Apparently, someone is paying attention.

A couple of weeks ago I wrote a post about how it’s a RIM BlackBerry and Apple iPhone country. Within a day or so I received an email from a PR woman representing Enterprise Mobile, a company formed in partnership with Microsoft to handle enterprise sales of Windows Mobile. I proclaimed Windows Mobile an also ran here in the States. They thought otherwise.

So here’s the U.S. market share from Q4 of 2007 provided by Canalys:
– RIM BlackBerry: 41%
– iPhone: 28%
– Windows Mobile: 21%
– All Others: 10%

(As an aside, I chose fourth quarter instead of 2007 annual numbers since iPhone wasn’t released until Q3. This way the numbers would be comparable.)

So the question I asked Mort Rosenthal, CEO of Enterprise Mobile, is after 11 years of developing a mobile operating system and being outpaced in half a year by iPhone, why can Microsoft succeed now? I wanted to know: was there a change in emphasis at Microsoft? Was the Windows Mobile OS becoming more important? Were RIM and Apple making big mistakes that, in his eyes, was going to change the market?

His responses: First, he discounts Apple in the enterprise as it is a consumer device that doesn’t have the level of security and IT support (beyond Exchange with OS 2.0) required.

Second, his conversations with IT professionals is that RIM does one thing really well — it does email. Windows Mobile is more strategic, meaning it does a wealth of things really well for the actual workers in the field.

Okay, those are good answers. I believe the first, not so much the second.

So I asked why, if Microsoft considers Windows Mobile so strategic, would it in essence outsource its enterprise sales, even one with a respected leader like Enterprise Mobile? Mort’s response: the deals are too small to interest Microsoft’s enterprise sales teams. Microsoft doesn’t want those deals to get lost in the shuffle.

While Mort had some good points and led me to believe that (maybe) this fight for the enterprise isn’t as over as I think, I didn’t exactly see Microsoft catching up to RIM any time soon either. After all, if the deals are so small that Microsoft sales team can’t focus on them, then how strategic can the business actually be? Based on my estimates, Windows Mobile accounted for a whopping 1.5% of Microsoft’s entire revenue!

I’ve believed for a long time that Microsoft developed a mobile OS as a place holder. When the market took off, Microsoft thought they would use their overall market position to steal sales. But while Microsoft was turning out relatively minor changes from Pocket PC 2000 through Windows Mobile 6, RIM jumped ahead of them. Way ahead.

Add to this threats in almost every aspect of Microsoft’s business and I’m having a hard time buying that Windows Mobile is going to be the winner — enterprise or otherwise. I just don’t see how the company focuses on 1.5% of their revenue when at least 70% of their revenue and MS’ computer dominance is being attacked by the likes of Apple, Google, Adobe, Nintendo, and Yahoo!, all at the same time.

Besides, I’ve talked to BlackBerry enterprise users, too. And all I ever hear is, “You can have my BlackBerry when you pry it from my cold, dead hands.”

All I heard for a while was predictions for the death of the BlackBerry. And then everyone around me said you can’t get third-party apps for the iPhone. When you can, then the BlackBerry will be dead. Then the iPhone SDK was announced and the death watch of the BlackBerry started again.

Personally, I don’t see it for two main reasons. Here’s why:

1. IT Departments. At big companies across the country, IT departments love the BlackBerry. RIM’s secret sauce, as I learned last year at the BlackBerry Wireless Enterprise Symposium, is not so much the device but instead its ultra-cool server software that lets IT professionals control those pesky little devices. BlackBerry Enterprise Server doesn’t just control the interchange with Microsoft Exchange and other email systems. In addition, it gives the IT department complete control over those devices. There are hundreds of pre-canned permissions and the ability to generate more.

In the enterprise, RIM is the leader — Apple is playing catch-up — so RIM doesn’t have to develop ultra-cool, innovative devices. All market leaders have to do is generally keep up with the joneses and they will keep the market. And that’s what RIM continues to do, its latest being the BlackBerry Bold just announced last week. Improved layout, check. Improved browsing, check. Wifi, check. A handful of other things people have been dying for, check. Good enough to keep Apple off our rears in the enterprise, check.

2. Email. The second reason is a usability issue. I have not used an iPhone but I have used an iPod Touch. The browser and interface are top-notch, way above and beyond what anyone else has done. But where the device falls short is when it comes to typing anything. It’s horrible. So the market splits: are you an email and texting and calendar and tasks person? Or are you a browsing and music and YouTube person? If you fall into the former, like me, then BlackBerry does it since I am primarily email and secondarily browsing. If you prefer gaming and entertainment, the latter is for you.

So in my mind, BlackBerry isn’t dead in the consumer market, either. It all comes down to taste. But what is clear — and to me has been for the past year — is that it is a two-horse race. The likes of Microsoft’s Windows Mobile, Palm’s operating system and Symbian — at least here in the States as it is dominant in Europe — are also rans.

Over the weekend, Fred Wilson wrote on his blog about the music industry and the future of streaming music. An important quote:

Over the next five years, the number of places and devices where you can’t get a speedy wireless connection is going to dwindle to maybe the car.

Ah, to dream! For 10 years we have talked about this day in mobile computing. Some will dread a world where we are always connected. But I see a world of possibilities.

This is the world my generation is waiting for and a world my two kids will understand innately.

Interesting products and services at your fingertips all the time on any computing device.

Software companies can bring them to you less expensively because we can write it for the web and gain huge cost efficiencies to deliver it.

Advancements in learning and teaching and growing that will match our individual lifestyles.

And, of course, an off switch when you want to be left alone.