Jacob B, you should not have a 1/4 line coming FROM your direct box.

The convention is 1/4 out of the guitar and into the box, XLR out to an XLR line to the board. Those inline transformers are not worth the money, in my opinion. The Behringer DI 100 is an active DI (run either off a nine volt battery, or phantom power from the mixer). It is an excellent DI (I have 8 to use with my systems) and the price has dropped from $65 six years ago to now about $30 (try americanmusical.com). It also has two 20db pads and a link which allows you to plug your guitars 1/4 inch into the box (Input), plug another 1/4 out to your on-stage amp (Link) AND send a balanced signal all the way back to the FOH mixer. (Way better than just micing the amp).

Just remember that when you go over twenty feet to, or from, on a 1/4 line, you are really stringing up a twenty foot radio antenna, that is cutting your highs the further you go. With a balanced line (XLR) you can go up to 600 feet.