In the annals of American business history, there are titans of industry, innovators of commerce, and ruthless empire-builders. And then there’s Timothy Dexter — a man so wildly unqualified for success, it’s almost unfathomable how rich he became.
Born in 1747 in Malden, Massachusetts, Dexter had almost no formal education — and even less common sense — at least by 18th-century standards. A former tanner who married a wealthy widow, Dexter did what any new-money social climber might do: tried to imitate high society without understanding a damn thing about it. The result? A comedy of capitalistic errors that somehow and someway made him completely and totally filthy rich.
The Man Who Beat the Market By Accident
After the Revolutionary War, Dexter bought up loads of vastly depreciated Continental currency — the paper money everyone else treated like toilet paper. But when the government decided to honor it — at a low rate to face value but at a higher rate than he had paid overall — Dexter found himself with a fortune, quite literally for doing the opposite of what all of the “smart” people were doing.
From there, his business ventures took a hard left into even larger lunacy:
He once shipped coal to Newcastle, England — a place famous for its massive coal supply. In fact, a common way to say that something was a waste of time then was to say, “It’s like trying to sell coal to Newcastle.” Dexter apparently took this literally. Everyone laughed, but then the miners went on strike. Profit!
He went on to ship bed-warming pans to the Caribbean, where it’s — well — hotter than Satan’s armpit. Locals didn’t need bedwarmers, but used them in the huge pots there to refine sugar. Profit!
Since he was on a roll in the Caribbean, he shipped mittens to the West Indies. Laughable for sure — until merchants in Siberia bought them. Profit!
So, he sent Bibles to the East Indies, and missionaries happily took them. Profit!
In an era where most fortunes were made through careful planning and ruthless negotiation, Dexter built his empire on miscommunication, misunderstanding, and just plain dumb luck — and it worked!
The Eccentric Lord of Newburyport
Flush with wealth and delusion, Dexter declared himself “Lord Timothy Dexter” and built a gaudy estate in Newburyport, Massachusetts. The property was adorned with statues of George Washington and other American heros, and — naturally — himself. His tomb had already been built and engraved while he was still alive, because subtlety wasn’t his thing.
He once faked his own death just to see who would cry. When his wife didn’t mourn hard enough, he caned her in front of the other mourners. Ope! Grief theater was serious business in his mind, it seems.
And then came his literary “masterpiece” — sort of:
“A Pickle for the Knowing Ones”, a self-published, grammar-optional book filled with rants, complaints, and exactly zero punctuation. Critics laughed. Readers bought it, though! When people complained about the lack of punctuation, he added a second edition that featured an entire page of commas, periods, and semicolons with instructions to “peper and solt it as they plese.” Genius! Eight editions later, he was the genius perhaps.
Legacy of a Lunatic Capitalist
Timothy Dexter died in 1806, still rich, still ridiculous, and still utterly confounding to the world of business. He remains one of America’s most fascinating “what-the-hell?” footnotes to success — a man who succeeded not in spite of his ignorance, but seemingly because of it.
In today’s world of meme stocks, crypto gamblers, and YouTubers who sell you a course before knowing what they are even doing themselves, maybe Dexter was not an idiot after all — just ahead of his time. The original “fake it ‘til you make it” entrepreneur — only he didn’t fake it; he really had no clue what he was doing, and the universe didn’t seem to mind.
Only in America!
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