A lucky devil, dumb as a rock — that’s Timothy Dexter, the 18th-century investor who turned every bad idea into a jackpot. He was a man whose business strategy looked like madness — until it worked. Again and again.
Timothy Dexter was an eccentric 18th-century investor whose life seemed like a series of bad ideas that somehow turned into brilliant successes. He wasn’t known for intelligence, but his uncanny luck made him rich and infamous.
One of his earliest financial moves was spending his wife’s fortune — she was a wealthy widow — on nearly worthless Continental currency after the American Revolution. In 1781, it took a thousand of these bills to equal a single dollar. Nine years later, in 1790, the U.S. government agreed to exchange them for government bonds at a rate of 100 to 1. Dexter ended up making ten times what he had spent. Imagine the long years of ridicule he must’ve endured — and the vindication that followed.
With the money he gained, he followed sarcastic advice from someone and sent bed warmers — pans with lids and wooden handles used to heat beds — to the Caribbean. Instead of failing, the locals used them as scoops for molasses and bought them in bulk. Dexter profited once again. Next, he sent mittens to the Bahamas. It sounded ridiculous, but traders there resold them to Russia alongside shipments of rum, turning the seemingly foolish idea into another win.
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At one point, Dexter purchased all the whalebone he could find in Boston. Just then, men’s corsets made from whalebone became the fashion rage in Europe. His timing was flawless.
His rivals, annoyed by his success, dared him to send coal to Newcastle — the heart of coal mining in England. He took the bait, and his shipment arrived during a miner’s strike. With local supply frozen, his coal sold at premium prices.
Perhaps his strangest venture involved cats. His hometown had a problem with strays, so Dexter rounded them up and sent them to the West Indies, where there was a rat infestation. Yet again, he turned a local nuisance into profit.
As he aged, Dexter’s behavior became even more bizarre. He declared himself a nobleman, took on the title of deer warden in a town where deer hadn’t been seen in two decades, and authored a memoir titled Nonsense for the Wise. The book had no punctuation at all. When readers complained, he responded by printing a second edition with a single page full of commas, telling people to insert them wherever they liked.
Timothy Dexter may have lacked sense, but his life proved that success doesn’t always come from logic or planning. Sometimes, it’s just a wild mix of timing, risk, and outrageous luck.
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