I propose that Learners individually reach out to Teachers, and set up meetings.
Consider that it may make sense for you to act as a Teacher, even if you don't have a super strong grasp of the topic.
Why that way instead of the reverse? True, the learners probably have the greater motivation. But, the learners have a better idea of what they want to learn than the teachers have of what they can teach, especially if we're accepting teachers without a super strong grasp of their topics. Thus, I think it would make more sense for the learners to post in detail what they want, and the teachers to look over all of that and make the offer on whatever topics they can help with, even if only a little.
We could certainly do both, but then I worry that each will hope the other initiates. The cure for this is if one individual plays matchmaker to get things started. Due to the bystander effect, I'll name adamzerner as the obvious choice for the role, but you could delegate then abdicate if someone else is willing.
I pinned http://lesswrong.com/r/discussion/lw/p69/idea_for_lesswrong_video_tutoring/ to #productivity on the LessWrongers Slack group.
A chat room could also work better than individual emails. But everybody has to be on the same channel and check it regularly. I don't even have an invite yet (I just asked Elo for one). Is everyone else on?
Update 7/9/17: I propose that Learners individually reach out to Teachers, and set up meetings. It seems like the most practical way of getting started, but I am not sure and am definitely open to other ideas. Other notes:
Update 6/28/17: With 14 people currently interested, it does seem that there's enough to get started. However, I'd like to give it a bit more time and see how much overall interest we get.
Idea: we coordinate to teach each other things via video chat.
So, this seems like something that would be mutually beneficial. To get started, we'd need:
Personally, I'm not sure how much I can offer as far as doing the teaching. I worked as a web developer for 1.5 years and have been teaching myself computer science. I could be helpful to those unfamiliar with those fields, but probably not too much help for those already in the field and looking to grow. But I'm interested in learning about lots of things!
Perhaps a good place to start would be to record in some spreadsheet, a) people who want to teach, b) what topics, and c) who is interested in being a Learner. Getting more specific about who wants to learn what may be overkill, as we all seem to have roughly similar interests. Or maybe it isn't.
If you're interested in being a Learner or a Teacher, please add yourself to this spreadsheet.