Think Like a Designer
opencal.comApple may have won on design, but what the author fails to mention is that despite all of this, Google is doing pretty darn well.
The missing ingredient on Apple's side that is allowing Google to excel is the lack of openness in attempt to control and micromanage the experience. While truly good design requires a great degree of control, people like freedom.
If you travel around the world, one thing you will notice more often than not is that cities and towns are often poorly planned. This is annoying to many of us, and we respect the cities and towns with the well planned grid layout of roads, where the roads are numbered in order, etc. So, if a more well-controlled and better designed city or town is better, why are there more cities and towns that are more loosely planned? Freedom. Things that grow organically, grow more.
This is why Apple failed against the IBM clones and Windows in the late 80s through the 90s. Apple had the chance to allow Mac clones, but didn't since they would compete with Macs, and they'd lose control.
I would think that there are more cities that are poorly planned not because of a concerted effort to allow it to grow organically, but because it's difficult to plan the expansion of entire cities, especially in the cases of those that are many centuries old.
For example, compare the streets around Wall Street (where New Amsterdam was largely first settled) with 'newer' areas North of it where it becomes slightly less tight and more gridded.