I think the biggest problem was that nobody took it seriously, and I'm not really sure why. It was easily as good, if not better, than the iPods of the time. I definitely don't think it was an issue of timing though. the iPhone's capacity at launch (8GB) was a joke compared to dedicated players at the time. And music streaming services weren't all the popular. Plus even if they had been, it would be a year until we saw a 3rd party app store on the iPhone.