Usually when I want a design on burlap, I just print it onto the burlap...but since I plan to keep this outside I wanted to make sure the ink wouldn't run so I used paint instead of ink. I did, however, use my printer for the first part of the process. I started by designing my flag in PicMonkey. It's a free photo and editing site that is just full of awesomeness. It's easy to use, free and has tons of font and designs to pick from.
Since I have to cut out the design to make it a stencil, I tried to keep it pretty simple. To make the circle I first made a black circle, then made a smaller white circle, placed the white circle on top and then added the 'V'. Once the design was ready, I saved it. I like to bring my designs into PowerPoint to size them since each slide is the size of a piece of printer paper and I can get a better idea of how big my design actually is.