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I recall reading this story of some user doing a sync with Zune on their new computer. The computer had no songs on it and the Zune synced with that machine and wiped all the existing music off his Zune without warning him(or something like that its been years). I recall thinking, yep thats Microsoft. And to this day I still encounter dumb ways of thinking in many of their products. The endless negative stories I hear about Windows 11 are just the tip of the iceberg. The entire company has to be following a cohesive vision with leadership at top needing to be truly involved to make great end to end products and really Microsoft has not been that in a long time.
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I was a zune user. I had my music organised meticulously and could simply drag and drop to my zune from my (parents) windows desktop. It was simple and it was fantastic.

Then I got a iPod so I needed to download iTunes. I downloaded iTunes, it told me to import my music. I imported my meticulously organised collection. It duplicated every single file into the iTunes approved format (AAC?) - my meticulous collection was now less meticulous, messy even.

It caused me to swear off Apple products for decades. Though it also led me to some very basic programming in order to delete the duplicates. I was only partially successful.

Programming led me to use Linux, before I eventually moved over to Mac. I like to think this was their plan all along.

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Can’t reply to jsondb, but iTunes had a default option to convert to AAC afaik.
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iTunes for Windows was indeed awful.
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As a hobbyist teen I built my own itunes clone for PC from scratch and remember getting so excited when Apple posted a job for someone to port iTunes officially.

I remember getting so excited, then depressed when I realised a hobbyist teenager could never compete with the people Apple would have applying. Later seeing how bizarrely bloated iTunes for PC turned out, guess I probably could have.

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iTunes for Mac was also awful. I don’t know where the idea comes from that iTunes on Mac was good software but I remember reading that and getting a my first (then Intel) Mac and wondering why it got so much praise on Mac. It was the same software with slightly better UI but generally the same awful UX (except for drivers and performance which was never an issue on Win for me)
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Because back in the dawn of OS X it was legitimately a good music utility
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I don’t think that happened. At least not as you’re telling it. iTunes never required AAC files.
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I believe that, (possibly only) in the early days, it offered to add any imported music to your library, which I think it indeed did by converting to AAC and putting in a directory structure of its choosing.
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It probably could convert to AAC, but the biggest issue for collector nerds with carefully curated collections of mp3's organized in folders by artist and album and with perfect metadata was that iTunes would take all your hard work, shake it around, rename all the files and dump them in a single folder and fuck up your metadata. At least that's how I remember it, but it's over 20 years ago ...
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I think the core lesson of the story is knowing if your hobby is listening to music or curating a music collection. Optimize for one or the other.

I went from meticulously curated MP3 collection on Linux to letting iTunes do it for me, and I realized that the meticulous curation and hunting down album art and everything was a hobby I didn't actually love. But if you do love it, great! Different tools for different jobs.

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I remember the trick was to use a network hard disk or drive for the music. iTunes kept the organized folders and all files untouched while building its metadata-only archive in local. But in general, yes, the tendency to mess with your file was built-in.
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I'm sure there are other examples, but you picked one here that is very unfair.

> their new computer. The computer had no songs on it and the Zune synced with that machine and wiped all the existing music

This is identical to the default way the iPod worked. If you bought a new Mac, and needed to get your music onto it, you had to use the migration assistant (connect via ethernet or firewire) or copy the music yourself. If you just plugged in your iPod to the new 'empty' mac and hit Sync, you'd lose your music too.

This was done as a show of good faith to the RIAA - their nightmare was that users would go from one dorm room to the next, dumping all their music onto all their friends' PCs. As a result, an iPod (or indeed still an iPhone today) can only sync with one music library (aka one computer) at a time. If you put it in "manually manage" mode, you can copy onto the iPod/iPhone from a 'foreign' library, but you can still never copy in the other direction. And all of this is true even when your music has no DRM encryption.

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I remember Microsoft introduced a DRM / certification program they called "Playsforsure".

Two years later they introduce the Zune, which could not play "Playsforsure" music people had purchased from MSN..

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Heh, sounds like Windows Phone. Release Windows Phone 7, get early adopters and traction. Thank the early adopters by releasing Windows Phone 8, which is incompatible with existing Windows Phone 7 devices. Also make it use a new app development SDK so that Windows Phone 8 apps don't work on Windows Phone 7 (modulo some weird transition tech that almost nobody uses).
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The funny thing was they could have done the adaptation--instead of doing it they just presumed devs would transition.

They were also done with the android-apps-on-windowsphone project but dumped it because PC marketplace managers got mad at it because then devs wouldn't use their sdk. Luckily we still got the first version of WSL because of that project's partnership with that linux team.

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One of the many reasons I moved away from ipods is because iTunes (which was awful; some of the worst software I've used) did the same thing to me just before I went on a trip.

I thought to myself: "I better add these two new albums to my ipod so that I can listen to them while away". I plug in the ipod, itunes loads up, I walk away. I come back 10 minutes later and it had not finished yet and I wonder what is going on. Turns out it deleted my entire 40gb library off my ipod and started re-syncing. I had to leave so I unplugged the ipod but it was basically useless at that point.

I do agree with Microsoft in general but Apple seems to be very much the same in my experience.

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iTunes was great in the beginning. If you can, find someone with a G3/G4 and OSX 10.4/10.5 and see just how snappy that thing feels even with a 100th the RAM of today and a spinning disk. A real nice piece of software.

But then they just started dumping everything onto it and it eventually crumbled under the weight.

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To be fair, I had that experience with my first iPod. As soon as I got it, I synced it with my computer and loaded up a ton of songs on it. This took a while.

Some time later, I connected it to my dad's computer to put a couple more songs on it. The first thing it did when I hit "sync" was delete everything on the iPod.

I learned that day that "sync" meant something different to Apple than it did to me.

I'm sure it gave me some kind of prompt but it was not a clear "hey this is going to delete everything" prompt.

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to be honest, apple did this when it launched apple music.

It did all kinds of things like hiding your music library, merging your music with apple's music, all kinds of nonsense.

You used to be able to put your music on your phone easily, then it became sort of a gauntlet in favor of apple's subscription service.

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I did the same when I tried to copy a friends music from his iPod to my iTunes library. Wiped his iPod instead. I think we have a tie there...
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To be fair, iTunes suffered from the same defect at one point. Microsoft is now a clinic on defective design, execution, and attitude. But back then it wasn't that bad.

The iTunes case was also a classis UI 101 blunder combined with stupidity. If there was no iPod plugged in, the "Sync on connection" toggle in iTunes simply disappeared. First of all, when something is inapplicable, you grey it out. You don't just make it disappear.

But in this case, even greying it out would have committed the same blunder, because the default state for this behavior was YES.

So if the hard drive in your computer went bad and you installed the OS fresh on a new one, thinking that all your music was backed up on your iPod, you were right... until you plugged it in.

So, so dumb.

And finally: Apple never addressed the lack of "computer overwrites mobile" and "mobile overwrites computer," which Palm OS syncing nailed in the '90s.

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This weeks fun example of 'What will Windows 11 do today?' is that it suddenly wants to max out the Ethernet adapter with nothing. No packets are actually going anywhere but it just ends up hogging the entire data bus until you restart it once or twice.

This is the kind of nonsense we have been putting up with for years.

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Oh, you mean like MacOS (OSX) installer deleting whole hard drives if there was a space in the volume name? It's so funny how fan boys can selectively ignore the bugs by their favorite company
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Exactly. The same for Windows Phone. Both was amazing software on great hardware. They just never gained enough traction because MS was a bit late to the party and wasn't willing to push through (e.g. by compensating the late start and poor market position with heavy marketing investments and partnerships), so they eventually trashed those projects.

It's such a shame that the shitty MS products survive the ages while the great ones never gain real traction. I feel a bit sorry for the people who built such amazing stuff just to see it being cancelled and then having to work on the unsolicited background execution of the SharePoint 365 rev4.7 update manager (I made this up, but it probably exists).

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Google broke YouTube for Windows Phone.

Not just the app, but also the browser.

Also, in my experience the Windows Phone hardware was dodgy. The first one I bought was a Dell and failed under warranty…and the replacement failed out of warranty. Then after an LG Android, I bought one of the last Lumia’s. The camera failed just out of warranty. Then the whole thing failed while I was traveling.

So I bought an iPhone.

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I had a great run with the Lumia range devices but I could see it vary wildly depending on designer/manufacturers.

I end up on Android simply because of file drag and drop and an open App ecosystem which they are now trying to lock down.

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Yes, the death of Windows phone was a tragedy for the mobile phone market; it had a fresh take on things, and could have stirred up healthy competition with the duopoly of iPhones and Android phones.

I never could understand why MS would not put heavy muscle behind it. Maybe they deep down knew hardware execution was not their strong suit. People think the software was the problem, but I think if MS really believed in the product, the software side was eminently solvable.

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At the time when they killed Windows Phone they had a $7 billion write off and that was huge. A decade or so later they would buy Activision for $69 billion without blinking. I would happy swap those in an instant.

It felt like once they dropped mobile, their whole direction become misguided. Also UWP made sense when there was also a mobile/tablet side to it, could even deploy those apps to the Xbox and it kind of worked. But then they kicked out that supporting support and suddenly they got working on trashing what good Windows still had.

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The iPod's click wheel was amazing. Grab one if you have the chance and play a bit with it. I imagine a lot of people don't remember or have never used. Such a great feel and UX, Apple at its best.

iTunes was also unrivaled in its first versions, before it became an everything app. And syncing was pretty great before ubiquitous internet was a thing.

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I owned one for a very long time. I know people loved the clicky clack, but that thing was a UX abomination. The only thing it was good for was high speed jogging - not something that you typically do very often on a music player.

"Apple at its best" ... I sure hope not. But for sure, people LOVED that wheel. I would take a 4-way clicky from the Zune any day.

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> …high speed jogging - not something that you typically do very often on a music player.

That’s exactly what you often do on them, when they are good at it. How would you rather browse a large library: one by one, slowly, or use a non-linear accelerator to quickly get close to where you want to be and then precisely pick your choice?

The click wheel was brilliant software and hardware, simultaneously, which is why I call it “Apple at its best”.

It could have been good software with unreliable, wobbly hardware, or robust hardware with a slight rendering delay, which would break the illusion. Instead it was sturdy, responsive and just a joy to use. Much like Apple’s trackpads, which remain surprisingly unmatched.

But I guess we have different tastes on music players.

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I think it was an example of a well executed idea taken war too far, like the touchscreens on a Tesla replacing essential physical buttons. Or the obsession with getting rid of buttons on the iPhone (which we’re now thankfully retreating from).

It did have its sweet spot - jogging to an exact spot in a song, or scrolling a long list. But you do a lot more than just that on a music player. And the overall experience of the iPod was actually somewhat sub par because of the overuse of that one feature.

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From what I recall Zune had a much bigger screen for videos so I bought one for that reason you can see the side by side here:

https://electronics.howstuffworks.com/zune-ipod.htm

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I had to hunt this, but the classic design perspective of the ipod vs zune by Joel

https://youtu.be/e-blUcmpW1s?list=PLcIkt5s7w8D0ywp0CBmNFWRTF...

At the end of the day Apple got design and Microsoft didn't and it showed in their sales.

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Technical capability pales in comparison to human desire.
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Being easy and pleasant to use and own is also an important capacity.
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Until you actually need to run a business. Then money is much more important than the preferences of your employees. That's why Apple has barely penetrated the business world beyond overfunded startups that are more driven by hype and design wanna-bes than actual profit.
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Microsoft fumbled the Windows ball so hard, everybody i know got rid of their Windows PC and either went to Android/iPhone or got a Mac or Linux.

At work we can freely choose which OS we run on our machines. Guess what everybody wants since IT got forced to upgrade each laptop to Windows 11? Macbook Pro.

I personally am running Linux just because I already know how to use it but macOS (despite its flaws) is way less intrusive and much faster than Windows. Even Microsoft's own programs (Office 365, Teams) are running faster and have better UX on macOS than on Windows.

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10% of Microsoft's revenue is Windows. Azure is closer to 40%. Their focus has shifted hard from software to services. Azure is making them around $100B and growing. It'd be far more surprising if they were putting their focus back to Windows in a saturated market given all the incentives they have to chase bigger revenue elsewhere.
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And Linux is the premier OS on Azure. I'll never stop getting a kick out of Azure Linux.

https://github.com/microsoft/azurelinux

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Yeah, but there's no reason to go Azure unless you are really tied to the MS Windows ecosystem.

If there's choice, everyone goes with Linux servers.

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We chose Azure for our startup because of data location, and it was cheaper than the other two as well. Data center locations may not matter much in the US (because everyone has this covered well), but it does in other places of the world.
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Can't reply to @shorel, but of course Azure is running Linux servers. It has nothing to do with being tied to a Windows ecosystem.

Your choice to go with Azure probably has more to do with where you're getting value for cloud services, and where you started your project - in other words, how tied you are to the Azure ecosystem, or the AWS ecosystem as the case may be.

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Most devs choosing Macbooks has a lot to do with culture. It's boutique, cool, and all the other successful people have it. Yes, officially it's always for technical reasons, but no one would ever admit to get something just because it's shiny.
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Hmm, you are saying that devs have preferred a POSIX system over whatever Windows 11 is, because it's "boutique"?
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Not OP, but I absolutely know people like this. Devs who don't even know what POSIX is, let alone care whether their OS is compliant.
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Yes, exactly.
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I chose a MacBook as my laptop last job because my Nvidia drivers kept breaking on my Linux laptop
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One can argue they made much more money selling to people than business. Business forces you to compete on price and that drives everything down to 0. The market clearly values selling to people more than selling to business: look at their stock price. So if you are actually running a computer company wouldn't it be better if you took Apple's approach (if you could)?
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> Until you actually need to run a business. Did you mean to say "Until you actually need to sell to a business."? They did do very well for a long time mostly by focusing on consumers...
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Macs have a smaller marketshare for Business than Windows machines, but iPhones are ubiquitous in enterprise.
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I feel like businesses could spend way less (money-wise and time-wise) on technical support if they just gave out MacBook Airs to their employees which could then remote into virtual Windows desktops for whatever legacy software they need to use.

Why should 90% of people need to deal with BIOS updates, driver updates, daily operating system updates, and blue screens of death?

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The point is that after the iPhone dropped it didn't matter.
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You’re right but that is not the point. The point t is that soon after the whole category of portable MP3 players got wiped out by smart phones.
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Never had a zune, but I did have an iPod. I am willing to accept Zune was superior. But its just an example that, yea, often times the superior solution doesn't actually win. There is a huge list of better technology that lost out to worst technology. Which is why I find it funny the claim that the market is optimal in choosing winners and loosers.
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The market is optimal, you're failing to value brand perception and any social effects as a price factor

Androids are probably better than iPhones. But you may lose a first date with a girl for sending a message with green bubbles instead of blue bubbles, so people buy iPhones. The iPhone is worth more than the Android, in this example.

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> But you may lose a first date with a girl for sending a message with green bubbles instead of blue bubbles, so people buy iPhones.

What.the.actual.fuck. Can you expand on this? I have so many questions.

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I was being a little exaggeratory on the 'first date' specifically, but there is 100% a subculture of 'normies' who care about things like that. The iPhone, and even the amount of cameras on your iPhone, became a status symbol.

Apple knows it, it's why they do everything they can to prevent 3rd party 'workarounds' to use iMessage. It's one of the things that gets people in the ecosystem, and keeps people in the ecosystem once they're in.

Blue bubbles and Facetime has probably kept more customers than anything else they have

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I haven't heard of people losing a first date, but I remember a few years ago seeing articles about teens being excluded from group chats if they were using an Android because it was considered something you'd only buy if you couldn't afford an iphone. Android and iphone also didn't share the same features for texting, so people didn't want Android users in their chat because it meant they couldn't use all the imessage features.
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I’ve met people like this. “Oh, green bubbles - I don’t know what I expected” / “I didn’t realise he was poor”. It’s 100% a thing for some people.
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People have preferences. Some preferences are shallow. That's it, really. All kinds of people exist in this world, and wanting to be perceived as high-status is practically quintessential human behaviour.
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I had the first iPod, and later the first Zune. The Zune had a beautiful UI, but by then Apple came out with the iPod Nano 2nd gen and that took the cake.
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It was better in every way you can quantify in a tech specs listing, and not in any way that actually matters to the customer.
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I had the OG white Zune. It was the same price as an iPod ~$250. The reason I chose Zune was the Zune Pass. A precursor to Spotify. Plus growing up in the Seattle area, I knew other people who had them and we would trade songs.
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I completely forgot you could "squirt" songs to other Zune owners. What a time!

(Brown launch model here.)

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100% - the iPod wasn't just good enough, it was more than enough for almost everyone. The Zune was firmly in the diminishing returns category by the time it came out.
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Yep. To overcome an incumbent that sells a very good product and has momentum, it is almost never enough to be somewhat better. You have to be "knock my socks off" better.

The Zune may have been somewhat better (until the nano and iphone), but it wasn't enough better to overcome the ecosystem switching costs.

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Not much difference between storing as many songs you can listen to in a lifetime, or storing twice as many songs as you can listen to in a lifetime.
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me still thinking about the iRiver H320 I was lusting after...
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My Zune 30's still kicking! Ipods aren't.
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Apple excels in marketing. They are more similar to Nintendo than Nvidia.
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And the Zune media player was a much better media player than the other 6 Microsoft media players. It was crazy how much Microsoft invested in cannibalizing its own products--I remember they had a similar number of word processors, email clients, etc.
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And marketing it with "turd brown" ass (oops!) an option
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> the abysmal marketing

WELCOME TO THE SOCIAL

I remember multiple tech reviewers praising the marketing at the time. It was the first time my younger and more naive self experienced that now-familiar feeling in relation to the tech industry: "am I taking crazy pills? have I slipped into the bizarro universe? have these people ever interacted with another human being?" etc

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The Zune failed vs the iPod because of marketing? Okay.
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The turd brown color certainly didn't help
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For you maybe. I love the color of my turds.
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shut your mouth - that brown was beautiful.
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I'm with you. It was brown, and if I remember right, in the light the edges had a sort of greenish tint to them? I thought it looked so cool, hadn't seen anything like it before.
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The color definitely made me want to shut my mouth
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That combined with naming the sharing feature "squirting".
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2006 was the year Nintendo showed us how to play with our Wiis, while Microsoft asked us to squirt at THE SOCIAL.
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They failed because of design.
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