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.

Let’s explore some of the biggest missed business opportunities ever.

MySpace and Facebook

Mark Zuckerberg met with MySpace founder Chris DeWolfe to discuss MySpace’s acquisition of his then-fledgling social networking site, Facebook in 2005. DeWolfe reportedly turned down Zuckerberg’s $75 million asking price—a decision that looks particularly poor in hindsight, given MySpace’s subsequent decline and Facebook’s meteoric rise.

Real Network and the MP3 Player

It’s challenging to imagine using a device other than an Apple iPod for music listening. Yet, if it weren’t for a pivotal decision by tech company Real Network, that might have been our reality.

Before Tony Fadell teamed up with Steve Jobs to create the sleek MP3 product, he pitched it to his then employer, Real Network. Their rejection led Fadell to hire Steve Jobs, changing the course of digital music history.

Blockbuster and Netflix

In September 2000, movie rental company Blockbuster turned down the opportunity to purchase a struggling young company called Netflix. At the time, Netflix was a DVD-by-mail rental service, which didn’t seem appealing to former Blockbuster CEO John Antioco.

This decision proved catastrophic as Netflix evolved into a streaming giant, while Blockbuster filed for bankruptcy in 2010.

Excite and Google

In 1999, Excite was second only to Yahoo among dot-com boom search engines. However, in a questionable decision by CEO George Bell, Excite turned down the chance to buy Google for $750,000. By 2001, Excite had filed for bankruptcy, while Google went on to become a tech behemoth worth hundreds of billions.

J.K. Rowling and Publishers

Before ‘Harry Potter‘ became a $14 billion franchise, J.K. Rowling struggled to get her manuscript published. The first agent she approached rejected her, and although the second took her on, it was only as a wild card that Bloomsbury agreed to publish the book. The rest, as they say, is history, with Rowling’s books becoming a global phenomenon.

Ross Perot and Microsoft

In 1979, a young Bill Gates offered to sell a majority share in Microsoft to business magnate Ross Perot for $60 million. Although it was Perot who initially approached Gates, he eventually turned down the offer, deeming it too expensive. Today, Microsoft is one of the most valuable companies in the world, worth over $1 trillion.

Digital Research and IBM

Bill Gates almost missed out, too, when he initially turned down the opportunity to license his operating system to IBM, directing them instead to Digital Research. Luckily for Gates, Digital Research asked for too much, and IBM came back to him. This led to the creation of MS-DOS, which became a cornerstone of Microsoft’s success.

Xerox and the PC

In the history of computers, there’s Apple, Microsoft, and the lesser-known Xerox PC. early 1970s saw the introduction of the first Xerox Alto machines, but due to the lack of a PC market at the time, Xerox failed to capitalize on the technology. The personal computer didn’t become widely used until years later, largely due to efforts by other businesses.

Atari and Apple

As a young game designer at Atari, Steve Jobs approached his boss, Nolan Bushnell, to raise capital for his new computer project. Jobs offered a third of Apple for $50,000—a proposal Bushnell turned down. That third of Apple would now be worth hundreds of billions of dollars.

Hewlett-Packard and the Computer

In the 1970s, Steve Wozniak was working for Hewlett-Packard and tried to get the company excited about his new personal computer project. After his proposals fell on deaf ears, he turned to Steve Jobs. Together, they pursued the project from a garage, which led to Apple’s birth.

Kodak and the Digital Camera

One of Kodak’s own engineers, Steven Sasson, actually invented the digital camera technology that disrupted traditional film, contributing to the company’s decline.

When Sasson first presented the idea, Kodak criticized it, fearing it would threaten their film business. Their failure to embrace digital technology contributed significantly to Kodak’s downfall.

Decca Records and The Beatles

Decca Records firmly rejected The Beatles’ initial approach for a contract. Decca felt the era of guitar bands had passed, so The Beatles signed with EMI instead. This decision cost Decca dearly, as The Beatles became one of the most influential bands in history.

Western Union and the Telephone

When Alexander Graham Bell invented the telephone, he offered the patent to Western Union for $100,000. Western Union declined, calling the device “idiotic” and doubting it could rival the telegraph. This misjudgment allowed Bell’s invention to revolutionize communication, leaving Western Union behind.

These stories highlight how even the most prominent companies and individuals can make significant misjudgments. Sometimes, the opportunities that seem insignificant or too risky can turn out to be the game-changers of the future.

The Information is Taken from Star Insider and MSN