Not an experienced entrepreneur, but FWIW, don't take on Blackboard's existing products. Make a gamble on what's going to be important for managing courses in 5-10 years and start building that.
Online testing is probably going to be more important; video-delivery of lectures is going to be more important; mobile access (especially for instructors) is going to be more important; massive enrollment is going to be more important. It's hard to imagine that Blackboard will do any of those well.
Online testing is probably going to be more important; video-delivery of lectures is going to be more important; mobile access (especially for instructors) is going to be more important; massive enrollment is going to be more important. It's hard to imagine that Blackboard will do any of those well.