Bill Gates Just Confessed His Greatest Ever Mistake: He Still Hasn't Got over It
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Sure Ballmer made those silly comments that the iPhone wouldn't sell (in part he was right, they quickly dropped the price) but he was a fool for trying to stick with Windows on a phone. There had been Windows Mobile devices for many years before the iPhone and they all sucked. Trying to evolve that platform was idiotic. It was the perfect chance for Microsoft to start from scratch with a new platform but nope they decided to cut and slice away at Windows until it ran on a mobile ARM SoC and it was overall pretty shitty. They tried to put lipstick on the pig with Live Tiles and such but at the end of the day it still had all the awful decades old junk that comes with Windows.
I guess another way of phrasing Mr. Gates comment would be "My biggest regret is not giving Steve a kick in the ass to do something new rather than try and shoe horn Windows into a phone"?
Zero understand of the experience. Zero understanding of the customer. Phones and tech to him are things that you just do and check the box and move on. What a complete non-visionary.
Source: https://www.youtube.com/watch?v=W5g4sPi1wd4
He was asked a question just after 9:00 in the video about work/life balance in the early days of Microsoft and includes this in his answer around 11:40.
Android copied how iOS worked and felt fairly closely to it and it became an affordable alternative product for the non bourgeoisie.
iOS is not so intuitive that anyone can pick it up and figure out how to use it. There are still older people that don't understand it and handset interfaces could be improved if a company can stomach throwing away a few complete designs for the sake of clarity. Microsoft just didn't have the vision required to make something that had its own merit besides being the poor mans iOS. To say that handsets can never be improved and that iOS is fundamentally the best it can ever be is short sighted. Of course a new paradigm can be found that is superior. An also ran that is cheaper is running with an also ran that has been around way longer that already fills that role. So the only way to get that market is to innovate.
The main problem was a lack of focus. The developer experience was a rehash of desktop models that were reworked for mobile but not portable either, so you had something very similar and incompatible. This was not a place to be extending the desktop (Windows CE, Forms).
I find it hard to believe that MS took mobile seriously producing only the low-quality devkits and limited marketing they did. I also wouldn't count them out just yet either. iPadOS (or iTableOS?) is showing that there's a third platform yet to come and MS Surface with good dev tooling and app runtime could win over Flutter/Fuchsia.