imagine- wrote I learned some tips from my brother (artist for American Apparel.

Draw out what letter you are trying to work with a piece of blank paper, doesn't matter where, and start making any adjustments you can to it, try putting something under it, just make as many logo concepts you can on the piece of paper.

After you are done, or feel you like one of them, take a picture of it, upload it to your computer, then open it in photoshop and trace it with the pen tool.

I hope i helped
-Imagine

Im sorry but if your brother works for AA he wouldn't use photoshop's pen tool. It is poop. Either uses Illustrator or is really bad at his job.