In a world obsessed with optimisation and five-year forecasts, there’s something deeply satisfying about success that arrives by mistake. Especially the kind that should have ended in disaster, but somehow didn’t.

Take Aspartame, for example. That sweet little zero-calorie miracle was never meant to flavour your diet soda. It started out as an experimental anti-ulcer drug. A student working in the lab at the time misunderstood an instruction to “test” the compound, and for reasons best left unexplored, decided to lick it off his finger. Instead of dropping dead, our hapless hero discovered that the substance was remarkably sweet. And just like that, Aspartame was born – not with precision or peer review, but with a lucky lapse in judgement.

History is full of these kinds of people; the ones who bumble their way into brilliance. But few ever did it with the level of confusion, confidence, and outright chaos as Timothy Dexter, a semi-literate, self-proclaimed philosopher who built a fortune by ignoring common sense and making every wrong move feel like a masterstroke.

Usually in this column, I try to tell stories that carry some kind of useful insight – a moral, a principle, perhaps even a profound takeaway about the nature of success or human behaviour.

This isn’t one of those stories.

What follows contains no useful advice whatsoever. I don’t recommend emulating a single thing you’re about to read. But I do suggest reading it out loud at your next family dinner. Because if ever there was a true tale that reads like fiction, it’s the saga of Timothy Dexter.

A quick note on facts and claims

In addition to his accidental business brilliance, Timothy Dexter also fancied himself a writer. This, as it turns out, is both a blessing and a bit of a problem.

On the upside, we have a firsthand account of his bizarre life, which is rare for an 18th-century eccentric. On the downside, his writing was a chaotic mess: no punctuation, erratic spelling, and endless self-praise. Historians still hotly debate whether he was joking, delusional, or both.

Author John P. Marquand tried to make sense of it all in Timothy Dexter Revisited, one of the few serious attempts to separate fact from fiction. Still, even with Marquand’s help, we’re left with a picture of a man who may have invented himself as much as he invented his fortune. What follows is therefore the story as far as we know and believe to be reasonably true. 

A frothy investment

Timothy Dexter wasn’t exactly what you’d call formally educated; in fact, his schooling ended almost before it began. By eight, he was labouring on a farm and by fourteen, he was knee-deep in hides and animal fat as a tanner’s apprentice. It was, by all accounts, an unglamorous start. But Dexter had two things going for him: blind optimism and an unshakable belief that he was destined for greatness. That, and a very fortunate marriage. In his early twenties, he wed a wealthy widow named Elizabeth Frothingham and used her fortune to set up a leather goods shop in Newburyport, Massachusetts.

Dexter did well enough from his shop to start entertaining bigger, stranger ideas. He began speculating, a word that in his case meant throwing money at wildly impractical ventures with the swagger of a man who definitely hadn’t done the maths.

One of his earliest gambles was buying up mountains of Continental currency. This was the paper money printed by the Continental Congress during the American Revolution. It had been so overproduced that, by the end of the war, it was practically worthless. Most people wouldn’t have accepted it as wallpaper. But Dexter, convinced he saw something others didn’t (a recurring theme), bought it by the cartload for pennies. Literally – pennies on the dollar.

Despite the fact that there were no indications that this might happen, Dexter reasoned that the government might one day change its mind and make the money redeemable again. And then in the 1790s, that exact thing happened. The newly minted US Constitution included a provision that allowed holders of Continental currency to trade it in for government bonds. And just like that, the man who had hoarded worthless paper like a magpie with a head injury became outrageously, accidentally rich.

Dexter’s critics (and there were many) called it dumb luck. And they weren’t wrong. But Dexter, ever the opportunist, took it as divine confirmation that he was a financial genius. Which was just the confidence boost he needed to start speculating on a much more daring scale.

First America, then the world

Flush with cash and positively dripping with confidence, Timothy Dexter did what any newly rich eccentric with delusions of genius might do: he built himself a small fleet of ships and launched an export business. This, despite the small logistical hiccup of being functionally illiterate and knowing next to nothing about international trade.

Instinct can only take you so far, especially when you’re surrounded by people actively trying to ruin you. You see, Dexter’s circle of “advisors” were less mentors and more saboteurs. Many were upper-crust merchants who resented his sudden, unearned rise and thought it would be hilarious to feed him terrible business ideas and watch him self-destruct. What they failed to account for, tragically, was Dexter’s supernatural ability to fail upwards.

Let’s take the time they told him to ship coal to Newcastle, a city famous for its massive coal reserves. Dexter sent a ship anyway, arrived during a miners’ strike, and sold out at a profit. Then came the bedwarming pans to the West Indies, where no one needed to heat their beds – so he rebranded them as molasses ladles and sold them to sugar plantations. Gloves to the South Sea Islands? Scooped up by Portuguese traders en route to China. Bibles to the East Indies? Bought by missionaries. Stray cats to the Caribbean? Solved a rat problem in a cinch.

Even his mistakes were profitable. He once hoarded whalebones, thinking they might be valuable for reasons unknown. Turns out, whalebone was soon in high demand for its use in corset stays. Women across America were cinching their waists with the remnants of Dexter’s latest blunder.

The inevitable autobiography

In 1802, Timothy Dexter decided the world needed his thoughts in print. The result was a self-published gem titled A Pickle for the Knowing Ones; or, Plain Truths in a Homespun Dress – a book that was part autobiography, part rant, and entirely unhinged. Inside, Dexter boasted shamelessly about his successes, aired grievances against his wife and various enemies, and did so with zero punctuation, chaotic spelling, and the kind of random capitalisation that suggests he was fighting the alphabet in hand-to-hand combat.

One baffled critic later described it as “a jumble of letters promiscuously gathered together,” which feels generous. Dexter gave the first edition away for free in Salem, Massachusetts, where it quickly caught on. The public, ever fond of a trainwreck, kept asking for more. The book was reprinted eight times, making it an accidental bestseller.

By the second edition, Dexter responded to critics’ demands for punctuation by adding an entire page filled with stray punctuation marks (just lines of dots, commas, question marks and the like) with instructions that readers could “peper and solt it as they plese.” Truly, a man ahead of his time in crowdsourced editing.

When Dexter died in 1806, his estate was valued at $35,027, which translates to roughly $922,957 in today’s money assuming you just increase it by inflation. While that’s not exactly a fortune (going by the state of his mansion and its grounds, Dexter was the kind of man who believed in spending his money), it’s still not bad for someone who wrote like a cat walking across a keyboard.

Was Timothy Dexter a madman, or a master of accidental strategy, or some type of unconventional business savant?

He referred to himself as “the greatest philosopher in the known world.” Historians tend to disagree. But what can’t be denied is this: Dexter made a good living by leaning into the absurd, the impossible, and the unadvisable – and somehow, it just kept working.

He wasn’t educated, but he understood the art of the pivot. He wasn’t a writer, but he sold books. He wasn’t respected, but he was remembered.

How many of his peers could claim the same?

About the author: Dominique Olivier

Dominique Olivier is the founder of human.writer, where she uses her love of storytelling and ideation to help brands solve problems.

She is a weekly columnist in Ghost Mail and collaborates with The Finance Ghost on Ghost Mail Weekender, a Sunday publication designed to help you be more interesting. She now also writes a regular column for Daily Maverick.

Dominique can be reached on LinkedIn here.