Abstract: A method and system for collaborative investment and financial planning between one or more investors/savers and one or more matchers/contributors utilizing a web-based system facilitator is described. In an embodiment of the present invention, the method and system enforces the collaborative investing plan between the investor and the plurality of matchers by immediate notification to all parties once any party fails to make the monthly contribution or the investor withdraws from one or more investment/saving vehicle accounts before the end of a predetermined time period. Matchers/contributors decide whether to discontinue or continue participation in the plan. A fund transfer mechanism is utilized in the method and system to facilitate fund transfer from investors and matchers to selected investment vehicle account(s). In an embodiment of the present invention, the method and system further transmits to the parties of the plan, messages providing investment updates and information on financial topics.