All Frontline Leadership Spotlight on Leadership

Failure to Success – 3 Highly Successful Leaders Who Have Overcome Failure

No matter your walk of life, no one seems to like failure. It’s not something that many of us seek in our endeavours in business or otherwise; and yet some of the world’s most successful individuals haven’t just acquainted themselves with the premise, they’ve embraced it. 

Whilst industry leaders such as Bill Gates look at success as the goal, he, along with many others, firmly believe that failure often provides the critical lessons and insights that allow them to plot the best path to bring their objectives to fruition. Other leaders such as James Dyson persist in pushing boundaries and embracing their mistakes to this day, accepting that failure is a necessary investment into success.  

This article, the 2nd in our JMW Consultants sponsored Three Leaders series, will look at some of the business world’s most inspiring failure-to-success stories: Bill Gates, Ariana Huffington, and James Dyson, each with very different experiences but inextricably linked by their stories of abject failure before achieving stratospheric success. 


Let’s start with Microsoft founder Bill Gates.


Bill Gates: From Six Years of Failure, To Six Years of Unmitigated Success 

The Bill Gates of today is known for creating the hugely successful tech giant Microsoft which transformed its business by embracing the cloud in 2010 with the launch of Azure. However, less is publicised about his first venture Traf-O-Data. 

The idea was conceived between Gates’ long-time friend and future business partner Paul Allen. The venture’s goal was to read information from roadway traffic counters and then help traffic engineers by creating automatic reports. Before Traf-O-Data, traffic flow patterns were measured manually via a pressure-sensitive rubber tube which subsequently punched holes into a paper tape to record passing vehicles.  

Gates was so convinced of the business’s merits, he ditched his Harvard education and dreams of becoming a lawyer to obsess over computerising analogue processes with his new business partner. 

The problem was that Traf-O-Data was an unmitigated disaster. The company’s product, the Traf-O-Data 8008, which read traffic tapes and processed the data automatically, never got off the ground after a string of failures at meetings with local county governments. As Gates recalls, the first-ever meeting was perhaps the most catastrophic, “the device didn’t even work during the demonstration.”

After six years and countless hours, Traf-O-Data had amassed $3494 in losses and was shut down in 1980. Many would have forgiven Gates for giving up at that point and moving on to something much safer. But both he and his partner Allen pushed on with a company they had started not long afterwards, Microsoft (short for micro-computer software). With Traf-O-Data in a state of dying embers, Gates upped and left Albuquerque, New Mexico and headed for Bellevue, Washington in late 1979. 

If the years of 1974 to 1980 is a story of disastrous failure, the period of 1980 to 1986 is a tale of unmitigated success. Everything turned around when Gates led Microsoft into the operating system (OS) business. The company managed to win a now-famous contract to supply the operating system for the IBM Personal Computer. This award led to the development of MS-DOS, the first widely-distributed personal computer operating system. 

After further iterations, the graphical version of MS-DOS, Microsoft Windows, was released five years later in 1985. In 1986, Microsoft went public, and within a year, Bill Gates became the youngest self-made billionaire. In the space of six years, Gates emerged from total failure to the darling of the computer software industry and has continued to remain one of the wealthiest individuals on the planet ever since.

In many ways, Gates has inspired the whole “fail fast, fail often” mantra pursued by many Silicon Valley startups that have followed in his footsteps. As Gates reflected much later when asked about the rip-roaring success of Microsoft, “it’s fine to celebrate success, but it’s more important to heed the lessons of failure.” Many have since sought out failure in a bid to secure some of those seminal stepping stones to success. 

What is perhaps less explicit, but of equal value is the lesson learned around a leadership that is equipped to embrace the future.  As is undeniable, Gates’ ambition for every desk to house a personal computer was realised and paved the way for today’s hyper connectivity.  If there’s one facet of effective leadership that Gates demonstrates best, it’s about making a decisive impact above and beyond what might happen anyway, with an identified purpose.  A purpose that is worth repeating, even though it often yields expensive failures in order to reach the other side. 

Coincidentally, Gates’ description of failure (as a stepping stone to success) is something that our next person of interest, Ariana Huffington, attributes to her mother.


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Ariana Huffington: The Master Reinventor 

Bill Gates faced one crushing failure in his business career, but Ariana Huffington has perhaps had to deal with more disappointment than any other entrepreneur. Two failed relationships, four forced relocations, 37 publisher rejections and one crushing political defeat preceded her rise to prominence as the founder of one of the most prominent media outlets in the world.

Ariana Huffington’s journey is both fundamentally unique and compelling,  meaning that it’s rather challenging to do it justice in a short review. However, concerning her experience with failure, it’s fair to say Huffington has had her fair share. 

After moving from Greece to England and attending Cambridge University, Huffington managed to publish her first book. However, after a lukewarm reception, her second book was not an easy sell. She was rejected no less than 37 times before winning a publishing contract for her second. At one point, she had to plead with a bank manager to give her a loan (despite the fact she had no assets to speak of) to continue the pursuit of her aspirations. It saw her through another 13 rejections, before finally gaining an acceptance letter at the 38th attempt. She’s since become an acclaimed author of fifteen different books. 

The next big lesson in failure was in politics. After moving to America, Huffington eventually became a power-broker in Washington for her then-husband Michael Huffington. However, he came out as bisexual, and their relationship and her time in the Capital came to an end. She decided to reinvent herself once again by moving to California and switching sides from Republican to Democrat. She ran in the 2003 election for Governor against Arnold Schwarzenegger. However, her campaign was disastrous. In total, she won less than one per cent of the vote (0.55%). 

Unperturbed, she shrugged off defeat and flung herself into understanding how her first passion, journalism, could be melded with the internet. Together with Andrew Breibart (who ironically later created the far-right Breibart news), Jonah Peretti and Ken Lerer, she launched The Huffington Post as an alternative voice to the right-leaning, conservative news site Drudge Report

The strategy was to focus on winning clicks above all else and it was a tactic that worked wonders. This innovative, search-engine-optimised journalism style soon caught the attention of investors and the online news outlet was initially acquired by AOL for just north of $300 million. She stayed on as Editor-in-Chief until 2015 when Verizon acquired AOL itself for $4.4 billion. She has since gone on to found and lead a new media and technology organisation, Thrive Global, which has been valued at more than $120 million. 

On failure, Huffington recalls her mother telling her as a teenager that, “failure is not the opposite of success, it’s a stepping stone to success.” Huffington still remembers her mother’s advice when looking back on her career, “I think she would really enjoy how many times I had let myself fail along the way.” 

As with the example of Gates, there is perhaps an additional driver to managing the failure and keeping her drive. Her career illustrates a strength of purpose, the Huffington Post being defined as providing journalism with social impact; a liberal voice that raises awareness of the key social, political and environmental concerns.


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James Dyson: The Epitome of Perseverance 

In many ways, the Dyson founder’s story is summed up best by an often-quoted phrase by another serial inventor, Thomas Edison. During his crusade to find a commercially viable lightbulb, a reporter allegedly asked Edison about failing with 1,000 prototypes of the lightbulb. He retorted, “I have not failed 1,000 times. I have successfully discovered 1,000 ways that it won’t work.”

If 1,000 failures at getting it right tested Edison, spare a thought for James Dyson as he passed the 5,000-mark on his way to creating his first-ever bagless vacuum (DC01). That’s right, he devoted 15 years of his life to creating 5,127 different vacuum prototypes before finding one that worked as well as he had envisioned all those years ago. 

After having 5,000 failed attempts, most entrepreneurs would have, quite rightly, either given up or pivoted, but Dyson kept at it with an unrivalled belligerence that eventually saw him develop his revolutionary bagless cyclonic separation technology. Dyson comments on the toll this period had on his life:

‘There are countless times an inventor can give up on an idea. By the time I made my 15th prototype, my third child was born. By 2,627, my wife and I were really counting our pennies. By 3,727, my wife was giving art lessons for some extra cash. These were tough times, but each failure brought me closer to solving the problem.’

With hindsight, we can say that his unmatched perseverance has paid dividends. Since coming to market in 1993, Dyson’s company has become now a global behemoth, selling bagless vacuum cleaners and other pioneering household and commercial appliances in over 50 countries. 

But even a knight of the realm and multi-billionaire still gets it wrong. Dyson’s long struggle and failures with his vacuum prototype are only the tip of the iceberg. For instance, he scrapped the Dyson washing machine after five years because he couldn’t figure out a way to manufacture it economically. Worse, he’s fresh off the high-profile failure of Dyson’s much anticipated electric car division into which he ploughed £500 million of his personal fortune.  

It seems that failure is hardwired into this passionate inventor’s DNA. But it’s his desire to make a decisive impact on the efficiency and the effectiveness of an existing design  that has enabled this leader to overcome more failures than the average person has had hot dinners.


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Haig Barrett is partnering with JMW Consultants for our Spotlight on Leadership series: Shaping the Future™.  JMW are expert in developing leaders and teams fit for transformation and this collaborative series has been compiled to provide valuable insights and strategy for business growth and accelerated performance.