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tl;dr:

Ex. micro-softie laments all the ways ms failed in the mobile space, while completely overlooking the elephant in the room:

MS, in the mobile space, did not have an already entrenched monopoly upon which to leverage other market share.

Is this a fair analysis, though? It's not like Apple or Samsung had monopolies that they leveraged to their advantage to drive mobile share.

Unless this is a subtle commentary on Google's use of their search monopolistic power to drive adoption of Android (which drives further adoption of Google products) -- if so, then kudos to you.

Other than the XBox, what new thing has Microsoft launched that has not hinged on its existing dominance?

It seems that the people that brought Microsoft to where it became the dominant force either left or were no longer listened to and Microsoft simply expected to succeed because they where already huge 'over there.'

> It seems that the people that brought Microsoft to where it became the dominant force either left or were no longer listened to and Microsoft simply expected to succeed because they where already huge 'over there.'

May be these people have no more disruptive ideas.

> It's not like Apple or Samsung had monopolies that they leveraged to their advantage to drive mobile share.

The iPhone was a natural progression from the iPod, which dominated the music player market since the turn of the millenium.

I don't buy that. If the iPhone was 'just an improved iPod' at release, reception wouldn't have been as mixed as it was ('brilliant' vs 'flop')

The iPhone was a small battery powered box you can hold in your hand and it could play music, just like the iPod, but at the time the iPhone debuted, that's about where the similarities ended.

Also, because of its price ($500 plus a two-year contract) the iPhone targeted a different audience.

Looking back at the keynote where Steve Jobs announced the iPhone, the progression from the iPod served as huge leverage and represented one of the core three components of the phones marketing strategy.

The iPhone was about combining your music player (that everybody already owned) and with your phone and then adding an incredibly smooth web experience. Without the iPod functionality, it would have still been a revolutionary phone, but the mass adoption and hype surrounding it would have been reduced.

> The iPhone was a small battery powered box you can hold in your hand and it could play music, just like the iPod, but at the time the iPhone debuted, that's about where the similarities ended.

iPods had just become colour when the iPhone came out, so the main differences were interaction (touchscreen vs "touch wheel"), screen size and connectivity. It wasn't long before the iPod touch came out, with a big touchscreen and apps; basically a non-phone iPhone, giving that different audience a clear transition path.

The point isn't whether Apple or Samsung had monopolies. They didn't need them. The point is that Microsoft didn't have monopoly leverage, and they did need it.

Why did Microsoft need monopoly leverage? Because for about 20 years, that had been the way they won in new markets: they entered the new market, found a way to leverage the Windows monopoly to give them an edge in that market, and went on to win a dominant position in the new market.

So when the time came to try to dominate a new market without that edge from leveraging Windows, Microsoft didn't know how to do it.

Microsoft is a software development company in much the same way that the Corleone family was in the olive oil importation business.
Clarification: I mean to say that they have done well, but it's not just because they're really good at importing olive oil.
>MS, in the mobile space, did not have an already entrenched monopoly upon which to leverage other market share.

Not quite true. MS managed to beat out Palm to become the market leader in PDAs and mobile devices, just before the iPhone was released and torpedoed everyone.

At one time, there were as many different models of Windows CE devices as there are Android devices now, giving MS a severe fragmentation problem back then similar to the one that Android has now.

Corporate smart phones, sure.

Consumer smart phones are a very different prospect.

Way to have a typo before the article even begins.
I thought it was a typo as well, but author continues to write 'loose' in place of 'lose' so maybe English isn't his native language.
I started writing Android programs in 2011. With Android:

   * I can develop the apps on Windows, Mac or Linux
   * There is a lifetime developer fee of $25
   * The source code is available
To program for the Windows phone, I believe I'd need a Windows setup which I don't have. "A small barrier" some might say, but a barrier nonetheless. I believe the Windows Store fee was $100 a year or something like that. Not much for a seeded company looking to build apps, but it might discourage a student looking to release an app.

For all the hassles of Android's ever-changing API and such, they do try to make it painless for developers to get onboarded.

This is true, but Apple has the same model - you need an OS/X machine (note: much more expensive than a basic windows machine) to develop for iOS, and I believe the app store fee is also $100. It doesn't seem to have hampered iOS at all. (although the argument to be made is that because they were the first to get big, the barrier to entry didn't matter much).
I would say the $100 fee even helped the iOS app store. It sets the floor so that I as a user knows that this app most likely isn't spam. And you need an OSX machine because it's compiled and signed by XCode. I know a few developers that held out because of the Xcode requirement (cough, VLC) but eventually even they realised Apple had no reason to change and either the foundation was going to release or someone else.
True — but it's also why neither I nor the companies I've worked at have worked on iOS apps (of note, the Android apps we've built have been internal corporate apps, not consumer-facing apps, where iOS's consumer base would be an asset).

I as a developer very much don't want to use Windows or macOS. Why would I want to use either of them when I can use Linux? I know there are others who think otherwise; it's great that we all live in a world where we can direct our destinies.

This makes no sense. In what kind of backwards company are internal apps targeted based on the software devs' platform preferences? The determining factor is what phones the people who need to use the apps have. If many of the people that need to use the app have iPhones, you'd be forced to write them for iPhones. If many had Windows Phones, you'd be forced to write them for Windows Phones. Your development-platform preferences be damned.
The hoops of developing for iOS were why the company didn't develop internal apps for iOS; the hoops of developing for iOS are also why I don't develop for iOS.

I am not a slave; I can choose where I work.

To be fair, for iOS development, you need a Mac and it is closed source as well. One would argue that Microsoft is closer to Apple than it is to Google.

And Android is not a 100% open source stack, parts of it are closed source.

Apple had the same hoops to jump through as MS.
iOS has the same issues, though, except you need an Apple machine, which is usually WAY more expensive than a comparable Windows machine (not sure how well needing to pay for VisualStudio closes that gap).

I doubt this was a factor at all for Microsoft's success or failure, frankly.

EDIT: Apparently I type slow. I'll leave this here anyway.

I think the article is a nice summary of why Microsoft lost, but it doesn't fulfill the promise of its title. "Should have won" implies that there were steps Microsoft should have taken to overcome the difficulties it faced. Let's explore some:

Lack of vendor trust, not wanting to get locked in with Microsoft like PC-makers did. No easy solution there.

Hampered by success of cash-cows like Windows/Office. Shouldn't Microsoft have been focusing on its strengths? Hindsight is 20/20, but those strengths are still doing well for Microsoft. Who's to say throwing more resources at Windows Phone would have gotten a better result?

Even difficulties that seem like they had obvious solutions, such as lack of mobile web, may have been very hard to do, technologically, pre-2008, with smaller screens and lack of mobile bandwith.

The article points out that Windows Phone never got above 15% share. Why was it entitled to win? Or, to rephrase, why should it have won?

They had just the same opportunity to do mobile web as Apple - CE devices could run a real browser. Unfortunately, that browser was IE.

I think Apple's real innovation was the App Store, combined with a usable (non-resistive) touchscreen. Prior to the App Store, it was remarkably hard to get apps onto phones. You were dependent on the mobile carrier, whose levels of customer gouging made Microsoft look like newbies. And they were usually terrible when you did start them, so few bothered.

The other problem was that the CE UI was not adapted for mobile; its look and feel was the same as the desktop. Too many tiny click targets. "Metro" was the attempt to fix this (too late). Apple also brought in the pinch-zoom gesture system and dynamic rotation.

> Apple's real innovation was the App Store

The app store only launched in July 2008, same time when iPhone 3G launched.

It was more than 1 year after the original iPhone launch.

The original iPhone was a marketing success even being merely a feature phone by today’s standards: no app store and no user-installable apps at all.

> other problem was that the CE UI was not adapted for mobile

HTC launched its first touch-oriented windows mobile phone almost 1 month before the first iPhone. They called it HTC Touch and included custom touch-optimized WinCE shell. Nobody cared, and people just bought iPhones instead, the sales figures for that year was 2M devices HTC, 6M Apple.

Because better and touch optimized browser, and also because unlimited data plan. Back in 2007-2008, you couldn’t buy unlimited mobile data for any other phone.

> The other problem was that the CE UI was not adapted for mobile

I had the AT&T flip-phone pictured in the article and it is my favorite phone ever. The CE shell and bundled apps for non-touch devices were extremely well adapted to the constraints. The one thing I remember well is that I could open it up, punch in 666, and besides showing dialing that as a number it would bring up a list of matching contacts to select from. 666 == MOM. I've never held another smartphone which did that.

Microsoft lost because their successful platform was a fantastic phone with so-so data features and the iPhone flipped the game around.

Microsoft had a path it could have taken. Write an android launcher that looks like Windows Phone Tiles. Get people to "convert their phones to Windows phones"

Release an Android App Store. Release .netCore as part of your app store, so to run these type of apps, they need your app store instead of normal android apps running on Dalvik/AndroidRuntime.

Fork android, like Kindle, and release a copy with Skype for messaging, outlook for mail, the rest of office, the Microsoft Store.

Now they have Windows Phones, that run natively on all android hardware, and have backwards compatibility with android apps.

They completely skipped the embrace extend steps, and tried to jump right to extinguish.

They lost because their ultimate strategy was "All Roads Lead to Windows." This is what handcuffed all their talented developers and product managers into creating extremely inferior products. The ones that had freedom from the Windows ecosystem, like X-Box, did relatively well in terms of competitiveness.

Steve Ballmer was stuck in his dinosaur thinking and couldn't see the writing on the wall. The break away from the Windows monopoly is one smart thing Nadella did, and hopefully it frees up all these talented developers from creating better products.

Microsoft hasn't really given up "All Roads Lead to Windows." They are pushing very hard in the VR/AR space for Windows to be the prime OS, partnering with Oculus, creating HoloLens, adding Windows Universal App support for AR devices. And XBox no longer has the independence it once had -- it must also run a standard offering of Windows.
If that's true, they're just going to get screwed in exactly the same way iPhone screwed them. Mobile VR is going to be substantially more popular than VR-plugged-into-a-giant-expensive-Windows-box. The subset of people who want to maintain a PC is dwindling. New-to-computing users basically go straight to mobile. Untethered VR is better for social (no cords to tangle, we each control our own device), and that's not even talking about what's going to happen when AR hits. AR tied to a PC makes zero sense outside of industrial uses.

Microsoft better have a dedicated VR-centered mobile skunkworks going, or they're just going to repeat this entire "Two Windows' In One!" fiasco all over again. Except now it's going to be three Windows'.

You know Apple does. They're going to come out swinging hard with dedicated VR hardware, a dedicated VR OS and I suspect dedicated VR silicon too. With some kind of VR Facetime, VR iMovie, and partnerships with some major iOS app makers. Samsung is already shipping. Microsoft is already struggling not to slip into 4th place, in terms of profit. And Valve is, for the first time, in a position to offer a complete Microsoft-free platform of their own. While Microsoft is trying to compete with Apple at their new game, Valve is gunning hard to out-Microsoft Microsoft at their old game (an open PC platform).

> Steve Ballmer was stuck in his dinosaur thinking and couldn't see the writing on the wall.

How can you see the writing on the wall when you're busing laughing at the competition with your eyes closed. I recall that he even laughed at Android.

Why are the charts that old? (2011, 2012) With newer charts from 2015/2016, it's clearly visible that Microsoft lost the mobile war, with less than 1% market share. Not that grim, but bad as well is the XBoxOne marketshare compared to the allmighty PS4. And the Win10 marketshare is half of what Microsoft expected one year after launch, almost another Vista - from a consumer perspective the privacy leak makes it worse than Win8 and Vista combined, but that's another story some will say - well the users aren't dumb, they choose the better alternatives every day, and Microsoft looses marketshare. Think about it.
Single major innovation in iPhone was ability to perform reasonably high precision user interaction using grossly imprecise input method, i.e. Human thumbs. My theory is that people in WinMo team didn't used iPhone when it came out because everyone carried WinMo in their pocket. I think most people just didn't believed it was perfectly possible to use touch keyboard with thumbs with reasonable precision. So the reaction to new design was slow. Once Verizon told Microsoft how they were bleeding customers over iPhone, people realized the significance of what had happened. But then there was long battle for how to evolve. Should old WinMo code be modified or do we need new OS or do we combine desktop and mobile OS? This would have been difficult decision in itself because you also need to support vast number of existing WinMo customers. This struggle took years to resolve and by that time ship was sailed. If there was one person in charge who understood what was going to hit the world and gave order to unify entire army behind creating new mobile OS without worrying about compatibility or merge with desktop then we might have had different story. Of course, in hindsight every thing looks crystal clear about what should have been done but if you were sitting in Ballmerd chair with data you had in hand your call could have been the same. On the other hand Android chief realized what was going to hit them and they turned around their execution overnight which was possible because they didn't had legacy OS used by millions or desktop OS diverging from mobile. Anyway, this is just my theory. I have no insider information like the author.
The capacitive touch screen is a major factor however I believe it was Steve Jobs ability to break carrier control (in the USA, where the iPhone was initially launched) was critical. I had worked for a while in the telecoms business and noted this at the time. In fact I bought Apple stock on the day the iPhone was announced specifically because it had a visual voicemail feature. This was something we had built years before but could not get it on phones because the carriers liked to charge for the air time to listen to and delete voice mails. He also got AT&T to provide a reasonably cheap data plan. At the time you could either have a cheap plan with services the carrier had complete control over, OR you could have IP connectivity at a much higher price. This isn't something I'm rationalizing after the fact: I saw it happen, opened the Schwab web site, bought stock and made a nice profit. I had no notion of apps or nice browsers or decent touch screens being key at the time. There were no apps on the iPhone initially but they had long existed for WM Nokia BB etc.
The data plan was insane. Year before I had a Palm and it cost $45 vs. $20 for the iPhone. Sure it was 2G, but the things you could do were so compelling.

Being on the road, starting a download for an app at one stoplight and being able to use it by the time I got to the next stop light... that was an epiphany.

"Windows windows windows windows windows windows windows windows"

This was Ballmer's response at a conference when he was asked what Microsoft's response would be to the iPhone. Verbatim.

Main reason: capacitive touchscreen display. They were last to understand how they were enablers of a new way of interacting.
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I have bought a Lumia just to play around with the WinRT platform, as was positively impressed by the SDK and Visual Studio tooling, versus the usual chaos of Android releases specially for NDK users.

The C++/CX + XAML experience feels like Visual C++ finally catching up with C++ Builder and finally becoming visual.

Also the component model allows for an easy interaction between .NET, JavaScript and C++, similar to Objective-C++ / JavaScript Core on iOS.

So I really like the WinRT model.

But alas, with all the mid-steps specially the last one of ditching the 512MB Lumias, Microsoft should just drop WP from the UWP supported platforms.

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I can see the seeds of Microsoft's failure in Ballmer's response to the iPhone question. He talks about how the device can "do email" and "do web". They were check off items. Apple didn't say "our device can do email" they said "you can get your mail wherever you are." They weren't the first to offer that by far but they talked about the customer: the end user.

Ballmer also talked about his customer: the enterprise CIOs (and for the phones, the carriers, not the end users).

Apart from the money-losing Xbox division I am not sure Microsoft really has ever had an end user orientation. Not surprisingly, given Ballmer's background, they are a 20th century industrial concern, more like a car company than anything else. That served them very well when the field was young and the companies that were computerizing needed all the help they could get -- and so were willing to be dictated to.

By the way I also liked the buffoonery of saying that they have a "respectable position" in the "high end" music player business. In another appearance he touted their strength in the "hard-disk based music player space." It reminded me of Steve Jobs claiming that NeXT was dominant in the "business workstation space". Let's define a niche and fill it...backwards!

(Ironically Zune did have a number of interesting features (dare I say "innovations") but the customer base was too smart to care about specs. By focusing on gimmicks they ignored the hard work of making a product that people actually wanted to use.

I do still miss that keyboard. I still don't type nearly as fast on a phone, and considering that these devices had no autocorrect, not nearly with a quarter of the accuracy.

Apart from the resistive touch-hostile technology and stylus-centric interface, HID has taken a substantial step backwards in the years following the decline of CE devices.