difficult experiences in a book titled: Very Good Lives: The Fringe Benefits of Failure and the Importance of Imagination. Here is how Rowling explains the “benefits of failure”…

“You might never fail on the scale I did, but some failure in life is inevitable. It is impossible to live without failing at something, unless you live so cautiously that you might as well not have lived at all – in which case, you fail by default.”

And how you can learn from them…

“Failure gave me an inner security that I had never attained by passing examinations. Failure taught me things about myself that I could have learned no other way. I discovered that I had a strong will, and more discipline than I had suspected; I also found out that I had friends whose value was truly above the price of rubies.”

11. Oprah Winfrey

Oprah Winfrey campaigns for Democratic Presidential candidate Barack Obama at UCLA

She’s a billionaire, and hailed as the “Queen of Media” by many. But her life wasn’t always fit for a queen.

In fact, Oprah Winfrey overcame growing up in poverty. She chased her dream, and created a media empire. And despite all her success, Winfrey is no stranger to failure.

Winfrey started her career in radio and TV broadcasting in 1971, while attending Tennessee State University.

By 1976, she was hosting a talk show called People Are Talking. She worked there eight years, and then landed her own morning talk show at a Chicago station, A.M. Chicago. She beat out her competitor Phil Donahue in ratings. Winfrey then got a part in Steven Spielberg’s 1985 film The Color Purple. The following year, she launched The Oprah Winfrey Show. 

By 1998, Oprah became a household name, but adversity still followed her. She co-produced and starred in a film called Beloved, with hopes of it being a big Hollywood hit. She told Vogue Magazine it was one of her biggest failures, but she worked past it.

At a Harvard commencement ceremony in 2013, she passed on her wisdom of failing and how to overcome adversity to the graduating seniors. The Harvard Gazette quoted her saying…

“It doesn’t matter how far you might rise. At some point, you are bound to stumble. If you’re constantly pushing yourself higher and higher, the law of averages predicts that you will at some point fall. And when you do, I want you to remember this: There is no such thing as failure. Failure is just life trying to move us in another direction.”

And when faced with hardships in life, she said…

“Now, when you’re down there in the hole, it looks like failure. When that moment comes, it’s okay to feel bad for a little while. Give yourself time to mourn what you think you may have lost. But then, here’s the key: Learn from every mistake, because every experience, particularly your mistakes, are there to teach you and force you into being more who you are.”

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