WATCH: How Being Gay and Bad With Money Can Lead to Prostitution

How does a nice Jewish Patti LuPone fan become an escort?

Out playwright-performer Ben Rimalower details his long history of debt in Bad With Money, his autobiographical new one-man show at New York's historic Duplex Cabaret Theatre.

Rimalower's "addiction to spending beyond his means has driven him to extreme lengths all his life," read press notes about the production. "In Bad With Money, he charts his sometimes hilarious, sometimes harrowing struggle to overcome his problem -- or get rich trying."

At 21 years old, Rimalower's interest in "having sex for material gain" led to him escorting for strangers in San Francisco -- a salacious story he candidly shares in a new video clip of his performance.

A celebrated director, Rimalower made his debut as both playwright and performer in 2012 with Patti Issues, which drew parallels between his connection to diva Patti LuPone and his strained relationship with his gay father. The Advocate named the solo piece among the best LGBT-inclusive New York theater of 2012, calling it "smart, poignant, and dishy as hell."

Watch the first preview of Bad With Money below.