I have both of these watches. Personally, I think that the 1st gen 360 looks nicer but the Zenwatch 2 is much better in terms of performance. With my 360, I am lucky to make it to the end of they day without the battery dying. In addition, at around the 15% battery mark, power saver mode automatically kicks on (I think this happens with all watches), and with the 360, I usually notice an extreme amount of lag when this power save mode is activated. With the Zenwatch 2, I usually have around 40% battery left at the end of a day with heavy usage. I wear them both, but the 360 better suits me for occasions where I want to wear a nicer looking watch. One last thing about the Zenwatch 2 is that I got the gunmetal one with the dark brown leather band and the clasp, and it took a few days for the band to break in and become comfortable. Now it is great, but I almost returned it on the first day because it was digging into my wrist. If you get the Zenwatch 2, just stick it out with the band for a few days before you judge it. I also bent the leather back and forth on the first day in order to help it break in a little. Just my 2 cents.