At the point that it costs you more than sending a reminder email every week or so. For $400 just take the lesson and a) Never work off contract again. Even

At the point that it costs you more than sending a reminder email every week or so. For $400 just take the lesson and a) Never work off contract again. Even in small projects that you wouldn't want to go to court over even in the worst case, sometimes they can help prevent the worst case. At worse they can give you a list of assumptions and clear up some misconceptions before you start (most of my simple contracts for small projects were just assumptions like "If you get me all content by DATE, I can have ABC Feature done by DATE2" etc b) Always downpayment up front c) Incremental releases and payment structure (I release this feature, I get this payment, etc., instead of lump sum 50% remainder at the end) d) Trust your gut: I imagine you knew this guy was shitty going in (I almost always have, and in retrospect clients who didn't pay me I almost always had a bad gut feeling about and then convinced myself to do the work anyway). e) Internalize the concept that time not wasted on shitty clients can be used more effectively to look for good ones. Good luck!