James I think you are focusing on the wrong market. Your potential paying customers are not students, but their parents who have the money. One idea might be to allow parents to track what their little darlings are doing on the site. Another is to provide regular feedback (email, newsletter) to the parents about how their children are progressing.

Not sure how things are where OP is located, but some parents may not be able to afford something like this depending on their income.

If this works well integrated with school activity maybe it could be payable through that?

The OP is in Australia like me and while there are lot of parents that can’t afford to pay, there are lots of that could. The key here is to build your business around the customers that can pay, not those that happen to use it.

One other idea might to try and partner with companies that are trying to lock in young people. The obvious one is banks which are always trying to target this age demographics. You could offer, for example, premium notes to those students that had an account with the sponsoring bank.

What have your experiments looked like? How were you measuring them, and at what rate was your revenue growing? What's your current core metric, and what's been happening to it over the last few years?

One experiment involves offering a subscription service to online premium study notes. We measure number of subscribers, downloads, and revenue. Students who subscribe typically keep and use the subscription until they finish school: the biggest problem is the very low conversion rate in the first place. We know that students want study notes, because they download free notes from our site all the time, but very few are willing/able to pay. This is a recurring theme for us: we get enormous interest when offering something for free (whether notes or seminars), and get complaints as soon as a price tag is attached.

We reached the point a couple of years ago where we realised we had largely captured the maximum potential user base in our home state, which left two obvious strategies: growing revenue (in that state) and/or growing the user base (in other states). From that point our core metric has been revenue, with a view to further growth once we had nailed the model. Our primary revenue source has been advertising (from universities and colleges and others), as that seemed to give the greatest return for the fewest complaints. It grew very quickly from zero, but has stagnated in recent years as advertisers developed a preference for programmatic platforms. That shift has prompted the present search for a new business model. Meanwhile, the community itself continues to thrive.

Have you grown to other states?

We have at least a small user base in every state, and also a small user base amongst students who started with us and went on to be accepted into universities and colleges, but to date we haven't invested significant time or effort into growing either. We've been too focused on trying to work out what the business model will be at the end of the day. Would you recommend a different approach?

I think you either need to grow the user base significantly or figure out how to increase revenue. Based on what you said, it sounds like you need to do the first now, because you've tried all the revenue paths.

Thanks very much for your time and consideration, Aaron—this has been helpful.