[4] This coincided with the collapse of one of his business ventures, the Howell Academy, a private boarding school at which Womack reportedly was rarely present.
[3] After the closing of the Howell Academy, Womack enrolled in a Ph.D. program in philosophy at Johns Hopkins University, receiving his doctorate in 1955.
Through a holding company, Womack invested in a Maryland start-up, Polytronics Research, whose stock price subsequently soared when it was falsely claimed that it had secured a lucrative government contract.
The fraud was ultimately detected by the SEC, but Womack escaped prosecution, as investigators judged that he was merely a "naive academic" who had been roped in by co-conspirators.
He made half a million dollars from the scheme, which would serve as initial capital for Guild Press and allow him to leave academia.
[4][6] In January 1960, Womack was arrested, alongside photographers Anthony Guyther and G. Rodney Crowther, charged with sending obscene materials through the mail.
As a result of these new charges, the judge who oversaw Womack's earlier case revoked his bond, sending him to prison to serve out his one to three-year sentence.
At the time, homosexuality was still viewed as a mental illness, and Womack, who had a degree in psychology, was able to manipulate the doctors who interviewed him to ensure an appropriate diagnosis.
[16] Womack's mail order business, Guild Book Service, started in 1964, distributed a regular bulletin to members with reviews of selections.
Soon after, it became a publishing house in its own right, reprinting gay-themed literature from years past as well as original works, most notably Samuel Steward's 1966 erotic novel $TUD.
This was partly due to a shifting legal climate following the court victory of DSI Sales of Minneapolis, which emboldened publishers of gay magazines and books.
[19] Through the 1960s and 1970s, Womack ran his businesses through partners and subordinates, such as J. J. Proferes (also owner of DC's Metropole Cinema), Henry Pryba, and Raymond Pechin.
Phil Andros) met H. Lynn Womack in New York to discuss the publication of a collection of short stories that he had been working on.
Womack retaliated by immediately having the unbound books in his warehouse bound, but instead of selling or distributing them to bookstores, had them remaindered which meant that Steward would never earn any royalties.