Day 583 - The utility of acting the fool - https://golifelog.com/posts/the-utility-of-acting-the-fool-1659753063384

I don’t know why but I love and get inspired by stories like this – unassuming ‘fools’ who are actually smarter than they look, know how to game the system, and actually go on to make it big:

Timothy Dexter and “the utility of acting the fool”
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"At the end of the American Revolutionary War, he purchased large amounts of depreciated Continental currency that was worthless at the time. At the war’s end, the U.S. government made good on its notes at one percent of face value, while Massachusetts paid its own notes at par. His investment enabled him to amass a considerable profit. He built two ships and began an export business to the West Indies and Europe.

Because he was largely uneducated, his business sense was considered peculiar. He was advised to send bed warmers—used to heat beds in the cold New England winters—for resale in the West Indies, a tropical area. This advice was a deliberate ploy by rivals to bankrupt him. His ship’s captain sold them as ladles to the local molasses industry and made a handsome profit. Next, Dexter sent wool mittens to the same place, where Asian merchants bought them for export to Siberia.

People jokingly told him to “ship coal to Newcastle”. Fortuitously, he did so during a Newcastle miners’ strike, and his cargo was sold at a premium. On another occasion, practical jokers told him he could make money by shipping gloves to the South Sea Islands. His ships arrived there in time to sell the gloves to Portuguese boats on their way to China.

He exported Bibles to the East Indies and stray cats to Caribbean islands and again made a profit; Eastern missionaries were in need of the Bibles and the Caribbean welcomed a solution to rat infestation. He also hoarded whalebones by mistake, but ended up selling them profitably as corset stays.

While subject to ridicule, Dexter’s boasting makes it clear that he understood the value of cornering the market on goods that others did not see as valuable and the utility of “acting the fool”.

- Source: Wikipedia

What’s interesting is how he seems to take reference from others to gauge what’s not valuable, what’s uncommon, what’s stupid, and go find opportunities in those areas because there would be no competition. Nobody’s ‘stupid’ enough to venture there, but that’s exactly where the opportunity is!

It’s almost like a teachable moment here for me.

This guy’s an opportunistic trickster. I set an identity-based goal (https://golifelog.com/posts/identity-based-goals-1634279678058) like this back in Oct last year, and he has these traits:

• Has too much fun, oftentimes at the disapproval of others
• Takes nothing too seriously, even when others are serious
• Keen sense of asymmetric chances to win big
• Acts on asymmetry and actually wins
• Doing random is second nature

Mr Dexter definitely check off everything on that list! And probably more. This is something I really wish to be able to embody, but in software/internet business.

So… what are some problem spaces that most internet entrepreneurs would see as stupid to venture into?

What’s the internet equivalent of selling ice to Eskimos?

How do I corner “the market on [internet] goods that others did not see as valuable”?

I tried brainstorming a bit on my own but drew blanks. Absolutely no ideas. Obviously this is an area where I’m totally cold.

Much to learn, and to look out for!