Suggestions:
Now that you have some money, hire a designer or three and have them produce a couple of dozen designs for you under various themes. Now you have something to browse. And promote.
Another thought: Hold a contest of some sort. $10K to the design that pulls in the most sales over a period of time.
The best Obama t-shirt contest?
The nerdiest t-shirt contest?
The funniest t-shirt contest?
All of the above?