Personally, I'd like to keep the Do The Ton in brandish font on the 3"-4" circle, if nothing else than to pay homage to the site. I like shape of the hat and the rest of what you have going on in the circular one. I think he looks like el Guapo. The checks and spade may be overkill. One or the other should get the point across and clean it up a bit.
I'll try to lure the DFW crew in here to give more feedback, but I'm stoked to see what you come up with. Keep it up.