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BOSTON (MainStreet) -- Sometimes opportunity knocks. Sometimes it pounds on the door, screaming to be let in. 

But life is full of regrets: the date you never took to the big dance, the email never sent, choosing salad when everyone else got steak. For business leaders, a bad choice at the crossroads can cost them a fortune. 

M&Ms lost out to Reese's Pieces when

Mars Candy

didn't grasp why it should be featured in



passed on a little sitcom


rode to billions called

The Cosby Show



almost took over


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back in 2006, a move that might have changed its corporate fortunes forever. There was even a handshake agreement between Mark Zuckerberg and Yahoo! CEO Terry Semel for a $1 billion buyout. 

Then the company tried to back away from that deal, making a counter-offer of $800 million instead. Even though the original billion was back on the table several weeks later, by then the damage was done and Zuckerberg, with enough time for second thoughts, quashed negotiations. 

In the company's defense, its blundered negotiations were a byproduct of underperforming earnings and a plummeting stock price, and business history is filled with just this sort of shortsightedness and bad timing. The following are five of the business world's biggest missed opportunities: 

iTunes almost got 'Real'

Steve Jobs had a knack for packaging. The late CEO of


(AAPL) - Get Apple Inc. Report

made design a crucial aspect of every product he oversaw in later years. Apple didn't create the MP3 player, but its iPod became a category killer because of its sleek looks, intuitive interface and the masterstroke of creating that money-shoveling "ecosystem" known as iTunes. 

Credit for what the iPod became actually doesn't rest with Jobs; it was the vision of of Tony Fadell. 

Fadell, an engineer at

Philips Electronics

(PHG) - Get Koninklijke Philips NV Report

, unsuccessfully pitched that company and streaming media giant

Real Networks

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on his concept for the pairing of a music player tied to a


-like content delivery system. 

What others failed to grasp, Apple seized on and brought Faddell in-house (where he remained a senior vice president until 2008 and a contentious

parting of the ways


Real Networks, despite its media focus, failed to see the potential in the technological concept that might have given it the unchallenged digital music stranglehold Apple now enjoys. 

Cats & Beatles

CT Scanners -- often referred to as CAT Scans -- are a staple of modern hospital diagnosis. 

But it took not one but two missed business opportunities to make the technology as commonplace as it is. 

In 1959, neurologist

William Oldendorf

thought of using a series of X-rays to construct the image of a head's topography. Hs initial creation, the earliest prototype of what would become CT scanners, was cobbled together using pieces of a toy train, a record player and an alarm clock. 

Oldendorf, who went on to become a founding member of the American Society for Neuroimaging, patented his idea in 1963. Manufacturers of traditional X-ray technology rejected it, however, dismissing the concept as impractical and expensive. 

"Even if it could be made to work as you suggest, we cannot imagine a significant market for such an expensive apparatus which would do nothing but make a radiographic cross-section of a head," read one of his many rejection letters. 

It took the meteoric rise to fame of The Beatles to give the CT Scan a second chance. 

Godfrey Hounsfield

was a researcher at


, a company with the full name of Electrical and Musical Industries. In 1962, the company was floundering, having sold off its computer division. Salvation came from an unlikely source when the company's music division snatched up a young quartet that had been rejected by

Decca Records

. That band, The Beatles, shot quickly to international fame and fortune. 

Their loss was

EMI's gain

, and the company, soon flush with cash from the signing, could afford to let Hounsfield pursue an even more polished, marketable and faster version of the device.

The company that almost killed Microsoft

Bill Gates almost lost his biggest business break, an upset that would have made Gary Kildall and his company

Digital Research

the king of the personal computer and possibly relegated


(MSFT) - Get Microsoft Corporation Report

iconic leader to the "where are they now" file. 

In 1980,


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was on the hunt for software to power its new personal computers.

Gates and the infant Microsoft

were in the running, as was an operating system made by Digital Research. 

The story of what happened next is pure


. The more commonly repeated tale is that IBM was ready, willing and able to give Digital Research and its CP/M operating system the nod, but the plan fell apart because Kildall decided to go flying instead of taking a meeting and left his wife in charge of negotiations. Dorothy Kildall, reportedly, found some aspects of IBM's offer to be lacking and killed the deal. 

Instead, IBM put its digital eggs into the MS-DOS basket once Gates proved his OS would be a cheaper alternative. 

To take that version of the story at face value certainly shows Kildall missing out on a once-in-a-lifetime opportunity. 



-- and there are many -- dispute that version of events and have instead accused IBM and Gates of

underhanded dealings

(among the complaints is an explanation that the company intentionally waited until Kildall was in-flight, bringing documents to them, when the fateful call was made). 


Perhaps the most infamous tech tale of looking a gift horse in the mouth is


(XRX) - Get Xerox Holdings Corporation Report

basically giving away the revolutionary technology that gave birth to Apple. 

Xerox engineers at its Palo Alto Research Center had created the Alto, the first computer to use a graphical user interface and a mouse instead of on-the-fly coding. 

One problem: It was 1973. 

With personal computers merely a futurist flight of fancy, Xerox had little use for the system aside from units that found their way onto college campuses in the ensuing years. 

Fast-forward to 1979, when Steve Jobs struck a deal with Xerox. For

a behind-the-scenes tour

of PARC, he would offer 100,000 shares of pre-IPO stock for $1 million. It proved an unbelievable bargain for Jobs, who walked away with the GUI knowledge needed to make the early Lisa and Mac computers that made Apple a user-friendly hit with consumers. 

That's the popular legend of how it all went down, but it may

not necessarily be accurate

. It has been argued that Jobs left Xerox PARC with inspiration rather than trade secrets. Apple had already been building a hardy GUI-based operating system and, if nothing else, his tour gave him a glimpse at its true potential and pushed the Apple team into overdrive. 

But even if the tall tale of Jobs the pirate isn't quite accurate, this much is true: Xerox was far too slow to capitalize on its creation, and when it did launch the Xerox Star, a successor to the Alto, in 1981 it was too little, too late. Apple had an insurmountable head start. 

The anti-social network

There is no denying that


(GOOG) - Get Alphabet Inc. Class C Report

is one of the most successful companies on the planet. 

But it could have been much, much bigger. 

Back in the late 1990s and into the early years of the 21st century, Google was far from a preeminent search engine. Among the many competitors in that space were

Alta Vista










Ask Jeeves


Web Crawler



and, of course, Yahoo!. 

Over time, Google rose to the top for a very simple reason: Its underlying process was faster, more efficient, more targeted and more accurate. Google wasn't the first, but it may very well have been the best. 

Given its focus on mining, interpreting and selling data, one might imagine that Google would have been in a position to nudge its way into the social networking space of Facebook and


. It tried and failed. 

Google Buzz was a disastrous attempt that ran afoul of Gmail users who found themselves "opted in" without their say and exposed to privacy-related blunders. Lawsuits and

action by the Federal Trade Commission

followed and lingered. 

Google is trying to once again wedge itself into the social media space -- with a mixed verdict -- via Google+ but is already behind the ball, just as all those Magellans and HotBots were. 

Facebook is not only a nearly invincible target to challenge for Google's just-now-getting-serious approach to social media, it has occasionally popped ahead of its would-be rival in number of visits per week, engages users for up to seven times longer and is starting to drive more traffic to a variety of Web sites than does the search engine giant. 

Could Facebook eventually prove better at search than Google? It probably has a better chance at that accomplishment than Google+ unseating its popularity in social networking. 

--Written by Joe Mont in Boston.

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