Timothy Dexter might actually be the luckiest man ever to live. Dexter was a prolific business mam at the dawn of the United States. He was one of the first people in U.S. history to rise from the lower class to the upper class. His business success, however, was entirely a stroke of luck. Few things that he succeeded in can be attributed to his intelligence or business prowess. He made most of his fortune off of tips from contemporaries trying to ruin him. Timothy Dexter, being none the wiser, took these tips and somehow got very lucky with them. This man is eclectic, lucky, and illiterate (but his book sales beg to differ). This is the story of the wild life of Lord Timothy Dexter.
Humble Beginnings
Timothy Dexter was born in the town of Malden, Massachusetts. At the age of eight, he dropped of school to become a farmworker. At 22, he married the then 32-year-old widow Elizabeth Frothingham who had recently inherited her wealthy husband’s estate. This was when Dexter’s life went from plain to extravagant.
Continental Market Bets
During the revolutionary war, the United States government circulated the Continental Currency. The money was worthless, and everyone knew it. Yet, for no apparent reason, Dexter bought the currency off of everyone he could find for fractions of a penny. Over time Timothy had amassed thousands of these worthless notes.
In a stroke of unforeseen luck, after establishing the United States, the decision was made to buy back the currency from the soldiers at one percent of face value. Since Timothy had bought these $10, $20, & $100 notes for fractions of a penny, he made a massive profit from the buy-back program. With the profits, he bought ships and began his empire.
Shipping Useless Goods to Crafty Individuals
Many of the other successful individuals in Timothy’s circle were not fans of the poorly educated millionaire. So, he began receiving business tips from his peers who were attempting to ruin him financially. It started with him shipping bed warmers to the west indies. Of course, the west indies do not need bed warmers given their tropical climate. But, wise sales work from his ship captain led the locals to believe the devices were molasses scoopers and sold out.
This would become a pattern for Dexter’s business endeavors. First, he would get advice from a peer who had ulterior motives to destroy Dexter’s empire. Then, regardless of how poor the advice was, Timothy would take it and invest vast sums of money into the venture. Then, to everyone’s surprise, it would somehow pay off, leaving Timothy Dexter even more prosperous than before.
Lord Timothy Dexter and His Royal Estate
Timothy was rolling in the profits. Like many who achieved great wealth, he used that to build a mansion worthy of a king. The luxury of his estate sprawled many acres and included a fabulous house and a massive garden complete with 40 statues of esteemed individuals, including himself, of course. However, Timothy seemed to be the only person who thought the estate was something worth admiring. It was so hideous that his wife chose to move out, not due to any marital issues, but simply since she hated the house.
Timothy Dexter Throws a Funeral
One day, Dexter wondered what the people in his life thought of him. So he built a mausoleum, faked his death, and planned a funeral so he could see everyone’s reaction. His family was in on the ruse and prepared for the event. When it came time for the funeral, 3000 locals turned up. But, much to his dismay, Timothy’s wife did not act the part well enough. He then confronted her in the middle of the wake, revealing that it was all a lie.
Dexter Becomes a Philosopher
Dexter began filling his mind with various philosophies and felt the need to teach his wisdom to the masses. So he penned a book titled A Pickle For the Knowing Ones. Unfortunately, his book was utterly incoherent. It was wrought with spelling and grammar errors and didn’t include any punctuation. Critics addressed the book’s lack of punctuation, so Dexter had an entire page of various marks and told readers to “salt and pepper” them as they saw fit.
Conclusion
Timothy Dexter may well be one of the first rags to riches stories in United States history. He is undoubtedly one of the luckiest people ever to live. He had a sort of mythic luck go before all of his endeavors. His intrigue only outmatched his fortune. The man’s home, lifestyle, and writing career leave people stunned to this day. Find out more about Timothy Dexter in this episode of Things I Learned Last Night.
Things I Learned Last Night is an educational comedy podcast where best friends Jaron Myers and Tim Stone talk about random topics and have fun all along the way. If you like learning, and laughing a whole lot while you do, then you’ll love TILLN. Watch or listen to this episode right now!
This episode of the Things I Learned Last Night Podcast was filmed live with an audience at the Rino in Kansas City, MO on October 30th, 2021. Thank you to all who came out, watched online, and worked to make it happen!
Sources
New England Historical Soceity
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