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To be fair, the Zune actually was a better media player than the ipod in almost every way. That wasn't a false statement.

The issue was the abysmal marketing and "me too" attitude Microsoft had (and still has).

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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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Actually, Microsoft came with "modern" smart phone much sooner. Actually too soon, technology wasn't there (price, computing power, size, weight, battery life).

Apple never came first ... but often just at the right moment and had marketing skills to make it a new trend.

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> technology wasn’t there

Until Apple developed it. Those early iPhones employed a lot of tricks to squeeze usability, battery life, and performance out of underpowered devices.

Prior smartphone attempts mostly applied PC-centric concepts to the device, it’s no surprise they ended up failing.

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Microsoft never had a chance because Apple is the last vertical computer company (OS plus hardware) a survivor from the 1980s when there were many vertical American computer companies. Even Apple would have been dead if Steve Jobs had not come back with the Next operating system.

You can see the failure of Microsoft in their performance in mobile when the playing field was level Microsoft and Intel have trouble competing, you can also see it in the Surface computer efforts Microsoft has no clue.

It’s too bad SGI, Sun, Digital, Amiga, Acorn didn’t make it because you can see many elements within Apple OS from that bygone era in the hardware and software.

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BlackBerry didn’t seem to port too many PC-centric concepts. Felt like a step too far in the opposite direction actually, too PDA-ish.
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Also, capacitative/multitouch touchscreens were ridiculously expensive until Apple made orders at a scale large enough to bring the technology costs down.
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I'm the opposite of an Apple fanboy (typing this on a Windows box), but this is some grade A nonsense.

Sure, MS launched PDAs and phone-ish devices long ago, running Windows CE and whatnot but they were awful. It's absolute bollocks that the iPhone was a splashing success because of Apple marketing. It was a splashing success because it worked spectacularly well. Random non-tech people would randomly pull out their newest purchase to show their friends. "And now it's a notepad!" "Look and now suddenly it's a calculator!" Sure, your awful HP Tablet had all that, and a call function, well before. But it sucked. It felt like using a computer while squinting, and not like a magic calculator that can turn into a notepad and then into a phone and then into an iPod.

The iPhone was a success because it worked so well. And it worked so well because the technology was there - in part because they invented it and in part because they had the taste to not bring out a shit product but wait a bit instead.

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Having used a variety of pre-iPhone WinCE, Palm, Psion, etc PDAs, going purely by bullet points specs, the best WinMo devices launched in 2007 were capable and even feature-rich, but I agree the overall user experience was hobbled. Large touch-screen devices integrating phone, data and media needed a different UX and OS. MSFT's business was too platform-centric to take the strategic risk and their mindset was too incremental to make the conceptual leap.

I was at the 2007 iPhone announcement, got hands-on a prototype in the booth and had a dev unit pre-ship. As a technology strategist for a F500 ISV, my job was to assess the changing mobile device landscape. With the iPhone I think Apple deserves significant credit for two big things: the conceptual leap to a new UX/OS and going all-in on the large touch screen. Completely sacrificing both a physical keyboard or pen was bold and controversial.

While it was the right long-term vision, the reality which often gets glossed over, is the iPhone 1 didn't deliver on the vision and early adopters struggled. It wasn't until the iPhone 3G shipped 18 months later and the app store was released that the iPhone first began to slowly fulfill it's promise. I didn't daily drive an iPhone until the 3G. In recent years, I think many look back with rose-colored glasses at the iPhone launch and give Apple even more expansive credit for the "iPhone breakthrough" than the legitimate credit they justly deserve. Of the major players at the time, Apple was the only one who could make those bold choices because they didn't have existing phone products or platform agendas to preserve.

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Apple understood software/hardware and how to marry the two together (in a way that the general public wanted to use) if it was easy, Microsoft or someone in the Linux world with hardware would be further long but they’re not.

Combining hardware and software the OS was done by many companies in the 1980s because if you wanted to sell something you had to do both and it’s been well over 36 years no one has really stepped up.

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This shorthand that marketing means a bad thing is actually not true for Apple. Apple's marketing is how it ought to be at every company. They do market research to figure out what users need, they famously came up with the iPod's click wheel, they don't just do the ads. Of course Apple is eminently critiquable, but its marketing division is what everybody should do.
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Reading with understanding is absent in your skillset.

I exactly wrote that Microsoft devices were quite bad as they came too soon. And Apple came at the right moment, when low power chips were powerful enough, touchscreens were precise enough without a pen. And device had acceptable consumption, batteries had decent capacity, lifespan.

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> I exactly wrote that Microsoft devices were quite bad as they came too soon. And Apple came at the right moment, when low power chips were powerful enough, touchscreens were precise enough without a pen. And device had acceptable consumption, batteries had decent capacity, lifespan.

The argument is heavily reductionist because it treats technical breakthroughs as passive market timing rather than active, high-risk engineering.

Apple did not succeed by waiting for silicon to become fast enough to brute-force a desktop UI into a handheld. Instead, they reimagined the hardware-software stack from the ground up specifically around human fingertips and GPU acceleration.

Apple incorporated a GPU to accelerate the graphics. Apple acquired Fingerworks in 2005 and built custom chips to make multitouch viable. When Blackberry engineers were in disbelief about battery life, they cracked open an iPhone and found the battery occupied nearly the entire case. Apple also invested in aggressive thermal and power co-design such as power-gating states, dynamic clocks, ambient light sensors, etc.

It's because Apple was vertically oriented, they were able to make the necessary hardware advances.

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It’s easy to forget what a difference multitouch capacitive touchscreens made to mobile devices. As far as I’m aware, the iPhone was the first device to use it at scale. Apple also spent years designing a new interaction paradigm for it, taking multitouch from cool tech demo (Fingerworks) to the mainstream.

Microsoft had Windows Mobile and WinCE for years before iOS, but typically they got the UI wrong and tried to jam a desktop interface on a mobile OS (a few years later they overcompensated and jammed a tablet interface on a desktop OS). By the time the iPhone was out it was too late to rework Mobile into a multitouch OS.

Famously, the BlackBerry guys thought it was impossible to put a full desktop os on a phone, and that Apple must have faked the initial demo. Again, by the time they could respond by ditching their existing software and buying QNX it was too late for them too.

Android only survived because it was a new OS and the team immediately ditched their Blackberry clone UI and built an iOS clone instead. Even then it took until at least v5 before it was as smooth as iOS, and the tablet story is still poor.

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Mr. Schmidt helped out enormously… :)
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The Kin was pretty cool. Very usable with cheap hardware and cheap data plans. If the timing was a bit different, Microsoft might not have been tempted to commit infanticide.
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From what I remember, they bought Danger which had a popular product that worked, but some VP made them rewrite all their software on a Microsoft stack. This took years and didn’t work very well. By the time they were finally released they were woefully outdated and only on the market for a few weeks before being killed.
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Imagine having to go to Start - Programs - Phone, in order to make a call.
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Sure, I can imagine it. But I had a Windows Mobile phone and definitely didn't need to do this, there was a Phone button on the start screen.
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Windows CE (1996) was garbage compared to Palm OS (also 1996.)
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Years after the first iPhone release, Microsoft had a dogshit mobile OS, and every single device using it was dogshit. Before Android, the industry's answer to iOS and iPhone was a resistive touch screen and stylus because, other than the launcher, absolutely nothing was adapted to fingers. That was if you were lucky; some didn't include a stylus, reducing usefulness for making calls. It was like running regular Windows applications scaled down to a smartphone screen.
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>Apple never came first ... but often just at the right moment and had marketing skills to make it a new trend.

Newton.

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Simon Sinek - Apple vs Microsoft: https://m.youtube.com/watch?v=jEOftmUJ6a4

But it had nothing to do with the iPod/iPhone release in his story.

(story starts ~1:15, but I highly recommend the entire talk)

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Might want to edit, as this would make sense/be amusing if the exec in the last sentence was Apple.

That, or I can’t read.

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You got it, thank you!
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Hell hath no fury like Apple Global Security scorned...
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Zune was probably a better player. It was too late, and arrived when MS didn't much care.

There are emails unearthed in various lawsuits where you can read Bill Gates screaming at his subordinates: "why the hell can't our partners like Sony and Creative create a similar device? Give them all, give them early access to everything, work with them". In the end MS felt compelled to make their own.

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Sony can't be bothered to compete with Apple in that era. They were trying to recover from their DRM dreams, and their devices were already sounding great with in-house software and hardware.

Creative's Muvo^2 already was the poor man's iPod with surprisingly good audio quality as well.

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I feel like this completely misses the mark. Audio quality was never the compelling feature of the iPod and people weren't clamoring for it because it sounded good.

When the iPod came out you largely had two options for carrying your music collection on the go. You either carried a binder of CDs, or you had some niche player like Mini-Disc or an MP3 player. Both alternatives were expensive and had limitations similar to a CD in terms of number of tracks you could carry.

I had an MP3 player on either side of 2000 that was slightly smaller than a deck of playing cards that could use Smart Media flash memory cards. The largest card at the time was either 16 or 32mb and was enough to hold 1 album at near CD quality.

Creative's Muvo was a weird form factor that was larger than an iPod. It had a horrid interface both on device and for loading music. It's only grace was that it was slightly cheaper than an iPod and didn't need a Mac with FireWire. Although iircc this was pre USB 2.0 so not having FireWire would mean loading music took forever and a day.

The iPod allowed you to carry most, if not all, of your music collection in a package slightly larger than a deck of playing cards. And it had a fantastic interface for navigating music on the device.

This was at a time before most people had laptops and if you had a PC it was at home and used sparingly. The iPod was such a compelling mobile computing device that it drove adoption of the iMac. Apple would eventually release iTunes for Windows and USB support but that was many years later.

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> I had an MP3 player on either side of 2000 that was slightly smaller than a deck of playing cards that could use Smart Media flash memory cards. The largest card at the time was either 16 or 32mb and was enough to hold 1 album at near CD quality.

I had something similar. The storage was the iPod's killer feature, along with iTune's $0.99 songs. Suddenly you no longer had to buy whole albums, and you didn't have to swap out what was on your MP3 player every day when you wanted a different playlist. A 5GB hard drive in your pocket was a huge innovation then.

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"1000 songs in your pocket" was the entire driving force behind the thing. It was constantly bellowed in the marketing and it's what Steve Jobs demanded of the engineering team from day one. The size and the storage were paramount and they knew no one else could match it.
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The iPod’s user interface was good once you figured it out. I bought a 2nd gen one, I think, because it was the only large capacity device that supported audible audiobooks, and the UI frustrated the heck out of me. I consistently had trouble navigating it.

Then it clicked, the control, no matter what it looked like, it wasn’t a d-pad. It was a weird touchpad emulating a physical dial. Which exactly nothing in the documentation that it came with mentioned.

I worked for Microsoft at the time, and took a lot of grief for not using a Zune. Except I owned one, bought cheaply at the company store. It just never supported Audible.

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I'm having a hard time imagining the click wheel took you more than 10 seconds to figure out.
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I had a Rio Volt which somewhat bridged the gap. 700MB mp3 CD/RWs (about 10 hours of music per disc) and a CD player when traveling and picking up new music. Not as small as an iPod, but no book of CDs was necessary, either.
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Yep this was really it. The amount of storage on the ipod was amazing and just opened up the idea that "yes you put your full music collection on it".
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> I feel like this completely misses the mark. Audio quality was never the compelling feature of the iPod and people weren't clamoring for it because it sounded good.

Indeed. Apple made (and showed) the actual reasoning in the iPod introduction. All competitors had to was do the same: https://youtu.be/bz1ZWvZBGYM?is=NFlmkhq1gWfcNVgv

- 1000 songs

- play all popular formats: mp3, wav, aiff

- Firewire for fast transfers. Download 1000 songs at 30x speed than USB

- 10 hours continuous playback on single rechargeable battery

- the size of a card deck

Not like it was magical unknown hardware components at the time. And the competition still couldn't do it for almost a decade

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> And the competition still couldn't do it for almost a decade

There were a couple things Apple had in their favor but it certainly didn't take 10 years for folks to catch up. They mostly one because they captured people's hearts and minds.

The key things Apple did right was a high speed connection and owning their software. The Creative Nomad Jukebox used the same HDD as the iPod and beat Apple to market by a year, but Creative didn't own the software. The iRiver H series of players showed up around 2004 and were comparable to iPods in terms of quality and capability, though their aesthetic wasn't polished minimalism. Their UI wasn't as good but it was still very good. Their crux was Windows and Mac support wasn't great. I had an iRiver in 2007 and was running an opensource (rockbox?) firmware to get around some of those issues.

Apple has always been good at innovating around the problem which is usually the UI or software at large. This comes in part because of their vertical integration and being able to make minor tweaks to other parts of the ecosystem (e.g. desktop OS) to dramatically improve the experience of their product. The iPods are another great example where they made minor tweaks to iOS Bluetooth that magically made the experience of using wireless headphones dramatically better.

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Yeah I had an iriver. That thing was great because it essentially acted as a giant (for the time) USB drive. And it could play any mp3s and you put on it.

You synced music by manually managing folders on the device. All my non technical friends were horrified by it. They didn’t have neatly organised mp3 libraries. For all of iTunes’ problems, being able to plug in a cable and hit the big “Sync” button was really simple and convenient.

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I clean forgot a about iRiver :)
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> Zune was probably a better player.

In some ways, anyway. Never owned a Zune myself, but a university classmate did and I was shocked by how poorly it handled non-Latin languages… she had a ton of Japanese and Korean songs loaded onto it, and their metadata all displayed as "missing character" blocks. She used it a lot like one might use an iPod Shuffle despite it having a nice screen because the only way to tell what was playing was by hearing it play.

By contrast my 4th gen B&W iPod which was about 5-6 years older handled unicode just fine.

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IIRC the Zune had a much better DAC on the device than any ipod. I own two of them and the sound quality was always notably great.
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It let you squirt over a song to your friend

https://youtu.be/ud6rwVkbovA

And they could listen to it 3 times in 3 days

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“Squirting” was ridiculed at the time and the word itself scaring away women. Jobs killed it then in an interview with a classic quote: Microsoft = Cold tech and Apple = Humanity. MS scares her away, Apple gets the girl.

> QUESTION: Microsoft has announced its new iPod competitor, Zune. It says that this device is all about building communities. Are you worried?

> Steve Jobs: In a word, no. I’ve seen the demonstrations on the Internet about how you can find another person using a Zune and give them a song they can play three times. It takes forever. By the time you’ve gone through all that, the girl’s got up and left! You’re much better off to take one of your earbuds out and put it in her ear. Then you’re connected with about two feet of headphone cable.

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I loved the book The Infinite Game. Really changed how I looked at work, personal research, and being an author. Recommended!
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That just sounds like a standard introvert response when one doesn’t want to walk.
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The anecdote is likely a false rip of the actual story:

[2017] Speaking at an event Tuesday, Scott Forstall, who lead Apple's iOS software division under Jobs, recounted the surprising history behind the company's first touchscreen prototype, which ultimately lead to the first iPhone.

It all began, Forstall said, because Jobs had an acquaintance at Microsoft who he really, really, didn't like.

"It began because Steve hated this guy at Microsoft," Forstall said during the event. "Any time Steve had any interaction with the guy, he'd come back pissed off."

The unnamed Microsoft exec, who was apparently the husband of a friend of Jobs' wife, apparently bragged so much it pushed Jobs over the edge.

"He just shoved it in Steve's face -- the way they were going to rule the world with their new tablets with their pens. He came in on Monday with a set of expletives and then was like 'let's show them how it's really done.' "

https://mashable.com/article/scott-forstall-steve-jobs-micro...

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Spite cam actually be one of the most powerful motivators for productivity, in my own experience. I can buy this story being accurate.
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In Steve's case "fueled by spite" would be more precisely "borderline personality disorder". If you read him in that lens it might help distinguish how to be successful like him without all of the bad parts.
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