1. It means "queen" in the dothraki language. Usually the wrong-given name to Daenerys Targaryen, character from "A song of ice and fire" books (Game of Thrones).
2. Badass sexy girl who has dragons and says "dracarys" to her enemies and burns them all. She gets the things she wants with fire and blood.
Originating from Game of Thrones term "Khaleesi", the term defines the complete and utter annihilation of seemingly insurmountable obstacles, usually business related, by a single individual. Possibly involving dragon fire. The replacement of the "s" to "$" serves to add gangster credibility, while also indicating that a great deal of money was made whilst setting fire (literally or figuratively) to the competition.
Queen Daenerys I Targaryen is the younger sister of Rhaegar Targaryen and Viserys Targaryen, the paternal aunt of Jon Snow, and the youngest child of King Aerys II Targaryen and Queen Rhaella Targaryen, who were both ousted from the Iron Throne during Robert Baratheon's rebellion.