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Timothy Dexter

Timothy Dexter
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3 minute read
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People say that it’s better to be lucky than good. Nothing embodies the meaning of this more than the story of Timothy Dexter.

Timothy Dexter was a businessman from Massachusetts, born in 1747. His life was a continuous series of mistakes he made, but strangely enough, he was successful. He married a wealthy widow. Not a wrong choice itself, but the high society people she surrounded herself with thought Timothy was stupid and tried to sabotage him with bad advice.

Timothy Dexter’s Achievements

He bought continental currency, despite it being worthless at the time and Timothy having no expertise in currency trading. Its value had depreciated so much that the phrase “not worth a continental” was born after the Revolutionary War. Eventually, the government still paid it off, and Dexter got the first of many fortunate windfalls.

Dexter used this money to start a shipping company, trading with Europe and the West Indies. He bought a lot of warming pans that people in New England used to heat up their beds in the winter. He also had the not so genius idea to sell these to the West Indies, a tropical paradise where the temperature in January dips to the chilling lows of 75F. His shipping captain managed to sell them as ladles for the local molasses industry for a substantial profit.

Other Successful Deals

He later also sent wool mittens to the West Indies. Mittens! Fortunately, some passing Asian traders bought them for trade with Siberia.

People pranked him by telling him to ship coal to Newcastle, a coal mining town in England. This even exists as an old English saying; ‘to ship coal to Newcastle’ meaning to do something useless. He went through with this, and it happened to be during a miners’ strike. More profit for him.

His trusted advisers were telling him this time to sell gloves to the South Sea Islands (modern-day Polynesia). He managed to sell them to the Portuguese, who traded with Asia.

His company shipped Bibles to the East Indies before Christianity became popular in the region. Fortunately, arriving missionaries bought his entire supply.

Timothy Dexter shipped stray cats to the Caribbean, which were sold to fight the rat problems.

He purchased a large amount of whalebone. He sold it for a profit to corset makers just as French corsets became a popular trend.

His Personal Life

Timothy Dexter was just as backwards in his personal life. He would tell visitors that his wife had passed. When saw his wife walking around, he would simply say that what they saw was her ghost. He even faked his own death to see who would attend his funeral, then caned his wife for not appearing devastated enough.

At age 50, he wrote a book about himself called A Pickle for the Knowing Ones or Plain Truth in a Homespun Dress. This strange title gives an accurate taste of what the book was like. It succeeded, despite having no punctuation and random capitalization. In the second of eight printings, he added a page of only punctuation, and told people to “peper and solt it as they plese”.

This writing and much of his business may sound stupid, and it truly is. Just remember, Timothy Dexter was not only stupid, but he was stupid like a fox.

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