Don't Cri-Cuts come with instructions???? "I downloaded it right off a website and it just won't cut, funk-dat!"
You need to make sure it is a vector, if not you need to "trace it" and then send it to the cutter. Remember the cutter is only going to cut the wireframe, so be sure to look at it in the wireframe view before plotting, this way you can node edit to smooth things out. It is alot more than copying an image and hitting cut.
Just a question, did someone charge you "too much" for some lettering so you decided to do it on your own? Seriously, I would like to know.
I would be willing to train you in signmaking, Mosh's Skule of Vinyl is now open.