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We wrote software for Tablet PC when they first launched in the early 2000s. I was in love with the form factor. We even bundled with Viewsonic’s tablets and had a couple around the office. In 2007 or 8, after it was way too slow to run Windows, I installed Linux on it and figured out how to get pdfs and ebooks running. Worked reasonably well but was a brick of a device and the battery was going so didn’t last long.

When the iPhone launched we released a version of our software for it. We did okay but the market was a mess. Novelty apps did better than productivity apps. For iPad, I had a friend who knew a guy in developer relations at Apple and my friend recommended us. Apple was looking for products they could promote that didn’t have an iPad version already. So last minute after announcing but before launch a couple of us went to Cupertino to make sure our software ran on the devices well.

That was amazing. 14 page nondisclosure agreement then escorted us to a room with brown paper over the windows. We worked on iPads tethered to the desk and anytime we ran into trouble they called in the developer who literally wrote the code we were struggling with. Just amazing experience!

We weren’t featured in retail or on stage but did get featured in the App Store a few times, the only time that ever really happened for us, and was a finance app of the year in 2011 (I think). That was the peak of financial success on iOS for us as well. Just brutal.

While I know some made lots of money on Apple’s devices, we did significantly better on Palm and Windows Mobile in late 1990s/early 2000s, honestly. More focused products on business customers and reasonable software prices.

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There’s definitely the other side of a new ecosystem which is developing the business that becomes breakthrough. That is equally as difficult but not often discussed. The ecosystem highlights the successes and has a big voice but behind every success are many people working hard but still challenged to break through.

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Microsoft's apps group had that brown paper over the windows experience for the original Mac. My mac hac a cutout for a 360k floppy disk from before the Sony 400k drives were finalized.

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My biggest regret at this time was not realizing how quickly iPad sales grew. I assumed a more traditional slow growth curve, which in my mind gave us more time to plan and execute our response. Netbooks showed the large scope of the desire for computing at some other form factor and strongly implied there was a lot of demand. I was too enmeshed in the PC ecosystem thinking.

There are a lot of strategy angles on this: How Micrsoft's focus on writing and productivity created a blind spot and how Microsoft's poor relationships in the Independent Hardware Vendor (IHV) community (the companies that make components of PCs, like touch screens) caused a miss in understanding how well capacitive touch was working.

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How much of the poor relationships were fueled by Apple's tight control over the entire ecosystem from hardware to OS to applications vs Microsoft's open approach where anyone could "clone" a PC and Windows tried to work on all of them?

IHVs want to feel special, no?

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It had to do with the conflict of "who was in charge" and "who could bring volume." Microsoft could try to influence IHVs but without being a paying customer garnered little attention. We started to change that dynamic with the Windows planning process that involved the entire ecosystem in designing the next version of Windows and Windows PC. Think of it as having the OEMs (aka the people buying) along with us to have the conversations. There was always a potential conflict between OEMs, Intel, and Microsoft related to relative advantage for profit (that's the who's in charge part). We tried to make this much more a process of mutual cooperation.

The volume question was difficult because of OEMs dealing with the retail channel. Each retailer wanted exclusive models, which fragmented volume. Apple's model of limited combinations allowed them to show up to IHVs with huge orders and thus get the attention on software and other needs.

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I think it was almost worse than Microsoft not being a paying customer. We were being paid and yet we didn’t act like all the other suppliers.

It isn’t clear to me, however, there is any sort of different end-state to a series of partners that have to come together to deliver one product. Eventually the partnerships fragment and a competitor (or technology) arises that uplevels the whole offering changing where the seams are in the ecosystem.

The idea of being vertically constrained also has a natural end-point which Apple has seen before. First it saw it with PowerPC and how impossible it was to keep pace with Intel investing so much in Moore’s Law. It saw this again with manufacturing when Tim Cook joined and changed SJ’s view of using a manufacturing partner. Apple won’t be challenged directly by either of those end-states but there will be another way that having all its eggs in one basket will be challenged.

We faced a glimmer of hope with Ultrabooks which I will describe in a future post.

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Thanks, Jon. That makes a lot of sense.

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The Courier project strikes me as a master class in how the PUM organization world competed for mindshare and resources. If the management team didn't fund an idea, tactics like this one were used to punish or coerce management to change their minds. It was a symptom of an organization out of control. Think again of the internet meme of the Microsoft org chart.

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The use of these artificial mechanisms to coerce others were something we definitely tried to get rid of (and responded to many times in Office too—VBA.NET was one adventure like that).

This type of behavior—these bank shots so to speak—are what real corporate politics look like. It’s just awful.

I think in the next couple of sections I’m going to get into the Platform for WIndows 8 which I feel was subject to a lot of coercion. This from a different angle—not using management but using external partners in an effort to amplify a voice. Using the circularity of “without your involvement evangelism made a commitment to these parties who signed up to use this technology so now you can’t make a choice that undermines this effort” when the reality was much less about success than it was a scorecard that defined its own success.

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Looking forward to the next section, curious if your observations about how Windows 8 and ultimately Windows 10 are similar and different to Windows 3.1 and Windows 95. I have some theories that I shared at the time, wonder if they stand the test of time.

One thing I've always admired about good leadership... or maybe a better way to say it is a symptom I've noticed when there is good leadership... is the debates are about "how", not about "why". Having been on "Peak Office" and "Peak Windows" both projects were very much about all of us figuring out "how" to achieve, not "why" or even "what". So many other projects tend to devolve into debates about "why", usually as a proxy for "I have this other vision, so will debate why yours is wrong".

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It's an interesting internal dimension of vaporware as well. The 80s and 90s saw so many companies competing against each other with rumors and innuendo and few hard facts. Courier and many other projects inside Microsoft whether covert or overt (NetDocs?) were internal to Microsoft versions of this vapor-ware, win by imagination not execution.. and oddly not innovation.

It seems to be one of those unwinnable battles. If you coalesce these projects into a single focused organization, you're accused of fiefdoms. If you fund them both and see who wins, you're innovating and pitting what should be cooperation into combat and secrecy.

MikeAng once said to me "The difference between hallucination and vision is whether someone else sees it." It's interesting in the context of the big bet, big innovation swings, the bigger the bet the more likely someone doesn't see it.

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Classic Mike!

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