In our previous startups, my co-founders and I have always had a desire to have a strong "always on" remote connection between offices. Back when we had DC & SF offices a few years ago, we tried setting up what we called "Project Stargate" using Skype. However, the connection would keep dropping, so after a few months we abandoned the effort.
The main lesson we learned from that experience was that reliability matters above all else. The best remote connection setup in the world will fail if it isn't rock solid.
With that in mind, when we sold Socialize to ShareThis, we were suddenly in a situation where our SF office was joined by offices in Palo Alto, New York, Los Angeles, Chicago, Texas, Boston, and others, so this remote connection issue became even more important to solve.
Luckily, there's a great startup called Sqwiggle that's working to solve this problem. They've taken an innovative approach: Instead of solving the vexing issue of having a reliable "always on" video connection, by default, users are shown in boxes together but as black & white thumbnails that update every 15 seconds or so, meaning the only thing that has to stay "always on" is an old-school web page. This always lets people be "together" while still having privacy, as there's no audio or video unless two or more parties enter into a conversation.