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I use the dollar sign as an acknowledgement of the influence of Ayn Rand and Objectivism on my philosophic beliefs. I am named after my father and, rather than "Jr," I am "the second." (Thanks, Mom!) When the roman numeral two is written quickly it looks very much like a dollar sign.
The gold dollar sign comes from Rand's novel, "Atlas Shrugged." In the novel the dollar sign is the symbol of the rational, productive human being who trades peacefully for the result of his labor and talent. I read "Atlas Shrugged" as a teenager along with Rand's other novels and was heavily influenced to my present philosophy by the principles of Objectivism. I adopted the dollar sign into my signature as a small homage to Rand's influence.
Objectivism is a good start as a philosophy. It is, however, rather weak in the area of human emotions and relationships. Rigid and literal adhesion to Ayn Rand's words can be personally destructive. See the later works of Nathaniel Branden for some explanation of this.
Unfortunately, Objectivism has been hijacked and warped by Leonard Peikoff and the Ayn Rand Institute. I caution everyone to avoid Peikoff, the ARI, and anyone associated with them. They are essentially a cult. For a more reasonable and non-destructive version of Objectivism, see The Objectivist Center.
Despite all the problems associate with Rand and Objectivism it is inarguable that she has had great influence in the resurgence of rationalism, free market economics, limited government, and libertarianism. I, therefore, keep the dollar sign to remind me of the best that she gave to me.