I like the idea of looping in friends, I just wouldn't make the dollar payouts to them. I can imagine people enjoying sending money to their friends, partly for ironic comedic value (lol look how helpless I am, haha now we have a funny story of how I can't control myself and you're a terrible watchdog - maybe I'll even screenshot and post my failure so that our other friends can ironically enjoy this). For similar reasons, I also wouldn't pay my future self with the money. I can imagine people appreciating that as a way of forced saving, and you don't want them to appreciate the monetary loss at all. In fact, you want them to hate it - hence part of the punishment being a donation to a group that they don't like. The great thing about that is that the cost of the punishment could far exceed the monetary value of it - if you really hate a political party, the perceived cost could be 5x the dollars donated. Good luck with your program, and shoot me an email if you're interested in discussing further. My HN email address is in my profile.

That makes sense; I know people who've tried out this app called StickK where you donate to anti-charity if you don't follow habits. Definitely something on our minds.

Thanks for the share, Stickk looks interesting. Stayfocusd + Stickk, with cross-platform usage tracking, would be the holy grail. Another thing to note is that Stickk has a lot of user complaints, so there’s a lot of room for competition if they don’t iron out the kinks.

That's a very interesting thought. Yes agreed - StickK has a lot of user complaints so we would need to execute much better. A lot of these complaints arise from the fact that StickK literally puts you in a binding contract to pay the money - which may be necessary to enforce their kind of product, but also gets a lot of users angry and confused.

I looked at some of the negative reviews, and they seem to have a point.

1. The irreversible, binding contract element needs to be exceedingly clear and simple to understand as soon as someone opens the app for the first time (“you will not be able to contact us to reverse the contract, so choose your terms carefully”). Additionally, give users the reason why the contract is irreversible up front so that they understand the app’s foundations. I would want the contract to be irreversible, that’s a feature not a bug, but users should know that. Users who aren’t comfortable with that should ideally be offered a weak alternative as long as that doesn’t muddy the service. Otherwise, turn them away.

Even the button that users press to agree to a contract should be called the “No Way Out” button or something like that. However, great care should be taken to ensure that users who behave well don’t get punished (e.g. agreeing to pay $X if you don’t lose weight, and you lose weight but there’s a bug with reporting that, or the app doesn’t ping you enough to warn you to check in, or you don’t understand the consequences of not checking in, or there wasn’t enough granularity with the terms of checking in). Users who don’t trust the app as an automatic executor of contractual punishments should be able to designate a third party arbitrator, like a friend or parent, but that shouldn’t be the default option. Maybe the user’s friends will be lenient, but let them find that out.

2. They have both a “charity” and “anti-charity” option, which is fine. However, the structure of the “charity” option is problematic. It is not clear to users picking that option that their funds may go to a charity they actually dislike, making it more of an Anti-Charity. Additionally, for both the charity and anti-charity options, they should let the user choose their level of granularity. If a user wants to designate specific organizations, let them make that trade off. Maybe someone is willing to make a particular political party their anti-charity, but never in a million lifetimes the Coalition for Coal (made up). “Charity” and “Anti-Charity” are vague. There’s a fine line between motivating your users and provoking unmitigated rage in this space. If that’s hard with the “charity” and “anti-charity” categories, maybe they should be scrapped entirely.

3. It seems like they have UI, usability, and bug issues.

Again, I think that the concept behind their app is great, and they have a lot of potential, but there’s an opportunity for you to do everything they do but better.

Thanks so much for this! I've saved this analysis and will keep it in mind as we decide to move toward this direction. Agreed with all three of your points; we can definitely have better execution on all these fronts.