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When it comes to making business decisions, there's always an element of risk. Sometimes taking risks pays off, sometimes it doesn't. Indeed, there are certain stories in the business world that involve executives kicking themselves for not taking a chance.

Check out this gallery for some of the biggest missed business opportunities ever.

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In 2005, Mark Zuckerberg met with MySpace founder Chris DeWolfe to discuss MySpace’s acquisition of his then-fledgling social networking site.

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DeWolfe reportedly turned down Zuckerberg’s US⁠$75 million ask⁠—a poor decision judging by MySpace’s subsequent demise and Facebook’s meteoric rise.

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It’s very difficult to imagine listening to music on an iPod made by anyone other than Apple. Yet if it weren’t for a pivotal decision by tech company Real Network, that might be our reality.

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Before Tony Fadell teamed up with Steve Jobs to create the new, sleeker MP3 product, he pitched it to his then employer, Real Network. It was only after their rejection that he turned to Steve Jobs.

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At a fateful meeting in Dallas, Texas in September 2000, movie rental company Blockbuster turned down the opportunity to purchase struggling young company Netflix.

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Before Netflix got into streaming and took over the world, it was a DVD-by-mail rental service, which apparently wasn’t attractive enough to former Blockbuster CEO John Antioco.

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In 1999, Excite was second only to Yahoo in the ranking of dot.com boom search engines. By 2001, it had filed for bankruptcy.

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In a questionable decision by CEO George Bell, Excite turned down the chance to buy Google for US$750,000.

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Before 'Harry Potter' was a US$14 billion franchise, it was a pile of handwritten papers that J.K. Rowling was struggling to get published.

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The first agent she approached gave her a swift "no," and, while the second took her on, it was only as a wild card shot that Bloomsbury agreed to publish.

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In 1979, a young Bill Gates offered to sell a majority shareholding in Microsoft to the business magnate and founder of Electronic Data Systems, Ross Perot.

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Although it was actually Perot who approached Gates in the first place, he eventually turned down the ask of US$60 million, as he felt it was too steep.

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Bill Gates almost missed out too, however, when he turned down the opportunity to license his operating system to IBM and instead pointed them towards Digital Research.

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Luckily for him, Digital Research asked for too much and IBM came back to Gates.

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In the history of computers there’s Apple, there’s Microsoft, and then there’s the lesser-known Xerox PC.

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The first Xerox Alto machines were introduced in the early 1970s, but there was no market for PCs and Xerox didn’t know what to do with the technology.

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As a youngster, Steve Jobs worked as a game designer at Atari. When it came to raising capital for his new computer project, he first approached his boss, Nolan Bushnell.

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Bushnell was offered a third of the company for US$50,000—an offer that he likely regrets turning down.

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When Steve Wozniak was working for Hewlett-Packard in the 1970s, he tried to get the company excited about his new personal computer project.

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When his proposals fell on deaf ears, he turned to Steve Jobs, with whom he pursued the project from a garage.

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It could be said that Kodak's decline was an inside job—the digital camera technology that ruined camera film was actually the brainchild of one of the company’s employees.

▲When engineer Steven Sasson first came up with the idea for the technology, he was met with criticism from Kodak, who felt it would threaten traditional film and suppressed it.
▲

When the four boys from Liverpool approached industry big dog Decca Records for a contract, they were met with a resounding "no."

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Decca felt the era of guitar bands had passed, and so The Beatles signed with EMI instead.

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When Alexander Graham Bell first sent speech via a gadget he named the telephone, he offered the patent to Western Union for US$100,000.

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Western Union said "no" to purchasing a device they described as "idiotic." To them, it couldn’t possibly rival the convenience of the telegraph.

See also: The power of simplicity: how one logo built a global brand

 

The biggest missed business opportunities in history

Sometimes executives regret not taking risks on certain opportunities

05/05/25 por StarsInsider

LIFESTYLE Finance

When it comes to making business decisions, there's always an element of risk. Sometimes taking risks pays off, sometimes it doesn't. Indeed, there are certain stories in the business world that involve executives kicking themselves for not taking a chance.

Check out this gallery for some of the biggest missed business opportunities ever.

  • NEXT

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