It Pays to Be a Rebel
How not being popular made me a good investor today
Before jumping into this week’s letter, thought I’d share a recent article published by The Guardian: The K-shaped Christmas: wealthy few drive holiday spending splurge while many struggle to get by
If you recall, I wrote about the K-Shaped holiday season in our newsletter last week.
Is the prestigious UK newspaper, The Guardian, reading our newsletter?
I was not a popular kid growing up.
While others played sports or hung out in big groups, I was off in my own world.
The nerdy kid.
The quiet one.
The one who’s ignorant about what’s around him.
At the time, it did not feel like a superpower.
But looking back, it shaped everything about how I invest today.
Because being the odd one out taught me to become fiercely independent.
I learned not to worry about what was popular at school or what everyone else was doing.
That kind of independence does not earn you a ton of friends as a teenager, but it does something far more valuable.
It trains you to think differently.
And in investing, the people who think differently are usually the ones who come out ahead.
A good investor is a contrarian
One of the greatest investors in history, Warren Buffett, is often cited for encouraging people to become greedy when others are fearful and fearful when others are greedy. His entire career has been a reminder that following the crowd rarely leads to extraordinary outcomes.
If you have been following me for a while, you know I have been cautious over the past year.
I am still cautious on many things:
Stocks are trading at historic high valuations
Commercial office real estate continues to struggle in many key markets
Many regional banks in the US are still in a mode of “extend and pretend” on the non-performing loans on their books
While many investors are now also concerned about risks, as reflected in CNN’s Fear & Greed Index, I am starting to see opportunities surfacing.
In other words, I am becoming “greedy” again.
The pioneer of contrarian investing
John Templeton pioneered contrarian investing.
He focused on buying at points of “maximum pessimism.”
Source: https://www.philanthropyroundtable.org/hall-of-fame/john-templeton/
Contrarian investing, which Templeton mastered, means deliberately going against prevailing market trends. While most investors follow the crowd—buying when markets are rising and selling when they’re falling—contrarians do the opposite. They look for assets everyone else avoids, believing that markets tend to overreact in both directions. This approach requires tremendous discipline and courage, as it often means buying during crises when others are panicking.
Following this contrarian investing philosophy, he bought shares of European companies during the darkest days of World War II, when most investors thought Europe would never recover. He also famously sold off his tech stocks before the dot-com bubble burst in 2000.
Source: https://www.investopedia.com/world-s-11-greatest-investors-4773356
A contrarian doesn’t win the popularity contest
Playing the opposite game rarely earns applause.
When everyone is bullishly optimistic, people think you are negative.
When everyone is scared, they think you have lost your mind.
But I am not here to win a popularity contest.
I am here to find great investment opportunities with lower relative risk.
This is why I previously mentioned the term asymmetrical returns.
It is the idea that a small amount of downside can come with a large amount of upside when the setup is right.
And today, I am seeing pockets of exactly that.
For Passive Investors or Financial Partners, there are opportunities emerging in pockets of the market, offering compelling risk adjusted returns, if one knows where to look.
For Managing or Working Partners, GPs, there are once in a generation moments appearing today. These moments usually do not appear when the crowd is confident. They only show up when the sentiment is mixed, or outright fearful.
Tonight, I’ll be sharing the opportunities I’m seeing today
As mentioned in last week’s newsletter, I’m currently hosting a 12 Days online event - 12 Days of Christmas and Holidays - Gift of Knowledge to Real Estate Investors.
Tonight, I will be speaking on: Where I’m investing money today after growing 100+ units
I will be presenting on the various opportunities I’m personally involved.
Disclaimer: There are no investment opportunities offered, the session is for education purpose only. Using examples to demonstrate asymmetrical returns.
If you are interested, here’s the link to attend:
If you like my work, I invite you to share it with others.
Eric Chang
Calgary, Alberta, Canada
December 9, 2025
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