Microsoft Losing Against iPod, iPhone, iOS, iMessage, Slack, Dropbox
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But for the rest, I doubt MS would have succeeded in those markets even under the best of circumstances. The iPod made Apple big again, but without Steve Jobs as the pitchman, it wouldn't have had the massive impact it did. The offerings of MS (the Zune) and others (Creative, Sandisk, Toshiba, Sony, etc.) were more than good enough, and they worked with a variety of online music stores. It's just without the brand cachet of the iPod and Apple's lifestyle marketing, it's hard to get excited about an MP3 player.
Slack and Dropbox are both huge inside startups, but nonexistent in old-school enterprise companies. Nobody at work wants yet another login to have to remember. I know this because I work inside a digital team at a 3000-person company where everyone swears by O365's out of the box capabilities. Skype for Business and OneDrive for Business inside of an O365 plan is "good enough" for a lot of people.
Dropbox has made losses each year since 2015. It's great that it's achieved good market share since it started in 2007, but maybe there's a limited enterprise market for something that's a one-trick pony. And one-trick ponies are the polar opposite of MS' strategy.
You can add $1 billion for the discontinued in 48 days https://en.wikipedia.org/wiki/Microsoft_Kin Kin social networking phone, in which they also scored an own goal against their cloud offerings by trashing the database running their purchased userbase: https://en.wikipedia.org/wiki/Microsoft_data_loss_2009
The total losses, official or not, have got to run into the tens of millions.
Which was part of why the Kin was so late, they moved every Danger employee they retained who was working on the Hiptop line to the Kin, then had to pull a bunch back to finish 2 more versions. Who could have guessed that Deutsche Telekom could pose a serious threat to Microsoft?
The Zune came out in November 2006 - less than three months before the iPhone was introduced and a little bit over a year before iPod sales started declining.
Microsoft introduced a hard drive based player years after the flash based Nanos were already more popular.
Then MS released the flash based non touch screen Zunes after the iPod Touch was becoming popular.
Finally they released the touch screen Zunes after the App Store came out and the Zunes couldn’t run third party apps. Even the hard drive based iPods had a few curated third party apps by 2005.
Unlike today, where we have multiple Surface-branded products, back then Microsoft only had Xbox, which operated as an entirely separate division from Windows + Office.
Before the Zune, MS tried to be the software partner for non-iPod devices, with the Windows Media Player store and Plays4Sure DRM standard (which they botched). It's only after it all failed that they rushed into the market with the Zune, which was a partially redesigned rebrand of a Toshiba MP3 player that was in the works.
Looking back, it’s OK Microsoft lost out on a few things. There’s now a bit more balance in tech.
Going forward, Microsoft does have some exciting products that could be great. For example, the Surface and HoloLens.
Apple is dragging their feet with the iPad and AR can’t get here soon enough. Microsoft hits it big with either of those products and no one will care about not beating Dropbox or iPhone, etc.
You don't think it was Android that destroyed Windows Phone?
I guess if you want to get technical, Microsoft did.
Microsoft thought it was competing against the iPhone:
https://www.businessinsider.com/microsoft-iphone-funeral-201...
Apple had first mover advantage, so the time it took for them to catch up on features like copy/paste was negligible because "no one else" had it either, because consumers thought of it as a new category [0]. Microsoft didn't have the luxury of first mover advantage (or even second mover because Android).
Apple also had the marketing luck of hitting enough sales power early enough to control their own fate with the big US telecom carriers (AT&T especially from the start, but eventually they all played ball with Apple). Microsoft was expected by the telecoms to follow the old rules that they should have known by heart from Windows Mobile <= 6.5, not Apple's (still) very special rules, and that shouldn't have been a surprise. Android played by the old rules and decided the wild west of fragmentation issues was fine enough.
[0] (That is that they weren't feature comparing the iPhone to say Palm, Blackberry, or even Windows Mobile 6.x.)
For instance, I'd argue the point where Windows phone/mobile lost the "bottom" segment of the market (esp. in India and "emerging markets"), when the OS became too hard to run on cheap handsets of the lowest specs, to cheaper Android knockoffs was a key inflection point where the platform lost so much of its momentum.
Whether or not you feel that Microsoft buying Nokia was a cause of that or a symptom of that. It was somewhere between "both" in my mind, in that it was a symptom of software upgrades at first but snowballed because of the Nokia purchase. Certainly there were factors that the OS was maybe too quickly pushing bottom level specs. (As much maligned as the app lifecycles of Windows 8 apps were from a developer standpoint, they did help the platform hit some very low specs. Windows 10 over-correcting from developer complaints did not help mobile.) In addition to not solving the telecom carrier software update problem satisfactorily to OEM needs (as I mentioned), there's also the Android price match question of whether or not Microsoft dropped the OEM price to "free" for Windows on the mobile form factor too late to win new OEMs. (They probably were too late, but there still seemed opportunity at the time they dropped the price. Again, purchasing Nokia confuses the timing of all that and which effects were snowballing.)
Nothing is as sticky as Windows desktop and office. Show me anything that competes with that combination? Even with the advent of the smartphone, the combination of those two is still unbeatable in corporate America.
If they don't happen to get into PC gaming with Windows there are kids aged 5-10 right now that might sit down at a Windows PC for the first time in college or when they start their first job in corporate America. Things could easily follow Blackberry's path very suddenly when new workers are no longer familiar with the tools and there's cheaper, faster, and more productive alternatives that your employees would prefer using and are advocating for.
Android has only made Google $21 billion in profit in its entire history....less than Apple makes in one quarter.
https://www.google.com/search?q=android+oracle+revenue&ie=UT...
This is probably a good thing in the long run for Microsoft as some of its more innovative work has been when it's tried to focus on cross-platform software (its founding era, and the early GUI wars, for instances), but that vision of a single flexible OS across all device form factors is still an attractive one, especially from an efficiency of scale perspective.
But today MS has Xamarin that is a good enough cross platform framework for enterprise style apps.
Windows CE never had the efficiency of scale convergence quite in mind, though. Windows CE was never quite Windows at the kernel level, for instance, and it was a competing OS inside Microsoft in some ways that mattered in the old xkcd siloes pointing guns at each other fashion.
Windows 10 mobile, especially towards the end (Redstone 3) was so very similar to Desktop Windows under the hood. It was still a fork, but it was a converging fork.
(UWP still sometimes gets unfavorably compared to the .NET CF, but UWP has always been more powerful and capable than CF and CE-era C++/MFC, even at its "worst" when Windows 8 launched. Especially now that .NET Core is open source and "leading" the .NET Framework/.NET standards rather than vice versa, UWP is much stronger than .NET CF ever was.)
What is the fascination with monopolies?
I for one am happy there‘s choice
Even the early GUI era you could see Microsoft hedging bets and trying to be the best Macintosh software company while working on Windows. Even as late as the XP/Vista timeframe you could see that Microsoft was often proud of being the largest third-party software vendor for the Macintosh. (That statistic got shaken up soon after, IIRC, but Microsoft held that position for a long time.)
Cross-platform certainly isn't a new attitude for Microsoft. In some ways it seems a return "home" to when they were the BASIC provider for every computer. (Though the argument of whether or not BASIC then was an OS platform is a fascinating one, which is why both perspectives are "correct".)