The Future Is Here
We may earn a commission from links on this page

The 12 Biggest Missed Opportunities in Tech

We may earn a commission from links on this page.

The tech world is full of flops. This ain't them; some of these companies and their products were monstrously successful for a time; others never even had the high expectations and hype required for something to earn the title "flop".

Nope, this is a list of the folks who had something special—a firm grasp on a huge market, or the first fingers on a new one—and squandered it. Maybe it was hubris, a failure to scale fast enough, or an inability to see that they were on to something special. Each of these companies suffered from asleep-at-the-wheelness in some form or another, and allowed others to clean up in a market that they should've owned. These are the guys who coulda been—and maybe once were—contenders.


Could've: Been usable

Somewhere, a giant landfill full of broken plastic AOL CDs is making a TV Indian cry. AOL owned the ISP business. It crushed CompuServe and pummeled Prodigy (remember them?), and, in the process, introduced millions of folks to the Internet and chatrooms and something called a "keyword." Hell, Meg Ryan even made a rom-com that basically took place in AOLand.

But this was a company that was more concerned with sales than scale. It had great ads, offered unlimited Internet when pay-by-the-hour was still the norm, and distributed enough free demo discs to make a bridge to the moon and back a few times over. And yet AOL seemed genuinely caught off guard by its own success. In 1997, it was reported that a whopping 60.3-percent of AOL connection attempts ended in failure—mostly due to busy signals. The "AOL busy signal" became a staple of late night comedy. Worse, when the world moved from dial-up to broadband, AOL seemed utterly uninterested in upgrading its service. Before long, speed-greedy customers were fleeing at far faster than 14.4 kilobytes per second. Today, depending on how you look at it, an AOL email address is either a sign of mental issues or the ultimate old-school badge of honor.


Could've: Scaled into the social networking stratosphere

Never mind that Friendster is still inexplicably popular in the Philippines, the social network's founders must cry every time they see a news story that mentions the words "Zuckerberg" and "billions." Back in 2002, this proto-Facebook had friending and messaging and a wall that you could write on (though they called it "leaving a testimonial") and basically all the building blocks of every social network since. But as Friendster's popularity blasted upwards, the site found itself unable to handle the traffic, and loading pages became a frustrating, laptop-tossing endeavor (script-watchers might recall that even "The Social Network" made a dig at this fail). And so, almost as quickly as they came, Friendster's users left…

[Image: Shutterstock]


Could've: Changed with the times

Time was, if you wanted to watch a movie at home (and didn't happen to have an awesome indie video store nearby), you'd go to Blockbuster. But here's the thing about Blockbuster: Nobody liked them. Ever. Even when people rented movies from the company, there was still an almost universal resentment at its crappy selection, inability to keep movies in stock, long lines, and mother$#&@ing cr!#su*(ing $*&@damn late fees.

This was, in the grand corporate tradition, completely surprising to Blockbuster, which never seemed to understand how much people hated it. The company somehow deluded itself into thinking that, even with a nascent Netflix nipping at its heels, customers would somehow stay loyal to the brand and its dying business model. Sure, when it was too late, the company put out a few half-assed attempts at stealing Netflix's business model, but none of them caught on. When Blockbsuter should have shown humbleness and a willing to work extra hard to keep its customers, it arrogantly pretended as if Netflix didn't exist. To Blockbuster, Netflix was a mere mosquito… until it bit it into bankruptcy. But hey, good news for Dish Network, who picked up the ailing VHS hawk-shop chain for a $320-million-dollar song last year.


Could've: Followed up the Razr

Remember when the Razr was, like, the best gadget ever? This awesomeisity had nothing to do with its user interface (which sucked) or feature set ("feature set" hah!) or any of those things that people care about these days. No, this thing was THIN, and single-phonedly set off a years-long battle to shave ever-more micrometers off the depth of handsets. And boy did this baby sell—the Razr first launched in 2004, and had sold more than 50 million units by the summer of 2006.

But like an aging rockstar who continues to milk that one hit on his journey from arenas to shopping malls to Bar Mitzvahs, Motorola simply couldn't follow up. Worse, you got the feeling that they just weren't trying. Instead of innovating or realizing that things like user interface and might have some bearing on the future, the company simply chose to release slightly different versions of the exact same phone. And, as the law of diminishing returns should have made ridiculously obvious, consumers gave fewer and fewer shits with each one. While Apple was putting out the iPhone, Motorola was still releasing Razrs and Krzrs (remember that one?) and Razr2s. Bottom line: the Razr was the golden clamshell-shaped handcuff that caused Motorola to completely miss the fact that the mobile world was moving on, and that users cared as much about software design as hardware. Yes, the MotoQ was hot; but it also ran Windows Mobile, and that shit didn't fly after a while.

Even Motorola's successful forays into Android phones couldn't save the company's rep, and it was eight years before Moto released anything that could objectively be called hot. By the time the carbon fiber-swaddled Droid Razr came out, Motorola was firmly in Google's clutches: an in-house patsy walking down the road to irrelevance.


Could've: Not sat by idly while Facebook destroyed it

Where Friendster was slow, MySpace was FAST. In the early days of the social network wars (meaning 2003), simply showing up was half the battle, and MySpace's killer app was that it actually worked. It also gave the world a few genuinely good bands, made an art form out of the narcissistic self-portrait, and launched a thousand media profiles of MySpace Tom (and... uh… Dane Cook).

But the site had a fatal flaw: It was a chaotic shit show. Granted, this is what probably drew a lot of its young'un users to the site in the first place, but there are only so many times you can deal with auto-loaded screamo songs and seizure-inducing animated gif backgrounds before you yearn to move to the social networking suburbs. Worse, News Corp. (who bought the site for the princely sum of $580 million in 2005) did nothing to nurture it or clean up its user experience. Meanwhile, Facebook added features and proceeded to eat its lunch.


Could've: Owned the tablet market

Back in 2001, when the iPad was likely little more than a twinkle in Steve Jobs' eye, Microsoft pulled out the mean feat of simultaneously inventing the modern tablet PC, and tricking itself into thinking that nobody would ever want one. Granted, maybe it was a bit ahead of its time—cheap capacitive displays that would allow tablet makers to ditch styluses were still years away, as were decent mobile operating systems that would make these things practical with anything other than full-blown Windows. But Microsoft still squandered a nearly decade-long head start that should have allowed it to study the category, and eventually evolve it into a mainstream consumer-friendly product. Today, the tablet-friendly Windows 8 has a helluv an uphill battle ahead of it.


Could've: Properly supported the iPhone

You're given a multiyear exclusive on the single most desirable gadget ever created. What do you do? Fail to properly scale up your voice and data networks in major cities, and drive the entire tech (and comedy and consumer and news) world into turning your brand name into a synonym for bad service. The iPhone's "unexpected" bulge in traffic on the AT&T network was a surprise to nobody but AT&T, and the company's initial handling of the iPhone was basically a long, slow, painful-to-watch public relations train wreck.


Could've: Ruled portable music

Ah, the 80s: when Sony invented the Walkman—and the portable music category. The company repeated with the Discman (world's first portable CD player), and had a chance to pull a hat trick with digital music players. But Sony's religious devotion towards proprietary file formats meant that it took years for it to even release a digital audio player that could play MP3s. Early products forced users to use sluggish software to convert their tracks to a proprietary format. You know what's easier than spending your time dutifully converting lawfully acquired audio files? Napster. And just about any other portable audio player.

How historically important is this fail? Well, if it weren't for the iPod's outsized success (which became a crossover hit partially because nobody else was producing any decent MP3 players—Sony included) the modern Apple as we know it wouldn't exist.


Could've: Created the netbook

We're not going to talk about Web OS right now—the wound is just too fresh. This is about a different colossal screwup.

Remember Palm's Foleo? It was a netbook before netbooks existed. Announced in 2007, the product—which was billed as something between a smartphone and a laptop—promised a carry-anywhere size and battery life, along with a low-ish price made possible by its puny power. But dismayed by a public reaction that could best be described as "bewildered," Palm cancelled the product before bringing it to market. Oh, what folly: Months later, netbooks such as the Asus Eee PC had nicked the Foleo's formula of low cost, low power, and small size. And they were everywhere. As an eloquent member of the Internet puts it: "Had it been released, the Foleo would have been the founding device in the [netbook] category." Instead it's in the Vaporware Hall of Fame.


Could've: Done so, so, much differently.

Yahoo could've bought Facebook (maybe). Yahoo could've been bought by Microsoft for far more than it's worth now. Yahoo could've actually done something with big-time acquisitions such as Flickr and Yahoo could've even hired a CEO who didn't lie about having a computer science degree. Le sigh.

[Image: Michael Macor / The Chronicle]


Could've: Mattered

Working in the news industry in 2008, there was no bigger satisfaction than seeing your story pop up on the front page of Digg. For a while, it was sort of an open secret that media organizations would regularly tailor their coverage around what was likely to pop on the social news site (lots of lists). But it took just one completely bungled redesign to turn the company into the MySpace to Reddit's Facebook. 2010's Digg v4 may go down in history as the most hated redesign in modern Web history. The site became unstable, unsightly, and unfun. Features went missing, and so did its users.


Could've: Not let the smartphone world slip through its fingers