The story of the luckiest dumb person: Timothy Dexter (Or how one guy sold winter gloves in the Caribbean)

If there were ever a competition to see who is the dumbest person to have succeeded, Timothy Dexter would win it hands down. You won’t read more than a footnote in most history books about him. But he was the luckiest person who ever lived. Did one dumb thing after another. And yet prospered.

Dexter yearned for his peers’ respect. And did some crazy things because of it.

Crazy luck #1: 

In 1775, the 13 American colonies went to war with the UK. To fund the war, American Congress started printing “Continental Currency.” But they overprinted it. To the tune of $241 million! The currency flooded the market and became all but worthless. No one would accept it. When the war veterans started coming back, American colonies paid them in the worthless Continental currency. And the veterans found themselves destitute. 

To help the veterans out, leaders like John Hancock asked people to start buying the currency. And they themselves bought a little bit too. But almost no one else did. No one else except our Dexter.

Timothy Dexter not only spent all his money buying the Continental currency, but spent his wife’s fortune too. Why? Because a great person like John Hancock supported it.

The currency remained worthless. But in 1788, after ratifying the US constitution, the Congress declared that they would buy back these old Continental Currency at 1% of their value. Dexter, who had bought it at a much much cheaper rate, suddenly found he was rich beyond his wildest dreams!

He bought 2 shipping vessels with his profits and bought a mansion and moved to a place where rich folks lived.

Crazy luck #2: 

Figuring out that Dexter would do anything to gain his peers’ acceptance, one of his rich neighbours recommended that Dexter should ship warming pans in the West Indies and sell them there. West Indies is hot and humid. Why would anyone need pans that were used to warm beds in the winter? But yet they did! The West Indians found that these pans made great tools to stir molasses. The sugar plantation owners bought all the pans for 79% higher price!

Crazy luck #3: 

The same trick was tried again, and this time Dexter shipped winter woolen gloves to equatorial Polynesian islands. And again luck helped him out. When Dexter’s ship landed in hot Polynesia, they were just in time to sell all their gloves to a Portuguese ship sailing to Siberia!

Crazy luck #4: 

Someone else tried to take advantage of Dexter’s naivety again. And told him he should sell coal to Newcastle. Unknown to Dexter, Newcastle was one of the leading producers of coal in the world at that time! But luckily for Dexter, when his ships landed there, there was a strike at the coal mines! Newcastle factories bought his coal at a premium!

Crazy luck #5: 

Dexter heard of a few traders who would corner the market for a particular product, jack its prices up, and make insane profits. So he tried to do the same thing. Unfortunately, he cornered the market for whalebone. Why? Because he could. No one else wanted whalebone. So Dexter bought 340 tons of it, and monopolized the market. Wouldn’t you know it: next year, corsets started coming into fashion. Whalebones helped in making sturdy corsets! 

Without a doubt, Timothy Dexter was the luckiest person to ever live. But is there anything we can learn from him? Can we even try to replicate his luck?

Being lucky without being dumb

Timothy Dexter spent his life pleasing his peers. And that got him to do things that no one else did! 5 times in his life, he was correct when no one else was. And 5 times in his life, he gained lopsided benefits. 

Doing novel things that no one else has done before has the potential to bring unbridled gains. The caveat is that you have to do things that others find value in. Dexter accidentally did things that others found value in. He was plain lucky. You’ve got to create your luck.

Value x Scarcity = Immense profits

When you do a valuable thing that no one else is doing, your earnings multiply. Because scarcity is a multiplier.

But going against the crowd and doing things no one else does takes courage. We are social animals. We like the feeling of acknowledgement. We love getting praised. We want to fit in. Consciously going against the crowd can be mentally difficult.

Solomon Asch conducted an experiment to prove this. Participants were shown a line and they had to pick another line of the same size from three choices given to them. But unknown to them, the participants were placed in a room with actors who all gave the same wrong answer. And matched the line with another line that wasn’t of the same size. 

66% of the participants conformed with the actors and gave the wrong answer as well – even though the correct answer was obvious!

Going against the crowd is very difficult. So what can you do?

Training to become a contrarian

1. Awareness

It starts with awareness. Know that you will have to break away from groupthink to go further than the group. 

“The person who follows the crowd will usually get no further than the crowd. The person who walks alone is likely to find himself in places no one has ever been before.” – Francis Phillip Wernig 

2. Blinders

Do you know how warriors run their horses straight into a skirmish? By covering their eyes so that they can’t see what’s happening around them. 

You’ve got to get blinders too. And cut the negative people out. People who judge you, and criticize you, and give unsolicited negative feedback because you’re not doing what everyone else is doing – because you’re going against the grain.

3. Practice unconformity

Do small inconsequential things that others don’t. Be the first one to try a new weird fad. Deliberately take an opposite viewpoint and play the devil’s advocate during friendly conversations (without arguing!). 

Accept risk and get out of your comfort zone. Play the Rejection Therapy game where you ask strangers for weird favours like giving you a ride across town until they tell you “No.” Your goal being to collect 100 rejections in 100 days.

Action Summary:

  • Do things that no one else does. Because your goal is to be correct when no one else is.
  • Build the mental strength to be a contrarian.