Failing Upward: The Story of Timothy Dexter

The biggest lie in American Society is that a can-do attitude and go-getting spirit will lead to success. That America is a meritocracy, that anyone who works hard enough can achieve anything they want. And while this is true to an extent, luck also plays a huge role in success. Anyone who tells you otherwise is lying. Timothy Dexter is a perfect example of this. He was born into poverty but managed to make himself a millionaire through a whole lot of good luck.

Mr. Dexter was by no means regarded as an intelligent man. His education was essentially nonexistent, and his business sense was seen as abysmal, to say the least, but regardless of his seemingly significant shortcomings, he managed to become wealthy. No one in their right mind would say that Mr. Dexter's success was due to merit, that his hard work eventually paid off. While it's true that he did work hard, luck was the determinative factor in his success.

Mr. Dexter dropped out of school to become a farm worker when he was eight years old, likely due to necessity. He then apprenticed under a tanner, which did not garner him much of a living. He married into wealth, which he then foolishly invested in various ventures.

His first notable investment was buying significant amounts of Continental currency, which was depreciating quickly toward the end of the Revolutionary war. However, as luck would have it, the newly formed United States made good on the notes at 1%, but Massachusetts made good on their notes dollar for dollar. Think of that guy you know that through a few hundred dollars at Bitcoin early on and now has millions. that is the level of lucky timing and positioning Mr. Dexter had. He sent bedwarmers to the West Indies on the suggestion of a contemporary who was likely trying to financially ruin and make a fool of him, but they sold at a premium not because there was a need to warm beds in a tropical climate, but because the molasses industries thought they were, or at least would adequately serve as, ladles for the molasses.

Later he shipped coal to Newcastle, a mining town, on the suggestion of others (likely as a joke). but the timing was again extremely lucky. At the time the coal reached Newcastle, the local miners has been on a strike, which meant that the coal was sold at a premium. He sent stray cats to the Caribbean, which were sold as a result of a rat infestation. He purchased whalebones in error but again profited by selling them to the corset industry.

All of these lucky events allowed Timothy Dexter to amass a fortune, which he then used to purchase land and build himself a grand estate. He wrote a book called A Pickle for the Knowing Ones or Plain Truths in a Homespun Dress, which was panned by critics but nonetheless made him popular among the general public.

When he died, his estate was valued at more than $800,000.00 in present value.

It is practically impossible for Mr. Dexter to have been simply a lucky fool. He made risky investments that paid off, but that luck was also likely due to understanding that cornering a market, any market, can be profitable. It is also possible that he was not as big of a fool as he was made out to be by his contemporaries. He may have simply played the role of the fool so that others underestimated him. We may never know. So remember, next time you're feeling down about your lack of success, that it's not just hard work that gets you ahead in life, it's also luck. And if you don't believe me, just ask Timothy Dexter.