Looks very nice and a nice idea :) you could expand the idea to other fields (like going over bills, etc.) Makes me think of a backward Tamagotchi where the computer takes care of the human :)
Having "robots", whether chat bots or something else, look at your data and make suggestions on how to improve is something I find super interesting. One for your finances certainly is a n interesting idea.
Do you think this working better for yourself (and your friends, I take it) is a result of motivational agents being inherently more effective as chat bots than traditional push-based systems (SMS/emails/app notifications)?
Example: My girlfriend joked recently, after starting to exercise a lot more after a short hiatus, that she was "rekindling her relationship with Jumper." I found that statement pretty deep - that's not something she would have said about a standard exercise app (I think?).