The decisions listed (buying a house, retiring, paying for college, etc) are all fairly infrequent, separated by many many years - so not much value from return users. I think getting $$$ from people for that is going to be very very tough unless they can quickly expand and become the "financial decision-making engine" for pretty much every $500+ purchase in your life.

If that's not in the cards, they must be thinking of (A) targeting intermediaries (e.g. mortgage people at banks to use with their clients), or maybe (B) planning something a-la-Mint (e.g. present you with relevant offers to whatever it is you're considering buying/leasing)... or maybe something else?

Curious to hear how you guys are planning to monetize...