Overview
A friend is about to take a big risk, and you are worried -- and torn. You want to keep them from making a mistake, but you don't want them to think you don't believe in them. Just try to do your best to help them see things more conservatively -- alert them to the downside of their idea, and what could happen. Ask them if they are ready for a worse case scenario. They'll know you are speaking from a place of caring, not judgment. Just remember that in the end, it's still their call.