I've been feeling the same way about my startup, which has almost 17,000 users but only a small amount of them are paying customers (launched a paid plan a few months ago). I keep wanting to ask myself how much longer I should give it to see if it reaches profitability, or should I just shut it down? Anyway, right now I'm creating a survey for the paying users to be able to tell what they like/don't like about the paid plan. I also plan on doing a referral program that benefits both parties (I did get both of those ideas from a slideshow about a startup and their freemium model, forgot which). Keep those ideas in mind if you ever plan on introducing any paid plans and good luck.
Thanks. I really appreciate the feedback and advice (from everyone on HN). The whole "wondering how much longer I should give it" phase lasted from about February until early April.
One of the first things that made me realize it might be time to cut my losses and focus my attention on other projects was when we launched this website in mid Feb - http://toeflnow.com
We sell a TOEFL Tips and Strategies guide eBook, and while it certainly isn't earning enough to pay all the bills it is making substantially more money than Lenguajero. In fact, in its first week it made more money than Lenguajero did the entire month of Feb.
That was a real turning point. It was like "Hmmm...hundreds of hours spent on Lenguajero vs. ~40hrs spent on an ebook. Maybe I should be doing something else right now..."
Good luck! I really hope it works out for you. What's the website if you don't mind me asking?
