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The Undead OS: Why Windows Vista Still Haunts Microsoft

What's that you say? Microsoft is doing all right for itself, and as a Microsoft partner, so are you. Satya Nadella is a visionary CEO who is leading the company in the right direction. In fact, Microsoft made the Fortune 25 last year for the first time ever. (I'm sure you all have your Fortune 500 parties ready for later this spring. Can Walmart repeat? Will Apple fall? The suspense is gripping.) Is all of that right?

Actually, it is. (Well, hopefully it is in the case of partners doing all right for themselves. We're cheering for you.) Microsoft is on the up overall, and that's good for pretty much anybody who is reading these words right now. But as the former editor of this newsletter (and now a writer seeking assignments -- hit me up!), I can't help but wonder what might have been had Microsoft been able to shake a certain obsession about a decade ago.

Not long ago, a report revealed that Android has passed Windows as the operating system most frequently used to access the Internet. This comes as no surprise to most of you, who are probably reading this on your phones. And while Windows will continue to be a profitable and important product for Microsoft, as it has been for decades, we go back, as most of you do, to the days when Windows was the be-all and end-all of the software industry, the "Win" in the old "Wintel" juggernaut that crushed the rest of the market under the heel of its Eddie Bauer boot.

A decade ago, Microsoft released a version of Windows called Vista, and just this week, the Seattle titan ended its life, withdrawing support for it for good from the 14 unfortunate souls who were still using it. If you weren't there, and even if you were, it's hard to fathom just how much hype Vista got in the mid-aughts. Microsoft took forever to release it. Bill Gates basically had the whole company focused on it. People named their children after it. Somebody in Sweden, if we remember correctly, recorded a dirty-mouthed (honestly, why?) song about the tortured excitement of waiting for it, but since an extremely cursory Google search didn't turn that song up, we're not going to post a link to it here.

Of course, Vista turned out to be one of Microsoft's biggest disasters (not unlike my old blog photo) -- and even Gates, for whom Vista was basically Willie Mays-with-the-Mets moment -- essentially admitted as much. RCP back then had a field day making fun of Vista before the OS landed in the dustbin of history. But if you think the Vista debacle doesn't still haunt Microsoft, think again. First, there was this, a surprisingly prescient paragraph from a 2006 blog entry:

"But while software as a service (or SAAS, as it's much easier to write) might still be a gangly teenager in terms of development, it's growing all the time. And by the time Vista and Office 2007 reach retirement age -- think five years or more from now -- SAAS should be a full-grown adult. By then, will we care about local compute power in our PCs and other devices, or will we just need a connection and a browser to user whatever apps we need with whatever functionality we require? And is Microsoft -- or anybody else -- prepared to serve its partners and customers in that world?"

The answer turned out to be...sort of. Office 365 is absolutely whipping Google's (sorry, Alphabet's) G Suite in the enterprise and pretty much everywhere else. So, score that one for Microsoft in a big way. And credit where it's due -- Office 365 started out as a G Suite (Google Apps back then) chaser and has ended up a champion. Well done, Redmond and Redmond channel partners.

But let's take a look at some other key markets. In the cloud-platform space, Amazon Web Services is the dominant leader; note that in the chart on this page, Microsoft, Google and IBM are all lumped in together in terms of market share behind AWS. Now, let's see...when did AWS make its debut? That's right, 2006. And what was Microsoft obsessed with in 2006? Windows, and specifically Vista.

There's more, of course. Apple kicked off the smartphone revolution with the 2007 release of the iPhone. What had Microsoft been working on feverishly in the run-up to that date? That's right: Vista. And when Google decided to join the smartphone fray in 2008 with the Android OS, what was Microsoft desperately trying to do? Fix Vista, or at least get Windows 7 out as quickly as possible. These days, Windows Mobile (if it's even still called that) is in a heated battle with "other" in the basement of the mobile OS market share rankings.

Back in the '90s, Bill Gates darn near missed the Internet and had to use the dominant Windows platform to provide a big assist to get Internet Explorer over the top of Netscape. (Now, of course, there is no more Internet Explorer, but that's another topic altogether.) In the mid-2000s, though, when Microsoft missed both cloud computing and mobile because it couldn't get its head out of Windows, there was no dominant platform there to save its market share. Windows was irrelevant in both spaces. Still is. So, focusing on Vista so heavily in the 2000s not only produced a garbage OS, it also turned Microsoft from a leader into a chaser in the technology industry.

In mobile in particular, some of Microsoft's attempts to catch its rivals were hilarious. There was, of course, the Zune, Microsoft's answer to the iPod, which wasn't a bad product but was characteristically uncool and a sad pretender to Apple's throne. The iPod re-launched Apple. The Zune made Microsoft a laughing stock. (Oh, and then there was search, and Bing, and aQuantive, and "we're going to make a quarter of our revenues through advertising"...but there's too much there to get back into now.)

And when it came to phones, the humiliations were arguably worse. T-Mobile seemed to deeply regret its involvement with something called the Sidekick. (Did you have one? Neither did I. Nobody did.) Then there was my personal favorite Microsoft failure, the Kin!

Not only did it sound like something from a Beverly Hillbillies script, it actually tried to take consumers back down market just as they were snapping up smartphones as if they were free pancakes. (Seriously, would you rather walk around with the sum total of all human knowledge in your pocket or carry a phone that barely texts? Who signed off on this one?)

Microsoft spent a pretty hefty amount of money advertising the Kin, a phone that did almost nothing, offering commercials that featured, as memory serves, a guy breaking up with his girlfriend...or something. Tone-deaf isn't the right expression. There wasn't even any music playing. Microsoft couldn't make the Kin go away fast enough. We intend to make live forever, at least on the domain.

We could, of course, also dig back into the Courier (What? Oh, it ended up being called the Surface), the tragic Nokia saga with Stephen Elop sent north as the harbinger of doom, or the bizarre tales of Ray Ozzie and Kevin Turner during their times in Redmond. 

But for those still soldiering through this entry, let's go back to the very beginning. Yes, Microsoft is doing great. It might not be the world's biggest brand anymore, but it's plenty powerful enough to drive profits to its partners. And it's headed in the right direction with Nadella in charge and America's least successful billionaire, Steve Ballmer, off annoying NBA players somewhere.

Still, though, let's think for a second about what could have been. Microsoft used to have a stranglehold on the entire software industry and much of the enterprise in general. Now, Amazon and Google arguably hold the power in the corporate space. What if Microsoft had stopped focusing on its Vista buggy whip -- which didn't even turn out to be a good buggy whip -- and moved much earlier toward mobile computing and developing a cloud platform? The truth is that the Surface is a good product and Azure is an excellent platform. Even Windows Mobile wasn't bad -- it was just stillborn and beset with bizarre marketing decisions.

Microsoft could have been more powerful than perhaps any other company since Standard Oil...but it isn't. And although the future looks very bright in Redmond, one of the big reasons Microsoft isn't quite what it used to be is an operating system that died this week, but which could still haunt Microsoft for years to come.

Posted by Lee Pender on April 11, 2017