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What I've overheard on some podcast discussions is that they are taking the multiplatform Silverlight runtime, and have enhanced it to be a headless server-type runtime instead of browser-plugin-UI-focused. It doesn't include all of the windows-only features of the CLR and BCL, but has all you need for ASP.NET vNEXT.

I think Xamarian made a very good move in getting into cross platform toolkits, rather than just relying on support contracts for Mono. At this point I think they're in a position where Microsoft Open Sourcing the .Net runtime isn't going to hurt them too badly.

I would expect that Xamarin's role with Mono is analogous to 37signals\Basecamp is to Ruby on Rails. Neither organization makes money developing Mono nor RoR. They make their money supporting and consulting organizations that chose to use the software that they are developing.