Show how bills are settled using a cool visual aid.
This idea came from a bout of minor confusion I had when looking at the results of the "settle up" function. I was surprised to see that despite knowing that I owed various people money, the result I saw on screen was that I actually just owed one person. After some chin scratching, I realized that of course the bills were being aggregated together so as to minimize the number of payments needed to settle up. That being said, I'm not sure that everyone who uses this service will reach that conclusion, especially if they've had a long day at work and weren't in any mood to use their head. So, how about you try implementing a flow chart sort of graphic which shows how money is aggregated together? Have all the bills on the left side stacked vertically in their own boxes, then show the path each bill takes, merging with other bills like tributaries feeding into rivers, and then have each river of bills end up at each person, whose names are arranged on the right side of the screen. That may be what it takes to intuitively convey how the bills are compiled. Or it may just end up as a confusing mess of lines, but it may be worth a shot.

Recently we’ve been thinking a lot about this exact problem. The “settle up” function is great once you understand what it does, but it confuses a lot of first-time users. We’re working to improve communication about this, including via visual aids – you should see some of those updates over the next few weeks :)
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Sam commented
yes please !! This features will save a lot of people from a hell lot of confusion !
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Eric commented
Wicked cool dudes, great to hear that the pistons are pumping, and best of luck with your continued growth!