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The bizarre tale of Timothy Dexter

So everyone's heard of self-made millionaires, right? But have you heard about Timothy Dexter, the luckiest businessman of the 18th century? Dude was an uneducated farm boy who married a wealthy widow and 'invested' in pure nonsense. By pure chance, he made a fortune by shipping coal to Newcastle, which was like, a major coal mining hub, so totally idiotic. Except, his ships arrived during a miners' strike and he cashed in! He also sent warming pans (used to heat sheets in the cold New England winters) to the West Indies, a place that's pretty much always hot, where they repurposed them as molasses ladles. He was rich and ridiculous, even faked his own death to see how people would react. Spoiler: 3,000 people attended his mock wake and he ended up beating one of the mourners who didn't seem sad enough!

Submitted 12 months ago by historyfreak1987


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While Dexter's financial success is undeniable, attributing it purely to luck might be overly simplistic. It's possible that he had an intuitive grasp of contrarian investing—capitalizing on opportunities precisely because they were overlooked and scoffed at by the conventional wisdom of his time. Either that, or he was insanely lucky—like, lottery-winning lucky.

12 months ago by neo_economist

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That fake funeral is legendary. Imagine being so eccentric that you throw your own funeral just to see how people react, and then get mad when they don't mourn 'properly'. This is next-level trolling before the internet even existed.

12 months ago by prankpatrol999

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Fascinating character, Timothy Dexter! It's interesting to note that he published a book called 'A Pickle for the Knowing Ones' which was full of spelling mistakes and nonsensical ramblings. The man became a writer with no punctuation, and when people criticized him for it, he just put out another edition with a page of punctuation marks and told readers to sprinkle them as they pleased! 😆

12 months ago by WeirdHistoryGeek

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I wish I had an ounce of this guy’s luck on my investments. It's kinda infuriating reading about him just stumbling into fortune after fortune while the rest of us do the research and still lose out. Smh.

12 months ago by unlucky_investor

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This dude sounds like a proper chad. Shipping coal to Newcastle? Big brain time 😂 Guess it goes to show, doesn't matter how stupid it sounds if it works.

12 months ago by eighteenthcenturytroll

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I seriously wonder if there was any method to his madness or it was all just blind luck. Could he actually have been some kind of savant at reading the market? lol. Seems too crazy to be true!

12 months ago by anecdotal_mishap

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Timothy Dexter has gotta be one of the greatest flukes in economic history, no joke. The guy literally had the Midas touch but without a clue. You'd think someone would try to copy his 'strategy' but good luck finding this kind of dumb luck ever again, lmao.

12 months ago by colonialnut87