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5 Inspiring Failures from Famous Entrepreneurs

Updated: 17 hours ago

Failure might seem like a dirty word in business, but it’s pretty inevitable. For an entrepreneur – or anyone looking to progress their career – the chances of getting everything right first time, as you take that next big step, seize new opportunities and act on new ideas, is next to none. As Richard Branson once said: “You don’t learn to walk by following the rules. You learn by doing, and falling over.”

Rather than being brought down when things don’t go right, here at Appco UK we believe in recognising those moments as important lessons – understand what went wrong, how to fix it and (try) not to make the same mistakes again.

Don’t believe us? Here are five famous “failures” who went on to hit the big time in their chosen careers.

1. Yahoo founder Mark Cuban

He’s now worth more than $3.5 billion, but this tech entrepreneur’s achievements came off the back of numerous professional “failures”.

Cuban failed as a carpenter, a cook and a waiter, and was fired from his first sales job with a software company. His first business venture was an unsuccessful foray into selling powdered milk and he recalls having to turn the lights off in his home because he couldn’t afford the power bills.

2. Oprah Winfrey

She’s been dubbed the Queen of All Media, but Oprah Winfrey was actually fired from first television job.

At 22, she became a co-anchor on a small TV station, but the success was to be short-lived. She was sacked after seven-and-a-half months, with a producer telling her she became to emotionally invested in her stories and was “unfit for television news”.

3. Hershey Food Corp founder Milton Hershey

That last name is all too familiar to us now, but before he started the Hershey Chocolate company in 1894, Milton Hershey went from state to state in the US, starting and shutting down unsuccessful sweet shops again and again.

On one occasion a group of children stampeded his delivery wagon, taking off with his entire stock, and forcing him into bankruptcy.

4. American Vogue editor Anna Wintour

She’s now probably the most notable figure in the world of fashion, but Anna Wintour lost her first job as a junior fashion editor at Harper’s Bazaar. Her ideas created a stir in the industry, but after only nine months she was sacked because the editor thought she was too edgy.

5. Walt Disney

With “Walt Disney” pretty much a synonym for imagination, it’s hard to believe that the man could have been fired for lacking creativity. But in 1919, the American entrepreneur lost his job at a newspaper because the editor felt he “lacked imagination and had no good ideas”…!

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