Poe's financial problems started when he went to the University of Virginia in 1826. He had no money of his own, and his foster father, John Allan, only gave him about a third of what he needed for a year of education. Poe decided to earn money by gambling leading to a large debt that John Allan refused to pay in addition he refused to pay for further education. Little information regarding this debt can be found afterward, but Poe joined the US Army under an assumed name the following year.
Believe it or not, authors were not paid much at all in the early part of the 19th century. Most authors of the time were already wealthy or had benefactors. International copyright law was basically nonexistent, so Poe never earned a penny for his writing from outside the United States. Also, the copyright laws in the US were either not enforced or were very poor, so Poe never made much, if anything, in royalty fees. Magazine and newspaper companies also paid very poorly for tales and poetry at the time because they basically held a monopoly. The largest sum Poe ever earned for a story was $100 (about $2400 in today's buying power), and that was from a newspaper contest for his story 'The Gold-Bug.' To be fair, another factor was the population was very small in the US at the time (The 1850 Census showed less than 25 million people, and there were only about 7 million when he was born in 1809.), so the audience was small. Even so, Poe's work was not all that popular during his lifetime until maybe the last four years of his life. Poe did not do much better as an editor/critic as his wages were low, he was often fired, and he moved many times. In fact, Poe's income would be considered below poverty level for much of his adult life.
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