can't remember where I heard this but the advice was basically this: When pitching your idea, and generating excitement, ask for money (or a commitment) on the spot. There's a big difference between saying you'd pay for something, and paying for something.

The flip side is that sometimes it takes awhile to build the perception of value, hence free trials/freemium models. Get people hooked, then ask for $.

There are many ways to be successful (and even more ways to be unsuccessful).

This chimes a lot with what I've seen, and indeed, what I do myself. I had a few friends plough hard-earned money into a really bad start-up idea (basically an inferior pay-walled Wikipedia), and instead of telling them what I really thought of it, I weaselled out saying something bland, non-committal and mildly supportive.

Hence my rule “only ask for startup advice from friends who have told you previous ideas were incredibly stupid”.