Microsoft's 13 worst missteps of all time

DOS 4.0, Zune, and Windows 8 are but a few of the landmarks among 25 years of failures Redmond-style

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Released in 1995 and abandoned in 1996, Bob didn't live very long, but he left quite a legacy -- I mean, in addition to his obvious design influences on Windows 8.

The Rover cartoon helper in Bob appeared, unchanged, as the Search Companion in Windows XP's Windows Explorer. Rover and his similarly designed cohorts -- Merlin the magician, Earl the surfer, and Courtney (the courtesan?) -- offered to help perform local searches on the Windows XP desktop.

More insidious, a perky offshoot known as Clippy "It looks like you're writing a ransom note. Would you like help?" appeared in Office 97. Clippy (and the Dot, Hoverbot, the Einstein-reminiscent Genius, Scribble the cat, Power Pup, Links the cat, Rocky the dog, and Will as in Shakespeare) shipped with Office 97, 2000, and 2003, only to be tossed out on his curled ear with the arrival of Office 2007 and its equally cloying Ribbon interface. I note in passing that Steve Sinofsky was in charge of those Clippy-fied versions of Office.

Another big legacy for Microsoft Bob: Melinda French, product manager for Microsoft Bob, became Mrs. Bill Gates in 1994, while development on Bob was in its final stages. Melinda's a very private person, a driving force for the Bill & Melinda Gates Foundation. Even the people who put together their wedding had to sign NDAs.

Microsoft misstep No. 11: Zune, Kin, Courier, Windows Mobile, and missing the consumer mobile boat

These days, most consumers figure that Apple created the tablet market with its first iPad. Not true: Microsoft has been nipping around the fringes of the tablet market for years. You may not know that Apple had an earlier failure -- a portable of sorts, if not a tablet. In 1989, Apple revealed its first portable computer: a 4-inch-thick, 16-pound behemoth dubbed "Macintosh Portable." The lead-acid batteries had to stay in the machine because it wouldn't run directly on AC power. And it cost only $6,500.

After the luggable MacBrick and the Sony Walkman, but before the iPad, came Apple's iPod, and that's where Microsoft's Zune enters the picture. Apple scored big successes with the iPod in 2002 and 2003. Microsoft started designing the Zune -- portable player, Windows software, music service to compete with the iPod and iTunes -- around the same time. By the time Zune came to market in 2006, Apple already had the iPhone under development. The iPhone ultimately rolled over the iPod, the Zune, and just about every piece of portable consumer electronics ever made. After years of sales that hovered near zero, Microsoft officially killed the Zune in June 2012, with the Zune services side morphing into Xbox Music and Xbox Video -- two products best known to Windows consumers for sporting their own tiles on the Windows 8 Metro Start screen.

Microsoft didn't just miss the boat with Zune. It watched and waved and heckled as the boat roared past. In 2007, Steve Ballmer told USA Today, "Now we'll get a chance to go through this again in phones and music players. There's no chance that the iPhone is going to get any significant market share. No chance. It's a $500 subsidized item. They may make a lot of money. But if you actually take a look at the 1.3 billion phones that get sold, I'd prefer to have our software in 60 percent or 70 percent or 80 percent of them, than I would to have 2 percent or 3 percent, which is what Apple might get."

Of course, Apple's income from the iPhone currently exceeds Microsoft's income -- from all sources.

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