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.

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..

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.

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.

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.

Being easy and pleasant to use and own is also an important capacity.

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.

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.

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.

My Zune 30's still kicking! Ipods aren't.

me still thinking about the iRiver H320 I was lusting after...

The turd brown color certainly didn't help

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.

Also, capacitative/multitouch touchscreens were ridiculously expensive until Apple made orders at a scale large enough to bring the technology costs down.

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.

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.

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.

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.

Imagine having to go to Start - Programs - Phone, in order to make a call.

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.

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.

“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.