5 Epic Early Failures of Famous Entrepreneurs

Before they built their million- and billion-dollar companies, these founders faced significant but little-known setbacks

Written by Murad Hemmadi

The path to entrepreneurial success is a long and winding road, as anyone who’s ever started a business can probably attest. And few founders hit on a winning idea or solution at the first attempt.

U.K. loan provider Fleximize plotted the careers of 33 company founders who have become inspirational and widely-celebrated exemplars of entrepreneurial success. The visualization shows how many false starts, strange detours and outright failures they ran into on the way to starting their most successful ventures. Some of these mis-steps have become the stuff of entrepreneurial legend, but others are probably unknown to anyone but biographers. You’ve probably heard the story of Steve Jobs’ ouster from Apple, but did you know that in 1991 Jobs fired half the staff at the five-year-old Pixar because the company had yet to make a profit?

Here are a few other low-profile failures from entrepreneurs who later hit it big.

His beaming face adorns tens of thousands of KFC outlets around the world today, but as a young man Colonel Harland Sanders was fired from several jobs for fighting and insubordination.And his first major entrepreneurial success actually came about in tragic circumstances. At 45, he was running a Shell gas station in Kentucky and feuding with another pump proprietor. In a shootout between the two, the rival killed a visiting Shell district manager and was convicted, eliminating Sander’s competition.

In 2006,Anita Roddick sold The Body Shop to global cosmetics giant L’Oréal for £652 million, pocketing about a sixth of that herself. But the beauty products retailer was actually her second entrepreneurial venture. At 31, she and her husband opened a boarding house in seaside town of Littlehampton, England. The hospitality business didn’t appear to suit her, though—the Roddick’s shut their doors after struggling to turn a profit.

Plenty of entrepreneurs are celebrated in small ways, but few get a televised parade every year in their name. But beforeRowland Hussey Macy could build his eponymous New York department store, his first two retail endeavours had to fail. At 22, Macy saw his Boston needle-and-thread store go bankrupt; two years later, his first dry goods store also went under.

Think of the music on your phone as Sony’s gift to you. The evolution of portable music players more or less begins with the Walkman, which the company launched in 1979. But before he started Tokyo Tshushin Kogyo, the venture that was later renamed Sony, Masaru Ibuka had two fiery failures. Ibuka’s first electronics product, a rice cooker, had a tendency to burn its contents, while his second, a heated cushion, tended to overheat.

Now a brand in his own right, Richard Branson built the Virgin Group into a multi-industry conglomerate. But that enthusiasm for entering new lines of business has occasionally gotten the sometimeCanadian Business columnist in trouble. In 1992 Branson sold Virgin Records to the then-Thorn EMI for £500 million to finance his airline, Virgin Atlantic.

The moral of these failure-to-phenomenal-success stories? You don’t have to get it right the first time.


Which of these failures is most surprising to you? What’s your biggest failure, and what did you learn from it? Let us know by commenting below.

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