It should be something that would look at place or fit sensibly on a dollar bill or within a circle or coin, (thus the cigar label) or close to it. Not face only, but face & shoulders, maybe a hand holding the pipe? Maybe a pilot's scarf around neck or cravat, blowing behind? Not so much face on like George on the one dollar bill, maybe more of a partial or 3/4 profile?
As far as the word "DaddysFastCash" it's supposed to depict an answer to a question, it's a name and action, noun and verb.
Back to the Currency look, the name DaddysFastCash should fit under the iconic image. Again, the One Dollar bill & George with One Dollar spelled out under is sort of getting close.
You can get creative. I do want cool and I am looking to brand it. Right now it's a nickname I house to buy and sell houses (don't go crazy trying to include house imagery, it's bigger than that), but it is a quirky character I like to play. Thus the cigars with my (logo) face on them. So it may end up on the side of a car, on tee-shirts, etcetera, and I will need some consistency of design.