I ranked Entry #2 first because I like how the sizing of SMCM compares with San Mateo Capital Management beneath it. I also liked the font. The things I would change are the bottom color - possibly dark blue replacing the gray? - and possibly the convex line going through SMCM.
I liked how the logo appears within the lines on entry $5, but my concern is that the Capital Management part would be too hard to read if it was on a business card.