Lots of great insight. Thank you for sharing!

Your comment about being too early is on point, though I'm not entirely sure it's a bad thing. If you're a big company with scale and cash to support it, exploring new frontiers is probably worth it - you either stumble upon the next big thing, or you at least get to stake your flag through some patents, and in the process - make it so if this things does grow - you already have some kernel you can build upon to start that up without having to pay up for an acquisition...

It's not perfect, but from a risk / reward perspective - I can see how this strategy could serve a large tech company well over decades...

Apple’s done extremely well by timing it perfectly, not by being too early. Never mind early or spot on, it’s been pretty late for a lot of stuff, compared to Android.

I still remember my only windows phone. Horrible thing. Had a Start menu and a stylus FFS.

The timing is often waiting for the right design as well as technology. Sometimes it could have been done sooner, if a better design had only been thought of earlier. The modern bicycle is an example, WinCE/phone is the penny-farthing.

After a decade at MS I have come to believe that there is such a thing as a first mover disadvantage. Being too early to market is just as bad as being late. Basically a new venture at a high tech company gets a lot of enthusiasm and funding, but it if doesn't succeed within some time frame, not only does it get abandoned, but the company in general won't try again for quite some time. Something else that can happen is the early v1 product gets a bad reputation, making it hard for a better v2 to gain traction.

This actually hurt Windows Phone sales. Windows Mobile 5/6 (and Pocket PC before) were miserable consumer products[1]. Sales agents in cellphone stores learned not to sell phones from Microsoft, because their device sales bonus would get clawed back when the device was returned. (Manufacturers give $$ to sales staff for each phone sold from that manufacturer, or at least that is how the market worked back when I was last in it, info is circa 2010!

When Windows Phone came out, 2 bad things happened.

1. Sales staff wasn't being offered bonuses for selling Windows Phones 2. When everyone realized how big of a disaster that move was, bonuses started being offered, but staff had been burned by 7-8 years of horrible return rates on prior Microsoft smart phones, everyone knew iPhones didn't get returned, so sales staff pushed iPhones.

oops!

Microsoft Sync is another one. Microsoft tried to make Android Auto back in 2007! Holy shit. Just think about that. In 2007 MP3 playback was still an extra add on in many models. AUX ports were an add on! No one had smart phones! It was crazy ahead of its time. And cars just weren't designed to be "smart" yet. Heck I am pretty sure in 2007 you could still find a few cars that didn't have power windows.

Oh I also used something that looked a lot like docker containers back at Microsoft. It was chained and nested VHD partitions that you could update the OS and Apps separately by just dropping in and relinking the VHDs, so the apps and dependencies were one self contained virtual hard drive image, to upgrade the apps just run some magic commands and the existing OS image had a new app image attached to it.

Microsoft had a working, reportedly playable at reasonable speed (never saw it myself) XBox 360 emulator for PC around, I think maybe 2008 or 2009?

To be clear, that is an insane technological accomplishment, to have it running at playable speeds on PCs of the time.

I got despondent working at Microsoft because I saw so much cool technology just fall by the wayside, or get mismanaged, or get a v1 launched early and then have no one believe in the v2.

Amazon Astro, their semi-autonomous robot, yeah MS tried to do that in 2012 or so. Failed because the tech wasn't ready yet (and for many other reasons!)

Microsoft tried to do eBooks back in 2000. Oops, way too early.

[1] Windows Mobile pre WP 7 was never meant to be a consumer product. Working on it I was told very bluntly that the target audience was corporate, and specifically corporate IT departments who were doing the purchasing. Pre-iPhone Microsoft even had a nice little report from some research firm saying consumers would never pay for a cellphone, they would only, en mass, get cell phones for free from their provider in return for the 2 year contract lock in. This was myopic as fuck. As a new college hire I felt like banging my head against the wall every single day for the horrible business decisions that I saw being made, and this was before the iPhone was announced!

An example of this closed mindset: When I first started at work I got my company Windows Mobile device, and shortly thereafter I went out shopping for a new TV. I was at the store wondering which one to get when I realized I could pull out my phone and do research right there. I literally stopped in my tracks and realized that having the internet in my pocket was going to be a huge societal shift. When I told my coworkers what had happened, even the next youngest member on the team dismissed what I said as being inconsequential.

Year later, same co-worker was proudly showing off the barcode scanning app on his iPhone that let him comparison shop in stores...

> "Working on it I was told very bluntly that the target audience was corporate, and specifically corporate IT departments who were doing the purchasing. ... This was myopic as fuck."

Yeah, no, that's just pretending hindsight is insight. Mobile and Embedded Devices had just successfully battled Palm and everyone else to becoming the leading smartphone OS with Windows Mobile 5.0, with 100+ devices on the market by the time WM 6.0 rolled around. Smartphones cost as much as they do today, except in pre-2005 dollars (ouch) and mobile data rates were low and crazy expensive up at that time because the mobile operators were milking the business market. It was not at all clear that a market for consumer smartphones could be jumpstarted under those conditions.

Apple's attempt to make a consumer smartphone was a huge gamble (anybody remember the Apple Newton?), admittedly helped by the considerable RDF^H^H^Hbrand leverage and design expertise they'd built up since. It wasn't at all clear that they had any momentum until the iPhone 3 came out with its money-printing app store.

> "Microsoft Sync"

Lay that at the feet of Nadella's takeover; that was a failure of strategic insight. Termination of the Windows Automotive division in the 2014 layoffs came as a complete surprise to everyone since the most recent releases had had very high consumer satisfaction ratings.

> Yeah, no, that's just pretending hindsight is insight.

Not improving basic UX of a product because an organization has a bias that "end users don't matter" is always a mistake. (Even Confluence has gotten their act together in recent years!)

Yes WM was on track to overtake Blackberry through a lower cost structure, but the phone's UX itself wasn't good.[1]

At one point I asked why we weren't including a good onscreen keyboard and I was told that we were leaving the keyboard as something OEMs could differentiate on. (Tbf I was told later that wasn't 100% true, but no one ever did explain why we didn't try to ship a good keyboard!)

> Apple's attempt to make a consumer smartphone was a huge gamble

One that Google also realized at the same time needed to be made.

> until the iPhone 3 came out with its money-printing app store.

Microsoft had an app store for Windows Mobile that they cancelled at the last minute. The source code for it was laying around when I joined. Granted it apparently wasn't the all in one app store Apple had, but not realizing people would even be willing to buy apps was myopic. (I was told it was one person's decision to kill it...)

[1] as a power user I actually loved the Windows Mobile 7 beta devices that had a keyboard and a medium sized screen, but they were already part of a bygone era by the time we got ahold of them.

I really find it sad that people try to kill ideas like this, irrespective of their intent and motivation, though I'd also like to understand these at some point. At HP, I once suggested charging customers for features they'd like to see in a future product, credited back when they buy the machine - this was to help product discovery as every customer had 'ideas' but it was hard to tell which ones mattered. It did not go over well. Now, you see this practically everywhere - from people paying to reserve F150 Lightning, Cybertruck, etc. to things such as Kickstarter.

I remember using some of those early Windows Mobile gadgets. They were pretty nice and decently capable compared to the rest of the mobile device market at the time. Problems included:

1. UI was stylus-only resistive touchscreen and basically ordinary Windows with a little duct tape to not be too awful on small screens. Still far from good though, and the styluses were clunky and easy to lose.

2. IIRC virtually no custom software and what there was was tough to install, and probably tough to develop too.

3. Web tech just not ready yet for a quality mobile web, not to mention the quality of cellular data and WiFi.

Apple took the market because they were the first to realize and really go all-in on needing finger touch screens and the absolute requirement to make every single part of the UI great to use with fingers. And also hit the market at just the right time for mobile web and cellular data to be just coming into its prime.

Fortunately for Android, they were only a little behind and got the idea on finger-first UIs once Apple showed the way.

Resistive screens have sub-pixel accuracy. First gen capacitative screens recommended UI elements be at least 1cm in size!

Microsoft's bread and butter has been productivity apps for so long, with dense UIs, that I honestly think designing for touch screens just collectively made people's heads explode.

Of course the answer is you don't need all of Excel on a mobile device all the time, but it took Microsoft literally decades to accept this.

Windows Mobile actually had some cool software, and this was back when everyone knew Win32 programming, but iphone had that sweet sweet app store and I'd guess that within a few years the number of ObjC developers grew to be larger than the number of Win32 developers, despite Win32 having almost a multi-decade head start!

> "Problems included ... resistive touchscreen "

Just as an aside, it should be remembered that capacitive touchscreen tech was primitive back then and the more precise resistive touchscreens were preferred to make best use of the tiny screens then available. IIRC, the early iPhones had to have their UI designed to work around the lower accuracy of its touchscreen. On the flipside, it must be said the multi-touch capability that gave it pinch to zoom/rotate really did help with usability.

> "...probably tough to develop too"

Depends on what one considers "tough". Windows CE had most of the Win32 APIs that desktop Windows had, so development was very similar.

Heart rate detection?

They bought webtv, didn't they? Similarly, Microsoft was not only too early on tablet computing, but also never quite got it right.

> They bought webtv, didn't they? Similarly, Microsoft was not only too early on tablet computing, but also never quite got it right.

They bought Webtv and also made Windows XP Home Theater Edition. Lots of technologies get purchased then improved upon by large tech companies, including OS X and Android!

Regarding tablets, one can argue that IPad Pro is slowly becoming what Tablet PC was back in 2003.

IMHO my 2003 Tablet PC experience was amazing. Everyone back then thought I was insane for having a laptop with "only" a 13" screen (17 and even 21 inch laptops were popular back then), but my laptop had an "incredible" 3-4 hour battery life! Heck my tablet had directional mics, I could specify from what direction I wanted audio recording focus on, it was amazing for recording lectures. I haven't seen that tech in a consumer product since. :(

Microsoft not being able to realize they could ship more than one successful OS has hurt them many times. Windows has to be everywhere. Apple got it right by forking the OS and realizing if people wanted to give them money for iOS based devices, let the cash roll in.

MS is better about accepting people's money now days. :) See Azure and Linux hosting.

I was using the tablet computers when they first came out (2003?) and I remain a fan to this day - all of my subsequent laptop purchases have consisted of models with a Wacom stylus and the ability to take notes with a pen. While the Transmeta-based model that was my first purchase was less than perfect, the subsequent models were amazing. All of my class notes from that era are still in some Windows Journal file or on OneNote.