Timothy Dexter (1747-1806) was an American businessman noted for his writing and eccentricity.
At the end of the American Revolutionary War, he bought large amounts of depreciated Continental currency that was worthless at the time. At war's end, the U.S. government made good on its notes at one percent of face value, while Massachusetts paid its own notes at par. His arbitrage enabled him to amass a considerable profit. He built two ships and began an export business to the West Indies and Europe.
Because he was largely uneducated, his business sense was considered peculiar. He was advised to send bed warmers—used to heat beds in the cold New England winters—for resale in the West Indies, a tropical area. This advice was a deliberate ploy by rivals to bankrupt him. His ship's captain sold them as ladles to the local molasses industry and made a handsome profit. Next, Dexter sent wool mittens to the same place, where Asian merchants bought them for export to Siberia.
People jokingly told him to "ship coal to Newcastle". Fortuitously, he did so during a Newcastle miners' strike, and his cargo was sold at a premium. On another occasion, practical jokers told him he could make money by shipping gloves to the South Sea Islands. His ships arrived there in time to sell the gloves to Portuguese boats on their way to China.
He exported Bibles to the East Indies and stray cats to Caribbean islands and again made a profit; Eastern missionaries were in need of the Bibles and the Caribbean welcomed a solution to rat infestation. He also hoarded whalebones by mistake, but ended up selling them profitably as corset stays.
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At age 50, Dexter authored the book A Pickle for the Knowing Ones, in which he complained about politicians, the clergy, and his wife. The book contains 8,847 words and 33,864 letters, but without any punctuation and with unorthodox spelling and capitalization. One section begins:
Ime the first Lord in the younited States of A mercary Now of Newburyport it is the voise of the peopel and I cant Help it and so Let it goue
The first edition was self-published in Salem, Massachusetts in 1802. Dexter initially distributed his book for free, but it became popular and was reprinted eight times. The second edition was printed in Newburyport in 1805. In the second edition, Dexter responded to complaints about the book's lack of punctuation by adding an extra page of 11 lines of punctuation marks with the instruction that printers and readers could insert them wherever needed—or, in his words, "thay may peper and solt it as they plese".
I think that's more funny than Trump printing out and autographing tweets.