Did Jobs make the same mistakes with iOS that he made with Mac OS in the '80s?

No. History is not repeating itself. Apple is making about 70% of the profits in the cellphone industry. With the exception of Samsung, all of the Android and Windows handset makers are losing money. This is something new. Apple dominates the profitable top-end of the market. Android dominates the bottom end.  There are certainly more handsets at the bottom, but no profits.  Samsung has spent a fortune in marketing to carve a niche for top-end Android handsets, but is finding that hard to sustain. This is not at all like the Mac / Windows years.  Nothing like it at all.  It was a clear-cut victory for the Windows platform. Even that clear-cut victory is no longer as clear cut as it was. While there are still enormous amounts of Windows machines in circulation, and the Mac represents only a few percent of sales,  the Mac now makes more money than the top 5 PC OEMs combined.

In platform plays, such as iOS, I think that the answer starts with the simple precept that he who wins the hearts and minds of developers, wins the war.  On this front, the Developer "dogs" are fully eating the Apple dog food, and coming back for seconds. Why is this so? Quite simply, Apple has orchestrated a much better overall system for developers than Google has with Android. Think about it. For developers, they have created tremendous leverage across three products families (iPod, iPhone and iPad), with a fourth in the not so distant horizon (Apple TV).  That's 130M units and counting that you can develop for with a predictable end to end -- from development and distribution to discovery and monetization.  From this platform play has arisen the Apps Lifestyle, and it is a core differentiator for Apple and consumers alike. By contrast, Android is still very much at the kids table for most developers, which is a by-product of their focus on winning the hearts and minds of carriers and handset makers over developers and consumers. Relative to the chess game that Apple is playing, I think that they are executing at an all-time great level.  I see plenty of imperfections and quibbles, to be sure, but fundamental mistakes, no.

Normally I would say yes to this, but Microsoft's open strategy is not helping them in the mobile space at all despite the number of partners they have. Perhaps there are two categories going on here, the closed system which Apple and RIM participate in and the open architecture category which consists of Android, Windows Phone 7 and arguably Symbian. The advantages to the closed system is that RIM and Apple each own the ecosystems in which they exist. They own the hardware and software aspects and respectfully make money off both, where-areas Google and Microsoft simply make money on the software side (licensing the OS and their app stores). I am not sure which is better, volume is always the goal obviously, but I will say that as a single phone manufacturer, it's extremely impressive in how much market share Apple owns. In regards to Apple's desktop OS, it's an amazing operating system, but it's served best on Apple's hardware. If Apple opened up their OS for other hardware developers, they would be years behind Microsoft in development and hardware compatibility. A closed ecosystem isn't a bad thing, console makers have been doing it for years, and that has not stopped people from buying game systems. The best thing Apple can do is make their OS compatible with Windows-based networks. The more people get a chance to play with an Apple system, the more likely they will buy one to integrate into their existing home network.

If by mistake, you mean he's doing what he has done for ages, yes, he is! But, it's not a mistake at all. The biggest reason why Apple wins today is because they control the whole stack from software to hardware and the content delivery platform. This makes for a far superior end-user experience than other manufacturers out there. Quick example: go out and find me a Verizon based Android phone without the verizon logo in the original manufacturer's store. Didn't find one? Exactly! But, with Apple, the supply chain bends to their whims. No ugly phone company logos on the iPhones, complete control of the content delivery and app store all lead to best overall experience. That's nothing new, by the way. Apple did the same thing with iPod. To figure out iPod's success, look at the commercials - it always incorporated "iPod + iTunes." There were sooo many MP3 players, but they all sucked because they didn't figure out the last mile problem. Going back to MacOS, Jobs kept it closed because he wanted developers to have an even footing for developing consistently great content without worrying about the changing specs (hint: iOS is very much the same deal). It might have been a 'mistake' as you put it back then, but now, it's a pure proven profit model for Apple. In fact, Jobs has successfully boiled down the whole process to design driven engineering with simplicity in mind (by that I mean an interface friendly enough for beginners yet powerful for experts too. A lot of these underlying themes could be found outside Apple too - look at Pixar and NeXT, both Job's creations. When in doubt about Apple's competitor's, pretend that the product is a Pixar Movie - anything else competing with that particular movie's theme will look polished but feel very second-to-the market.   Before you rebut, consider the factors from a developer centric point of view - as in it's way easier to develop for iOS than Android in sheer terms of testing on the number of devices supported and getting people to try it out physically (as in Apple stores). This luxury is not prevalent with any other manufacturer.

If we notice the reason why Apple failed to capture market like Microsoft, is simply because Apple has been always rated among the expensive cadre of products available in the market. On the other hand Microsoft brought windows which was an inexpensive and user-friendly alternative, and it captured the market. As truly said " History repeats itself " Apple has their IOS again getting hammered by the inexpensive and arguably much competitive alternative (Android). Statistics shows that among trendsetters in the market the one's that sustain are the one's that have quality, quantity and value for money. We can see the exact same scenario which Jobs faced with the Mac OS in the 80's, only difference being the fact that Mac OS now here is IOS and Microsoft Windows in this case turns out to be Android. Conclusion : Yes Jobs was making the same mistakes with iOS that he made with Mac OS in the-80s. Because in the end its the collective results of the entire genre of consumers that counts in the overall market. Not merely the "more privileged" category which Jobs targeted.

Maybe.....maybe not. Some stuff that was verboten in the past isn't so now, like privacy which used to be the holy grail of the web and now everyone it's uploading embarrassing HD pictures of themselves that will stay there close to FOREVER. Back in the 80s Apple was more or less another computer brand, and for most of the 90s you were called a loser if you happen to own one. But now brand matters, so much that the cost of brand awareness can be higher than R&D and manufacturing costs combined. You can create a product and produce it, but it will take a lot of money for people to buy it. Today that shiny apple logo on the back of every unit it's pure branding gold! And here's the big part: back in the 90s the #1 reason NOT to buy a Mac was the lack of mainstream software, still a problem if you consider games. But iOS is completely different; not only it still has more apps than Android, but the fact is that if it weren't for the appStore as the only destination for iOS apps (rather than a series of markets) most people would not even know those apps existed, so another hit for Apple. This is mostly the reason why devs are willing to put with the no-flash BS. So, my point is that Jobs might be making the same mistakes, but because the overall situation changed so much it is not that much of a problem anymore.