Do you design for Neophytes, Early Adopters, or tech nerds?

When designing your software, app, platform, etc do you shoot for a middle ground or do you look to create the lowest common denominator product for understanding and usability by the masses? It frustrates me to no end that we all forget we had to 'learn' FB and twitter. We had to explore, discover, get dirty. When getting friends and family input, it is very frustrating when you get back 'I don't understand's' and while they are very valuable, it is certainly annoying when they forget there is always a small learning curve with a new idea and concept. So, for your best projects, did you just say to hell with it and design/UX for the LCD, or did you say 'they'll learn it and I'll get it as close to simple understanding as I can, but they need to stretch a bit too'.