She began working as a prostitute in 1881, supporting her family on her earnings,[1] and opened a brothel at 172 Customhouse Street prior to the murder of her brother Peter Deubler in November 1890.

While the witness accounts were disputed for years, Phillip Lobrano claimed that he shot Peter Deubler in the face in front of his sister Josie in self-defense.

She and Brady had visited the Arlington Hotel in Hot Springs, Arkansas and she witnessed first hand a luxurious lifestyle and resolved to emulate it back at her brothel.

She changed the name to the "Chateau Lobrano d'Arlington" and began to hire foreign girls to increase the appeal to upscale customers.

At this point, she began making business deals with Tom Anderson who operated a nearby restaurant which he renamed the Arlington.

[2] Anderson caught wind of Alderman Story's ordinance to create a regulated prostitution district before most did, and he and Josie acquired choice properties on Basin Street near the entrance to the future Storyville area.

[2] In 1898, when Storyville was established, Arlington moved her operations to a four-story frame mansion at 225 North Basin Street.

As an expensive "$5.00 House", it offered about ten or twelve girls at any time, as well as a live sex 'circus' that could be viewed for an extra fee.