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Emile comments on How a pathological procrastinor can lose weight [Anti-akrasia] - Less Wrong
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Wouldn't it work just as well if instead of money, you used "reputation" in the form of a public profile?
I wouldn't be surprised if group pressure was more motivating than money, and it also lowers the barriers of entry so you get more people in. Plus it avoids all the legal and fraud issues.
Yes, to a degree, and that's why we have that (opt-in) public gallery on kibotzer.com. But if you (probably rightly) suspect that your friends have stopped paying attention to your graph, then it's easy to fall off the wagon. Speaking from experience. :) The wager idea also has an aspect that's hard to capture with shame (powerful as that is), namely the anti-procrastination aspect. You can dig yourself in quite a hole thinking you'll catch up soon and undo the (only gradually building) shame.
Have a sidebar with "today's LOSERS"
Instead of money, have users give a list of email contacts. If the user fails, all of the contacts get spammed with a failure message written by the user when he starts (the contacts don't get spammed when the user starts or succeeds, so he can keep the list big).