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"I need to figure out a way to remind them of my policy with out seeming like a total jerk"
The day you start thinking you're a jerk asking for money is the day you should close your doors. If they run their own business and don't understand why you need a deposit, then I think you should think about other arrangements as they truly don't value you or your business.
If they have kinks to work out, let them work them out. But in the meantime, tell them to start writing the checks. Their problems should not become yours, and from the sounds of it, it sounds like they are. It sounds like they are sticking their hands more into your pockets to cover the lack of funds in their own. If they want to play GC, then let them play GC and do the work they are getting paid for. Like most gc's, it sounds like they are trying to make more money and do less work. Be very careful with this situation, as it sounds like it could go sour very quickly.
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