Top Entrepreneurs Who Went Against The Grain

You might be mildly annoyed by the title of this article. You could be gnashing your teeth with indignation, because top entrepreneurs tend to go against the grain by default. You’d be right: nobody ever worked their way to the pinnacle of a multi-million pound empire (or into one of these lists) by going with the grain, hacking away at the same tired old bit of wood as a thousand others and never seeing the wood for the trees. That said, as with anything, there’s doing something and then there’s DOING SOMETHING.

Outlaws from the days of yore did a fair bit of hacking, too, though there were fewer trees involved. We’re not saying you should take Billy the Kid (notorious gun-toting Wild West bandit) as your role model if you want to set up your own business, but you do have to be monstrously resilient. Whatever Billy’s transgressions, it’s safe to say that he had thick skin.

5 top Entrepreneurs who were totally badass

We’ve dug out five stories of entrepreneurs whose thick skin enabled them to fly in the face of adversity. These are people who never faltered in telling their critics – and Sod’s Law – to kindly Naff Off, if you please, until they eventually emerged mostly triumphant (and probably quite tired).

Martha Stewart

Big-time American entrepreneur and bestselling author Martha Stewart is a prime example of making the best of a bad situation. She built up her empire around interior design and catering, and when her company Martha Stewart Living Omnimedia went public in 1999 she earned her place in the halls of business fame by becoming America’s first female self-made billionaire.

Happy ending? Not quite; in 2003, following a stock-trading scandal, Stewart was charged with a long list of nasties including fraud, conspiracy and obstruction of justice and packed her bags for a stint in prison, to be followed by two years of supervised release. Ever the entrepreneur, she resisted the urge to wallow in misery during the incarceration – choosing instead to get a prison job that centred around helping her fellow inmates. After returning to the Land of the Free, she bounced back and basically picked up where she left off. Thick skin. Martha Stewart most definitely has it.

  • OUTLAW SOUNDBITE: “My new motto is: when you’re through changing, you’re through.”


Steve Jobs

We know, we know. Too obvious. But no list of  top entrepreneurs – outlaws or otherwise – would be complete without him.

Now a household name and almost synonymous with digital innovation, Jobs was at the helm of Apple when it churned out the iMac, iTunes, iPod, iPhone and iPad. He was also the force behind the tidal wave of Apple’s “Genius”-led retail stores and the online App Store. But it hasn’t always been plain sailing. He dropped out of college after six months and spent a while gatecrashing creative classes such as calligraphy while sleeping on friends’ floors, relying on the good folk at Hari Krishna for free food and foraging for empty bottles as a source of income. After a stint at Atari and a voyage of self-discovery to India, a felicitous collaboration with Steve Wozniak led to the inception of the Apple Computer Company and the era-defining creation of the Macintosh machine.

Happy ending? Not quite; colleagues described Jobs as “erratic and temperamental” and he was eventually ousted for plotting to overthrow the CEO. Did this spell the end of things? Did it heck! Jobs diverted his attentions (successfully) to a bunch of other projects, such as buying the computer graphics division from a film production company and turning it into the animation behemoth now known as Pixar. The prodigal son found his way home to Apple in 1996, complete with renewed fervour and an arsenal of new ideas.

  • OUTLAW SOUNDBITE: “The heaviness of being successful was replaced by the lightness of being a beginner again, less sure about everything. It freed me to enter one of the most creative periods of my life.”


Peter Jones

Every Brit knows him as the tall one from Dragons’ Den with fingers in many pies. Peter Jones has built up his estimated net worth of £475 million through forays into enough industries to sink a battleship, from computers to specialist recruitment to phones to “experience” gifts to television. He invested some spare change he had knocking around in the acquisition of troubled camera retailer Jessops earlier this year (as you do) with the aim of bringing the brand back from the brink of extinction – and karma fans will be glad to hear that he used his clout and dosh for good by setting up the Peter Jones Foundation and Peter Jones Enterprise Academy.

Happy ending? Well, yes. But not without some hard lessons learned along the way. While in his twenties, Jones’s renegade idea for a cocktail bar inspired by a Tom Cruise film (what could possibly go wrong?) resulted in a loss of £200,000. And because our old friend, Life, likes to kick us when we’re down, this was followed by the collapse of his computer company and a subsequent kiss goodbye to his home and cars. Hotel Mama: place of respite and rebirth for top entrepreneurs and outlaws alike.

  • OUTLAW SOUNDBITE: “Behind every ‘no entry’ sign there’s a door.”


Nikola Tesla

Just to warn you in advance – this one doesn’t really have a happy ending. Sorry (that’s life for you).

Enter everyone’s favourite slightly crackpot genius and social outcast: Nikola Tesla. He invented alternating current, was pivotal in the development of x-rays, radio communication, and other bastions of modern-day technology. Many of the serbian-born scientist’s ideas and inventions are the beef behind the successes of smooth-talking Thomas Edison*. During a particular low-point he was forced to earn his bread as a digger of ditches, but his indefatigable entrepreneurial spirit was undeterred and he churned out enough patents throughout his life to give a microwave a headache.

A good looker and talented salesman, Tesla spoke eight languages and had the capacity to memorise whole books. He also refused to ever visit a doctor, spent most of his life broke, spent all of his life celibate and was obsessed with pigeons. Nevertheless, he lived to a ripe old age, and pretty much all of those 84 years went against the grain. Not to mention the fact that it takes no small amount of resilience to refuse a trip to the doctor after a cab runs you over and breaks three of your ribs (though that might be pushing it somewhat).

  • OUTLAW SOUNDBITE: “Our virtues and our failings are inseparable, like force and matter. When they separate, man is no more.”

*If you want to know more about the extent of this despicable limelight theft, here’s a nice (very non-impartial) thing.


J. K. Rowling

The creator of Harry Potter – a literary magnum opus that defines an entire generation – famously penned most of the series from various cafés while unemployed and scraping by on benefits. She had a difficult childhood, a failed marriage, and a diagnosis of clinical depression. Her mother died when Rowling was young, and she has a broken relationship with her father. These tendrils of misery, instead of suffocating her, spurred her on as a source of inspiration – the soul-sucking Dementors, for example, were borne directly from her struggle against her mental illness.

Happy ending? We all know that this story has only the best happy ending, like, ever. Her work has spawned an immensely successful film series and opened the floodgates for merchandise and computer games. Rowling was named as “Britain’s Most Influential Woman” in 2010 and has been drenched with awards of all shapes and sizes, not to mention honorary degrees from six universities. Thick skin wins again. J. K. Rowling, we salute you.

  • OUTLAW SOUNDBITE: “Failure meant a stripping away of the inessential. I stopped pretending to myself that I was anything other than what I was, and began to direct all my energy to finishing the only work that mattered to me.”

By Corissa Nunn, European Development at Enternships


One thought on “Top Entrepreneurs Who Went Against The Grain”

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