I know this is a subjective thing, but I think it could spark a good discussion on UX.
When someone rides a segway they tend to not look cool, despite the fact that they're actually pretty fun to ride around. Contrast this with hoverboards which are generally cooler looking than a segway while still maintaining the same basic function. There's also other modes of transportation like bikes, roller blades, vehicles, and running that are generally seen as being cooler than riding a segway. One can definitely look uncool while using these other modes of transportation, but it's easier to look uncool on a segway than it is with any of those.
So I guess my question boils down to this: What design decisions are a part of the segway that make it so easy to look uncool when compared to other modes of transportation?
The Segway was vulnerable from at least two fronts. On one hand you could make something that looks like a Segway but has four wheels and provides the same experience without the technology. Alternately there are all the devices that are similar but much smaller, simpler and cheaper. For that matter there are electric bikes and other things that don't self-balance but are good options to get around. (I was looking at an e-bike the other day that uses structural batteries and other tech which is still beyond state of the art for e-cars.)
They were hung up on their idea of what it was going to be and never tried developing alternatives when they were still protected by patents. I think they never really understood why their product failed in the marketplace.
I grew up in Manchester, NH where the Segway was invented and went back there a few times when it was being test marketed. I'd see people going up a hill on it, going down the sidewalk and forcing pedestrians off the sidewalk, and the cops cruising around behind the K-Mart looking right out of Demolition Man.
It was kinda cool but obviously not a revolution and how they couldn't see that was beyond me. For one thing it doesn't give the protection from the elements which is an important attribute cars have if you live in a place like the Northeast U.S. where winter and rain are a part of life.