And that's why anecdotal evidence can never be used to prove anything.
Speaking of Jay Leno, I've been watching Colbert, who is an avid Apple user, yet he wears his Watch perhaps one week out of two months worth of shows. The rest of the time it's Swiss time pieces.
So we'll have to agree to disagree about the round watch. I don't see any reason why it's a bad idea. I do see why they chose to go with square first, since it would be an easier way for developers to get their feet wet in an unfamiliar operating system, and I have no argument that it is the best format for displaying text. However, Jony Ive is also on record saying the watch is best used for glances, and for anything more substantial the user should pull out an iPhone. So truly, text presentation shouldn't even be a major consideration with such a device, with glanceable information displayed in a circle just as effectively as a square.
As for choice, we'll just have to see. They bent over backwards to hire some very influential fashion people to work on the watch, and pulled some major publicity events giving away a custom $25,000 Edition to Karl Lagerfeld, among other influential luminaries in the fashion world. So I have a hard time imagining they will get away with updating the case materials and watch bands a couple of times a year without criticism from an industry Apple seems desperate to have in their corner. Fashion is very particular to people. There's one woman I met who would have liked to buy an Apple watch, but she only wears gold jewelry and accessories. Since she couldn't afford the Edition, she passed on buying one. I haven't seen her since the gold Sport became available but I am curious whether that solved her problem, though Apple lost out on some money as she would have happily paid up to $2,000 for one. Also, what happens when a woman wears an outfit with a round theme (yes it happens)? Hoop earrings, bracelets, round belt buckle, circular patterns in the clothing ... and a square watch? While that may or may not sound trivial to you, it's a palpable problem for those who see such needs in their personal fashion. So it all depends on how serious Apple is taking their new role within the fashion industry. Maybe it was all lip service to launch the watch, and now after getting the initial blessing of the high fashion world, they will just go their own way and rest on their laurels, cranking out the same square design year after year, dressed up with seasonal colors.
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Here's a slightly better example:
Developers will go wherever the money goes. Apple has just enabled pairing of multiple watches to the iPhone, which means the same customer who bought a square watch could also buy a round watch to increase their wearable options, therefore effectively doubling their investment into Watches. Developers who don't accommodate round watches will go unused on them, to their own detriment.
Also, you're making the assumption that this is such a difficult problem for developers. For starters, Apple will do the heavy lifting, incorporating many aspects of the round UI into the OS, and the rest will be dictated by Apple's guidelines. And who cares if some apps don't fully utilize the round UI? As long as the basic Apple apps do.