I’ve spent a lot of time lately looking at the portfolios of savvy Singaporean investors.
Usually, they show them to me with a certain amount of pride. And why shouldn’t they? They own the “Great Pillars” of our economy. You know the ones: the three big banks, a couple of world-class telcos, and the “blue-chip” REITs that own our favourite shopping malls.
It feels comfortable. It feels like home.
But here’s what troubles me. As I’ve been saying for decades now, the most dangerous place to be is exactly where everyone else is standing.
The “Top 10” Illusion
Most investors think they are diversified because they own ten different stocks. But if you look under the hood, a startling pattern emerges.
If your “diversified” portfolio looks like a mirror image of the Straits Times Index, you aren’t actually diversified. You are concentrated.
Let me show you what I mean.
Say interest rates fall. Bank net interest margins compress, and with them, the dividends that so many investors depend on. But falling rates also shift REIT valuations. And if the Singapore property market slows at the same time, both banks and REITs feel the squeeze.
Three different “sectors.” One macro event. Your entire portfolio moves in the same direction.
That’s not diversification. That’s one big bet dressed up in ten stock names.
And here’s the part that stings. Ten years ago, many blue-chip REITs were yielding 6% to 7%. Today, a good number of them yield closer to 4% to 5%. The crowd has bid up prices, and the yields have compressed. The “safe” income you were counting on has been quietly shrinking. Not because the businesses failed, but because everyone else found them too.
This is the “Income Problem” that most investors don’t see coming until the dividends start to stall.
Why “Boring” Isn’t the Problem. Fishing in the Same Pond Is
We have always preached the gospel of “Getting Rich Slowly” by buying boring, stable, cash-generating businesses. I still stand by that 100%.
The principle is sound. But the application has gotten crowded.
When every institutional fund, every robo-advisor, and every retail investor is fishing in the same pond, you are all fighting for scraps of yield. The philosophy isn’t broken. But if you only apply it to the same 20 Singapore blue chips as everyone else, you are leaving yourself exposed.
The Smart Investor’s Question
To be a disciplined income investor, you have to be willing to ask the question that makes others uncomfortable:
“If my top three dividend payers hit a structural speed bump tomorrow, does my income plan survive?”
If the answer is “no,” then you don’t have a portfolio. You have a dependency.
True financial resilience doesn’t come from owning the biggest companies. It comes from owning uncorrelated income engines. Businesses that generate cash independently of each other, across different sectors, different markets, and even different countries.
It means looking beyond the obvious names. Beyond the index. Beyond even Singapore.
And yes, it also means looking at businesses that the big money can’t be bothered with. Companies with market caps smaller than a single DBS branch’s loan book, but with cash flow discipline that would put some blue chips to shame. Smaller doesn’t mean reckless. More often, it means overlooked.
Building these kinds of income streams isn’t about randomly adding more stocks. It takes real discipline. In what you select, how you size it, and how the pieces fit together.
What’s Coming
I’ve been doing a lot of thinking and a lot of research into how to build these extra engines.
Because in a world that is getting more crowded and more expensive, the old “buy and forget” strategy for blue chips isn’t just comfortable. It’s fragile.
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