Opinion

The entrepreneurs who fought failures to become billionaire business icons

19 min read

03 November 2015

Former deputy editor

The UK has been criticised for not embracing the American culture of failure. Indeed, in the US it's considered something of a badge of honour for an entrepreneur to fail before achieving success with a business venture. As such, we've rounded up key cases of individuals with superhuman tenacity as a reminder to never back down.

Former Dragons’ Den investor Piers Linney spoke with Real Business earlier this year and explained that he’d like to see Britain adapt to the trend witnessed on the other side of the Atlantic.

He said that even the most successful entrepreneurs will have experienced difficulties ahead of greatness, but is of the opinion those struggles make you a stronger business leader – as long as you learn from them.

“In America people prefer failure. If you turn up over there with a great idea but haven’t had an experience as an entrepreneur or with failure, you’d find it harder, whereas the Brits need to get over that,” he said.

“There’s a mantra now in the US about failing fast – get a minimum viable product onto market, try it and if it doesn’t work, move onto the next thing, but it doesn’t fit into the way of thinking here.”

From Linney’s point of view, if something isn’t working then you need to cut your losses quickly – that’s a lesson he’s learnt along the way, having made investments that didn’t go according to plan.

“I’ve been involved in businesses where we tried things, it didn’t work out, and we paid everyone off and shut it down, which is fine.

“Failure is okay, but it doesn’t mean you can raise loads of money to blow up every couple of years and take people down with you – that’s not acceptable. You’ll soon find you won’t be able to raise anything.”

Computer programmer Brian Acton is an interesting case. Having applied for a job at Twitter in May 2009, he was unsuccessful in his application, but he remained undeterred and kept his eyes open for the next opportunity.

Later in the summer that same year, he applied for a position at Facebook – but seemingly his social networking career wasn’t meant to be as he turned to Twitter to broadcast the news, which revealed he was still optimistic.

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The optimism paid off.

Just a couple of months later and Acton had become co-founder of WhatsApp – as in the instant messaging app that Facebook bought for $19bn in February 2014.

Interestingly, fellow WhatsApp co-founder and CEO Jan Koum – who worked with Acton at Yahoo – was also rejected from a position at Facebook. 

He now sits on the board of directors alongside Mark Zuckerberg, and WhatsApp reached 900m users in September 2015.

Indeed, the app is fast approaching the big one billion user milestone, a figure parent company Facebook achieved on mobile in a single day for the first time in August.

“WhatsApp’s extremely high user engagement and rapid growth are driven by the simple, powerful and instantaneous messaging capabilities we provide,” said Koum.

“We’re excited and honoured to partner with Mark and Facebook as we continue to bring our product to more people around the world.”

Continue reading on the next page for more individuals that secured victory, even when it looked out of reach.


It’s almost impossible to walk along the street without clapping eyes on someone using a smartphone – many of which are of the Apple variety.

And while the casual iPhone owner may not know – or care – about the origin of their beloved device, technophiles and business leaders globally look to Apple founder and former CEO Steve Jobs as a visionary, even in death.

Although he only passed away four years ago, the leader has already been portrayed on the big screen in not one, but two films. Ashton Kutcher played the Apple creator in the 2013 movie Jobs, while Michael Fassbender has given it a try and slipped on the turtleneck in this year’s Steve Jobs.

Jobs’ biographer Walter Isaacson described him as the “creative entrepreneur whose passion for perfection and ferocious drive revolutionised six industries: personal computers, animated movies, music, phones, tablet computing, and digital publishing.”

However, that passion for perfection and ferocious drive are ultimately what became Jobs’ downfall.

Jobs had brought in Pepsi head John Sculley to be Apple’s CEO and the partnership worked initially, until Sculley convinced the board that its co-founder had to be stripped of power. In 1985, Jobs’ control over Macintosh innovation was removed and he became an outcast among his peers.

Recalling the events, Jobs had said: “I was out – and very publicly out. What had been the focus of my entire adult life was gone, and it was devastating. I was a very public failure.”

However, Jobs refused to be defeated and launched a new computer business called NeXT, which specialised in both hardware and workstations.

And in 1986, Jobs funded a project from Star Wars creator George Lucas’ Lucasfilm, which he then proceeded to develop into Pixar Animation Studios. In 1995, Pixar released Toy Story – the world’s first feature-length computer-animated film, which changed cinema forever.

Jobs was flying and Apple, recognising its error, acquired NeXT in a $427m takeover in 1996 that saw Jobs soon appointed as the new Apple CEO. 

And then there was Disney’s $7.4bn acquisition of Pixar in 2006.

Jobs set to work to transform Apple and was instrumental in its transition to increased sales and the cult-like following it has today, having masterminded products including the iMac, iTunes, iPod, iPhone and iPad.

Read more on failure:

Of course, Twitter co-founder and CEO Jack Dorsey has had a similar experience to that of Jobs – resulting in him getting compared to the former Apple chief for the similarities.

After being ousted by his board in 2008, Dorsey launched mobile payments business Square in 2010, which was founded the year before, and the firm is on its way to go public.

Twitter’s CEO Dick Costolo left his post in June of this year, which resulted in Dorsey standing in during a search for a replacement. But in October 2015, after much speculation, it was officially confirmed that Dorsey would retain the role permanently.

Dorsey is also a board member of Disney, as was Jobs.

Continue reading on the next page for the two female entrepreneurs that defied the odds to secure billionaire status – one of whom actually lost the title due to so much charity work.

Image: Disney/Pixar

Even without the Winfrey, Oprah’s name is known the world over.

Born into poverty and a violent upbringing, Winfrey had a rough start in life. However, moving to live with her father improved her education and opportunities and she secured a scholarship to Tennessee State University.

After winning a beauty pageant, Winfrey went on to secure a part-time news job at a local radio station. She eventually moved into TV in 1976 and was named co-anchor on the six o’clock news with Baltimore’s WJZ-TV.

The position was short-lived though and she was fired after seven and half months for being “too emotionally involved”, and found herself moved onto a local talk show for the studio.

Winfrey moved on to Chicago in 1983 and it was the Windy City that changed her failure into a success.

Despite having started in news, the talk show movement seemingly worked well for her. While the 30-minute show she was given had started with low ratings, they soon spiked through the roof.

Three years later and The Oprah Winfrey Show was born.

Today, Winfrey is worth around $3.1bn.

Discussing her experience of the anchor upheaval, she said: “Not all my memories of Baltimore are fond ones. But I do have fond memories of Baltimore, because it grew me into a real woman. I came in naive, unskilled, not really knowing anything about the business — or about life. And Baltimore grew me up.”

In October 2015, Winfrey made an equity investment in Weight Watchers, which she is a member of, and was granted a seat on the health firm’s board of directors. The post will see her act as a strategic advisor to develop the programme even further.

“Weight Watchers and Oprah Winfrey make a powerful combination,” said Ray Debbane, chairman of Weight Watchers International.

“Oprah is a force of nature in connecting with people on a very personal level to live inspired lives. This partnership will accelerate our transformation and will meaningfully expand our ability to impact many millions of people worldwide.”

Never one to stand still, Winfrey also launched a new show called Belief in October to explore religion across the globe.

Another household name is Harry Potter, who was of course created by author J.K. Rowling.

Indeed, it was the creation of the boy wizard and his magical world that saw Rowling become the world’s first billionaire author.

That said, she is so generous with her wealth that she previously lost her billionaire status in 2012.

“New information about Rowling’s estimated $160 million in charitable giving combined with Britain’s high tax rates bumped the ‘Harry Potter’ scribe from our list this year,” said Forbes.

These days, however, Rowling is back to a net worth of $1bn.

The journey to success was not a smooth one for the author, however – which may come as a shock given the sheer mind-blowing popularity and adoration for her novels worldwide.

In her early twenties Rowling had moved to Portugal to teach English, following the death of her mother. While overseas, she married a TV journalist and they had a child together, but the relationship collapsed after two years.

She detailed: “I had a short and really quite catastrophic marriage, and I’m left with this baby – and I’ve got to get this baby back to Britain and I’ve got to rebuild us a life.” The writer referred to the situation as a “complete mess” that hit her hard.

The idea for Harry Potter came to Rowling in 1990 when travelling on a delayed train, and the next five years were spent planning out a series spanning seven books.

Many rejections came her way during that process, as 12 book publishers shut the door in Rowling’s face. She was even told “not to quit her day job.”

In 1997, Harry Potter and the Philosopher’s Stone was released and the magical madness gradually started to spread from there.

But while writing the first novel, Rowling suffered from depression as a single mother with little money.

She sought help for her condition, having said: “The thing that made me go for help was probably my daughter. She was something that earthed me, grounded me, and I thought, This isn’t right; this can’t be right. She cannot grow up with me in this state.”

That was a long time ago and Rowling has now seen all seven of her Harry Potter books adapted onto the big screen in a huge eight-picture series – final film The Deathly Hallows was split into two parts.

And then there’s been the launch of The Wizarding World of Harry Potter theme park at Universal Studios Florida, and the Harry Potter Warner Bros Studio Tour in the UK.

Her spinoff book Fantastic Beasts and Where to Find Them is also being adapted for cinema and is due for release in 2016.

Furthermore, the author is even moving back into the world of Harry Potter with a fresh story, Harry Potter and the Cursed Child, which will be brought to life as a London theatre production in the West End.

Rowling has been incredibly outspoken about her failures and life experiences over the years, which saw her describe the journey to none other than Oprah Winfrey.

In 2008, Rowling delivered a commencement at Harvard University and took the opportunity to discuss the meaning of failure. This was actually developed into a book, the sales of which are donated to charity.

She said: “I was the biggest failure I knew. Now, I am not going to stand here and tell you that failure is fun. That period of my life was a dark one.

“So why do I talk about the benefits of failure? I was set free, because my greatest fear had been realised, and I was still alive, and I still had a daughter whom I adored, and I had an old typewriter and a big idea. And so rock bottom became the solid foundation on which I rebuilt my life.

“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.

“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.”