May I present
"Lord" Timothy Dexter (1748-1806):

The word "eccentric" is used to describe him, but I would use "shrewd," too.
The man had no formal education and was trained to be a leather-maker, but he managed to marry a rich widow that was 10 years older than him in 1770. Here's where his "shrewdness" comes into play.
During the American Revolution, he bought Continental currency in bulk. The money was about as useful as toilet paper.
When the war ended in America's favor, the new U.S. Government's monetary notes (as well as Massachusetts', as the states had their own banknotes at the time) were set at one percent of the face value. Dexter became a very wealthy man as a result.
But, his fortunes do not stop here.
With his newfound wealth, he entered the shipping industry by building two ships: one to be used to ship cargo in the West Indies and the other to Europe. Since Dexter did not have any real business education, his competitors and detractors tried fucking with him.
Under the pretext of giving him sound business advice, they advised him to ship bed warmers and wool mittens to the West Indies.

Bed warmers (as seen above) do exactly as described and were perfect for keeping cozy during cold, winter nights.
Wool mittens were great for keeping hands from freezing, too.
Only one problem: The West Indies is a tropical region.
What looked to be a financial disaster waiting to happen turned out to be unexpectedly fortuitous: His ship captain sold the bed warmers as ladles to molasses makers and the wool mittens to merchants heading Siberia. As such, Dexter made a profit.
This did not mean Dexter earned respect. He was trollled by his detractors once more to send coal to Newcastle, England. A Britbong would more than likely inform us that Newcastle is a mining town, so this would have been a stupid venture. Yet, Dexter did so. The timing could not have been more perfect, too: there was a miner's strike in Newcastle occurring at the same time. Dexter made a killing.
Such instances kept happening:
- The people of Newburyport, Massachusetts, wanted to cull their stray cats, Dexter offered to pay for the cats and ended up shipping them to The Caribbean, which was dealing with a rat infestation.
- Dexter exported Bibles to the East Indies, where missionaries gladly took them as they were in need of them.
- Dexter wanted to corner the whalebone market and hoarded many. He managed to make a profit when corset stays were the vogue in French fashion (as well as hoop skirts).
- Once more, Dexter shipped gloves but to the Polynesian Islands this time. His traders were able to sell the gloves to Portuguese traders that were headed to China.
Despite all the financial successes, he was never respected in Newburyport's High Society.
Probably due to his eccentric antics.
He declared himself a Lord - "The Earl of Chester", after a stay at the merchant town, despite there being no aristocracy in the United States (officially).
He told visitors that he was haunted by the spirit of his wife, despite the fact his wife was very much alive.
He once faked his own death to see how people would react and 3,000 people came to the funeral service. He ended the ruse when he caned his wife for not sufficiently mourning his death.

Dexter developed a bit of a drinking problem (always a recipe for disaster) and was a womanizer, which led him into a fight with a lawyer. The lawyer won.
Dexter also kept company with "fellow eccentrics" (lolcows) such as Madame Hooper, a woman with a double set of teeth and a pet chicken, and fishmonger Jonathan Plummer (this guy can be described as a coomer).
Dexter's children did not inherit their father's stupid good luck.
His son, Samuel, also developed a drinking problem despite Lord Dexter's attempts to turn his son into "an educated gentleman."
Samuel Dexter also convinced his father to give him a ship to sell cargo in England. Instead, Samuel blew all of the profits on the gambling tables.
Timothy Dexter's daughter, Nancy, married a Yale student that had little cash. Well, her husband abused her and the marriage failed. Afterward, Nancy also turned to drinking and became a shut-in after coming back home.
Lord Dexter's Estate was just as eccentric as the man who inhabited it:

As seen in the picture above, there are 40 wooden statues of George Washington, William Pitt, Napoleon Bonaparte, Thomas Jefferson, Louis XVI, Toussaint Louverture, and John Hancock among others. Of course, there is one of himself there, too, which was inscribed with "I am the first in the East, the first in the West, and the greatest philosopher in the Western World." Along with his outdoor "Hall of Statues," Dexter also had a golden eagle on the top of the cupola of the roof of the Dexter House and a mausoleum built.
But perhaps one of his lasting legacies is his 25-page autobiography,
A Pickle for the Knowing Ones. Since Dexter never received a proper education, the book is filled with grammatical errors and NO PUNCTUATION. The latter would be a particular complaint from those that read the book, which illicited a unique response from Dexter. In the second edition of the book, Dexter added a page that had 13 lines of punctuation marks with instructions for readers (and printers) to "peper and solt it as they plese."
When he passed away on October 23, 1806, his body was not entombed in the mausoleum that he built for himself.
Instead, he was buried in a simple grave at Old Hill Burying Ground in Newburyport, Massachusetts.
The tombstone doesn't really do much to properly convey Timothy Dexter's life, either.
His estate became a hotel at some point and the the only surviving statue was William Pitt's.
On August 15, 1988, house painters accidentally caused the belvedere to crash through the house (this is after they tried burning the paint under the eaves, causing a fire!). $1,000,000 later, the house was rebuilt.
Thus ends the story of "Lord" Timothy Dexter.