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Whoa, you're giving each person their own number (as opposed to, say, an extension). That means you're paying $1/customer/month even for dormant customers. Seems like a really bad call.

Other than that, I really like it. Sorta like Awesomeness Reminders, but recorded by people who love you. Design could use some work, but the signup flow was nice (not requiring any info but phone number). Though now the only way to login involves you calling me again and telling me the pin I already know, which isn't great.

Also, I'd stop using a redirect and set it up so that Appengine serves write.

Thanks for the feedback! I plan to add some more features and tidy it up a bit, but I wanted to see what people thought.
That means you're paying $1/customer/month even for dormant customers. Seems like a really bad call.

I do this for Appointment Reminder, too, mostly out of sheer laziness. I might revisit it eventually, but it hasn't broken the bank yet. (Finding my own number on my Twilio interface has gotten annoyingly complicated, though :) )

But people are paying you. Right now his service is free.
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It's telling me something.
Cool idea! You probably weren't expecting to have an issue like that. In retrospect, having a nice friendly fail page would earn you customer love. Especially on a site relating to how people are feeling.
Looks like a good idea to me.
Have you tried using Compassion Pit? Made by the same guy who made Awesomeness Reminders, mentioned by another commenter. Basically the same concept, just web-only. Could be a cheaper start for gathering a user base and gauging long-term interest.
Great idea. But what if no one loves you?

To address this, you might be able to automatically generate moral support. You just need to add a 'link to Facebook' feature along with a little machine learning + speech->text->speech algorithms so that the most 'appropriate' message can be generated given the current time and the user's Facebook status.

With enough data to bootstrap the system, we'll probably end up not even needing other people IRL.

Lots of great comments so far, I really like the idea. Good luck building interest!
I don't know what to call this. Part of me has an instant reaction that it's a terrible idea, but on reflection that's because I'm uncomfortable with it. So that's prejudice talking. If I look at it rationally, it seems like this just might work. It's kind of brilliant.

One suggestion: people who don't reach out to others are not going to buy this product for themselves. So, it should be giftable. Imagine if you have a friend who's kind of a sad sack or is going through a divorce or death in the family. You and N other friends record motivators. It's like signing a condolences card, only way better. Actually more personal.

Thanks for the idea. I think i'll implement the 'gift' mechanism.