Not everything can be your best work.
After the Juice project was killed, J Allard, the legendary creator of the XBOX started putting together a company wide effort to "take entertainment seriously". J recruited me to come over and run the services team. There was a clear effort to recreate some of the magic behind the XBOX. J secured a different facility for the team and we all got different business cards.
On the upside, the project got lots of resources but unfortunately that meant it a frankenstein effort of bits and pieces of my team to run services, parts of the Windows Media Player team for client software and some phone guys on hardware. None of us knew or particularly liked each other and there were hidden and un-hidden agendas everywhere. The XBOX folks were recruited mostly against their will since what they really cared about was gaming and they thought that it was too early to declare victory there. We were given 9 months to get from introductions to a shipped product and the relevant comparable was the iPod. Microsoft in it's infinite wisdom adopted the "two in a box" management philosophy where two senior leaders of differing vision and style were asked to co-lead the project. Spinning up our own hardware from scratch in that time was impossible so we ended up modifying a not very well selling "plays for sure" device from Philips. We were stuck with Windows Media Player and it's very limited skinnability for client software. For the music service we were forced to do a partnership with MTV Urge.
The real tragedy is that we did have a killer feature where the devices could trade songs amongst themselves wirelessly and after months of work, the lawyers signed off that we could release it. (Hey, it's just a hard drive that copies files right?) Unfortunately senior leadership convinced themselves that nobody would take our device seriously unless you could buy Beyonce on day 1, so we were stuck doing deals with all the major record labels and by the time they were done imposing restrictions on the feature it was more of a cruel joke. We ended up not even touting the feature.
The XBOX had an arc where the first effort was clearly cobbled together and the sequel (the 360) was inspired and had real marketplace success. In retrospect, Zune tried to run the same strategy - the first effort was cobbled together at breakneck speed, but the second iteration, the Zune HD and the related custom client software was actually really good. Sadly, market timing did not work out as well for Zune as it did for XBOX. Steve Jobs introduced the iPhone and the world quickly moved on from music players to phones where Microsoft was once again outclassed.
"The iPod had to move over (even if only a little today), and now it's turn for iTunes to move as well."
"With the Zune being launched shortly, there’s no better time than now to take a quick stroll through its native software. It’s pretty, but has a lot of functionality as well"
"As rumored, Microsoft announced a new feature last night allowing high-definition movie and television downloads directly to your 360's hard drive."