In a way it does exist. A lot of people get this kind of encouragement and "quality listening" from psychological counselors. This means that there is an opportunity here, because psychological counselors are usually overqualified for the simple encouragement an entrepreneur may need, and thus tend to be more expensive than what I expect your price point would be.
In short, I think that re-framing the service as an "entrepreneur's counseling service", including such things as a guaranty of confidentiality, has potential. The thing to remember is that counseling requires a human touch, so any technological contribution is going to be of the nature of putting entrepreneurs in need of encouragement in touch with counselors. Having a ready source of inexpensive, entrepreneur-specialized counselors is definitely a service. How much demand there is for it, I don't know.
If you get it together, tell me your rates. Cheap enough and I might use it myself.