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What Microsoft Needs? Years of Big, Money-Losing Bets, Consultant Says

Breakout

I never thought of it this way before, but consultant Roger Kay, founder of Endpoint Technologies, kind of sees Microsoft (MSFT) as the Vanilla Ice of the tech sector.

Microsoft, he says is basically the beneficiary of a once-a-century, one-time windfall for "having figured out a market 30 years ago." Kay adds that their future, a slow decline of their main franchise, is actually quite visible. Ouch. Clearly not the kind of talk that inspires men to great things, but nonetheless, a seemingly fair take on a behemoth that has been trading consistently within a few bucks of $25 a share since the collapse of the tech bubble in 2001.

And yet, inside the halls -- and latest earnings results -- of the giant from Redmond, Wash., there are some good things going on. Even Kay concedes it's a company with tons of cash that could pay out another mega dividend. Plus, at these levels, it's unlikely to break out or break down.

So how does Microsoft hit the lottery for the second time, Mr. Kay?

What CEO Steve Ballmer needs to do is make a series of big bets "in which they'll probably lose money for years, and which eventually can turn the corner and they can become dominant in new markets." The hope, he says would be to replicate the success of new businesses like the Xbox and Kinect -- another dozen times.

But for a company he says doesn't "quite seem to get what is really cool" and whose DNA Kay describes as being "kind of corporate," that could be tough.

An area of relative enthusiasm is Microsoft's server and tools business, which Kay says is considered young at 10 years old, has lots of upside (think cloud services) but more work to do.

It's hard to feel too bad for a $200 billion dollar company with fat margins and unthinkable market share that has spawned the richest man in the world (and hundreds of mere millionaires), but if you listen to Kay you just might find it in your heart to cut Microsoft a little slack. But probably not.

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