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In business as in love, the “Friends with Benefits” arrangement sounds ideal. You just set up a little somethin’ somethin’ on the side without setting any expectations. It’s added excitement without additional overhead. No commitment. In theory, it sounds perfect.
In reality, the FwB thing rarely works out. Sure, it starts out great – you get together once a week, mess around a little bit, talk about how clever you both are, etc. Unfortunately, as time goes on
Jake,
I agree with you that FwB partnerships are very touchy. I've been in partnerships where we started up a product, only to find out that neither of us was very passionate about the product, and eventually one person started doing most of the work, and it went downhill from there.
I'm also in a current partnership that works out very well. I think the reason for this is that all three of us in the partnership are good at separating work and play. And we have very complimentary skills. I think starting a partnership with people who have overlapping skills causes more issues, simply because there's only so many "fun" tasks to go around.
I agree with you that Patience is a must to let these relationships flourish. But I would also add Be Clear along with Be Patient, so that if you are "anal on deadlines" people know where you are coming from and you get your expectations met. I think it's admirable, not anal to stick to tight deadlines, but you're right that not everyone feels that way. This may be a good litmus test for future FwBB relationships. Perhaps those that pass the Deadline test can graduate to FwBB, and the rest just stay F! For others, they need to find their own litmus test and apply accordingly.
From my own experience, sometimes a lack of overlapping skills doesn't help, particularly when the parties involved have very different roles and goals in a project. You think you know someone, until you start working with them. That is why I second Caroline's suggestion that Be Clear is added for consideration: if everyone knows what everyone else hopes to get out of a project, then there are fewer disappointments down the road.

Having a good business understanding, risk analysis and respect is essential if you are going to succeed working with friends. I have done business with friends before and I'm very skeptical about doing this again since it is a very hard payload to every friendship.