I loved the way that you started your elevator pitch. A short narrative can really grab the audience’s attention. I felt emotionally invested and connected by the end of your elevator pitch.
I liked how you broke down the stages of development/involvement. The beginning stage was free which I liked because most people will look for that type of information on free services anyway. I use youtube to learn how to do all sorts of things from taking screen shots on my android device to rebuilding a carburetor on my motorcycle. I think your plan to have the more elaborate services be subscription based. For example paid users can be part of a collaborative community. What I am worried about is that your venture will not be much different from the competitors that you discussed. For your next iteration I would elaborate on how your service will be better than the competition.
As an educator and possible user of this service, I would request that the analytic be removed or changed. I don’t like the idea of my institution or supervisor evaluating me based on my proficiency with your service. The analytic could be helpful, but it will be met with resistance, especially in Canada where most educators belong to unions and contract language that prevent this type of evaluation.
I would be interested in investing in something like this if these few issues were worked out. Especially, as you pointed out in your venture pitch, there is a growing need for IT training in schools and universities.