A Life Lived ArtfullWhat Timothy Dexter’s Blind Luck (or Crazy Genius) Teaches Us About Risk and Creativity

There are, it seems only two logical possibilities, either Timothy Dexter was a time traveler from the year 2020 who had 'Quantum leaped' into the 18th century or he, along with every single one of his Irish forebearers had been born with a lucky 'four leaf' clover birthmark. Nothing else could explain his life surely?

Read on and you decide which it is...

Introduction

Most people fade into obscurity shortly after their time on Earth ends, but not Timothy Dexter. Born in 1747 in colonial Massachusetts, Dexter remains one of the most unforgettable figures in American history—not for his intellect, moral contributions, or leadership, but for his baffling knack for turning harebrained ideas into gold.

Seriously imagine Baldrick from the British TV show 'Blackadder' 'Cunning plans' actually working and you get the idea...

This is the story of a man whose wild business ventures should have ended in ruin from just the thought alone but instead made him fabulously wealthy.

Was Dexter a lucky fool, or did he possess a bizarre genius for seeing opportunities others couldn’t? More importantly, what can his improbable story teach us about taking risks and embracing a creative life?

The Early Years: From Farmhand to Wannabe Gentleman

Timothy Dexter’s life didn’t start auspiciously. Born to Irish immigrants, Dexter was forced to drop out of school at age eight to work as an indentured servant on a nearby farm. For eight grueling years, he toiled in exchange for basic sustenance, eventually gaining his freedom and moving to Boston to work as a tanner.

Though he found moderate success in his trade, Dexter’s life took a dramatic turn when he married Elizabeth Frothingham, a wealthy widow.

This marriage launched him into the affluent circles of Charlestown, Massachusetts. Yet Dexter, with his coarse manners and lack of education, was far from a welcome addition to the elite.

Instead of retreating, he doubled down on trying to fit in, copying their manners, fashion, and even business ventures—with some hilariously disastrous results.

Foolish Ventures or Genius Moves? Dexter’s Business Triumphs

Here are just a few of Dexter's foolish ventures that turned out to be genius.

The Continental Currency Gambit

During the Revolutionary War, the Continental Congress issued its first official currency. Due to overprinting and widespread counterfeiting, the value of Continental Currency plummeted to near worthlessness.

Most people avoided it like the plague, but Dexter saw an opportunity—or perhaps just followed the crowd. You see the in-crowd he so wanted to accept him had been buying token amounts of the Continental currency as a 'good citizenship' show of support for the aligning economy.

Desperate to gain favor with his elite neighbors, he bought Continental Currency in vast quantities, eventually amassing about 20% of all notes in circulation.

This should have bankrupted him. Instead in an extraordinary bit of good luck, Alexander Hamilton’s financial reforms in 1790 allowed Continental Currency to be redeemed for Treasury bonds at 1% of their face value. Dexter, who had bought the notes for fractions of a penny, became astoundingly wealthy overnight.

Coal to Newcastle: A Fool’s Errand?

The phrase "selling coal to Newcastle" signifies a pointless endeavor since Newcastle was a coal-mining hub. Dexter, either unaware of the idiom or undeterred by its implications, loaded a ship with coal and sent it to Newcastle. By sheer coincidence, a miners' strike had left the town short of coal when Dexter’s shipment arrived, allowing him to sell it at an enormous profit.

Bed Warmers in the Tropics

In one of the most infamous episodes of his career, Dexter shipped 40,000 brass bed warmers to the West Indies, a region with no need for such items in its balmy climate. However, the locals found a use for them as large ladles for molasses production. Dexter once again turned a profit of over 70% on what seemed like a ludicrous venture.

Whalebone and Corsets

After misinterpreting a request, Dexter accidentally purchased 350 tons of whalebone. Initially, the investment seemed disastrous. But soon after, whalebone became a sought-after material for corsets, allowing him to corner the market and sell his stock at enormous gains.

Bibles and Cats

Dexter shipped Bibles to the Caribbean, a region with little initial demand for them. His sailors spread rumors that owning a Bible would save one’s soul, sparking a buying frenzy. Later, when faced with a surplus of stray cats in Newburyport, Dexter exported them to the rat-infested warehouses of the Caribbean, marketing them as expert “mousers.” Both ventures yielded significant profits.

The Madman with a Mansion

Flush with cash, Dexter built an extravagant mansion in Newburyport, complete with 40 statues of famous men, including one of himself bearing the inscription: “I am the first in the East, the first in the West, and the greatest philosopher in the Western world.”

He styled himself as "Lord Dexter" and even hired a poet to write glowing verses about him. His ego knew no bounds, yet his behavior grew increasingly erratic.

In one infamous episode, Dexter faked his own death to gauge how much he was loved, only to emerge from hiding mid-funeral and berate his wife for not crying enough.

Literary Infamy: A Pickle for the Knowing Ones

Determined to secure his legacy, Dexter penned an autobiography titled A Pickle for the Knowing Ones. The first edition was nearly incomprehensible, written without punctuation and riddled with spelling errors. In response to criticism, Dexter added an appendix in the second edition consisting entirely of punctuation marks, inviting readers to “distribute them as they please.”

Despite its poor quality, the book became a bizarre sensation, further cementing Dexter’s place in history as a madman who somehow struck gold in every endeavor.

Lessons from a Life of Risk and Creativity

What can we learn from Timothy Dexter’s wild ride through life? Here are some key takeaways:

1. Embrace Risk Dexter’s ventures were often ill-informed and poorly planned, yet his willingness to take bold risks opened doors to unimagined opportunities.

2. Leverage Unconventional Thinking His success in selling coal to Newcastle and bed warmers to the tropics demonstrates the value of finding unique angles in any situation.

3. Resilience in the Face of Ridicule Despite being mocked relentlessly, Dexter forged ahead, proving that persistence can sometimes beat preparation.

4. Luck Favors the Bold Dexter’s story reminds us that fortune often smiles on those who dare to act, even when the odds seem impossible.

Conclusion

Timothy Dexter’s life defies conventional wisdom. Was he a fool blessed with extraordinary luck, or a hidden genius who saw value where others didn’t? Whatever the answer, his story is a testament to the power of audacity, creativity, and the sheer unpredictability of life.

In a world that often rewards conformity, Dexter reminds us that there’s room for the eccentric, the risk-taker, and the dreamer. Sometimes, success isn’t about following the rules—it’s about rewriting them altogether.

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See you when I'm back from my trip selling snow to Eskimos ala Timothy Dexter... :-)