Most of my time as the developer of Strategic Board is spent on how the hell can I make money from this. Strategic Board as many other Web 2.0 sprouts and trees create "value" in the new content creation era we live in a.k.a as blogging. Blogging both for users and publishers is free and finding a way to capitalize on a basically free thing is a very sophisticated riddle. People in general don't pay for information that can be reached in other free ways.
The options to make money I see today are:
1) Put ads on my site and get clickthrough money. A business model that is not integrated into the "value" I bring to the table. Needless to say an almost lost fight with the brands out there.
2) Create few niche services, provide a free entry level account and charge for unlimited usage. This can make me busy for six months (developing it) and maybe can take the business model thoughts out of my head for while though I'm not sure it will be the right way. The best case here might be a situation where few information maniacs will pay me subscription fees while others will find their information in other places or not at all.
3) Do partnerships with others that like you don't have money coming through as well. This can be very nice on the social and spiritual level but I'm not sure my bank manager will appreciate it.
All these poor alternatives stand in light of tough competition by large rivals who are lurking for your service eyeballs. Whether it is Google who makes money directly from your eyeballs and receive exposure on your back (Google Ads) or Yahoo/MSN who are running crazy to get all the people who are going today to Google in order to do what?. Competing with them on their turf (the eyeballs arena) is impossible due to their massive capacity and selling the business after bootstrapping to them is also not that great idea at least morally.