Timothy Dexter was born in Maiden, Massachusetts. He had no schooling to speak of and was working as a farm laborer at the age of 8. When he was 16, he became an apprentice to a leather-dresser.
In 1769 he moved to Newburyport, Massachusetts and begun his trade. He was successful enough to attract a wife, a rich widow Elizabeth Frothingham, and buy a big house.
At the end of the American War of Independence he bought large amounts of European currencies that were worthless at the time. When trade connections resumed, he had amassed a fortune. He built two ships and begun an export business to West Indies and to Europe.
Because he was basically uneducated, his business sense was peculiar but extremely lucky. Somebody inspired him to send warming pans for sale to West Indies, a tropical area. His captain sold them as ladles for local molasses industry and made a good profit. Next Dexter sent wool mittens to the same place. Asian merchants bought them for export to Siberia.
His next venture was selling coal to Newcastle, which should have been a sure failure. His ships happened to arrive in the time of a coalminer's strike and potential customers were actually desperate.
He also exported bibles to East Indies and stray cats to Caribbean islands and again made a profit. He also hoarded whalebone by mistake but ended up selling them as a support material for corsets.
New England high society could hardly contain their dislike for this ignorant but newly-rich upstart and refused to socialize with him. Dexter decided to buy a huge house in Newburyport from Nathaniel Tracy, a local socialite and tried to emulate them but did not attract any sympathy. His relationship with his "nagging" wife, daughter and son were not particularly good, either.
Dexter bought a huge estate from Chester, New Hampshire, and somehow acquired a peerage. He also bought a new house in Newburyport and decorated it with minarets, a golden eagle on the top of the cupola, mausoleum for himself and a garden of 40 wooden statues of famous men, including George Washington, William Pitt, Napoleon Bonaparte, Thomas Jefferson and of course, himself. It had an inscription I am the first in the East, the first in the West, and the greatest philosopher in the Western World. People flocked to gawk at this collection.
Dexter also had his own way with household staff. He had a black and protective housekeeper called Lucy, who he claimed to be a daughter of an African prince. Other servants included a large idiot, a fortune teller and "poet laureate" Jonathan Plummer.
At the age of 50 he decided to write a book about himself - A Pickle for the Knowing Ones or Plain Truth in a Homespun Dress. He wrote about himself and complained about politicians, clergy and his wife. Since he had never learned to spell, the book had no commass or full stops and capital letters were sprinkled all over the place. At first he handed it out for free but it rapidly became popular and ran into eight editions in total. When people complained that it was hard to read, for the second edition he added an extra page of - punctuation marks.
One day he begun to wonder what people would say about him when he died. He proceeded to announce his death and prepare a burial. About 3000 people appeared for the wake. However, Dexter's wife refused to cry for his passing and so he decided not to appear to his guests at all. Timothy Dexter died for real in 1806.
Dexter's house became a hotel, then a library. Storm ruined most of his statues and the rest were sold or incinerated. Only his "littel book" remains to this day.